The Twenty Minute VC

Vinod Khosla is the Founder @ Khosla Ventures, one of the valley’s most renowned firms of the last decade with a portfolio including Square, Affirm, DoorDash, Impossible Foods and OpenDoor just to name a few. As for Vinod, he started his career as a Founder, founding Daisy Systems, a company that went on to IPO. Then in 1982, Vinod founded Sun Microsystems where he pioneered open systems and commercial RISC processors. In 1986, Vinod joined his longtime friend, John Doerr and became a General Partner @ KPCB where he helped incubate Juniper Networks and helped transform the telecommunications business with Cerent Corporation, which was acquired by Cisco Systems in 1999 for $7.2 billion.

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In Today’s Episode You Will Learn:

1.) How Vinod made his way into the world of startups with the founding of Daisy and Sun Microsystems and how that led to his entry into the world of venture with KPCB and ultimately founding Khosla Ventures?

2.) How does Vinod feel about the term “venture assistance” today? Where does Vinod believe VCs can really drive value? How does Vinod allocate his time to drive as much value for the portfolio as possible? How does Vinod get involved when it comes to talent acquisition for the portfolio?

3.) Why does Vinod believe that most board members are not qualified to advise entrepreneurs today? Why does Vinod believe that most value is driven outside of the board? What can founders to do make their boards as efficient as possible? How does Vinod advise founders to determine which advice to take vs which to disregard?

4.) How does Vinod assess his own approach and attitude to risk today? What does Vinod believe are acceptable vs unacceptable risks in startups? How does Vinod believe the very best founders think about risk management? Does Vinod agree time is the biggest killer of startups? Why does Vinod believe startups are so much quicker to innovate than incumbents?

5.) Why does Vinod believe that tolerance for failure has gone down in Silicon Valley? How does Vinod determine between the realism of when something is not work and to give up vs the visionary persistence to see a project through to the very end? What experience of his own have really led his thinking here?

Items Mentioned In Today’s Show:

Vinod’s Fave Book: Life on the Edge: The Coming of Age of Quantum Biology, The Third Pillar

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

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

Emmett Shear is the Co-Founder & CEO @ Twitch, the world’s leading live streaming platform for gamers and the things we love. Prior to Twitch’s exit to Amazon for a reported $970M, Emmett raised over $42M in funding from some of the best including Thrive Capital, Bessemer, Mike Maples, Aydin Senkut, Paul Graham and Y Combinator. Emmett is also a part-time Partner @ Y Combinator, advising YC companies on everything from fundraising strategy to product decisions to hiring and firing. Before Twitch, Emmett co-founded Kiko, a company he later sold on eBay for 6 figures.

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In Today’s Episode You Will Learn:

1.) How Emmett made his way into the world of startups with Kiko? How he ended up selling that for 6 figures on eBay? How that led to the creation of Justin.TV & Twitch?

2.) Why does Emmett believe starting a startup is like “deciding to take on the burden of Sisyphus?” At what point in the journey does is start to get easier? Does Emmett agree with many on the show who say, “it does not get easier, it just gets different”? How does one know when to give up vs when to persist and follow the vision?

3.) How does Emmett think about structuring an org at 1,500 people? Why does Emmett believe there is a fundamental tension when scaling teams between centralisation and decentralisation? How does one structure a reorg without causing instability? How does one communicate the reorg to the team? Where does Emmett see many go wrong here?

4.) Does Emmett agree the best CEOs are the best resource allocators? How does Emmett approach internal resource allocation today between both functions and projects? What does he find most challenging here? What does the decision-making process look like? What are his takeaways from Apple, Amazon and Microsoft in how they determine and process resource allocation internally?

5.) How does Emmett believe he has changed and evolved as a leader over the last 10 years with Twitch? What elements has he found the most challenging to master? What has he done to combat those weaknesses? Where has he always been naturally strong? What makes him so good at those particular functions?

Items Mentioned In Today’s Show:

Emmett’s Fave Book: Order without Design: How Markets Shape Cities

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

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

Ashton Kutcher is a Founder & General Partner @ Sound Ventures. Over the last 5 years, Ashton and his partner, Guy Oseary, have built Sound into one of the West Coast’s leading new entrants with a portfolio including Lambda School, Calm, Gitlab, Affirm, Bird and many more incredible companies. As for Ashton, he started his investing career as an angel with early home runs including Spotify, Alibaba, Skype, Airbnb and Optimizely. Due to his immense success both in media and technology, Ashton has been named one of TIME magazine’s “100 Most Influential People in the World”.

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In Today’s Episode You Will Learn:

1.) How Ashton made his way into the world of startups with his foray into angel investing in Skype, Spotify etc? How did that lead to his founding Sound Ventures most recently?

2.) How does Ashton’s background in the world of media impact Sound’s investment strategy and the type of deals they get excited by? Question from Daniel Ek @ Spotify: How did your deal sourcing look lin the early days? How has that changed over time and with the institutionalisation of Sound?

3.) Why does Ashton believe people creating the future are perpetually young? What question does Ashton always like to ask founders? What does he look for in their answer? How does Ashton ensure founders feel comfortable with him? What does he do to allow them to open up? What is the hardest thing Ashton feels he has persevered through?

4.) How does Ashton build strong product intuition about products in areas he is not familiar with? In terms of great product, Ashton backed Spotify with Daniel Ek and Shak Khan, what did Ashton see in Spotify way back then? How did Shak and Daniel innovate on distribution and customer acquisition with him and Spotify?

5.) What have been Ashton’s learnings in what it takes to truly win the best and most competitive deals? Before as an angel, Ashton’s check size was friendly, now with Sound it is competitive with VCs, how does Ashton approach the element of now competing with many VCs he once co-operated with? What does Ashton make of the rise of many celebrity investors today?

Items Mentioned In Today’s Show:

Ashton’s Fave Book: The Undoing Project: A Friendship that Changed the World, Scale: The Universal Laws of Life and Death in Organisms, Cities and Companies

Ashton’s Most Recent Investment: Community

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

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

 

Gabriel Weinberg is the Founder & CEO @ DuckDuckGo, the Internet privacy company that empowers you to seamlessly take control of your personal information online, without any tradeoffs. Over the last 12 years, Gabe has scaled DuckDuckGo to doing 1.6Bn private searches every month, a team of 83 full time fully remote employees, raising funding from some of the best in the business; USV and most importantly, being a profitable company. If that was not enough, Gabe has also written two phenomenal books, Traction and Super Thinking. 

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In Today’s Episode You Will Learn:

1.) How Gabriel made his way into the world of startups and came to found one of today’s leading search engines and privacy companies in DuckDuckGo?

2.) Gabriel decided to raise from USV 4 years into the life of DDG, why did he believe that was the right time? Why does Gabe believe that DDG never needed any primary capital? How does Gabe advise founders to think when it comes to chasing profitability early? How does Gabe view the relationship between growth and capital? Are they in conflict or aligned? What does Gabe make of the many $100M rounds getting done today?

3.) How does Gabe feel about the lack of free and open distribution today? How does Gabe strategise when it comes to channel diversification? What is the right level of marketing channel diversification to have? How do you know when to really double down on one that is working? How should founders be thinking about channel saturation rates? What have been Gabes biggest lessons on payback period over the last 12 years with DDG?

4.) How does Gabe feel about the digital advertising duopoly on the internet between Facebook and Google? Why does Gabe argue that this duo of incumbents are so much more powerful than any other prior generation of incumbents? How does Gabe think about strategies to reduce their data monopolies?

5.) DDG is 83 people and fully remote, what have been Gabe’s biggest lessons on what it takes to run a fully-remote team from Day 1? What mistakes did they make? WHat would Gabe advise founders contemplating the fully remote strategy? Why does Gabe have nor formal hierarchy or org chart internally at DDG? Why is this so important for culture and employee morale?

Items Mentioned In Today’s Show:

Gabe’s Fave Book: The Advantage: Why Organizational Health Trumps Everything Else In Business

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

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

Jude Gomila is the Founder & CEO @ Golden, creating the world’s first self-constructing knowledge database built by artificial and human intelligence. To date, Jude has raised from some of the best in the business including Founders Fund, a16z, SV Angel and one of my dearest friends, Josh Buckley. Jude is also a prolific angel having invested in over 150 companies including Carta, Airtable, Superhuman, Gusto, Linear and many more incredible companies. Prior to Golden, Jude started Heyzap (now used by 100,000 mobile apps) alongside former guest Immad, now Founder of Mercury.

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In Today’s Episode You Will Learn:

1.) How Jude made his way into the world of tech and Silicon Valley having been born and raised in Harrow, London? How did he then make his way into the world of investing?

2.) What models should investors and founders have common ground on? Where are founders and investors often misaligned? What does Jude mean when he says he uses “algorithms for investing”? How are these algorithms structured? What is within them? How can/should people build their own?

3.) Why does Jude very much disagree with spray and pray to be the dominant model to make money at seed? How does Jude think about portfolio construction having now made 180 investments? How has Jude’s approach and attitude to ownership changed over time?

4.) Does Jude agree with Semil Shah that founders are voting with their feet and taking multi-stage money at seed today? How does Jude evaluate the approach of multi-stage funds back into seed? How does Jude think about VC value add? Where does he believe they really can add value? Where do people think they do but they actually do not?

5.) How does Jude foresee the future of the early-stage market? Will we see a generation of old school venture firms die out? Why does Jude believe younger investors have a higher chance of finding and winning the next best deal? How does Jude believe the angel ecosystem will shake out? Will we fundamentally see the unbundling of capital?

Items Mentioned In Today’s Show:

Jude’s Fave Book: Godel, Escher, Bach: An Eternal Golden Braid

Jude’s Most Recent Investment: Linear

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

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

Shoaib Makani is the Co-Founder & CEO @ KeepTruckin, the modern fleet management platform building solutions that make drivers and fleets safer, smarter, and more efficient. To date, Shoaib has raised over $229M from some of the world’s leading investors including Index, GV, Greenoaks, IVP & Scale Venture Partners. Pre-founding KeepTruckin, Shoaib was an investor @ Khosla Ventures where he led investments in Instacart, Everlane and Indiegogo to name a few. Before venture with Khosla, Shoaib was on the operations side enjoying roles at both Google and Admob.

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In Today’s Episode You Will Learn:

1.) How Shoaib made his way from the very comfortable world of venture to changing the way trucking fleets are managed today with KeepTruckin? How does Shoaib analyse and assess his own attitude to risk today?

2.) How has Shoaib seen himself change and evolve as a leader over the last few years? How did his time investing impact how he approaches the role of CEO? How does Shoaib think about appropriate market sizing today? What advice does he give to founders on this? What is a reasonable market penetration to assume if successful?

3.) What advice would Shoaib give founders when it comes to successful board management? How does Shoaib ensure investors have the right context at the right time to provide advice? What does that information flow to investors look like? How does Shoaib determine between the advice to accept vs what to reject?

