The Twenty Minute VC

Daniel Kan is the Chief Product Officer @ Cruise, the company building cutting-edge hardware and software that work seamlessly together to transform the way we all experience transportation. In 2016, Cruise was acquired by GM for a reported $1Bn. Since the acquisition Cruise has raised $7.25 billion in committed capital and has attracted SoftBank, Honda, and T. Rowe Price as investors. As for Daniel, he started his career at a startup called UserVoice. He then founded Exec, an on-demand hospitality service company, and successfully sold Exec to Handy. As a result of his many success, Daniel was listed as number 7 on Fortune’s 2016 40 under 40 list for the most influential people in business.

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In Today’s Episode You Will Learn:

1.) How Daniel made his way into the world of startups and came to co-found the game-changing company of the next movement mega wave of transport innovation in Cruise?

2.) What have been Daniel’s biggest lessons on what works for leaders in scaling themselves? How can a leader ensure their team feel real ownership and accountability for their roles? How does Daniel think about KPI and goal-setting? How does Daniel look to strike the balance between ambitious but achievable goals and then unrealistic?

3.) How does Daniel think about micro-management? Is there ever a time for it? What are the leading indicators you or someone on the team is micro-managing? What can they do to correct it? What are the dangers of micro-management? How does Daniel think about assessing human potential in terms of a stretch VP and a stretch too far?

4.) Why does Daniel believe that “if you are not growing, you are dying”? What has been transformational to Daniel in increasing his own level of self-development and learning? How does the organisation need to be set up to ingest these learnings in real-time and improve? Where do many go wrong when it comes to mistakes and learnings?

5.) At acquisition, Cruise had just 40 team members, today the team consists of 1,460. What have been some of Daniel’s biggest lessons in the process of scaling the team with such rapidity? What have been some of the core challenges? How has Daniel’s style of leadership had to change and evolve with the growth?

Items Mentioned In Today’s Show:

Daniel’s Fave Book: Shogun: The First Novel of the Asian saga: A Novel of Japan

As always you can follow Harry, The Twenty Minute VC and Daniel on Twitter here!

Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Puneet Agarwal is a Partner @ True Ventures, one of the leading early-stage VC funds of the last decade with big wins including Fitbit, Peloton, Ring, Hashicorp, Duo Security and Blue Bottle Coffee, just to name a few. As for Puneet, at True he has led deals in Duo Security, Tray.io, Lumity, Solo.io and more. Before the world of VC, Puneet spent 6 years in product management with Geodesic Securities and BEA. Before product management, Puneet actually cut his teeth in the world of VC as an associate at Mayfield which he joined post a 2-year stint at JP Morgan.

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In Today’s Episode You Will Learn:

1.) How Puneet made his way into the world of venture from JP Morgan? How seeing the boom and bust cycle impacted his investing mindset today? How his career in operations led to his joining True?

2.) Why does Puneet believe that EQ is going to separate the good from the great in venture firms over the next decade? What can VCs do to remove the barriers to access them? What have been Puneet’s biggest lessons on what it takes to build real relationships of trust and respect with founders? What is a test of a strong founder <> VC relationship?

3.) What does Puneet believe are the 2 feelings a board member can bring to a board meeting? Why would an investor bring fear to the board meeting? Why is this a sign and result of the culture of their own venture partnership? What have been Puneet’s biggest lessons on how investors can bring the feeling of safety to a board meeting? How has Puneet changed his style of board membership over the last decade?

4.) Why does Puneet strongly advocate for a venture structure without attribution? What are the benefits of not having attribution? How does this also impact the re-investment decision-making process? How does Puneet think about how he spends his time across the portfolio? What have True done to optimise the investment decision-making process? Why is unanimity not required?

5.) How does Puneet and True think about portfolio construction today? What amount of initial checks give them enough diversification to feel comfortable but also enough reserves to double down? Does Puneet believe that ownership can be built over time? Where does Puneet believe there is a whole in the funding environment? How does True think about minimizing risk on the first check?

Items Mentioned In Today’s Show:

Puneet’s Fave Book: Billion Dollar Whale: The Man Who Fooled Wall Street, Hollywood, and the World

Puneet’s Most Recent Investment: Upsie

As always you can follow Harry, The Twenty Minute VC and Puneet on Twitter here!

Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

 

Hiten Shah is the Co-Founder @ FYI, the startup that allows you to find your documents in 3 clicks or less. Before FYI, Hiten co-founded QuickSprout alongside Neil Patel, together they scaled the platform to over 500,000 readers every month. Before QuickSprout, Hiten was the Co-Founder and CEO of KISSmetrics, raising over $19m in the process for the company from the likes of True Ventures, Uncork Capital and Felicis Ventures just to name a few. Finally, Hiten is also the Co-Founder @ Crazy Egg, the heat mapping tool used by hundreds of thousands to improve the effectiveness of their websites. Finally, Hiten is also an angel investor with a portfolio including Buffer, Clearbit, Front, Gusto and more incredible companies.

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In Today’s Episode You Will Learn:

1.) How Hiten made his way into the world of startups, growth market and SaaS and how that led to his co-founding FYI today? Having founded multiple startups, does Hiten agree with Joe Fernandez @ JoyMode that “serial entrepreneurship is overrated”? Why does Hiten believe that fundamentally, nobody knows what they are doing?

2.) How does Hiten feel about the compression of fundraising timelines today? How does Hiten advise founders on building authentic relationships with investors? What is it crucial that founders understand about the investing class? How does Hiten advise founders on building hype and urgency within their fundraising? What works? What does not?

3.) Why does Hiten believe that we have seen the eradication of the friends and family round? What other large trends has Hiten observed in the early stage over the last few years? How does Hiten advise founders on how to approach which seed investors they take on board? Does Hiten think founders and investors can be friends?

4.) How has Hiten seen himself change and evolve as a leader over the last decade? What have been the biggest learnings on what great leadership really means? What are the 5 core elements that all great leaders must focus on? How does he split his time across these 5 disciplines? Where do founders often not spend adequate time among the 5?

5.) How does Hiten think about the element of “burnout” and depression today? Has Hiten ever felt burned out himself? How does this stress manifest itself? How does Hiten think that burnout and control are correlated? What can one do to change their relationship to control? What has worked for Hiten? What has not?

Items Mentioned In Today’s Show:

Hiten’s Fave Book: The Courage To Be Disliked 

As always you can follow Harry, The Twenty Minute VC and Hiten on Twitter here!

Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Chetan Puttagunta is a General Partner @ Benchmark, one of the most successful funds of the last decade with a portfolio including the likes of Uber, Twitter, Dropbox, WeWork, Snapchat, StitchFix, eBay and many many more. As for Chetan, at Benchmark he has led deals in the likes of Duffel, Sketch and Pachyderm. Before Benchmark, Chetan was a General Partner @ NEA where he led investments in Elastic, MongoDB and Mulesoft to name a few.

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In Today’s Episode You Will Learn:

1.) How Chetan made his way into the wonderful world of venture, came to invest in Mulesoft and Elastic and how that led to becoming a GP with Benchmark today?

2.) How does Chetan feel about the push to run businesses based on metrics and benchmarks relative to other companies? What are the metrics they should hone in on? What are the metrics they should disregard? How does Chetan advise his portfolio on the right way to view competition? What is core to analysing competition effectively?

3.) How does Chetan assess the “war for talent” in terms of startup recruiting today? How do the very best CEOs recruit the best talent to their team? Who has done this best from Chetan’s portfolio that comes to mind? How much weight does Chetan place on references? What should one watch out for with references?

4.) With the rise of remote, does Chetan believe that a startup even has to have an office in SF today? How does Chetan think about the “tribal knowledge” that remains within the valley? What does Chetan advise his companies that are not in the valley and contemplating it? What works? What does not?

5.) How does Chetan think about market size today when considering new opportunities? Where does Chetan think most managers go wrong when assessing TAM? How does Chetan think about time allocation across the portfolio? What have been his biggest lessons on managing his time effectively as an investor and board member?

Items Mentioned In Today’s Show:

Chetan’s Fave Book: Shoe Dog: A Memoir by the Creator of NIKE

Chetan’s Most Recent Investment: Duffel

As always you can follow Harry, The Twenty Minute VC and Chetan on Twitter here!

Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Waseem Daher is the Founder and CEO @ Pilot, the startup that takes care of your bookkeeping from start to finish so you can focus 100% on making your business succeed. To date, Waseem has raised over $58m in funding from some of the very best firms and people in the business including Index, Stripe, Okta’s Frederic Kerrest, Gusto’s Josh Reeves, Stripe’s Patrick and John Collison and Lola’s Paul English, just to name a few. As for Waseem, Pilot is the 3rd business he has founded with his co-founders, the first being Ksplice and the second Zulip, which was acquired by Dropbox in 2014. He has also enjoyed spells with the likes of Oracle and Dropbox in the interims.

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In Today’s Episode You Will Learn:

1.) How Waseem made his way into the world of startups over 15 years ago and how that lead to his founding of Pilot today, changing the world of accounting? Does Waseem agree with Joel Fernandez at JoyMode that “serial entrepreneurship is overrated? What has Waseem done differently this time as a result of his 2 prior founding experiences?

2.) Why does Waseem believe that “passion is overrated when it comes to starting companies”? If passion is not fundamental, what does Waseem believe is fundamental to ensuring one sticks the course? How does Waseem think about the craft of company building as a passion in itself?

3.) What is it about Waseem’s relationship with his 2 co-founders that makes it so successful for the third time around this time? What do they do to ensure that unity and trust remains? Where do they have weaknesses and flaws in the co-founding relationship as a result of it’s maturity? What advice does Waseem give to newer co-founding partners?

4.) Waseem has previously said that “VC is overrated”. What does he mean by this? How does Waseem think about the decision to bootstrap vs to raise VC? What are Waseem’s biggest lessons when it comes to investor selection? How much of a role does brand play? What core questions should the founders ask the VC?

5.) What does Waseem mean when he says, “never sell your company”? What were his biggest lessons from exiting two companies to Oracle and Dropbox? How did it shape his thinking on M&A and exits? How has Waseem seen his role scale and develop as a leader and as CEO? What are the biggest challenges he has found in his personal scaling?

Items Mentioned In Today’s Show:

Waseem’s Fave Book: Harry Potter

As always you can follow Harry, The Twenty Minute VC and Waseem on Twitter here!

Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Smart executives and business owners know that harnessing the power of
AI, embracing the cloud, and prioritizing cybersecurity are the cornerstones of growth. Every day, Wrike helps thousands of companies worldwide do this by revolutionizing how they approach work. Our secure, automated,cloud-based work management tool helps businesses future proof their cultures and evolve fast. How? Wrike ‘s award-winning, collaborative, all-company platform keeps everything in one easily-accessible space. Time to embrace next-gen work management at the executive level and encourage lean thinking from the top down. With Wrike, crushing your objectives and mitigating risks at scale is a cinch. Give Wrike a try for free.

 

Brian Norgard is the Former Chief Product Officer at the top-grossing mobile app in the world, Tinder. In less than 3 years, Tinder created over $11Bn in market value and with Brian’s contribution to the creation of Tinder Gold, Superlike and Boost, the platform has seen over 200m downloads and created millions of matches. Prior to Tinder, Brian founded Tappy, a mobile messaging application backed by Kleiner Perkins and acquired by Tinder. Before that, Brian built one of the fastest-growing Facebook applications in history (Chill) which reached over 30MM people. Fun fact about Brian also, at 25, Brian was the youngest GM/VP in the history of Rupert Murdoch’s News Corp after the acquisition of his first company Newroo where he served as the GM of MySpace News. If that was not enough, Brian is also a prolific angel investor with investments in Tesla, SpaceX, AngelList and Coinmine.

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In Today’s Episode You Will Learn:

1.) How Brian made his way into the world of startups and came to be the youngest VP at News Corp at the tender age of 25? How did that lead to his becoming CRO then CPO @ Tinder?

2.) What is the No 1 reason that products fail today? What can founders and designers do to retain the simplicity of product over time? How does complexity change the product experience? Why does Brian believe that product experience is an art? Bring in science, to what extent does Brian believe testing and iteration is key to success in product? How does one know how long is enough time to test for vs too short and not enough data?

3.) When thinking about distribution, what does Brian look for in the way that people describe a product to their friend? How does Brian think that the most successful products bake distribution into the core user behaviour? How does Brian think about community building around product? Who has done this best in Brian’s mind?

4.) How should the very best founders and product people think about product risk? How can they know when to use risk to their advantage vs be mindful of excessive risk? On the features themselves, how important is it for a product to be 10x cheaper/faster etc? Why does Brian believe that is largely VC jargon?

5.) What were Brian’s biggest takeaways from launching Tinder Gold and seeing Tinder become the Top Grossing App in the world? How does that sort of event also impact the team? How does Brian think about whether one should celebrate those moments or push forward to the next goal?

Items Mentioned In Today’s Show:

Brian’s Fave Book: The Old Man and The Sea

As always you can follow Harry, The Twenty Minute VC and Brian on Twitter here!

Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Smart executives and business owners know that harnessing the power of
AI, embracing the cloud, and prioritizing cybersecurity are the cornerstones of growth. Every day, Wrike helps thousands of companies worldwide do this by revolutionizing how they approach work. Our secure, automated,cloud-based work management tool helps businesses future proof their cultures and evolve fast. How? Wrike ‘s award-winning, collaborative, all-company platform keeps everything in one easily-accessible space. Time to embrace next-gen work management at the executive level and encourage lean thinking from the top down. With Wrike, crushing your objectives and mitigating risks at scale is a cinch. Give Wrike a try for free.

Jesse Beyroutey is a General Partner @ IA Ventures, one of the top-performing early-stage funds of the last decade. Their incredible portfolio includes the likes of TransferWise, DataDog, Digital Ocean, X.ai and The Trade Desk, just to name a few. As for Jesse, his investments at IA include Digital Ocean, IronClad, TransferWise, Sight Machine and more fantastic companies. Prior to joining the world of venture, Jesse studied Systems Engineering at the University of Pennsylvania.

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In Today’s Episode You Will Learn:

1.) How Jesse made his way into the world of VC pretty much straight out of University and how that led to his being a GP with IA today?

2.) What is Game Theory? What does it mean to Jesse and how does it impact his investing mindset today? How does Jesse think about and assess startup positioning today? How important is positioning in the early days of the company? How does Jesse think about data as a sustainable moat or not? Does Jesse think in today’s excess supply of capital environment that cash alone can be a moat?

3.) How does Jesse and IA think about portfolio construction today? Does Jesse ever feel the “pressure to deploy”? How have IA structured their own fundraises to ensure they never feel that pressure? How important a role does ownership play for Jesse when making an investment? Does Jesse believe ownership is built on first check?

4.) How does Jesse assess his own price sensitivity? How has it changed over the last 8 years? How does Jesse and IA approach both investment decision-making and reserve allocation decisions? How does the lead rely on the rest of the team when making decisions? Why does capital efficiency become a core question when determining reserve allocations?

5.) Why does Jesse feel that the reading to writing ratio that currently exists between founders and investors needs to change? What should the ratio be? How does the relationship between founder and investor change when the investor provides more content? How does Jesse look to avoid news cycles in the week? What works? What does not? What is Jesse’s advice for anyone looking to do the same?

Items Mentioned In Today’s Show:

Jesse’s Fave Book: 7 Powers: The Foundations of Business Strategy

Jesse’s Most Recent Investment: Gauntlet 

As always you can follow Harry, The Twenty Minute VC and Jesse on Twitter here!

Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Sid Sijbrandij is the Founder & CEO @ Gitlab, a single application for the entire software development lifecycle. From project planning and source code management to CI/CD, monitoring, and security. To date, Sid has raised over $145m in funding for Gitlab from the likes of GV, August Capital, YC, Khosla and Goldman Sachs just to name a few. What is incredible, Sid has scaled the team to over 762 team members across 55 countries and is famed for his openness and transparency on how he builds both the product and company. You can find the fantastic Gitlab handbook here.

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In Today’s Episode You Will Learn:

1.) How Sid made his way into the world of startups, learned Ruby in the early days and came to found Gitlab? What was that a-ha moment?

2.) In 2019 Gitlab is growing from 400 to 1,000 people, what are the biggest challenges that come with such operational growth? How does one hire at such pace and retain quality? How does Sid think about the right way to onboard new employees? How does Sid think about KPI and goal setting in the early days?

3.) Today all 750 Gitlab employees are remote, what does Sid believe is the secret to making remote teams work at scale? How does Sid think about the balance between fast shipping cadence and perfect product releases? Why does Sid believe, “you have to have a low level of shame on the product you release”?

4.) How does Sid think about operating Gitlab as a totally transparent company? What does that mean both in reality and in process? Why does Sid believe it is optimal to have a roadmap that is open for everyone to see? What are the pros? What are the cons of such transparency? How do competitors respond?

5.) If every great business is bundling or unbundling, where does Sid believe he and Sid are in the process today? How does Sid think about being too much to too many people? How does the open-source community really come into play in the development of Gitlab?

Items Mentioned In Today’s Show:

Sid’s Fave Book: High Output Management

As always you can follow Harry, The Twenty Minute VC and Sid on Twitter here!

Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Smart executives and business owners know that harnessing the power of
AI, embracing the cloud, and prioritizing cybersecurity are the cornerstones of growth. Every day, Wrike helps thousands of companies worldwide do this by revolutionizing how they approach work. Our secure, automated,cloud-based work management tool helps businesses future proof their cultures and evolve fast. How? Wrike ‘s award-winning, collaborative, all-company platform keeps everything in one easily-accessible space. Time to embrace next-gen work management at the executive level and encourage lean thinking from the top down. With Wrike, crushing your objectives and mitigating risks at scale is a cinch. Give Wrike a try for free.

Santi Subotovsky is a General Partner @ Emergence Capital, one of the valley’s leading venture firms of the last decade focusing on enterprise & SaaS applications. Within their incredible portfolio is the likes of Salesforce, Zoom, Box, Veeva Systems, SuccessFactors and many more. As for Santi, he has led deals in the likes of Zoom, Crunchbase, Clearbanc, Top Hat and Chorus.ai to name a few. Before Emergence, Santi founded AXG Tecnonexo, a SaaS e-learning company in Argentina which he expanded to 150+ employees across Latin America and the U.S. Santi is also a founding board member of Puente Labs, an organization that helps founders of Latin American high-potential growth companies scale their businesses globally.

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In Today’s Episode You Will Learn:

1.) How Santi made his way from founding a Latin American EdTech business to being one of the valley’s most successful investors of 2019 with Zoom’s IPO? What was the biggest barrier he faced when getting into VC? How did he overcome it?

2.) What does Santi believe his superpower as an investor is? What did Santi see in Eric Yuan and the 30 person team at the time that made him believe they would be successful? What made how Eric thinks about presents product so special? What did the relationship building process look like between Eric and Santi in the early days?

3.) How does Santi like to work with his portfolio companies? How does Santi think about time allocation across the portfolio? Why does Santi believe it is crucial to not just spend time with the CEO but the exec team also? Where does Santi most like to provide value and leverage to the CEO? Why does Santi believe all VCs are just sales reps?

4.) Why does Santi believe that a vertically focused fund is the optimal strategy to pursue today? What are the benefits? What are the drawbacks? How does Santi think about the obvious overlap between consumer and enterprise today? With the thematic focus, how does Santi think about loss ratio and batting average? How does Emergence approach the element of both ownership and price? Where do they optimise?

5.) With larger and larger funds, how does Santi see the future of venture? Why does he believe that we will see vertically focused capital-as-a-service? What does this look like in reality? Is Santi concerned by the extended window of privatisation that is now present in today’s capital markets? How concerned is Santi by the compression of fundraising timelines and what does that to investor <> founder relationships?

Items Mentioned In Today’s Show:

Santi’s Fave Book: Candide by Voltaire

Santi’s Most Recent Investment: Openpath

As always you can follow Harry, The Twenty Minute VC and Santi on Twitter here!

Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Joseph Gordon-Levitt is the Founder @ HitRecord, the startup that allows you to be creative, together, encouraging less self-promotion and more collaboration, so you can create things you couldn’t have made on your own. To date, Joe has raised funding from some personal favourites of mine in the form of Alex @ Javelin, Masterclass Founder David Rogier, Twitch Founder Kevin Lin and CrossLink Capital just to name a few. Alongside his role with HitRecord, Joe is also an A-List Hollywood Actor and filmmaker starring in some of my favourite films of all time including The Dark Knight Rises, Inception, 10 Things I Hate About You and many many more.

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In Today’s Episode You Will Learn:

1.) How Joseph made his way into the world of technology and startups with the founding of HitRecord? How did much of Joe’s early acting career inform much of the HitRecord product today?

2.) Having had such success in the acting world, what caused Joe to really push forward with HitRecord? Question from David @ Masterclass: who has been Joe’s biggest mentors in his transition to tech? What have been his biggest takeaways from them? How does Joe balance both being an actor and entrepreneur at the same time? What are the challenges?

3.) Why did Joe decide now was the time to raise VC funds for HitRecord this late into the company life? How does Joe approach the element of investor selection? What specific value add did Joe want to see in his potential investor? How did the pitch process go? How does it compare to presenting for a role in the acting world? What was Joe’s biggest lesson about what successful technology pitches do?

4.) When Joe thinks about the HitRecord community, what has surprised him the most with the growth of the community? Why have they purposefully decide to never spend on user acquisition or traffic? What is the strategy behind this? What is Joe’s biggest advice to individuals wanting to scale their community and the essentials?

5.) How does Joe assess both the content and social media landscape today? Why is the creative spirit of the world being killed by the current ad model of social platforms? How does Joe think this can be countered and where does HitRecord fit into this evolving landscape?

Items Mentioned In Today’s Show:

Joe’s Fave Book: Letters To A Young Poet

As always you can follow Harry, The Twenty Minute VC and Joe on Twitter here!

Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Smart executives and business owners know that harnessing the power of
AI, embracing the cloud, and prioritizing cybersecurity are the cornerstones of growth. Every day, Wrike helps thousands of companies worldwide do this by revolutionizing how they approach work. Our secure, automated,cloud-based work management tool helps businesses future proof their cultures and evolve fast. How? Wrike ‘s award-winning, collaborative, all-company platform keeps everything in one easily-accessible space. Time to embrace next-gen work management at the executive level and encourage lean thinking from the top down. With Wrike, crushing your objectives and mitigating risks at scale is a cinch. Give Wrike a try for free.

Byron Deeter is a Partner @ Bessemer Venture Partners where he has established himself as one of the leading investors in SaaS and Cloud authoring the iconic laws on the state of cloud computing. In terms of track record, fourteen of Byron’s investments are valued above one $1 billion, including eight IPOs and counting. Byron’s investments include the likes of Twilio, Intercom, SendGrid, Gainsight, Box, DocuSign and many more. Prior to the world of venture, Byron was a Bessemer Founder raising his Series A from them back in 2000 with Trigo Technologies. The company rapidly scaled to profitability and was acquired by IBM.

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In Today’s Episode You Will Learn:

1.) How Byron made his way into the world of venture from founding Trigo Technologies and selling to IBM in 2005? How have seeing multiple booms and busts impacted Byron’s investment mentality today?

2.) What the heck is going on in cloud today? Is Byron concerned by the very rich multiples being paid in the ecosystem today? How does Byron think about how public market performance impacts his day to day role investing? Why does Byron believe that the floodgate for cloud IPOs is about to burst open?

3.) Having seen so many cloud IPOs, what should founders take from the lessons of those that have already been so successful? With 14 $Bn companies, what does Byron attribute his investing success to today? How does Byron think about what he wants to invest in today? Are we in an entirely new wave of cloud?

4.) As a former founder, how does Byron think that he engages differently with founders than more financial backgrounded VCs? What can board members really do to build that trusted relationship with the founder in the early days? Is it good for founders and board members to be friends? Is there a line of professionalism that has to be drawn?

5.) How has Byron seen his style of board membership change over the last decade? What would his advice be to someone who has just gained their first institutional board seat? What does Byron believe makes the best board members? What founder he has worked with most excels when it comes to board management? What made them so extraordinary?

Items Mentioned In Today’s Show:

Byron’s Fave Book: AI Superpowers, Legacy

Byron’s Most Recent Investment: ScaleFactor

As always you can follow Harry, The Twenty Minute VC and Byron on Twitter here!

Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Alex Rodrigues is the Founder & CEO @ Embark, the world’s leading developer of self-driving trucks. Embark operates the longest automated freight route in the world. To date, Alex has raised over $47m in funding for Embark from some of my favourites in the form of Pat Grady @ Sequoia, Matt Ocko @ Data Collective, SV Angel and Y Combinator, just to name a few. As for Alex, it started early with his winning a World Robotics Championship while he was in Middle School (the championship was for adults). Post that incredible achievement he dropped out of Waterloo, became a Thiel Fellow, worked as a software engineer @ Nuance Communications, before joining Khan Academy as a software engineer and also teaching robotics @ Khan Lab School.

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In Today’s Episode You Will Learn:

1.) How Alex made his way from winning World Robotics Championships while he was in Middle School to founding the leader developer of autonomous trucks in Embark?

2.) Why does Alex believe in the medium to long term, self-driving is still under-hyped? What is the market analysis to support this? How did his meetings with the world’s best public markets investors impact his thinking here? How does Alex think about adoption timelines for self-driving? How do investors think about this when investing?

3.) Does Alex believe that when it comes to self-driving vehicles, they will largely be a public utility? What ownership mechanism does Alex expect to see? What are the pros and cons associated with each? How does Alex think about ownership of the data generated through self-driving? How do we balance privacy and public safety?

4.) With such large milestones and proof points in self-driving, how does Alex think about effective goal setting? What are the core KPIs to be driving for? How can they be broken into more meaningful and achievable wins for the team to get around? What is the core challenge to morale maintenance when the challenge is so long term?

5.) Where does Alex see the commonalities in the biggest mistakes that young founders make? What does Alex know now that he wishes he had known at the start? What have been Alex’s biggest lessons on hiring the world’s best in their respective fields? What have been Alex’s biggest takeaways when it comes to successful board management?

Items Mentioned In Today’s Show:

Alex’s Fave Book: High Output Management

As always you can follow Harry and The Twenty Minute VC on Twitter here!

Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Pat Grady is a Partner @ Sequoia, one of the world’s leading and most renowned venture firms with a portfolio including WhatsApp, Zoom, Stripe, Airbnb, Github and many more incredible companies. As for Pat, at Sequoia he co-leads the firms growth investment team and has been involved with some of the true greats, Hubspot, Zoom, Okta, Qualtrics, the list goes on. Prior to Sequoia Pat spent three years with Summit Partners.

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In Today’s Episode You Will Learn:

1.) How Pat made his way from Summit Partners to co-leading Sequoia’s growth investment team? Was it intimidating for Pat entering a partnership with Jim Goetz, Don Valentine, Roelof Botha? How did he manage those nerves?

2.) So many different funds and activities, so what is Sequoia focused on today? Where does Sequoia think about their ideal insertion point today? How do they see the deployment of their blended capital across rounds? Does Pat believe in ownership on first check or building ownership over time? How does Pat think about the extended window of privatisation with IPOs being continuously delayed?

3.) Does Pat believe that VC really is a team sport today? Does Pat agree with Josh Kopelman’s statement, “I would rather be a better picker of partners than investments”? What are the core requirements, skills and traits that Sequoia looks for when adding to their partnership?

4.) What is the investment decision-making process at Sequoia? How do they feel about unanimity vs conviction based investment decisions? What are the pros and cons of each? What does Pat believe is the most non-obvious investment decision that Sequoia have made? Sequoia run an incredibly rigorous process when investing, how does Pat balance between that level of rigour with the speed to win the deal?

5.) What advice would Pat give to someone that has just gained their first institutional board? What does Pat know now that he wishes he had known when he started in VC? How does Pat think about time allocation across the portfolio? Concentrate on winners or the strugglers are where your reputation is built? Leading Sequoia Growth and with a beautiful family, how does Pat approach work/life balance?

Items Mentioned In Today’s Show:

Pat’s Fave Book: God Friended Me

Pat’s Most Recent Investment: Embark: Revolutionizing Commercial Transport 

As always you can follow Harry, The Twenty Minute VC and Pat on Twitter here!

Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Steven Galanis is the Founder & CEO @ Cameo, the startup that allows you to book personalised shoutouts from your favourite people. To date, Steven has raised over $65m in VC funding for Cameo from some of the very best in the business including Bedrock, Nicole Quinn @ Lightspeed, Kleiner Perkins and Spark Capital, just to name a few. Prior to founding cameo, Steven was a Senior AE @ LinkedIn and before that was an options trader in Chicago. With their immense success, they have been featured in all major publications including The Ellen DeGeneres Show. Cameo has also been voted as “The Best Place To Work In Chicago” by GlassDoor.

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In Today’s Episode You Will Learn:

1.) How Steven made his way from AE @ LinkedIn to revolutionising what an autograph means today with his founding of Cameo?

2.) What does Steven believe is the No 1 reason that startup founders fail with their startup today? Why does Steven believe that you have to give up your job to pursue your startup, even in the earliest of days? What advice does Steven give to founders and young graduates who approach him for advice in the earliest of days?

3.) As the company scales, how does Steven think about and approach role allocation internally? How does he prioritise hiring for them? How does he think about internal upscaling? How has he dealt with letting go of responsibilities and delegating to the team? What are the core challenges here? What does he advise founders facing this?

4.) Steven has said before, “don’t let good get in the way of great”, what did he mean by this? How does he determine between good enough and a stretch too far? How does Steven think about the statement of hiring for 6 months ahead of where you are? What have been his biggest lessons from scaling internationally so fast?

5.) How does Steven think about and approach investor selection? What can founders really do to leverage their investor base and get the most value from them? How does Steven think about the incredibly high CACs of the core channels today? What must founders in the world of consumer do to acquire customers more efficiently?

Items Mentioned In Today’s Show:

Steven’s Fave Book: Blitzscaling: The Lightning-Fast Path to Building Massively Valuable Companies

As always you can follow Harry, Steven and The Twenty Minute VC on Twitter here!

Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Bill Gurley is a General Partner @ Benchmark Capital, one of the most successful funds of the last decade with a portfolio including the likes of Uber, Twitter, Dropbox, WeWork, Snapchat, StitchFix, eBay and many many more. As for Bill, widely recognised as one of the greats of our time having worked with the likes of GrubHub, NextDoor, Uber, OpenTable, Stitch Fix and Zillow. Prior to Benchmark, Bill was a partner with Hummer Winblad Venture Partners. Before entering venture, Bill spent four years on Wall Street as a top-ranked research analyst, including three years at CS First Boston where his research coverage included such companies as Dell, Compaq, and Microsoft, and he was the lead analyst on the Amazon IPO.

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In Today’s Episode You Will Learn:

1.) How did Bill make his way into the world of VC from Credit Suisse and come to be GP at one of the world’s leading funds in the form of Benchmark? What were Bill’s biggest takeaways from seeing the boom and bust of the dot com? How did that impact Bill’s investment mentality today?

2.) Why does Bill believe that one of the biggest challenges today is the abundance of capital? Subsequently, does Bill agree with Peter Fenton statement, “never turn down a deal based on the valuation it is a mental trap”? How does Bill assess his own price sensitivity? What was his learning here in meeting Larry and Serge early on with Google?

3.) How does Bill think about and approach market sizing today? How important is it to him when analysing an investment? Where does Bill believe a lot of managers make mistakes when assessing market sizing today? What was his big lesson here with Uber? How does Bill think about and evaluate market creation and market expansion plays?

4.) Bill has spent over 3,000 hours on some of the most famed boards of the last decade, how has Bill seen his style of board membership change over the last 10 years? What advice would you give to someone who has just joined their first board? How does Bill think about time allocation across the portfolio? What is the right ratio?

5.) How does Bill and Benchmark approach the element of partner selection today? What are the 5 core things that Bill looks for when adding to the partnership? What have Benchmark done that have allowed them to be so successful in generational transition? Why is an equal partnership so transformative when it comes to generational transition?

Items Mentioned In Today’s Show:

Bill’s Fave Book: Complexity: The Emerging Science at the Edge of Order and Chaos

Bill’s Most Recent Investment: Good Eggs

As always you can follow Harry, The Twenty Minute VC and Bill on Twitter here!

Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Justin Kan is the Founder and CEO @ Atrium, the startup providing a full-service corporate law firm that uses modern technology to give startups a legal experience that is fast, transparent, and price-predictable. To date, Justin has raised over $75m in funding from some of the best in the business including Founders Fund, a16z, First Round, General Catalyst, Thrive, Initialized and more. Prior to founding Atrium, Justin was a Partner @ Y Combinator, the globally renowned accelerator and the birthplace of some of today’s largest startups. Before that Justin was the Co-Founder @ Twitch, the world’s leading video platform and community for gamers which was acquired by Amazon for $970m. If that was not enough, Justin is also a prolific angel investor with investments in the likes of Cruise Automation, Rippling, Zenefits, Triplebyte and more.

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In Today’s Episode You Will Learn:

1.) How Justin made his way into the world of startups and YC? How that led to the founding of Justin.TV, later Twitch? What was that a-ha moment for Atrium?

2.) Why did Justin feel that being an investor full time was not for him? How does Justin think about and approach the learning process as a founder? What advice does Justin give to those who want to quit? What was it that made Justin embrace the series of self-improvement habits he now practices?

3.) What does Justin mean when he says, “attaching yourself to outcomes will only cause your own suffering”? How does Justin think about and advise founders when it comes to burnout? How does Justin feel about the “crushing it” culture in tech? What can we do to normalise vulnerability? What were Justin’s biggest takeaways from “The Score takes Care of Itself”?

4.) What have been Justin’s experiences with therapy? How does he advise founders thinking of engaging with therapists? What have been his biggest lessons that drive success in therapy? How does Justin look to show authenticity through positivity? What does that really mean?

5.) What have been Justin’s biggest takeaways from “The 15 Commitments of Conscious Leadership”? What are the core principles? What is required to roll out these values and principles within an organisation? What are the fundamental challenges to successfully roll this out on a large scale within your company?

Items Mentioned In Today’s Show:

Justin’s Fave Book: The 15 Commitments of Conscious Leadership

As always you can follow Harry, Justin and The Twenty Minute VC on Twitter here!

Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Jonathan Hsu is Co-Founder & General Partner @ Tribe Capital, one of Silicon Valley’s newest funds on the block being founded by Jonathan, Arjun Sethi and Ted Maidenberg. To date, Tribe has invested in the likes of Carta, Cover, Mode Analytics, Prodigy and SFOX. As for Jonathan, before founding Tribe he was a Partner @ Social Capital where he utilized data and technology to augment sourcing, evaluation of investment opportunities and the management and value add for portfolio companies. Before that he led the creation of the analytics and data science team at Facebook, including leading the hiring of 200 of the world’s leading data scientists and analysts.

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In Today’s Episode You Will Learn:

1.) How Jonathan made his way from leading 200 data scientists at Facebook to the world of venture and founding his own firm in the form of Tribe Capital today?

2.) If we structure VC simplistically, there are 4 core components:

• Sourcing: How does Jonathan think about the role of data in actively surfacing the best opportunities? that are the leading data fields that Jonathan would track? Why does Jonathan believe most early-stage firms are just using Linkedin Sales Navigator intelligently?
• Evaluating: How does Jonathan think about the potential for data to really aid in the picking process? At what stage does this really become possible? How much data is required for data to evaluate opportunities?
• Winning: Winning deals is seemingly a case of human relationships but how does Jonathan think intelligent data usage and benchmarking can actually help firms win the most competitive deals?
• Value Add: How does Jonathan think about portfolio management with data? How does this differ from the more traditional “value add” that other VCs provide? Where are the common pitfalls Series A companies you work with face in not achieving product-market fit?

3.) Given the data-driven nature of the approach, does Jonathan think that there is an optimal portfolio construction? Why does Jonathan strongly believe that historical loss ratios are too high? Does data allow firms to really intelligently price these assets at the Series A and B? What are the challenges in pricing these assets so early?

4.) How does Jonathan think about reserve allocation? Why is data more critical than ever in the decision to re-invest or not? What are the leading data signals that Jonathan looks for when determining reserve allocation? Why does Jonathan think that so many firms go wrong in how they approach reserve management and distribution?

5.) Question from Henry Ward @ Carta: What does N of 1 markets mean to you Jonathan? Why are they so inherently attractive? How do pricing dynamics play out in markets that are N of 1? How does Jonathan think about defensibility when analysing opportunities today? Is anything truly defensible anymore?

Items Mentioned In Today’s Show:

Jonathan’s Fave Book: The Origins of Political Order: From Prehuman Times to the French Revolution

Jonathan’s Most Recent Investment: Carta

As always you can follow Harry, The Twenty Minute VC and Jonathan on Twitter here!

Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Brad Bao is the Co-Founder & CEO @ Lime, the startup that provides distribution of shared scooters, bikes and transit vehicles, with the aim to reduce dependence on personal automobiles for short distance transportation. To date, they have raised over $775m in funding from the likes of Andreessen Horowitz, GV, IVP, Uber, Fifth Wall, GGV, Atomico and Bain Capital Ventures just to name a few. As for Brad, prior to founding Lime he was Managing Partner @ Kinzon Capital for close to 6 years and before that spent an incredible 8 years at Tencent in numerous different roles including VP of Business Development for Tencent Games and General manager for Tencent’s US branch where he was responsible for Tencent’s US operations.

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In Today’s Episode You Will Learn:

1.) How Brad made his way into the world of technology with Tencent, how that led to the world of investing and then what was that a-ha moment for the founding of Lime? How did Brad’s time with Tencent impact his operating mentality today with Lime?

2.) With significant levels of competition, how does Brad assess the competitive landscape today for micro mobility? Does Brad believe customer loyalty comes into play in the segment? Is capital itself a defensible moat in this market? Why is Brad adamant that it is important to spend $0 on marketing? What does this say about the product?

3.) How does Brad think about technological innovation within the space? Does it subscribe to Moore’s law in the advancement of the core components? How does Brad think about inherent trade-offs that have to be made in product decisions? How does Brad think about prioritising for unit cost vs product superiority? Why can you not have it all?

4.) How does Brad think about launching new cities? What does it take to win in those geographies? What are all the necessary parts to setup when entering a new location? What is the biggest determinant of a location success? Density? Maturity?

5.) Brad has assembled a truly world-class exec team, what does Brad think it takes to attract truly A* talent? When should founders really start to think about building out their own exec team? What does Brad believe it is that makes his partnership with Toby Sun work so well? What have been his learnings from the development of that relationship?

Items Mentioned In Today’s Show:

Brad’s Fave Book: Good To Great by Jim Collins

As always you can follow Harry and The Twenty Minute VC on Twitter here!

Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Scott Kupor is Managing Partner @ Andreessen Horowitz, one of the world’s most renowned venture funds with a portfolio including the likes of Facebook, Airbnb, Github, Lyft, Coinbase, Slack and many more. As for Scott, he has been with the firm since its inception in 2009 and has overseen its rapid growth, from three employees to 150+ and from $300 million in assets under management to more than $7 billion today. Before a16z, Scott was a VP @ HP where he managed a $1.5 billion (1,300 person) global support organization for HP Software product portfolio. Scott joined HP as a result of his prior company Opsware, being acquired, where he served as a Senior VP across numerous roles across an incredible 8-year journey. 

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In Today’s Episode You Will Learn:

1.) How Scott made his way from the world of law to startups to being Managing Partner at one of the world’s most renowned venture firms in the form of a16z?

2.) How did seeing the boom and bust of the dot com bubble and 2008 impact Scott’s operating mindset today? Why does he argue that those times are so drastically different to today? How do public markets fundamentally diffferent? How do teams approach to capital efficiency and scaling differ significantly?

3.) What does Scott believe entrepreneurs get most wrong when pitching VCs? Why does Scott argue that product is not the core when pitching VCs? Does Scott agree with Fred @ Okta in weighing it: 70% market, 20% team, 10% product? What is Scott’s weighting? Why does Scott believe that the compression of fundraising timelines is a problem? What pitch sticks out to Scott above all others? What made it so memorable?

4.) How does Scott advise founders on determining the right amount to raise for? Does Scott believe that founders should ask for a specific number or a range? Why does Scott believe raising for “runway” is the wrong mindset? Does Scott believe that most bridges are bridges to nowhere? If so, what is the next step? How does one relay that information to the founders?

5.) What have been some of Scott’s biggest learnings from building the firm with Marc and Ben? What does Scott believe have been the biggest inflexion points in the public status of a16z? What have been the biggest challenges for Scott in the scaling of the firm? How does he foresee that changing in the future?

Items Mentioned In Today’s Show:

Scott’s Fave Book: Master of the Senate: The Years of Lyndon Johnson

As always you can follow Harry, The Twenty Minute VC and Scott on Twitter here!

Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Zach Perret is the Founder & CEO @ Plaid, the startup providing the easiest way for users to connect their bank accounts to an app whether it be transactions, identity or authentication. To date, Zach has raised over $300m with Plaid from some of the best in the business including Mary Meeker, Index Ventures, Andreessen Horowitz, Felicis, Spark and Homebrew, just to name a few. As for Zach, as CEO he has scaled Plaid to today with over 300 employees, 3 international offices and over 10Bn transactions analysed. Prior to founding Plaid, Zach was a consultant @ Bain.

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In Today’s Episode You Will Learn:

1.) How Zach made his way into the world of startups from consulting at Bain and what led to the founding of Plaid and the mission to unlock consumer finance? What advice would Zach give to emerging grads today, questioning whether to join or start a startup?

2.) What does great leadership and CEOship look like to Zach? How has Zach seen himself evolve and develop as a leader over the last few years? How does Zach think about prioritisation? How does Zach determine what to say yes vs what to say no to? What has Zach found the most challenging in scaling as a CEO? What has he done to mitigate this?

3.) How does Zach think about constructing the optimal recruitment process? What have been some of Zach’s biggest lessons in what it takes to really recruit world-class talent? What does Zach mean when he says, “you have to hire for spikes”? How does Zach manage the tension of keeping the high-quality bar whilst also sustaining the very steep growth curve?

4.) Plaid recently raised $275m, how does Zach think about capital efficiency with Plaid today? How does Zach determine when is the right time to transition from the mindset of lean and iteration to raising a war chest and going for the home run? What is Zach’s biggest advice to founders when it comes to investor selection? Is it possible for the investor and the founder to be “friends”?

5.) When assessing the fintech landscape today, what is Zach most excited to see develop over the next 12-18 months? How are we seeing much larger incumbents like Goldman innovate in the proliferated world of fintech startups? How does the US view the fintech innovation that has occurred in the UK? What does this mean for US fintechs?

Items Mentioned In Today’s Show:

Zach’s Fave Book: Hard Drive: Bill Gates and the Making of the Microsoft Empire

As always you can follow Harry, The Twenty Minute VC and Zach on Twitter here!

Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Zach Coelius is Managing Partner @ Coelius Capital and in his own words, “a pretty eclectic investor who loves to see just about any deal”. To date, Zach has made investments in the likes of mParticle, Cruise Automation, Branch Metrics, SkySafe, ProsperWorks and more. In addition, Zach is or has been an advisor to LiveRamp, Hellosign, Art19, Loom.ai, Survata and StartGrid just to name a few. Prior to his investing career, Zach was CEO @ Triggit, an online adtech company which he raised over $18m for and was ultimately acquired in 2015. If that was not enough, Zach is also a Senior Advisor to McKinsey & Co.

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In Today’s Episode You Will Learn:

1.) How Zach made his way from the world of operating and adtech to investing and advising startups today? When does Zach feel the ecosystem really started to take him seriously as an investor? What did Zach learn from being in the adtech space that he has applied to his investing today?

2.) The Future of Venture: Naval has previously said we will see “the unbundling of VC”, does Zach agree with this view? Why does Zach feel we are seeing both the bundling and the unbundling of venture platforms? What unique challenges does this pose for both sides of the equation? How should entrepreneurs evaluate the different options, bundled vs unbundled?

3.) Portfolio Construction: Why does Zach believe that portfolio construction is fundamentally inefficient? What 2 core areas of venture does portfolio construction cause issues for? When does Zach view to be the ideal insertion point if optimising for absolute returns and not following portfolio construction?

4.) Reserve Allocation and Pricing: Why does Zach think that the current mechanism for reserve allocation is broken? Why is it a fundamentally bias process? What does the optimal investment decision-making process look like to Zach? How does Zach think about the asymmetric information that is gained from being early into a company? How can investors really use it to their advantage? Why do they not?

5.) Why does Zach compare being an entrepreneur to being a gladiator and a rocketship? Why does Alex believe the transition from space articulation to product articulation is the most important thing an entrepreneur can do? What is the true sign of this transition in customer interactions? Where do many entrepreneurs make mistakes here?

Items Mentioned In Today’s Show:

Zach’s Fave Book: The Snowball: Warren Buffett and the Business of Life

Zach’s Most Recent Investment: Mud\Wtr

As always you can follow Harry, The Twenty Minute VC and Zach on Twitter here!

Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Kulveer Taggar is the Founder & CEO @ Zeus Living, the startup providing a home of your own for business travel with smartly furnished homes for extended stays. To date, Kul has raised over $14m in VC funding from some dear friends of the show in the form of Garry and Alexis @ Initialized, James and Pete @ NFX, Mike @ Floodgate, Y Combinator, GV and Naval Ravikant just to name a few. Prior to Zeus, Kul co-founded Auctomatic alongside Stripe’s Patrick Collison, they ultimately sold the company for $5m. Before that, Kul co-founded Boso, alongside former 20VC guest, Monzo’s Tom Blomfield, they raised seed funding from YC before moving to the states to start Auctomatic. If that wasn’t enough, Kul has also made several angel investments in the likes of Boom, Airhelp, Meetings.io and more.

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In Today’s Episode You Will Learn:

1.) How Kul made his way from Oxford University to being at the centre of one of tech’s most powerful hubs of YC and then with the founding of Zeus? What were Kul’s biggest takeaways from his first 2 startups? How did that impact his operating mentality?

2.) What did the idea generation process look like for Kul with Zeus? How was James Currier @ NFX so foundational helping here? Why does Kul believe that the idea “really is everything” today? Why does Kul believe that customer acquisition channels are a core part of the product that must be considered from Day 1?

3.) Before hitting on Zeus, Kul and the team had many ideas, what did that idea validation process look like? How did Kul keep morale high in the team when continuously trying and stopping work on new projects? How does Kul think you can use culture as a superpower? As a leader, how can you be both vulnerable and strong at the same time?

4.) Kul has previously said that “tech-enabled businesses are just much harder than pure software plays”. Why is that? What makes them so much more challenging? How do the required skills to be successful change when moving from pure software to tech-enabled? What single question remains the most important to ask when innovating in either?

5.) VCs are not so used to such operationally heavy businesses so how did Kul find the fundraising process? Why does Kul advocate that all founders should speak to investors and A/B test their idea before starting work on it? How did investors differ when comparing SF vs NYC? How did the messaging have to change? What was the most common pushback or concern? What have Initialized done to have such a foundational impact? What makes Garry such a special investor to have on board?

Items Mentioned In Today’s Show:

Kul’s Fave Book: How The Mind Works by Steven Pinker

As always you can follow Harry, The Twenty Minute VC and Kul on Twitter here!

Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Geoff Ralston is President @ Y Combinator, the world’s leading accelerator with a portfolio that includes the likes of Stripe, Airbnb, Dropbox, Coinbase, Instacart, DoorDash, Flexport and so many more. As for Geoff, he started his career running engineering at Four11, where he built RocketMail, which in 1997 became Yahoo! Mail. At Yahoo! Geoff worked in engineering, then ran a business unit, then became Chief Product Officer. After Yahoo! he was CEO of Lala, which was acquired in 2009 by Apple. Post Lala, Geoff then co-founded the world’s first educational technology accelerator, Imagine K12 which funded dozens of edtech companies including ClassDojo, Remind, and Panorama Education. Imagine K12 merged with YC in 2016.

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In Today’s Episode You Will Learn:

1.) How Geoff made his way into the world of technology and startups, came to found Imagine K12 and how that led to becoming President @ Y Combinator today?

2.) What were Geoff’s biggest takeaways from seeing the boom and bust of the macro environment in the dot com and 2008? How did those times impact both his operating and investing mentality? Why does Geoff believe 2000 was “purifying”? Why can the same not be said for 2008? How was 2008 so different?

3.) Frederic Kerrest @ Okta said: “it is 70% market, 20% team and 10% product”, would Geoff agree with this weighting? How has his weighting changed over time? YC has “10 Minute Meetings”, how can YC really determine whether someone is investable in 10 mins? How does Geoff think about the hailed VC term, “pattern matching”? Why does Geoff believe you lose as an investor if you fall back on “profiles”?

4.) Geoff has worked with 100s of founders in the idea validation stage, how does Geoff know when a founder has the right idea? How does Geoff think about the balance between mission and vision but then also being realistic about when something is not working? When do you quit? Why is the decision internal not external? What is the most important perspective any investor can give a founder?

5.) How does Geoff think about the coined term “product-market fit” and how does he analyse it in terms of retention and growth? If they have some signs of it, how should founders think about when is the right time to raise their first round? How does Geoff think about the benefits for founders of convertibles and now SAFE’s? What does Geoff believe will be the future of legal round mechanics?

Items Mentioned In Today’s Show:

Geoff’s Fave Book: Titan: The Life of John D. Rockefeller

As always you can follow Harry, The Twenty Minute VC and Geoff on Twitter here!

Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Mathilde Collin is the Co-Founder & CEO @ Front, reinventing the email inbox with new workflows and efficient collaboration so people can accomplish more together. To date, Mathilde has raised over $79m in VC funding with Front from some of the best in the business including Bryan Schreier @ Sequoia, Initialized, Uncork Capital, Boldstart and individuals including Andrew Chen, Elad Gil, Ray Tonsing the list goes on. With 4,500+ customers, and 100+ employees, in Paris, San Francisco and Amsterdam, Front is one of the fastest growing companies in SaaS and Mathilde has become a thought leader for the next generation of SaaS CEOs, read more on her blog here. 

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In Today’s Episode You Will Learn:

1.) How Mathilde made her way from product manager in Paris to founding one of the hottest and fastest growing companies in the world of SaaS in the form of Front?

2.) What does Mathilde mean when she says, “I would choose discipline over vision any day of the week”? What does discipline really mean to Mathilde? Why is it a priority in the early days? How can a VC stress test and determine the level of discipline a founder has in first meetings? What are the signs or leading indicators?

3.) Communications:

• Investor Updates: What is Mathilde’s biggest advice to founders when it comes to investor updates? What should they contain? How often should they go out? How should founders ask for help in updates? Where do founders often make mistakes?
• Revenue Updates: Why does Mathilde do revenue updates with the team? Is there a danger of being too transparent? What are the benefits of this transparency? What is the structure of the update? Who is privy to it?
• Direct Reports: How does Mathilde communicate with her direct reports? Why does Mathilde believe that CEOs should have their calendar public? What is the right cadence for these direct reports?

4.) How does Mathilde approach and think about fundraises with Front today? How can founders know when is the right time to raise? How does Mathilde think about building relationships with investors when she is not raising? How transparent should founders be when they are not raising? What are Mathilde tips for always overshooting her numbers? How does Mathilde conduct DD on potential investors in the company?

Items Mentioned In Today’s Show:

Mathilde’s Fave Book: The Power of Now: A Guide to Spiritual Enlightenment

As always you can follow Harry, The Twenty Minute VC and Mathilde on Twitter here!

Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

 

 

 

Jeff Housenbold is a Managing Partner @ Softbank Vision Fund, the leading and most influential firm in the venture space investing more than $93 billion in the businesses and technologies they believe will enable the next stage of the information revolution. To date, Jeff has backed the likes of OpenDoor, DoorDash, Wag, Clutter, Brandless and Katerra just to name a few. Prior to Softbank, Jeff spent 11 years as President and CEO @ Shutterfly, during his tenure the company enjoyed incredible growth with the growth of the team from 103 to 2,600 employees. In the past, Jeff has sat on the board of Caesers Entertainment (the world’s largest casino entertainment company), Groupon and Chegg and is currently a member of the Board of Trustees of Carnegie Mellon University.

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In Today’s Episode You Will Learn:

1.) How Jeff made his way from being President and CEO of Shutterfly for 11 years to writing $200m-2Bn checks as Managing Partner @ Softbank Vision Fund?

2.) We have Wag on the small end and Uber on the high end, so how does Softbank think about portfolio construction and insertion point today? Blended, at what stage would Softbank like their capital to be most concentrated? Does Jeff believe that ownership is largely built on the first check or built over time?

3.) What does the internal investment-decision making process look like for Softbank? How does this decision-making process change when considering reserve allocation? How does Softbank think about and approach reserves given their later entry into companies? Given the size of check being written, what does diligence look like in the standard process for Softbank?

4.) Given the forthy pricing environment today, how does Jeff assess his own price sensitivity? Does this differ depending on the stage of entry? With many suggesting Softbank have extended the period of privatisation for companies, how does Jeff and the team think about liquidity? How does Jeff think about the future of secondaries for seed managers and angels?

5.) Question from Eric Wu @ Opendoor: How does Jeff think about and analyse the opportunity in fragmented categories? What is the bottoms up thought process to this thesis? Speaking of Opendoor, how does Jeff most like to work with the founders he backs? How does Jeff think about he allocates his time across the portfolio?

Items Mentioned In Today’s Show:

Jeff’s Fave Book: The Fountainhead

Jeff’s Most Recent Investment: Katerra

As always you can follow Harry, The Twenty Minute VC and Jeff on Twitter here!

Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Want to book your own travel and not have the admin team chasing you for every receipt? Take your business travel program to the next level with TravelPerk. They’ve built the world’s largest inventory of low-cost flights, hotels, airbnb, trains, cars, you name it, all in one gorgeous booking experience. AND they’re built for business. Book, manage, support, analyze, and optimize your business travel, all in one place. Add to this a support team made up of dedicated travel experts who deliver a 7-star experience around the clock, and you’re taking corporate travel out of the dark ages. 20VC listeners can score a free lounge pass to over 1200 airports for a whole year. Not only will you be able to add “company savior” to your email signature, but you can also enjoy the luxury of amazing airport lounges all over the world. Click here to find out more!

Jon Dishotsky is the Founder & CEO @ Starcity, the startup on a mission to make cities more affordable to everyone allowing you to live with great people in the city you love. To date, Jon has raised over $28m in funding for Starcity from the likes of Social Capital, Y Combinator, Bullpen Capital, NEA and Kima Ventures in Paris, just to name a few. Prior to founding Starcity, Jon did over 3M square feet of commercial real estate transactions for clients including Optimizely, Cruise Automation, Weebly, Zenefits and many more. Before that he spent 8 years at the prestigious Cushman & Wakefield. Jon is also an active angel investor with investments in the likes of Remote, Fond and Savvy.

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In Today’s Episode You Will Learn:

1.) How Jon made his way from doing real estate transactions for clients including YC to being one of the hottest prop tech startups making cities affordable with Starcity?

2.) Why did it take so long for the venture ecosystem to get excited by the rise of proptech? What was the catalyst? When advising VCs, how do you advise them to get comfortable investing in these heavy asset, non-lean startup businesses? What are the biggest mistakes investors make when analysing proptech?

3.) What were some of Jon’s biggest takeaways from his time at YC? How does Jon advise other founders looking to get into YC today? When it comes to investor selection, in what cases would Jon take a lower valuation against other offers? How does Jon advise founders on investor selection? What questions should they ask? Why is it like hiring? What are the common mistakes that Jon sees founders make when selecting investors?

4.) How does Jon advise founders when it comes to improving the quality of their mental health? Where do Jon struggle? How does Jon engage with social media knowing the psychological effects it has? What have been some major breakthroughs for him? Why does Jon believe having kids has made him a better founder? Why does Jon believe that older entrepreneurs are actually more successful than younger founders?

5.) What is Jon’s biggest advice to founders when it comes to building relationships with VCs? Should founders “always be raising”? How transparent should founders be with VCs both in the relationship building process and the fundraise itself?

As always you can follow Harry, The Twenty Minute VC and Jon on Twitter here!

Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

 

Mamoon Hamid is a Partner @ Kleiner Perkins, one of Silicon Valley’s most prestigious venture firms counting Google, Airbnb, Amazon, Spotify, Square and many more $Bn companies among their portfolio. As for Mamoon, he has invested in and served on the boards of some of the most innovative software companies of recent times including Box, Figma, Intercom, Netskope, Slack and Yammer. Prior to joining Kleiner Perkins, Mamoon was a Co-Founder and General Partner at Social Capital and before that Mamoon was a Partner at U.S. Venture Partners (USVP), where he spent six years.

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In Today’s Episode You Will Learn:

1.) How did Mamoon make the transition from electrical engineer to VC and how did that translate to his role today as Partner @ KPCB?

2.) With Kleiner’s new $600m early stage fund, Mamoon had a blank canvas, how does Mamoon think about portfolio construction from a bottom-up perspective? Why is that strategy optimal? How important does Mamoon believe it is for VCs to have a sector focus today? What does he mean when he says, “VCs need to have both majors and minors”?

3.) In today’s heated early stage ecosystem, how does Mamoon analyse and reflect on his own price sensitivity? What deal has changed the way he thought about price and he either regrets not paying it or is thrilled he did pay it? How does Mamoon feel about the compressed fundraising timelines we are seeing today? Is this a concern?

4.) How does KPCB think about reserve allocation with the new $600m fund? How do they approach the opportunity cost of dollar deployment in terms of when to stop following on? How does the investment decision-making process change when comparing initial to reserve investment?

5.) Where does Mamoon believe that founders need the most help from their venture investors? Where does Mamoon see the commonalities in founders struggles to scale themselves with their role? What are the biggest mistakes Mamoon sees being made when initial traction has been hit and they start to scale? How can founders avoid these?

6.) How does Mamoon think about and address what it takes to build the most successful and efficient venture partnership? How does Mamoon compare this to a basketball team? Is venture really a team sport today? what are some of the biggest challenges in scaling venture firms over time?

Items Mentioned In Today’s Show:

Mamoon’s Fave Book: Principles: Life and Work by Ray Dalio

Mamoon’s Most Recent Investment: Viz.ai

As always you can follow Harry, The Twenty Minute VC and Mamoon on Twitter here!

Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Michele Romanow is the Founder & CEO @ Clearbanc, the startup that provides entrepreneurs capital to grow without giving up a piece of their company. In 2019 alone, Clearbanc plans to invest $1B in 2,000 companies. To fund these ambitious plans, they have backing from some of the best in the business including Founders Fund, Santi @ Emergence, Social Capital, Precursor Ventures and Y Combinator just to name a few. As for Michele, prior to Clearbanc, she founded SnapSaves, a leading mobile savings platform that was acquired by Groupon. Before Snapsaves, Michele founded Buytopia, one of Canada’s leading e-commerce companies with over 2.5m customers. If that was not enough Michele is also a Dragon on Dragons Den Canada, the youngest dragon ever.

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In Today’s Episode You Will Learn:

1.) How Michele made her way from serial entrepreneur with exits to Groupon and being a Dragon on Dragons Den to changing the way we fund today’s businesses with Clearbanc?

2.) Why does Michele fundamentally believe we need to rethink the way we fund our businesses? Why does giving away equity to buy FC and Google ads not make sense? What is the solution? What types of business with what types of revenue does this work for? Why does Michele believe we need to fundamentally stop celebrating fundraisings?

3.) So if Clearbanc lends on repeatable revenue from Google and Facebook, how does Michele think about the volatility of CACs we see as businesses progress? Is Michele concerned by the large incumbents pushing up CACs on traditional platforms? Investors can also be wise strategic advisors, how does Michele think about the potential loss of these advisors and board members with an alternative financing mechanism?

4.) From Clearbanc’s data, what have been the big learnings on how venture is currently distributed across the US? To what extent does Michele believe that unconscious bias pervades into the decision-making of much of venture? What have Clearbanc discovered in terms of the diversity of the founders they back, purely through objective data analysis of their businesses?

5.) How does Michele respond when shit hits the fan? What is her coping mechanism? How would Michele advise young founders today in coping with tough times? What were Michele’s lessons from her first sturgeon caviar business not being a success?

Items Mentioned In Today’s Show:

Michele’s Fave Book: Little Black Stretchy Pants

As always you can follow Harry, The Twenty Minute VC and Michele on Twitter here!

Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Want to book your own travel and not have the admin team chasing you for every receipt? Take your business travel program to the next level with TravelPerk. They’ve built the world’s largest inventory of low-cost flights, hotels, airbnb, trains, cars, you name it, all in one gorgeous booking experience. AND they’re built for business. Book, manage, support, analyze, and optimize your business travel, all in one place. Add to this a support team made up of dedicated travel experts who deliver a 7-star experience around the clock, and you’re taking corporate travel out of the dark ages. 20VC listeners can score a free lounge pass to over 1200 airports for a whole year. Not only will you be able to add “company savior” to your email signature, but you can also enjoy the luxury of amazing airport lounges all over the world. Click here to find out more!

Brendan Wallace is the Co-Founder and Managing Partner @ Fifth Wall, the fund with the core thesis being the physical world around us is colliding with technology. Within their portfolio is the likes of Lime, OpenDoor, Clutter, ClassPass, Lyric and Hippo just to name a few. As for Brendan, before co-founding Fifth Wall he co-founded Identified, a data & analytics company focused on workforce optimization that was acquired by Workday in 2014. Prior to that, Brendan co-founded Cabify, the largest ridesharing service in Latin America. If that was not enough, Brendan has been an active angel investor having led over 60 angel investments including Bonobos, Dollar Shave Club, Lyft, SpaceX, Clutter, Philz Coffee and Zenefits.

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In Today’s Episode You Will Learn:

1.) How Brendan made his way from founding the largest ridesharing platform in Latin America to changing the face of early stage real estate and consumer retail investing with Fifth Wall?

2.) What is really going on in retail today? Is “retail apocalypse” a fair term to give to the landscape today? What formats does physical retail no longer work for? What is it perfect for? How does Brendan think about the distribution of physical retail for emerging brands? Will they need 1,000s of stores or is the 1,000 store brand era over?

3.) Why do digitally native brands fundamentally need retail? How much of consumer US spend relies on physical retail still today? When do these DNVB’s need to expand into physical retail? From speaking to DNVB CEO’s what are the most common challenges they face when making the expansion?

3.) How does expanding into physical retail change the game in terms of customer acquisition for DNVBs? At what point do DNVBs hit the invisible asymptote where acquiring customers through traditional online channels is no longer efficient? How have Amazon impacted the CACs for DNVBs in recent years?

4.) Given the consumer retail focus of the fund, one would expect a lower loss ratio, is it right to assume the lower loss ratio? How does Brendan think about portfolio construction with the fund? How does reserve allocation differ when investing in physical retail vs pure software plays? Is Brendan concerned by the lack of downstream capital in the physical retail space?

5.) How does Brendan assess outcome potential when comparing physical retail to pure software plays? Why des Brendan believe we will see a ton of intermediate outcomes? How does this change the type of entrepreneur that Brendan looks to back with the retail fund?

Items Mentioned In Today’s Show:

Brendan’s Fave Book: The Great Gatsby

Brendan’s Most Recent Investment: Heyday

As always you can follow Harry, The Twenty Minute VC and Brendan on Twitter here!

Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Want to book your own travel and not have the admin team chasing you for every receipt? Take your business travel program to the next level with TravelPerk. They’ve built the world’s largest inventory of low-cost flights, hotels, airbnb, trains, cars, you name it, all in one gorgeous booking experience. AND they’re built for business. Book, manage, support, analyze, and optimize your business travel, all in one place. Add to this a support team made up of dedicated travel experts who deliver a 7-star experience around the clock, and you’re taking corporate travel out of the dark ages. 20VC listeners can score a free lounge pass to over 1200 airports for a whole year. Not only will you be able to add “company savior” to your email signature, but you can also enjoy the luxury of amazing airport lounges all over the world. Click here to find out more!

