The Twenty Minute VC

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

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In Today’s Episode You Will Learn:

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

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

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

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

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

Items Mentioned In Today’s Show:

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

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

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

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

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In Today’s Episode You Will Learn:

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

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

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

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

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

Items Mentioned In Today’s Show:

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

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

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

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

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In Today’s Episode You Will Learn:

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

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

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

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

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

Items Mentioned In Today’s Show:

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

David’s Most Recent Investment: Ordermark

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

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

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

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In Today’s Episode You Will Learn:

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

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

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

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

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

Items Mentioned In Today’s Show:

Anjney’s Fave Book: Rainbows End

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

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

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

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In Today’s Episode You Will Learn:

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

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

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

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

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

Items Mentioned In Today’s Show:

Sam’s Fave Book: Lessons of History

Sam’s Most Recent Investment: Fetcher.ai

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

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

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

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In Today’s Episode You Will Learn:

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

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

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

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

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

Items Mentioned In Today’s Show:

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

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

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

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

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

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In Today’s Episode You Will Learn:

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

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

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

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

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

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

Items Mentioned In Today’s Show:

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

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

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

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

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

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

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In Today’s Episode You Will Learn:

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

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

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

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

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

Items Mentioned In Today’s Show:

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

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

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

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

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

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

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In Today’s Episode You Will Learn:

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

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

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

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

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

Items Mentioned In Today’s Show:

Hunter’s Fave Book: Great Expectations by Charles Dickens

Hunter’s Most Recent Investment: Amplify Partners

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

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

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

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

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

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In Today’s Episode You Will Learn:

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

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

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

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

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

Items Mentioned In Today’s Show:

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

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

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

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

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

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

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In Today’s Episode You Will Learn:

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

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

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

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

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

Items Mentioned In Today’s Show:

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

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

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

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

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

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

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In Today’s Episode You Will Learn:

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

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

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

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

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

Items Mentioned In Today’s Show:

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

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

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

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

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

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

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In Today’s Episode You Will Learn:

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

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

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

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

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

Items Mentioned In Today’s Show:

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

Scott’s Most Recent Investment: Assembled Brands

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

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

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

---

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

 

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

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In Today’s Episode You Will Learn:

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

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

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

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

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

Items Mentioned In Today’s Show:

Andrew’s Fave Book: Creativity Inc

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

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

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

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

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In Today’s Episode You Will Learn:

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

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

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

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

Items Mentioned In Today’s Show:

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

Ted’s Most Recent Investment: Fullcast

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

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

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

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

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In Today’s Episode You Will Learn:

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

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

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

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

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

Items Mentioned In Today’s Show:

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

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

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

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

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

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In Today’s Episode You Will Learn:

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

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

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

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

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

Items Mentioned In Today’s Show:

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

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

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

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

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

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

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In Today’s Episode You Will Learn:

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

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

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

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

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

Items Mentioned In Today’s Show:

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

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

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

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

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

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In Today’s Episode You Will Learn:

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

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

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

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

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

Items Mentioned In Today’s Show:

Danny’s Fave Book: Killing Commendatore by Haruki Murakami

Danny’s Most Recent Investment: Goodeggs

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

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

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

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

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In Today’s Episode You Will Learn:

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

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

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

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

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

Items Mentioned In Today’s Show:

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

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

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

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

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

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In Today’s Episode You Will Learn:

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

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

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

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

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

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

Items Mentioned In Today’s Show:

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

Jeff’s Most Recent Investment: Radar Relay

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

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

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

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In Today’s Episode You Will Learn:

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

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

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

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

5.) Controversial capitals Round:

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

Items Mentioned In Today’s Show:

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

Leo’s Most Recent Investment: Interviewing.io

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

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

 

 

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

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In Today’s Episode You Will Learn:

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

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

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

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

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

Items Mentioned In Today’s Show:

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

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

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

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

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In Today’s Episode You Will Learn:

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

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

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

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

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

Items Mentioned In Today’s Show:

Avidan’s Fave Book: Drive by Daniel Pink

Avidan’s Most Recent Investment: Dusty Robotics

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

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

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

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In Today’s Episode You Will Learn:

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

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

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

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

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

Items Mentioned In Today’s Show:

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

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

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

 

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

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In Today’s Episode You Will Learn:

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

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

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

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

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

Items Mentioned In Today’s Show:

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

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

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

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

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

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In Today’s Episode You Will Learn:

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

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

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

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

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

Items Mentioned In Today’s Show:

Phil’s Fave Book: Clock of The Long Now

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

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

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

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In Today’s Episode You Will Learn:

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

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

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

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

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

Items Mentioned In Today’s Show:

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

Linda’s Most Recent Investment: Kadena

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

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

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

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In Today’s Episode You Will Learn:

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

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

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

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

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

Items Mentioned In Today’s Show:

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

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

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

 

 

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

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In Today’s Episode You Will Learn:

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

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

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

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

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

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

Items Mentioned In Today’s Show:

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

Phin’s Most Recent Investment: Ubiquity6

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

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

 

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

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In Today’s Episode You Will Learn:

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

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

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

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

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

Items Mentioned In Today’s Show:

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

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

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

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

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In Today’s Episode You Will Learn:

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

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

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

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

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

Items Mentioned In Today’s Show:

Woody’s Fave Book: The Boys in the Boat

Woody’s Most Recent Investment: Peloton

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

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

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

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In Today’s Episode You Will Learn:

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

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

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

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

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

Items Mentioned In Today’s Show:

Afton’s Fave Book: Motherhood Rescheduled

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

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

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

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In Today’s Episode You Will Learn:

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

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

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

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

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

Items Mentioned In Today’s Show:

Rebecca’s Fave Book: Pale Fire 

Rebecca’s Most Recent Investment: Modern Fertility

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

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

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

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In Today’s Episode You Will Learn:

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

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

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

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

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

 

Items Mentioned In Today’s Show:

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

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

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

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

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In Today’s Episode You Will Learn:

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

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

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

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

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

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

Items Mentioned In Today’s Show:

Sarah’s Fave Book: Creating the Kingdom of Ends

Sarah’s Most Recent Investment: Hipcamp

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

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

 

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

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In Today’s Episode You Will Learn:

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

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

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

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

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

Items Mentioned In Today’s Show:

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

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

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

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

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In Today’s Episode You Will Learn:

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

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

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

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

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

Items Mentioned In Today’s Show:

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

David’s Most Recent Investment: Adhawk

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

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

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

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

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In Today’s Episode You Will Learn:

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

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

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

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

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

Items Mentioned In Today’s Show:

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

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

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

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

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In Today’s Episode You Will Learn:

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

2.) Shabih has said to me before “founder relationships and their longevity really matter”. What does Shabih mean by this? How has this played out for Shabih in an investing environment? What have been Shabih’s subsequent learnings?

3.) How does Shabih identify the “3 buckets” that VCs source from? How does Shabih look to filter through opportunities at scale? What must he see in the deck? What are his quick no’s? What is Shabih’s framework for saying no both with efficiency and kindness? Why does Shabih believe this is one of the hardest parts of the role?

4.) What does the internal investment decision-making process look like at Gradient? Why do they believe that 2 partner meetings a week is optimal? Prior to that, how does Shabih structure his meetings with founders? Why does Shabih believe it is so important to go to them at their HQ? Should all investors go to the founder?

5.) Why is Shabih a strong believer in the decentralisation of talent away from the valley? What are the primary drivers for this decentralization? How does Shabih think about pricing in different regions? To what extent does it differ wildly? How does Shabih respond to traditional SaaS wisdom that you have to build your SaaS business in the valley?

Items Mentioned In Today’s Show:

Shabih’s Fave Book: Measure What Matters, When Breathe Becomes Air 

Shabih’s Most Recent Investment: Scotty.ai

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

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

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

Andrew Farah is the Founder & CEO @ Density, the startup that measures real-time occupancy of every room in your office. To date, they have raised over $16m in funding from some great friends of the show in the form of Founders Fund, Mark Suster @ Upfront, Ludlow Ventures, Jason Calacanis, Hiten Shah and Arjun Sethi, just to name a few. As for Andrew, prior to founding Density, he was a Managing Partner @ Rounded, a software development agency & product studio. There, Andrew and the team built the first Density prototype.

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In Today’s Episode You Will Learn:

1.) How Andrew made his way into the world of technology and product with Rounded and came to found the people counter of the next generation in Density?

2.) How does Andrew view the role of super-connectors today? What specific time has a super-connector really moved the needle for Andreq and changed the trajectory of Density? What can one do to first build relationships with these people? What can be done to sustain that relationship and really engage and deepen it?

3.) How does Andrew view the importance of “employee retention” in the ultimate success of a company? Density have never had an employee leave in 4 years, what does Andrew believe they have done right? What has not worked for them? What does he mean when he says, “the best leaders answer employees questions before they are asked”?

4.) What has Andrew found to be the commonalities in the truly special VCs? What do they do that makes them so special? How do they view the world and the assessment of companies that is so right? How does Andrew think about investor selection? Where does Andrew see many founders going wrong with this?

5.) Why does Andrew think that so many hardware startups fail today? What do they consistently underestimate and not understand? What are the core challenges in building a global supply chain? How does one have to think about cost of goods (COG) and unit economics when scaling hardware startups?

Items Mentioned In Today’s Show:

Andrew’s Fave Book: The Idea Factory: Bell Labs and the Great Age of American Innovation

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

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

Casper, the company that deliver a great night’s sleep at an incredible value. The team of engineers at Casper works nonstop prototyping, collecting data, and engineering what is certainly the most comfortable mattress. The Casper mattress has a unique combination of foams that provide the right pressure relief and alignment, so you feel perfectly balanced and comfortable. Try Casper yourself for 100 nights in your own home – RISK FREE. If you don’t love it, they come pick it up and refund you everything, no questions asked. Go to casper.com to try yours for 100 nights with FREE shipping and returns. Use code 20VC to save $50 on select mattresses today.

Lattice is the #1 people management solution for growing companies and helps companies like Asana, Reddit and Cruise build a strong company culture. With Lattice, it’s easy to launch 360 reviews, share ongoing feedback, facilitate 1:1s, set up goal tracking, and run employee engagement surveys. Lattice is the only solution that combines performance management and employee engagement, so operators can make sure top performers are happy. Lattice is giving away three months of Lattice free to 20VC listeners. Just go to lattice.com/20vc to receive the offer. Build an award-winning culture with Lattice. The #1 people management solution.

Barry Eggers is a Founding Partner @ Lightspeed, one of the world’s leading venture funds with a portfolio that includes the likes of Snapchat, Mulesoft, Affirm, StitchFix, AppDynamics, Nutanix and many more incredible companies. Barry himself has led investments in Snapchat, Metasolv Software (acquired post-IPO by ORCL), Calista Technologies (acquired by MSFT), Arbor Networks (acquired by DHR), Growth Networks (acquired by CSCO). As a result of his incredible success, Barry has been named to Forbes Midas List numerous times. Prior to VC, Barry held executive roles at Cisco Systems where he established many of the company’s largest distribution channels across OEMs, Service Providers, Distributors, and VARs. He also developed Cisco’s initial M&A process and directed the first wave of acquisitions and integrations for the company.

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In Today’s Episode You Will Learn:

1.) How Barry made his way from the world of Cisco to the wonderful world of venture and came to found one of the most successful firms of the decade in Lightspeed?

2.) How does Barry break up the development of the venture ecosystem into 3 distinct stages? What does Barry believe have been the positive changes? What does Barry believe have been the negative changes? Does Barry believe there is an excess supply of capital today? Why does Barry believe there are too many first time funds? What is the outcome?

3.) Did Barry always aim to build the multi-stage, multi-geography firm that he has built with Lightspeed, from the start? What have been the fundamental inflexion points for Lightspeed both in the increase in brand value and liquidity to LPs? Why does Barry believe building a firm really is an art? What should managers most look for in their first LPs?

4.) What does Barry believe are the 3 ways a venture firm can fail in a generational transition? How can firms incentivise young partners to see the career path and trajectory ahead? What must the older partners at the firm be willing to do? What have been Barry’s biggest lessons in their successful generational transition?

5.) Barry has sat on boards for over 21 years, how has Barry seen himself develop and evolve as a board member over time? What makes a truly functional board? What are the best practices? Who is the best board member Barry has ever sat on a board with? What makes Jim Goetz such a special board member?

Items Mentioned In Today’s Show:

Barry’s Fave Book: Quantum Computing: A Gentle Introduction (Scientific and Engineering Computation)

Barry’s Most Recent Investment: Audius

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

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

Philip Krim is the Founder & CEO @ Casper, the global sleep company that launched in 2014 offering perfect mattresses directly to consumers. Since then they have raised over $239m in funding from the likes of NEA, Lerer Hippeau, IVP, Norwest Venture partners and even include Leonardo Di Caprio on their cap table. As for Philip, he is a serial entrepreneur having founded 2 previous startups, launching his first business out of his very own dorm room at the University of Texas. Due to his immense success, he has been profiled in The New York Times, The Wall Street Journal and been awarded a TechCrunch Crunchie award for Best in E-commerce.

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In Today’s Episode You Will Learn:

1.) How Philip made his way into the world of startups and came to launch one of the most successful consumer brands of our day in the form of Casper?

2.) We continuously hear about “the end of retail”. What does retail done poorly mean to Philip? How does he perceive the future of retail and retail done right? How does retail fundamentally change the margin structure of an originally online brand like Casper? What does Philip perceive to be the biggest challenge to opening up retail significantly?

3.) Why does Philip think we have seen many online mattress brands struggle over the past year? How has this affected how he operates and executes the plan with Casper? How does Philip think about diversification within customer acquisition channels? How does Philip assess the saturation rate of different distribution channels?

4.) Casper’s latest lead investor was a strategic investor, Target. How does Philip think about accepting strategic funds? What was the internal debate and decision-making process? What advice would Philip have to founders contemplating accepting strategic money? How can strategics sometimes have ulterior motives?

5.) Does Philip agree with many former CEOs on the show, the most important role of the CEO is management upscaling? What other functions does Philip consider core? How did Philip think about building out the core of his C-Suite? Does he wish he had done it earlier? What element of the C-Suite was the hardest to hire for?

Items Mentioned In Today’s Show:

Philip’s Fave Book: Elon Musk: How the Billionaire CEO of SpaceX and Tesla is Shaping our Future, Bad Blood: Secrets and Lies in a Silicon Valley Startup

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

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

Daniel Gross is the Founder @ Pioneer and the Head of AI @ Y Combinator. Taking them in turn, Pioneer is the home for ambitious outsiders of the world where they are building a community of creative young people working on interesting projects around the globe. YC is obviously the world’s most successful accelerator with alumni that includes the likes of Airbnb, Dropbox, Reddit, Flexport and many more incredible companies. Prior to Pioneer and YC, Daniel was a Director @ Apple where he focused on machine learning, as a result of his prior company, Cue (also a YC company) being acquired by Apple in 2013. Finally, Daniel also has one of the valley’s most impressive angel portfolios with investments in OpenDoor, Cruise (acquired by GM), Gusto and Github, just to name a few.

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In Today’s Episode You Will Learn:

1.) How Daniel made his way from a military camp in Israel to start a company at YC to selling the company to Apple to now, creating a global community of the world’s most ambitious people?

2.) What does Daniel believe is the commonality of truly great people? Why did Daniel decide to start Pioneers now? What are the terms for entering Pioneers? How is Daniel looking to create the global talent engine through gamification with Pioneers? Why is gamification such a strong tool to understand human motivation?

3.) Why did Daniel decide it was the right decision to bring the Pioneers to SF? In the world of decentralized entrepreneurship, why did Daniel feel it necessary to bring everyone to the valley? What does Daniel believe Silicon Valley needs to solve if it is to become the home for crypto and frontier tech? What role does optimism play in the success of SF?

4.) The program is funded through Stripe and Marc Andreesen, many have suggested this poses conflict with potential optionality on projects and talent, how does Daniel think about this conflict? Why is it not a concern? What other challenges does Daniel forsee as being the biggest barriers to the success of Pioneer?

5.) How does Daniel think about KPI’s for the coming 12 months? What are his core KPI’s? How does Daniel construct a framework that will allow him to love previously disliked tasks? How can anyone do this with success?

Items Mentioned In Today’s Show:

Daniel’s Fave Book: Finite and Infinite Games, Enders Game

Daniel’s Most Recent Investment: Jump, Retool

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

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

Joist has built the go-to platform for contractors. Joist enables contractors to professionally handle everyday tasks like estimating, invoicing, collecting payments, and manage projects, while also helping them grow their businesses as a streamlined CRM. More than 500 thousand contractors have used the Joist platform to manage more than $8.5 billion in invoiced work in North America, the UK, and Australia. Learn more at joist.com. WePay’s got a great case study about how another platform, TeamSnap, is working with WePay to make payments its #1 revenue stream… more than its subscription business. Get it at wepay.com/harry.

Lattice is the #1 people management solution for growing companies and helps companies like Asana, Reddit and Cruise build a strong company culture. With Lattice, it’s easy to launch 360 reviews, share ongoing feedback, facilitate 1:1s, set up goal tracking, and run employee engagement surveys. Lattice is the only solution that combines performance management and employee engagement, so operators can make sure top performers are happy. Lattice is giving away three months of Lattice free to 20VC listeners. Just go to lattice.com/20vc to receive the offer. Build an award-winning culture with Lattice. The #1 people management solution.