4.) Shoaib thought about distribution and customer acquisition long before he launched the product, why? What did this thought process conclude with? Does Shoaib believe you have to own your own lines of distribution to succeed? How does Shoaib feel when it comes to current CAC’s on incumbent platforms?

4.) As a founder, what does Shoaib say is his biggest mistake made in the KeepTrickin journey? How does Shoaib think about what it takes to acquire the very best talent? How does Shoaib advise founders work with recruiters? What can they do to really get the most out of them? When can this function be brought in house?

Items Mentioned In Today’s Show:

Shoaib’s Fave Book: Presidents of War

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

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

 

 

Todd Jackson is First Round Capital‘s newest Partner (announced today) having spent the last 2 years as a Founder-in-Residence working with the FRC portfolio. Prior to his time in venture, Todd spent close to 3 years at Dropbox as VP Product & Design. Before that he was with Twitter as Director of Product Management, following his startup, Cover, being acquired by Twitter in 2014. Before founding Cover, Todd was a Product Manager @ Facebook where he helped lead major redesign of Newsfeed. Finally, Todd started his career at Google as a Product Lead taking Gmail from 0 to 200m users in 4 years.

Todd is joined today by his Partner @ First Round, Phin Barnes. 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.) Phin, what is the exclusive news you would like to break on the show today? Todd, taking one step back, how did you make your way to this stage, what was your entry into technology and how did you come to be a Partner @ First Round Capital today? What were Todd’s biggest takeaways from working on some of the most transformative social products in Gmail, Twitter, Newsfeed @ Facebook and Dropbox?

2.) What advice does Phin have for Todd when it comes to entering a venture partnership? Where do many people go wrong in their first year in venture? What should Todd be optimising for in the partnership? In terms of measurement, how does one measure success of the first year of work as a Partner?

3.) Todd, making the move from angel to institutional VC is a mindset shift, how does Todd think his investment mentality will be impacted by the shift from angel to institutional VC? Having raised funding as a founder, what type of founder experience and investor does Todd want to be and bring?

4.) Phin, it has been a long time since FRC added a Partner, walk me through the recent changes at the top of FRC? What are the most important qualities for First Round when adding a Partner? What are the biggest tips to doing generational transition well? Where do many firms go wrong in generational transition?

Items Mentioned In Today’s Show:

Todd’s Fave Book: Creative Selection: Inside Apple’s Design Process During the Golden Age of Steve Jobs, Trillion Dollar Coach: The Leadership Handbook of Silicon Valley’s Bill Campbell

Todd’s Most Recent Investment: Papaya Payments, Snackpass

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

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

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Alexa Von Tobel is the Founder & Managing Partner @ Inspired Capital, announced in 2019 as the largest ever female-led VC fund based in NYC. Prior to co-founding Inspired, Alexa founded LearnVest where she enjoyed an incredible 11-year journey culminating in their $250M exit to Northwestern Mutual in 2015. Alexa is also the author of New York Times Bestseller “Financially Fearless” and is an inaugural member of the Presidential Ambassadors for Global Entrepreneurship for the White House.

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In Today’s Episode You Will Learn:

1.) How Alexa made her way into the world of startups with the founding of LearnVest? How did that experience running LearnVest lead to her founding NYC’s largest-ever female-led VC fund in the form of Inspired?

2.) How does Alexa think about portfolio construction with the new $200M fund? What does she mean when she says they have segmented it into 3 distinct and separate buckets? How much is in each bucket? How does Alexa think about reserves and re-investment decision making? What is the process here?

3.) As a former entrepreneur, how does Alexa think about those moments when the VC and the Founder are no longer aligned? What are those moments? How does Alexa approach the aspect of saying no to founders? What is the right way? How does Alexa feel about the compression in fundraising timelines? How does Alexa meet founders before they raise their round?

4.) Why does Alexa believe that capital is no longer the differentiator? How does Alexa think about personal brand in venture today? Where does Alexa believe are the most crucial times for reputation building? How does Alexa approach time allocation across the portfolio? What is the correlation between decision-making and reputation?

Items Mentioned In Today’s Show:

Alexa’s Fave Book: The Power of Moments: Why Certain Experiences Have Extraordinary Impact

Alexa’s Most Recent Investment: Snackpass

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

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

Katie Stanton is the Founder and General Partner of Moxxie Ventures, investing in founders who make life and work better. Prior to Moxxie, Katie was a Founding Partner of #angels and has the most incredible angel portfolio including Airtable, Carta, Cameo, Coinbase and Modern Fertility to name a few. Katie also served in numerous executive operating roles at Twitter, Google, Yahoo, and Color and also served in the (Obama) White House and State Department. If that was not enough, Katie is also on the board of Vivendi and previously sat on the board of Time Inc.

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In Today’s Episode You Will Learn:

1.) How Katie made her way into the world of tech with Yahoo? How did that translate into her investing in Lowercase Fund I? How did the angel investing lead to founding Moxxie? How has Katie found her investment mindset has changed moving from angel to VC?

2.) How did Katie find the fundraise for Moxxie? How many LPs did Katie meet and how did she structure the process? What does Katie think she did well in the fundraise? What would she look to improve or change when raising for Fund II? What advice was Katie given in the process by Semil Shah which really changed her thinking? What advice would Katie give to other emerging managers raising today?

3.) Does Katie agree with Semil Shah that “founders are voting with their feet in taking multi-stage money at seed”? What advice does Katie give to founders who do have these offers from multi-stage funds at seed? How does Katie assess these later stage funds moving earlier? How should smaller micro-managers respond to this?

4.) How does Katie think about portfolio construction today with Moxxie? What are the hard rules that mean Katie is willing to walk away from a deal? How does Katie think about and assess her own price sensitivity? In terms of decision-making, what support system has Katie built around herself to enhance her decision-making process?

5.) How does Katie advice founders when it comes to selecting their VC? What are the most common ways founders look for and need to help with? How does Katie think about party rounds? When are they good? When are they not? Why does Katie believe so much of the power has shifted to the hands of the founders?

Items Mentioned In Today’s Show:

Katie’s Fave Book: Becoming by Michelle Obama, Angel by Jason Calacanis

Katie’s Most Recent Investment: ethel’s club

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

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

Rick Nucci is the Co-Founder & CEO @ Guru, the knowledge management platform that delivers everything you need so you can spend less time searching and more time doing. To date, Rick has raised over $38m with Guru from some of the best in the business including Thrive, Emergence Capital, Firstmark, Slack and Salesforce. Prior to Guru, Rick was the Founder of Boomi, which defined and led a new segment as the first-ever cloud integration platform-as-a-service. Boomi was ultimately acquired by Dell where Rick went on to grow the organisation into the industry leader it is today.

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In Today’s Episode You Will Learn:

1.) How Rick made his way into the world of startups originally and how he came to change the way we think about knowledge management with his founding of Guru?

2.) How would Rick describe his leadership style today? How has he seen his style change over the years? What have been those learnings and the inflexion points causing them? Does Rick believe can be learned as a leader? What does he recommend to founders wanting to become more empathetic?

3.) Culture is a fluffy and overused term, what does it mean to Rick? What has Rick done to purposefully build a very specific culture that he wanted to create? What specific initiatives have worked well? What have not worked so well? How does Rick think about culture maintenance with scale? What are the challenges with scaling culture?

4.) How does Rick think about the interview process when adding to the team at Guru? How do they literally structure it? What does their culture interview encompass? How heavily is it weighted? What specific questions do they ask and responses they look for? If it does not work out, what have been Rick’s biggest lessons on letting people go?

5.) Rick is based in Philadelphia, often people say if you are not in a tech hub it is not possible to get the best talent, does Rick agree with this? In what roles does it make sense to hire from a tech hub for? What are the advantages of hiring outside of a hub? Fundraising wise, does Rick believe you have to have a presence in a core hub to raise from Tier 1 VCs?

Items Mentioned In Today’s Show:

Rick’s Fave Book: The 9 Types of Leadership: Mastering the Art of People in the 21st Century Workplace

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

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

 

 

Howard Marks is co-chairman and co-founder of Oaktree Capital Management, a leading investment firm with more than $120 billion in assets. Prior to founding Oaktree, Howard spent 10 years at The TCW Group, where he was responsible for investments in distressed debt, high yield bonds, and convertible securities. Previously, Howard was with Citicorp for 16 years, where he served as Vice President and senior portfolio manager in charge of convertible and high yield securities. Howard has also written two books, most recently Mastering the Market Cycle: Getting the Odds on Your Side, and it was Warren Buffet who said, “When I see memos from Howard Marks in my mail, they’re the first thing I open and read. I always learn something.”

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In Today’s Episode You Will Learn:

1.) How Howard first made his way into the world of finance over 50 years ago? How did not getting an investment banking job change the course of Howard’s life?

2.) Where does Howard think we are in the cycle today? What leads his thinking here? What is it crucial for all investors to remember at any point in the cycle? From a risk distribution and diversification perspective, does Howard believe now is a better or worse time to increase risk?

3.) Having worked through and been at the forefront of some of the most significant downturns of financial markets, what have been Howard’s biggest learnings from seeing the booms and busts? How did it impact his investment mindset? At a point in 2008, Oaktree were deploying $600M per week for 15 weeks running, so how does Howard think about when is the right time to be aggressive vs when to pullback?

4.) How does Howard think about and assess his own price sensitivity? If there is one thing Howard wants to know to determine the right price, what is it? How does Howard believe we are seeing pro-risk mindsets alter investors attitude to price? How does Howard think about his right vs wrong and consensus vs non-consensus matrix?

5.) Howard and his Partner, Bruce have a very special relationship, what have they done to foster a relationship of radical intellectual honesty and that environment of safety? What are some things Howard will say to his team to encourage productive disagreement? What to Howard is the most important skill an investor can have is?

Items Mentioned In Today’s Show:

Howard’s Fave Book: Fooled by Randomness: The Hidden Role of Chance in Life and in the Markets

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.

Sumeet Gajri is the Chief Strategy Officer @ Carta, the startup that helps companies and investors manage their cap tables, valuations, investments, and equity plans. Sumeet is largely responsible for all things fundraising and M&A and Carta have raised over $485m from a16z, USV, Thrive, Spark, K9, Lightspeed and Meritech to name a few. Sumeet is also Managing Partner @ Original Capital, where he has partnered with companies including Front, Tonal, Instabase, Everlywell and Cockroach Labs to name a few. Finally, Sumeet is also an LP in world-leading firms such as USV and Valar Ventures.

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In Today’s Episode You Will Learn:

1.) How Sumeet made his first foray into the world of venture in NYC having grown up in Scotland? How that led to his move to operations with Carta? How his learnings from Carta led to his establishing Original Capital?

2.) How is Original Capital different from every other micro-fund? How does Sumeet approach portfolio construction with the fund? What is the optimal number in a portfolio? How does Sumeet think about loss ratio? What 3 criteria dos every new investment have to pass to make it into the portfolio? How does check size vary by deal?