Frederic Kerrest is the Founder & COO @ Okta, the independent and neutral platform that securely connects the right people to the right technologies at the right time. To date Frederic has raised over $415m with Okta from some of the best in the business including Doug Leone @ Sequoia, Marc Andreessen @ a16z, a dear friend of the show in Mike Maples @ Floodgate, Aneel Bhusri @ Greylock and Vinod Khosla, just to name a few. Okta IPO’d in April 2017 at a stock price of $17, today they sit at $102. Before founding Okta, Frederic enjoyed roles with Hummer Winblad on the other side of the table as a VC and also at Salesforce and Sun Microsystems on the operations side.

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In Today’s Episode You Will Learn:

1.) How Frederic came to found the now public Okta having spent time with Salesforce, Sun Microsystems and Hummer Winblad as a VC?

2.) What about an idea makes it worth pursuing and investing in? Does Frederic agree with the advice he was given, “it is 70% market, 20% people and 10% product”? When evaluating a market, what characteristics make for the most attractive markets? How does Frederic think about insertion points into markets? How does he evaluate market adjacencies? Why is it so good to be a monopolist in a small market?

3.) What were some of the hardest times Okta went through? How does Frederic determine the balance between vision and realism? How does Frederic as the leader personally deal with these challenging times? How can a founder determine from their hiring process whether they have product-market fit? What were the key turnings points that contributed to Okta’s success? What did you have to get right to keep scaling?

4.) A little birdy told me there was an amazing story behind the a16z investment, what is that story? How did Frederic meet Marc and Ben and how did his relationship with them evolve over time? When analysing his investor base, where did each add real strategic value? What advice does Frederic give to founders today on the theme of investor selection? What should the core considerations be?

Items Mentioned In Today’s Show:

Frederic’s Fave Book: Battle Cry of Freedom: The Civil War Era

As always you can follow Harry, The Twenty Minute VC and Frederic on Twitter here!

Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Want to book your own travel and not have the admin team chasing you for every receipt? Take your business travel program to the next level with TravelPerk. They’ve built the world’s largest inventory of low-cost flights, hotels, airbnb, trains, cars, you name it, all in one gorgeous booking experience. AND they’re built for business. Book, manage, support, analyze, and optimize your business travel, all in one place. Add to this a support team made up of dedicated travel experts who deliver a 7-star experience around the clock, and you’re taking corporate travel out of the dark ages. 20VC listeners can score a free lounge pass to over 1200 airports for a whole year. Not only will you be able to add “company savior” to your email signature, but you can also enjoy the luxury of amazing airport lounges all over the world. Click here to find out more!

Sarah Smith is a Partner @ Bain Capital Ventures, a leading US venture fund with a portfolio that includes the likes of LinkedIn, Lime, SendGrid, Jet.com and more incredible companies. As for Sarah, what a start she has had to her time at Bain leading investments in the likes Perksy and the unicorn that is Lime. Prior to joining Bain, Sarah spent 5 years at Quora both as VP of Advertising Sales and Operations and then also from 2012-2016 as VP of HR, Recruiting, and Operations scaling the company from 40 to 200 employees. Before Quora, Sarah spent 4 years at Facebook as Director of Online Operations where her team scaled revenue to $1 billion ARR while reducing churn and increasing customer satisfaction.

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In Today’s Episode You Will Learn:

1.) How Sarah made her way into the world of venture having seen the hyper-growth of both Facebook and Quora over 9 years in operations? What were the biggest takeaways from her time with Facebook and Quora? What lessons did Sarah learn as an elementary school music teacher that she has applied to her role in VC?

2.) Sarah and Bain led the Series D in Lime, so how does Sarah think about:

• Market Size: How did Sarah think about and assess market size when evaluating Lime? How does Sarah respond to Peter Fenton’s statement, “I always laugh when I hear investors say they look for big markets”?
• Competition: How did Sarah look to get comfortable entering such a fiercely competitive space? Is capital itself a defensible moat?
• Dilution: With such huge future funding requirements for these companies, how did Sarah get comfortable with the level of dilution that will surely occur?
• Hardware & Unit economics: How does Sarah think about and respond to the current level of break rates? How does Sarah believe Lime can have positive unit economics within 18 months?

3.) Why does Sarah believe that engineers are fundamentally underpaid? How does this tie into their mindset and attitude to equity? Why does Sarah believe the 4-year vesting schedule is fundamentally outdated? What would Sarah advise founders in terms of comp package to put in it’s place? Does Sarah believe the high attrition rate in the valley is a feature or a bug?

4.) Why does Sarah believe it is glib to say the lack of equality is merely the problem of VC being an old boy club? What are the more foundational and systemic problems that have caused this inequality? Why does GP commit fundamentally inhibit diversity? For firms looking to add a female partner, what is their literal next step? What does that process look like? What can they do to ensure their success in the first year? Where does Sarah see many firms going wrong here? What must firms avoid?

Items Mentioned In Today’s Show:

Sarah’s Fave Book: Brotopia: Breaking Up the Boys’ Club of Silicon Valley, The Making of a Manager: What to Do When Everyone Looks to You

Sarah’s Most Recent Investment: Perksy

As always you can follow Harry, The Twenty Minute VC and Sarah on Twitter here!

Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Want to book your own travel and not have the admin team chasing you for every receipt? Take your business travel program to the next level with TravelPerk. They’ve built the world’s largest inventory of low-cost flights, hotels, airbnb, trains, cars, you name it, all in one gorgeous booking experience. AND they’re built for business. Book, manage, support, analyze, and optimize your business travel, all in one place. Add to this a support team made up of dedicated travel experts who deliver a 7-star experience around the clock, and you’re taking corporate travel out of the dark ages. 20VC listeners can score a free lounge pass to over 1200 airports for a whole year. Not only will you be able to add “company savior” to your email signature, but you can also enjoy the luxury of amazing airport lounges all over the world. Click here to find out more!

David Rogier is the Founder & CEO @ Masterclass, the startup that brings you online classes taught by the world’s greatest minds including Steve Martin, Natalie Portman, Margaret Attwood and more. To date, David has raised over $140m in funding for Masterclass from the likes of IVP, NEA, Javelin, Michael Dearing @ Harrison Metal, Atomico and past guests of the show Sam Lessin and Philip Krim. As for David, prior to founding Masterclass, he was on the other side of the table as an investor with Harrison Metal. Before venture, David spent time with IDEO helping to create new consumer products and brands.

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In Today’s Episode You Will Learn:

1.) How David made his way into the world of startups? How a lesson from his grandmother when he was only 7 shaped the type of company David wanted to build?

2.) David has previously said, “as a founder, you have one job”. What is that job? How does David think about how raising VC changes outcomes? Why does David think many founders approach fundraising the wrong way? What questions must founders always ask a VC pre-term sheet? How can founders do their work and diligence on the VC?

3.) Why does David try at all costs to not send the deck to the VC ahead of meeting? Why can this be damaging? How can founders say no politely? Does David agree with the conventional wisdom that “founders must always be raising”? What is the optimal way to structure relationship building with investors?

4.) What does David mean when he says, “pick your investors as board members, not investors”? What does David believe makes the truly special board members? What were David’s biggest learnings from Michael Dearing @ Harrison Metal when it comes to boards? What does David believe are big red flags in potential future board members?

5.) When validating the idea and the product, how does David think founders should use testing to prove their thesis at every stage of the business? Why, if proved, does this automatically secure your funding for the next round? What do VCs like to see in this testing? How does David think about when is the right time to go and raise big?

Items Mentioned In Today’s Show:

David’s Fave Book: Creativity Inc

As always you can follow Harry, The Twenty Minute VC and David on Twitter here!

Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Jeremy Liew is a Partner @ Lightspeed Venture Partners, one of the leading firms of the last decade with a portfolio including the likes of Snapchat, Mulesoft, Max Levchin’s Affirm, AppDynamics and many more incredible companies. As for Jeremy, he is best known for being the 1st investor in Snapchat and has also led investments in StitchFix, Affirm, Ripple, Giphy and Bonobos just to name a few. Previously, Jeremy was with AOL, first as SVP of corporate development and chief of staff to the CEO, and then as general manager of Netscape. Due to his incredible investing success, Jeremy has been featured on the Forbes Midas List multiple times.

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In Today’s Episode You Will Learn:

1.) How Jeremy made his way into the world of venture with Lightspeed and came to be one of the valley’s leading consumer investors and minds?

2.) How does Jeremy think about and approach sourcing today? How has mindset on sourcing shifted over the last decade? For a new VC, what would Jeremy advise them in terms of building them benchmark for distinguishing between good and great? How does Jeremy distinguish between good and great? Who does Jeremy believe is the most naturally gifted sourcer and hunter he has worked with?

3.) What does Jeremy mean when he says, “it is more important to be right than contrarian”? From winning some of the hottest deals, what have been Jeremy’s lessons on what it takes to win the most competitive? What does he mean when he says, “you have to find your home advantage”? Should investors spend time amplifying their strengths or improving their weaknesses? How does Jeremy think about the round compression timelines on hot deals today? How can investors and founders build relationships fast?

4.) Why does Jeremy believe that founder to VC engagement can be similar to a driving instructor and student? What are the biggest mistakes startups make when they hit initial traction and start to scale? What patterns has Jeremy seen? How can founders avoid them?

5.) How does Jeremy fundamentally structure his week and time? What time is devoted to internal meetings and partnership meetings? How much time is allocated to the existing portfolio? How much time is spent with new prospective companies? What is Jeremy’s favourite and least favourite activities within the role?

As always you can follow Harry, The Twenty Minute VC and Jeremy on Twitter here!

Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Dylan Field is the Founder & CEO @ Figma, the startup that provides a better way to design, prototype and collaborate, all in the browser. To date, Dylan has raised over $82m in funding from some of the world’s best investors including Sequoia, Greylock, Kleiner Perkins, Founders Fund, Index Ventures and more. Prior to changing the world of design with Figma, Dylan held roles at Flipboard, Microsoft and LinkedIn and was part of the renowned Thiel Fellowship.

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In Today’s Episode You Will Learn:

1.) How Dylan made his way from Thiel fellow to changing the world of design and prototyping with Figma?

2.) What is the story behind the 4-year journey to the launch of their first product? How did Dylan maintain morale with such an extended window between creation and launch? What are the core challenges of building tools companies and getting initial traction? How did Dylan satiate VCs desire for fast growth with such a long period to launch? Is it possible to “go slow to go fast” with VC dollars?

3.) Sequoia led Figma’s Series C, how did the round come together? What was it that made Dylan choose the lead investors for each of his rounds? How did this round compare to prior rounds led by Index, Kleiner and Greylock? How does Dylan advise founders to build relationships of trust and transparency with their VC in short period of time?

4.) How did Dylan approach the topic of board construction? What did he most want to get out of his board? What have been some of Dylan’s biggest learnings when it comes to board management? What has Dylan found the most challenging element?

5.) As a young founder himself, where does Dylan see commonalities in the mistakes that other young founders make today? As a young founder, how has Dylan been able to hire A** talent execs? What have been some of the biggest learnings on team assembly and construction through the process?

Items Mentioned In Today’s Show:

Dylan’s Fave Book: Stronger, Faster, and More Beautiful

As always you can follow Harry, The Twenty Minute VC and Dylan on Twitter here!

Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Dave Sobota is the Vice President of Corporate Development @ Instacart, the company that delivers your groceries in as little as 1 hour. To date the company has raised over $1.9Bn in funding from some of the very best investors and operators including Mike Moritz @ Sequoia, Jeff Jordan @ a16z, Aaron Levie @ Box, Sam Altman, Garry Tan and more incredible names. As for Dave, prior to Instacart, he was Director of Corporate Development @ Google for over 10 years and before that was with leading law firm, Wilson Sonsini.

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In Today’s Episode You Will Learn:

1.) How Dave made his way from the world of law to Director of Corporate Development at Google to his position at Instacart today?

2.) In 2016, we had 513 BC backed exits, 499 were M&A, so how does Dave assess the M&A landscape today? Why id Dave bullish on the future M&A environment, at least for the next 12 months? Where are his concerns around M&A clustering? How does Dave view the entrance of large scale PE into the tech M&A arena?

3.) From leading Google’s M&A practice, what have been Dave’s core learnings on whether an entrepreneur should sell their company or remain independent? Paul Graham once said, “startups only talk to corp dev when they are doing really well or really badly”. Does Dave agree? What are the reasons a startup would not speak to corp dev? What is the right way for them to communicate this while leaving the door open for future conversations?

4.) How does Dave operationalise the tracking of the startup market and determine what startups he wants to meet? How does Dave like to and think about working with the VC community here? What does that relationship building process look like? In those early meetings, what are the core questions that founders must ask? How much of a role does price play for Dave when considering an acquisition?

5.) How can founders ensure when they sell their company, that it will be properly integrated? What answers from the acquirer suggest it will or will not be? From countless M&A processes, what do the best integrations look like post-acquisition? Where are mistakes often made? Does Dave agree with Paul Graham in stating it is a “gruelling” process?

Items Mentioned In Today’s Show:

Dave’s Fave Book: Lonesome Dove

Dave’s Most Recent Acquisition: Tenor

As always you can follow Harry and The Twenty Minute VC on Twitter here!

Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Henry Ward is the Founder & CEO @ Carta, the startup that helps private companies, public companies, and investors manage their cap tables, valuations, investments, and equity plans. To date, Henry has raised over $147m in funding from some of the industries leading investors in USV, Spark, Menlo, K9 Ventures and Meritech and then also leading founders including Flexport’s Ryan Petersen, Transferwise’s Taavet Hinrikus and Slack’s Stewart Butterfield. Prior to founding Carta, Henry was Founder of SecondSight, a portfolio optimization platform for retail investors.

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In Today’s Episode You Will Learn:

1.) How Henry made his way into the world of startups and came to found the gamechanger of cap tables and valuations with Carta?

2.) What does Henry mean by the term “executive half-life”? How does Henry determine between an exec that can scale with the company and an exec that cannot? What are the leading indicators? When weaknesses are revealed, how does this manifest itself? Does the exec open up and admit to it or does the leadership team have to be proactive?

3.) Question from Manu @ K9: As a first time CEO, what have been the biggest personal challenges for Henry in the scaling of himself? Why does Henry think it is unfair founders are given exemption from blame in scaling but execs are not? How does Henry make decisions differently now to the early days? What have been the improvements?

4.) How does Henry buck the conventional wisdom with his willingness to go after very small markets? What does the N of 1 vs 1of N rule mean here? Why does Henry believe the N of 1 markets is the most attractive? What are the core advantages to owning your market? How can founders think about insertion points? When is the right time to add additional products? How does Henry respond to the traditional notion of “focus”?

5.) Why does Henry believe most founders are afraid to put investors to work? If fundraising is, as Henry suggests “an auction process”, what can founders do to optimise it? How does Henry approach the element of value creation and value extraction? How does this influence his approach to pricing? How does Henry think more tech founders can leverage acquiring services businesses and automating their processes over time? Where is the arbitrage in pricing here?

Items Mentioned In Today’s Show:

Henry’s Fave Book: The Essays of Warren Buffett: Lessons for Corporate America

As always you can follow Harry, The Twenty Minute VC and Henry on Twitter here!

Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Dayna Grayson is a Partner @ NEA, one of the leading venture firms over the last 4 decades with a portfolio including the likes of Opendoor, Jet.com, Uber, WorkDay, Plaid, Box and many more incredible companies. As for Dayna, she has led the firm’s investments in the likes of Desktop Metal, Formlabs, Onshape, Glamsquad, Framebridge and Curalate, just to name a few. Prior to joining NEA, Dayna was an investor at North Bridge Venture Partners where she championed companies including Camiant (acquired by Tekelec) and Tapjoy. Before venture Dayna was an engineer at Eye Response Technologies, later acquired by Dynavox Mayer-Johnson and also a product designer at Blackbaud (BLKB), the leading global provider of software to nonprofit organizations.

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In Today’s Episode You Will Learn:

1.) How Dayna made her way into the world of venture and came to be a Partner at NEA from her roots in product design and engineering?

2.) Sourcing: How does Dayna approach the sourcing component of venture today? What does the deck filtering process look like to Dayna, prior to meeting? What has Dayna found works best in really building rapport in the first meetings? What does the conviction building process look like for Dayna from there? If negative, how has Dayna found is the most effective way to say no?

3.) Decision-Making: How does Dayna think about optimising the investment decision-making process? How does Dayna balance between data vs gut? Does NEA require unanimous decision-making? Why does Dayna believe that at A or earlier, the price really does not matter? When does price really become a big issue?

4.) Evolution of Expectations: How does Dayna believe entrepreneurial expectations of VC has changed over the last decade. Where does Dayna believe investors can really provide the most value? Which board member has been the most impressive to Dayna when sitting alongside them on the board? Why?

Items Mentioned In Today’s Show:

Dayna’s Fave Book: Dopesick: Dealers, Doctors and the Drug Company that Addicted America

Dayna’s Most Recent Investment: WireWheel

As always you can follow Harry, The Twenty Minute VC and Dayna on Twitter here!

Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

 

Jeff Russakow is the CEO @ Boosted, the startup producing vehicle grade electric skateboards rethinking how we travel. To date, they have raised $74m in funding from the likes of Khosla Ventures, iNovia Capital, Andreessen Horowitz and our friends at Initialized. Prior to Boosted, Jeff was CEO @ Gimbal where he doubled revenue in his first year and added 80 new enterprise clients. Before that, Jeff was the CEO @ Findly where he grew the company to 450 employees and 20m end users. Jeff also enjoyed prior roles with the likes of Symantec, Adobe, SAP and Yahoo.

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In Today’s Episode You Will Learn:

1.) How Jeff made his way from leading enterprise CEO to re-thinking the way we travel today as CEO of Boosted?

2.) How does Jeff analyse the current sentiment to fundraising in the valley, specifically with regards to business construction? How has Jeff seen the investor class fundamentally transition over the last 20 years? When approaching investor selection, what is the 1 question that Jeff always asks? Where do founders often make mistakes here?

3.) Having raised the $60m round in 2018, how does Jeff approach the theme of capital efficiency today with Boosted? How does Jeff determine when is the right time to pour fuel on the fire? Why is Series B often the most challenging phase when considering the focus on unit economics and vision simultaneously?

4.) What is Jeff’s gut reaction to the statement, “hardware is hard”? Why does Jeff feel this to be a glib statement that misses the point? How does Jeff respond to the criticism of the commodity element of hard, easy to replicate and copy? How would Jeff like to see the investor class change their mindset to hardware? What is the right way to approach it?

5.) What are the core elements required for a successful CEO transition? For a potentially incoming CEO, what must they be wary of with regards to the information conveyed to them by investors of the company? Where has Jeff seen many go wrong in CEO transitions? What can the founders do to make this process as smooth as possible?

Items Mentioned In Today’s Show:

Jeff’s Fave Book: The Missing Piece 

As always you can follow Harry and The Twenty Minute VC on Twitter here!

Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

 

 

Garry Tan is the Co-Founder and Managing Partner @ Initialized Capital, one of the West Coast’s leading early-stage funds with a portfolio including the likes of Coinbase, Instacart, Cruise, Flexport and Opendoor, just to name a few. As for Garry, before co-founding Initialized, he was a partner at Y Combinator for nearly five years where he advised and funded over 600 companies. He was also co-founder of YC-backed blog platform Posterous (acquired by Twitter in 2012). Before that he was employee #10 at Palantir, where he was a founding member of the engineering team for Palantir’s financial analysis product, and also fun fact, Garry designed Palantir’s logo.

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In Today’s Episode You Will Learn:

1.) How Garry made his way from Founder and YC Partner to managing over $500m AUM today with his leading of Initialized? How did Garry’s investment mindset change with the transition from angel to an institutional investor?

2.) What does Garry believe is the one thing pre-seed and seed investors must do that is more important than anything else? What relationship to the very best founders have with failure? How do they think about and approach it? How has Garry seen his own conviction building process in founders change over time? How does Garry approach the turning down of opportunities? What is the right way to deliver that feedback?

3.) Ownership: Initialized’s funds have scaled from Fund I being $7m to Fund 4 being $225m, how have their ownership requirements changed with the evolution of their fund size? How does Garry think about collaboration and co-opetition with others funds as a result? What are the core challenges here?

4.) Price Sensitivity: With the larger fund and slightly more flexibility, how does Garry evaluate his own price sensitivity? What deal has Garry passed on due to price and it has stuck with him and taught him a valuable lesson? On pricing, how does Garry and Initialized approach reserve allocation?

5.) Investment Decision-Making: Garry has previously said “decision-making is a differentiator”, what do Initialized do to ensure the highest quality of internal discussion and decision-making? How do they approach unanimous vs single partner decision-making? How does Initialized approach internal attribution with this in mind?

Items Mentioned In Today’s Show:

Garry’s Fave Book: Peter Thiel’s Zero To One, Paul Graham’s Hackers and Painters

Garry’s Most Recent Investment: Standard Cognition

As always you can follow Harry, The Twenty Minute VC and Garry on Twitter here!

Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

 

Joel Gascoigne is the Co-Founder & CEO @ Buffer, the social media management tool that makes it easy for businesses and marketing teams to schedule posts, analyze performance, and manage all their accounts in one place. They had raised both seed and Series A rounds but last summer, spent $3.3m to buy out the majority of their Series A investors, making them much more independent. Joel now runs Buffer as a profitable business with $2m in profit in 2017 and $3m in 2018. Before co-founding Buffer, Joel co-founded OnePage and StartupMill and was a web developer in the UK.

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In Today’s Episode You Will Learn:

1.) How Joel made his way from web developer in the UK to founder of Buffer, in 2018 a business that did $3m in profit?

2.) What does Joel mean when he says that “fundraising is a bigger decision than most people realise”? At what moments does Joel believe that the founders are no longer the boss? When did Joel feel he was no longer the boss? What does Joel wish founders knew more about the VC process and mechanics? What questions must they ask VCs?

3.) Would Joel agree with Anand Sanwal, previously on the show that “VCs foie-gras their startups”, forcing synthetic growth? What is the right way for founders to respond to this pressure? How did Joel personally handle the pressure? How does Joel assess and analyse the current VC ecosystem? What would he most like to change?

4.) There was a time when individuals did not want Joel to be CEO, how did Joel deal with that? What would Joel advise founders in the same position? What are the right steps to take? Joel then lost his co-founder, how was that process for Joel? What does he know now that he wishes he had known at the beginning of that process? How does he look to retain that level of support and guidance from someone other than a co-founder?

5.) What does Joel mean when he says, “leaders must lean into transparency”? Are there any limitations to being overly transparent? Now as a profitable company, how does Joel think about profit sharing with the team? What does profitable status allow the team to achieve and do that is not normally possible for VC backed co’s?

Items Mentioned In Today’s Show:

Joel’s Fave Book: A Little Life

As always you can follow Harry, The Twenty Minute VC and Joel on Twitter here!

Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Alex Clayton is a Partner @ Spark Capital, one of the leading firms of the last decade with a portfolio including the likes of Slack, Postmates, Oculus, Cruise, Twitter, the list goes on. As for Alex he co-led Spark’s investments in Pendo and Outreach and then led Spark’s investments in Justworks, Braze (Appboy) and JFrog. Before Spark, Alex spent three years at Redpoint Ventures as a senior associate where he sourced or was actively involved in the firm’s investments in Duo Security, JustWorks, RelateIQ (Salesforce.com), Infer, Lifesize and Sourcegraph. Prior to joining Redpoint, Alex was in the TMT investment-banking division of Goldman Sachs where he worked with Intuit, Yelp, SanDisk, and others. Fun fact, in the past Alex played on the ATP World Tennis Tour, competing in the U.S. Open and many other ATP events.

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In Today’s Episode You Will Learn:

1.) How Alex made his way from the world of investment banking with Goldman Sachs to one of the valley rising stars in the world of enterprise investing? What were Alex’s biggest takeaways from his time at Redpoint and working with Tom Tunguz?

2.) How does Alex think about and approach sourcing today? How does Alex find most of his deals? How does Alex breakdown both thesis and network driven sourcing? How does sourcing at growth differ to sourcing at the early stage? If Alex has to meet founders when they are not raising, what does Alex advise founders who are told that you should not “always be raising”?

3.) How does Alex think about market sizing and evaluation today? What does he mean when he says he closely examines “market depth”? How does Alex determine whether a company has the ability to scale from a niche into a much larger TAM? What are the risks Alex is willing vs not willing to take when it comes to market?

4.) How does Alex think about competitor analysis when evaluating an opportunity today? In a world of almost infinite capital, does Alex believe that cash alone is a significant moat for competition? In customer calls when they discuss competition, what excites Alex to hear? How does Alex structure those customer reference calls?

5.) Alex has studied some of the best in class when it comes to SaaS, what do the best in class look like when it comes to: 1.) Quota attainment. 2.) Payback period. 3.) Net dollar retention and churn? 4.) Capital efficiency? Growth rate? Ultimately, what does Alex believe that it takes to go public having studied so many S1s?

Items Mentioned In Today’s Show:

Alex’s Fave Book: Zero to One by Peter Thiel

Alex’s Most Recent Investment: Braze

As always you can follow Harry, The Twenty Minute VC and Alex on Twitter here!

Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Mike Hirshland is the Co-founder of Resolute Ventures, one of the leading pre-seed and seed stage funds of the last decade having recently announced their new $75m Fund IV. In prior funds they have the likes of OpenDoor, Mixmax, Greenhouse, AppZen and more incredible companies. As for Mike, prior to founding Resolute, he founded Dogpatch Labs, the community which helped launch over 350 companies including Instagram. Before Dogpatch, Mike was a partner with Polaris Venture Partners from 1999-2011, where he was the original seed investor behind Automattic, Q1 Labs (acquired by IBM for $600 million), Quantcast and KISSmetrics.

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In Today’s Episode You Will Learn:

1.) How Mike made his way from a legal clerk in the US Supreme Court to founding his own venture firm in the form of Resolute Ventures?

2.) What does Mike mean when he says Resolute invest at the “old seed stage?” What stage of development and traction are the companies at this stage? Why does seed investing out of a $Bn fund not make sense to Mike? What are the acceptable vs unacceptable risks at this stage?

3.) How does Mike think and assess portfolio construction today? How many lines in the portfolio is enough to be sufficiently diversified? How does Mike think about ownership given his thesis on diversification? How does Mike assess his own price sensitivity today? How does Mike think about loss ratio within the portfolio today?

4.) What are the ideal attributes of the founder/VC relationship to Mike? Is it right for the investor to also be friends with their founders? What can founders do to really build and deepen relationships with investors both during and outside of official fundraises? Where does Mike often see founders making mistakes here?

5.) How does Mike think about the right time to establish a board? What does Mike advise founders in terms of board composition in the early days? How does Mike look to build a sense of “board intimacy” with his founders? Why does Mike believe that there is a “counter-productivity to boards at seed”?

Items Mentioned In Today’s Show:

Mike’s Fave Book: A Little Life

As always you can follow Harry, The Twenty Minute VC and Mike on Twitter here!

Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Adam Pritzker is the Chairman & CEO @ Assembled Brands, a holding company providing working capital and financial services to emerging brands. In October 2018, they raised $100m in development capital from the prestigious Oaktree Capital Management. As for Adam, he is also a co-founder of General Assembly where during his tenure, prior to its acquisition by Addecco Group, he served as Chief Creative Officer, Chief Product Officer, and Chairman. For his entrepreneurial endeavors, Adam was featured in Forbes’ 30 Under 30, Vanity Fair’s The Next Establishment, Inc. Magazine’s 30 Under 30, and Business Insider’s Silicon Alley 100.

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In Today’s Episode You Will Learn:

1.) How Adam made his way into the world of startups with the co-founding of General Assembly and how that led to his founding Assembled Brands and financing the future of brands?

2.) Why is Adam optimistic about the current state of the consumer brand and retail environment? How does Adam respond to Alex Taussig @ Lightspeed’s suggestion of the “re-platforming of retail”? How does Adam approach the changing demographics of consumer spend? What does this mean for both the brands and the channels they use to acquire customers? Does Adam believe we are in a consumer bubble today?

3.) How does Adam think about the lack of free and open distribution today for consumer companies? Are the traditional channels now too expensive to acquire customers on? How does Adam advise consumer founders on the saturation rate of marketing channels? How can they foresee the ceiling ahead of time?

4.) Adam has previously stated that Instagram is the new QVC, what did he mean by that? What type of consumer brand is Instagram best suited for? Why does Adam believe that in many cases the venture financing method is suboptimal and wrong for these scaling brands? What can founders who have taken VC funds and now seen it was potentially a mistake do?

5.) Why does Adam believe that the “infrastructure to power emerging brands is broken”? How can the current stack and infrastructure for brands be improved? What metrics should consumer founders really hone in on today? What sort of metrics suggests a brand is VC backable vs is not VC backable? How does Adam think about the ability of the consumer brand space to provide venture returns at scale?

Items Mentioned In Today’s Show:

Adam’s Fave Book: (1.) The Coddling of the American Mind: How Good Intentions and Bad Ideas Are Setting Up a Generation for Failure. (2.) The Upside of Stress: Why Stress Is Good for You, and How to Get Good at It

Adam’s Most Recent Investment: Felix Gray 

As always you can follow Harry, The Twenty Minute VC and Adam on Twitter here!

Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Victoria Treyger is a General Partner & Managing Director @ Felicis Ventures, one of the leading venture firms of the last decade backing 2 unicorns per year since founding including Shopify, OpenDoor, Flexport, Adyen, Twitch, Fitbit and many more. At Felicis, Victoria led the firm’s investments in prior 20VC guest Assaf Wand @ Hippo, Sentio, Sentilink, Blume, Floravere, and other stealth brands. Prior to joining Felicis, Victoria was Chief Revenue Officer of Kabbage. During her six-year tenure, Victoria and her team were instrumental in scaling revenue into the hundreds of millions of dollars and delivered a compound annual growth rate of over 100%. Victoria’s deep operating experience also includes leadership roles at Amazon, American Express, Travelocity, and RingCentral.

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In Today’s Episode You Will Learn:

1.) How Victoria made her way into the world of VC as GP @ Felicis today having scaled revenue into the 100s of millions with Kabbage on the operating side of the table?

2.) Having just made the move from the world of operations, what are the most surprising aspects of venture? What elements have you found to be the most challenging? How does Victoria think about what it takes to be the most effective coach? What can the investor do to build that level of trust and transparency with the founder?

3.) In terms of being a board member, how involved does Victoria think the board member should be? Who is the best board member Victoria has worked with? What made them so special? What are Victoria’s biggest pieces of advice to founders when it comes to how to run an efficiency board? What is the right way for founders to think about board composition?

4.) What 3 trends in the world of consumer and CPG make Victoria so excited to be investing in the space today? What has fundamentally changed about the distribution of those products that changes the way we consume the products? Does this mean Victoria would disagree we are in a D2C bubble today?

5.) Speaking of distribution, how does Victoria respond to the suggestion “there is a lack of free and open distribution today” with customer acquisition costs being so expensive? How does Victoria think about the consumer and CPG space’s ability to provide venture returns at scale moving forward?

Items Mentioned In Today’s Show:

Victoria’s Fave Book: Mindset: How You Can Fulfil Your Potential, Personal History

Victoria’s Most Recent Investment: SentiLink

As always you can follow Harry, The Twenty Minute VC and Victoria on Twitter here!

Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Austen Allred is the Founder & CEO @ Lambda School, a 9 month, immersive program that gives you the tools and training you need to launch your new career—from the comfort of your own home. As a Lambda student, you pay nothing until you’re earning $50k or more. And if you don’t, it’s free. To date, Austen has raised over $48m with Lambda from a personal favourite of mine Bedrock, GGV, GV, Stripe and Ashton Kutcher just to name a few. Prior to founding Lambda, Austen was Senior Manager for Growth @ LendUp and before that co-founded Grasswire.

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In Today’s Episode You Will Learn:

1.) How Austen made his way from being broke, sleeping in a car to founding one of Silicon Valley’s hottest startups in the form of Lambda School?

2.) Austen lived in his car for many months in Palo Alto, what did Austen come to learn about himself from that experience? Before Austen has said, “it is not about money”, so how would Austen describe his personal relationship to money? Consequently, what does this mean for Austen’s relationship to risk?