Heather Fernandez is the Founder & CEO @ Solv, the startup that simplifies everyday healthcare by providing access to high quality, last-minute care. To date, Heather has raised over $23m in funding from some of the great of the world of venture including Bill Gurley @ Benchmark, Theresia @ Aspect, James Slavet @ Greylock and Pete Flint @ NFX. Prior to Solv, Heather was part of the early team @ Trulia, where she led advertising product, marketing, and sales strategy and saw the team go from 20 people through to the $2.5B acquisition by Zillow Group. Before Trulia, Heather was at Morgan Stanley and more interestingly was National Deputy Press Secretary for Senator John McCain’s 2000 presidential campaign. If all of that was not enough, Heather is also a Board Member at the global behemoth, Atlassian.

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In Today’s Episode You Will Learn:

1.) How Heather made her way into the world of startups from the world of politics? How she came to be one of the early team at Trulia? What was the a-ha moment for Solv?

2.) How does Heather fundamentally define “culture”? What is the trust equation? Why does it play such a central role in successful culture building? What does Theather mean when she discusses “constructive candor”? What are the common mistakes Heather sees founders make when it comes to scaling culture? What literal actions can be done to instil trust and respect within the team?

3.) Does Heather agree with James @ ThredUp, “marketplaces founders have to be immensely stubborn”? Would Heather agree with Leah @ TaskRabbit with regards to marketplace NPS and “one side of the equation will always be less content”?

4.) What advice would Heather give to managers to maximize their impact in their organisation and their career? How does Heather think about bringing in the right people at various stages of the company? How does it change with scale? On funding, Solv has raised $23m, how does Heather think about when is the right time to pour fuel on the fire?

5.) Heather is also on the board of Atlassian, so what are the core benefits of simultaneously sitting on a board and managing your own board? What have been Heather’s biggest learnings from her time on the Atlassian board? How do the best founders manage their boards successfully?

Items Mentioned In Today’s Show:

Heather’s Fave Book: The American Political Tradition and the Men Who Made it

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

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

Are you told your standards are too high, well The League is the app that tells you to keep them that way, they know your time is valuable so simply tell them your preferences and they will handle the scouting and vetting for you. Plus even better, your profile will only ever be seen by people who match your preferences, matches expire after 21 days and so there are no drawn-out games and they even require LinkedIn to protect your privacy and block you from matching with co-workers and business connections. You can apply now by downloading The League on the app store or heading to The League.com

Zoom is the fastest-growing video and web conferencing service, providing one consistent enterprise experience that allows you to engage in an a variety of activities including video meetings and webinars, collaboration-enabled conference rooms, and persistent chat all in one platform. Plus, it is the easiest solution to manage, scale, and use, and has the most straightforward, affordable pricing. And you can see for yourself! Sign up for a free account (not a trial!). Just visit Zoom.us.

Culture Amp is the platform that makes it easy to collect, understand and act on employee feedback. From onboarding surveys to company-wide engagement, individual effectiveness and more, the platform manages multiple sources of feedback and connects the dots for you and that is why companies like Slack, Nike, Oracle and Lyft all trust Culture Amp. It enables leaders to make better decisions, demonstrate impact and turn your company culture into a competitive edge.  Find out more on cultureamp.com.

Avichal Garg is the Managing Partner @ Electric Capital, one of the leading crypto asset management firms today investing in both liquid and illiquid tokens that are emerging stores of value and rooted in novel technology. Prior to Electric they personally invested in Anchor, Bitwise, Basecoin and more. As for Avichal as well as Electric, he is a part-time partner at YC and prior to YC, he was Director of Product Management at Facebook where he led the Local product team (a $3.5Bn line of business at the time). Before FB, Avichal worked on Search and Ads at Google, started and sold a few companies, and invested in startups including Optimizely, Boom, Color, Cruise, Instawork, CaseText, and many more.

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In Today’s Episode You Will Learn:

1.) How Avichal made his way into the world of startups, began angel investing, discovering the power of crypto and why now for Electric Capital?

2.) How does Avichal break the world of crypto into 4 fundamentally distinct buckets today? Which 2 elements does Avichal believe will be the biggest value accruers? What is the core question to ask when assessing a crypto opportunity today? How does angel investing compare to crypto investing?

3.) Where are the majority of ICO dollars going today? Why does Avichal believe that ICOs in large part do not fundamentally make sense from an investment and pricing perspective? How does Avichal think about liquidity in the world of crypto? As an institutional manager, what mindset does Avichal embrace when liquidity is possible?

4.) Why does Avichal believe that regulation and government controls is the opposite of the real risk to the space? If this is not the biggest risk, what does Avichal believe is the biggest risk to the potential of the space? Why does Avichal believe that the US government have handled the space with nuance and intellect?

5.) Why does Avichal believe that decentralized teams will not work? How does this correlate to the progression of platform complexity with time? Why does Avichal believe this will lead to the re-centralization of talent back to Silicon Valley? What catalysts will act to speed this up or hamper it’s re-centralisation?

Items Mentioned In Today’s Show:

Avichal’s Fave Book: Ender’s Game

Avichal’s Most Recent Investment: Coda Cryptocurrency Protocol

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

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

Are you told your standards are too high, well The League is the app that tells you to keep them that way, they know your time is valuable so simply tell them your preferences and they will handle the scouting and vetting for you. Plus even better, your profile will only ever be seen by people who match your preferences, matches expire after 21 days and so there are no drawn-out games and they even require LinkedIn to protect your privacy and block you from matching with co-workers and business connections. You can apply now by downloading The League on the app store or heading to The League.com

Zoom is the fastest-growing video and web conferencing service, providing one consistent enterprise experience that allows you to engage in an a variety of activities including video meetings and webinars, collaboration-enabled conference rooms, and persistent chat all in one platform. Plus, it is the easiest solution to manage, scale, and use, and has the most straightforward, affordable pricing. And you can see for yourself! Sign up for a free account (not a trial!). Just visit Zoom.us.

Culture Amp is the platform that makes it easy to collect, understand and act on employee feedback. From onboarding surveys to company-wide engagement, individual effectiveness and more, the platform manages multiple sources of feedback and connects the dots for you and that is why companies like Slack, Nike, Oracle and Lyft all trust Culture Amp. It enables leaders to make better decisions, demonstrate impact and turn your company culture into a competitive edge.  Find out more on cultureamp.com.

 

Dylan Serota is the Founder & Chief Strategy Officer @ Terminal, the startup that helps you create world-class technical teams through remote operations as a service. They recently raised a phenomenal $13m Series A with some of the world’s most renowned names including Lightspeed, KPCB, Craft, Thiel, Atomic and Jerry Yang just to name a few. As for Dylan, he is also a Founder-in-Residence @ Atomic, one of the valley’s most exciting new institutions which both founds and funds companies and includes the likes of Hims, TalkIQ (acq by Dialpad) and more. Prior to Atomic and Terminal, Dylan was Head of Platform @ Eventbrite where he led platform product org, built third-party developer ecosystem and platform partnerships.

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In Today’s Episode You Will Learn:

1.) How Dylan made his way into the world of startups with Eventbrite and how that led to his realisation on the future of development operations with Terminal?

2.) Why does Dylan believe that it is important for startups to build distributed teams earlier in their growth curve than often suggested? What are the key aspects to making remote teams work well? Why does Dylan believe that “companies overvalue their culture”? How does Dylan assess culture across remote teams?

3.) Jason lemkin says “startups can either hire a stretch VP or a burnt out mediocre VP”, does Dylan agree with this? How does Dylan assess the balance between hiring functional specialists vs jack of all trades? When is the right time to make the transition from generalist to specialist?

4.) Hw does Dylan analyze and assess a startup leaderships team ability to adapt and prioritize speed? What is key to successful decision-making today in startups? How does Dylan think about the importance of speed when it comes to product ideation and iteration?

5.) What does Dylan believe is the biggest mistake many people make early in their career? What are the commonalities of the truly successful people in how they have structured their careers? How does Dylan think about the balance between title vs salary vs experience? What should one optimise for and when?

Items Mentioned In Today’s Show:

Dylan’s Fave Book: The Selfish Gene by Richard Dawkins

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

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

Are you told your standards are too high, well The League is the app that tells you to keep them that way, they know your time is valuable so simply tell them your preferences and they will handle the scouting and vetting for you. Plus even better, your profile will only ever be seen by people who match your preferences, matches expire after 21 days and so there are no drawn-out games and they even require LinkedIn to protect your privacy and block you from matching with co-workers and business connections. You can apply now by downloading The League on the app store or heading to The League.com

Zoom is the fastest-growing video and web conferencing service, providing one consistent enterprise experience that allows you to engage in an a variety of activities including video meetings and webinars, collaboration-enabled conference rooms, and persistent chat all in one platform. Plus, it is the easiest solution to manage, scale, and use, and has the most straightforward, affordable pricing. And you can see for yourself! Sign up for a free account (not a trial!). Just visit Zoom.us.

Culture Amp is the platform that makes it easy to collect, understand and act on employee feedback. From onboarding surveys to company-wide engagement, individual effectiveness and more, the platform manages multiple sources of feedback and connects the dots for you and that is why companies like Slack, Nike, Oracle and Lyft all trust Culture Amp. It enables leaders to make better decisions, demonstrate impact and turn your company culture into a competitive edge.  Find out more on cultureamp.com.

Jeff Fagnan is Founding Partner @ Accomplice, one of the East Coast’s leading early-stage funds with a portfolio including the likes of AngelList, PillPack (acq by Amazon), Freshbooks, Hopper, Secret Escapes and many more incredible companies. Accomplice is also unique as it is a platform builder creating incredible initiatives such as Spearhead, Maiden Lane and Boston Syndicates, really moving the needle in seeding local ecosystems. As for Jeff he is well known as a founding investor, working with most of his portfolio since inception, sometimes as a co-founder including Veracode (Sold to CA Technologies‍). Jeff also sits on the board of AngelList, PillPack, InsightSquared, Hopper, Freshbooks and more.

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In Today’s Episode You Will Learn:

1.) How Jeff made his way into the world of VC from consulting over 18 years ago? How did his experience of the bubble influence Jeff’s mindset and thinking?

2.) What did Jeff learn about building an optimal venture partnership with the transition from the 23 partner Atlas to the tight-knit Accomplice? Where does Jeff believe most venture partnerships go wrong today? What does Jeff believe is the right size partnership in venture? Why does Jeff believe that partners are there to save each other from themselves?

3.) How did Jeff’s experience with Atlas effect his views on portfolio construction? Why does Jeff advocate for the model of raising $200m every 2.5 years for a pure seed strategy? How does Jeff think about building an effective reserve strategy? Why does Jeff not believe pro-rata should be guaranteed? Why does Jeff believe force ranking a portfolio is dangerous?

4.) Jeff believes the best VCs are able to manage 2 things, what are those 2 things? From his 18 years on boards, what does Jeff believe makes the truly special board member? Who is the best he has worked with and why? How does Jeff look to gain the balance of being both proactive to opportunities and reactive to inbound?

5.) Accomplice has recently made it’s foray into the West Coast, what was the thinking behind that move? How does Accomplice think about establishing mindshare as a new entrant in a hotly contested environment? What does Jeff believe is the key to successful geographic expansion in venture?

Items Mentioned In Today’s Show:

Jeff’s Fave Book: Where The Wild Things Are 

Jeff’s Most Recent Investment: Perch

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

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

Are you told your standards are too high, well The League is the app that tells you to keep them that way, they know your time is valuable so simply tell them your preferences and they will handle the scouting and vetting for you. Plus even better, your profile will only ever be seen by people who match your preferences, matches expire after 21 days and so there are no drawn-out games and they even require LinkedIn to protect your privacy and block you from matching with co-workers and business connections. You can apply now by downloading The League on the app store or heading to The League.com

Zoom is the fastest-growing video and web conferencing service, providing one consistent enterprise experience that allows you to engage in an a variety of activities including video meetings and webinars, collaboration-enabled conference rooms, and persistent chat all in one platform. Plus, it is the easiest solution to manage, scale, and use, and has the most straightforward, affordable pricing. And you can see for yourself! Sign up for a free account (not a trial!). Just visit Zoom.us.

Culture Amp is the platform that makes it easy to collect, understand and act on employee feedback. From onboarding surveys to company-wide engagement, individual effectiveness and more, the platform manages multiple sources of feedback and connects the dots for you and that is why companies like Slack, Nike, Oracle and Lyft all trust Culture Amp. It enables leaders to make better decisions, demonstrate impact and turn your company culture into a competitive edge.  Find out more on cultureamp.com.

Armon Dadgar is the Founder & CTO @ Hashicorp, the open-source software company that provides consistent workflows to provision, secure, connect and run any infrastructure for any application. To date, Hashicorp has raised over $74m in VC funding from many friends of the show including Scott Raney @ Redpoint, Glenn Solomon @ GGV, Semil Shah, True Ventures and Mayfield. As for Armon, today he leads the Hashicorp research group and focused on industrial research in the security and large-scale system management space. Prior to founding Hashicorp, Armon was a software engineer @ Kiip and Amazon.

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In Today’s Episode You Will Learn:

1.) How Armon made his way from intern at Amazon to founding Hashicorp and creating the game-changing suite of tools in the world of DevOps?

2.) Hashicorp has enjoyed success after success with new products, so what does Armon believe is the secret to continuous product innovation? What does Armon mean when he says “there are really 3 phases to product adoption”? How does Armon determine between vision for a product and the realism when it is not working, when launching products?

3.) Hashicorp only recently started generating revenue, why was now the right time? At what point does one go from building products for the community to building products people will pay for? How does Armon assess professional services today? What does Armon believe are the 2 foundational problems with “professional services”?

4.) Many VCs suggest it’s impossible to build big infrastructure businesses today given the commoditizing forces to open source and cloud computing. How have Hashicorp navigated that and bucked that conventional wisdom? How has Armon also bucked the conventional wisdom on the importance of focus? What core tenets must remain if one wants to go against this emphasis on focus?

5.) Armon and his co-founder brought on a CEO early, what was the realisation moment for the need to bring in an external CEO? How did Armon look to get comfortable with this transition? What advice would Armon give to founders contemplating bringing in an external CEO? With the benefit of hindsight, what would Armon do differently if he had the time again?

Items Mentioned In Today’s Show:

Armon’s Fave Book: To The Lighthouse by Virginia Woolf

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

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

Are you told your standards are too high, well The League is the app that tells you to keep them that way, they know your time is valuable so simply tell them your preferences and they will handle the scouting and vetting for you. Plus even better, your profile will only ever be seen by people who match your preferences, matches expire after 21 days and so there are no drawn-out games and they even require LinkedIn to protect your privacy and block you from matching with co-workers and business connections. You can apply now by downloading The League on the app store or heading to The League.com

Zoom is the fastest-growing video and web conferencing service, providing one consistent enterprise experience that allows you to engage in an a variety of activities including video meetings and webinars, collaboration-enabled conference rooms, and persistent chat all in one platform. Plus, it is the easiest solution to manage, scale, and use, and has the most straightforward, affordable pricing. And you can see for yourself! Sign up for a free account (not a trial!). Just visit Zoom.us.

Culture Amp is the platform that makes it easy to collect, understand and act on employee feedback. From onboarding surveys to company-wide engagement, individual effectiveness and more, the platform manages multiple sources of feedback and connects the dots for you and that is why companies like Slack, Nike, Oracle and Lyft all trust Culture Amp. It enables leaders to make better decisions, demonstrate impact and turn your company culture into a competitive edge.  Find out more on cultureamp.com.

Nick Brown is Managing Partner @ Imaginary, founded alongside Net-A-Porter founder, Natalie Massenet, Imaginary invests in early–stage opportunities at the intersection of retail and technology. Included in their incredible portfolio is the likes of Glossier, Daily Harvest, Farfetch, Everlane and many more awesome companies. Prior to co-founding Imaginary, Nick was a Partner at 14W Venture Partners where he invested in the likes of Goop, Outdoor Voices, The Real Real and Business of Fashion just to name a few. Before that Nick was Head of New Media @ NV Investments.

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In Today’s Episode You Will Learn:

1.) How Nick made his way into the world of venture and consumer investing from the days of investment banking?

2.) We have seen an explosion in the world of consumer with regards to D2C brands, does Nick believe we are in a D2C bubble? There is a lot of skepticism around physical product companies being venture businesses, so what are the core considerations for Nick when investing in physical product brands today?

3.) Having backed the likes of Glossier, Farfetch, Everlane etc, what does Nick believe are some of the leading indicators from the early days whether a company has a sustaining and authentic brand? What does Nick believe is the future for direct to consumer of the next 24-36 months? What is he most excited by?

4.) How does Nick think about the interaction between D2C brands and wholesale and physical retail? When is the right time to pull the wholesale lever? What does Nick believe is a healthy ratio between paid to organic customer acquisition? What are the commonalities in the consumer brands that have broken out within his portfolio?

5.) In terms of character traits, what commonalities does Nick see in the most successful consumer founders he has backed today? We have seen a rise in the celebrity founder over the last few years, so what is the role of the celebrity founder? When does it work? When does it not work? How does the future of celebrity founder look to Nick?