3.) How does Sumeet invest in some of the best companies in between “official rounds”? What does this conversation look like with the founders? How does Sumeet analyse reserve allocations? What makes the right strategy? What are his capital concentration limits per company? How does Sumeet think about using SPVs effectively?

4.) Sumeet helps his companies fundraise a lot, what does the first step look like? How does he advise on investor selection? How does he advise on pipeline management? Should founders speak to investors when they are not raising? How open should they be in these meetings? What can founders do to catalyse the process? Where does Sumeet see many founders make mistakes?

5.) How does Sumeet think about distribution vs product? What can founders do to adopt a more distribution first mindset? What have been some of Sumeet’s biggest lessons in turning Carta from a single product company to a multi-product company? Do companies have to own their own lines of distribution today?

Items Mentioned In Today’s Show:

Sumeet’s Fave Book: Howard Marks: The Value of Predictions

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

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

Samir Kaul is a Founding Partner and Managing Director at Khosla Ventures, one of the valley’s most renowned firms of the last decade with a portfolio including Square, Affirm, DoorDash, Impossible Foods and OpenDoor just to name a few. As for Samir, he led the firm’s investment in Guardant Health, Impossible Foods, Nutanix [NASDAQ: NTNX], Oscar, among others. Prior to Khosla, Samir spent five years at Flagship Ventures where he started and invested in early-stage biotechnology companies, including Helicos Biosciences which went on to IPO. Samir was also founding CEO of Codon Devices and led the Arabidopsis Genome Initiative at Craig Venter’s Institute for Genomic Research.

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In Today’s Episode You Will Learn:

1.) How Samir made his way into the world of venture from the world of biotech and came to found one of the leading firms of the last decade?

2.) How did seeing the booms and busts of the last 2 decades impact Samir’s investing mindset? Why does Samir think it is dangerous for a VC to have a “conservative mindset”? How does Samir analyse and think about upside maximisation when investing today? How does Samir think about when to sell your position and how to determine the right time?

3.) What does investment decision-making look like at Khosla? What are the criteria that re-investments are made upon? Why does Samir believe that pro-rata is a kop out? Which should be the core questions that determine whether to double down or not? How does Samir and the partnership think about time allocation across the portfolio?

4.) How does Samir approach the exercise of market sizing? Why does Samir never want to take a risk when it comes to market? Why does Samir want to maximise his risk when it comes to technological risk? How does Samir think through having to carry these deep tech companies for longer? What were his learnings from the clean tech days on this?

5.) How would Samir analyse his own price sensitivity today? What was his most formative inflexion moment as an investor? What did he learn from it? From a people side, who had the biggest impact on Samir as an investor? What were the core elements he learned from them? How does Samir deal with the element of self-doubt? How does he get through those moments?

Items Mentioned In Today’s Show:

Samir’s Fave Book: Start Something That Matters

Samir’s Most Recent Investment: Lightship: Direct to Patient Clinical Trials 

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

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

Kurt Rathmann is the Founder & CEO @ ScaleFactor, the startup providing an automated bookkeeping solution at its core, bringing all of your company’s important financial information into one place. To date, Kurt has raised over $105m with ScaleFactor from the likes of Byron Deeter @ Bessemer, Coatue, Canaan Partners, Stripes Group and Firebrand to name a few. As Michael @ Coatue told me before the show, there is no way Kurt was not going to be the founder of a bookkeeping company given his background. Prior to ScaleFacotr, Kurt was the CFO of KNS Communications and a Senior Audit Professional @ KPMG.

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In Today’s Episode You Will Learn:

1.) How did Kurt make his way into the world of startups and come to found the gamechanger for bookkeeping in the form of ScaleFactor? Does Kurt believe that Founders do need to be mission-driven or can founding a company be a more analytical exercise?

2.) How did it come to be that Kurt raised 3 separate funding rounds and over $105m in just 13 months? How does Kurt feel about the saying, “when there is money on the table, take it”? Having had his B and C pre-empted, how does Kurt feel about the rise of pre-emptive rounds today? How did Kurt approach the mental challenge of transitioning from resource-starved to relative resource abundance? Was that tough to do?

3.) What is Kurt’s biggest advice to founders when it comes to investor selection? What does Kurt believe are the 5 things that VCs can do to add value? Why does Kurt believe it is the responsibility of the founder to extract that value from the VC? What can founders do to really get the most out of their investors? What has Kurt found to be the biggest value from his cap table? Where do founders think VCs add value but they do not?

4.) What are some very unique and deliberate things that Kurt does to create an amazing culture at ScaleFactor? How does he advise on creating great energy in the office itself? How does Kurt think about retaining that core ethos with the expansion to multiple offices? What have been some of the biggest challenges in scaling communications internally?

5.) Does Kurt believe that being outside of a core tech hub severely limits his ability to hire the best talent? What do founders outside of these hubs need to very strategically do? How does being outside of a core hub also impact how Kurt thinks founders need to approach fundraising? What specifically can they do to increase their odds?

Items Mentioned In Today’s Show:

Kurt’s Fave Book: The Empowered Challenger Playbook: How Brands Can Change the Game, Steal Market Share, and Topple Giants

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

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

 

Gaurav Jain is Co-Founder & Managing Partner @ Afore Capital, one of the west coast’s leading pre-seed funds with a $124M fund focused purely on pre-seed. To date, they have backed the likes of Petal, BetterUp, BenchSci and Modern Health to name a few. Prior to co-founding Afore, Gaurav was a Principal @ Founder Collective where he was directly involved with some incredible companies including Cruise (Acq. by General Motors for $1B+), Periscope (acq. by Twitter), Airtable and Dia & Co. Before venture, Gaurav spent time in operations both at Google as one of the first engineers for Android and then also founding his own company, Polar, a leading mobile solutions provider with $10m in funding.

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In Today’s Episode You Will Learn:

1.) How Gaurav made his way into the world of venture with Founder Collective and how that led to the realisation that Afore needed to exist in the funding landscape? What were the 3 biggest takeaways for Gaurav from his time at Founder Collective?

2.) Why does Gaurav believe now is the hardest time in the last decade to raise your first institutional round of funding? What is driving these capital reductions at pre-seed? How does Gaurav assess the rise of operator funds and super angels we have seen in the last 5 years? How does Gaurav advise founders on investor selection at pre-seed?

3.) What does Gaurav make of large multi-stage funds entering into pre-seed? Why does Gaurav strongly believe that you cannot apply the same financing product to a different market? Does this mean the multi-stage funds will revert back to later stages?

4.) How is Gaurav seeing Series A funds behaving? Why are they more aggressive now than ever before? What does Gaurav make of the rise of pre-emptive rounds? How does he advise founders on pre-emptive rounds?

5.) How does Gaurav think about portfolio construction today with Afore? What is the right level of diversification across the portfolio to be sufficiently diversified at pre-seed? How does Gaurav think about reserve allocation today? How does the decision-making process compare when comparing initial to re-investment decision?

Items Mentioned In Today’s Show:

Gaurav’s Fave Book: Trillion-Dollar Coach: The Leadership Handbook of Silicon Valley’s Bill Campbell

Gaurav’s Most Recent Investment: Modern Health

As always you can follow Harry, The Twenty Minute VC and Gaurav 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.

Rob Salvagno is VP of Corporate Development and Cisco Investments at Cisco, where he is responsible for leading all M&A efforts as well as managing Cisco’s strategic venture capital which invests hundreds of millions of dollars annually. At Cisco, Rob led the $1.2 billion acquisition of Meraki, one of the most successful platform acquisitions in Cisco’s history, and the $3.7 billion acquisition of AppDynamics, cementing Cisco’s place in the business intelligence, analytics and IT operations market. Most recently, Rob engineered the $2.3 billion acquisition of Duo, the leading provider of unified access security and multi-factor authentication delivered through the cloud. Prior to the world of M&A, Rob was a technology investment banker at Donaldson, Lufkin & Jenrette.

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In Today’s Episode You Will Learn:

1.) How Rob made his way from investment banking to leading the M&A and venture activity for one of the world’s largest tech players of the last decade?

2.) How do M&A teams like to get to know startups that they could invest in or acquire? How does Rob like to work with the venture ecosystem? How does Rob think on Paul Graham’s comment of “do not talk to corp dev”? What are the nuances here? How does it differ for consumer vs enterprise?

3.) How does Rob define true success when it comes to M&A evaluation? Should corp dev be strategy first or transaction first? What have been Rob’s biggest lessons on successful integration? Where do so many go wrong with integration post M&A? What questions can be asked ahead of time to know if integration and culture will be a fit?

4.) How does Rob reflect on his own price sensitivity today? How does Rob feel about the multiples enterprise companies are currently trading at? What have Rob’s most successful acquisitions taught him about price and price sensitivity? How does Rob deal with the inherent conflict of investing and also acquiring companies? How does he communicate that to the companies he invests in?

5.) What does the acquisition-decision making process look like at Cisco? How does it differ on a deal by deal basis? What do Cisco do to allow them to move so much faster than any other M&A teams? What have been Rob’s lessons on the importance of speed in winning the best transactions?

Items Mentioned In Today’s Show:

Rob’s Fave Book: The Poisonwood Bible

Rob’s Most Recent Acquisitions: CloudCherry, Voicea

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.

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.

Brandon Deer is VP of Operations & Strategy @ UiPath, one of the world’s fastest-growing companies providing a complete software platform to help organizations efficiently automate business processes through robotic process automation. To date, UiPath has raised over $977m in funding from some of the best in the world including Sequoia, Accel, Meritech, IVP, CapitalG, Kleiner Perkins, Coatue and more. As for Brandon, prior to UiPath he spent 4 years as Vice President @ OpenView Partners where he made investments in Expensify, Logz.io, VTS and Pipefy to name a couple. Before OpenView, Brandon spent close to 4 years at Intuit in Strategy and Business Development.

Adam D’Augelli is a Partner @ True Ventures, one of the West Coast’s leading early-stage funds with a portfolio including the likes of Fitbit, Peloton, Hashicorp, Tray.io, Ring, Automattic (makers of WordPress) and many more amazing companies. As for Adam, he has spent close to 10 years at True where he has led investments in Hashicorp, Ring, Splice and Namely, just to name a few. Prior to joining the world of venture with True, Adam was an instructor at The University of Florida in Business Finance. Before that Adam was the Founder of Perfect Wave Records, a donation-based record label – helping bands better monetize the relationships with their fans.

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In Today’s Episode You Will Learn:

1.) How Adam made his way into the world of venture with True and how that start came about?

2.) How does Adam think about portfolio construction today with True? Is it still possible to get 20% ownership on first check? Does Adam believe you can build ownership in subsequent rounds? Does this mean we are seeing the end to rounds being co-led? What does Adam make of pre-emptive rounds? How do True respond to them today?