3.) Austen previously stated he was “determined to never raise VC again before Lambda School”. 2 years and $47m later, what changed in his attitude to raising VC? How mus every founder examine their business model before raising VC? What is the one question they must ask pre-raise?

4.) Austen recently raised a $30m Series B round, how did that round come about? What is Austen’s biggest advice when it comes to investor selection? How does Austen think about when is the right time to raise big? How does that impact and affect operating mentality? What was it about Geoff Lewis that made Austen take his offer over others?

5.) Question from Geoff @ Bedrock: How does Austen iterate on all aspects of the business so fast? Why does Austen believe that the speed and quality of decisions are not mutually exclusive? Why does Austen believe the faster you ship, the higher quality they will be? How does Austen determine which experiments to stick with vs drop?

Items Mentioned In Today’s Show:

Austen’s Fave Book: Les Miserables, The Wright Brothers

As always you can follow Harry, The Twenty Minute VC and Austen on Twitter here!

Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Jeff Richards is Managing Partner @ GGV Capital, one of the leading venture firms of the last decade with a portfolio including the likes of Alibaba, Slack, Square, Xiaomi, Peloton, OpenDoor, just to name a few. As for Jeff, he sits on the board of or is an observer at BigCommerce, Brightwheel, Gladly, Lambda School, Namely and Tile just to name a few. Jeff also led GGV’s investments in Buddy Media (acquired by Salesforce), HotelTonight, Flipboard and has been actively involved in GGV’s investments in Opendoor, Domo, Square and Wish. Prior to joining GGV, Jeff founded two software companies: R4 (acquired by VeriSign), and QuantumShift, backed by Texas Pacific Group (TPG).

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In Today’s Episode You Will Learn:

1.) How Jeff made his way into the world of VC with GGV from founding and scaling 2 software companies in the 90s? What were Jeff’s 2 biggest takeaways from having the company he founded raise over $100m then go to $0 in the crash?

2.) How does Jeff approach and see the transition from founder to CEO today? When does this transition need to occur? How do first-time founders differ compared to experienced serial entrepreneurs when it comes to building their teams? Where do they often struggle or make mistakes? What advice does Jeff offer them?

3.) Jeff has previously said, “do not raise for the highest valuation”, what is his thinking here? What specific examples does Jeff have of why it can hurt and damage both the founder and the company? How does Jeff think about his own price sensitivity today? How does he determine when a stretch is a stretch too far? From backing the likes of Alibaba, Xiaomi and Didi, what were his biggest takeaways when it came to price?

4.) Decision-making is one of the only products venture has, how does Jeff and GGV approach decision-making as a firm today? Being a slightly later stage firm, how do they think about reserve allocation? What does the re-investment decision-making process look like? How does GGV think about attribution as a firm today? What are the benefits?

5.) What advice would Jeff give to an individual that has just entered VC? What does Jeff know now that he wishes he had known at the beginning? How does Jeff think about what it takes to be a truly special board member? What one or two things can a board member do to move the needle in their relationship with their founder?

Items Mentioned In Today’s Show:

Jeff’s Fave Book: In an Uncertain World: Tough Choices from Wall Street to Washington

Jeff’s Most Recent Investment: Lambda School, Electric

As always you can follow Harry, The Twenty Minute VC and Jeff on Twitter here!

Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Rob Sadow is the Founder & CEO @ Scoop, the startup that dramatically improves your commute providing convenient carpools with co-workers and neighbours. To date, Rob has raised over $46m in funding for Scoop from the likes of Danny Rimer @ Index, Brook Porter @ G2VP, Zaw Thet @ Signia Venture Partners and BMW i Ventures just to name a few. Before founding Scoop, Rob was a Manager @ Bain & Company and before that spent time in Israel with Better Place, working to provide electric vehicle networks to help accelerate the global transition to sustainable transportation.

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In Today’s Episode You Will Learn:

1.) How Rob made his way from the world of consulting and Bain to founding the future of convenient commutes with Scoop?

2.) How does Rob approach key decisions? What does Brook Porter @ G2VP mean when he says, “from a first principles perspective”? How does Rob determine when to make decisions with the head or the heart? Does Rob agree with Fred Destin, “as a founder, decisions are never perfect, it is about batting average”? Where does Rob see many make mistakes when it comes to decision-making?

3.) How does Rob find the dynamics of working with his brother as his co-founder? What are some of the core challenges? How does one make it scale and how does the relationship need to change over time? What is Rob’s biggest advice to others when thinking about the person they partner with?

4.) How does Rob think about board construction? What have been some of Rob’s biggest lessons in really using your board to get the most out of them? What works well for this? What does not work? How can founders create this level of relationship with their board members? Should founders direct their ask to specific individuals when soliciting help from their board?

5.) Why does Rob believe that they have next to no attrition of employees at Scoop? What have been some of Rob’s biggest lessons when it comes to both culture creation and maintenance? How does Rob think leaders can invest more in their employees? What does this look like? Where do many go wrong or misallocate?

Items Mentioned In Today’s Show:

Rob’s Fave Book: The Wheel of Time

As always you can follow Harry, The Twenty Minute VC and Rob on Twitter here!

Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Frank Chen is a Partner @ Andreessen Horowitz, one of the world’s most prestigious venture firms with a portfolio including the likes of Airbnb, Coinbase, Github, Lyft, Slack and many more incredible companies. As for Frank, prior to joining the world of venture, he was a VP of Products & UI Design at HP Software and before that held the same title at Opsware. Before that, even cooler, Frank was Director of Product Management @ Netscape where he led a cross-functional team that defined, shipped, and marketed Netscape’s award-winning LDAP directory and security products. 

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In Today’s Episode You Will Learn:

1.) How Frank made the move from the world of operations with Opsware and HP to being a Partner at Andreessen Horowitz?

2.) How does Frank view the current state of play for AI and machine learning? How does the rise of automation shift the economy as we know it? What does it do to class distinctions? How does Frank view it’s impact on the labour market? How does Frank think about the value of truly large datasets? Where is the asymptotic moment where the utility value of data is realised?

3.) With the rise of self-driving, how does Frank perceive the future of car ownership? Who will fundamentally own and operate the vehicles? Will it be a horizontal play or a vertical play? In terms of adoption, why is Frank negative towards a driver assisted transition phase and believe in a more binary transition?

4.) How does Frank perceive the rise of automation and self-driving cars impacting public infrastructure? How will the layout of our cities change over time? How does Frank believe urban real estate could be optimised in a more efficient manner? Which nations does Frank believe will be the first to innovate here?

5.) What is the most challenging element of Frank’s position as Partner @ a16z? How does Frank think about the right way to say not to an entrepreneur? How does Frank look to scale the learning curve rapidly when investigating new industries? What are the challenges here? What advice would Frank give to someone looking to scale learning curves?

Items Mentioned In Today’s Show:

Frank’s Fave Book: The Chronicles of Narnia, The Lord of The Rings

Frank’s Most Recent Investment: Branch

As always you can follow Harry, The Twenty Minute VC and Frank on Twitter here!

Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Rahul Vohra is the Founder and CEO @ Superhuman, the fastest email experience in the world. Fun fact, users get through their inbox twice as fast — and many see Inbox Zero for the first time in years! To date, they have raised funds from our friends at Boldstart, First Round, John Collison, Sam Altman, Wayne Chang, Mike Ghaffery and Yes VC just to name a few. Previously, Rahul founded Rapportive, the first Gmail plugin to scale to millions of users. Rapportive was ultimately acquired by LinkedIn.

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In Today’s Episode You Will Learn:

1.) How did Rahul make his way into the world of startups with the founding of Rapportive and how did that transition to changing the world of email with Superhuman?

2.) What does Rahul mean when he says, “you can reverse engineer a process to get to product market fit”? What does Rahul believe is the defining metric which determines your “product market fit score”? What is Julie Supan’s framework? How did Dropbox and Airbnb use it to increase their product market fit? How can founders implement it into their process?

3.) What can founders do to expand the customer base to include users that currently are “somewhat disappointed”? What are the right questions to ask? What do we do with this feedback? How do we further segment the user base? Why should we “disregard the users whereby the primary benefit of the product does not resonate”?

4.) How does Rahul approach product roadmap and prioritisation? How can founders ensure that continuous tracking and user feedback is engrained within the organisation? What tools does Rahul do to monitor and capture this? What are some of Rahul’s biggest lessons from going through this painstaking process stage by stage?

5.) Finally on fundraising, what does Rahul mean when he says, “always be raising but never be actively raising”? What are the benefits of this? How can founders transition catch up coffee into fundraising subtly? How does Rahul feel about party rounds? What are the pros? What are the downsides? How does Rahul advise founders here?

Items Mentioned In Today’s Show:

Rahul’s Fave Book: The Art of Game Design

As always you can follow Harry, The Twenty Minute VC and Rahul on Twitter here!

Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Steve Case is Chairman and CEO of Revolution with the mission being to establish themselves as the premier venture firm outside of Silicon Valley. On the other side of the table, Steve is recognised as one of America’s best-known and most accomplished entrepreneurs as the co-founder of America Online (AOL). Under his leadership, AOL was the first internet company to go public and became the world’s largest and most valuable internet company delivering an 11,616% return to shareholders. In 2000, Steve negotiated the largest merger in business history, bringing together AOL and Time Warner. Among many other achievements, in 2014, Steve was named a Presidential Ambassador for Global Entrepreneurship. Steve has also been a leading voice in shaping government policy and was instrumental in passing the JOBS (Jumpstart Our Business Startups) Act. Finally, Steve is also Chairman of the Case Foundation, where he and his wife, Jean, have invested in hundreds of organizations, initiatives and partnerships.

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In Today’s Episode You Will Learn:

1.) How Steve made his way into the world of technology with the founding of AOL in 1985 and how that led to his founding of Revolution and investing today in the “rise of the rest” today?

2.) Having sat on both sides of the table both as founder and VC, what does Steve thinks make the truly special VCs? How do they engage with entrepreneurs? How do they actively move the needle for their companies? How would he like to see VCs of the future change and adapt their ways?

3.) How does Steve think about market timing when investing today? What were some of Steve’s biggest lessons from seeing the dot com bubble and 2008 in both the role of entrepreneur and investor? What does he mean when he says, ‘it can be dangerous to have a depression mentality’ when investing?

4.) How does Steve analyse and assess the current fundraising environment today? Why does Steve see an incredible opportunity in funding companies outside the 3 traditional hubs of Silicon Valley, NYC and Boston? What needs to happen to drive this equalisation of funding further? What would Steve like to see change?

5.) What does Steve think are the 3 seminal roles of the CEO? What does Steve mean when he says that the CEO ‘must be a shock absorber for company morale’? How does Steve deal with s*** hit the fan moments? What are his coping mechanisms and how does he advise entrepreneurs on them?

Items Mentioned In Today’s Show:

Steve’s Fave Book: The Third Wave, Be Fearless: 5 Principles For A Life of Breakthroughs and Purpose

As always you can follow Harry, The Twenty Minute VC and Steve on Twitter here!

Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Henrique Dubugas is the Founder & CEO @ Brex, the first corporate card for startups offering instant online application, no personal liability, and tailored rewards. In a staggering 2 years, Henrique has grown Brex to a $1.1Bn valuation having raised over $180m in funding from some of the best in the business including Peter Thiel, Max Levchin, Elad Gil, DST, Y Combinator and IVP just to name a few. As for Henrique, prior to founding Brex he founded Pagar.me, a payments solution that he sold in Sept 2016, a year that the platform processed over $1.5 billion in GMV.

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In Today’s Episode You Will Learn:

1.) How Henrique made his way from learning to code games in Brazil to starting a leading payment processor to founding one of the world’s fastest growing B2B companies in Brex?

2.) How does Henrique think about hiring the very best people? How has that strategy shifted and changed over time? What is the best advice Henrique has been given on hiring? What interview questions does Henrique think are crucial to ask? What are leading indicators that an individual has the ability to scale with the company?

3.) Why does Henrique think it is wrong to down people for being “compensation motivated”? How does Henrique think about compensation structures? Should candidates have to take pay cuts to join startups? What have been some of Henrique’s biggest learnings and challenges here?

4.) How does Henrique approach the current sentiment to fundraising in the valley today? Why does Henrique disagree with founders who have periods of not speaking to VCs? What does Henrique believe is the right way to build VC relationships? How does Henrique think about the right time to raise? What advice does Henrique have for founders when it comes to investor selection?

5.) How does Henrique think about his own personal development? Where would he personally like to improve and strengthen? What is he doing to make this happen? How has Henrique seen himself as CEO change over the last 2 years with Brex? What have been some of the challenges of scaling himself as CEO?

Items Mentioned In Today’s Show:

Henrique’s Fave Book: 7 Powers: The Foundations of Business Strategy

As always you can follow Harry, The Twenty Minute VC and Henrique on Twitter here!

Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

David Cohen is the Founder and co-CEO of Techstars, the worldwide network that helps entrepreneurs succeed. To date, David has backed hundreds of startups including the likes of Uber, SendGrid, Twilio, ClassPass, PillPack and more. In total, these investments have gone on to create more than $80B in value. Prior to Techstars, David was a co-founder of Pinpoint Technologies which was acquired by ZOLL Medical Corporation in 1999. Later, David was the founder and CEO of earFeeder, a music service that was sold to SonicSwap. If that was not enough, David is also theco-author (with Brad Feld) of Do More Faster; Techstars Lessons to Accelerate Your Startup.

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In Today’s Episode You Will Learn:

1.) How David made his way from, his words “geeky hacker” to the founder of one of the world’s largest accelerators, Techstars and investor in multiple unicorns?

2.) What does David mean when he says that when assessing founders he studies “the moment of integrity”? What does he want to see from founders in those moments? What are some potential red flags? If a negative response, what are the subsequent actions an investor must take in this situation?

3.) How does David think about the right time to establish a board? What are the benefits of establishing your board with the seed round? What does David believe is the key to highly efficient boards? How has David changed as a board member over the years? Why does David believe, when building a company, “you always have to have a pessimist in the room”?

4.) When negotiating deals, what does David mean when he says “the terms must match the story”? How does David determine between a bridge and a bridge to nowhere? What can investors do to protect themselves if the targets of the business are not met and they have an uncapped note in place? How should they communicate this?

5.) Techstars today invests in over 500 companies per year, how does David think about reserve allocation across the portfolio? How does David feel about stack ranking portfolio co’s quarterly and concentrating capital accordingly? Why is this not effective? Why should seed and angel investing be an entirely different asset class to VC?

Items Mentioned In Today’s Show:

David’s Fave Book: The Soul of Money: Transforming Your Relationship with Money and Life

David’s Most Recent Investment: Ordermark

As always you can follow Harry, The Twenty Minute VC and David on Twitter here!

Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Anjney Midha is the Founder & CEO @ Ubiquity6, the startup that allows you to edit reality together, turning any location into a space for real-time, shared AR and VR experiences. To date, Anjney has raised over $38m in funding for Ubiquity6 from some of the very best in the business including Phin @ First Round, Mike Volpi @ Index and Mitch @ Benchmark. Prior to Ubiquity6, Anjney spent 4 years on the other side of the table as an investor @ Kleiner Perkins and then as Founding Partner @ KPCB Edge, Kleiner’s program helping founders get off the ground in AR, VR and Computer Vision.

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In Today’s Episode You Will Learn:

1.) How Anjney made his way into the world of startups on the investing side of the table with Kleiner Perkins and how that transitioned to his founding of Ubiquity6?

2.) What does Anjney believe is structurally wrong with venture now more than ever? How does the extended period of privatisation affect emerging partners in venture firms? How does Anjney think the very best of investors think about and analyse history? Why does Anjney believe venture is the business of financing “creative hits”?

3.) What are the 3 structural impediments facing venture today? Why and how does Anjney believe we will see a new class of VC enter the space and be very successful? In what form could this take? How can they outcompete the current crop of VCs? What does Anjney mean when he discusses the “squishy middle” of VC?

4.) Anjney is backed by Index, Benchmark and First Round, what are the commonalities among those firms that make them so special? How do the very best of firms engage and build relationships with their entrepreneurs? How does Anjney believe that focus can be successfully applied to venture? What is the right way for VCs to evaluate themselves?

5.) What do VCs really want to know when they are approaching risk assessment with founders? What can founders do to mitigate risk when pitching to VCs? How do the very best founders attract the very best talent to their team? What are the commonalities? Where do some go wrong in building the optimal team?

Items Mentioned In Today’s Show:

Anjney’s Fave Book: Rainbows End

As always you can follow Harry, The Twenty Minute VC and Anjney on Twitter here!

Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Sam Lessin is a Founding Partner @ Slow Ventures, one of the leading early-stage funds on the West Coast with a portfolio including the likes of Robinhood, Gusto, Pinterest, Casper, Postmates and many more incredible companies. Sam is also the Co-Founder & Co-CEO @ Fin Analytics, the startup that provides precision measurement and coaching for high-performance operations teams. Before founding Fin and Slow, Sam spent 4 years at Facebook as a VP of Product Management following their acquisition of his prior company, Drop.io.

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In Today’s Episode You Will Learn:

1.) How Sam made his way into the world of venture with the founding of Slow following the acquisition of his company and 4 years in product at Facebook?

2.) How does Sam think about the difference between investing small personal checks vs managing institutional funds? What is the subsequent effect on mindset when investing? How does one prevent an increased conservatism? What does Sam mean when he says “VC forces some businesses into existence and makes others hard to fund?

3.) Why does Sam believe that man + machine must have a symbiotic relationship in the future? What does this look like in reality? When comparing today to the industrial revolution, is Sam concerned by the increased rate of adoption today? What does this mean for different categories of work? Why does Sam believe we will need more philosophers?

4.) Why does Sam believe that too much emphasis in the world of crypto is placed on Dapps? Why is he concerned by Dapps? What are of crypto does Sam believe is most exciting and investable today? Does Sam agree with Elad Gil that we will see the re-centralisation of talent back to the valley with the scaling of crypto co’s?

5.) On governments, why does Sam not believe that both local and national governments will allow scooter companies to become meaningfully profitable in the future? How does Sam think about the balance and trade-off between privacy and security that faces many governments today?

Items Mentioned In Today’s Show:

Sam’s Fave Book: Lessons of History

Sam’s Most Recent Investment: Fetcher.ai

As always you can follow Harry, The Twenty Minute VC and Sam on Twitter here!

Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Joel Flory is the Founder & CEO @ VSCO, the startup that allows you to take your photography to the next level, with the mission to help everybody fall in love with their own creativity. To date, Joel has raised over $70m in funding with VSCO from some of the best in the business including Accel, Glynn Capital Management and Goldcrest Investments. Prior to founding VSCO, Joel founded his own photography company which he ran successfully for 10 years.

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In Today’s Episode You Will Learn:

1.) How Joel made his way from photographer to one of San Francisco’s hottest startup founders today?

2.) How does Joel approach the current sentiment and approach to fundraising? Why were Joel and his co-founder unable to raise in the early days? How does Joel approach the element of investor selection? Brand name or partner? How does Joel look to really build relationships with VCs in compressed timeframes? What is Joel’s litmus test to determine if a VC is interested? What single value add can a VC provide that is most important?

3.) What does Joel mean when he says, “you have to align your business model with your mission?” How can one really determine if they are aligned? How does this alignment change and alter with scale? What was the thinking behind the shift to a subscription business with VSCO? Was Joel worried it would impact the valuation and change the valuation mechanism to a multiple of revenue assessment?

4.) What do the optimal leadership team dynamics look like to Joel? What has worked well for Joel in binding the leadership team together? What have been some of the biggest challenges? How does Joel think about cross-functional communication across the leadership team?

5.) How does Joel think about his personal development today? Where would he like to improve? Where is he already strong? With a family and company in hyper-growth, how does Joel think about attaining that work-life balance? What advice would he have for other here? How does Joel determine what to say yes vs no to? What are some tips and hacks to this?

Items Mentioned In Today’s Show:

Joel’s Fave Book: How To Talk So Kids Will Listen and Listen So Kids Will Talk 

As always you can follow Harry, The Twenty Minute VC and Joel on Twitter here!

Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Are you thinking about life insurance in the new year? Ladder Is the smart and easy way to get term life insurance online. With Ladder there are no commissioned agents and no policy fees — you can be done in minutes. Even better, coverage can start today, if you qualify, and you can cancel anytime. Ladder is licensed and backed by trusted partners, with billions in coverage. Visit ladderlife.com to apply and get an instant decision on fully underwritten term life insurance, and check life insurance off your list TODAY.

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Josh Kopelman is Founder & Partner @ First Round, one of the world’s leading seed funds with a portfolio including the likes of Uber, Warby Parker, Flatiron Health, Square, HotelTonight, GOAT and more incredible companies. As for Josh, he founded First Round in 2004 to reinvent seed stage investing. Since he has invested in over 200 startups and been ranked 4th in Forbes Midas List and named one of the top ten ‘angel investors’ in the US by Newsweek magazine. Josh has previously sat on the boards of Flatiron Health, Clover Health, AppNexus and more. 

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In Today’s Episode You Will Learn:

1.) How Josh made his way into the wonderful world of venture from angel investing and what the inspiration behind the founding of First Round was?

2.) How does Josh think about price sensitivity today? What were his learnings from being priced out of the seed round for Twitter and Dropbox? How has Josh seen his relationship to price change over time? How did witnessing the boom and bust both as operator and investor affect his investing mentality today?

3.) How does Josh and First Round think about reserve allocation? How has their thinking changed and evolved over time? Does Josh believe that ownership is fundamentally built on first check? What does the investment decision-making process look like for reserves? In terms of allocation, how does Josh think about time allocation across portfolio? Spend it with the winners, they return the fund or the strugglers and save cents on the dollar?

4.) Josh has spent over 3,000 hours on boards, what have been some of the biggest inflection points that have changed the way he thinks about being a good board member? How has he seen his style and approach change over time? What advice would Josh give to an individual that has just gained their first institutional board seat?

5.) Why does Josh believe that we fundamentally neglect “the pick” today in startup world? Why does Josh believe a high degree of startup mortality begins at the pick (idea) stage? How do the very best founders aproach this stage? How should these founders approach picking their investors? What should they look for? What should they be wary of?

6.) Why does Josh want to be known as a better picker of partners than investments? How has Josh thought about the building ou of the first round partnership over time? If there was anything he would have done differently, what would it be? Why does Josh fundamentally disagree with attribution? How does Josh think about generational transition? What are the steps required to do it well?

Items Mentioned In Today’s Show:

Josh’s Fave Book: Thinking in Bets: Making Smarter Decisions When You Don’t Have All the Facts

As always you can follow Harry, The Twenty Minute VC and Joel on Twitter here!

Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Are you thinking about life insurance in the new year? Ladder is the smart and easy way to get term life insurance online. With Ladder there are no commissioned agents and no policy fees — you can be done in minutes. Even better, coverage can start today, if you qualify, and you can cancel anytime. Ladder is licensed and backed by trusted partners, with billions in coverage. Visit ladderlife.com to apply and get an instant decision on fully underwritten term life insurance, and check life insurance off your list TODAY.

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Ready for tax season? Wishing you’d kept a closer eye on your books this year? Set yourself up for success in 2019 with Pilot. Pilot is a bookkeeping company focused on the needs of startups. Their team of SF-based bookkeepers are assisted by engineers to automate the most error-prone parts of bookkeeping, so you know you’re getting an accurate report every month. Plus, Pilot does accrual basis bookkeeping in Quickbooks Online, so you’re never locked into a proprietary platform. Learn more and sign up here. Don’t wait – the first 100 members of the Twenty Minute VC community get 20% off Pilot Core for six months.

Olof Mathé is the Founder & CEO @ Mixmax, the startup that provides powerful analytics, automation and enhancements for your outbound communications. In the past, Mixmax achieved the almost the impossible in SaaS, true viral growth and a $0 CAC. As a result, Olof has raised over $13m in funding from some dear friends of the show in the form of Jason @ SaaStr, Mike @ Harrison Metal, Mike @ Floodgate and Carl @ Creandum, to name a few. As for Olof, prior to Mixmax he led the team that built Inkling Habitat, now adopted by the world’s largest publishers and before that he was an entrepreneur and worked at Skype and McKinsey.

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In Today’s Episode You Will Learn:

1.) How Olof made his way from the world of McKinsey and Skype to changing the way we interact with our email today with Mixmax?

2.) What does Olof mean when he says that founders go through 3 stages of denial when scaling their team? How does Olof think about the right time to add certain roles? What have been some of his big learnings here? Where do people make mistakes in the timing of hires? How does Olof think about the transition from generalist to specialist with scale?

3.) Why does Olof believe that in the majority of cases, it is not optimal or possible for founders to hire through their network? What is the right way for founders to approach building candidate pipe? What is the right way for founders to engage with recruiters? What is required in the recruiter/founder relationship for it to be a success?

4.) Why does Olof get worried when he hears “they will grow into the role”? What are the core leading indicators that suggest someone has the ability to scale vs not scale with the role? How much time does one give an employee to provide value and show their ability in the team? How does Olof think about the right way to let someone go?

5.) What are the 3 interview questions that all founders must ask in the hiring process? What answers indicate a candidate that is best suited for the role and company? What are red flags to watch for both in their answer and tone? How has Olof changed his hiring style over the last few years with Mixmax?

Items Mentioned In Today’s Show:

Olof’s Fave Book: SPQR: A History of Ancient Rome

As always you can follow Harry, The Twenty Minute VC and Olof on Twitter here!

Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Are you thinking about life insurance in the new year? Ladder Is the smart and easy way to get term life insurance online. With Ladder there are no commissioned agents and no policy fees — you can be done in minutes. Even better, coverage can start today, if you qualify, and you can cancel anytime. Ladder is licensed and backed by trusted partners, with billions in coverage. Visit ladderlife.com to apply and get an instant decision on fully underwritten term life insurance, and check life insurance off your list TODAY.

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Ready for tax season? Wishing you’d kept a closer eye on your books this year? Set yourself up for success in 2019 with Pilot. Pilot is a bookkeeping company focused on the needs of startups. Their team of SF-based bookkeepers are assisted by engineers to automate the most error-prone parts of bookkeeping, so you know you’re getting an accurate report every month. Plus, Pilot does accrual basis bookkeeping in Quickbooks Online, so you’re never locked into a proprietary platform. Learn more and sign up here. Don’t wait – the first 100 members of the Twenty Minute VC community get 20% off Pilot Core for six months.

Hunter Somerville is a Partner at Greenspring Associates, a leading venture firm and fund of funds. On the direct side their portfolio includes the likes of Sonos, App Annie, Docusign and Alibaba just to name a few. As for their fund investing, they have backed the likes of Accel, Founders Fund, Thrive, Lightspeed, Foundry Group and many more incredible managers. As for Hunter, he is actively involved in the assessment of micro-vc managers for the Firm where he sits on the LP advisory boards for the likes of Pear, Foundry Group, Scale Venture Partners and BullPen Capital just to name a few. Prior to joining Greenspring, Hunter worked as an Associate for Camden Private Capital.

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In Today’s Episode You Will Learn:

1.) How Hunter made his way into the world of fund investing and came to be a Partner @ Greenspring?

2.) How does Hunter assess the world of micro-VC today? Does Hunter think we will see the market start to shrink as LPs become over-allocated to the space? Why does Hunter believe the barriers for micro VCs to raise are lower than ever? What does this mean for the future of early stage?

3.) How does Hunter fundamentally approach the assessment of new funds? Is it all about track record? How does he look to build a framework/model to predict future performance? What makes Hunter sceptical when assessing new opportunities? Where do many managers go wrong in the fundraising process? How does Hunter think about loss ratio?

4.) As an LP having to allocate to multiple different stages, why does Hunter feel there is a shortage of dedicated A and B round funds? How does Hunter expect both reserve allocation and loss ration to alter as we move from early to later stage? How does Hunter feel about opportunity funds? How does Hunter and other LPs assess GP led restructurings?

5.) Why is Hunter bullish on the future for direct secondaries? Why does he believe this is fundamentally good for the ecosystem? How does Hunter think about early stage managers in their needs for early liquidity? To what extent will early stage managers need to navigate the private secondaries market to attain this liquidity?

Items Mentioned In Today’s Show:

Hunter’s Fave Book: Great Expectations by Charles Dickens

Hunter’s Most Recent Investment: Amplify Partners

As always you can follow Harry and The Twenty Minute VC on Twitter here!

Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Are you thinking about life insurance in the new year? Ladder Is the smart and easy way to get term life insurance online. With Ladder there are no commissioned agents and no policy fees — you can be done in minutes. Even better, coverage can start today, if you qualify, and you can cancel anytime. Ladder is licensed and backed by trusted partners, with billions in coverage. Visit ladderlife.com to apply and get an instant decision on fully underwritten term life insurance, and check life insurance off your list TODAY.

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Ready for tax season? Wishing you’d kept a closer eye on your books this year? Set yourself up for success in 2019 with Pilot. Pilot is a bookkeeping company focused on the needs of startups. Their team of SF-based bookkeepers are assisted by engineers to automate the most error-prone parts of bookkeeping, so you know you’re getting an accurate report every month. Plus, Pilot does accrual basis bookkeeping in Quickbooks Online, so you’re never locked into a proprietary platform. Learn more and sign up here. Don’t wait – the first 100 members of the Twenty Minute VC community get 20% off Pilot Core for six months.

Assaf Wand is the Founder & CEO @ Hippo, a new kind of insurance company that provides smart coverage for homeowners with a quote in just 60 seconds. To date, Assaf has raised over $109m in funding for Hippo from some dear friends of the show in the form of Felicis Ventures, GGV Capital, Fifth Wall, Zeev Ventures and Lennar just to name a few. Prior to re-imagining the world of insurance, Assaf founded Sabi, creating products that improve everyday life with superior functionality and design. Sabi was acquired by Urbio in 2015. Before that Assaf held numerous different roles including as a consultant at McKinsey and Investment Associate at Intel Capital.

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In Today’s Episode You Will Learn:

1.) How did Assaf being the worst employee in the world lead to his entrance into the world of early-stage startups and the founding of Hippo?

2.) How does Assaf analyse the current sentiment and approach to fundraising in the valley today? Why does Assaf believe that every company looks one round earlier than it should be for the VCs? How does Assaf think about investor selection? What is the single biggest value a VC partner can provide? Does Assaf agree that founders should “always be raising”? Why does Assaf believe that top funds should not get significant discounts?

3.) What does Assaf believe are the biggest mistakes entrepreneurs make when building their board? On boards, why does Assaf believe there is a danger that partners from top funds have their ideas overweighted due to the prestige of their fund? What can be done to prevent this? What does Assaf believe is the right screening process for new board members?

4.) What does Assaf believe separates the good from the great when it comes to board members? How does Assaf really look to building meaninful relationships with his board members? What has worked well? On the flip side, why does Assaf believe the No 1 element of a board is “do no harm”? Where can board members actually be damaging?

5.) Hippo is growing 30% MoM and will be in 80% of the US in the next 12 months, how does Assaf think about when is the right time to put the pedal to the metal? What are those leading indicators? Where do many founders go wrong here? Is it simply a case of whenunit economics work, one is ready to scale?

Items Mentioned In Today’s Show:

Assaf’s Fave Book: The Fountainhead, The Pillars of The Earth

As always you can follow Harry and The Twenty Minute VC on Twitter here!

Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Are you thinking about life insurance in the new year? Ladder Is the smart and easy way to get term life insurance online. With Ladder there are no commissioned agents and no policy fees — you can be done in minutes. Even better, coverage can start today, if you qualify, and you can cancel anytime. Ladder is licensed and backed by trusted partners, with billions in coverage. Visit ladderlife.com to apply and get an instant decision on fully underwritten term life insurance, and check life insurance off your list TODAY.

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Ready for tax season? Wishing you’d kept a closer eye on your books this year? Set yourself up for success in 2019 with Pilot. Pilot is a bookkeeping company focused on the needs of startups. Their team of SF-based bookkeepers are assisted by engineers to automate the most error-prone parts of bookkeeping, so you know you’re getting an accurate report every month. Plus, Pilot does accrual basis bookkeeping in Quickbooks Online, so you’re never locked into a proprietary platform. Learn more and sign up here. Don’t wait – the first 100 members of the Twenty Minute VC community get 20% off Pilot Core for six months.