Items Mentioned In Today’s Show:

Nick’s Fave Book: To Kill A Mockingbird

Nick’s Most Recent Investment: Fitplan

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

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

Are you told your standards are too high, well The League is the app that tells you to keep them that way, they know your time is valuable so simply tell them your preferences and they will handle the scouting and vetting for you. Plus even better, your profile will only ever be seen by people who match your preferences, matches expire after 21 days and so there are no drawn-out games and they even require LinkedIn to protect your privacy and block you from matching with co-workers and business connections. You can apply now by downloading The League on the app store or heading to The League.com

Zoom is the fastest-growing video and web conferencing service, providing one consistent enterprise experience that allows you to engage in an a variety of activities including video meetings and webinars, collaboration-enabled conference rooms, and persistent chat all in one platform. Plus, it is the easiest solution to manage, scale, and use, and has the most straightforward, affordable pricing. And you can see for yourself! Sign up for a free account (not a trial!). Just visit Zoom.us.

Culture Amp is the platform that makes it easy to collect, understand and act on employee feedback. From onboarding surveys to company-wide engagement, individual effectiveness and more, the platform manages multiple sources of feedback and connects the dots for you and that is why companies like Slack, Nike, Oracle and Lyft all trust Culture Amp. It enables leaders to make better decisions, demonstrate impact and turn your company culture into a competitive edge.  Find out more on cultureamp.com.

Adam Goldberg is a Partner @ Lightspeed Venture Partners, one of the world’s leading funds with a portfolio including the likes of SNAP, Mulesoft, Max Levchin’s Affirm, AppDynamics and many more incredible companies. As for Adam, at age 13, Adam enrolled as a full-time student at UC Berkeley, where he studied pure and applied mathematics and conducted research in number theory and machine learning. He went on to work as a mathematician for the Department of Defense and as a researcher Berkeley, Wisconsin-Madison and Stanford. Following that, Adam worked as an engineer at Palantir and Dropbox and was an early product manager at Rubrik. In 2016, Adam left Rubrik to become a partner at Lightspeed where he has invested in the likes of Basis, Vector and Totemic Labs, just to name a few.

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In Today’s Episode You Will Learn:

1.) How Adam made his way into the world of venture from the department of defence and working at titans such as Palantir and Dropbox?

2.) Why does Adam believe the rate of founder learning is the most important skill that an investor can evaluate and assess? What does optimizing for learning really mean to Adam? In practice, what can one do to optimize for learning? What are the common traits and signs of those founders that do this well?

3.) Why does Adam believe that there remains today no mass market decentralised consumer product? What is needed for this to happen? How does Adam forsee the development of token economics over the coming years? What novel token financing solutions does Adam respect? What is required within token economics for Adam to gain real comfort?

4.) Why does Adam believe that the Telegram ICO got such attention? Why is Adam fundamentally bullish on the opportunity? What 2 core characteristics does Telegram have that are required for crypto projects to be successful? On the other side of the table, where is there cause for concern when reviewing the opportunity?

5.)How does Adam think about “betting on fundamental trade-offs in crypto”? What are the 4 key trade-offs that founders must contemplate? What are the trade-offs that Adam is willing to accept vs not accept? How does Adam envisage the willingness to accept trade-offs so widely, change over time in the space?

Items Mentioned In Today’s Show:

Adam’s Fave Book: Flowers for Algernon

Adam’s Most Recent Investment: Strangeworks

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

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

Are you told your standards are too high, well The League is the app that tells you to keep them that way, they know your time is valuable so simply tell them your preferences and they will handle the scouting and vetting for you. Plus even better, your profile will only ever be seen by people who match your preferences, matches expire after 21 days and so there are no drawn-out games and they even require LinkedIn to protect your privacy and block you from matching with co-workers and business connections. You can apply now by downloading The League on the app store or heading to The League.com

Zoom is the fastest-growing video and web conferencing service, providing one consistent enterprise experience that allows you to engage in an a variety of activities including video meetings and webinars, collaboration-enabled conference rooms, and persistent chat all in one platform. Plus, it is the easiest solution to manage, scale, and use, and has the most straightforward, affordable pricing. And you can see for yourself! Sign up for a free account (not a trial!). Just visit Zoom.us.

Culture Amp is the platform that makes it easy to collect, understand and act on employee feedback. From onboarding surveys to company-wide engagement, individual effectiveness and more, the platform manages multiple sources of feedback and connects the dots for you and that is why companies like Slack, Nike, Oracle and Lyft all trust Culture Amp. It enables leaders to make better decisions, demonstrate impact and turn your company culture into a competitive edge.  Find out more on cultureamp.com.

Eddy Lu is the Co-Founder & CEO @ GOAT, the largest marketplace in the world for buying and selling authentic sneakers. To date, GOAT have raised over $97m in VC funding from some of the best in the business including Accel, Index, Upfront and include angel investments from Elad Gil, Ashton Kutcher and Alexis Ohanian. Prior to GOAT, Eddy enjoyed numerous different roles including founding a chain of Japanese dessert stores building a slew of different 99c apps and started on Wall St with Lehmann Brothers and Deloitte.

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In Today’s Episode You Will Learn:

1.) How Eddy made his way from Wall St to making 99c apps to creating a chain of Japanese desert stores to founding the world’s largest sneaker marketplace in GOAT?

2.) Pivoting from social dining to sneaker marketplace, how does Eddy determine between mission and passion for the vision vs when something is simply not working? What core metrics made Eddy realise this pivot was needed? How did Eddy communicate the pivot to the existing investor base? How did he get them on board for the next chapter?

3.) Over the years, GOAT has had many investors wanting to invest, how does Eddy approach investor selection? What advice does Eddy have on optimising for valuation and the terms that founders should really focus on? What have been the biggest lessons from having former Twitter COO, Adam Bain on the GOAT board?

4.) Does Eddy agree with Paul at Canvas that marketplace founders should give up if they do not have differentiated supply? What does Eddy believe is the core characteristic of the most successful marketplaces? To what extent does Eddy believe that early marketplaces must rely on existing distribution and offline activities to scale?

5.) Eddy took the decision to merge with Flight Club, what was behind the decision to open up the business to physical retail? Why does Eddy believe that physical retail does not affect the margin structure massively when compared to it’s online counterpart? How does Eddy assess the categories that make sense for physical retail between those that do not?

Items Mentioned In Today’s Show:

Eddy’s Fave Book: Crime and Punishment 

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

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

Are you told your standards are too high, well The League is the app that tells you to keep them that way, they know your time is valuable so simply tell them your preferences and they will handle the scouting and vetting for you. Plus even better, your profile will only ever be seen by people who match your preferences, matches expire after 21 days and so there are no drawn-out games and they even require LinkedIn to protect your privacy and block you from matching with co-workers and business connections. You can apply now by downloading The League on the app store or heading to The League.com

Zoom is the fastest-growing video and web conferencing service, providing one consistent enterprise experience that allows you to engage in an a variety of activities including video meetings and webinars, collaboration-enabled conference rooms, and persistent chat all in one platform. Plus, it is the easiest solution to manage, scale, and use, and has the most straightforward, affordable pricing. And you can see for yourself! Sign up for a free account (not a trial!). Just visit Zoom.us.

Culture Amp is the platform that makes it easy to collect, understand and act on employee feedback. From onboarding surveys to company-wide engagement, individual effectiveness and more, the platform manages multiple sources of feedback and connects the dots for you and that is why companies like Slack, Nike, Oracle and Lyft all trust Culture Amp. It enables leaders to make better decisions, demonstrate impact and turn your company culture into a competitive edge.  Find out more on cultureamp.com.

Jason Stoffer is Managing Partner @ Maveron, the consumer-only venture fund backing a new breed of brands. Their stellar portfolio includes the likes of eBay, Zulily, General Assembly, Allbirds and Dia&Co, just to name a few. As for Jason, Jason is the master of all things consumer education, e-commerce and marketplace businesses. He has been a Board Member of a number of category-leading consumer businesses, such as zulily (Nasdaq: ZU), General Assembly (acquired by Adecco), Common and more. Prior to Maveron, Jason was Senior Director of Strategic Operations at Career Education Corp where he saw the business scale to a market cap of over $4.5Bn.

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In Today’s Episode You Will Learn:

1.) How Jason made his way into the world of VC from the world of journalism? What were his biggest takeaways from seeing the boom and bust cycle of 2001 and 2008?

2.) Why does Jason believe that moats matter as much, if not more than brand today? How can founders look to create the strongest form of defensibility? How does Jason analyze the 2 paths for consumer businesses today; raise large amounts of capital and buy growth or raise little, grow slowly, understand unit economics and channels over time? Does Jason think we will see a graveyard of immensely funded consumer businesses?

3.) How does Jason view paid acquisition today? Does Jason agree with Peter Fenton. “there is a lack of free and open distribution in consumer today”? When does Jason believe that consumer founders should really focus on CAC/LTV? What metrics really matter in the early days for consumer? How does Jason analyse acquisition channel mortality? When does he mean when he says, “CAC works, until it does not”?

4.) Jason has said before that “VC is a struggle”. What elements does Jason find most challenging? How does Jason deal witht he shit hit the fan moments as a VC? Can VCs in this hyper-competitive world be openly vulnerable in Jason’s eyes? How has Jason seen his approach to hard and challenging situations in VC develop over time?

5.) Does Jason believe we are in a consolidatory environment today or will we see the next generation of mega consumer brands being built? When investing, does Jason ask, who is the potential acquirer? Why? What multiple is achievable? Would Jason agree with Kirsten Green that “Amazon does more to make the market than destroy it”? How does Amazon affect Jason’s investment philosophy and approach?

Items Mentioned In Today’s Show:

Jason’s Fave Book: 100 Years of Solitude

Jason’s Most Recent Investment: Imperfect Produce

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

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

Are you told your standards are too high, well The League is the app that tells you to keep them that way, they know your time is valuable so simply tell them your preferences and they will handle the scouting and vetting for you. Plus even better, your profile will only ever be seen by people who match your preferences, matches expire after 21 days and so there are no drawn-out games and they even require LinkedIn to protect your privacy and block you from matching with co-workers and business connections. You can apply now by downloading The League on the app store or heading to The League.com

Zoom is the fastest-growing video and web conferencing service, providing one consistent enterprise experience that allows you to engage in an a variety of activities including video meetings and webinars, collaboration-enabled conference rooms, and persistent chat all in one platform. Plus, it is the easiest solution to manage, scale, and use, and has the most straightforward, affordable pricing. And you can see for yourself! Sign up for a free account (not a trial!). Just visit Zoom.us.

Culture Amp is the platform that makes it easy to collect, understand and act on employee feedback. From onboarding surveys to company-wide engagement, individual effectiveness and more, the platform manages multiple sources of feedback and connects the dots for you and that is why companies like Slack, Nike, Oracle and Lyft all trust Culture Amp. It enables leaders to make better decisions, demonstrate impact and turn your company culture into a competitive edge.  Find out more on cultureamp.com.

Fritz Lanman is the CEO @ ClassPass, the startup that provides the most flexible fitness membership ever. To date, they have raised over $154m in VC funding from the likes of Thrive, GV, CRV, Fifth Wall and Temasek just to name a few. As for Fritz, prior to ClassPass he was the Founder & CEO @ Livestar, a mobile recommendations startup that was acquired by Pinterest. Before that, he was a Senior Director in the Corporate Strategy Group @ Microsoft where he led several multi-billion dollar M&A evaluations and strategy projects including the Facebook investment and Yahoo deal. If that was not enough, Fritz is also a tremendously successful angel with a portfolio including the likes of Square, Pinterest, Wish, Flexport, Everlane and 75 or so more companies.

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In Today’s Episode You Will Learn:

1.) How Fritz made his way into the world of startups with Microsoft? How that led to angel investments in Wish, Flexport, Square and more? How he came to be CEO @ ClassPass?

2.) How did the $250m Microsoft investment in Facebook come about? What made Fritz so confident he told Steve Ballmer he was willing to bet his career it would be a $10Bn company? What was the decision-making process internally around that deal?

3.) How does Fritz assess his own asset allocation strategy? Why does Fritz not agree with thesis-driven angel investing? When starting angel investing, how did he approach portfolio construction? Why does Fritz believe it is immensely synergistic to be both an operator and angel? As a result, how does Fritz approach placing investors in a quadrant between helpfulness and high maintenance?

4.) Why does Fritz believe that your investor cannot be your recruiter? What have been Fritz biggest learnings on continuously attracting the best talent? Why does Fritz believe that it is BS that one should not celebrate fundraising? Ultimately, what does Fritz elieve fundraising signifies?

5.) ClassPass has expanded to 34 markets over the last few years, how does Fritz determine when is the right time to pour fuel on the fire? What are the 2 fundamental questions one must ask before you do? Does Fritz believe that aggressive growth and capital efficiency are mutually exclusive? How does Fritz think about capital efficiency with ClassPass today?

Items Mentioned In Today’s Show:

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

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

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

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

Whether you’re starting your own small business or getting serious about making your small business more efficient, you need to invite FreshBooks to the table. FreshBooks makes cloud accounting software that’s so ridiculously easy to use and you’ll quickly understand why over 10 million people use it to radically streamline how they deal with their admin and paperwork. Plus, FreshBooks can handle a lot more than accounting related tasks. Using FreshBooks is kind of like having your own admin assistant who’s got your back, 24/7. To claim your 30-day unrestricted free trial, click here enter Twenty Minute VC in the “how did you hear about us section”.

Highfive makes meetings better for thousands of organizations with insanely simple video conferencing designed for meeting rooms. It’s the easiest-to-use solution, with all-in-one hardware and intuitive cloud software. Plus, it’s a high-quality experience with industry-leading audio powered by Dolby Voice. It’s so easy to use, that there’s no pin codes or app downloads. Just click a link in your browser, and you’re in the meeting. With customers in over 100 countries, Highfive is already trusted by the likes of Evernote, Expensify, and Betterment and you can learn more by simply heading over to highfive.com.

Elad Gil is the Founder @ Color, the startup that shows you your genes can help you make better health decisions. They have raised over $112m in funding from the likes of General Catalyst, CRV, 8VC, Aaron Levie and more incredible names. Elad is also an incredible angel, counting the likes of Airbnb, Stripe, Optimizely, Opendoor and Wish all in his portfolio. Now Elad is adding a new string to his very talented bow with the release of his book, High Growth Handbook, published by Stripe in which Elad interviews 14 leaders from the valley from Marc Andreesen to Reid Hoffman to Patrick Collison. Plus shares his own experiences from Google, growing from 1,500 to 15,000 and Twitter, growing from 100 to 1,500. High Growth Handbook is now available for sale on Amazon, Kindle, Kobo.

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In Today’s Episode You Will Learn:

1.) How Elad made his way into the world of startups, came to found 2 companies that sold to Twitter and Google and came to invest in Airbnb, Stripe, Wish etc?

2.) How does Elad define the role of the CEO today? What are the commonalities in those truly great CEOs? How do the very best CEOs hire the very best execs? How do they address role allocation internally? How do they determine between employees that do and do not scale with the firm? Where do CEOs make the most fatal mistakes in high growth startups?

3.) Why are pre-emptive rounds so common today? Why does Elad believe many people will lose a lot of money in them? What advice does Elad give to founders when they are an option? Does Elad believe the lack of liquidity is good for venture this cycle? How does Elad assess the emergence of megafunds? How does this alter and distort the market?

4.) With regards to market share, how should founders prioritise between pricing and market share? Is cash ever a defensible moat? What does Elad mean when he says that “too many people are stuck on Amazon as the winning model”? Why does Elad believe that margins and capital leverage are the unsung heroes of tech?

5.) Why does Elad believe we have seen such a reduction in M&A? Why do many founders not fully assess the financial benefits of being bought by a high growth startup?  What are the big questions founders should ask when an M&A opportunity does arise? What does Elad believe are the reasons to avoid IPOing? What are the inherent benefits of going public?

Items Mentioned In Today’s Show:

Elad’s Fave Book: Ben Horowitz, Andy Grove

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

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

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

Whether you’re starting your own small business or getting serious about making your small business more efficient, you need to invite FreshBooks to the table. FreshBooks makes cloud accounting software that’s so ridiculously easy to use and you’ll quickly understand why over 10 million people use it to radically streamline how they deal with their admin and paperwork. Plus, FreshBooks can handle a lot more than accounting related tasks. Using FreshBooks is kind of like having your own admin assistant who’s got your back, 24/7. To claim your 30-day unrestricted free trial, click here enter Twenty Minute VC in the “how did you hear about us section”.

Highfive makes meetings better for thousands of organizations with insanely simple video conferencing designed for meeting rooms. It’s the easiest-to-use solution, with all-in-one hardware and intuitive cloud software. Plus, it’s a high-quality experience with industry-leading audio powered by Dolby Voice. It’s so easy to use, that there’s no pin codes or app downloads. Just click a link in your browser, and you’re in the meeting. With customers in over 100 countries, Highfive is already trusted by the likes of Evernote, Expensify, and Betterment and you can learn more by simply heading over to highfive.com.