3.) How does True think about initial vs re-investment decision-making? How do the decision processes differ? Does Adam believe it is possible to stack rank companies and allocate capital accordingly? What is the right way to tell a founder you will not be re-investing? How does Adam think about risk maximisation at a company level?

4.) As a partnership, how does True look to create an environment of safety where both conviction and concerns can be expressed? What should partnerships not do? Why is attribution so dangerous to this EQ of the partnership? How does the partnership work with the companies at a company level? How does True view board seats? How does True think about when is the right time to roll off boards?

5.) What were Adam’s biggest takeaways from leading Ring’s seed to their acquisition by Amazon? How does Adam think about the importance of market vs the importance of people when investing? How does Adam think about company failure, post-mortems and subsequent next steps?

Items Mentioned In Today’s Show:

Adam’s Fave Book: Doing Capitalism in the Innovation Economy: Markets, Speculation and the State, Technological Revolutions and Financial Capital: The Dynamics of Bubbles and Golden Ages

Adam’s Recommended Whitepaper: Investing in the Unknown and Unknowable

Adam’s Most Recent Investment: Membio

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.

John Vrionis is the Founder and Managing Partner @ Unusual Ventures, the firm that is redefining seed investing and raising the bar for what entrepreneurs should expect from a seed investment firm. Prior to founding Unusual, John spent 11 years as a Partner @ Lightspeed where his investments included Mulesoft, AppDynamics, Nimble Storage and Heptio to name a few. Before Lightspeed John spent time in product management and sales @ Determina and Freedom Financial Network.

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In Today’s Episode You Will Learn:

1.) How did John make his way into the world of venture and come to be a Partner @ Lightspeed? How did that lead to his founding Unusual? How did his father’s MS diagnosis change his mentality towards both investing and how he views the world? What were John’s biggest takeaways from his 12 years with the Lightspeed partnership?

2.) Where does John feel the bar needs to be raised in venture? What does the current product not offer? What do seed-stage founders fundamentally need? How have Unusual structured the firm to provide this? How was the fundraise for John? What does John know post-closing that he wishes he had known at the beginning? What advice would John give to aspiring emerging managers? Why is LP diversity so important to John?

3.) Why does John believe taking multi-stage money at seed is not in the best interests of the founder? How does John explain this logically to founders? Does John agree with Semil Shah, “founders are voting with their feet and choosing multi-stage funds”? Why does John believe to be truly best in class, you have to specialise? Does this not go against the data of Benchmark, Sequoia, Founders Fund, all generalist funds, having the best returns?

4.) How does John think about being company vs being founder first? What does one do when alignment erodes between the interest of the firm and the interest of the founder? How does John look to build a relationship of trust and honesty with his founders? What works? What does not work? How does John feel about VCs being friends with their founders?

5.) What is the most challenging element of John’s role today with Unusual? Who is the best board member John has ever sat on a board with? Why and what did he learn? What would John most like to change about the world of venture today? What would he like to remain the same?

Items Mentioned In Today’s Show:

John’s Fave Book: Shoe Dog: A Memoir by the Creator of NIKE, Give and Take: Why Helping Others Drives Our Success

John’s Most Recent Investment: Shujinko

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

Emmanuel Schalit is the Founder & CEO @ Dashlane, the company that provides your all-in-one internet shortcut for passwords, payments and personal info. To date, Emmanuel has raised over $192m in funding for Dashlane from some of the best in the business including Jim Goetz @ Sequoia Capital, Rick @ Firstmark, Alex @ Bessemer and Habib @ Rho, just to name a few. As for Emmanuel, prior to founding Dashlane, he was the CEO @ CBS Outdoor in France and before that COO @ La Martiniere Group.

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In Today’s Episode You Will Learn:

1.) How Emmanuel made his way from CEO of 5,000+ people companies to founding Dashlane and changing the world of passwords and identification? How does Emmanuel asses his own risk profile moving from CEO of a large company to starting Dashlane?

2.) Is Emmanuel concerned by the excess capital available today? Why does Emmanuel believe that raising a mega-round makes your life as a founder harder, not easier? What specifically becomes harder? How does Emmanuel advise founders when it comes to burn and capital efficiency? How does Emmanuel think about when is the right time to pour fuel on the fire?

3.) Where does Emmanuel think that VCs do tangibly add real value? Where does Emmanuel believe that despite what some think, VCs do not add value in certain areas? What have been Emmanuel’s biggest lessons of operating and managing a VC board? What does he advise founders starting out on this learning curve?

4.) What does Emmanuel believe are the core challenges of scale? What breaks at what specific points? How has Emmanuel seen himself scale in his role as CEO? What have been the most challenging element to scale into? How did Emmanuel get through them and what does he do to mitigate them now?

Items Mentioned In Today’s Show:

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

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

David Tisch is the Founder & Managing Partner @ BoxGroup, one of the leading early-stage firms in NYC with a portfolio that includes the likes of Flexport, RigUp, Ro, Glossier, Clearbit, PillPack and Plaid, to name a few. Recently they raised their first external capital with 2 separate vehicles totalling over $160m. David is also Professor and Head of Startup Studio @ Cornell Tech. Prior to Box Group, he was Managing Director of Techstars NYC and before that was an Executive Vice President @ KGB.

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In Today’s Episode You Will Learn:

1.) How David made his way into the world of early-stage investing? How he made the transition from prolific angel investor to raising $160m+ in external capital? Why did David feel now was the right time to raise external funding after 10 years of self-funding? How has taking on external capital changed his investing mindset?

2.) Many suggest that “concentrated seed investing does not work”, how does David think about and assess portfolio construction? May others also suggest that, “seed investors are not company builders”, does David agree with that? Does David believe investors can change the trajectory of a company? Where can they help the most? Where do many think they help but they actually do not?

3.) Why does David believe that founders do not speak openly about bad experiences with VCs? What have been David’s biggest lessons on the right way to turn down an opportunity? Do founders really want direct and honest feedback? Is it actually damaging to give it to them? Why? How does David approach this?

4.) Why does David believe “consumer social is interesting again”? Why was it not interesting for a while? How does that mean David is approaching the category? What does David mean when he says, “for the first time ever there is no channel to arbitrage on the internet”? Is David concerned by the state of CACs today? How much attention does David pay to CAC/LTV in the early days? What are the key signals?

Items Mentioned In Today’s Show:

David’s Fave TV Show: Survivor

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

Jason Brown is the Founder & CEO @ Tally, the startup that allows you to pay off your credit card debt faster and save money. To date, Jason has raised over $92m for Tally from the likes of Mamoon @ Kleiner, Angela @ a16z, Nikhil @ Shasta and Aileen @ Cowboy just to name a few. As for Jason, prior to Tally, he spent 5 years as the Founder and CEO Kleiner Perkins backed, Gen110. Before that Jason founded Bask, a company providing both technical support and pro-active maintenance.

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In Today’s Episode You Will Learn:

1.) How Jason came to change the world of consumer finance with Tally having spent 5 years in the solar financing sector and even a year in venture? Given his prior entrepreneurial activities, does Jason agree with Joe Fernande @ JoyMode that “serial entrepreneurship is overrated”?

2.) Does Jason believe that founders should always be raising? What is the right way to truly determine whether an investor is aligned to your mission? What should you look for in how they behave and speak? How does Jason like to build relationships with investors pre-term sheet? Is Jason concerned by the compressed fundraising timelines today?

3.) Why does Jason believe that VC funded companies are largely not over-priced? What elements of the macro-economy does Jason attribute as the reason for the high valuations today? Why does Jason believe that we should not celebrate new fundraising? Is the celebration not good for the morale of the team? What should we celebrate instead?

4.) Why does Jason believe that the target for investors is they provide no value? What are you looking to avoid? What are the core ways an investor can damage the success of a company? What can founders do to truly extract the most from their investor base? Does Jason believe one should focus on the VC partner or the firm? Why?

5.) What does Jason believe makes the best board members? What advice would Jason give to new board members on how they can truly be the best board member? Why does Jason do onboarding sessions for all new board members? What does he look to instil in this process? What behaviour at the board should not be tolerated? How should the founder communicate this to their investor?

Items Mentioned In Today’s Show:

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

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

Josh Buckley manages a $50m early-stage fund and as an angel has built a portfolio that includes the likes of Clearbit (Chairman), Rippling, Boom Supersonic, Lattice, Embark and many more incredible companies. Josh is also the Founder & Chairman @ Mino Games, the gaming studio he scaled to $20m in annual revenue and raising $40m in funding for the company.

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In Today’s Episode You Will Learn:

1.) How did Josh make his way into the world of startups at the age of just 15? How did that lead to becoming the youngest YC founder ever?

2.) What does Josh mean when he says, “the best entrepreneurs are cockroaches”? How does Josh think about capital efficiency today? Does Josh agree with Bill Gurley in stating the biggest challenge today is “the oversupply of capital”? How does Josh advise his portfolio today on raising big rounds? Capital efficiency? Burn rates?

3.) As both a fund manager and founder, what have been some of Josh’s biggest takeaways from now investing in 100+ companies as an angel? How has investing impacted Josh’s operating mentality? What are the benefits of angel investing? What are the potential dangers? What advice would Josh give to founders entering the world of angel investing?

4.) What are the biggest elements people underestimate when it comes to CAC? What have been Josh’s biggest lessons on the volatility of CAC over time? How are we seeing the platforms evolve and develop their tech and pricing? How important is channel diversity to Josh? What is balanced? What is not? What have been Josh’s biggest lessons when it comes to payback period and it changing over time?

Items Mentioned In Today’s Show:

Josh’s Fave Blog/ Newsletter: Paul Graham Blog

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

Ash Fontana is a Managing Director @ Zetta Venture Partners, the fund that invests in AI-first companies with B2B business models. As for Ash, prior to Zetta, he started the money side of AngelList, where, he launched online investing, created the first startup ‘index fund’. He also ran special projects like AngelList’s expansion into Europe and the UK. Simultaneously, Ash led syndicates and made investments in Canva, Mixmax and others. Before AngelList, Ash co-founded Topguest, a Founders Fund-backed company that built customer analytics technology and was ultimately sold in an 8 figure transaction 18 months after the company was founded.

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In Today’s Episode You Will Learn:

1.) How Ash made his way into the world of venture with AngelList and how that led to his joining Zetta today, investing exclusively in AI? What did Ash’s time working on his family farm teach him about vertically integrated businesses? What were his biggest takeaways from AngelList and working alongside Naval?

2.) What does AI-first really mean to Ash? How crucial is it for companies to have proprietary datasets today? Are data moats truly defensible and real? What are the 5 characteristics that determine the level of defensibility of a dataset? How does Ash analyse the quality of a dataset? What does Ash do to determine if they are predictive of value?

3.) We often hear the term, “system of record”, why is Ash so much more excited by the “system of intelligence”? Why is the basis of competitive advantage shifting from SaaS today as a model? How do the margin structure vastly differ when comparing AI-first companies to SaaS companies? How does that mean one should view capital efficiency?