Fred Destin is a Founding Partner @ Stride.VC, one of Europe’s newest seed funds with a portfolio including the likes of Cazoo and Forward Health. Over his 17 year career in venture, Fred has established himself as one of Europe’s leading VCs with the exit value of 3 of his portfolio companies alone last year totalling more than $4.5Bn with PillPack’s $1Bn sale to Amazon, Zoopla to Silverlake for $3Bn and Integral Ad Science to Vista for $850m. Fred has also led investments as a General Partner @ Accel in Deliveroo, the world leader of food on demand and Carwow, the number 1 for new car sales in the UK.

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In Today’s Episode You Will Learn:

1.) How Fred made his way into the world of venture and early stage? What was behind his decision to leave Accel to found Stride with Harry?

2.) Why does Fred think many today misunderstand “risk” in venture? How does that apply across the portfolio? Does Fred agree with Brian Singerman, “venture is a game of upside maximisation”? What risks does Fred define as acceptable vs non-acceptable risks? How does Fred really look to strength test the quality and depth of a founder pre-investment? What are the benefits of going through conflict early?

3.) How does Fred think about price sensitivity? What are the core questions a VC can ask when considering the pricing of an opportunity? How does Fred think about reserve allocation? How does Fred analogize this to the best traders? To what extent does TAM play a dominant role in Fred’s evaluation? What does Fred mean when he says “we have to remember, we are the ones that get picked also”?

4.) How does Fred think about and assess innovation within venture? How does Fred perceive the role of data to impact venture over the coming years? Why does Fred believe it is exaggerated that data will disrupt the early stage in the coming years? Where would Fred like to see further innovation in the mechanics of venture?

5.) What does Fred believes separates the good from the great when it comes to board members? How can board members create an environment where the entrepreneur feels they can say all that is wrong? Where do many board members go wrong? Why are board members so wrong to bash a founder for missing their numbers? Why does Fred believe that plans are fiction? WHy is the framework of the plan what really matters?

Items Mentioned In Today’s Show:

Fred’s Fave Book: Man’s Search for Meaning

As always you can follow Harry, The Twenty Minute VC and Fred on Twitter here!

Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Are you thinking about life insurance in the new year? Ladder Is the smart and easy way to get term life insurance online. With Ladder there are no commissioned agents and no policy fees — you can be done in minutes. Even better, coverage can start today, if you qualify, and you can cancel anytime. Ladder is licensed and backed by trusted partners, with billions in coverage. Visit ladderlife.com to apply and get an instant decision on fully underwritten term life insurance, and check life insurance off your list TODAY.

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Ready for tax season? Wishing you’d kept a closer eye on your books this year? Set yourself up for success in 2019 with Pilot. Pilot is a bookkeeping company focused on the needs of startups. Their team of SF-based bookkeepers are assisted by engineers to automate the most error-prone parts of bookkeeping, so you know you’re getting an accurate report every month. Plus, Pilot does accrual basis bookkeeping in Quickbooks Online, so you’re never locked into a proprietary platform. Learn more and sign up here. Don’t wait – the first 100 members of the Twenty Minute VC community get 20% off Pilot Core for six months.

Avi Meir is the Founder & CEO @ TravelPerk, the startup that allows you to book, manage and report all your business travel in one place. To date, Avi has raised over $73m with TravelPerk from the likes of Felix Capital, Yuri Milner, Spark Capital, Sunstone and LocalGlobe to name a few. Before founding TravelPerk, Avi founded HotelNinjas, a web-based hotel management software platform that was ultimately acquired by Booking.com. Prior to that, Avi was VP Product at Budgetplaces.com, which was acquired by Palamon in 2011.

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In Today’s Episode You Will Learn:

1.) How Avi made his way from the world of hotels to the world of founding startups and what was his entry point? How did Avi’s experience with HotelNinja’s impact his operating mindset with TravelPerk today?

2.) How does Avi think about attaining the right board composition? What is the ideal structure? How important is it to have industrial experience around the table? What are the 2 other core skills that Avi believes are required on the board? What can founders do to ensure plasticity of mindset at a board level?

3.) What makes the truly special board members? What do they do both in the good and the bad times to make them so good? What does Avi believe makes the more challenging board members to work with? Why does Avi believe that culture fit at the board level is not discussed enough? What can be done by the founder to improve this?

4.) TravelPerk has now raised over $75m in funding, what does Avi believe they have done well to date to allow them to raise this? For the next round, what would Avi like to improve upon and pushback on further? What advice does Avi have for founders entering negotiations when it comes to both valuation and option pool?

5.) Why does Avi believe that culture and growth are 2 sides of the same coin? What have been some of the biggest challenges in scaling the team with the scaling of the company? How does one retain startup culture when no longer a startup? What would Avi do differently with regards to expansion with the benefit of hindsight?

Items Mentioned In Today’s Show:

Avi’s Fave Book: Delivering Happiness: A Path to Profits, Passion and Purpose

As always you can follow Harry, The Twenty Minute VC and Avi on Twitter here!

Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Are you thinking about life insurance in the new year? Ladder Is the smart and easy way to get term life insurance online. With Ladder there are no commissioned agents and no policy fees — you can be done in minutes. Even better, coverage can start today, if you qualify, and you can cancel anytime. Ladder is licensed and backed by trusted partners, with billions in coverage. Visit ladderlife.com to apply and get an instant decision on fully underwritten term life insurance, and check life insurance off your list TODAY.

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Ready for tax season? Wishing you’d kept a closer eye on your books this year? Set yourself up for success in 2019 with Pilot. Pilot is a bookkeeping company focused on the needs of startups. Their team of SF-based bookkeepers are assisted by engineers to automate the most error-prone parts of bookkeeping, so you know you’re getting an accurate report every month. Plus, Pilot does accrual basis bookkeeping in Quickbooks Online, so you’re never locked into a proprietary platform. Learn more and sign up here. Don’t wait – the first 100 members of the Twenty Minute VC community get 20% off Pilot Core for six months.

Scott Belsky is an executive, entrepreneur, author, and investor. He currently serves as Adobe’s Chief Product Officer and Executive Vice President, Creative Cloud. Before Adobe, Scott co-founded Behance in 2006 and served as CEO until Adobe acquired Behance in 2012. Alongside his role at Adobe, Scott is a Venture Partner at one of the world’s leading venture firms, Benchmark. Scott also actively advises and invests in startups personally having one of the most incredible angel portfolios with early checks in Pinterest, Uber, Periscope, Warby Parker, Carta, Flexport and more. Scott is also the author of Harry’s favourite book of 2018, The Messy Middle.

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In Today’s Episode You Will Learn:

1.) How Scott made his way into the world of startups with Behance, how that translated to the world of angel investing and being Chief Product Officer @ Adobe? WHat does Scott mean when he discusses the correlation between utilisation and happiness?

2.) What does Scott mean when he says he looks for people whereby ‘conversations improve by step function?” What are the best examples of this? How have they shown this? How does Scott think startups founders can manufacture motivation? How has Scott seen the best founders hire the very best team? How do the best founders determine between a stretch and a stretch too far?

3.) In terms of product, what does Scott mean when he refers to the “value of slow cooking”? How does that relate to product creation? Why does Scott often have issues with the MVP approach seen today? How does Scott think about the importance of product simplicity? How can one maintain that over time? Why does Scott believe more founders should spend more time crafting the last mile user experience than they do?

4.) Simplicity is great but VCs often suggest, non-defensible, how does Scott think about building defensibility with simplicity? Simplicity often also narrows market size, how does Scott think about and analyse market size today when investing? Where does Scott think many investors go wrong today when trying to measure market size?

5.) What does Scott mean when he says “resources are like carbs, resourcefulness is muscle”? Why does Scott believe we need to challenge our faith in the strength of resources? What advice does Scott given when founders ask, “when is the right time to raise big”? How has Scott’s writing of the book influenced his mindset when engaging with founders today and investing?

Items Mentioned In Today’s Show:

Scott’s Fave Book: Endurance: Shackleton’s Incredible Voyage to the Antarctic

Scott’s Most Recent Investment: Assembled Brands

As always you can follow Harry, The Twenty Minute VC and Scott on Twitter here!

Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Are you thinking about life insurance in the new year? Ladder Is the smart and easy way to get term life insurance online. With Ladder there are no commissioned agents and no policy fees — you can be done in minutes. Even better, coverage can start today, if you qualify, and you can cancel anytime. Ladder is licensed and backed by trusted partners, with billions in coverage. Visit ladderlife.com to apply and get an instant decision on fully underwritten term life insurance, and check life insurance off your list TODAY.

---

Ready for tax season? Wishing you’d kept a closer eye on your books this year? Set yourself up for success in 2019 with Pilot. Pilot is a bookkeeping company focused on the needs of startups. Their team of SF-based bookkeepers are assisted by engineers to automate the most error-prone parts of bookkeeping, so you know you’re getting an accurate report every month. Plus, Pilot does accrual basis bookkeeping in Quickbooks Online, so you’re never locked into a proprietary platform. Learn more and sign up here. Don’t wait – the first 100 members of the Twenty Minute VC community get 20% off Pilot Core for six months.

 

Andrew Dudum is the Founder & CEO @ Hims, one of the fastest growing consumer brands of our time and the fastest growing men’s health and wellness brand. To date, they have raised over $97m in VC funding from some of the best in the business including Thrive, Founders Fund, Forerunner, IVP, Redpoint and SV Angel just to name a few. Andrew is also Venture Partner at Atomic, a venture-builder backed by Peter Thiel, Marc Andreesen and many of the world’s best investors who recently announced their new $150m fund to start companies solving the world’s problems. Prior to Atomic and Hims, Andrew led Product at TokBox.com, the leader in web-based communication and In 2012 TokBox was acquired by the global telecommunications company Telefonica ($TEF).

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In Today’s Episode You Will Learn:

1.) How Andrew made his way into the world of startups, came to build a venture builder backed by Thiel and Andreesen before starting the fastest growing men’s health and wellness brand in Hims?

2.) How does Andrew view the world of online and offline marketing in today’s proliferated D2C space? What were the core elements that allowed Hims to achieve such success with their branding? How does Andrew respond to suggestions that there is a lack of free and open distribution due to incumbents paying up for traditional channels making CAC unachievable for startups? How does Andrew look to solve for this?

3.) What does Andrew believe it is that has allowed Hims to execute faster than any other D2C brand in history? How does Andrew distinguish between people and process when considering the scaling at different stages of the business? What are the pros and cons of having such constraints on headcount? When is the right time to pour fuel on the fire?

4.) Hims raised their last round at a $200m valuation in less than a year of operating, how did Andrew evaluate this one? Does this not effectively price Hims out of the majority of M&A?  What leads Andrew’s thesis with his suggestion that he thought the valuation was “quite frankly, a great price for investors”? What advice would Andrew have for founders entering the fundraising process?

5.) Andrew is also the co-founder @ Atomic, so what really is a venture builder? How have Atomic built a framework around idea generation? How do Atomic determine which ideas to pursue and which to disregard? How does data and benchmarking play a central role in this process?

Items Mentioned In Today’s Show:

Andrew’s Fave Book: Creativity Inc

As always you can follow Harry, The Twenty Minute VC and Andrew on Twitter here!

Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Much like how Carta changed how private companies manage their cap tables and 409A valuations, Carta are now doing the same for fund administration. With Carta’s new, modern fund administration software and services, you get a real-time dashboard of your general ledger, can securely share info with your LPs, and issue capital calls–from the same platform, you accept securities and request cap table access. So essentially, Carta simplifies how startups and investors manage equity, fund administration, and valuations. Go to carta.com/20VC to get 10% off.

Ted Wang is a Partner @ Cowboy Ventures, one of Silicon Valley’s leading early-stage funds with the likes of Philz Coffee, Dollar Shave Club, Brandless, DocSend, Accompany and Brit + Co all in their portfolio. As for Ted, prior to VC, Ted spent X years as a leading Silicon Valley lawyer with Fenwick & West where he worked with some of the most notable companies of our times including Facebook, Dropbox, Twitter, Square and Spotify just to name a few. Ted also created the Series Seed Documents – a set of open-sourced financing documents posted on Github used by thousands around the world today.

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In Today’s Episode You Will Learn:

1.) How Ted made his way from one of the most renowned lawyers in the valley with Fenwick & West to partner @ Cowboy alongside Aileen Lee?

2.) How does Ted fundamentally approach risk today? Given this mindset, how does this impact Ted’s thinking on optimizing portfolio construction? On the flip side, how has Ted seen many founders wrongly approach the theme of risk? What is the question they need to be asking? What is Ted’s story about risk related to his time working with Jet?

3.) What is it that makes Ted believe that “advice is often oversimplified”? If so, how can VCs provide tangible advice to their portfolio companies today? How can founders determine what is the right advice to accept and integrate vs listen and disregard? How does this lead Ted’s thinking on the 2 core value adds a VC can provide? What advice did Dropbox Founder, Drew Houston give Ted on when to accept advice?

4.) What does Ted mean when he says “there are 4 parts to venture”? How does Ted think about the theme of learning and self-improvement when assessing founders? How does he look to do this pre-investment? What questions reveal the most? Applying it to himself, where will Ted place his biggest efforts on learning within the realm of venture over the next 12 months?

Items Mentioned In Today’s Show:

Ted’s Fave Book: 7 Habits of Highly Effective People

Ted’s Most Recent Investment: Fullcast

As always you can follow Harry, The Twenty Minute VC and Ted on Twitter here!

Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Much like how Carta changed how private companies manage their cap tables and 409A valuations, Carta are now doing the same for fund administration. With Carta’s new, modern fund administration software and services, you get a real-time dashboard of your general ledger, can securely share info with your LPs, and issue capital calls–from the same platform, you accept securities and request cap table access. So essentially, Carta simplifies how startups and investors manage equity, fund administration, and valuations. Go to carta.com/20VC to get 10% off.

Dave Vasen is the Founder & CEO @ Brightwheel, the child management software solution you need and now the #1 platform for early education. To date, with Brightwheel, Dave has raised over $33m in funding from some of the best in the business including Bessemer, GGV Capital, Lowercase Capital, Chan Zuckerberg Initiative, our friends at Eniac Ventures and then the likes of Mark Cuban and Chris Sacca. As for Dave, prior to Brightwheel, he was a VP of Product @ AltSchool and before that spent 3 years at Amazon in numerous different roles including Head of K-12 Education on Kindle and developed and launched the “Made for Kindle” licensing program – both domestic and global.

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In Today’s Episode You Will Learn:

1.) How Dave made his way into the world of edtech and startups from being a consultant at Bain and product manager at Amazon?

2.) Why does Dave fundamentally disagree that founders should always be raising? What is the right way that founders should approach the fundraise? How can founders turn down investor meetings politely when requested and they are not raising? What is the right way to think about capital as a weapon today and the effective allocation of it?

3.) Why does Dave disagree with many elements that the Founder/VC relationship is a marriage? What one element, other than capital, does Dave most look for in a potential investor? What can founders do to really compress the fundraise timeline? How can founders build relationships with VCs under these compressed conditions?

4.) In the valley there is a large amount of glorification around the scaling and founding of companies, how does Dave feel personally about this glorification? How would Dave like to see this mindset fundamentally change? In terms of mindsets, why does Dave push back against the suggestion of VC “pattern recognition”? How has being an older founder and father changed the way he thinks about building Brightwheel today?

5.) How does Dave interpret the meaning of focus today with regards to company building? How does Dave determine the elements to really double down on? How does Dave think about saying no to opportunities? What framework does he use? What have been some of Dave’s biggest learnings on culture and being prescriptive around it?

Items Mentioned In Today’s Show:

Dave’s Fave Book: The Five Dysfunctions of a Team: A Leadership Fable

As always you can follow Harry, The Twenty Minute VC and Dave on Twitter here!

Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Much like how Carta changed how private companies manage their cap tables and 409A valuations, Carta are now doing the same for fund administration. With Carta’s new, modern fund administration software and services, you get a real-time dashboard of your general ledger, can securely share info with your LPs, and issue capital calls–from the same platform, you accept securities and request cap table access. So essentially, Carta simplifies how startups and investors manage equity, fund administration, and valuations. Go to carta.com/20VC to get 10% off.

Anu Duggal is the Founding Partner @ Female Founders Fund, a leading early-stage fund investing in female-founded technology companies. Within their incredible portfolio is the likes of Zola, Rent The Runway, Maven Clinic, Tala and previous guest, Rockets of Awesome. They also have the most incredible mentor network including the founders of Stitchfix, Care.com, Zola and Tala. Prior to founding Female Founders Fund Anu was CEO @ Doonya, a dance fitness and media company inspired by Bollywood and fun fitness. Before that, Anu was Founder @ Exclusively.In where she headed up New Business Development.

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In Today’s Episode You Will Learn:

1.) How Anu made her way into the world of VC with her founding of Female Founders Fund?

2.) What does Anu mean when she says she likes to focus on “non-obvious opportunities”? What are some clear examples of this? These non-obvious opportunities often appear to have smaller markets, how does Anu think about market size and evolution when investing? Can one blame male VCs for sometimes not identifying with the problem set being solved? What can be done to solve this problem?

3.) What 3 elements do Anu most look for when investing in consumer today? How does Anu respond to the statement that consumer may produce healthy revenue but at the end of the day they will never really produce venture return and be sold for 1.6x EBITDA? How does Anu assess the state of the M&A market today in the world of CPGs?

4.) How was the first fundraising for Female Founders Fund? What did the process look like in terms of amount of meetings, total committed LPs and duration spent raising? What were the common pushbacks from LPs in the fundraise? What did Anu do well that she would do again? How did the raise of the 2nd fund compare to the raise of Fund I?

5.) What does Anu mean when she states, “the power of the female network”? How has Anu seen this work in the real world? How does this allow Anu to see the best deals? How does Anu think about scaling check size and ownership with fund II? How does Anu think about reserve allocation when re-investing?

Items Mentioned In Today’s Show:

Anu’s Fave Book: Educated: The international bestselling memoir

Anu’s Most Recent Investment: Co-Star, Hyper-Personalized, Real Time Horoscopes

As always you can follow Harry, The Twenty Minute VC and Anu on Twitter here!

Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Much like how Carta changed how private companies manage their cap tables and 409A valuations, Carta are now doing the same for fund administration. With Carta’s new, modern fund administration software and services, you get a real-time dashboard of your general ledger, can securely share info with your LPs, and issue capital calls–from the same platform, you accept securities and request cap table access. So essentially, Carta simplifies how startups and investors manage equity, fund administration, and valuations. Go to carta.com/20VC to get 10% off.

Anand Sanwal is the Founder & CEO @ CB Insights, the tech market intelligence platform that ingests massive datasets, to answer complex questions and predict future trends. CB is the 9th best place to work in the US according to GlassDoor and one of the fastest growing SaaS companies in the US. To date, CB Insights has raised over $11m in VC funding, a topic Anand discusses at length in our episode today! Prior to founding CB, Anand held numerous roles at American Express including running a $50m Innovation Fund and managing the company’s discretionary investment spend ($4-5Bn p.a.). Before American Express, Anand was one of the early team @ Kozmo.com, one of the most well-funded and infamous startups in NYC history.

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In Today’s Episode You Will Learn:

1.) How Anand came to found CB Insights from running American Express’ $50m Innovation fund and the a-ha moment there?

2.) Why does Anand believe that revenue funding is the best kind of funding? What 3 elements does Anand believe it fundamentally allows? What does Anand mean when he says “most have 3 masters, you can only serve two of them at once”? Does Anand believe that founders today are treating their investors as customers?

3.) How does Anand distinguish between business that can be funded from revenue vs those that cannot? How does Anand think about the relationship between growth and margin? Why does it make sense for VCs today to push for the suggestion that startups need to raise big to grow? How can founders think about and respond to this?

4.) Why does Anand believe that most B2B content today is crap? What are the core pillars that make great B2B content today? How does Anand think about potentially going too far when it comes to the risque nature of the content? What advice would Anand give to B2B founders wanting to ramp up their game in content? Where do many go wrong?

5.) What does Anand mean when he says that “pedigree is often overrated”? How has that led Anand’s thinking when building out the team at CB? Where does Anand see most founders make mistakes when it comes to both team and company scaling? What interview question does Anand find most revealing of an individuals’ character?

Items Mentioned In Today’s Show:

Anand’s Fave Book: Influence: The Psychology of Persuasion

As always you can follow Harry, The Twenty Minute VC and Anand on Twitter here!

Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Much like how Carta changed how private companies manage their cap tables and 409A valuations, Carta are now doing the same for fund administration. With Carta’s new, modern fund administration software and services, you get a real-time dashboard of your general ledger, can securely share info with your LPs, and issue capital calls–from the same platform, you accept securities and request cap table access. So essentially, Carta simplifies how startups and investors manage equity, fund administration, and valuations. Go to carta.com/20VC to get 10% off.

Danny Rimer is a Partner @ Index Ventures, one of the world’s leading venture funds with a portfolio including the likes of Dropbox, Skype, King, Bird, Slack and many more incredible companies. As for Danny, he is known for his investments in Dropbox, leading the company’s Series B, Etsy, King (makers of world famous, Candy Crush), Skype and more recently many retail and fashion businesses such as Farfetch, Glossier and GOAT. He’s been on the coveted Forbes Midas List for more than a decade and in 2017 was appointed an Officer of the Order of the British Empire (OBE) for services to business and charity and the New York Times included him in its list of the top 20 venture capitalists worldwide.

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In Today’s Episode You Will Learn:

1.) How Danny made his way into the world of venture and came to be a Partner @ Index Ventures?

2.) Having backed the likes of King, Skype, Glossier, how does Danny respond to Peter Fenton and Jeremy Levine’s suggestions of a “consumer downturn”? Does Danny believe there is a lack of free and open distribution today? Can startups compete with such inflated CACs? Henry Davis @ Glossier asks: how have you seen acquisition models change over time? How do you envision acquisition models of the future?

3.) Peter Fenton said on the show previously, he always laughs when he hears VCs say they like big markets, how does Danny assess market sizing today? What have been Danny’s biggest lessons on assessing market size when looking at his portfolio? How does Danny think about niche markets today in such an Amazon dominant world? How does Danny assess price today? How does Danny determine when to stretch vs stay firm?

4.) Having helped many companies scale to global success, what does Danny believe to be the core considerations in getting your startup ready for global expansion? How did Danny find Index’s expansion when opening up their first US office in 2011 in SF? What were some of the biggest challenges? How does Danny think about and assess generational transition within venture and Index more specifically today?

5.) Danny has spent over 3,000 hours on boards to date, how has Danny seen himself evolve as a board member over that time? What were some inflection moments in those hours that fundamentally changed the way Danny thinks? What advice would Danny give me, having just gained my first institutional board seat?

Items Mentioned In Today’s Show:

Danny’s Fave Book: Killing Commendatore by Haruki Murakami

Danny’s Most Recent Investment: Goodeggs

As always you can follow Harry, The Twenty Minute VC and Danny on Twitter here!

Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Much like how Carta changed how private companies manage their cap tables and 409A valuations, Carta are now doing the same for fund administration. With Carta’s new, modern fund administration software and services, you get a real-time dashboard of your general ledger, can securely share info with your LPs, and issue capital calls–from the same platform, you accept securities and request cap table access. So essentially, Carta simplifies how startups and investors manage equity, fund administration, and valuations. Go to carta.com/20VC to get 10% off.

Tom Blomfield is the Founder & CEO @ Monzo, in it’s simplest words, the bank of the future allowing you to open a full UK bank account in minutes, from your phone. To date, Tom has raised over $190m in funding for Monzo from the likes of Thrive, Accel, General Catalyst, Stripe, Mike Moritz and Goodwater just to name a few. As for Tom, prior to Monzo he was the Co-Founder of another of London’s rocketship startups in the form of GoCardless and before that co-founded student marketplace Boso.com alongside Triplebyte Founder, Harj Taggar.

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In Today’s Episode You Will Learn:

1.) How Tom made his way into the world of startups from University and came to found the bank of the future in Monzo?

2.) Why does Tom believe that scaling a company today can really be broken up into 3 distinct phases? What are those phases? How does what one needs for each phase differ accordingly? What elements has Tom found most challenging to navigate in the scale-up phase? Are there challenges or elements that are the same across every company?

3.) Why does Tom believe that product decision-making is both an art and a science? How does Tom determine when is the right time to add ancillary products? How can one really stress-test true customer love for the first product? How does Tom balance between product expansion vs geographical expansion? How does Tom balance between being customer-driven vs customer informed?

4.) Tom has grown Monzo to 1.2m users with virtually no advertising, how does Tom respond to the statement that there is a lack of free and open distribution today? What does Tom mean when he says “when it comes to customer acquisition you have to play a different game”? In building community, what have Monzo done so right? Where have they made mistakes? What have been some big lessons on early community building?

5.) Having raised over $190m in VC funding, what have been some of Tom’s biggest lessons when it comes to fundraising? Why does Tom believe that so few boards are managed and run well? Where do they go wrong? What do great board managers do to run an efficient process? What does Tom mean when he says “use board meetings as a tool to instil operational excellence?”

Items Mentioned In Today’s Show:

Tom’s Fave Book: The Hard Thing About Hard Things by Ben Horowitz

As always you can follow Harry, The Twenty Minute VC and Tom on Twitter here!

Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Laura Deming is Founding Partner @ The Longevity Fund, the first VC firm dedicated to funding high-potential longevity companies. To date, Laura has raised $26m across 2 Longevity funds and has backed the likes of Unity Biotechnology, Precision Biosciences, Metacrine, Navitor, and Alexo Therapeutics. Prior to Longevity, Laura was accepted to MIT at the age of 14 to study physics and then dropped out to join the Thiel Fellowship and start The Longevity Fund. If that wasn’t enough, Laura most recently founded Age1, a four-month startup accelerator program focused on founders creating longevity companies.

Jeff Morris Jr is the Founder of Chapter One, an early stage seed fund investing in blockchain assets, mobile and subscription businesses. Chapter One’s Portfolio includes the likes of Lyft, Brandable, Crypto Kitties and many more incredible companies. However, Jeff is unique as Chapter One is only one of his hats, Jeff is also the Director of Product & Revenue @ Tinder and when asked to lead the revenue team they were ranked #17 in the app store. Within a year, under Jeff’s leadership, Tinder became the #1 top grossing app in the world.

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In Today’s Episode You Will Learn:

1.) How Jeff made his way into the world of startups and angel investing, how that lead to his role as Director of Product and Revenue @ Tinder and a leading early-stage investor with Chapter One?

2.) Jeff has previously said, “apply an investor mindset to every product decision I make”. What are the foundational questions involved? What are the inherent challenges of being so deep in product and investing simultaneously? What does Jeff think of VCs giving product advice to founders? What should the founders look for? What advice does Jeff give to the common question of “how do I get into investing and VC”?

3.) Why does Jeff disagree with the platform shift and the downturn in consumer mobile? What core innovations will drive the next wave of consumer mobile? Valuations in the space are often lofty, how does Jeff think about price and evaluate his own price sensitivity? How does Jeff think about scalable customer acquisition today in a world where incumbents dominate and price up the traditional channels?

4.) Jeff has said before that “investors treat crypto teams as if they are superhuman”, what makes Jeff think this? How do their interactions differ than towards non-crypto teams? Why are lofty expectations dangerous for valuations? How does that put undue pressure on employees? Why are lofty expectations dangerous for product development? How do they affect the product roadmap negatively?

5.) How does Jeff approach the diligence aspect when it comes to investing? What have been some of his major lessons from making over 35 investments on the right diligence framework? How do shortened fundraising cycles negatively affect investor diligence processes? What can founders and investors do under these constrained time frames?

6.) Having worked with some of the greats from Doug Leone to Bill Gurley, what are some of the common traits in how the very best investors engage with founders? What were Jeff’s personal learnings from seeing these greats in action? How did it change the way Jeff thinks about founder interaction and engagement?

Items Mentioned In Today’s Show:

Jeff’s Fave Book: The Catcher In The Rye, Googled

Jeff’s Most Recent Investment: Radar Relay

As always you can follow Harry, The Twenty Minute VC and Jeff on Twitter here!

Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Leo Polovets is a General Partner @ Susa Ventures, one of the valley’s leading early-stage seed funds with a portfolio including the likes of Flexport, Robinhood, Lendup, Qadium, Rigetti, the list goes on. As for Leo, prior to joining the world of VC, he started his career as the second non-founding engineer at LinkedIn. After two years at LinkedIn, Leo spent 3 years at Google, largely working on real-time payment fraud detection. Finally, his last stop pre-Susa involved spending 4 years at Factual, a location data platform.

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In Today’s Episode You Will Learn:

1.) How Leo made his way into the world of VC from being the 2nd non-founding engineer at LinkedIn?

2.) Why does Leo believe that the hailed “warm intro” is actually dumb? What are the biggest drawbacks to this being commonplace in our ecosystem? What does Leo believe the mindset of investors should be instead? How does Leo filter through cold inbound? What are the 4 elements Leo looks for in all inbound? What can founders do to really make them stand out?

3.) Leo has previously heavily emphasised the importance of moats, how does Leo define moats and defensibility? When do founders have to think about moat building? Pre-product? Pre-launch? Pre-scaling? What questions suggest that a founders mindset is heavily oriented to moat building? With the majority of incumbents being usurped by platform shifts, does that not render moats significantly futile in the long term?

4.) What does Leo believe is the right way for investors to pass on an opportunity and communicate that to founders? What is wrong with the current way many do it? How does Leo present his opinion without getting into an argument with the founder on reasoning? What feedback has Leo been given from founders that has changed the way he thinks about being an investor?

5.) Controversial capitals Round:

• Ownerships is built on first check? Agree or disagree and why?
• Whether it is a $6m, $8m or $12m, if it is at seed, it is so early that price really does not matter so much? Agree or disagree and why?
• There is no point VCs spending their time with struggling companies in the portfolio. At best they return cents on the dollar. Only work with the outperformers to drive returns. Agree or disagree and why?

Items Mentioned In Today’s Show:

Leo’s Fave Book: Elad Gil’s High Growth Handbook

Leo’s Most Recent Investment: Interviewing.io

As always you can follow Harry, The Twenty Minute VC and Leo on Twitter here!

Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

 

 

Ooshma Garg is the Founder & CEO @ Gobble, the startup that allows you to cook a fresh homemade dinner in just 15 minutes. To date, Ooshma has raised over $30m in funding for Gobble from some of the best in the business including Initialized Capital, Keith Rabois, Reid Hoffman, Founder Collective, Felicis, Andreesen Horowitz and Thrive just to name a few. As for Ooshma, prior to founding Gobble she founded Anapata, an online site that matches students looking for jobs with potential employers. The company was ultimately acquired by LawWerx.

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In Today’s Episode You Will Learn:

1.) How Ooshma made her way from Wall St to changing the way America eats with Gobble today?

2.) Everyone has an opinion on the food delivery space with the public nature of Blue Apron, what does Ooshma mean when she says “small and mighty beats loud and weak”? Why did Ooshma not take the path of other competitors in the space of racing big and running fast? What is Ooshma’s advice to founders on dilution and raise amounts?

3.) Would Ooshma agree with Alex @ LSVP that marketing portfolios are like venture portfolios, diversified and then double down? Would Ooshma agree with the concern around unfeasible CACs due to incumbents bidding them up on major platforms? Where does Ooshma see blue ocean when it comes to marketing channel success?

4.) What does Ooshma mean when she says “success is survival”? Why is capital efficiency even more important in online/offline businesses? What are some of Ooshma’s examples of her “wartime approach” to capital efficiency? How does Ooshma explain this more sustainable growth to the growth-hungry VC community? Who is to blame for the insatiable desire for unreasonable growth; the founders or the VCs?

5.) Ooshma has raised over $30m with Gobble, analysing herself in fundraising, what does Ooshma believe she did particularly well during the raise and advise other founders to do? What elements would she like to improve upon for the next round? What is the story behind how Ooshma sprinted down the 101 to get Keith Rabois as an angel?

Items Mentioned In Today’s Show:

Ooshma’s Fave Book: The Wind-Up Bird Chronicle 

As always you can follow Harry, The Twenty Minute VC and Ooshma on Twitter here!