Rachel Blumenthal is the Founder & CEO @ Rockets of Awesome, the startup that is reinventing the way parents shop for their kids clothes. To date, Rachel has raised over $19m in VC funding from the likes of Kirsten Green @ Forerunner, August Capital, General Catalyst, Gwyneth Paltrow and Female Founders Fund to name a few. Prior to Rockets of Awesome, Rachel founded fashion jewelry brand, Rachel Leigh. Rachel scaled the business to being available in over 300 stores worldwide and being named one of Oprah’s “Favourite Things”. Before that Rachel began her career in the publicity department at Yves Saint Lauren.

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In Today’s Episode You Will Learn:

1.) How Rachel went from founding a company that created one of Oprah’s “favourite things” to reinventing the way parents shop for their children today?

2.) Why does Rachel believe that “fundraising is like dating”? What does Rachel mean when she says “you have to play the game”? What does this literally look like in practice? What works in generating investor interest? What does not? Where does Rachel see many make mistakes in the fundraising process?

3.) How does Rachel think about capital efficiency with the evolution of her business? What tips and suggestions does Rachel give to increasing burn flexibility when future growth is ambiguous? Why does Rachel disagree with the thesis of raise money when you don’t need it? What length of time does Rachel believe is the right time to raise for?

4.) Rachel has said before that, “the best investors are operators”. What makes Rachel believe this? What are the drawbacks to operator VCs? What are the benefits to non-operator investors? What makes the truly special investor? How can a founder stress test this prior to their investment? What advice would Rachel give to a non-operator VC to improve their empathy and experience with founders?

5.) Rachel previous sly said to me that “being a woman in this male-dominated environment is everything the stereotype suggests”, what moment or story particularly resonates for Rachel when saying this? How did she respond? How can less confident first time minority founders respond in these situations?

Items Mentioned In Today’s Show:

Rachel’s Fave Book: Fast Company, Inc

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

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

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

Whether you’re starting your own small business or getting serious about making your small business more efficient, you need to invite FreshBooks to the table. FreshBooks makes cloud accounting software that’s so ridiculously easy to use and you’ll quickly understand why over 10 million people use it to radically streamline how they deal with their admin and paperwork. Plus, FreshBooks can handle a lot more than accounting related tasks. Using FreshBooks is kind of like having your own admin assistant who’s got your back, 24/7. To claim your 30-day unrestricted free trial, click here enter Twenty Minute VC in the “how did you hear about us section”.

Highfive makes meetings better for thousands of organizations with insanely simple video conferencing designed for meeting rooms. It’s the easiest-to-use solution, with all-in-one hardware and intuitive cloud software. Plus, it’s a high-quality experience with industry-leading audio powered by Dolby Voice. It’s so easy to use, that there’s no pin codes or app downloads. Just click a link in your browser, and you’re in the meeting. With customers in over 100 countries, Highfive is already trusted by the likes of Warby Parker, Evernote, Expensify, and Betterment and you can learn more by simply heading over to highfive.com.

Pete Flint is a Managing Partner @ NFX, one of Silicon Valley’s newest and most exciting funds with the recent announcement of their new $150m fund late last year. Prior to VC, Pete was a serial entrepreneur building one of today’s most successful marketplaces, as the co-founder of Trulia. Pete led the company from inception to more than 50 million monthly unique users, $250m in VC funding from the likes of Sequoia and Accel culminating in their merger with Zillow in 2015 that valued Trulia at $3.5 billion. Before Trulia, Pete was part of the founding team of lastminute.com, a leading European online travel site that was acquired in 2005 for over $1 billion.

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In Today’s Episode You Will Learn:

1.) How Pete made his way into the world of startups joining the founding team of lastminute.com and how that led to the founding of Trulia and entry into VC?

2.) Why does Pete believe that startup timing is so crucial? How does Pete analyze market timing risk when investing? What is the right way for investors to think about the innovation cycle we are in today? On review, what does Pete believe lastminute.com did most right? What would he most want to change?

3.) What are the leading indicators that suggest potential in a network effect business? Would Pete agree with Josh @ Jackson Square that not all GMV is created equal? How does Pete analyse the lack of free and open distribution today and how that affects marketplace scaling? Why does Pete still believe marketplaces are some of the most capital efficient businesses to grow?

4.) What has been Pete’s greatest time of failure in his career? What is the framework Pete uses to analyze and assess his own ego? What are the commonalities in how Pete has seen truly great founders overcome failure? How does Pete balance between realism when something is not working and the mission and vision of the founder?

5.) How does Pete think about optimizing decision-making, both in investing and operating? How does Pete approach the balance of head vs heart? When is the right time to decide with your head? When is the right time to decide with your heart? Why does Pete argue early-stage investing must be decided with your heart?

Items Mentioned In Today’s Show:

Pete’s Fave Book: Leonardo Da Vinci 

Pete’s Most Recent Investment: Ribbon

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

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

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

Whether you’re starting your own small business or getting serious about making your small business more efficient, you need to invite FreshBooks to the table. FreshBooks makes cloud accounting software that’s so ridiculously easy to use and you’ll quickly understand why over 10 million people use it to radically streamline how they deal with their admin and paperwork. Plus, FreshBooks can handle a lot more than accounting related tasks. Using FreshBooks is kind of like having your own admin assistant who’s got your back, 24/7. To claim your 30-day unrestricted free trial, click here enter Twenty Minute VC in the “how did you hear about us section”.

Highfive makes meetings better for thousands of organizations with insanely simple video conferencing designed for meeting rooms. It’s the easiest-to-use solution, with all-in-one hardware and intuitive cloud software. Plus, it’s a high-quality experience with industry-leading audio powered by Dolby Voice. It’s so easy to use, that there’s no pin codes or app downloads. Just click a link in your browser, and you’re in the meeting. With customers in over 100 countries, Highfive is already trusted by the likes of Evernote, Expensify, and Betterment and you can learn more by simply heading over to highfive.com.

Joe Fernandez is the Founder & CEO @ JoyMode, the startup that allows you to lend everything you need to have the experiences you want. To date, Joe has raised over $16m in funding for Joymode from friends of the show including Homebrew, Slow Ventures, Founder Collective, Scott Belsky, Collaborative Fund and Lowercase, just to name a few. As for Joe, prior to founding JoyMode, Joe founded Klout, one of the leading social media analytics platforms of the day and raised $40m in funding from Kleiner Perkins, IVP, Venrock, Greycroft and more. Klout was ultimately acquired by Lithium Technologies where Joe sits on the board.

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In Today’s Episode You Will Learn:

1.) How Joe made his way into the world of startups with the founding of Klout? Given his entrepreneurial start, would Joe say he is unemployable?

2.) Question from Craig Shapiro: What was your single greatest lesson from the Klout journey? How has that impacted how you operate JoyMode today? How has Joe approached fundraising fundamentally differently today than with Klout? How is Joe’s team building strategy today different to his with Klout?

3.) Why does Joe believe that “serial entrepreneurs are over-rated”? What does Joe mean when he says, “you have to know which hill you are willing to die on”? How does Joe look to accurately ego check today? What innovative methods does Joe employ internally to ensure that his views are validated and not submitted to?

4.) What does Joe mean when he says, “you have to make big bets to win”? How can you implement this risk-taking mentality in larger teams? What is the right way for both the team and investor base to respond? How does Joe use continuous iteration and data-centricity to test and validate these theses?

5.) How does Joe approach investor update emails? Why does Joe look to terrify investors with each update? Does Joe believe that it is right to thanks specific individuals in those emails? Does like like to select individuals and request their help in the emails? How can past updates be used to attain future investors?

Items Mentioned In Today’s Show:

Joe’s Fave Book: The Accidental Superpower

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

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

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

Whether you’re starting your own small business or getting serious about making your small business more efficient, you need to invite FreshBooks to the table. FreshBooks makes cloud accounting software that’s so ridiculously easy to use and you’ll quickly understand why over 10 million people use it to radically streamline how they deal with their admin and paperwork. Plus, FreshBooks can handle a lot more than accounting related tasks. Using FreshBooks is kind of like having your own admin assistant who’s got your back, 24/7. To claim your 30-day unrestricted free trial, click here enter Twenty Minute VC in the “how did you hear about us section”.

Highfive makes meetings better for thousands of organizations with insanely simple video conferencing designed for meeting rooms. It’s the easiest-to-use solution, with all-in-one hardware and intuitive cloud software. Plus, it’s a high-quality experience with industry-leading audio powered by Dolby Voice. It’s so easy to use, that there’s no pin codes or app downloads. Just click a link in your browser, and you’re in the meeting. With customers in over 100 countries, Highfive is already trusted by the likes of Warby Parker, Evernote, Expensify, and Betterment and you can learn more by simply heading over to highfive.com.

 

Joel Monegro is Founding Partner @ Placeholder.VC, one of the new venture capital partnerships that invest solely in crypto assets and more specifically in decentralized information networks. Prior to founding Placeholder, Joel spent three years at Union Square Ventures developing the firm’s blockchain investment thesis and portfolio. Before USV, Joel started the Digital Economy Department at the Ministry of Industry and Commerce of the Dominican Republic, a government office in charge of developing the country’s national and technology agenda.

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In Today’s Episode You Will Learn:

1.) How Joel made his way into the world of VC with USV and what created his love of crypto and led to his leaving USV to found Placeholder? What were some of Joel’s biggest investing lessons from his time with USV?

2.) How does Joel approach portfolio construction in building out a crypto portfolio? How does the use of reserves and building positions change when comparing VC to crypto? Why does Joel believe that the most interesting place to invest in crypto is in the assets themselves, rather than the companies?

3.) When does Joel think we will see institutional capital begin to move into the space in a meaningful way? What needs to happen/change for this institutional interest to materialize? How is the element of “custody” crucial to the entrance of institutions?

4.) In terms of fund construction, liquidity is often an attractive element to crypto, why does Joel believe that a traditional venture fund structure is necessary for Placeholder? What are the benefits both to the fund and the projects it backs? How do LPs both traditional and non-traditional respond to this?

5.) Joel has said before the 2 core elements are crypto economics and governance, why does Josh believe this? Why is governance the foundational layer where value will accrue in the space? How does the lack of defensibility of crypto projects make governance ever more valuable?

Items Mentioned In Today’s Show:

Joel’s Fave Book: Antifragile by Nassim Taleb

Joel’s Most Recent Investment: Decred Investment Thesis

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

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

Whether you’re starting your own small business or getting serious about making your small business more efficient, you need to invite FreshBooks to the table. FreshBooks makes cloud accounting software that’s so ridiculously easy to use and you’ll quickly understand why over 10 million people use it to radically streamline how they deal with their admin and paperwork. Plus, FreshBooks can handle a lot more than accounting related tasks. Using FreshBooks is kind of like having your own admin assistant who’s got your back, 24/7. To claim your 30-day unrestricted free trial, click here enter Twenty Minute VC in the “how did you hear about us section”.

Highfive makes meetings better for thousands of organizations with insanely simple video conferencing designed for meeting rooms. It’s the easiest-to-use solution, with all-in-one hardware and intuitive cloud software. Plus, it’s a high-quality experience with industry-leading audio powered by Dolby Voice. It’s so easy to use, that there’s no pin codes or app downloads. Just click a link in your browser, and you’re in the meeting. With customers in over 100 countries, Highfive is already trusted by the likes of Evernote, Expensify, and Betterment and you can learn more by simply heading over to highfive.com.

 

Max Motschwiller is a Partner with Meritech Capital, one of the West Coast’s leading growth investment firms with over $150Bn in IPOs and a portfolio that includes the likes of Facebook, Salesforce, Snap, Box, Mulesoft and Cloudera just to name a few. As for Max, prior to Meritech he spent 3 years with Kleiner Perkins (KPCB) where he was actively involved with investments in Dropcam (Nest/Google), Duolingo, MyFitnessPal (Under Armour), RelateIQ (Salesforce.com) and Stance. Before joining KPCB, Max worked for 3 years at Summit Partners and was actively involved across Summit’s technology portfolio.

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In Today’s Episode You Will Learn:

1.) How did Max make his way into the world of VC with Summit and KP from University? What did that decision-making process look like for Max?

2.) As a career VC, would Max agree with Pat Grady @ Sequoia, “the rate of decay on operating experience has never been greater”? What would Max say are the biggest elements he missed through lack of operational experience? How do the skills required from early to pre-IPO change the type of background required?

3.) Max has said before, “to be a good VC you have to do 4 things well”, what are those 4 things? Why does Max believe that picking is the greatest skill to develop? At growth, what does Max mean when he says “the picking is around price”? How do the very best VCs approach price sensitivity?

4.) Question from Rob Ward: Max has mastered network development from an early age, what advice would Max give with regards to developing a network? What did he do well and works? What did he try and did not do well? How does Max think about depth vs breadth of network? How does he apply this to investing and due diligence?

5.) In a time of Softbank and Sequoia’s $7Bn fund, how does a firm like Meritech look to compete in such frothy environments? How has growth bifurcated into 2 clear stages? What are the advantages of being a small pure-play growth firm? How does the portfolio construction and return expectation change for you given the fund size and stage of investment?

Items Mentioned In Today’s Show:

Max’s Fave Book: Home Deus

Max’s Most Recent Investment: Amplitude

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

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

Whether you’re starting your own small business or getting serious about making your small business more efficient, you need to invite FreshBooks to the table. FreshBooks makes cloud accounting software that’s so ridiculously easy to use and you’ll quickly understand why over 10 million people use it to radically streamline how they deal with their admin and paperwork. Plus, FreshBooks can handle a lot more than accounting related tasks. Using FreshBooks is kind of like having your own admin assistant who’s got your back, 24/7. To claim your 30-day unrestricted free trial, click here enter Twenty Minute VC in the “how did you hear about us section”.

Highfive makes meetings better for thousands of organizations with insanely simple video conferencing designed for meeting rooms. It’s the easiest-to-use solution, with all-in-one hardware and intuitive cloud software. Plus, it’s a high-quality experience with industry-leading audio powered by Dolby Voice. It’s so easy to use, that there’s no pin codes or app downloads. Just click a link in your browser, and you’re in the meeting. With customers in over 100 countries, Highfive is already trusted by the likes of Evernote, Expensify, and Betterment and you can learn more by simply heading over to highfive.com.

Hemant Taneja is Managing Director @ General Catalyst, one of the world’s leading venture firms of the last decade with Airbnb, Stripe, Snapchat, Hubspot and Gusto all in their portfolio. As for Hemant, he has led investments at GC in Stripe, SNAP, Grammarly, Gusto, Livongo, Color Genomics, Class Dojo and more. He also directs the GC Stripe Platform Fund, a $10 million initiative to help start new ventures that are built on top of the Stripe Connect platform. On the educational front, Hemant holds 5 degrees from MIT and sits on the board of Khan Academy.

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In Today’s Episode You Will Learn:

1.) How Hemant made his way from 5 degrees at MIT and wanting to be an academic to pursuing startups in the world of VC with General Catalyst?

2.) Question from Sam @ ClassDojo: What were the hardest elements of establishing GC on the West Coast? With hindsight today, what would Hemant do differently given the chance? How does Hemant think about the development and ability to accelerate the creation of local reputation? What is crucial and works most effectively?

3.) How does Hemant respond to Elad Gil’s “everyone is looking for the next truly deep dein to explore”? Why is Hemant so bullish that we are in the “golden age of venture capital”? Why does Hemant believe that “scale” as a key measure has run it’s course? What does Hemant’s thesis of the future of “unscaling” really mean?

4.) How does Hemant analyse price sensitivity in todays forthy environment? How has his relationship to price changed over time? With regards to price, what have been some of his biggest regrets and learnings drawn from real-world examples? How does Hemant assess reserve allocation? Why does he think pro-rata is a lazy posture?

5.) Hemant has said on boards for over 1,800 hours, so what does Hemant belive makes the truly special board members? How does Hemant think about first building that rapport and “intimacy” with the founder? Secondly, how important does Hemant believe it is to build similar relations with other board members? Which founder exemplifies the best board management in Hemant’s mind?

Items Mentioned In Today’s Show:

Hemant’s Fave Book: Home Deus

Hemant’s Most Recent Investment: Spring Discovery

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

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

Highfive makes meetings better for thousands of organizations with insanely simple video conferencing designed for meeting rooms. It’s the easiest-to-use solution, with all-in-one hardware and intuitive cloud software. Plus, it’s a high-quality experience with industry-leading audio powered by Dolby Voice. It’s so easy to use, that there’s no pin codes or app downloads. Just click a link in your browser, and you’re in the meeting. With customers in over 100 countries, Highfive is already trusted by the likes of Evernote, Expensify, and Betterment and you can learn more by simply heading over to highfive.com.

Culture Amp is the platform that makes it easy to collect, understand and act on employee feedback. From onboarding surveys to company-wide engagement, individual effectiveness and more, the platform manages multiple sources of feedback and connects the dots for you and that is why companies like Slack, Nike, Oracle and Lyft all trust Culture Amp. It enables leaders to make better decisions, demonstrate impact and turn your company culture into a competitive edge.  So put your people and culture first and find out more on cultureamp.com.

Amanda Bradford is the Founder & CEO @ The League, the exclusive dating app that wants you to spend your time a little more intelligently when it comes to finding the perfect match online. They have raised funding from the likes of Aileen Lee @ Cowboy Ventures, Sherpa Ventures and Alex Rosen @ Ridge Ventures just to name a few. Prior to founding The League, Amanda spent time at Evernote as a Product Manager, as an investor with Sequoia Capital and started her career in the strategic partnerships team at Google.