4.) What does Ash believe drives business model quality? What are the commonalities in the business models of those that have made it big? Why does Ash believe it is difficult for incumbent companies to become AI-first? How difficult is it for incumbents to acquire smaller AI-first firms and integrate their policies and technology?

5.) Why does Ash love Howard marks and what has been his biggest learnings from studying him? How has Ash applied these learnings to his investing today? What has Ash also learned from the Italian masters of design? How has this study helped Ash as a VC? What has Ash optimised lately? What is Ash’s favourite optimisation?

Items Mentioned In Today’s Show:

Ash’s Fave Book: The Strategy of Life: Teleology and Mechanics in Nineteenth-Century German Biology

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

 

Dom Holland is the Founder & CEO @ Fast, the world’s fastest login and checkout with no more passwords, no more typing credit card details or shipping addresses. The special announcement today, Fast have just raised their seed round led by Jan Hammer @ Index, joined by Susa Ventures, Kleiner Perkins, Global Founders Capital and then angels including Nick Molnar, Founder @ Afterpay and proud to say I joined the round as an angel also. Prior to Fast, Domm was a Director @ Tap Tins, a network of smart tap-to-donate collection terminals. Domm was also the Founder & CEO @ Tow, an on-demand towing platform which transacted $50m in its first 4 years.

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In Today’s Episode You Will Learn:

1.) How Domm made his way from founding an on-demand towing company in Queensland, Australia to founding one of Silicon Valley’s hottest new startups in Fast?

2.) What did Domm do in prior companies that worked and he will do again with Fast? What did not work and he will look to avoid? Does Domm agree with Joe Fernandez @ JoyMode in saying, “serial entrepreneurship is overrated”? What advice does Domm give to first-time founders? Where do they most often make mistakes?

3.) Over the last few years we have seen incredible innovation on the merchant side of payments with Stripe and Adyen but why does Domm believe we have seen no innovation on the consumer side? Why have large internet platforms not built it themselves? Does it have to be an independent 3rd party, external to Google, Facebook, Amazon etc?

4.) With the war for talent, rising rents and a lower standard of living, why did Domm choose SF as the base for Fast? How has the move been? What have been the biggest challenges? What would Domm advise founders contemplating moving to SF? How has Domm been able to hire some big hitter valley operators so early on? How does Domm think about equity sharing and optimising ESOP plans?

5.) Jan Hammer @ Index has discussed Domm’s work mentality, so how does Domm structure his day? What does Domm do to ensure he optimises every minute? What work habits has Dom found to be most effective? What has not worked? How does Domm think about balancing speed and quality when executing today?

Items Mentioned In Today’s Show:

Dom’s Fave Productivity Tool: Superhuman

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

Rick Heitzmann is a Founder and Partner @ Firstmark Capital, one of the leading East Coast venture funds of the last decade with a portfolio including the likes of Airbnb, Pinterest, InVision, Shopify and Discord to name a few. As for Rick, he led the seed round for Pinterest and also led the deals from Firstmark in Ro, Riot Games, Draft Kings, Discord and Airbnb. Prior to founding FirstMark, Rick was an entrepreneur as a founding member at First Advantage which he helped grow and sell to First American (NYSE: FAF). Rick has been recognized by CB Insights and the New York Times as a Top 100 Venture Capitalist globally.

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In Today’s Episode You Will Learn:

1.) How Rick made his way into the world of venture and came to found one of NYC’s leading venture funds in the form of Firstmark?

2.) How did seeing the booms and bust of the macro impact Rick’s investment mentality today? With the impending crash, what 2 things does Rick advise managers need to prepare their portfolio by doing? Does Rick agree with Bill Gurley in saying, “the biggest challenge of today is the over-supply of capital”?

3.) How has Rick seen his style of investing change over the last 20 years? How does Rick think about price sensitivity today? How has that changed over the years? How has Rick seen himself change and evolve as a board member? What does Rick believe makes the best board members? What advice would Rick give to someone who has gained their first board seat?

4.) How does Rick think about the structure of the Firstmark portfolio today? How important does Rick believe it is to have temporal diversification within the portfolio? How does Rick think about optimising investment decision-making processes at Firstmark? Why does Rick believe, despite the negatives, that attribution is fundamentally important?

5.) Does Rick believe that we are in a consumer bubble today? What are the core elements that pique Rick’s interest when analysing a consumer investment today? How does Rick think about CAC’s scaling way faster and higher than anyone expected? Why does Rick believe the duopoly of FB and Google is now over? Why does Rick believe that true venture size exits can still occur in consumer?

Items Mentioned In Today’s Show:

Rick’s Fave Book: Moneyball: The Art of Winning an Unfair Game

Rick’s Most Recent Investment: Crisp

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

Ryan Denehy is the Founder & CEO @ Electric.ai, the company that provides a world-class IT solution that’s centralized, secure, and lightning-fast. To date, Ryan has raised over $37m in funding from some dear friends of the show in Rich @ GGV, Bessemer, Primary, Bowery, just to name a few. As for Ryan, he started his career at the tender age of 17 launching an action sports video production company, which was acquired just 4 years later. Ryan then spent 5 years at USA Today in numerous different roles. Following USA Today, Ryan started his second company, Swarm, acquired by Groupon just 3 years later.

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In Today’s Episode You Will Learn:

1.) How Ryan made his way into the world of startups from launching an action sports video production company at the age of 17?

2.) Having founded 2 prior companies, would Ryan agree with Joe Fernandez @ JoyMode in saying that “serial entrepreneurship is overrated”? What did he do right in the first 2 companies that he would look to do again? What did not work that he is avoiding? Where does Ryan most often see first-time founders make mistakes scaling?

3.) How does Ryan think about and assess wartime leadership? What is the right leadership style and approach to battle through the really tough times? Ryan’s investors talk of his speed of execution, how does Ryan balance the speed with the quality when it comes to execution? How has Ryan seen both his role and the way in which he executes it change with the scale of the company and of himself?

4.) How does Ryan thnk about and assess forward planning when it comes to recruitment? How should this recruitment planning align to fundraising? Why must it start before the fundraise? How does Ryan think about levelling up individuals internally vs hiring external candidates? How does Ryan think about and present internal expectation setting?

Items Mentioned In Today’s Show:

Ryan’s Fave Book: Barbarians At The Gate

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.

Lisa Edgar is a Managing Director @ Top Tier Capital Partners, one of the leading venture fund of funds over the last decade. Included in their stellar fund portfolio is the likes of Index, Initialized, True Ventures, a16z and Boldstart, to name a few. Prior to Top Tier, Lisa was part of the asset management team at WR Hambrecht + Co focusing on new and emerging private equity funds. Before that, Lisa spent ten years at Horsley Bridge.

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In Today’s Episode You Will Learn:

1.) How did Lisa make her way into the world of investing in funds and how did that lead to her becoming Managing Director at one of the leaders, Top Tier?

2.) Lisa has seen the boom and bust of the macroeconomy twice now, how has that impacted her mindset today when investing in funds? What have been the most prominent changes in the venture ecosystem that Lisa has seen over the last 20 years? What changes have been good? What changes have been bad?

3.) What is the best way to get in the room with LPs? Does it have to be through warm intro? What are the signs for the GP that that first meeting went well? If an LP does not respond to emails, does that mean they don’t want to do it? How does Lisa and Top Tier structure the investment decision-making process? How does that differ when re-investing in existing managers? Is it worth it for first-time funds to pitch institutions for fund 1 when they know they will not invest in the fund?

4.) How does Lisa think about GP commits today? How does Lisa look at what is reasonable and what is required? Is it individual and context-based? How does Lisa feel about different carry structures? Are kickers when past a certain return profile amenable to LPs?

5.) Lisa has seen some of the best emerging managers in the US over the last decade, what learnings does she have from them in terms of what separates the good from the great? How do they think about partnership dynamics? How do they think about firm culture? How do they think about generational transition?

Items Mentioned In Today’s Show:

Lisa’s Fave Book: From the Mixed-Up Files of Mrs. Basil E. Frankweiler

Lisa’s Most Recent Investment: Boldstart Ventures

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

Vlad Magdalin is the Founder & CEO @ Webflow, the startup that allows you to build better business websites, faster, without coding. To date, Vlad has raised over $73m with Webflow from some dear friends of the show including Accel, Ron @ Rainfall, Brianne @ Work Life, Benjamin Ling and Y Combinator to name a few. Prior to founding Webflow, Vlad was a Senior Software Engineer @ Intuit. Before Intuit, Vlad co-founded Chatterfox, a web application allowing people to stay in touch with groups of friends, family, or co-workers.

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In Today’s Episode You Will Learn:

1.) How Vlad made his way into the world of startups? How did the original idea to democratise the world of design and site creation with Webflow come about?

2.) Webflow has had an unorthodox funding path with their recent $73m Series A, how was it for Vlad raising the seed round with Webflow? What lessons did he learn from that raise? Why did they drive to be breakeven so much earlier than others might? Why did Vlad believe now was the right time to go big and raise the Series A?

3.) Vlad chose to partner with Accel, what advice does Vlad give to founders in determining which funding partner to choose? What makes for the best VC <> founder relationships? What is the optimal way to build those relationships? Where does Vlad believe that VCs can strategically move the needle? Where do many think VCs can really help but they most often cannot?

4.) What have been Vlads biggest lessons when it comes to successful board management? What advice would Vlad give Harry when it comes to joining boards as new board member? What does Vlad mean when he says, the best board members come to the board with the mindset of “servant leadership”? How do they show that in their actions? How can investors create an environment of trust at the board?

5.) Vlad AMA: Why does Vlad believe that it is a distraction for founders to be angel investing alongside their role as a founder? How does he believe this creates a wedge between them and the team? How has having kids impacted how he thinks about operating today? What have been the big takeaways from fatherhood?

Items Mentioned In Today’s Show:

Vlad’s Fave Book: Leaders Eat Last: Why Some Teams Pull Together and Others Don’t

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

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

Ben Horowitz is a Co-Founder and General Partner at Andreessen Horowitz, one of the leading and most prestigious venture firms of the last decade with a portfolio including the likes of Facebook, Github, Slack, Lyft, Coinbase and many more incredible companies. Ben is also the author of the New York Times bestseller, The Hard Thing About Hard Things, and the upcoming Harper Business book, What You Do Is Who You Are, available October 29. Prior to a16z, Ben was Co-Founder and CEO of Opsware, acquired by Hewlett-Packard for $1.6 billion in 2007. Previously, Ben ran several product divisions at Netscape Communications, including the widely acclaimed Directory and Security product line.

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In Today’s Episode You Will Learn:

1.) How did Ben make his way into the world of venture having previously co-founded Opsware? What was the original thinking for a16z? How did seeing the booms and busts of the market as an operator, impact how Ben thinks about investing today?