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Avidan Ross is the Founding Partner @ Root Ventures, one of Silicon Valley’s most exciting newer generation of funds dedicated to backing bold engineers at seed. To date they have backed some incredible companies such as Nautilus Labs, Dusty Robotics, Tortuga AgTech and Instrumental.ai just to name a few. Prior to founding Root, Avidan was CTO at The CIM Group, with an aggregate of $15Bn AUM, Avidan was responsible for establishing the company’s technical vision and leading all aspects of the company’s technology investment. Before that, he built algorithmic trading platforms as Director of Technology at WHW Capital. 

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In Today’s Episode You Will Learn:

1.) How Avidan went from building algorithmic trading platforms to back the next generation of revolutionary engineers with Root?

2.) What does Avidan mean when he says “the peace dividends of the autonomous car wars will generate more value outside of transportation?” How does the commoditisation of these core components affect subsequent industries? With their commoditisation, does it not become a raise to the bottom on price and margin?

3.) How does Avidan approach the layering on new software products to emerging hardware devices? What does this mean for the margin required both for the hardware and the software? How does Avidan’s investor mentality alter when investing in hardware vs software?

4.) Why does Avidan believe “old and boring industries are the most exciting to build software in?” How does Avidan approach the common problem of customer education and selling to a customer base that does not want to talk to you and does not believe in your product? What do founders selling in these industries need to focus on to break through?

5.) How does Avidan assess the current landscape in terms of the quality and quantity of engineer CEOs? Why does Avidan believe the MBA CEO will be replaced by engineers? How has Avidan seen a variance in the background in the entrepreneurs innovating in “old and boring” industries?

Items Mentioned In Today’s Show:

Avidan’s Fave Book: Drive by Daniel Pink

Avidan’s Most Recent Investment: Dusty Robotics

As always you can follow Harry, The Twenty Minute VC and Avidan on Twitter here!

Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Ryan Caldbeck is the Founder & CEO @ CircleUp, the startup creating a transparent and efficient market to drive innovation for consumer brands. To date, Ryan has raised over $50m with CircleUp from some friends and prior guests of the show including USV, Collaborative Fund and Canaan Partners just to name a few. Prior to CircleUp, Ryan spent nearly 7 years investing in consumer products with the likes of TSG Consumer Partners and Encore Consumer Capital. As a result of Ryan’s success with CircleUp he has been recognised as a “Titan of Retail” by Bloomberg and “40 Under 40” by the San Francisco Business Times.

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In Today’s Episode You Will Learn:

1.) How Ryan made his way into the world of consumer investing and what the realisation moment was for him that the market needed a solution, CircleUp?

2.) Why does Ryan believe that venture capital has a fundamental problem? What is it about the economics of funds that Ryan has a problem with? Who is to blame for this situation; the LPs who fund it or the AUM hungry VCs? Why does Ryan believe the majority of micro VCs are micro as that is all they could raise? Is that really fair or true?

3.) Why does Ryan fundamentally believe the LP ecosystem and mechanism for backing funds is inherently broken? What is so wrong with current LP incentives? What does Ryan believe can be done to encourage more risk-taking and innovation from within the LP class?

4.) Recognising the antiquated nature of much of VC, what does Ryan believe the future of VC looks like? How will we see the use of data impact both sourcing and investment decision-making? Where does Ryan believe it has the most potential? Where is data so sparse that it will be challenging? How does Ryan believe the best managers of the future will use data?

5.) Consumer brands and DNVBs are riding high today, does Ryan believe we are in a consumer bubble? What does Ryan believe is so wrong about how the majority of the current crop of VCs analyse consumer businesses? How should they be analysed? Why does Ryan believe consumer exits will be smaller? Is it fair to say consumer is more capital intensive and largely sells for 1.6-1.8 EBITDA?

Items Mentioned In Today’s Show:

Ryan’s Fave Book: The Hard Thing About Hard Things

As always you can follow Harry, The Twenty Minute VC and Ryan on Twitter here!

Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

 

Ron Bouganim is the Founding Partner @ The Govtech Fund, the first-ever venture capital fund dedicated to government technology startups. To date, he has backed some incredible category leaders including mark43, Neighbourly, MindMixer and SeamlessDocs just to name a few. Prior to the Govtech Fund, he was Accelerator Director @ Code for America and was an active angel investor and advisor working with more than twenty startups including ShareThrough, HelloSign, PagerDuty, and Close.io.

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In Today’s Episode You Will Learn:

1.) How Ron made his way into the world of technology and startups and became angel investing? How that led to the founding of Govtech Fund and the belief in the space today?

2.) There is the notion that there many challenges to investing in Govtech and scaling companies in the space, how does Ron respond to the suggestion the sales cycles when selling to government are too long for startups to navigate successfully? How does Ron respond to the suggestion that the growth rates in the space are to low for venture returns? How does Ron respond to the suggestion that founders in the space are inherently older as only they have experienced the problems of government tech?

3.) Why does Ron believe that a vertically focused fund is the right strategy is creating a massively outperforming fund? How does Ron respond to the possibility of missing moonshots in alternate categories? What does Ron most look for in the co-investors that he invests with? What do they bring to the table?

4.) What does Ron believe are the 2 fundamental roles of a seed investor today? How does that differ from previous generations of seed funds? Why does Ron believe that fundraising and hiring help is now merely table stakes? What else can seed investors do to meaningfully move the needle for their portfolio?

5.) Why does Ron advocate for a highly concentrated portfolio? How does Ron respond to LP concerns around a lack of diversification? Does Ron believe that you can grow ownership of your best companies over subsequent rounds? What is the sign of success for Ron when the founder comes back for re-financing?

Items Mentioned In Today’s Show:

Ron’s Fave Book: Leonardo Da Vinci by Walter Isaacson

Ron’s Most Recent Investment: Sema: Automated Code Maintenance

As always you can follow Harry, The Twenty Minute VC and Ron on Twitter here!

Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Phil Libin is the Co-Founder & CEO @ All Turtles, the startup that believes they have a better way to make technology products, placing products first and companies later. Today they are building AI products in San Francisco, Paris and Tokyo. As for Phil, prior to All Turtles he was a Managing Director @ General Catalyst. Before that he spent 23 years founding different companies including founding Evernote, taking it from idea generation to productivity powerhouse raising over $160m in VC funding in the process, from some of the very best including Sequoia Capital. Phil is also an extremely successful angel with a portfolio including Gusto, TellApart and Binary Thumb just to name a few.

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In Today’s Episode You Will Learn:

1.) How Phil made his way into the world of tech startups many years ago, how that led to his entering VC with General Catalyst and to now, founding All Turtles?

2.) How does Phil assess the state of Silicon Valley today? Why does Phil believe that Silicon Valley has been becoming increasingly redundant over the last 20 years? Why does Phil argue that the VC Silicon Valley model has been primarily effective at serving it’s own needs? What needs to occur for this to change?

3.) Why does Phil argue that the balance of power between startups and incumbents is shifting for 5 core reasons? Why does Phil believe that the data incumbency argument with AI startups is largely overstated and a fear tactic? How does Phil believe people’s attitude toward working for incumbents has been shifting over the last few years?

4.) Why does Phil believe that the concept of a “company” is fundamentally outdated? What is so broken about this model? What does Phil believe will be the model of the future for the world’s best product creators? Why does the idea of a generalist VC in this model largely not make logical sense to Phil? What does Phil believe the future of VC is?

5.) Why does Phil believe that his time in VC has made him a better CEO than even his time in operations? What have been his core learnings? How has his operating mindset fundamentally shifted? Why does Phil argue the core role of the CEO is not management upscaling? Why does Phil argue it is wrong to assume the only mindset is growth?

Items Mentioned In Today’s Show:

Phil’s Fave Book: Clock of The Long Now

As always you can follow Harry, The Twenty Minute VC and Phil on Twitter here!

Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Linda Xie is a Co-Founder & Managing Director @ Scalar Capital, one of the leading crypto asset funds to have been born over the last few years with Linda becoming one of the most prominent figures in the space. Prior to co-founding Scalar, Linda was a product manager at Coinbase where she worked with regulators and law enforcement. Before Coinbase, she was a portfolio risk analyst at AIG. If that was not enough, Linda is also an advisor to 0x, the critical infrastructure layer in the emerging financial stack built on a foundation of Ethereum token standards.

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In Today’s Episode You Will Learn:

1.) How Linda made her move into the world of crypto joining Coinbase back in 2014 and how that led to her founding of Scalar? What were her biggest takeaways from seeing the first-hand scaling of Coinbase?

2.) What is a privacy coin and why does it matter? What are some of the dominant legitimate uses for privacy coins? From ZCash to Monero to Dash, there are many players in the space, what are some of the core benefits and tradeoffs of each platform? What is the fundamental problem with privacy coins today?

3.) What is a decentralised exchange, why does Linda believe it is inherently important? How does Linda assess the current exchange environment today? Where does she see it moving over the coming years? What have been some of Linda’s biggest learnings advising 0x?  Given the mission and ethos of crypto, does Linda believe that centralised exchanges fundamentally go against the core ethos of the space?

4.) How does Linda perceive the state of ethereum today? What are some of the core challenges facing ethereum today? How does ethereum compare to alternative smart contract platforms? What is their differentiation? Will we see a winner take all/most market within smart contract platforms? Will we see smart contract platforms be regionally fragmented?

5.) How does Linda address the fundamental challenge of valuing tokens today? What has been her preferred model in doing this to date? How does Linda assess the mega raises we have seen over the last year? How does Linda think about preventing projects from raising huge rounds just to stay in step with the mega raises of their competitors?

Items Mentioned In Today’s Show:

Linda’s Fave Book: Sapiens: A Brief History of Humankind

Linda’s Most Recent Investment: Kadena

As always you can follow Harry, The Twenty Minute VC and Linda on Twitter here!

Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Dennis Mortensen is the Founder & CEO @ X.ai, the startup that realises scheduling sucks and provides ridiculously efficient AI software that solves the hassle of meeting scheduling. To date, Dennis has raised over $44m in VC funding from the likes of Firstmark, IA Ventures, Lerer Hippeau, DCM and more fantastic names. As for Dennis, he is an expert in leveraging data to solve enterprise use cases and prior to X.ai he was the Founder & CEO of 3 companies, 2 of which were acquired and one which went bust or as he describes a rather expensive MBA. Dennis is also the author of Data Driven Insights, on collecting and analyzing digital data.

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In Today’s Episode You Will Learn:

1.) How Dennis made his way from Copenhagen to New York, the world of startups and came to found one of the hottest AI companies of our day in X.ai?

2.) What were Dennis’ biggest lessons from enjoying 3 successful exits prior to X.ai? What were Dennis’ learnings from his one failed startup? What would he do differently if he were to start another company? How does Dennis navigate the balance of between pursuing a vision and miss vs when something is just not working?

3.) Does Dennis believe that there really is such a thing as an AI first company? What is the right mentality to approach a company solving a problem through AI with? How does Dennis view the standardisation of AI tools today (Tensor Flow, libraries etc etc)? Does this remove barriers and defensibility for AI companies? What is the key to success for all AI companies?

4.) What does a truly differentiated data acquisition strategy look like? How can one determine the different utility value between different sizes of data? At what point does Dennis believe utility value of data diminishes due to the sheer size of existing data?

5.) Does Dennis believe that conversational UI is truly a paradigm shift in the way we interact with our devices or an iterative improvement? What have been some of the biggest lessons for Dennis in designing conversational UI products? What have been some of the fundamental challenges?

Items Mentioned In Today’s Show:

Dennis’ Fave Book: The Narrow Road: A Brief Guide to the Getting of Money, Shoe Dog: A Memoir by the Creator of NIKE, Mike Tyson: Undisputed Truth

As always you can follow Harry, The Twenty Minute VC and Dennis on Twitter here!

Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

 

 

Phin Barnes is a Partner @ First Round Capital, one of the most prestigious and successful early-stage funds of the last decade with a portfolio including the likes of Uber, Square, Warby Parker, HotelTonight, GOAT, PatientPing, Atrium and more incredible companies. As for Phin, in his own words, he learned the business of startups helping grow AND1 from $15M to $225M in revenue as Creative Director for Footwear, and started his own fitness video-game company, producing Yourself!Fitness, the first game of its kind for Xbox and PlayStation 2 where he built partnerships with the likes of Procter & Gamble and McDonald’s. Phin also writes the most fantastic blog, sneakerheadVC, that really is a must read.

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In Today’s Episode You Will Learn:

1.) How Phin came to be a Partner @ First Round by working for free, with no plans to be a Partner?

2.) What were Phin’s biggest lessons from learning from and observing Josh Kopelman? How does Phin define true success as a VC today? Why is the model of determining success according to returns fundamentally flawed? How does Phin approach the need for VCs to be both curious and competitive? What is the nuance there?

3.) Why does Phin believe that the commonly discussed “pattern recognition” is another term for intellectual laziness? What does Phin do to prevent his forming assumptions on the founders he meets? Why does Phin fundamentally disagree with the common VC habit of looking for weaknesses in founders?

4.) Does Phin agree that we have an oversupply of capital in market today? How does Phin determine when a stretch on price is a stretch too far? Why does Phin think that more emphasis should be placed on the business model that VCs have? What does Phin mean when he says that he is on the “sell side”?

5.) What does Phin mean when he says that “VCs should focus on a founders ability to optimise for learning per dollar spent”? Is cash ever a defensible moat in it’s own right? What does Phin believe is the right way for founders to use capital as a weapon?

6.) How does Phin and First Round think about the right way to allocate reserves effectively? What does that look like in reality? What does the decision-making process look like on re-investments? Why does Phin believe that the framework of “pro-rata is largely lazy?

Items Mentioned In Today’s Show:

Phin’s Fave Book: Writing Down the Bones: Freeing the Writer Within, Boyd: The Fighter Pilot Who Changed the Art of War

Phin’s Most Recent Investment: Ubiquity6

As always you can follow Harry, The Twenty Minute VC and Phin on Twitter here!

Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

 

Patrick Morley is the President and CEO @ Carbon Black, the company that combines unfiltered data collection, predictive analytics, and cloud-based delivery to provide superior endpoint protection. Prior to their IPO in April 2018, Carbon Black had raised over $150m in VC funding from the likes of Sequoia Capital, Accomplice, Kleiner Perkins and Highland Venture Partners just to name a few. As for Patrick, under his leadership, he has taken Carbon Black from startup to market leader with over 800 employees. Before Carbon Black, he was CEO of Imprivata Corporation and held senior leadership positions with six venture-backed software companies, including three that had successful IPOs.

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In Today’s Episode You Will Learn:

1.) How Patrick made his way into the world of startups and came to be CEO @ Carbon Black where he turned a startup into a public company and market leader with 800 employees?

2.) Patrick has previously said “there are 7 key themes to building a great company”, what are those themes? From taking 4 companies public what are the patterns in building a business the right way? How does Patrick look to create a culture of accountability but also with a risk-taking mentality? How does one retain startup culture with scale?

3.) How does Patrick view his role as CEO today? What 3 characteristics do all great CEOs need to embody and then act on? Would Patrick agree that some people are destined for certain stages of a company’s life? How does Patrick determine between a stretch and a stretch too far in a VP? What does that subsequent communication look like?

4.) Mike Dauber @ Amplify previously said on the show “timing kills more startups than dollars”, would Patrick agree with this? How does he view market timing? What advice would Patrick give to founders who are 3-4 years ahead in market? What are the challenges? What are the right ways to communicate the path to timing it right?

5.) Why did Patrick choose this year to take Carbon Black public? What are the fundamental pros and cons of being a public company today? How does Patrick assess the role that VCs played in the building of Carbon Black to IPO? What must investors always remember in their interactions with founders? What must founders be cognizant of when selecting their investors and board members?

Items Mentioned In Today’s Show:

Patrick’s Fave Book: Built To Last: Successful Habits of Visionary Companies

As always you can follow Harry and The Twenty Minute VC on Twitter here!

Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Woody Marshall is a General Partner @ TCV, one of the most successful growth funds of the last decade with a portfolio including the likes of Facebook, AirBnB, Spotify, LinkedIn and many more incredible companies. Woody joined TCV in 2008 and has since led investments in Spotify, Netflix, AirBnB, Peloton, Groupon and the list goes on. Due to this phenomenal success, Woody has been named numerous times to the Midas List by Forbes as one of the industry’s top technology investors. Prior to joining TCV, Woody spent 12 years at Trident Capital, where he focused on the payments, internet, and mobile markets.

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In Today’s Episode You Will Learn:

1.) How Woody made his way into the world of VC over 23 years ago and came to invest in products of a generation such as AirBnb, Spotify and Netflix?

2.) What have been the foundational changes Woody has seen over his last 23 years in venture? How did witnessing the boom and bust affect his operating and investing mentality? How does Woody approach price sensitivity? When is stretching on price a stretch too far?

3.) How does Woody analyse and assess the extended period of privatisation for companies today? How does the mega raises of funds from Softbank, Sequoia, GC, Lightspeed etc change the competitive landscape for Woody? Is there a surplus of capital in market today? Why does Woody believe the pie is larger than it has ever been?

4.) Does Woody agree that the dominant role of CEO is management upscaling? From Woody’s portfolio, on hearing this, who is the first CEO that comes to mind and what is the story behind it? What are the mistakes that CEOs tend to make most often when scaling into hypergrowth? What are the 2-3 things that all companies need to focus on when product market fit is apparent and they need to scale?

5.) Woody has spent over 3,500 hours in the board seat, how has he seen himself evolve and develop over time as a board member? What were the biggest learning curves and points of development for Woody? How do the best founders manage and operate their board? Who exemplifies this best from recent memory? What do they do?

Items Mentioned In Today’s Show:

Woody’s Fave Book: The Boys in the Boat

Woody’s Most Recent Investment: Peloton

As always you can follow Harry, The Twenty Minute VC and Woody on Twitter here!

Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Afton Vechery is the Co-Founder & CEO @ Modern Fertility, the startup that guides you through your fertility hormones now so you have options later. To date they have raised over 7m in funding from some of the leading players in venture including USV, First Round Capital, Maveron, SV Angel and Y Combinator. As for Afton, prior to Modern Fertility, Afton was a Product Manager @ 23andMe where she was the sole product manager responsible for all consumer-facing genetic tools.Before 23andMe, Afton was a Strategy and Finance Consultant @ Willow Pump where she participated in fundraising that led to successful $15M fundraise.

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In Today’s Episode You Will Learn:

1.) How Afton made her way into the world of startups with 23andMe and then came to change the way we think about fertility with Modern Fertility?

2.) Afton has previously emphasised the importance of having “frameworks for success”. What does that mean? How do those frameworks break down? How does Afton think about the decision-making process around prioritisation? How does Afton think about the difference between being customer informed and customer driven?

3.) Why does Afton believe that there are times when you should not test the MVP? Why is this? What would Afton do differently in the MVP process if she had her time again? How does Afton think about and respond to the statement “move fast and break things”?

4.) Why does Afton believe it is important to let everyone “rip apart your business”? What are the fundamental benefits of this? From the ripping aparts, Afton has experienced, what have been the biggest takeaways? What was their argument? How did Afton respond? How did her thinking and mentality change as a result?

5.) Why does Phin Barnes @ First Round say Afton is “hard as nails”?  What were some of Afton’s biggest learnings from her early engineering role? How does Afton think about entrepreneurial resilience today? What advice does Afton give to emerging entrepreneurs and first-time founders?

Items Mentioned In Today’s Show:

Afton’s Fave Book: Motherhood Rescheduled

As always you can follow Harry, The Twenty Minute VC and Afton on Twitter here!

Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Rebecca Kaden is a General Partner @ Union Square Ventures, one of the most successful funds of the last decade with a portfolio including the likes of Twitter, Twilio, Zynga, Soundcloud, Tumblr, Lending Club and many more. As for Rebecca, prior to USV, Rebecca was a General Partner @ Maveron, a consumer-only seed and series A fund where she invested in the likes of Allbirds, Dia & Co, Periscope, Earnest and Eargo just to name a few. Before Maveron, Rebecca took the route of many great VCs and was a journalist, working as Special Projects Editor @ Narrative Magazine.

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In Today’s Episode You Will Learn:

1.) How Rebecca made her way into the world of VC from journalism? How her journey with Maveron led to her becoming a General Partner with the prestigious USV?

2.) Having mastered the craft of VC in the world of consumer, how does Rebecca respond to Peter Fenton and Jeremy Levine’s statement, “we are in a consumer downturn”? How does Rebecca think about the lack of free and open distribution today? How can startups compete with incumbents for cost-efficient customer acquisition?

3.) How does Rebecca evaluate the role of Amazon today? How does Rebecca look to get comfortable that Amazon is not moving into the space of a portfolio company? Does Rebecca agree, “if you are not a top 3 priority”, you have a couple of years on them? How can startups learn from the execution advantage shown by Amazon over the last decade?

4.) With several recent consumer acquisitions under $200m, does Rebecca still believe that venture returns can be made at scale in consumer? How does Rebecca analyse how to think about multiple on revenue when evaluating consumer companies? Why Does Rebecca believe we are in a moment of fragmentation, not consolidation?

5.) How does Rebecca compare the partnerships of US and Maveron having been a GP now at both firms? What are the similarities? What are the differences? What does Rebecca believe are the core advantages of small partnerships and controlled fund sizes? How does the addition of the thesis-driven investing style effect Rebecca’s thinking?

Items Mentioned In Today’s Show:

Rebecca’s Fave Book: Pale Fire 

Rebecca’s Most Recent Investment: Modern Fertility

As always you can follow Harry, The Twenty Minute VC and Rebecca on Twitter here!

Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Maynard Webb is truly unique, he has worn 3 different hats and excelled in all of them. First, he is the Founder of The Webb Investment Network, the institutionalisation of his personal investing where he has invested in the likes of Zuora, GOAT, WePay, Okta, PagerDuty and many more incredible companies. He is also a Co-Founder and Board Member at Everwise, the startup that helps companies tailor, scale and run training at enterprise scale. Everwise has raised over $26m in funding from the likes of Sequoia Capital and Canvas Ventures. Finally, Maynard sits on the board of some of the biggest companies of our time including Salesforce and Visa. Previously Maynard was Chairman of the Board of Yahoo!, CEO of LiveOps, and COO of eBay.

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In Today’s Episode You Will Learn:

1.) How Maynard made his way into the world of startups and came to invest in his first company, founded by Sequoia’s Jim Goetz and how that led to eBay, LiveOps and more?

2.) Does Maynard believe we have an excess supply of capital in the market today? What does Maynard think of the mega $Bn+ funds being raised on a frequent basis? How does this distort pricing in the market? How does Maynard think about his own price sensitivity? What does this mean for his available reserve allocation?

3.) Does Maynard believe that the dominant role of CEO is management upscaling? How does Maynard advise on the transition from manager to inspirational leader? How do the vest best CEOs hire the very best execs? How does Maynard know when a stretch VP is a stretch too far? How should founders determine and approach “bet the company” decisions?

4.) When should a founder start installing their board? What does Maynard believe is the optimal board construction, both in characters and profiles? How has Maynard seen his own style of board membership changed over the years? What are the best board members talk to listen ratios? How can founders create alignment among their board?

5.) What is the right way for founders to deal with “s*** hit the fan moments”? What is the framework to approach this with? Where do many go wrong in their approach? How does one communicate this to the wider team, investors and board? What have been Maynard’s biggest personal learnings here from eBay?

 

Items Mentioned In Today’s Show:

Maynard’s Fave Book: The Better Angels of Our Nature

As always you can follow Harry, The Twenty Minute VC and Maynard on Twitter here!

Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Sarah Tavel is a General Partner at Benchmark, one of the world’s leading VC funds with a portfolio including the likes of Twitter, Uber, Snapchat, eBay, WeWork, Yelp and many more revolutionary companies of the last decade. As for Sarah, Sarah has led Benchmark’s investments in and currently sits on the boards of Chainalysis and Hipcamp. Prior to Benchmark, Sarah was a Partner at Greylock Partners, where she led Greylock’s investment in Sonder and another (unannounced) company. Before Greylock, Sarah was one of the first 35 employees at Pinterest where she led the company’s international expansion and aided in the closing of the Series C financing. Sarah was also the product lead for search, recommendations, machine vision, and pin quality and led three acquisitions as she helped the company scale through a period of hyper-growth.

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In Today’s Episode You Will Learn:

1.) How Sarah made her first foray into the world of venture with Bessemer over 10 years ago? How that led to Pinterest and how she came to be a GP at Benchmark today?

2.) Speaking of Sarah’s operating career with Pinterest, Pat Grady said on the show “never has the rate of decay on operating experience been greater”. How does Sarah think about and respond to this? How has operating made Sarah a strong investor? What are the drawbacks that this operating experience can present for investors?

3.) Moving to evaluation, Andy Rachleff, Founder @ Benchmark said on the show, “good team poor market, market wins; good market, poor team, market wins. How does Sarah think about the balance between founder vs market? Why is going after big markets so hard? What should investors look for in a market with that in mind? How does Sarah determine the right time to open up adjacent markets?

4.) There has never been a greater supply of capital in the market than today, does Sarah believe we have an excess supply today? Does Sarah agree with her Partner, Peter Fenton, “no good deal is too expensive in hindsight”? How does Sarah assess her own price sensitivity? How does it depend on the opportunity? How has it changed over time?

5.) Having 2,5000 hours on boards, how has Sarah seen herself develop and change as a board member? What have been some of the biggest learning curves? What are the commonalities in the very best board members Sarah works with? how doe the best entrepreneurs manage and use their boards effectively?

6.) Why does Sarah think that crypto today is very much like the world of adtech in the early days? How does Sarah think about the requirement for specialisation in the space? WIll this be a game for the specialised crypto funds or can generalist VC funds compete?

Items Mentioned In Today’s Show:

Sarah’s Fave Book: Creating the Kingdom of Ends

Sarah’s Most Recent Investment: Hipcamp

As always you can follow Harry, The Twenty Minute VC and Sarah on Twitter here!

Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

 

Amol Deshpande is the Co-Founder and CEO at Farmers Business Network, the farmer-to-farmer agronomic information network improving the livelihood of farmers by making data useful and accessible. To date, they have raised a whopping $193m in funding from the likes of Kleiner Perkins, T Rowe, GV, Temasek and more. As for Amol, prior to founding FBN, he was a Partner @ Kleiner Perkins where he was a partner on the early stage investing team.  Prior to joining Kleiner,  Amol was at Cargill and Black River Asset management and was an entrepreneur in the agriculture sector.

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In Today’s Episode You Will Learn:

1.) How Amol made his way into the world of startups, came to be a Partner @ Kleiner Perkins and then came to change the world of farming with Farmers Business Network?

2.) What were Amol’s biggest takeaways from his time with Kleiner? Although important to think really big, how does Amol think about the Peter Thiel School of Thought, starting in a very small niche and expanding? Where does Amol see many founders go wrong when it comes to market size and assessment?

3.) How does Amol believe the very best CEOs hire the very best talent? What core characteristics does Amol look for when adding to his exec team? What are the leading questions and indicators that would excite/concern Amol? Why does Amol believe the smartest people do not always make the best hires? What are the core signs that a stretch VP is a stretch too far?

4.) What is the key to success for founders in building credibility with customers, investors and their board? What is the most challenging element of credibility building? Where does Amol see many founders go wrong and lose credibility today? How does your approach have to alter according to which class of individual you are looking to build with?

5.) How does Amol fundamentally approach the topic of capital efficiency? What does Amol believe is the right way for founders to think about dilution when raising? How does Amol determine when is the right time to raise big and pour fuel on the fire?

Items Mentioned In Today’s Show:

Amol’s Fave Book: Team of Rivals: The Political Genius of Abraham Lincoln

As always you can follow Harry, The Twenty Minute VC and Amol on Twitter here!

Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

David Frankel is Managing Partner @ Founder Collective, one of the leading seed funds of the last decade with a portfolio including the likes of Uber, PillPack, Coupang, Hotel Tonight, Venmo, Buzzfeed and many more incredible companies. David himself sits on the board of PillPack, Olo, Adhawk and SeatGeek. Prior to founding Founder Collective, David was the Co-Founder and CEO of Internet Solutions, one of the largest ISP providers in Africa. This led to his entrance into angel investing where he enjoyed immense success investing in the likes of Chris Dixon’s Hunch and Alex Rampell’s TrialPay, just to name a few.

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In Today’s Episode You Will Learn:

1.) How David made his way into the world of startups and angel investing from founding Africa’s largest ISP provider and how that led to his founding of Founder Collective?

2.) Does David agree with Andy McLoughlin on the inherent mindset shift required when moving from angel to institutional investor? What does David believe is the key to making a new venture partnership work well in the early days? How was the process between him and Eric Paley? What were some of the core challenges/ highlights and breakthroughs?

3.) What does founder-market fit truly mean to David? Why does David believe it is one of the most crucial elements to look for in all investment opportunities? How was this so perfectly evident in the case of Elliot and TJ @ PillPack? How does David navigate the balance between the perfectness of the fit and the investability of the market?

4.) From watching TJ and Elliot at PillPack, what does David believe the truly special founders do to continuously attract the best talent? When does David believe is the right time to really build out the exec team? How did Elliot and TJ align their scaling of the org chart with the growth of the business so well?

5.) How does David think about the lack of free and open distribution in acquiring new customer in a capital efficient manner today? Why does David believe the companies of the future will be advantaged in distribution? In what shape and form can this advantage take? How does David think about the right time to put the pedal to the metal and aggressively grow?

Items Mentioned In Today’s Show:

David’s Fave Book: Sapiens: A Brief History of Humankind

David’s Most Recent Investment: Adhawk

As always you can follow Harry, The Twenty Minute VC and David on Twitter here!

Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

The reality is that hiring amazing developers is hard. Terminal.io is your dedicated partner in rapidly standing up world-class remote technical teams. How do they deliver both speed and quality? Terminal does this by focusing on everything necessary to successfully source, setup, and support these teams – from physical elements like beautiful workspaces and equipment to ongoing resources like HR, payroll, legal, professional learning and development. But don’t take my word for this, take the word of Eventbrite, former 20VC guest Hims, and Dialpad – all customers and lovers of Terminal. You can find out more today at Terminal.io.

Howard Lerman is the Founder & CEO @ Yext, the company that allows you to control your brand experience across the digital universe. Due in part to Howard’s incredible leadership of the firm, Yext went public in April 2017 with an opening price of $11 a share, today the stock price sits at $26.85 and a market cap of $2.65Bn. Prior to the IPO, Yext raised over $117m in VC funding from Insight Venture Partners, IVP, SV Angel and CrunchFund to name a few. As for Howard, Yext is his 4th company and he is also Co-Founder and Chairman of Confide, a leading off-the-record messaging service.

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In Today’s Episode You Will Learn:

1.) How Howard made his way into the world of startups and came to Partner with is co-founders to start the now public company that is Yext?

2.) Why must every founder know about Teddy Roosevelt and his “Five Minute Meetings”? Literally, what is the right way to structure these meetings? What one question is the right question to ask? How can a leader look to retain that startup culture and ethos with scale? Why does Howard believe running a global company is like running a country?

3.) What have Howard’s biggest takeaways been from studying “John Lennon’s Storytelling Trick”? How can founders use this trick both to inspire their team more effectively internally and then to present a better vision for the company, externally?

4.) Howard has said before “fundraising is not an end in itself”. Does Howard believe that company financing should be celebrated? How was the IPO process for Howard? From a literal standpoint, how does the process run? How did Howard choose which banks to work with? How did the 10-day roadshow shape up? How did the pricing decision-making process look the night before IPO?

5.) Why does Howard believe it is fundamentally better being a public company? What does “public” status allow you? How does being public introduce a challenge never before seen to founders? Why must founders always examine the motives of the VC behind whether they are pushing them to remain private or go public?

Items Mentioned In Today’s Show:

Howard’s Fave Book: Five Stars: The Communication Secrets to Get From Good to Great

As always you can follow Harry, The Twenty Minute VC and Howard on Twitter here!

Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Shabih Rizvi is the Founding Partner @ Gradient Ventures, Google’s new AI-focused venture fund, which will invest in and connect early-stage startups with Google’s resources, innovation, and technical leadership in artificial intelligence. Prior to Gradient, Shabih was a Partner at KPCB, where he was actively involved with investments in TrueCaller, Mobcrush, Veem and Ujet. In addition, he helped the firm build their seed program and served as advisor to Flipagram and Victorious. Before KPCB, Shabih founded and led the startup outreach program for Google Play. Prior to Google Play, Shabih worked on the Mobile Apps Lab team which built SMB products. His primary focus was scaling TalkBin (Acquired by Google) to enterprise clients. Shabih joined Google after Google’s acquisition of AdMob, where he was a manager on the Business Development team.

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In Today’s Episode You Will Learn:

1.) How Shabih made his way into the world of venture with Kleiner Perkins and how he came to be a Founding Partner @ Google’s AI focused venture fund, Gradient? What were Shabih’s greatest lessons from working side by side with John Doerr?

2.) Shabih has said to me before “founder relationships and their longevity really matter”. What does Shabih mean by this? How has this played out for Shabih in an investing environment? What have been Shabih’s subsequent learnings?

3.) How does Shabih identify the “3 buckets” that VCs source from? How does Shabih look to filter through opportunities at scale? What must he see in the deck? What are his quick no’s? What is Shabih’s framework for saying no both with efficiency and kindness? Why does Shabih believe this is one of the hardest parts of the role?

4.) What does the internal investment decision-making process look like at Gradient? Why do they believe that 2 partner meetings a week is optimal? Prior to that, how does Shabih structure his meetings with founders? Why does Shabih believe it is so important to go to them at their HQ? Should all investors go to the founder?

5.) Why is Shabih a strong believer in the decentralisation of talent away from the valley? What are the primary drivers for this decentralization? How does Shabih think about pricing in different regions? To what extent does it differ wildly? How does Shabih respond to traditional SaaS wisdom that you have to build your SaaS business in the valley?

Items Mentioned In Today’s Show:

Shabih’s Fave Book: Measure What Matters, When Breathe Becomes Air 

Shabih’s Most Recent Investment: Scotty.ai

As always you can follow Harry, The Twenty Minute VC and Shabih on Twitter here!

Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

The reality is that hiring amazing developers is hard. Terminal.io is your dedicated partner in rapidly standing up world-class remote technical teams. How do they deliver both speed and quality? Terminal does this by focusing on everything necessary to successfully source, setup, and support these teams – from physical elements like beautiful workspaces and equipment to ongoing resources like HR, payroll, legal, professional learning and development. But don’t take my word for this, take the word of Eventbrite, former 20VC guest Hims, and Dialpad – all customers and lovers of Terminal. You can find out more today at Terminal.io.

Andrew Farah is the Founder & CEO @ Density, the startup that measures real-time occupancy of every room in your office. To date, they have raised over $16m in funding from some great friends of the show in the form of Founders Fund, Mark Suster @ Upfront, Ludlow Ventures, Jason Calacanis, Hiten Shah and Arjun Sethi, just to name a few. As for Andrew, prior to founding Density, he was a Managing Partner @ Rounded, a software development agency & product studio. There, Andrew and the team built the first Density prototype.

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In Today’s Episode You Will Learn:

1.) How Andrew made his way into the world of technology and product with Rounded and came to found the people counter of the next generation in Density?

2.) How does Andrew view the role of super-connectors today? What specific time has a super-connector really moved the needle for Andreq and changed the trajectory of Density? What can one do to first build relationships with these people? What can be done to sustain that relationship and really engage and deepen it?

3.) How does Andrew view the importance of “employee retention” in the ultimate success of a company? Density have never had an employee leave in 4 years, what does Andrew believe they have done right? What has not worked for them? What does he mean when he says, “the best leaders answer employees questions before they are asked”?

4.) What has Andrew found to be the commonalities in the truly special VCs? What do they do that makes them so special? How do they view the world and the assessment of companies that is so right? How does Andrew think about investor selection? Where does Andrew see many founders going wrong with this?

5.) Why does Andrew think that so many hardware startups fail today? What do they consistently underestimate and not understand? What are the core challenges in building a global supply chain? How does one have to think about cost of goods (COG) and unit economics when scaling hardware startups?

Items Mentioned In Today’s Show:

Andrew’s Fave Book: The Idea Factory: Bell Labs and the Great Age of American Innovation

As always you can follow Harry, The Twenty Minute VC and Andrew on Twitter here!

Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Casper, the company that deliver a great night’s sleep at an incredible value. The team of engineers at Casper works nonstop prototyping, collecting data, and engineering what is certainly the most comfortable mattress. The Casper mattress has a unique combination of foams that provide the right pressure relief and alignment, so you feel perfectly balanced and comfortable. Try Casper yourself for 100 nights in your own home – RISK FREE. If you don’t love it, they come pick it up and refund you everything, no questions asked. Go to casper.com to try yours for 100 nights with FREE shipping and returns. Use code 20VC to save $50 on select mattresses today.

Lattice is the #1 people management solution for growing companies and helps companies like Asana, Reddit and Cruise build a strong company culture. With Lattice, it’s easy to launch 360 reviews, share ongoing feedback, facilitate 1:1s, set up goal tracking, and run employee engagement surveys. Lattice is the only solution that combines performance management and employee engagement, so operators can make sure top performers are happy. Lattice is giving away three months of Lattice free to 20VC listeners. Just go to lattice.com/20vc to receive the offer. Build an award-winning culture with Lattice. The #1 people management solution.

Barry Eggers is a Founding Partner @ Lightspeed, one of the world’s leading venture funds with a portfolio that includes the likes of Snapchat, Mulesoft, Affirm, StitchFix, AppDynamics, Nutanix and many more incredible companies. Barry himself has led investments in Snapchat, Metasolv Software (acquired post-IPO by ORCL), Calista Technologies (acquired by MSFT), Arbor Networks (acquired by DHR), Growth Networks (acquired by CSCO). As a result of his incredible success, Barry has been named to Forbes Midas List numerous times. Prior to VC, Barry held executive roles at Cisco Systems where he established many of the company’s largest distribution channels across OEMs, Service Providers, Distributors, and VARs. He also developed Cisco’s initial M&A process and directed the first wave of acquisitions and integrations for the company.

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In Today’s Episode You Will Learn:

1.) How Barry made his way from the world of Cisco to the wonderful world of venture and came to found one of the most successful firms of the decade in Lightspeed?

2.) How does Barry break up the development of the venture ecosystem into 3 distinct stages? What does Barry believe have been the positive changes? What does Barry believe have been the negative changes? Does Barry believe there is an excess supply of capital today? Why does Barry believe there are too many first time funds? What is the outcome?

3.) Did Barry always aim to build the multi-stage, multi-geography firm that he has built with Lightspeed, from the start? What have been the fundamental inflexion points for Lightspeed both in the increase in brand value and liquidity to LPs? Why does Barry believe building a firm really is an art? What should managers most look for in their first LPs?

4.) What does Barry believe are the 3 ways a venture firm can fail in a generational transition? How can firms incentivise young partners to see the career path and trajectory ahead? What must the older partners at the firm be willing to do? What have been Barry’s biggest lessons in their successful generational transition?

5.) Barry has sat on boards for over 21 years, how has Barry seen himself develop and evolve as a board member over time? What makes a truly functional board? What are the best practices? Who is the best board member Barry has ever sat on a board with? What makes Jim Goetz such a special board member?

Items Mentioned In Today’s Show:

Barry’s Fave Book: Quantum Computing: A Gentle Introduction (Scientific and Engineering Computation)

Barry’s Most Recent Investment: Audius

As always you can follow Harry, The Twenty Minute VC and Barry on Twitter here!

Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Philip Krim is the Founder & CEO @ Casper, the global sleep company that launched in 2014 offering perfect mattresses directly to consumers. Since then they have raised over $239m in funding from the likes of NEA, Lerer Hippeau, IVP, Norwest Venture partners and even include Leonardo Di Caprio on their cap table. As for Philip, he is a serial entrepreneur having founded 2 previous startups, launching his first business out of his very own dorm room at the University of Texas. Due to his immense success, he has been profiled in The New York Times, The Wall Street Journal and been awarded a TechCrunch Crunchie award for Best in E-commerce.

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In Today’s Episode You Will Learn:

1.) How Philip made his way into the world of startups and came to launch one of the most successful consumer brands of our day in the form of Casper?

2.) We continuously hear about “the end of retail”. What does retail done poorly mean to Philip? How does he perceive the future of retail and retail done right? How does retail fundamentally change the margin structure of an originally online brand like Casper? What does Philip perceive to be the biggest challenge to opening up retail significantly?

3.) Why does Philip think we have seen many online mattress brands struggle over the past year? How has this affected how he operates and executes the plan with Casper? How does Philip think about diversification within customer acquisition channels? How does Philip assess the saturation rate of different distribution channels?

4.) Casper’s latest lead investor was a strategic investor, Target. How does Philip think about accepting strategic funds? What was the internal debate and decision-making process? What advice would Philip have to founders contemplating accepting strategic money? How can strategics sometimes have ulterior motives?

5.) Does Philip agree with many former CEOs on the show, the most important role of the CEO is management upscaling? What other functions does Philip consider core? How did Philip think about building out the core of his C-Suite? Does he wish he had done it earlier? What element of the C-Suite was the hardest to hire for?

Items Mentioned In Today’s Show:

Philip’s Fave Book: Elon Musk: How the Billionaire CEO of SpaceX and Tesla is Shaping our Future, Bad Blood: Secrets and Lies in a Silicon Valley Startup

As always you can follow Harry, The Twenty Minute VC and Philip on Twitter here!

Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Daniel Gross is the Founder @ Pioneer and the Head of AI @ Y Combinator. Taking them in turn, Pioneer is the home for ambitious outsiders of the world where they are building a community of creative young people working on interesting projects around the globe. YC is obviously the world’s most successful accelerator with alumni that includes the likes of Airbnb, Dropbox, Reddit, Flexport and many more incredible companies. Prior to Pioneer and YC, Daniel was a Director @ Apple where he focused on machine learning, as a result of his prior company, Cue (also a YC company) being acquired by Apple in 2013. Finally, Daniel also has one of the valley’s most impressive angel portfolios with investments in OpenDoor, Cruise (acquired by GM), Gusto and Github, just to name a few.

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In Today’s Episode You Will Learn:

1.) How Daniel made his way from a military camp in Israel to start a company at YC to selling the company to Apple to now, creating a global community of the world’s most ambitious people?

2.) What does Daniel believe is the commonality of truly great people? Why did Daniel decide to start Pioneers now? What are the terms for entering Pioneers? How is Daniel looking to create the global talent engine through gamification with Pioneers? Why is gamification such a strong tool to understand human motivation?

3.) Why did Daniel decide it was the right decision to bring the Pioneers to SF? In the world of decentralized entrepreneurship, why did Daniel feel it necessary to bring everyone to the valley? What does Daniel believe Silicon Valley needs to solve if it is to become the home for crypto and frontier tech? What role does optimism play in the success of SF?

4.) The program is funded through Stripe and Marc Andreesen, many have suggested this poses conflict with potential optionality on projects and talent, how does Daniel think about this conflict? Why is it not a concern? What other challenges does Daniel forsee as being the biggest barriers to the success of Pioneer?

5.) How does Daniel think about KPI’s for the coming 12 months? What are his core KPI’s? How does Daniel construct a framework that will allow him to love previously disliked tasks? How can anyone do this with success?

Items Mentioned In Today’s Show:

Daniel’s Fave Book: Finite and Infinite Games, Enders Game

Daniel’s Most Recent Investment: Jump, Retool

As always you can follow Harry, The Twenty Minute VC and Daniel on Twitter here!

Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Joist has built the go-to platform for contractors. Joist enables contractors to professionally handle everyday tasks like estimating, invoicing, collecting payments, and manage projects, while also helping them grow their businesses as a streamlined CRM. More than 500 thousand contractors have used the Joist platform to manage more than $8.5 billion in invoiced work in North America, the UK, and Australia. Learn more at joist.com. WePay’s got a great case study about how another platform, TeamSnap, is working with WePay to make payments its #1 revenue stream… more than its subscription business. Get it at wepay.com/harry.

Lattice is the #1 people management solution for growing companies and helps companies like Asana, Reddit and Cruise build a strong company culture. With Lattice, it’s easy to launch 360 reviews, share ongoing feedback, facilitate 1:1s, set up goal tracking, and run employee engagement surveys. Lattice is the only solution that combines performance management and employee engagement, so operators can make sure top performers are happy. Lattice is giving away three months of Lattice free to 20VC listeners. Just go to lattice.com/20vc to receive the offer. Build an award-winning culture with Lattice. The #1 people management solution.

Heather Fernandez is the Founder & CEO @ Solv, the startup that simplifies everyday healthcare by providing access to high quality, last-minute care. To date, Heather has raised over $23m in funding from some of the great of the world of venture including Bill Gurley @ Benchmark, Theresia @ Aspect, James Slavet @ Greylock and Pete Flint @ NFX. Prior to Solv, Heather was part of the early team @ Trulia, where she led advertising product, marketing, and sales strategy and saw the team go from 20 people through to the $2.5B acquisition by Zillow Group. Before Trulia, Heather was at Morgan Stanley and more interestingly was National Deputy Press Secretary for Senator John McCain’s 2000 presidential campaign. If all of that was not enough, Heather is also a Board Member at the global behemoth, Atlassian.

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In Today’s Episode You Will Learn:

1.) How Heather made her way into the world of startups from the world of politics? How she came to be one of the early team at Trulia? What was the a-ha moment for Solv?

2.) How does Heather fundamentally define “culture”? What is the trust equation? Why does it play such a central role in successful culture building? What does Theather mean when she discusses “constructive candor”? What are the common mistakes Heather sees founders make when it comes to scaling culture? What literal actions can be done to instil trust and respect within the team?

3.) Does Heather agree with James @ ThredUp, “marketplaces founders have to be immensely stubborn”? Would Heather agree with Leah @ TaskRabbit with regards to marketplace NPS and “one side of the equation will always be less content”?

4.) What advice would Heather give to managers to maximize their impact in their organisation and their career? How does Heather think about bringing in the right people at various stages of the company? How does it change with scale? On funding, Solv has raised $23m, how does Heather think about when is the right time to pour fuel on the fire?

5.) Heather is also on the board of Atlassian, so what are the core benefits of simultaneously sitting on a board and managing your own board? What have been Heather’s biggest learnings from her time on the Atlassian board? How do the best founders manage their boards successfully?

Items Mentioned In Today’s Show:

Heather’s Fave Book: The American Political Tradition and the Men Who Made it

As always you can follow Harry, The Twenty Minute VC and Heather on Twitter here!

Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Are you told your standards are too high, well The League is the app that tells you to keep them that way, they know your time is valuable so simply tell them your preferences and they will handle the scouting and vetting for you. Plus even better, your profile will only ever be seen by people who match your preferences, matches expire after 21 days and so there are no drawn-out games and they even require LinkedIn to protect your privacy and block you from matching with co-workers and business connections. You can apply now by downloading The League on the app store or heading to The League.com

Zoom is the fastest-growing video and web conferencing service, providing one consistent enterprise experience that allows you to engage in an a variety of activities including video meetings and webinars, collaboration-enabled conference rooms, and persistent chat all in one platform. Plus, it is the easiest solution to manage, scale, and use, and has the most straightforward, affordable pricing. And you can see for yourself! Sign up for a free account (not a trial!). Just visit Zoom.us.

Culture Amp is the platform that makes it easy to collect, understand and act on employee feedback. From onboarding surveys to company-wide engagement, individual effectiveness and more, the platform manages multiple sources of feedback and connects the dots for you and that is why companies like Slack, Nike, Oracle and Lyft all trust Culture Amp. It enables leaders to make better decisions, demonstrate impact and turn your company culture into a competitive edge.  Find out more on cultureamp.com.

Avichal Garg is the Managing Partner @ Electric Capital, one of the leading crypto asset management firms today investing in both liquid and illiquid tokens that are emerging stores of value and rooted in novel technology. Prior to Electric they personally invested in Anchor, Bitwise, Basecoin and more. As for Avichal as well as Electric, he is a part-time partner at YC and prior to YC, he was Director of Product Management at Facebook where he led the Local product team (a $3.5Bn line of business at the time). Before FB, Avichal worked on Search and Ads at Google, started and sold a few companies, and invested in startups including Optimizely, Boom, Color, Cruise, Instawork, CaseText, and many more.

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In Today’s Episode You Will Learn:

1.) How Avichal made his way into the world of startups, began angel investing, discovering the power of crypto and why now for Electric Capital?

2.) How does Avichal break the world of crypto into 4 fundamentally distinct buckets today? Which 2 elements does Avichal believe will be the biggest value accruers? What is the core question to ask when assessing a crypto opportunity today? How does angel investing compare to crypto investing?

3.) Where are the majority of ICO dollars going today? Why does Avichal believe that ICOs in large part do not fundamentally make sense from an investment and pricing perspective? How does Avichal think about liquidity in the world of crypto? As an institutional manager, what mindset does Avichal embrace when liquidity is possible?

4.) Why does Avichal believe that regulation and government controls is the opposite of the real risk to the space? If this is not the biggest risk, what does Avichal believe is the biggest risk to the potential of the space? Why does Avichal believe that the US government have handled the space with nuance and intellect?

5.) Why does Avichal believe that decentralized teams will not work? How does this correlate to the progression of platform complexity with time? Why does Avichal believe this will lead to the re-centralization of talent back to Silicon Valley? What catalysts will act to speed this up or hamper it’s re-centralisation?

Items Mentioned In Today’s Show:

Avichal’s Fave Book: Ender’s Game

Avichal’s Most Recent Investment: Coda Cryptocurrency Protocol

As always you can follow Harry, Avichal and The Twenty Minute VC on Twitter here!

Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Are you told your standards are too high, well The League is the app that tells you to keep them that way, they know your time is valuable so simply tell them your preferences and they will handle the scouting and vetting for you. Plus even better, your profile will only ever be seen by people who match your preferences, matches expire after 21 days and so there are no drawn-out games and they even require LinkedIn to protect your privacy and block you from matching with co-workers and business connections. You can apply now by downloading The League on the app store or heading to The League.com

Zoom is the fastest-growing video and web conferencing service, providing one consistent enterprise experience that allows you to engage in an a variety of activities including video meetings and webinars, collaboration-enabled conference rooms, and persistent chat all in one platform. Plus, it is the easiest solution to manage, scale, and use, and has the most straightforward, affordable pricing. And you can see for yourself! Sign up for a free account (not a trial!). Just visit Zoom.us.

Culture Amp is the platform that makes it easy to collect, understand and act on employee feedback. From onboarding surveys to company-wide engagement, individual effectiveness and more, the platform manages multiple sources of feedback and connects the dots for you and that is why companies like Slack, Nike, Oracle and Lyft all trust Culture Amp. It enables leaders to make better decisions, demonstrate impact and turn your company culture into a competitive edge.  Find out more on cultureamp.com.

 

Dylan Serota is the Founder & Chief Strategy Officer @ Terminal, the startup that helps you create world-class technical teams through remote operations as a service. They recently raised a phenomenal $13m Series A with some of the world’s most renowned names including Lightspeed, KPCB, Craft, Thiel, Atomic and Jerry Yang just to name a few. As for Dylan, he is also a Founder-in-Residence @ Atomic, one of the valley’s most exciting new institutions which both founds and funds companies and includes the likes of Hims, TalkIQ (acq by Dialpad) and more. Prior to Atomic and Terminal, Dylan was Head of Platform @ Eventbrite where he led platform product org, built third-party developer ecosystem and platform partnerships.

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In Today’s Episode You Will Learn:

1.) How Dylan made his way into the world of startups with Eventbrite and how that led to his realisation on the future of development operations with Terminal?

2.) Why does Dylan believe that it is important for startups to build distributed teams earlier in their growth curve than often suggested? What are the key aspects to making remote teams work well? Why does Dylan believe that “companies overvalue their culture”? How does Dylan assess culture across remote teams?

3.) Jason lemkin says “startups can either hire a stretch VP or a burnt out mediocre VP”, does Dylan agree with this? How does Dylan assess the balance between hiring functional specialists vs jack of all trades? When is the right time to make the transition from generalist to specialist?

4.) Hw does Dylan analyze and assess a startup leaderships team ability to adapt and prioritize speed? What is key to successful decision-making today in startups? How does Dylan think about the importance of speed when it comes to product ideation and iteration?

5.) What does Dylan believe is the biggest mistake many people make early in their career? What are the commonalities of the truly successful people in how they have structured their careers? How does Dylan think about the balance between title vs salary vs experience? What should one optimise for and when?

Items Mentioned In Today’s Show:

Dylan’s Fave Book: The Selfish Gene by Richard Dawkins

As always you can follow Harry, The Twenty Minute VC and Dylan on Twitter here!

Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Are you told your standards are too high, well The League is the app that tells you to keep them that way, they know your time is valuable so simply tell them your preferences and they will handle the scouting and vetting for you. Plus even better, your profile will only ever be seen by people who match your preferences, matches expire after 21 days and so there are no drawn-out games and they even require LinkedIn to protect your privacy and block you from matching with co-workers and business connections. You can apply now by downloading The League on the app store or heading to The League.com

Zoom is the fastest-growing video and web conferencing service, providing one consistent enterprise experience that allows you to engage in an a variety of activities including video meetings and webinars, collaboration-enabled conference rooms, and persistent chat all in one platform. Plus, it is the easiest solution to manage, scale, and use, and has the most straightforward, affordable pricing. And you can see for yourself! Sign up for a free account (not a trial!). Just visit Zoom.us.

Culture Amp is the platform that makes it easy to collect, understand and act on employee feedback. From onboarding surveys to company-wide engagement, individual effectiveness and more, the platform manages multiple sources of feedback and connects the dots for you and that is why companies like Slack, Nike, Oracle and Lyft all trust Culture Amp. It enables leaders to make better decisions, demonstrate impact and turn your company culture into a competitive edge.  Find out more on cultureamp.com.

Jeff Fagnan is Founding Partner @ Accomplice, one of the East Coast’s leading early-stage funds with a portfolio including the likes of AngelList, PillPack (acq by Amazon), Freshbooks, Hopper, Secret Escapes and many more incredible companies. Accomplice is also unique as it is a platform builder creating incredible initiatives such as Spearhead, Maiden Lane and Boston Syndicates, really moving the needle in seeding local ecosystems. As for Jeff he is well known as a founding investor, working with most of his portfolio since inception, sometimes as a co-founder including Veracode (Sold to CA Technologies‍). Jeff also sits on the board of AngelList, PillPack, InsightSquared, Hopper, Freshbooks and more.

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In Today’s Episode You Will Learn:

1.) How Jeff made his way into the world of VC from consulting over 18 years ago? How did his experience of the bubble influence Jeff’s mindset and thinking?

2.) What did Jeff learn about building an optimal venture partnership with the transition from the 23 partner Atlas to the tight-knit Accomplice? Where does Jeff believe most venture partnerships go wrong today? What does Jeff believe is the right size partnership in venture? Why does Jeff believe that partners are there to save each other from themselves?

3.) How did Jeff’s experience with Atlas effect his views on portfolio construction? Why does Jeff advocate for the model of raising $200m every 2.5 years for a pure seed strategy? How does Jeff think about building an effective reserve strategy? Why does Jeff not believe pro-rata should be guaranteed? Why does Jeff believe force ranking a portfolio is dangerous?

4.) Jeff believes the best VCs are able to manage 2 things, what are those 2 things? From his 18 years on boards, what does Jeff believe makes the truly special board member? Who is the best he has worked with and why? How does Jeff look to gain the balance of being both proactive to opportunities and reactive to inbound?

5.) Accomplice has recently made it’s foray into the West Coast, what was the thinking behind that move? How does Accomplice think about establishing mindshare as a new entrant in a hotly contested environment? What does Jeff believe is the key to successful geographic expansion in venture?

Items Mentioned In Today’s Show:

Jeff’s Fave Book: Where The Wild Things Are 

Jeff’s Most Recent Investment: Perch

As always you can follow Harry and The Twenty Minute VC on Twitter here!

Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Are you told your standards are too high, well The League is the app that tells you to keep them that way, they know your time is valuable so simply tell them your preferences and they will handle the scouting and vetting for you. Plus even better, your profile will only ever be seen by people who match your preferences, matches expire after 21 days and so there are no drawn-out games and they even require LinkedIn to protect your privacy and block you from matching with co-workers and business connections. You can apply now by downloading The League on the app store or heading to The League.com

Zoom is the fastest-growing video and web conferencing service, providing one consistent enterprise experience that allows you to engage in an a variety of activities including video meetings and webinars, collaboration-enabled conference rooms, and persistent chat all in one platform. Plus, it is the easiest solution to manage, scale, and use, and has the most straightforward, affordable pricing. And you can see for yourself! Sign up for a free account (not a trial!). Just visit Zoom.us.

Culture Amp is the platform that makes it easy to collect, understand and act on employee feedback. From onboarding surveys to company-wide engagement, individual effectiveness and more, the platform manages multiple sources of feedback and connects the dots for you and that is why companies like Slack, Nike, Oracle and Lyft all trust Culture Amp. It enables leaders to make better decisions, demonstrate impact and turn your company culture into a competitive edge.  Find out more on cultureamp.com.

Armon Dadgar is the Founder & CTO @ Hashicorp, the open-source software company that provides consistent workflows to provision, secure, connect and run any infrastructure for any application. To date, Hashicorp has raised over $74m in VC funding from many friends of the show including Scott Raney @ Redpoint, Glenn Solomon @ GGV, Semil Shah, True Ventures and Mayfield. As for Armon, today he leads the Hashicorp research group and focused on industrial research in the security and large-scale system management space. Prior to founding Hashicorp, Armon was a software engineer @ Kiip and Amazon.

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In Today’s Episode You Will Learn:

1.) How Armon made his way from intern at Amazon to founding Hashicorp and creating the game-changing suite of tools in the world of DevOps?

2.) Hashicorp has enjoyed success after success with new products, so what does Armon believe is the secret to continuous product innovation? What does Armon mean when he says “there are really 3 phases to product adoption”? How does Armon determine between vision for a product and the realism when it is not working, when launching products?

3.) Hashicorp only recently started generating revenue, why was now the right time? At what point does one go from building products for the community to building products people will pay for? How does Armon assess professional services today? What does Armon believe are the 2 foundational problems with “professional services”?

4.) Many VCs suggest it’s impossible to build big infrastructure businesses today given the commoditizing forces to open source and cloud computing. How have Hashicorp navigated that and bucked that conventional wisdom? How has Armon also bucked the conventional wisdom on the importance of focus? What core tenets must remain if one wants to go against this emphasis on focus?

5.) Armon and his co-founder brought on a CEO early, what was the realisation moment for the need to bring in an external CEO? How did Armon look to get comfortable with this transition? What advice would Armon give to founders contemplating bringing in an external CEO? With the benefit of hindsight, what would Armon do differently if he had the time again?

Items Mentioned In Today’s Show:

Armon’s Fave Book: To The Lighthouse by Virginia Woolf

As always you can follow Harry, The Twenty Minute VC and Armon on Twitter here!

Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Are you told your standards are too high, well The League is the app that tells you to keep them that way, they know your time is valuable so simply tell them your preferences and they will handle the scouting and vetting for you. Plus even better, your profile will only ever be seen by people who match your preferences, matches expire after 21 days and so there are no drawn-out games and they even require LinkedIn to protect your privacy and block you from matching with co-workers and business connections. You can apply now by downloading The League on the app store or heading to The League.com

Zoom is the fastest-growing video and web conferencing service, providing one consistent enterprise experience that allows you to engage in an a variety of activities including video meetings and webinars, collaboration-enabled conference rooms, and persistent chat all in one platform. Plus, it is the easiest solution to manage, scale, and use, and has the most straightforward, affordable pricing. And you can see for yourself! Sign up for a free account (not a trial!). Just visit Zoom.us.

Culture Amp is the platform that makes it easy to collect, understand and act on employee feedback. From onboarding surveys to company-wide engagement, individual effectiveness and more, the platform manages multiple sources of feedback and connects the dots for you and that is why companies like Slack, Nike, Oracle and Lyft all trust Culture Amp. It enables leaders to make better decisions, demonstrate impact and turn your company culture into a competitive edge.  Find out more on cultureamp.com.

Nick Brown is Managing Partner @ Imaginary, founded alongside Net-A-Porter founder, Natalie Massenet, Imaginary invests in early–stage opportunities at the intersection of retail and technology. Included in their incredible portfolio is the likes of Glossier, Daily Harvest, Farfetch, Everlane and many more awesome companies. Prior to co-founding Imaginary, Nick was a Partner at 14W Venture Partners where he invested in the likes of Goop, Outdoor Voices, The Real Real and Business of Fashion just to name a few. Before that Nick was Head of New Media @ NV Investments.

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In Today’s Episode You Will Learn:

1.) How Nick made his way into the world of venture and consumer investing from the days of investment banking?

2.) We have seen an explosion in the world of consumer with regards to D2C brands, does Nick believe we are in a D2C bubble? There is a lot of skepticism around physical product companies being venture businesses, so what are the core considerations for Nick when investing in physical product brands today?

3.) Having backed the likes of Glossier, Farfetch, Everlane etc, what does Nick believe are some of the leading indicators from the early days whether a company has a sustaining and authentic brand? What does Nick believe is the future for direct to consumer of the next 24-36 months? What is he most excited by?

4.) How does Nick think about the interaction between D2C brands and wholesale and physical retail? When is the right time to pull the wholesale lever? What does Nick believe is a healthy ratio between paid to organic customer acquisition? What are the commonalities in the consumer brands that have broken out within his portfolio?

5.) In terms of character traits, what commonalities does Nick see in the most successful consumer founders he has backed today? We have seen a rise in the celebrity founder over the last few years, so what is the role of the celebrity founder? When does it work? When does it not work? How does the future of celebrity founder look to Nick?

Items Mentioned In Today’s Show:

Nick’s Fave Book: To Kill A Mockingbird

Nick’s Most Recent Investment: Fitplan

As always you can follow Harry and The Twenty Minute VC on Twitter here!

Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Are you told your standards are too high, well The League is the app that tells you to keep them that way, they know your time is valuable so simply tell them your preferences and they will handle the scouting and vetting for you. Plus even better, your profile will only ever be seen by people who match your preferences, matches expire after 21 days and so there are no drawn-out games and they even require LinkedIn to protect your privacy and block you from matching with co-workers and business connections. You can apply now by downloading The League on the app store or heading to The League.com

Zoom is the fastest-growing video and web conferencing service, providing one consistent enterprise experience that allows you to engage in an a variety of activities including video meetings and webinars, collaboration-enabled conference rooms, and persistent chat all in one platform. Plus, it is the easiest solution to manage, scale, and use, and has the most straightforward, affordable pricing. And you can see for yourself! Sign up for a free account (not a trial!). Just visit Zoom.us.

Culture Amp is the platform that makes it easy to collect, understand and act on employee feedback. From onboarding surveys to company-wide engagement, individual effectiveness and more, the platform manages multiple sources of feedback and connects the dots for you and that is why companies like Slack, Nike, Oracle and Lyft all trust Culture Amp. It enables leaders to make better decisions, demonstrate impact and turn your company culture into a competitive edge.  Find out more on cultureamp.com.

Adam Goldberg is a Partner @ Lightspeed Venture Partners, one of the world’s leading funds with a portfolio including the likes of SNAP, Mulesoft, Max Levchin’s Affirm, AppDynamics and many more incredible companies. As for Adam, at age 13, Adam enrolled as a full-time student at UC Berkeley, where he studied pure and applied mathematics and conducted research in number theory and machine learning. He went on to work as a mathematician for the Department of Defense and as a researcher Berkeley, Wisconsin-Madison and Stanford. Following that, Adam worked as an engineer at Palantir and Dropbox and was an early product manager at Rubrik. In 2016, Adam left Rubrik to become a partner at Lightspeed where he has invested in the likes of Basis, Vector and Totemic Labs, just to name a few.

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In Today’s Episode You Will Learn:

1.) How Adam made his way into the world of venture from the department of defence and working at titans such as Palantir and Dropbox?