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In Today’s Episode You Will Learn:

1.) How Amanda made her way into the world of startups and how she came to want to change the world of dating with The League?

2.) Why does Amanda totally disagree with the conventional wisdom that you cannot be a single founder? What are the benefits of being a single founder? How has Amanda used this to incentivize her team further? What are the core challenges that remain in being a single founder? What 2 reasons does Amanda feel 90% of startups fail?

3.) What does Amanda really mean when she says about “the art of the launch”? How can founders pre-game their launch to have existing users on day 1? What benchmarks does Amanda set when launching a new product, to determine the success of the launch? How core is the 7-day retention number to Amanda in her metric stack?

4.) How does Amanda think about the right time to turn on monetization? How can founders determine the level of consumer appetite for premium products, pre-developing them? What are the main challenges when turning on monetization? How does monetization affect investor appetite?

5.) Amanda has raised from Cowboy, Sherpa, Ridge, how was the fundraising process for Amanda? Why did Amanda choose to pursue the party round approach at seed? What are the core benefits of doing so? Has the lack of lead investor meant a reduced willingness to help from the investor base?

Items Mentioned In Today’s Show:

Amanda’s Fave Book: The Giver

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

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

Highfive makes meetings better for thousands of organizations with insanely simple video conferencing designed for meeting rooms. It’s the easiest-to-use solution, with all-in-one hardware and intuitive cloud software. Plus, it’s a high-quality experience with industry-leading audio powered by Dolby Voice. It’s so easy to use, that there’s no pin codes or app downloads. Just click a link in your browser, and you’re in the meeting. With customers in over 100 countries, Highfive is already trusted by the likes of Warby Parker, Evernote, Expensify, and Betterment and you can learn more by simply heading over to highfive.com.

Culture Amp is the platform that makes it easy to collect, understand and act on employee feedback. From onboarding surveys to company-wide engagement, individual effectiveness and more, the platform manages multiple sources of feedback and connects the dots for you and that is why companies like Slack, Nike, Oracle and Lyft all trust CultureAmp. So put your people and culture first and find out more on cultureamp.com.

Peter Parker is the Managing Partner @ BioInnovation Capital, the $130m fund transforming life science investing through backing companies based in shared laboratories in Cambridge, San Francisco, San Diego, Durham, and NYC. For the past three decades, Peter has devoted his life to venture and startups, starting in 1986 with his establishing Ampersand Ventures life sciences platform which he managed until 2006. During this period he was the first institutional capital and a Director to over 2 dozen life sciences startups and enjoyed more exits than I have done podcasts. He is also a co-founder of LabCentral, Inc, a not-for-profit shared facility for companies who need biolab space enables more than 75 companies to pursue their biotech start-up ambitions.

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In Today’s Episode You Will Learn:

1.) How Peter made his way into what was a very different VC industry back in 1986?

2.) Peter has seen the venture ecosystem develop enormously over the last 30 years, what have been the biggest changes and transformations? What are both the most positive and negative changes to hit venture? How has specialization changed the investing game? What would Peter like to change about the world of VC today?

3.) What does Peter mean when he says the best VCs understand the importance of process? What is the right way to construct your process in VC? How does this affect Peter’s thinking on functioning partnerships in venture? What can one do to optimise the quality of those relationships and conversations with partners?

4.) Peter has chaired over 25 boards over the last 32 years in VC, how has Peter seen his style of board membership fundamentally change over that time? What have been the inflection points in his learning? How do OKRs play a crucial role in how he drives board operations? How has Peter approached removing the CEO? What is the right way to do it?

5.) Peter’s most recent fund is a $130m seed fund, how was the latest fundraise for Peter? What drives Peter’s passion and enthusiasm for fundraising and LP communications? What makes the best LP meetings for Peter? How has Peter seen his presentation style to LPs change over time? What has Peter learned is crucial for LP conversion?

Items Mentioned In Today’s Show:

Peter’s Fave Book: The Barbarian: A Surfing Life

Peter’s Most Recent Investment: Graphwear

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.

Highfive makes meetings better for thousands of organizations with insanely simple video conferencing designed for meeting rooms. It’s the easiest-to-use solution, with all-in-one hardware and intuitive cloud software. Plus, it’s a high-quality experience with industry-leading audio powered by Dolby Voice. It’s so easy to use, that there’s no pin codes or app downloads. Just click a link in your browser, and you’re in the meeting. With customers in over 100 countries, Highfive is already trusted by the likes of Warby Parker, Evernote, Expensify, and Betterment and you can learn more by simply heading over to highfive.com.

Culture Amp is the platform that makes it easy to collect, understand and act on employee feedback. From onboarding surveys to company-wide engagement, individual effectiveness and more, the platform manages multiple sources of feedback and connects the dots for you and that is why companies like Slack, Nike, Oracle and Lyft all trust Culture Amp. It enables leaders to make better decisions, demonstrate impact and turn your company culture into a competitive edge.  So put your people and culture first and find out more on cultureamp.com.

Paul English is the Co-Founder of both Lola and Kayak. Starting on Lola, the company brings joy to business travelers by finding the best flights for busy schedules and perfect hotels that suit personal preferences. To date, Paul has raised over $44m with Lola from the likes of CRV, Accel, General Catalyst and GV just to name a few. Prior to Lola, Paul co-founded Kayak, the incredible success story that helps millions of travelers make confident travel decisions. Prior to their IPO, Paul raised over $229m in VC funding from Sequoia, Accel, IVP and General Catalyst before their reported $1.8Bn acquisition by Priceline. Paul is also a prolific philanthropist and due to his success has had much press attention including the Tracy Kidder book, A Truck Full of Money.

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In Today’s Episode You Will Learn:

1.) How Paul made his way into the world of startups from having his first taste of entrepreneurship buying and refurbishing air conditioning units?

2.) Paul is behind many groundbreaking ideas of the last decade, so what does the idea generation process look like for Paul? How does Paul determine between a good and a great idea? How has this process changed over time? How does Paul pull other individuals into validating ideas or not?

3.) Paul’s VCs stated “Paul is the best founder in the world for hiring”, how does Paul approach team building? What does Paul think is required to attract truly world calls talent? Can this skill be taught? Where does Paul believe so many founders go wrong in recruitment? What does Paul mean when he says you want to see “arrogant humility”

4.) Having raised from Sequoia, GV, General Catalyst and more, what has Paul found to really encapsulate the truly special VCs? What are Paul’s lessons on raising the highest quality capital possible? When is the right time to optimize for valuation and when is it not? What made Mike Moritz and Joel Cutler so special to work with on Kayak?

5.) How does Paul approach the aspect of board management? How has this changed over time for him? What relationship should founders desire with their VCs and then between the VCs themselves? How does one look to optimise for efficiency in board conversations? How does Paul look to handle board disputes?

Items Mentioned In Today’s Show:

Paul’s Fave Book: The Trumpet of Conscience

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

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

Highfive makes meetings better for thousands of organizations with insanely simple video conferencing designed for meeting rooms. It’s the easiest-to-use solution, with all-in-one hardware and intuitive cloud software. Plus, it’s a high-quality experience with industry-leading audio powered by Dolby Voice. It’s so easy to use, that there’s no pin codes or app downloads. Just click a link in your browser, and you’re in the meeting. With customers in over 100 countries, Highfive is already trusted by the likes of Warby Parker, Evernote, Expensify, and Betterment and you can learn more by simply heading over to highfive.com.

Culture Amp is the platform that makes it easy to collect, understand and act on employee feedback. From onboarding surveys to company-wide engagement, individual effectiveness and more, the platform manages multiple sources of feedback and connects the dots for you and that is why companies like Slack, Nike, Oracle and Lyft all trust CultureAmp. So put your people and culture first and find out more on cultureamp.com.

Trae Vassallo is the Co-Founder and Managing Director @ Defy.VC, one of Silicon Valley’s newest and most exciting Series A funds with the announcement of their debut $151m fund in Sept 2017. Prior to co-founding Defy, Trae was a general partner at Kleiner Perkins Caufield & Byers where she invested in a number of leading companies including eero, Nest Labs, Dropcam, Aggregate Knowledge, and Opower. Before Kleiner, Trae founded Kleiner portfolio company, Good Technology which was ultimately acquired by Blackberry in 2015 for $425m. Trae is also the co-author of the incredible study, “Elephant in the Valley”, highlighting the underlying data around the experiences of women in technology.

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In Today’s Episode You Will Learn:

1.) How Trae made her way into the world of VC and Silicon Valley with a cold reach out to John Doerr and how that led to a role with Kleiner Perkins?

2.) What were Trae’s biggest learnings from having John Doerr on her board, as a first-time founder? What were some of the most memorable moments working with him? What was it about him that made him such a special board member? What was the moment that Trae realized what type of board member she is?

3.) What does Trae mean when she says “Kleiner taught me what a great investment looks like”? How does that affect her investing philosophy today? How did Trae’s investing learnings differ between John Doerr, Vinod Khosla, and Kevin Compton?

4.) Why does Trae believe that the venture industry is simply “overfunded”? If so, what was her reasoning for the founding of Defy? How does Trae see the expansion of multi-stage funds as presenting a market opportunity? Why are the larger players no longer incentivized to play at the Series A stage?

5.) How did Trae find the fundraising process? What were some of the core challenges in terms of the raise itself? Were there commonalities in the pushbacks that LPs had for Defy? How did Neil and Trae respond to the first time team question? How does Trae think about the infrastructure element of funds? Can it all be outsourced?

Items Mentioned In Today’s Show:

Trae’s Fave Book: Brotopia: Breaking Up the Boys’ Club of Silicon Valley

Trae’s Most Recent Investment: Owl Car Cam: The First Security Camera For Your Car

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

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

Highfive makes meetings better for thousands of organizations with insanely simple video conferencing designed for meeting rooms. It’s the easiest-to-use solution, with all-in-one hardware and intuitive cloud software. Plus, it’s a high-quality experience with industry-leading audio powered by Dolby Voice. It’s so easy to use, that there’s no pin codes or app downloads. Just click a link in your browser, and you’re in the meeting. With customers in over 100 countries, Highfive is already trusted by the likes of Warby Parker, Evernote, Expensify, and Betterment and you can learn more by simply heading over to highfive.com.

Culture Amp is the platform that makes it easy to collect, understand and act on employee feedback. From onboarding surveys to company-wide engagement, individual effectiveness and more, the platform manages multiple sources of feedback and connects the dots for you and that is why companies like Slack, Nike, Oracle and Lyft all trust CultureAmp. So put your people and culture first and find out more on cultureamp.com.

Jack Groetzinger is the Founder & CEO @ SeatGeek, the world’s largest ticket inventory on the web serving more than 500,000 artists and teams in over 380,000 venues. To date, Jack has raised over $160m in VC funding with SeatGeek from the likes of John Locke @ Accel, Founder Collective, TCV and most recently a $57m Series D led by Glynn Capital Management. Prior to SeatGeek, Jack founded Scribnia, a web app that used collaborative filtering to recommend bloggers and blog content, sold to an ad network in 2009. Jack is also a Founder Partner @ Founder Collective and angel investor in Troops, Inc.

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In Today’s Episode You Will Learn:

1.) How Jack made his way into the world of startups and decided to reinvent the ticketing industry with SeatGeek?

2.) How does Jack think about the combination of technical vs commercial skills for founders today? Where has Jack struggled with this balance? What would his advice be to prospective founders? How does Jack use OKRs to drive efficiency at SeatGeek? How can OKRs be constructed the right way? What is a rate of failure that suggests you are being ambitious enough?

3.) Jack has raised multiple rounds and over $160m in funding, how have the rounds differed from round to round? How does what Jack wants from an investor differ with time? What one ability do truly unique board members have the ability to do? How does Jack think about board conflicts and the right way to communicate with boards?

4.) How does Jack determine when is the right time to raise big? What is the one core metric that says now is the right time? How does Jack think about both the diversification and mortality of customer acquisition channels? How have SeatGeek seen theirs fundamentally change over time?

5.) Jack led the $56m Toptix acquisition, how was the acquisition process for Jack? What were the big learnings for Jack in terms of buying something that is large? With the acquisition, how does Jack think about the balance between capital efficiency and aggressive growth? What would Jack have done differently with regards to their growth trajectory if he had his time again?

Items Mentioned In Today’s Show:

Jack’s Fave Book: Powerful: Building a Culture of Freedom and Responsibility

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

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

Highfive makes meetings better for thousands of organizations with insanely simple video conferencing designed for meeting rooms. It’s the easiest-to-use solution, with all-in-one hardware and intuitive cloud software. Plus, it’s a high-quality experience with industry-leading audio powered by Dolby Voice. It’s so easy to use, that there’s no pin codes or app downloads. Just click a link in your browser, and you’re in the meeting. With customers in over 100 countries, Highfive is already trusted by the likes of Warby Parker, Evernote, Expensify, and Betterment and you can learn more by simply heading over to highfive.com.

Culture Amp is the platform that makes it easy to collect, understand and act on employee feedback. From onboarding surveys to company-wide engagement, individual effectiveness and more, the platform manages multiple sources of feedback and connects the dots for you and that is why companies like Slack, Nike, Oracle and Lyft all trust CultureAmp. So put your people and culture first and find out more on cultureamp.com.

Glenn Solomon is a Managing Partner @ GGV Capital, one of the world’s leading venture funds with  $3.8Bn under management across 8 funds and a portfolio including the likes of Airbnb, Xiaomi, Alibaba, Slack, Square, the list goes on. As for Glenn, since joining GGV in 2005 Glenn has helped 7 companies go public including Pandora, Zendesk, Square, SuccessFactors and more and has led investments in Airbnb, Slack, Opendoor, DOMO and Hashicorp just to name a few. Prior to GGV, Glenn was a General Partner with Partech and before that spent time with Goldman Sachs. You must also check out Glenn’s blog here.

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In Today’s Episode You Will Learn:

1.) How Glenn made his way from tennis at Stanford to the walls of Goldman Sachs before entering the world of VC with Partech and then GGV?

2.) Having been in VC for over 20 years, how has Glenn fundamentally seen the startup and VC landscape alter? How did advice from John Doerr alter his thinking on platform shifts? Does Glenn agree with Elad Gil that we are all looking for the next vein of innovation to explore? How must VCs respond?

3.) How has Glenn seen the development of himself as an investor over the last 20 years? What has he found to be the commonalities amongst the very best VCs? How does Glenn think about the importance of investor specialisation?

4.) How does Glenn think about price sensitivity? When has Glenn made his biggest mistakes with regards to price? How does Glenn’s opinions change with the differing insertion points from Series A to pre-IPO?

5.) What does Glenn believe makes the truly special board members? What does he mean when he says being on a board is a “full contact” sport? What are the foundational pillars that Glenn has learnt make the most productive and successful board meetings? What can both founders and VCs do to drive efficiency from their time in board meetings?

Items Mentioned In Today’s Show:

Glenn’s Fave Book: Shoe Dog, Born A Crime, Irena’s Children

Glenn’s Most Recent Investment: Unravel Data

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

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

Highfive makes meetings better for thousands of organizations with insanely simple video conferencing designed for meeting rooms. It’s the easiest-to-use solution, with all-in-one hardware and intuitive cloud software. Plus, it’s a high-quality experience with industry-leading audio powered by Dolby Voice. It’s so easy to use, that there’s no pin codes or app downloads. Just click a link in your browser, and you’re in the meeting. With customers in over 100 countries, Highfive is already trusted by the likes of Warby Parker, Evernote, Expensify, and Betterment and you can learn more by simply heading over to highfive.com.

Culture Amp is the platform that makes it easy to collect, understand and act on employee feedback. From onboarding surveys to company-wide engagement, individual effectiveness and more, the platform manages multiple sources of feedback and connects the dots for you and that is why companies like Slack, Nike, Oracle and Lyft all trust CultureAmp. So put your people and culture first and find out more on cultureamp.com.

Adrian Aoun is the Founder & CEO @ Forward, a health care system combining world-class doctors with advanced technology to empower patients to take control of their health. To date Adrian has raised funding from some of the true greats of the business including Marc Benioff, Eric Schmidt, Joe Lonsdale, Aaron Levie and Josh Kushner, to name a few. As a result of the incredible work at Forward, they were named to TIME’s Best Inventions of 2017. Before Forward, Adrian was the head of special projects for the CEO of Google/Alphabet and Adrian arrived at Google following the acquisition of his artificial intelligence (AI) company, Wavii. Adrian is also a prolific angel with the likes of WorkRamp, Atrium, Convoy and more in his incredible portfolio.

Dan Scheinman is one of the West Coast’s leading angel investors with a portfolio including the likes of Zoom.us, Tango.me, TomFoolery (acquired by Yahoo) and Arista Networks, where he also sits on the board. Prior to angel investing, Dan spent 18 years at Cisco in numerous roles including Senior Vice President of Corporate Development where he rebuilt corp dev as a growth enabler for Cisco. Dan was also the Senior Vice President and General Manager of the Cisco Media Solutions Group (CMSG), an internal startup which successfully developed and marketed a hosted software.