2.) In the book Ben says, “If soldiers trust the general, communication will be vastly more efficient”. What have been Ben’s biggest lessons on how to create an environment of trust quickly? As a board member, how does Ben create an environment of trust for the founder? What is Ben’s advice to Harry having just gained his first board seat last year?

3.) Ben has said before of the importance of creating “shocking rules”. What are the rules for creating these shocking rules? What are the best rules composed of? Given their shocking nature, how does one instil them in the organisation? What does Ben think is the most shocking rule he has implemented at a16z?

4.) What does ben believe that founders can take away from the rituals of the Samurai? Why does Ben believe that “meditating on company downfalls will enable you to build your culture the right way”. Why is the negativity so helpful in forming the right culture? How does ben advise founders when their company is struggling, the team knows it and morale is low? What happened at Okta? How did they turn the culture and business around?

5.) Ben has previously spoken about bringing in external leadership from the cultures you want to master. How does one know when is the right time to bring in this external influence? What can we learn from observing Google Cloud’s strategy? How does one retain the old culture but augment it with the new? What were some of Ben’s biggest hiring lessons when operating? How does Ben get employees to “feel a sense of urgency”, when a change needs to occur?

Items Mentioned In Today’s Show:

Ben’s Fave Book: The Black Jacobins: Toussaint L’ouverture and the San Domingo Revolution

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

Steve Huffman is the Co-Founder & CEO @ Reddit, home to thousands of communities, endless conversation, and authentic human connection. To date, Reddit has raised over $550m in funding from some of the world’s leading investors including Sequoia Capital, Marc Andreesen, Peter Thiel, Ron Conway, Sam Altman, Josh Kushner, Alfred Lin and Tencent, just to name a few. Steve started his career at Y Combinator as one of their first alumni back in 2005. At YC, Steve co-founded Reddit with Alexis Ohanian, which they sold in 2006 to Conde Naste Publications. In 2010, Steve co-founded Hipmunk, making business travel seamless and easy. Then in 2015, Steve re-joined Reddit as their CEO.

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In Today’s Episode You Will Learn:

1.) How Steve made his way into the world of startups and came to be one of the very first ever entrants in the now hailed Y Combinator? How did that lead to the founding of Reddit? Why did Steve return to Reddit, the company he founded, in 2015?

2.) What were Steve’s biggest lessons from his journey with Hipmunk when it came to product feedback and iteration? How does Steve assess people’s reliance on data today to drive product decisions? Why does he believe 3 criteria must be considered? What are the other two? What time did Steve see the confidence of his own intuition really increase?

3.) How does Steve think about stress management today? What was he like when he was younger in his relationship to stress? What did he actively do to change his relationship to stress? How has Steve seen himself change and develop as a CEO? What have been the inflection points? What has he struggled and also made mistakes in the journey?

4.) What have been Steve’s biggest lessons when it comes to hiring truly A* talent at scale? What are the commonalities in the very best hires Steve has made? In the cases of it not working, what does Steve advise founders on the right way to let someone go? How does one do it with efficiency and compassion?

5.) Why does Steve believe that in dense cities, self-driving cars will not be that useful? How does Steve envisage the future of consumer transportation? What does he believe are the alternatives to self-driving cars? How does Steve see the future for the unbundling of social networks? Will they be unbundled into specific communities? How will this look?

Items Mentioned In Today’s Show:

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

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.

Arif Janmohamed 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. Some of Arif’s most notable companies that he has led or been involved with for LSVP includel; TripActions, Blend, Nutanix, AppZen, MoveWorks and more. Prior to Lightspeed, Arif worked in the corporate business development team @ Cisco as part of transaction leadership and execution on a number of deals including WebEx. Before WebEx, Arif founded WVP Ventures, a student-run venture capital organization.

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In Today’s Episode You Will Learn:

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

2.) We are seeing pricing hit 100x ARR multiples, does Arif believe we are seeing enterprise investing as past it’s peak? Are we seeing late-cycle momentum investing? Would Arif agree with matt Harris, “Series A pricing does not matter anymore?” How does Arif assess his own price sensitivity today? How has it changed over time?

3.) Why does Arif believe that market risk is the most dangerous risk to underwrite as a VC? How does Arif think about and assess market timing? What has changed over the last few years to unlock such quantums of capital into the enterprise market? With the acquisitions of Duo, Mulesoft, Qualtrics, will we have a next-gen incumbent set or will it be an environment of existing incumbent consolidation?

4.) What does Arif specifically believe founders need to get right when it comes to company design, in order to scale to a $5-10Bn market leader? In terms of the go-to-market, who does Arif think has nailed it most recently? Why? How does Arif test for a founding team’s ability to execute on go-to-market when meeting them early on?

Items Mentioned In Today’s Show:

Arif’s Fave Book: Stumbling on Happiness, How Not To Die: Discover the foods scientifically proven to prevent and reverse disease

Arif’s Most Recent Investment: TripActions

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

Roy Bahat is the Head of Bloomberg Beta, one of the leading early-stage funds in the valley and NYC with a portfolio that includes the likes of Flexport, Kobalt, Textio, Rigetti Computing and more incredible companies. Prior to Bloomberg Beta, Roy was the Co-Founder & Chairman @ Ouya, the company that created a new kind of games console and raised over $33m from the likes of Kleiner, Alibaba and even $8.6m on Kickstarter. Before the world of startups, Roy held numerous incredible and fascinating roles including Director of International Strategy at New York’s bid for the 2012 Olympic Games and also was a Senior Policy Director in the Office of the May of New York City.

Brianne Kimmel is the Founder and Managing Partner @ Work Life Ventures, a very new firm focused on the future of work backed by some of the best in the valley including Marc Andreesen, Chris Dixon, Zoom’s Eric Yuan, InVision’s Clark Valberg and then dear friends of the show, Alexis Ohanian, Garry Tan and Matt Mazzeo. To date, Brianne has invested in the likes of Webflow, Tandem, Lunchclub and Girlboss to name a few. Prior to starting Work Life, Brianne spent 2 years at Zendesk on their GTM strategy; building Zendesk for startups, ultimately representing 3,000 startups and 250 accelerators. From 2013-2017 Brianne also taught over 5,000 students at General Assembly all things user acquisition and growth marketing.

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In Today’s Episode You Will Learn:

1.) How Brianne made her way into the world of startups and SaaS, how that led to her angel investing and what was that a-ha moment for the founding of Work Life? Why did Brianne choose to structure Work Life as a holding company?

2.) With the fund, how does Brianne think about portfolio construction? What is the right check size for her? Why does Brianne think we are seeing more angel funds than ever today? Why are we seeing so many celebrity names on the cap tables of great companies? How does Brianne think about scout programs? What impact have they had? Why is Brianne against founders actively angel investing?

3.) What does Brianne advise founders on how to structure a high-signal round? What are the two types of angels that exist in the world today? What can founders do to keep their angels actively engaged? How have what founders expect from their angels changed over the last few years? How does one measure the true value of an angel?

4.) Does Brianne agree with Semil Shah, we are seeing “founders vote with their feet and bypass seed funds for multi-stage funds”? How does Brianne advise founders when choosing between a boutique seed firm and a large multi-stage firm? What does Brianne believe are the pros and cons of taking multi-stage money at seed?

Items Mentioned In Today’s Show:

Brianne’s Most Recent Investment: Pace

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

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

Rachel Carlson is the Co-Founder and CEO @ Guild Education, the leader in education benefits offering the single most scalable solution for preparing the workforce of today for the jobs of tomorrow. To date, Rachel has raised over $71m in funding with Guild from some of the best in venture with the likes of Michael Dearing @ Harrison Metal, Wes Chan @ Felicis, Byron Deeter @ Bessemer, Aileen @ Cowboy Ventures and Scott Raney @ Redpoint, all backing Guild. As for Rachel, prior to Guild, Rachel was the Founder of Student Blueprint, providing students with academic and career planning tools. 

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In Today’s Episode You Will Learn:

1.) How Rachel made her way into the world of startups having started her career in politics and how insights gleaned from politics formed the idea for Guild Education?

2.) Why does Rachel believe that ambitious Mums are the most under-utilized asset in the economy? What are the biggest misconceptions people have about hiring and working with Mums? How can founders really implement practically facilities, tools and an environment where one can be both ambitious personally and professionally?

3.) Before the show, Byron Deeter @ Bessemer said, “Rachel has been among the best at recruiting star execs across their portfolio”. What have been Rachel’s biggest lessons when it comes to hiring the very best talent? Where do most go wrong? How has her hiring style changed over the years? What are Rachel’s favourite questions to ask candidates?

4.) Why does Rachel believe that mission and margin are tightly integrated? How did Rachel acquire Walmart as one of their first clients? What are the positives and negatives of having a client so huge, so early? What advice would Rachel have for other early-stage companies when they have such behemoths as clients in the early days?

5.) Why did Rachel make the move from SF to Colorado? What did Rachel strategically do to ensure the chances of success were higher? How does Rachel feel about keeping leadership teams in SF and then the rest elsewhere? How did the move impact their ability to hire the best talent? How did their move impact their ability to access the best capital? Between customers, capital and employees, who is it most important to be near?

Items Mentioned In Today’s Show:

Rachel’s Fave Book: To the End of June: The Intimate Life of American Foster Care, Where The Crawdads Sing

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.

John Fein is the Founder and Managing Partner @ Firebrand Ventures, one of the leading early-stage funds in the midwest with a portfolio including the likes of ScaleFactor, Replica, Dwolla and more fantastic companies. As for John, prior to founding Firebrand, he was the Managing Director of Techstars based in Kansas City and before that spent close to 9 years at OptumRx where he managed multi-billion dollar large-scale programs for the $15B pharmacy benefit manager division of UnitedHealth Group.

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In Today’s Episode You Will Learn:

1.) How John made his way into the world of venture from scaling a pharmaceuticals business to almost $2Bn in revenue and how that led to founding Firebrand?

2.) What was it like for John raising the first fund for Firebrand with no existing network of LPs or high-net-worth individuals? How did John approach his closing strategy? How did he decide the amount of money to raise for the fund? How did Techstars Founder, David Cohen change and impact his thinking here? Was John surprised by how long the fund took to raise?

3.) What does John know now that he wishes he had known at the beginning of the fundraise for the first fund? Does it ever get easier? What does John believe are the biggest challenges in managing your own fund? What does he do to mitigate them? How does running your own fund differ from operating in a venture partnership?

4.) “Seed” is so confused in meaning today so what does “seed stage” really mean to John? Does John agree with Harry that we are seeing the eradication of the pre-seed stage? Where does John believe is the ideal insertion point? Does John believe that ownership can be built over time? How does John think about reserve allocation?

5.) How does John think about the relationship-building process with founders? Is John worried by the compressed fundraising timelines we are seeing today? What can investors do to build trust with founders quickly? What signs impress John in the early days of getting to know the founder? What are some common red flags for John?