2.) Why does Adam believe the rate of founder learning is the most important skill that an investor can evaluate and assess? What does optimizing for learning really mean to Adam? In practice, what can one do to optimize for learning? What are the common traits and signs of those founders that do this well?

3.) Why does Adam believe that there remains today no mass market decentralised consumer product? What is needed for this to happen? How does Adam forsee the development of token economics over the coming years? What novel token financing solutions does Adam respect? What is required within token economics for Adam to gain real comfort?

4.) Why does Adam believe that the Telegram ICO got such attention? Why is Adam fundamentally bullish on the opportunity? What 2 core characteristics does Telegram have that are required for crypto projects to be successful? On the other side of the table, where is there cause for concern when reviewing the opportunity?

5.)How does Adam think about “betting on fundamental trade-offs in crypto”? What are the 4 key trade-offs that founders must contemplate? What are the trade-offs that Adam is willing to accept vs not accept? How does Adam envisage the willingness to accept trade-offs so widely, change over time in the space?

Items Mentioned In Today’s Show:

Adam’s Fave Book: Flowers for Algernon

Adam’s Most Recent Investment: Strangeworks

As always you can follow Harry, The Twenty Minute VC and Adam on Twitter here!

Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Are you told your standards are too high, well The League is the app that tells you to keep them that way, they know your time is valuable so simply tell them your preferences and they will handle the scouting and vetting for you. Plus even better, your profile will only ever be seen by people who match your preferences, matches expire after 21 days and so there are no drawn-out games and they even require LinkedIn to protect your privacy and block you from matching with co-workers and business connections. You can apply now by downloading The League on the app store or heading to The League.com

Zoom is the fastest-growing video and web conferencing service, providing one consistent enterprise experience that allows you to engage in an a variety of activities including video meetings and webinars, collaboration-enabled conference rooms, and persistent chat all in one platform. Plus, it is the easiest solution to manage, scale, and use, and has the most straightforward, affordable pricing. And you can see for yourself! Sign up for a free account (not a trial!). Just visit Zoom.us.

Culture Amp is the platform that makes it easy to collect, understand and act on employee feedback. From onboarding surveys to company-wide engagement, individual effectiveness and more, the platform manages multiple sources of feedback and connects the dots for you and that is why companies like Slack, Nike, Oracle and Lyft all trust Culture Amp. It enables leaders to make better decisions, demonstrate impact and turn your company culture into a competitive edge.  Find out more on cultureamp.com.

Eddy Lu is the Co-Founder & CEO @ GOAT, the largest marketplace in the world for buying and selling authentic sneakers. To date, GOAT have raised over $97m in VC funding from some of the best in the business including Accel, Index, Upfront and include angel investments from Elad Gil, Ashton Kutcher and Alexis Ohanian. Prior to GOAT, Eddy enjoyed numerous different roles including founding a chain of Japanese dessert stores building a slew of different 99c apps and started on Wall St with Lehmann Brothers and Deloitte.

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In Today’s Episode You Will Learn:

1.) How Eddy made his way from Wall St to making 99c apps to creating a chain of Japanese desert stores to founding the world’s largest sneaker marketplace in GOAT?

2.) Pivoting from social dining to sneaker marketplace, how does Eddy determine between mission and passion for the vision vs when something is simply not working? What core metrics made Eddy realise this pivot was needed? How did Eddy communicate the pivot to the existing investor base? How did he get them on board for the next chapter?

3.) Over the years, GOAT has had many investors wanting to invest, how does Eddy approach investor selection? What advice does Eddy have on optimising for valuation and the terms that founders should really focus on? What have been the biggest lessons from having former Twitter COO, Adam Bain on the GOAT board?

4.) Does Eddy agree with Paul at Canvas that marketplace founders should give up if they do not have differentiated supply? What does Eddy believe is the core characteristic of the most successful marketplaces? To what extent does Eddy believe that early marketplaces must rely on existing distribution and offline activities to scale?

5.) Eddy took the decision to merge with Flight Club, what was behind the decision to open up the business to physical retail? Why does Eddy believe that physical retail does not affect the margin structure massively when compared to it’s online counterpart? How does Eddy assess the categories that make sense for physical retail between those that do not?

Items Mentioned In Today’s Show:

Eddy’s Fave Book: Crime and Punishment 

As always you can follow Harry, The Twenty Minute VC and Eddy on Twitter here!

Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Are you told your standards are too high, well The League is the app that tells you to keep them that way, they know your time is valuable so simply tell them your preferences and they will handle the scouting and vetting for you. Plus even better, your profile will only ever be seen by people who match your preferences, matches expire after 21 days and so there are no drawn-out games and they even require LinkedIn to protect your privacy and block you from matching with co-workers and business connections. You can apply now by downloading The League on the app store or heading to The League.com

Zoom is the fastest-growing video and web conferencing service, providing one consistent enterprise experience that allows you to engage in an a variety of activities including video meetings and webinars, collaboration-enabled conference rooms, and persistent chat all in one platform. Plus, it is the easiest solution to manage, scale, and use, and has the most straightforward, affordable pricing. And you can see for yourself! Sign up for a free account (not a trial!). Just visit Zoom.us.

Culture Amp is the platform that makes it easy to collect, understand and act on employee feedback. From onboarding surveys to company-wide engagement, individual effectiveness and more, the platform manages multiple sources of feedback and connects the dots for you and that is why companies like Slack, Nike, Oracle and Lyft all trust Culture Amp. It enables leaders to make better decisions, demonstrate impact and turn your company culture into a competitive edge.  Find out more on cultureamp.com.

Jason Stoffer is Managing Partner @ Maveron, the consumer-only venture fund backing a new breed of brands. Their stellar portfolio includes the likes of eBay, Zulily, General Assembly, Allbirds and Dia&Co, just to name a few. As for Jason, Jason is the master of all things consumer education, e-commerce and marketplace businesses. He has been a Board Member of a number of category-leading consumer businesses, such as zulily (Nasdaq: ZU), General Assembly (acquired by Adecco), Common and more. Prior to Maveron, Jason was Senior Director of Strategic Operations at Career Education Corp where he saw the business scale to a market cap of over $4.5Bn.

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In Today’s Episode You Will Learn:

1.) How Jason made his way into the world of VC from the world of journalism? What were his biggest takeaways from seeing the boom and bust cycle of 2001 and 2008?

2.) Why does Jason believe that moats matter as much, if not more than brand today? How can founders look to create the strongest form of defensibility? How does Jason analyze the 2 paths for consumer businesses today; raise large amounts of capital and buy growth or raise little, grow slowly, understand unit economics and channels over time? Does Jason think we will see a graveyard of immensely funded consumer businesses?

3.) How does Jason view paid acquisition today? Does Jason agree with Peter Fenton. “there is a lack of free and open distribution in consumer today”? When does Jason believe that consumer founders should really focus on CAC/LTV? What metrics really matter in the early days for consumer? How does Jason analyse acquisition channel mortality? When does he mean when he says, “CAC works, until it does not”?

4.) Jason has said before that “VC is a struggle”. What elements does Jason find most challenging? How does Jason deal witht he shit hit the fan moments as a VC? Can VCs in this hyper-competitive world be openly vulnerable in Jason’s eyes? How has Jason seen his approach to hard and challenging situations in VC develop over time?

5.) Does Jason believe we are in a consolidatory environment today or will we see the next generation of mega consumer brands being built? When investing, does Jason ask, who is the potential acquirer? Why? What multiple is achievable? Would Jason agree with Kirsten Green that “Amazon does more to make the market than destroy it”? How does Amazon affect Jason’s investment philosophy and approach?

Items Mentioned In Today’s Show:

Jason’s Fave Book: 100 Years of Solitude

Jason’s Most Recent Investment: Imperfect Produce

As always you can follow Harry, The Twenty Minute VC and Jason on Twitter here!

Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Are you told your standards are too high, well The League is the app that tells you to keep them that way, they know your time is valuable so simply tell them your preferences and they will handle the scouting and vetting for you. Plus even better, your profile will only ever be seen by people who match your preferences, matches expire after 21 days and so there are no drawn-out games and they even require LinkedIn to protect your privacy and block you from matching with co-workers and business connections. You can apply now by downloading The League on the app store or heading to The League.com

Zoom is the fastest-growing video and web conferencing service, providing one consistent enterprise experience that allows you to engage in an a variety of activities including video meetings and webinars, collaboration-enabled conference rooms, and persistent chat all in one platform. Plus, it is the easiest solution to manage, scale, and use, and has the most straightforward, affordable pricing. And you can see for yourself! Sign up for a free account (not a trial!). Just visit Zoom.us.

Culture Amp is the platform that makes it easy to collect, understand and act on employee feedback. From onboarding surveys to company-wide engagement, individual effectiveness and more, the platform manages multiple sources of feedback and connects the dots for you and that is why companies like Slack, Nike, Oracle and Lyft all trust Culture Amp. It enables leaders to make better decisions, demonstrate impact and turn your company culture into a competitive edge.  Find out more on cultureamp.com.

Fritz Lanman is the CEO @ ClassPass, the startup that provides the most flexible fitness membership ever. To date, they have raised over $154m in VC funding from the likes of Thrive, GV, CRV, Fifth Wall and Temasek just to name a few. As for Fritz, prior to ClassPass he was the Founder & CEO @ Livestar, a mobile recommendations startup that was acquired by Pinterest. Before that, he was a Senior Director in the Corporate Strategy Group @ Microsoft where he led several multi-billion dollar M&A evaluations and strategy projects including the Facebook investment and Yahoo deal. If that was not enough, Fritz is also a tremendously successful angel with a portfolio including the likes of Square, Pinterest, Wish, Flexport, Everlane and 75 or so more companies.

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In Today’s Episode You Will Learn:

1.) How Fritz made his way into the world of startups with Microsoft? How that led to angel investments in Wish, Flexport, Square and more? How he came to be CEO @ ClassPass?

2.) How did the $250m Microsoft investment in Facebook come about? What made Fritz so confident he told Steve Ballmer he was willing to bet his career it would be a $10Bn company? What was the decision-making process internally around that deal?

3.) How does Fritz assess his own asset allocation strategy? Why does Fritz not agree with thesis-driven angel investing? When starting angel investing, how did he approach portfolio construction? Why does Fritz believe it is immensely synergistic to be both an operator and angel? As a result, how does Fritz approach placing investors in a quadrant between helpfulness and high maintenance?

4.) Why does Fritz believe that your investor cannot be your recruiter? What have been Fritz biggest learnings on continuously attracting the best talent? Why does Fritz believe that it is BS that one should not celebrate fundraising? Ultimately, what does Fritz elieve fundraising signifies?

5.) ClassPass has expanded to 34 markets over the last few years, how does Fritz determine when is the right time to pour fuel on the fire? What are the 2 fundamental questions one must ask before you do? Does Fritz believe that aggressive growth and capital efficiency are mutually exclusive? How does Fritz think about capital efficiency with ClassPass today?

Items Mentioned In Today’s Show:

Fritz’s Fave Book: Endurance: Shackleton’s Incredible Voyage to the Antarctic

As always you can follow Harry, The Twenty Minute VC and Fritz on Twitter here!

Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

The reality is that hiring amazing developers is hard. Terminal.io is your dedicated partner in rapidly standing up world-class remote technical teams. How do they deliver both speed and quality? Terminal does this by focusing on everything necessary to successfully source, setup, and support these teams – from physical elements like beautiful workspaces and equipment to ongoing resources like HR, payroll, legal, professional learning and development. But don’t take my word for this, take the word of Eventbrite, former 20VC guest Hims, and Dialpad – all customers and lovers of Terminal. You can find out more today at Terminal.io.

Whether you’re starting your own small business or getting serious about making your small business more efficient, you need to invite FreshBooks to the table. FreshBooks makes cloud accounting software that’s so ridiculously easy to use and you’ll quickly understand why over 10 million people use it to radically streamline how they deal with their admin and paperwork. Plus, FreshBooks can handle a lot more than accounting related tasks. Using FreshBooks is kind of like having your own admin assistant who’s got your back, 24/7. To claim your 30-day unrestricted free trial, click here enter Twenty Minute VC in the “how did you hear about us section”.

Highfive makes meetings better for thousands of organizations with insanely simple video conferencing designed for meeting rooms. It’s the easiest-to-use solution, with all-in-one hardware and intuitive cloud software. Plus, it’s a high-quality experience with industry-leading audio powered by Dolby Voice. It’s so easy to use, that there’s no pin codes or app downloads. Just click a link in your browser, and you’re in the meeting. With customers in over 100 countries, Highfive is already trusted by the likes of Evernote, Expensify, and Betterment and you can learn more by simply heading over to highfive.com.

Elad Gil is the Founder @ Color, the startup that shows you your genes can help you make better health decisions. They have raised over $112m in funding from the likes of General Catalyst, CRV, 8VC, Aaron Levie and more incredible names. Elad is also an incredible angel, counting the likes of Airbnb, Stripe, Optimizely, Opendoor and Wish all in his portfolio. Now Elad is adding a new string to his very talented bow with the release of his book, High Growth Handbook, published by Stripe in which Elad interviews 14 leaders from the valley from Marc Andreesen to Reid Hoffman to Patrick Collison. Plus shares his own experiences from Google, growing from 1,500 to 15,000 and Twitter, growing from 100 to 1,500. High Growth Handbook is now available for sale on Amazon, Kindle, Kobo.

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In Today’s Episode You Will Learn:

1.) How Elad made his way into the world of startups, came to found 2 companies that sold to Twitter and Google and came to invest in Airbnb, Stripe, Wish etc?

2.) How does Elad define the role of the CEO today? What are the commonalities in those truly great CEOs? How do the very best CEOs hire the very best execs? How do they address role allocation internally? How do they determine between employees that do and do not scale with the firm? Where do CEOs make the most fatal mistakes in high growth startups?

3.) Why are pre-emptive rounds so common today? Why does Elad believe many people will lose a lot of money in them? What advice does Elad give to founders when they are an option? Does Elad believe the lack of liquidity is good for venture this cycle? How does Elad assess the emergence of megafunds? How does this alter and distort the market?

4.) With regards to market share, how should founders prioritise between pricing and market share? Is cash ever a defensible moat? What does Elad mean when he says that “too many people are stuck on Amazon as the winning model”? Why does Elad believe that margins and capital leverage are the unsung heroes of tech?

5.) Why does Elad believe we have seen such a reduction in M&A? Why do many founders not fully assess the financial benefits of being bought by a high growth startup?  What are the big questions founders should ask when an M&A opportunity does arise? What does Elad believe are the reasons to avoid IPOing? What are the inherent benefits of going public?

Items Mentioned In Today’s Show:

Elad’s Fave Book: Ben Horowitz, Andy Grove

As always you can follow Harry, The Twenty Minute VC and Elad on Twitter here!

Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

The reality is that hiring amazing developers is hard. Terminal.io is your dedicated partner in rapidly standing up world-class remote technical teams. How do they deliver both speed and quality? Terminal does this by focusing on everything necessary to successfully source, setup, and support these teams – from physical elements like beautiful workspaces and equipment to ongoing resources like HR, payroll, legal, professional learning and development. But don’t take my word for this, take the word of Eventbrite, former 20VC guest Hims, and Dialpad – all customers and lovers of Terminal. You can find out more today at Terminal.io.

Whether you’re starting your own small business or getting serious about making your small business more efficient, you need to invite FreshBooks to the table. FreshBooks makes cloud accounting software that’s so ridiculously easy to use and you’ll quickly understand why over 10 million people use it to radically streamline how they deal with their admin and paperwork. Plus, FreshBooks can handle a lot more than accounting related tasks. Using FreshBooks is kind of like having your own admin assistant who’s got your back, 24/7. To claim your 30-day unrestricted free trial, click here enter Twenty Minute VC in the “how did you hear about us section”.

Highfive makes meetings better for thousands of organizations with insanely simple video conferencing designed for meeting rooms. It’s the easiest-to-use solution, with all-in-one hardware and intuitive cloud software. Plus, it’s a high-quality experience with industry-leading audio powered by Dolby Voice. It’s so easy to use, that there’s no pin codes or app downloads. Just click a link in your browser, and you’re in the meeting. With customers in over 100 countries, Highfive is already trusted by the likes of Evernote, Expensify, and Betterment and you can learn more by simply heading over to highfive.com.

Rachel Blumenthal is the Founder & CEO @ Rockets of Awesome, the startup that is reinventing the way parents shop for their kids clothes. To date, Rachel has raised over $19m in VC funding from the likes of Kirsten Green @ Forerunner, August Capital, General Catalyst, Gwyneth Paltrow and Female Founders Fund to name a few. Prior to Rockets of Awesome, Rachel founded fashion jewelry brand, Rachel Leigh. Rachel scaled the business to being available in over 300 stores worldwide and being named one of Oprah’s “Favourite Things”. Before that Rachel began her career in the publicity department at Yves Saint Lauren.

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In Today’s Episode You Will Learn:

1.) How Rachel went from founding a company that created one of Oprah’s “favourite things” to reinventing the way parents shop for their children today?

2.) Why does Rachel believe that “fundraising is like dating”? What does Rachel mean when she says “you have to play the game”? What does this literally look like in practice? What works in generating investor interest? What does not? Where does Rachel see many make mistakes in the fundraising process?

3.) How does Rachel think about capital efficiency with the evolution of her business? What tips and suggestions does Rachel give to increasing burn flexibility when future growth is ambiguous? Why does Rachel disagree with the thesis of raise money when you don’t need it? What length of time does Rachel believe is the right time to raise for?

4.) Rachel has said before that, “the best investors are operators”. What makes Rachel believe this? What are the drawbacks to operator VCs? What are the benefits to non-operator investors? What makes the truly special investor? How can a founder stress test this prior to their investment? What advice would Rachel give to a non-operator VC to improve their empathy and experience with founders?

5.) Rachel previous sly said to me that “being a woman in this male-dominated environment is everything the stereotype suggests”, what moment or story particularly resonates for Rachel when saying this? How did she respond? How can less confident first time minority founders respond in these situations?

Items Mentioned In Today’s Show:

Rachel’s Fave Book: Fast Company, Inc

As always you can follow Harry, The Twenty Minute VC and Rachel on Twitter here!

Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

The reality is that hiring amazing developers is hard. Terminal.io is your dedicated partner in rapidly standing up world-class remote technical teams. How do they deliver both speed and quality? Terminal does this by focusing on everything necessary to successfully source, setup, and support these teams – from physical elements like beautiful workspaces and equipment to ongoing resources like HR, payroll, legal, professional learning and development. But don’t take my word for this, take the word of Eventbrite, former 20VC guest Hims, and Dialpad – all customers and lovers of Terminal. You can find out more today at Terminal.io.

Whether you’re starting your own small business or getting serious about making your small business more efficient, you need to invite FreshBooks to the table. FreshBooks makes cloud accounting software that’s so ridiculously easy to use and you’ll quickly understand why over 10 million people use it to radically streamline how they deal with their admin and paperwork. Plus, FreshBooks can handle a lot more than accounting related tasks. Using FreshBooks is kind of like having your own admin assistant who’s got your back, 24/7. To claim your 30-day unrestricted free trial, click here enter Twenty Minute VC in the “how did you hear about us section”.

Highfive makes meetings better for thousands of organizations with insanely simple video conferencing designed for meeting rooms. It’s the easiest-to-use solution, with all-in-one hardware and intuitive cloud software. Plus, it’s a high-quality experience with industry-leading audio powered by Dolby Voice. It’s so easy to use, that there’s no pin codes or app downloads. Just click a link in your browser, and you’re in the meeting. With customers in over 100 countries, Highfive is already trusted by the likes of Warby Parker, Evernote, Expensify, and Betterment and you can learn more by simply heading over to highfive.com.

Pete Flint is a Managing Partner @ NFX, one of Silicon Valley’s newest and most exciting funds with the recent announcement of their new $150m fund late last year. Prior to VC, Pete was a serial entrepreneur building one of today’s most successful marketplaces, as the co-founder of Trulia. Pete led the company from inception to more than 50 million monthly unique users, $250m in VC funding from the likes of Sequoia and Accel culminating in their merger with Zillow in 2015 that valued Trulia at $3.5 billion. Before Trulia, Pete was part of the founding team of lastminute.com, a leading European online travel site that was acquired in 2005 for over $1 billion.

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In Today’s Episode You Will Learn:

1.) How Pete made his way into the world of startups joining the founding team of lastminute.com and how that led to the founding of Trulia and entry into VC?

2.) Why does Pete believe that startup timing is so crucial? How does Pete analyze market timing risk when investing? What is the right way for investors to think about the innovation cycle we are in today? On review, what does Pete believe lastminute.com did most right? What would he most want to change?

3.) What are the leading indicators that suggest potential in a network effect business? Would Pete agree with Josh @ Jackson Square that not all GMV is created equal? How does Pete analyse the lack of free and open distribution today and how that affects marketplace scaling? Why does Pete still believe marketplaces are some of the most capital efficient businesses to grow?

4.) What has been Pete’s greatest time of failure in his career? What is the framework Pete uses to analyze and assess his own ego? What are the commonalities in how Pete has seen truly great founders overcome failure? How does Pete balance between realism when something is not working and the mission and vision of the founder?

5.) How does Pete think about optimizing decision-making, both in investing and operating? How does Pete approach the balance of head vs heart? When is the right time to decide with your head? When is the right time to decide with your heart? Why does Pete argue early-stage investing must be decided with your heart?

Items Mentioned In Today’s Show:

Pete’s Fave Book: Leonardo Da Vinci 

Pete’s Most Recent Investment: Ribbon

As always you can follow Harry, The Twenty Minute VC and Pete on Twitter here!

Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

The reality is that hiring amazing developers is hard. Terminal.io is your dedicated partner in rapidly standing up world-class remote technical teams. How do they deliver both speed and quality? Terminal does this by focusing on everything necessary to successfully source, setup, and support these teams – from physical elements like beautiful workspaces and equipment to ongoing resources like HR, payroll, legal, professional learning and development. But don’t take my word for this, take the word of Eventbrite, former 20VC guest Hims, and Dialpad – all customers and lovers of Terminal. You can find out more today at Terminal.io.

Whether you’re starting your own small business or getting serious about making your small business more efficient, you need to invite FreshBooks to the table. FreshBooks makes cloud accounting software that’s so ridiculously easy to use and you’ll quickly understand why over 10 million people use it to radically streamline how they deal with their admin and paperwork. Plus, FreshBooks can handle a lot more than accounting related tasks. Using FreshBooks is kind of like having your own admin assistant who’s got your back, 24/7. To claim your 30-day unrestricted free trial, click here enter Twenty Minute VC in the “how did you hear about us section”.

Highfive makes meetings better for thousands of organizations with insanely simple video conferencing designed for meeting rooms. It’s the easiest-to-use solution, with all-in-one hardware and intuitive cloud software. Plus, it’s a high-quality experience with industry-leading audio powered by Dolby Voice. It’s so easy to use, that there’s no pin codes or app downloads. Just click a link in your browser, and you’re in the meeting. With customers in over 100 countries, Highfive is already trusted by the likes of Evernote, Expensify, and Betterment and you can learn more by simply heading over to highfive.com.

Joe Fernandez is the Founder & CEO @ JoyMode, the startup that allows you to lend everything you need to have the experiences you want. To date, Joe has raised over $16m in funding for Joymode from friends of the show including Homebrew, Slow Ventures, Founder Collective, Scott Belsky, Collaborative Fund and Lowercase, just to name a few. As for Joe, prior to founding JoyMode, Joe founded Klout, one of the leading social media analytics platforms of the day and raised $40m in funding from Kleiner Perkins, IVP, Venrock, Greycroft and more. Klout was ultimately acquired by Lithium Technologies where Joe sits on the board.

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In Today’s Episode You Will Learn:

1.) How Joe made his way into the world of startups with the founding of Klout? Given his entrepreneurial start, would Joe say he is unemployable?

2.) Question from Craig Shapiro: What was your single greatest lesson from the Klout journey? How has that impacted how you operate JoyMode today? How has Joe approached fundraising fundamentally differently today than with Klout? How is Joe’s team building strategy today different to his with Klout?

3.) Why does Joe believe that “serial entrepreneurs are over-rated”? What does Joe mean when he says, “you have to know which hill you are willing to die on”? How does Joe look to accurately ego check today? What innovative methods does Joe employ internally to ensure that his views are validated and not submitted to?

4.) What does Joe mean when he says, “you have to make big bets to win”? How can you implement this risk-taking mentality in larger teams? What is the right way for both the team and investor base to respond? How does Joe use continuous iteration and data-centricity to test and validate these theses?

5.) How does Joe approach investor update emails? Why does Joe look to terrify investors with each update? Does Joe believe that it is right to thanks specific individuals in those emails? Does like like to select individuals and request their help in the emails? How can past updates be used to attain future investors?

Items Mentioned In Today’s Show:

Joe’s Fave Book: The Accidental Superpower

As always you can follow Harry, The Twenty Minute VC and Joe on Twitter here!

Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

The reality is that hiring amazing developers is hard. Terminal.io is your dedicated partner in rapidly standing up world-class remote technical teams. How do they deliver both speed and quality? Terminal does this by focusing on everything necessary to successfully source, setup, and support these teams – from physical elements like beautiful workspaces and equipment to ongoing resources like HR, payroll, legal, professional learning and development. But don’t take my word for this, take the word of Eventbrite, former 20VC guest Hims, and Dialpad – all customers and lovers of Terminal. You can find out more today at Terminal.io.

Whether you’re starting your own small business or getting serious about making your small business more efficient, you need to invite FreshBooks to the table. FreshBooks makes cloud accounting software that’s so ridiculously easy to use and you’ll quickly understand why over 10 million people use it to radically streamline how they deal with their admin and paperwork. Plus, FreshBooks can handle a lot more than accounting related tasks. Using FreshBooks is kind of like having your own admin assistant who’s got your back, 24/7. To claim your 30-day unrestricted free trial, click here enter Twenty Minute VC in the “how did you hear about us section”.

Highfive makes meetings better for thousands of organizations with insanely simple video conferencing designed for meeting rooms. It’s the easiest-to-use solution, with all-in-one hardware and intuitive cloud software. Plus, it’s a high-quality experience with industry-leading audio powered by Dolby Voice. It’s so easy to use, that there’s no pin codes or app downloads. Just click a link in your browser, and you’re in the meeting. With customers in over 100 countries, Highfive is already trusted by the likes of Warby Parker, Evernote, Expensify, and Betterment and you can learn more by simply heading over to highfive.com.

 

Joel Monegro is Founding Partner @ Placeholder.VC, one of the new venture capital partnerships that invest solely in crypto assets and more specifically in decentralized information networks. Prior to founding Placeholder, Joel spent three years at Union Square Ventures developing the firm’s blockchain investment thesis and portfolio. Before USV, Joel started the Digital Economy Department at the Ministry of Industry and Commerce of the Dominican Republic, a government office in charge of developing the country’s national and technology agenda.

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In Today’s Episode You Will Learn:

1.) How Joel made his way into the world of VC with USV and what created his love of crypto and led to his leaving USV to found Placeholder? What were some of Joel’s biggest investing lessons from his time with USV?

2.) How does Joel approach portfolio construction in building out a crypto portfolio? How does the use of reserves and building positions change when comparing VC to crypto? Why does Joel believe that the most interesting place to invest in crypto is in the assets themselves, rather than the companies?

3.) When does Joel think we will see institutional capital begin to move into the space in a meaningful way? What needs to happen/change for this institutional interest to materialize? How is the element of “custody” crucial to the entrance of institutions?

4.) In terms of fund construction, liquidity is often an attractive element to crypto, why does Joel believe that a traditional venture fund structure is necessary for Placeholder? What are the benefits both to the fund and the projects it backs? How do LPs both traditional and non-traditional respond to this?

5.) Joel has said before the 2 core elements are crypto economics and governance, why does Josh believe this? Why is governance the foundational layer where value will accrue in the space? How does the lack of defensibility of crypto projects make governance ever more valuable?

Items Mentioned In Today’s Show:

Joel’s Fave Book: Antifragile by Nassim Taleb

Joel’s Most Recent Investment: Decred Investment Thesis

As always you can follow Harry, The Twenty Minute VC and Joel on Twitter here!

Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Whether you’re starting your own small business or getting serious about making your small business more efficient, you need to invite FreshBooks to the table. FreshBooks makes cloud accounting software that’s so ridiculously easy to use and you’ll quickly understand why over 10 million people use it to radically streamline how they deal with their admin and paperwork. Plus, FreshBooks can handle a lot more than accounting related tasks. Using FreshBooks is kind of like having your own admin assistant who’s got your back, 24/7. To claim your 30-day unrestricted free trial, click here enter Twenty Minute VC in the “how did you hear about us section”.

Highfive makes meetings better for thousands of organizations with insanely simple video conferencing designed for meeting rooms. It’s the easiest-to-use solution, with all-in-one hardware and intuitive cloud software. Plus, it’s a high-quality experience with industry-leading audio powered by Dolby Voice. It’s so easy to use, that there’s no pin codes or app downloads. Just click a link in your browser, and you’re in the meeting. With customers in over 100 countries, Highfive is already trusted by the likes of Evernote, Expensify, and Betterment and you can learn more by simply heading over to highfive.com.

 

Max Motschwiller is a Partner with Meritech Capital, one of the West Coast’s leading growth investment firms with over $150Bn in IPOs and a portfolio that includes the likes of Facebook, Salesforce, Snap, Box, Mulesoft and Cloudera just to name a few. As for Max, prior to Meritech he spent 3 years with Kleiner Perkins (KPCB) where he was actively involved with investments in Dropcam (Nest/Google), Duolingo, MyFitnessPal (Under Armour), RelateIQ (Salesforce.com) and Stance. Before joining KPCB, Max worked for 3 years at Summit Partners and was actively involved across Summit’s technology portfolio.

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In Today’s Episode You Will Learn:

1.) How did Max make his way into the world of VC with Summit and KP from University? What did that decision-making process look like for Max?

2.) As a career VC, would Max agree with Pat Grady @ Sequoia, “the rate of decay on operating experience has never been greater”? What would Max say are the biggest elements he missed through lack of operational experience? How do the skills required from early to pre-IPO change the type of background required?

3.) Max has said before, “to be a good VC you have to do 4 things well”, what are those 4 things? Why does Max believe that picking is the greatest skill to develop? At growth, what does Max mean when he says “the picking is around price”? How do the very best VCs approach price sensitivity?

4.) Question from Rob Ward: Max has mastered network development from an early age, what advice would Max give with regards to developing a network? What did he do well and works? What did he try and did not do well? How does Max think about depth vs breadth of network? How does he apply this to investing and due diligence?

5.) In a time of Softbank and Sequoia’s $7Bn fund, how does a firm like Meritech look to compete in such frothy environments? How has growth bifurcated into 2 clear stages? What are the advantages of being a small pure-play growth firm? How does the portfolio construction and return expectation change for you given the fund size and stage of investment?

Items Mentioned In Today’s Show:

Max’s Fave Book: Home Deus

Max’s Most Recent Investment: Amplitude

As always you can follow Harry, The Twenty Minute VC and Max on Twitter here!

Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Whether you’re starting your own small business or getting serious about making your small business more efficient, you need to invite FreshBooks to the table. FreshBooks makes cloud accounting software that’s so ridiculously easy to use and you’ll quickly understand why over 10 million people use it to radically streamline how they deal with their admin and paperwork. Plus, FreshBooks can handle a lot more than accounting related tasks. Using FreshBooks is kind of like having your own admin assistant who’s got your back, 24/7. To claim your 30-day unrestricted free trial, click here enter Twenty Minute VC in the “how did you hear about us section”.

Highfive makes meetings better for thousands of organizations with insanely simple video conferencing designed for meeting rooms. It’s the easiest-to-use solution, with all-in-one hardware and intuitive cloud software. Plus, it’s a high-quality experience with industry-leading audio powered by Dolby Voice. It’s so easy to use, that there’s no pin codes or app downloads. Just click a link in your browser, and you’re in the meeting. With customers in over 100 countries, Highfive is already trusted by the likes of Evernote, Expensify, and Betterment and you can learn more by simply heading over to highfive.com.