Seth Sternberg is the Founder & CEO @ Honor, the startup that provides homecare your family will love. To date Seth has raised over $60m in funding with Honor from the likes of Thrive Capital, a16z, Homebrew and 8VC. Prior to Honor, Seth was the Co-founder & CEO of Meebo, a web communications platform backed by the likes of Sequoia, Khosla and True Ventures. Meebo reached $50M in revenue and close to half of the US internet population before being acquired by Google for $100M in 2012. At Google, Seth became a Product Director working on the Google+ Platform and GoogleX. Seth is also a prolific angel investor with a portfolio including the likes of Fitbit and Gusto to name a few.

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In Today’s Episode You Will Learn:

1.) How Seth made his way into the world of startups with the founding of Sequoia backed, Meebo? How did he transition from social network to homecare provision?

2.) From his experience with Meebo, what are the biggest elements Seth has done differently with the building of Honor? What was successful the first time that he has carried with him to Honor? How does Seth approach the hiring process fundamentally differently the 2nd time around?

3.) Seth has worked with the likes of Sequoia, Khosla, Thrive and more, what are the commonalities that make the best VCs so special? Where does Seth believe VCs can add true value? Where do many seriously detract value? Why does Seth believe that 80% of VCs are actually detrimental to board meetings?

4.) What 3 questions must all founders ask when considering to take on a new investor? What is that investor-founder assessment structure? When there is a disagreement with investors, how does Seth approach this? What is the best method for doing this in as fast and efficient method as possible?

5.) Would Seth agree with David Barrett @ Expensify that we are going through a wave of founders creating companies for the quick flip? How does Seth’s 20-year time horizon with Honor affect how he both thinks about hiring and individual scaling within the firm? Why is he so jealous of Google and Facebook with regards to this?

Items Mentioned In Today’s Show:

Seth’s Fave Book: The Firm

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

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

We also speak about Movidiam – as brands turn to smarter ways of creating video and digital content, the Movidiam platform offers faster turnarounds whilst maintaining or improving quality. They’re already working with some of the biggest, most innovative companies to help compare teams and freelancers across the global curated network of creative talent. Producers and marketers looking for the best creatives can get a shortlist from Movidiam’s account managers in hours – tailored to their project’s needs. Submit a brief or check out the platform at Movidiam.com.

Boris Wertz is the Founding Partner @ Version One Ventures, one of North America’s leading early-stage funds with a portfolio including the likes of previous guests Coinbase, AngelList, Shippo, TopHat, Polychain Capital and many more incredible companies. As for Boris, prior to VC, Boris was the COO @ Abe Books, where he led a team of 60 people until their acquisition in 2008 by Amazon. In addition to this, Boris is also a Board Partner with a16z and the lead independent director @ Ether Capital, a Toronto-based technology company aiming to become the central investment hub for the Ethereum ecosystem.

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In Today’s Episode You Will Learn:

1.) How Boris made his way from creating the largest European marketplace for used books to becoming one of North America’s leading investors with Version One?

2.) How does Boris analyze where we are at now in the development and hype cycle of crypto? How does it compare to the internet bubble of 99′? Does Boris get concerned by the amount of dumb money entering the space? What resources and tools does Boris advice for people looking to learn the foundations as quickly as possible?

3.) Why does Boris believe you have to apply a new mental model when investing in crypto? What do existing VCs need to do to ensure they are not left behind by the emerging world of crypto? What does Boris believe would need to happen for the existing institutional LP class to embrace crypto?

4.) Does Boris believe existing investors can transition into this space or will vertically specialised funds be the clear winner? If existing investors can, what is required within their partnerships to make this happen? What does Boris make of VCs investing in ICOs? How does Boris evaluate the Telegram ICO?

5.) How does Boris view the future of VC in tandem with the world of crypto and ICOs? What would VCs becoming small cap hedge funds mean for the industry? How would life change? What have been Boris’ biggest learnings from watching first hand a16z’s attempts to innovate the VC model at scale?

Items Mentioned In Today’s Show:

Boris’ Fave Book: Shoe Dog

Boris’ Most Recent Investment: Coinbase

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

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

We also speak about Movidiam – as brands turn to smarter ways of creating video and digital content, the Movidiam platform offers faster turnarounds whilst maintaining or improving quality. They’re already working with some of the biggest, most innovative companies to help compare teams and freelancers across the global curated network of creative talent. Producers and marketers looking for the best creatives can get a shortlist from Movidiam’s account managers in hours – tailored to their project’s needs. Submit a brief or check out the platform at Movidiam.com.

Andrew Dudum is Co-Founder & CEO @ Hims, the fastest growing men’s health and wellness brand that has raised over $45m in VC funding from some of the best in the business including Thrive Capital, Forerunner Ventures, IVP, Redpoint and SV angel just to name a few. Andrew is also co-founder and General Partner at Atomic, a venture-builder backed by Peter Thiel, Marc Andreesen and many of the world’s best investors. Prior to Atomic and Hims, Andrew led Product at TokBox.com, the leader in web-based communication. In 2012 TokBox was acquired by the global telecommunications company Telefonica ($TEF).

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In Today’s Episode You Will Learn:

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

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

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

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

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

Items Mentioned In Today’s Show:

Andrew’s Fave Book: Creativity Inc

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

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

We also speak about Movidiam – as brands turn to smarter ways of creating video and digital content, the Movidiam platform offers faster turnarounds whilst maintaining or improving quality. They’re already working with some of the biggest, most innovative companies to help compare teams and freelancers across the global curated network of creative talent. Producers and marketers looking for the best creatives can get a shortlist from Movidiam’s account managers in hours – tailored to their project’s needs. Submit a brief or check out the platform at Movidiam.com.

Andy McLoughlin is Partner @ Uncork Capital, formerly SoftTech and one of the leading early-stage funds on the West Coast. In their incredible portfolio, they have the likes of Fitbit, SendGrid, PostMates, Front, PoshMark, Eventbrite and many more. As for Andy, he loves to invest in “unsexy ideas” with stellar teams and has led deals in the likes of Postmates, LaunchDarkly, Human Interest (previously Captain 401), and Focal Systems just to name a few. Prior to VC, Andy co-founded Huddle, an enterprise collaboration platform which raised more than $80M in venture funding before its acquisition in 2017. Andy also has a stellar angel portfolio with the likes of Buffer, Intercom and Pipedrive all angel investments.

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In Today’s Episode You Will Learn:

1.) How Andy made the transition from Founder of one of the UK’s hottest startups to one of the leading early-stage VCs in Silicon Valley?

2.) Why did Softtech decide to make the big decision to rebrand to Uncork several years into the journey? What is core to successfully relaunching a VC brand to the ecosystem?

3.) Andy likes to back “non-obvious founders” building “non-sexy businesses”. What does Andy mean by “non-obvious founder”? How do they tend to behave differently to more seasoned serial entrepreneur founders from the valley? What does a “non-sexy business look like to Andy”? Why does he see such inherent opportunity within these segments?

4.) How does Andy evaluate the challenge of immensely long sales cycles within these industries? How can these be mitigated and measured against? How does this affect Andy’s thinking on the right amount of runway to raise for? How does Andy assess the often issue of regulation? How does Andy distinguish between viable/ non-viable?

5.) How does Andy assess VC value add? Where does Andy believe he can provide the most value to his portfolio? Why does Andy believe startups are not just competing against other plays in their space but every startup in the valley?

Items Mentioned In Today’s Show:

Andy’s Fave Book: Venture Deals

Andy’s Most Recent Investment: Fritz

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

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

We also speak about Movidiam – as brands turn to smarter ways of creating video and digital content, the Movidiam platform offers faster turnarounds whilst maintaining or improving quality. They’re already working with some of the biggest, most innovative companies to help compare teams and freelancers across the global curated network of creative talent. Producers and marketers looking for the best creatives can get a shortlist from Movidiam’s account managers in hours – tailored to their project’s needs. Submit a brief or check out the platform at Movidiam.com.

Jesse Genet is the Founder & CEO @ Lumi, the startup that is used by thousands of e-commerce companies to get world-class packaging at unbeatable prices. To date, Jesse has raised close to $10m in VC funding from some of the best in the business and old friends of the show including Satya @Homebrew, Kirsten @ Forerunner, Spark Capital, Lowercase, Ludlow and more incredible names. Prior to Lumi, Jesse founded Inkodye, a bootstrapped business that Jesse scaled to 7 figures in revenue and was sold in retail stores around the world.

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In Today’s Episode You Will Learn:

1.) How Jesse made her way into the world of startups and VC having bootstrapped her prior business to 7 figures in revenue and being sold in 1,500 stores?

2.) Given that Lumi is Jesse’s first VC backed business, does this make Jesse a first-time founder? How did the bootstrapping to 7 figures in revenue with her last business, influence her philosophy and mindset with Lumi? What has Jesse done differently as a result? What are the dangers that Jesse was aware of and looks out for?

3.) What types of companies does an active content strategy make significant sense for? What are the core benefits of a well-executed content strategy? What have been the core pillars to Jesse’s success with content? Where does Jesse see many firms going wrong with their content strategy? How does Jesse look to measure the ROI from content?

4.) How was the fundraising experience for Jesse, given the “non-sexy” sector of packaging and supply chains? How did Jesse determine whether an investor was engaged or not? What does Jesse think she did well in the fundraising process? What would she like to improve for the next round? What is the common stereotype that VCs attribute to founders with bootstrapping experience?

5.) How does Jesse think about the benefits of her team being small vs her 10,000+ incumbent challenger teams? Why does this mean she has the advantage? How does Jesse manage the expectations of her employees when no one could do 1/10 of what Jesse does?

Items Mentioned In Today’s Show:

Jesse’s Fave Book: Gone with the Wind

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.

We also speak about Movidiam – as brands turn to smarter ways of creating video and digital content, the Movidiam platform offers faster turnarounds whilst maintaining or improving quality. They’re already working with some of the biggest, most innovative companies to help compare teams and freelancers across the global curated network of creative talent. Producers and marketers looking for the best creatives can get a shortlist from Movidiam’s account managers in hours – tailored to their project’s needs. Submit a brief or check out the platform at Movidiam.com.

Jerry Neumann is one of New York’s leading angel investors with a portfolio including the likes of The Trade Desk (IPO: 2016), Datadog and Flurry (acquired by Yahoo) just to name a few. Prior to angel investing, Jerry built the first open market for the pricing and exchange of real-time consumer data in the form of Root Markets. Jerry was also the Managing Director @ Omnicom’s Venture Capital Division where he enjoyed an incredible 5 IPOs from the portfolio.

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In Today’s Episode You Will Learn:

1.) How Jerry made his way into the world of VC in the 90s and why it was difficult to lose money in venture at that time?

2.) Why does Jerry believe that the vast portfolio construction model is “wrong” and a “dead end”? In what circumstances does Jerry believe “spray and pray” investing can work? Why does Jerry believe you can only have as many companies as you can actively help? How does this lead Jerry’s thinking on his own portfolio construction?

3.) Why does Jerry believe that startups must have a board from Day 1? What are the inherent benefits of having a board so early? In the earliest of stages, how should those board meetings be run? Who are the best board members Jerry has worked with? Why were they so exceptional? How does Jerry think about building board intimacy?

4.) Why does Jerry disagree with the conventional wisdom of Silicon Valley that price does not matter because the exit will either be huge or a zero? How has Jerry seen the best firms in their thinking on market price vs indicated discount price? How has Jerry’s thinking on price sensitivity changed over the years?

5.) Why does Jerry believe that the follow-on investment is always a much better investment? How does the risk-reward ratio change from initial to follow-on investment? How does Jerry assess and prioritize future financing risk when investing in an opportunity? How does he mitigate that as much as possible?

Items Mentioned In Today’s Show:

Jerry’s Fave Book: Console Wars by Blake Harris

Jerry’s Most Recent Investment: Edmit

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

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

We also speak about Movidiam – as brands turn to smarter ways of creating video and digital content, the Movidiam platform offers faster turnarounds whilst maintaining or improving quality. They’re already working with some of the biggest, most innovative companies to help compare teams and freelancers across the global curated network of creative talent. Producers and marketers looking for the best creatives can get a shortlist from Movidiam’s account managers in hours – tailored to their project’s needs. Submit a brief or check out the platform at Movidiam.com.

James Reinhart is the Founder & CEO @ ThredUp, the world’s largest online thrift store, and consignment store. To date, ThredUp has raised over $130m in VC funding from many friends of the show including Tim @ Redpoint, Patricia @ Trinity, Eric @ Founder Collective and Ian @ Goldman Sachs just to name a few. As for James, prior to ThredUp he was a Goldsmith Fellow in Social Enterprise at HBS and a Bill George Fellow at the Center for Public Leadership at the Kennedy School. Before that, James co-founded Beacon Education Network, a charter management organization serving low-income students on California’s Central Coast.

Chris Olsen is the Founding Partner @ Drive Capital, the venture firm that believes the Midwest is the opportunity of our lifetime with more entrepreneurs building billion-dollar companies in the Midwest than in the last 50 years combined. Since inception in 2012, Drive have built an exceptional portfolio including the likes of Duolingo, FarmLogs, LeadPages and Udacity. As for Chris, prior to founding Drive he was a Partner @ Sequoia Capital on the West Coast where he learned the craft from some of the very best in the business. Before that he spent time at both TCV and UBS.

Marco Zappacosta is the Founder & CEO @ Thumbtack, the startup that allows you to find local professionals for pretty much anything. To date, Thumbtack has raised over $270m in funding from some of the very best including Sequoia Capital, CapitalG (Google Growth), Ali and Hadi Partovi, Scott and Cyan Banister and Jason Calacanis. Due to Marco’s incredible success scaling Thumbtack to helping millions of Americans today, he has been recognized by Forbes as 30 under 30 and Thumbtack was recently acknowledged as one of GlassDoor’s best places to work.

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In Today’s Episode You Will Learn:

1.) How Marco made his way into the world of startups and came to create one of the most prominent marketplaces of the day in Thumbtack?

2.) What does Marco mean when he says “founders must treat board members as employees”? How does Marco view the optimal structure for a board meeting? What are the core elements that founders must takeaway? Where do most first time founders go wrong with board management?

3.) Thumbtack has raised over $250m in VC funding, how can one look to achieve both operational efficiency and capital efficiency with such large injections of capital? What is core to maintaining this sense of frugality despite such large investments? How does Marco think about when is the right time to raise that war chest round?

4.) How does Marco suggest that marketplace founders can entice the supply side in the early days? How has Marco seen his supply-side acquisition change and develop with time? What has worked and what has not? Does Marco agree with Leah Busque that in marketplace, the NPS for one side will always be down?

Items Mentioned In Today’s Show:

Marco’s Fave Book: The Wizard and The Prophet

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

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

Cooley is a global law firm built around supporting start-ups and the venture capital firms that fund them. Now we have spoken before about their forming the first venture fund in Silicon Valley, and forming more VC funds than any other law firm in the world but Cooley also represents more than 6,000 high-growth startups across the globe – through the full company life cycle. They are the #1 law firm for VC-backed exits (M&A and IPO) ranked by PitchBook, and since 2014 has represented more companies in their IPOs than any other law firm.  Simply head over to Cooley.com or you can check them out at Cooleygo.com.

 

Zal Bilimoria is Founding Partner @ Refactor Capital, one of Silicon Valley’s newest entrants to the early stage scene with a $50m fund looking to back founders solving fundamental human problems. Prior to co-founding Refactor, Zal was a Partner @ a16z where he co-led investments in Omada Health, Branch.co, AltSchool, Honor, and more, while helping to launch the firm’s Bio Fund. Before becoming an investor, Zal spent 10 years as a PM at Microsoft, Google, Netflix, and LinkedIn. He worked on emerging markets for Windows, became one of the first monetization team members at YouTube, and then  became the 1st Head of Mobile at Netflix and helped start the Sales Solutions business at LinkedIn.

Paul Hsiao is a Founding Partner @ Canvas Ventures, one of Silicon Valley’s leading and newer entrants to the Series A scene. At Canvas, Paul has made investments in the likes of Everwise, Fluxx Labs, Roofstock, Thrive Global, Transfix, and Zola. Before founding Canvas, Paul was a partner at NEA, where he led an early-stage investment in Houzz, as well as, had the privilege of helping eight companies go public on the NYSE or NASDAQ and seventeen companies with successful M&A exits during his 10-year tenure with the firm. Prior to VC, Paul was an entrepreneur with the founding of Mazu Networks, a pioneer in network security that was acquired by Riverbed Technologies.

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In Today’s Episode You Will Learn:

1.) How Paul made his way into the world of VC with NEA and got Scott Sandell as his first mentor in VC?

2.) Question from Oren Zeev: Having been a partner at both, how does Paul compare the culture and strategy of two such differing firms of Canvas vs NEA? How does Paul’s thinking on exit expectations and requirements change with the change of fund? How does a smaller fund fundamentally change the way you think about investing?

3.) What does Paul believe are the 5 fundamentals of building and scaling a successful marketplace? Why does Paul believe that it is the supply side that tells you if your marketplace is or is not working? Why does Paul believe stubbornness is good in marketplace founders?

4.) Why does Paul believe that raising $100m is critical for new companies if they want to go big? What does this mean for capital efficiency? What does this mean for ownership with multiple dilutive rounds impacting investor returns? How should founders then think about winning the “capital arms race”? What are the exceptions to these rules?