Items Mentioned In Today’s Show:

John’s Fave Book: Reboot: Leadership and the Art of Growing Up by Jerry Colonna

John’s Most Recent Investment: The Minte

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

Jason Boehmig is the Founder & CEO @ Ironclad, the startup that provides powerful legal contracting for modern legal teams. To date, Jason has raised over $84m with Ironclad from some of the best in the business including Sequoia, Accel, Greylock, Emergence, IA Ventures, Semil Shah’s Haystack and Ali Rowghani who led their recent $50m Series C from Y Combinator Continuity Fund. As for Jason, prior to founding Ironclad, he was both a corporate attorney with Fenwick & West and then also an adjunct professor of Law at the University of Notre Dame.

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In Today’s Episode You Will Learn:

1.) How Jason left the world of law and made his way into the world of startups and came to be founder of one of Silicon Valley’s hottest startups, Ironclad? How did Jason’s experience at Lehmann Brothers impact his operating mentality today as a founder? What were his big lessons on personal conviction from seeing Lehmann unravel?

2.) Ironclad is famed for their customer discovery process, so how does Jason think about product development in the early days? What core questions does Jason ask to understand customer needs and desires? How does Jason determine what to implement and what to prioritise? How does Jason think about the balance between data vs gut in product decision-making? What have been his lessons here?

3.) When it comes to hiring, how does Jason approach keeping top of funnel constantly full? Why does Jason believe that when hiring, “when there is doubt, there is no doubt”? What are the common reasons that Jason does not hire a potentially strong candidate? How does Jason determine between a stretch VP and a stretch too far?

4.) How does Jason think about relationship building with VCs? Where do so many founders make mistakes in this process? What advice does Jason have on successfully negotiating with VCs? What works? What does not? What value-add has Jason realised VCs really can and do provide? Where is there a suggestion that they do but rarely do?

Items Mentioned In Today’s Show:

Jason’s Fave Book: Meditations by Marcus Aurelius

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.

Brad Feld is Managing Director @ Foundry Group, one of the most successful venture firms of the last decade with a portfolio that includes the likes of Zynga, Fitbit, SendGrid and many more incredible companies. Prior to co-founding Foundry Group, he co-founded Mobius Venture Capital and, prior to that, founded Intensity Ventures. Brad is also a co-founder of Techstars, the worldwide network of entrepreneurs in 150 countries and 300,000 alumni. Brad is also the co-author of the incredible, Venture Deals, for your chance to win a signed copy email venturedeals@foundrygroup.com with the code “First Episode”.

 

Julia Enthoven is the Founder & CEO @ Kapwing, the startup that provides a new, collaborative platform for creating images, videos, and GIFs. To date they have raised $13m from some dear friends of the show including Saar Guur @ CRV, Mamoon Hamid @ Kleiner Perkins, Niv Dror @ Shrug and Nikhil Basu Trivedi @ Shasta. Prior to founding Kapwing, Julia was an Associate Product Manager @ Google where she worked on everything from image search to sign up workflows.

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In Today’s Episode You Will Learn:

1.) How Julia made her way into the world of startups and came to found the future of content editing with Kapwing?

2.) What does Julia believe are the 4 benefits to building a website over an app today? How does this change your development cadence and speed of product iteration? How does this change your economics and margin structure? Where does Julia see many founders making mistakes here?

3.) Why does Julia believe that marketing innovation is as important as product innovation? Kapwing is now at 1m users per month, what has been Julia’s biggest lessons in scaling a customer base to this size with very little spend? How does Julia think about marketing channel mortality rate? How should founders approach this?

4.) Why did Julia decide it was better to bootstrap than straight away trying to raise VC dollars? What were the benefits of this? Was it the right decision? What was the turning point when Julia realised was the moment to raise external funding? How did her mindset change as a result of the funding? How does bootstrap life compare to VC funded startup?

5.) How is Julia finding the personal scaling journey from PM to CEO? What have been some of the biggest challenges? What has she done to overcome them? What advice would Julia have for other newly minted CEOs? What have been some of Julia’s biggest lessons in what it takes to hire the very best talent early?

Items Mentioned In Today’s Show:

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

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

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

Matt Harris 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 Matt, he specialises in financial technology and services and has led investments in the likes of Acorns, OpenFin, SigFig, Ribbon and Billtrust. Prior to joining BCV, Matt founded Village Ventures, which he ran for 12 years and where he focused on early-stage fintech investing. Before Village Matt actually started his investing career Bain Capital private equity in 1995.

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In Today’s Episode You Will Learn:

1.) How Matt made his way into the world of venture from private equity and what led him to specialise as he has done in the world of fintech?

2.) How did seeing the boom and bust of the dot com impact Matt’s investing mindset today? How has Matt’s fear of the cyclicality of markets actually lost him a lot of money in the past? What has that taught Matt on trying to time markets? What were the main takeaways for Matt from running his own firm? How does it differ to a partnership?

3.) Why does Matt believe we are seeing late-cycle momentum investing today? What is the evidence to suggest this? How does Matt think about the right cadence to invest through market cycles? What does Matt mean when he says, “Series A valuation does not matter anymore”? Why? How does Matt assess his own price sensitivity today?

4.) Why does Matt believe that investing in improbable ideas is a good strategy? What does this mean the internal investment decision-making process looks like at Bain? Why is full consensus sometimes a concern? How does Matt approach market sizing? Why does it not matter at Series A? When does it really start to matter?

5.) Matt has said before that “backing sociopaths can work”. What did he mean by this? What founder type does Matt most like to back? Does one have to manage the relationship with them very differently to other founder types? What are the acceptable risks vs unacceptable risks with this founder type?

Items Mentioned In Today’s Show:

Matt’s Fave Book: The Third Plate: Field Notes on the Future of Food

Matt’s Most Recent Investment: Finix

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

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

Immad Akhund is the Founder & CEO @ Mercury, the startup that makes bank accounts that help tech companies scale. To date, Immad has raised funding from some of the best in the business including a16z and CRV on the fund side and then individuals including Elad Gil, Airtable’s Howie Liu, Plaid’s Zach Perret, Naval Ravikant, Justin Kan and OpenDoor’s Eric Wu. Prior to founding Mercury, Immad held enjoyed numerous different roles including being a part-time partner at Y Combinator and then also founding HeyZap, building developer tools for mobile game developers, ultimately acquired in 2016.

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In Today’s Episode You Will Learn:

1.) How Immad made his way from studying in the UK to being a YC Partner in 2017 and building one of the valley’s hottest startups today in the form of Mercury?

2.) What does Immad want to do differently this time around with Mercury vs his time with HeyZap? What 1-2 mistakes that he made the first time round is Immad looking to avoid? How does being a serial founder impact one’s ability to acquire the best talent? What does Immad think is harder the second time around? How has becoming a parent changed the way that Immad thinks about founding and building companies?

3.) How does Immad approach the process of picking the idea? What was the specific process with Mercury, step by step? Why does Immad believe it is an advantage to not have a background or prior career in the space you are looking to innovate in? What advice does Immad have for founders looking to move into highly regulated industries?

4.) How does Immad approach and assess the element of competition? What is the right way for founders to present competition when pitching to investors? Why is a 2×2 matrix the wrong approach? What does Immad advise portfolio founders he has invested in with regards to competition and the landscape in front of them?

5.) What have been some of Immad’s biggest learnings from making over 120 angel investments? How has angel investing speciifcally helped certain parts of how he thinks about operating and being a founder today? What advice does Immad give with regards to investor updates? What makes the best ones? What makes the worst? How often should they be?

Items Mentioned In Today’s Show:

Immad’s Fave Book: The Accidental Superpower: The Next Generation of American Preeminence and the Coming Global Disaster

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

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

Semil Shah is the Founder & General Partner @ Haystack, one of the valley’s leading seed funds of the last 5 years with a portfolio including the likes of Instacart, DoorDash, Carta, OpenDoor, Hashicorp and more $Bn companies. Alongside his role at Haystack, Semil is also a Venture Partner @ Lightspeed Venture Partners. Prior to founding Swell, Semil was on the operating side as an early advisor and employee at Concept.io (Swell), acquired by Apple in August 2014.

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In Today’s Episode You Will Learn:

1.) How did Semil make his way into the world of venture from his start writing about startups and financing rounds? How did that also lead to his role as Venture Partner @ Lightspeed today?

2.) What does Semil mean when he says, “the most talented founders are bypassing seed firms and seed rounds”? How does this mean that seed funds need to respond? For founders, what are the pros and cons of taking a multi-stage fund at seed? Will they really get GP time with such a small check? How should they also think about potential signalling risk?

3.) Does Semil share Harry’s concern with regards to pricing today? What do multi-stage funds investing at seed do to pricing? Why is staying disciplined on price the biggest challenge for Semil? How does Semil assess his own price sensitivity and when to stretch? Does Semil believe that ownership is built on first check or overtime?

4.) How does the strategy for Semil change moving from a $25m fund to a $50m fund? Why does Semil think that temporal diversification is such an important element to bake into a portfolio? What are the benefits? How does Semil think about effective reserve allocation today? What does that investment decision-making process look like the 2nd time?

5.) How has Semil seen the ecosystem for VC fundraises change over the last 5 years? What would Semil like to change about the ecosystem of LPs? What blanket rule does Semil believe that LPs should introduce for new managers to ensure discipline? For Semil, how did the fundraise differ for the latest $50m fund compared to the prior $25m fund?

Items Mentioned In Today’s Show:

Semil’s Fave Book: Reboot by Jerry Colonna

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

Alex MacCaw is the Founder & CEO @ Clearbit, the marketing data engine for all of your customer interactions, from customer understanding to prospect identification to personalising every sales and marketing interaction. To date, Alex has raised $17m in financing from some incredible people including Geoff Lewis @ Bedrock, Ash Fontana @ Zetta Venture Partners, First Round Capital, Battery Ventures and then former guest Ilya Sukhar, Naval Ravikant and Josh Buckley. Prior to founding Clearbit, Alex spent time in the engineering teams at both Twitter and Stripe.

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In Today’s Episode You Will Learn:

1.) How Alex made his way from the UK to becoming one of the hottest founders in the valley with the rise of Clearbit? What does Alex believe is more important mission and vision or organisational discipline? What does Alex mean when he says he started the company as a “vehicle for growth thinking and self-actualisation”?

2.) What did Alex mean when he said, “when you hit product-market-fit, it is time to move into company making”? What does company making mean to Alex? What would Alex like to fundamentally change about the way we manage companies today? When is the right time to make this transition? What needs to be in place to do it successfully?

3.) What does Alex mean when he says, “The 6 Pillars Behind Clearbit”? What elements does Alex think the team should not have full transparency on? How does Alex approach transparency when it comes to fundraising and M&A opportunities? What have been some of Alex’s biggest learnings on both delivering and absorbing feedback? What can one do to create an environment of radical candor and rich feedback?

4.) Why does Alex believe that health has to be the #1 priority for every founder? What does that look like in practice? What can one provide the team to encourage this? How does Alex respond to those that might say, “fine but we cannot afford it”? How does Alex suggest there are 3 ways you can become more self-aware as an individual?

5.) What advice does Alex give to founders on successfully negotiating with investors? What value has Alex found that VCs really do bring? What does Alex optimise for when selecting his investor base? What value do most think that VCs bring but they actually do not? When does Alex think one should establish a board? Why does Alex think your board should only have operators and no investors on it?

Items Mentioned In Today’s Show:

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

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.

Ilya Sukhar is a General Partner @ Matrix Partners, the firm steeped in 40 years of history with over $4Bn invested enjoying 110 acquisitions and 65 IPOs. As for Ilya, at Matrix he has led deals in the likes of FiveTran, Flock Safety, Slab and Height just to name a few. Prior to Matrix, Ilya was a part-time investing partner @ Y Combinator and before that was Head of Developer Products at Facebook. His time at Facebook came about as a result of his former company, Parse, being acquired by them for close to $100m in April 2013. If that was not enough, Ilya also has one of the best angel tracks in the business with a portfolio including the likes of former guest Scale, Checkr, Algolia, Airtable, Gitlab the list goes on.

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In Today’s Episode You Will Learn:

1.) How Ilya made his way into the world of technology and startups having moved to SF from the Soviet Union? How did his growing up in the Soviet Union and moving to the US shape his thinking, operating and investing mentality today?

2.) How did Ilya’s mindset change with the shift from angel investing to institutional investing? How does Ilya assess how his operating experience has impacted the way he works and engages with founders today? What are the pros? What are the cons? Why does Ilya believe the engineering CEO is so crucial?

3.) How does Ilya feel the seed ecosystem is serving startups today? What are the core ways that Ilya believes it is not optimised? How does Ila think about advising founders on the right amount to raise and the appropriate amount of runway? How does Ilya feel on the subject of bridge rounds? How does Ilya approach price and price sensitivity? What have been his learnings on price from observing his angel portfolio?

4.) Why does Ilya believe that “referencing is one of the most important skills for founders and investors”? How should founders structure their referencing? Who should they speak to? How many people is an appropriate dataset? What are the core questions to ask? How can references lead one astray? What must you watch out for?

5.) How has becoming a father changed Ilya’s investing mentality today? How has it affected how he selects the projects he wishes to work on? How has it changed his relationship to time and productivity? Why in many ways does Ilya wish he had had kids earlier?

Items Mentioned In Today’s Show:

Ilya’s Fave Book: When Genius Failed: The Rise and Fall of Long Term Capital Management, The Stranger

Ilya’s Most Recent Investment: FiveTran

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

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

Alex Wang is the Founder & CEO @ Scale, the data platform for AI providing high-quality training and validation data for AI applications. To date, they have raised over $123m in financing from some of the best investors in the business including Daniel Levine @ Accel, Founders Fund, Index Ventures, Thrive, Spark and Coatue and then also some of the world’s best operators and founders of Dropbox, Instagram, Quora, Github and Twitch to name a few. Prior to founding Scale, Alexandr was a Tech Lead at Quora, directly responsible for all speed projects and before that a software engineer at Addepar responsible for building and maintaining financial models.

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In Today’s Episode You Will Learn:

1.) How Alex made his way from growing up in Los Alamos to being one of the hottest founders in the valley with Scale’s new round giving them a unicorn valuation? How did growing up outside the ether of the valley shape Alex’s operating mindset today?

2.) Why does Alex believe that AI is under-hyped relative to the state of technology today? Would Alex agree that most projects claiming to be AI are merely rebrandings from actuarial science, data science etc etc? What questions does Alex ask to determine true AI or BS?

3.) How does Alex think about how AI can deal better with ambiguity of data? What other core areas would Alex like to see meaningful step-function improvements in? How does Alex think about the value of data-set size? How does he think about the utility value of data reducing with every incremental data point? How does Alex think about the rise of synthetic data? How does this change the landscape?

4.) What are Alex’s biggest lessons on what it takes to hire incredible people before you are a hot company? How does Alex determine whether someone has the right risk profile and desire to work in a startup? What questions reveal that? Where does Alex believe that many go wrong in the early days of hiring? What would he do differently now?

5.) For the $100m Series C, how did the round come together? What did the process look like? How did this round compare to the other rounds? How does Alex think about and approach the element of investor selection? How can founders build relationships with investors in these hyper-compressed fundraising timelines? What have been Alex’s biggest lessons when it comes to CEO growth and then also board management?

Items Mentioned In Today’s Show:

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

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.

 

Jana Messerschmidt is an investor @ Lightspeed Venture Partners, one of the best performing funds of the last decade with a portfolio including Snapchat, Mulesoft, Max Levchin’s Affirm, Cameo, StitchFix and many many more incredible companies. Prior to LSVP, Jana co-founded #Angels in 2015, a first of its kind investment collective specifically designed to get more women on the cap tables of successful companies. Her portfolio includes the likes of Carta, Lambda School, Bird, Forward and Cameo to name a few. In addition to #Angels, Jana spent 6 years at Twitter as VP of Global Business Development and Platform where she led the 150+ person organization responsible for Twitter’s global strategic partnerships. Finally, before Twitter, Jana spent 2 years at Netflix as Director of Business Development. 

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In Today’s Episode You Will Learn:

1.) How Jana made her way from the worlds of Twitter and Netflix to founding #Angels and becoming an angel to today, investing on the front lines with Lightspeed?

2.) What were some of Jana’s biggest takeaways from her time with Netflix? How did that experience impact her operating mentality today? How can leaders determine the true quality of their team and their conviction in them? What is “the leaver test”? What does Netflix do internally to drive such high performance? What does Jana mean when she says, “leaders have to provide context, not control”?

3.) Does Jana believe that founders should “always be raising”? What is the right way for founders to approach OKR setting with regards to requirements for the next round? When should this OKR discussion for the next round take place? Who should be involved? How can founders get potential investors to do the work upfront and determine interest?

4.) In terms of metrics for the Series A, they depend based on the vertical and business model but what is required, metric wise, to raise a Series A in:

1. A D2C brand? What revenue levels would be expected? What growth levels would be expected?
2. A consumer subscription business? What level of churn is acceptable? What does Jana see as a good CAC/LTV?
3. Why does Jana believe that you cannot grow your business on ad spend perpetuity? How does Jana think about the cost of advertising today? What have been her biggest lessons when it comes to how CAC changes over time?

5.) What tips and advice does Jana give to founders to allow them to enter fundraising negotiations with leverage? What can founders do to gain leverage if their numbers are not in place? What does Jana think should be some of the biggest considerations for founders when it comes to their cap table?

6.) How does Jana think that founders can put their cap table to work in the most effective way? Is there a way to stress their suggested “value-add” prior to their investment? What can be done to actively improve the lack of women and underrepresented minorities on cap tables? What would Jana like to see change here?

Items Mentioned In Today’s Show:

Jana’s Fave Book: Elad Gil’s High Growth Handbook, Dark Money

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

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

 

Clark Valberg is the Founder & CEO @ InVision, the digital product design platform powering the world’s best user experiences. To date, Clark has raised over $350m with InVision from some of the world-leading investors including Iconiq, Spark Capital, Accel, Battery Ventures, Tiger Global, FirstMark and even Atlassian. Prior to founding InVision, Clark spent 8 years as the Co-Founder of Epicenter Consulting, a leading web application design business. If that was not enough, Clark is also a leading angel with a portfolio including Algolia, Voiceflow, Unsplash and BentoBox, just to name a few.

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In Today’s Episode You Will Learn:

1.) How Clark made his way from running a successful design agency to fundamentally changing the way designers design products and consumer experience them through InVision?

2.) Why does Clark believe that all aspiring entrepreneurs questions have a false premise? What is the fundamental false premise of entrepreneurship? How does Clark assess the importance of vision and mission over alternate elements? What advice does Clark give to the many aspiring entrepreneurs that ask for his advice?

3.) How does Clark think about market timing today as an entrepreneur? How does Clark think investors should approach and think about market timing? How does Clark look to measure impact not just size of the market? How has angel investing changed Clark’s operating mentality as an entrepreneur with InVision?

3.) Why does Clark believe that enlightenment is a daily task? What does Clark do to fundamentally make himself present enough to appreciate those inflection points and moments of enlightenment? How can everyone use note-taking to gain this level of self-consciousness? How are the notes structured? What routine needs to be built around them?

4.) How does Clark think about taking the time to appreciate the milestones that are achieved? Why do we have to make celebrating a ritual? What can be done to ensure these moments of company and personal growth are recognised? What have been Clark’s biggest moments of realisation on this theme?

5.) With InVision being an almost fully remote team, what have been Clark’s biggest breakthroughs in making it work so well with his marriage and his family? What are “date days”? How does Clark use them to ensure the right balance of work and romance? What has Clark found to be the weirdest thing of operating a 900-person remote firm?

Items Mentioned In Today’s Show:

Clark’s Fave Book: Positioning: The Battle for Your Mind: The Battle for Your Mind

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

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

Mike Vernal is a General 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 Mike he has led and sits on the board of Citizen, rideOS, Rockset, Threads and Houseparty (acquired by Epic). Prior to venture, Mike spent 8 years at Facebook as VP of Product & Engineering leading multiple different teams including Search, Commerce, Profile, and Developer product groups. Prior to Facebook Mike spent 4 years at Microsoft as a PM lead in Microsoft’s Developer Division.

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In Today’s Episode You Will Learn:

1.) How Mike made the move from VP of Product & Engineering at Facebook to General Partner at the world-famous, Sequoia Capital? What were Mike’s biggest takeaways from his 8 years at FB seeing the hyper-growth first hand?

2.) Mike has previously said that he has struggled in the past when it comes to “overthinking investments”. What does he mean by this? How does it play out in reality? How does Mike balance between trusting his gut and relying on the data? How does Mike think venture partnerships should participate in this balancing act?

3.) Why does Mike believe decision-making in venture to be fundamentally different to decision-making in operations? How do they compare? How does the decision-making process and approach change as a result of this contrast? How does Mike think about his own time allocation now in venture? What is the most challenging element?

4.) How does Mike evaluate the proliferated SaaS landscape today? Why does Mike believe that the notion of SaaS as a construct will fade over the coming years? What does Mike believe is the reasoning for SaaS apps becoming more and more niche? What problem does that pose for VC? Will we enter a period of consolidation in SaaS? What size do the incumbents have to be to really engage in the M&A process moving forward?

5.) Why does Mike struggle to see the strength of data moats? What are the major downfalls associated with the argument of their strength? At what point is the asymptotic point of the utility value of the data for models today and how does that change over the coming years? What does Mike instead see as durable and sustainable moats?

Items Mentioned In Today’s Show:

Mike’s Fave Book: One Hundred Years of Solitude 

Mike’s Most Recent Investment: Verkada 

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.

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.

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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.

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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.

---

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.