5.) Female founders receive 2.19% of VC funding, however, Paul has many more female founders in portfolio than the industry. Why does Paul think this is? What would Paul like to see change in the distribution of VC funds? What is the required steps to make this happen?

Items Mentioned In Today’s Show:

Paul’s Fave Book: The Innovator’s Dilemma

Paul’s Most Recent Investment: Thrive Global, Roofstock

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

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

Cooley is a global law firm built around supporting start-ups and the venture capital firms that fund them. Now we have spoken before about their forming the first venture fund in Silicon Valley, and forming more VC funds than any other law firm in the world but Cooley also represents more than 6,000 high-growth startups across the globe – through the full company life cycle. They are the #1 law firm for VC-backed exits (M&A and IPO) ranked by PitchBook, and since 2014 has represented more companies in their IPOs than any other law firm.  Simply head over to Cooley.com or you can check them out at Cooleygo.com.

Darian Shirazi is the Founder & CEO @ Radius, the startup that provides you with not just data but truth allowing you to gain clarity to reach and convert your best B2B prospects. To date, Darian has raised over $105m in VC funding with Radius from some of the very best in the business including our friends at Founders Fund, 8VC, Salesforce Ventures and rockstars like Jared Leto and Charlie Songhurst. Prior to Radius, Darian has enjoyed roles such as first external engineering hire at Facebook and working on the “Sell Your Item” team at eBay. Darian has also made several angel investments in the likes of MessageMe, Sprig and Try.com just to name a few.

Jerry Chen is a Partner @ Greylock Partners, one of the world’s most successful VC funds with prior investments in the likes of Facebook, Instagram, LinkedIn, AirBnB, Dropbox, AppDynamics, Coinbase and many more incredible companies. As for Jerry, Jerry invests in entrepreneurs building new enterprise SaaS applications and in all aspects of AI and cloud infrastructure. Jerry currently sits on the Board of Docker, Cato Networks, Gladly, Rhumbix, Spoke, and Blend. Prior to joining Greylock, Jerry was Vice President of Cloud and Application Services at VMware where he was part of the executive team that scaled the company from 250 to over 15,000 employees and $5B in revenue. Check out Jerry’s recent writing on Risk: The Game of Strategic Investment here.

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In Today’s Episode You Will Learn:

1.) How Jerry made his way into the world of VC with Greylock from being on the exec team at VMWare, responsible for their scaling from 250 to over 15,000 people?

2.) What does Jerry believe are the different frameworks for how investors should measure risk? Why does Jerry believe to be a good investor, one has to be an optimist? What does Jerry find the most challenging element of risk assessment? What types of risk can Jerry tolerate and which can he not in a potential investment?

3.) How does Jerry break the theme of risk down into 2 very different categories? How does one define “uncertainty” in an investment? How does this compare to “probability”? How does both “uncertainty and probability” alter when comparing differing sectors? Does Jerry think that current pricing takes fair account of both “uncertainty and probability”?

4.) What does Jerry mean when he says, “you have to have product go-to-market fit”? Why does Jerry believe that platforms shifts are fundamentally distribution model shifts? Where does Jerry see an inherent opportunity within these net new nodes of distribution shift?

5.) How does Jerry evaluate the SaaS world today of bottoms up or top down? Why does Jerry believe that if you are budget additive, bottoms up with small ACVs is the current strategy? What does this mean for those that are budget replacements, both in sales model and ACV?

Items Mentioned In Today’s Show:

Jerry’s Fave Book: Skin In The Game 

Jerry’s Most Recent Investment: Blend

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

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

Cooley is a global law firm built around supporting start-ups and the venture capital firms that fund them. Now we have spoken before about their forming the first venture fund in Silicon Valley, and forming more VC funds than any other law firm in the world but Cooley also represents more than 6,000 high-growth startups across the globe – through the full company life cycle. They are the #1 law firm for VC-backed exits (M&A and IPO) ranked by PitchBook, and since 2014 has represented more companies in their IPOs than any other law firm.  Simply head over to Cooley.com or you can check them out at Cooleygo.com.

Rachel Drori is the Founder & CEO @ Daily Harvest, the direct-to-consumer brand that delivers real, unprocessed, unrefined foods in the most convenient format possible: frozen. To date, they have raised over $43m in funding from the likes of former guest Alex Taussig @ Lightspeed, Collaborative Fund and future 20VC guest Beth Ferreira who sits on the board. As for Rachel, prior to starting Daily Harvest, Rachel harnessed her skills as a customer-centric marketing executive, leading teams at Gilt Groupe, American Express, and Four Seasons Hotels and Resorts.

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In Today’s Episode You Will Learn:

1.) How Rachel made her way from the corporate world of American Express and The Four Seasons to founding Daily harvest, looking to change the eating habits of millions?

2.) Why did Rachel decide to deliberately raise small Seed and Series A rounds? What does Rachel believe these capital constraints allow companies in the early days? How did Rachel prioritize where to spend and where not to? How would Rachel advise emerging startup founders when it comes to capital efficiency today?

3.) Rachel recently raised $43m Series B, how did Rachel see the rounds differ from round to round? Why does Rachel believe it is imperative to VC date before the fundraising process begins? Why was Rachel’s Series A very unconventional in the modern world of fundraising? What did Rachel look for most in the investors she chose from round to round? How is that different considering her single founder status?

4.) Question from Alex Taussig: How has Rachel seen the NYC ecosystem develop and evolve since the founding of Daily Harvest? Would Rachel agree that there remains a lack of early stage conviction investors in NYC? What are NYC’s biggest strengths and then biggest weaknesses?

5.) Rachel has said before, “fake it till you make it” when was the last time Rachel did this and what was the outcome? Rachel also said previously, “ask for forgiveness not permission”, when was the most recent occassion of this and what did it result in?

Items Mentioned In Today’s Show:

Rachel’s Fave Book: Deep Nutrition: Why Your Genes Need Traditional Food: Volume 1

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.

Leesa is the Warby Parker or TOMS shoes of the mattress industry. Leesa have done away with the terrible mattress showroom buying experience by creating a luxury premium foam mattress that is ordered completely online and ships for free to your doorstep. The 10-inch mattress comes in all sizes and is engineered with 3 unique foam layers for a universal, adaptive feel, including 2 inches of memory foam and 2 inches of a really cool latex foam called Avena, design to keep you cool. All Leesa mattresses are 100% US or UK made and for every 10 mattresses they sell, they donate one to a shelter. Go to Leesa.com to start the New Year with better nights sleep!

Zoom, fastest growing video and web conferencing service, providing one consistent enterprise experience that allows you to engage in an array of activities including video meetings and webinars, collaboration-enabled conference rooms, and persistent chat all in one easy platform. Plus, it is the easiest solution to manage, scale, and use, and has the most straightforward, affordable pricing. Don’t take our word for it. Zoom is the top rated conferencing app across various user review sites including G2Crowd and Trust Radius. And you can sign up for a free account (not a trial!). Just visit Zoom.us.

Dan Lewis is the Founder & CEO @ Convoy, the startup that really is the future of freight with trucking services powered by technology to drive reliability, efficiency and insights. To date they have raised over $80m in funding from some of the world’s best-known investors and individuals including Y Combinator Continuity Fund, Greylock, Jeff Bezos, Marc Benioff, Drew Houston, Kevin Systrom and leading angels, Ali and Hadi Partovi. Before Convoy, Dan served as general manager of new shopping experiences at Amazon and spent time at Google and Microsoft in a number of logistics-related roles.

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In Today’s Episode You Will Learn:

1.) How Daniel first fell in love with the logistics space as a little boy, made his move into the world of tech with Google and Microsoft and came to found Convoy?

2.) How does Dan truly define the differences between linear and non-linear businesses? Why does Dan believe that startup timing is like surfing? How must founders think about this through the different stages of the business?

3.) What was Dan’s strategy for choosing the right investors and how did he think about board composition? How can investors be used to build customer trust? How does Dan analyze and look to enhance board chemistry? What was a time for Dan when he actively went against the advice of the board? How did that play out?

4.) Why did Dan accept so many investors at the seed round? What changed between rounds that made Dan want to go big with the $62m Series B? Does Dan agree with Reid Hoffman, “if you can raise the money, do”? Why did Dan choose YC Continuity Fund as the lead growth investor of choice? What were the benefits?

5.) Why does Dan believe that scaling the first initial customers is the hardest of all? Why does Dan believe that a culture of experimentation is key across functions? How does Dan think about his own scaling as CEO? How has he seen his role change with the growth of the firm? What have been the biggest challenges of this personal learning?

Items Mentioned In Today’s Show:

Dan’s Fave Book: The Stranger by Albert Camus

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

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

Leesa is the Warby Parker or TOMS shoes of the mattress industry. Leesa have done away with the terrible mattress showroom buying experience by creating a luxury premium foam mattress that is ordered completely online and ships for free to your doorstep. The 10-inch mattress comes in all sizes and is engineered with 3 unique foam layers for a universal, adaptive feel, including 2 inches of memory foam and 2 inches of a really cool latex foam called Avena, design to keep you cool. All Leesa mattresses are 100% US or UK made and for every 10 mattresses they sell, they donate one to a shelter. Go to Leesa.com to start the New Year with better nights sleep!

Zoom, fastest growing video and web conferencing service, providing one consistent enterprise experience that allows you to engage in an array of activities including video meetings and webinars, collaboration-enabled conference rooms, and persistent chat all in one easy platform. Plus, it is the easiest solution to manage, scale, and use, and has the most straightforward, affordable pricing. Don’t take our word for it. Zoom is the top rated conferencing app across various user review sites including G2Crowd and Trust Radius. And you can sign up for a free account (not a trial!). Just visit Zoom.us.

Leah Busque is a General Partner @ Fuel Capital, one of Silicon Valley’s leading seed funds with the most incredible portfolio including many previous 20VC guests Ryan @ Flexport, Florian @ Mesosphere, Alex @ Clearbit and Dan @ Convoy (episode Friday). As for Leah, prior to VC, she was a pioneer of the sharing economy with her founding of TaskRabbit, one of the leading online labor marketplaces in the US, raising over $37m in the process before their sale to IKEA last year. Due to this incredible success, Leah has been named to Fast Company’s “100 Most Creative People in Business”.

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In Today’s Episode You Will Learn:

1.) How Leah made her way from sitting on the couch discussing dog food with her husband to founding TaskRabbit and how that translated into the world of VC today?

2.) How did Leah’s time in operations affect:

• Question from Sean @ Shasta: the founders Leah backs and why she chooses them?
• Question from Craig @ Collaborative: the business models and unit economics Leah backs and why she backs them?

3.) Leah has said before that “authenticity and transparency between VC and founder are now table stakes”, what more can be done to improve the VC product? How did Leah select the investors she worked with on TaskRabbit? How can founders truly determine “founder friendly” VCs?

4.) What have been Leah’s biggest surprises on her move into the world of VC? What elements has Leah found most challenging? How has Leah looked to scale that learning curve?

5.) What does a successful marketplace look like? How does one know when is the right time to really scale a marketplace? What is the inflection point? How can marketplaces be efficient with their unit economics from day 1? How does one balance the NPS of the supply side with the NPS of the demand side?

Items Mentioned In Today’s Show:

Leah’s Fave Book: Founders at Work 

Leah’s Most Recent Investment: Bark: Parental Control Phone Tracker App

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

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

Leesa is the Warby Parker or TOMS shoes of the mattress industry. Leesa have done away with the terrible mattress showroom buying experience by creating a luxury premium foam mattress that is ordered completely online and ships for free to your doorstep. The 10-inch mattress comes in all sizes and is engineered with 3 unique foam layers for a universal, adaptive feel, including 2 inches of memory foam and 2 inches of a really cool latex foam called Avena, design to keep you cool. All Leesa mattresses are 100% US or UK made and for every 10 mattresses they sell, they donate one to a shelter. Go to Leesa.com to start the New Year with better nights sleep!

Zoom, fastest growing video and web conferencing service, providing one consistent enterprise experience that allows you to engage in an array of activities including video meetings and webinars, collaboration-enabled conference rooms, and persistent chat all in one easy platform. Plus, it is the easiest solution to manage, scale, and use, and has the most straightforward, affordable pricing. Don’t take our word for it. Zoom is the top rated conferencing app across various user review sites including G2Crowd and Trust Radius. And you can sign up for a free account (not a trial!). Just visit Zoom.us.

Mike Silagadze is the Founder & CEO @ Top Hat, the market leader in student engagement software, and is used by millions of students at three-quarters of the top 1,000 colleges and universities in North America. To date, they have raised over $47m in VC funding from many friends and former guests on the show including Albert Wenger @ USV, Boris Wertz @ Version One, Uncork Capital, Felicis and Emergence just to name a few. As for Mike, prior to TopHat, he was a developer at MioVision Technologies.

Alex Taussig 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, The Honest Company and many more incredible companies. As for Alex, at Lightspeed, he has made investments in Zola, Daily Harvest, Vector & Poncho. Before moving to the West Coast, Alex spent 7 years at Highland Capital Partners, where, as a Partner, he made investments in thredUp, JauntVR and RentJuice (acq by Zillow) and was involved in several IPOs. Alex is also the writer of a fantastic newsletter: Drinking From The Firehose.

Leore Avidar is the Founder & CEO @ Lob, the startup that provides a powerful suite of API’s to deliver robust automation and scale for anything with a stamp. To date, Lob has raised close to $30m in funding from some of the greats of the investing world including Floodgate, Initialized, First Round and most recently YC’s Continuity Fund. As for Leore, prior to Lob he spent time in the technical business development team at Amazon Web Services and before that was a derivatives trader on Wall St with Citigroup.

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In Today’s Episode You Will Learn:

1.) How Leore made the move from the world of trading on Wall St to founding one the game-changing companies in the world of API’s, Lob?

2.) What does Leore believe are the 2 levers that founders must use when fundraising? How can founders create a sense of VC FOMO when raising their round? How can founders enter a round with leverage? What does always having the upper hand in fundraising look like?

3.) How does Leore define “sustainable growth”? Why does Leore believe that most fast-growing companies do go bankrupt? What is Leore’s biggest fear with regards to “sustainable growth”? How does Leore advise founders to think about macro funding conditions when operating their company and thinking about expenditure?

4.) How has Leore seen his role as CEO change with the scaling of the company? Why does Leore believe the main job of the CEO is to hire and replace yourself? What have been the biggest challenges for Leore in the scaling of himself?

5.) Leore wants to create a company where people stay for 30+ years, what are the foundations to a workplace culture with such deep routes? What must be done from management to ensure this? How does Leore approach accountability and responsibility amongst the team?

Items Mentioned In Today’s Show:

Leore’s Fave Book: Multipliers: How the Best Leaders Make Everyone Smarter

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

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

Leesa is the Warby Parker or TOMS shoes of the mattress industry. Leesa have done away with the terrible mattress showroom buying experience by creating a luxury premium foam mattress that is ordered completely online and ships for free to your doorstep. The 10-inch mattress comes in all sizes and is engineered with 3 unique foam layers for a universal, adaptive feel, including 2 inches of memory foam and 2 inches of a really cool latex foam called Avena, design to keep you cool. All Leesa mattresses are 100% US or UK made and for every 10 mattresses they sell, they donate one to a shelter. Go to Leesa.com to start the New Year with better nights sleep!

Zoom, fastest growing video and web conferencing service, providing one consistent enterprise experience that allows you to engage in an array of activities including video meetings and webinars, collaboration-enabled conference rooms, and persistent chat all in one easy platform. Plus, it is the easiest solution to manage, scale, and use, and has the most straightforward, affordable pricing. Don’t take our word for it. Zoom is the top rated conferencing app across various user review sites including G2Crowd and Trust Radius. And you can sign up for a free account (not a trial!). Just visit Zoom.us.

Anu Hariharan is a Partner @ Y Combinator’s Continuity Fund, the growth stage investing arm of Y Combinator that has made investments in the likes of Segment, Lob (coming on Friday), Convoy, where Anu is a board member and RazorPay. Prior to YC, Anu was an investment partner at Andreessen Horowitz, where she worked actively with the management teams of portfolio companies including Airbnb, Instacart, Medium, OfferUp and Udacity. Before that Anu was a Principal at The Boston Consulting Group’s Private Equity practice where she led multiple growth equity due diligences in the consumer and fintech sector.

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In Today’s Episode You Will Learn:

1.) How Anu made her way from engineer to consultant to Andreesen investment partner to now, one of the leading members of YC’s growth stage investing vehicle?

2.) How does Anu truly define “network effect”? Where does Anu think startups most commonly misunderstand network effects? Which form of network effect does Anu find most exciting? Why? How has this evolved over the years?

3.) What are the 2 core indicators that show the sustainability of network effect? Looking at past examples of products and founders, who has best executed on this? What are the signs that founding teams fundamentally analyze and optimize network effect virality?

4.) Why does Anu believe that growth teams will be a fundamental requirement for companies in the future? What are the 2 mistakes startups make when establishing their growth team? How does one know when is the right time to build their growth team? What are the core challenges in scaling growth teams? How does this drive decision-making?

5.) How does Anu describe “Phase 1” and “Phase 2” of company scaling? What transition must the CEo adopt when making this scaling transition? Comparing founders, what are the commonalities in those that succeed with the transition and those that do not?

Items Mentioned In Today’s Show:

Anu’s Fave Book: Grit by Angela Duckworth

Anu’s Most Recent Investment: Convoy

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

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

Leesa is the Warby Parker or TOMS shoes of the mattress industry. Leesa have done away with the terrible mattress showroom buying experience by creating a luxury premium foam mattress that is ordered completely online and ships for free to your doorstep. The 10-inch mattress comes in all sizes and is engineered with 3 unique foam layers for a universal, adaptive feel, including 2 inches of memory foam and 2 inches of a really cool latex foam called Avena, design to keep you cool. All Leesa mattresses are 100% US or UK made and for every 10 mattresses they sell, they donate one to a shelter. Go to Leesa.com to start the New Year with better nights sleep!

Zoom, fastest growing video and web conferencing service, providing one consistent enterprise experience that allows you to engage in an array of activities including video meetings and webinars, collaboration-enabled conference rooms, and persistent chat all in one easy platform. Plus, it is the easiest solution to manage, scale, and use, and has the most straightforward, affordable pricing. Don’t take our word for it. Zoom is the top rated conferencing app across various user review sites including G2Crowd and Trust Radius. And you can sign up for a free account (not a trial!). Just visit Zoom.us.

Mariam Naficy has pioneered consumer Internet models since 1998, when she co-founded the first online cosmetics retailer, Eve.com, which was sold for over $100 million. Today, Mariam is the Founder & CEO @ Minted, the startup that uses crowdsourcing and analytics to bring the best designs to market faster than anyone. To date, Mariam has raised &89m in VC funding with Minted from some of the best in the business including our favourites Floodgate, Benchmark, Menlo, Slow, Ridge Ventures and then prominent individuals such as Marissa Meyer and Jeremy Stoppelman. In addition, Mariam sits on the Board of Yelp and Every Mother Counts.

Steve Vassallo is a General Partner @ Foundation Capital where he sits or has sat on the boards of Pocket (acquired by Mozilla), PrivateCore (acquired by Facebook), Sunrun [RUN], Sentient Energy and many more. Prior to Foundation, Steve was Senior Vice President of Product and Engineering @ Ning, the social platform he helped launch in 2004. Before that, Steve was a project leader at IDEO, where he developed more than a dozen successful products for companies including Cisco, Nike, BMW and McDonalds. In addition, this year, Steve published The Way to Design, a guidebook for becoming a designer founder and building a design-centric company.

Chris Hutchins is the Founder & CEO @ Grove, the startup reinventing financial planning allowing you to reach your goals with personalized financial advice. Just last week they announced their seed round from some of the best in the business including First Round Capital, Lowercase Capital, Box Group and SV Angel. Prior to Grove, Chris was an Partner & EiR with Google Ventures and before that co-founded Milk (acq by Google) alongside Kevin Rose.

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In Today’s Episode You Will Learn:

1.) How Chris made the move from Google acquired Founder to Partner @ Google Ventures to now, founding First Round backed, Grove?

2.) What does Chris believe are the foundational elements founders must consider pre-fundraise? How does Chris suggest founders structure the process? How important is a fundraise deadline? How does Chris advise founders on getting warm intros, what is best?

3.) How can founders really optimise VC interactions? What is the biggest mistake founders make when meeting VCs? What should founders be looking to take from these meetings? How transparent should founders be about their meetings with other investors?

4.) What are Chris’ view on the rise of SAFE’s vs priced equity rounds? In what situations do SAFE’s make sense? How did Chris think about this with his own fundraise recently? Does Chris believe there is too much money in the ecosystem? Where are there gaps and where is there overfunding?

5.) Why does Chris think hiring is a “big data problem”? Where do many founders make mistakes in recruiting in the early days? What hacks can be done to ensure a quality stream of candidates continuously?

Items Mentioned In Today’s Show:

Chris’ Fave Book: Happy Money

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

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

Cooley are the global law firm built around startups and venture capital.  Since forming the first venture fund in Silicon Valley, Cooley has formed more venture capital funds than any other law firm in the world, with 50+ years working with VCs. They help VCs form and manage funds, make investments and handle the myriad issues that arise through a fund’s lifetime. So to learn more about the #1 most active law firm representing VC-backed companies going public. Head over to cooley.com and also at cooleygo.com.

Zoom, fastest growing video and web conferencing service, providing one consistent enterprise experience that allows you to engage in an array of activities including video meetings and webinars, collaboration-enabled conference rooms, and persistent chat all in one easy platform. Plus, it is the easiest solution to manage, scale, and use, and has the most straightforward, affordable pricing. Don’t take our word for it. Zoom is the top rated conferencing app across various user review sites including G2Crowd and Trust Radius. And you can sign up for a free account (not a trial!). Just visit Zoom.us.

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, The Honest Company 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.

Nadia Boujarwah is the Founder & CEO @ Dia & Co, the startup that provides premier plus size clothing and styling for women. To date they have raised over $20m in funding from some of the best in the business including the likes of Alfred Lin @ Sequoia and the team @ NextView Ventures. Prior to Dia&Co Nadia was the CFO and COO @ Frieda and Nellie and also enjoyed time in the marketing and strategy team @ Diane von Furstenberg.

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In Today’s Episode You Will Learn:

1.) How Nadia made her way from HBS grad to founding one of the hottest e-commerce companies of the day backed by Sequoia, Dia&Co?

2.) Why does Nadia believe that the biggest opportunity for value creation is through category creation? What does Nadia mean when she discusses category re-architecture? How does she think of the inherent cons (CAC, consumer education, distribution etc.)

3.) Despite the likes of Sequoia being invested now, the first year of Dia gained no institutional money. Why does Nadia think this is? What was the inflection point for VC interest? Is there anything that Nadia would change about how she has run the fundraising process?

4.) What does Nadia suggest as some core solutions to ensuring that more females become VCs? How does Nadia believe this will impact the types of companies that are being funded and built? What remain the core issues today?

5.) How does Nadia differentiate between customer centricity and customer devotion? Why is this so crucial in today’s proliferated world of e-commerce? How does Nadi and Dia determine with data, the extent to which they achieve their customer devotion targets?

Items Mentioned In Today’s Show:

Nadia’s Fave Book: Competing Against Luck

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

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

Cooley are the global law firm built around startups and venture capital.  Since forming the first venture fund in Silicon Valley, Cooley has formed more venture capital funds than any other law firm in the world, with 50+ years working with VCs. They help VCs form and manage funds, make investments and handle the myriad issues that arise through a fund’s lifetime. So to learn more about the #1 most active law firm representing VC-backed companies going public. Head over to cooley.com and also at cooleygo.com.

Zoom, fastest growing video and web conferencing service, providing one consistent enterprise experience that allows you to engage in an array of activities including video meetings and webinars, collaboration-enabled conference rooms, and persistent chat all in one easy platform. Plus, it is the easiest solution to manage, scale, and use, and has the most straightforward, affordable pricing. Don’t take our word for it. Zoom is the top rated conferencing app across various user review sites including G2Crowd and Trust Radius. And you can sign up for a free account (not a trial!). Just visit Zoom.us.

Dick Costolo is the Chief Executive and co-founder of Chorus, a startup that is reimagining the path to personal fitness. Dick is also a Mentor @ Index Ventures, one of the world’s leading venture funds, which he joined in 2016. Costolo was most recently Chief Executive of Twitter from 2010 to 2015, where was at the forefront for their hypergrowth onto the main stage of tech. Prior to joining Twitter, Dick co-founded and ran three startups, including FeedBurner, which sold to Google in 2007. The former improv comedian has been a consultant on HBO’s “Silicon Valley” and currently sits on the boards of Patreon and IfOnly.

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In Today’s Episode You Will Learn:

1.) How Dick made his way from Improv Comedian to founding a startup acquired by Google and then becoming CEO of Twitter?

2.) Why does Dick believe that starting a company is like an improv stage? What were Dick’s biggest personal learnings from his drama career that he has applied to being a better leader today?

3.) Having given up the comedy dream for tech, how does Dick balance the entrepreneurial unwavering vision with a realism of when things are not working? What is the inflection point?

4.) What was the biggest challenge over the 5 years in scaling Twitter? What strategies did Dick utilise to combat this? How does Dick think about creating a culture of accountability without fear? How does this change the ownership of decisions?

5.) What is Dick’s biggest superpower and super weakness? Why must all entrepreneurs have to have a fundamental ability to compartmentalize? In terms of temperament, what were Dick’s biggest lessons from watching Youtube CEO, Susan Wojcicki, operate?

Items Mentioned In Today’s Show:

Dick’s Fave Book: Creativity Inc.

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

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

Cooley are the global law firm built around startups and venture capital.  Since forming the first venture fund in Silicon Valley, Cooley has formed more venture capital funds than any other law firm in the world, with 50+ years working with VCs. They help VCs form and manage funds, make investments and handle the myriad issues that arise through a fund’s lifetime. So to learn more about the #1 most active law firm representing VC-backed companies going public. Head over to cooley.com and also at cooleygo.com.

Zoom, fastest growing video and web conferencing service, providing one consistent enterprise experience that allows you to engage in an array of activities including video meetings and webinars, collaboration-enabled conference rooms, and persistent chat all in one easy platform. Plus, it is the easiest solution to manage, scale, and use, and has the most straightforward, affordable pricing. Don’t take our word for it. Zoom is the top rated conferencing app across various user review sites including G2Crowd and Trust Radius. And you can sign up for a free account (not a trial!). Just visit Zoom.us.

Brian Garrett is the Founding Partner @ Crosscut Ventures, one of LA’s leading venture funds today with a portfolio including Super Evil Mega Corp, The Black Tux and Mobcrush just to name a few. Incredibly during the early days of Crosscut, Brian went back into a full-time operating role with a Public-company turnaround at Quepasa.com before co-founding vertical eCommerce brand StyleSaint.com. After surviving with the equivalent of two full-time jobs for roughly 6 years, Brian the attention of institutional capital, which enabled CrossCut to scale into a fund with $75M raised for CrossCut 3 in 2015. This has snowballed to their latest fund raised in December being $125m.

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In Today’s Episode You Will Learn:

1.) How Brian made his way into the world of VC and came to found one of LA’s leading funds in the form of Crosscut?

2.) What does Brian believe are the 3 core components that make for a successful VC? How important is the presence of humility for VCs today? How does Brian look to balance between arrogance and confidence? How is this shown in the entrepreneurial class?

3.) Why does Brian believe that vulnerability is actually a strength today? How can entrepreneurs be honest and vulnerable without ruining market perceptions and future fundraising aspirations?

4.) How does Brian look to place his relationship with the entrepreneur at the very core of every investment he makes? What does this relationship onboarding process look like? Is this possible in the fast-moving world of US deals today?

5.) What was the most challenging fundraise for Brian? Why was this case? How has he seen the evolution of Californian tech over the last few years since Fund III? What was the most memorable LP meeting for Brian?

Items Mentioned In Today’s Show:

Brian’s Fave Book: The Alchemist

Brian’s Most Recent Investment: Fuzzy Pet Health

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

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

Cooley are the global law firm built around startups and venture capital.  Since forming the first venture fund in Silicon Valley, Cooley has formed more venture capital funds than any other law firm in the world, with 50+ years working with VCs. They help VCs form and manage funds, make investments and handle the myriad issues that arise through a fund’s lifetime. So to learn more about the #1 most active law firm representing VC-backed companies going public. Head over to cooley.com and also at cooleygo.com.

Zoom, fastest growing video and web conferencing service, providing one consistent enterprise experience that allows you to engage in an array of activities including video meetings and webinars, collaboration-enabled conference rooms, and persistent chat all in one easy platform. Plus, it is the easiest solution to manage, scale, and use, and has the most straightforward, affordable pricing. Don’t take our word for it. Zoom is the top rated conferencing app across various user review sites including G2Crowd and Trust Radius. And you can sign up for a free account (not a trial!). Just visit Zoom.us.

Andy Pflaum is the Founder & CEO @ Astro, the startup that brings email, calendar, and an AI-powered assistant together to help you focus on what’s most important. They have raised over $10m from leading West Coast investors such as Satish @ Redpoint, former guests Kent Goldman @ Upside and Michael Dearing @ Harrison Metal. As for Andy, prior to founding Astro, he spent 15 years in the valley, serving as the CMO @ Zimbra where he saw their immense scaling to their $350m acquisition by VMware where he then spent time on the other side of the table before moving to Chile to manage a family winery for 1.5 years.

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In Today’s Episode You Will Learn:

1.) How Andy made his way into the world of startups, made the transition to large corporates with VMware and Yahoo, came to run a Winery in Chile before founding Astro?

2.) Found a startup, work in early-stage startup or work at large incumbent; where does Andy believe young people today have the biggest growth opportunities? How does this mean emerging startups have to react to attain that talent?

3.) Why does Andy disagree with the notion that more and more incumbents are falling? Why is it harder than ever to compete against such a strong set of incumbents? What are the dangers of dependency on paid growth?

4.) How does Andy feel about distributed workforces? What is core to attaining the individuals and then scaling them successfully as a team, in a distributed fashion? How does Andy feel about hiring technical talent in the bay today?

5.) Why does Andy also argue, despite the incumbents, that it is also easier than ever to operate a business today What are the core changes that have allowed for this to happen? How does Andy break down the tech stack they use for Astro?

Items Mentioned In Today’s Show:

Andy’s Fave Book: The Wright Brothers

Andy’s Fave Blog: Tom Tunguz, Michael Dearing: Harrison Metal

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

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

NatureBox Unlimited snack plans offer all you can eat snacks for one fixed price per employee. Naturebox use simple ingredients you can trust to create bold flavors you can’t find anywhere else. All NatureBox snacks are free from artificial junk and variety is endless with options from sweet or savory to vegan or gluten-free. Simply choose the plan that fits your team’s unique snacking habits and select any of NatureBox’s time-saving add-on’s. And beyond Unlimited snacks, you’ll receive perks such as free kitchen setup, no contracts, a dedicated account manager and more. Simply click here to and use the offer code VC20 to get 20% of your first Naturebox month.

Leesa is the Warby Parker or TOMS shoes of the mattress industry. Leesa have done away with the terrible mattress showroom buying experience by creating a luxury premium foam mattress that is ordered completely online and ships for free to your doorstep. The 10-inch mattress comes in all sizes and is engineered with 3 unique foam layers for a universal, adaptive feel, including 2 inches of memory foam and 2 inches of a really cool latex foam called Avena, design to keep you cool. All Leesa mattresses are 100% US or UK made and for every 10 mattresses they sell, they donate one to a shelter. Go to Leesa.com to start the New Year with better nights sleep!

Andrew Parker is a General Partner @ Spark Capital, one of the best performing funds of the last decade with a portfolio including the likes of Twitter, Slack, Oculus, Medium, PostMates, Cruise (acq $1Bn) the list goes on. As for Andrew, he has led Spark’s investments in Carta, Kik, Panorama Education, Socratic, Splash, Particle and Quantopian. Prior to joining Spark in 2010, Andrew was a member of the investment team at Union Square Ventures. Before becoming an investor, Andrew did UI design and user-experience testing at Homestead Technologies and was a web developer at Groupspace.org.

Neil Young is the Founder & CEO @ N3twork, the next generation mobile games maker and publisher with their services already touching millions of customers. They have raised over $17m in VC funding from some of the very best in the business including Mike Maples @ Floodgate, Bing Gordon @ KPCB and the team at Google Ventures. Prior to N3TWORK, Neil founded ngmoco, a leading social mobile games company, acquired by DeNA for a reported up to $400m. Before ngmoco, Neil spent many years at Electronic Arts where he was responsible for producing some of EA’s most successful game franchises including: The Lord of the Rings, The Sims, Medal of Honor and Command and Conquer, among others.

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In Today’s Episode You Will Learn:

1.) How Neil made his way from telling his mother in the UK he was not going to university to producing world-leading games, to selling a company for a reported $400m?

2.) What are the 2 questions Neil believes everyone should ask when evaluating the potential of a new platform? How does Neil think about the platform shifts at present given his publishing to mobile? Where do most people make mistakes when assessing platform shifts?

3.) Peter Fenton stated on the show: “startups are starved of free and open distribution”. How does Neil think about incumbency advantages with regards to distribution? Would an open platform yield greater potential distribution? How does Neil view the world of paid and performance marketing today? How has his views changed on the space?

4.) What are the 3 things that Neil believes all founders must do in order to assemble and manage a board successfully? Why is it important to listen to board members on their own and as a group and compare? Where do most founders go wrong in board management?

5.) Neil sold ngmoco for a reported $400m, what does Neil believe are the 2 big questions that all founders must ask themselves when contemplating a potential sale? What are the 2 different types of acquisitions that exist today?

Items Mentioned In Today’s Show:

Neil’s Fave Book: The Second World War

Neil’s Fave Blog: Gaming Insiders

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

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

NatureBox Unlimited snack plans offer all you can eat snacks for one fixed price per employee. Naturebox use simple ingredients you can trust to create bold flavors you can’t find anywhere else. All NatureBox snacks are free from artificial junk and variety is endless with options from sweet or savory to vegan or gluten-free. Simply choose the plan that fits your team’s unique snacking habits and select any of NatureBox’s time-saving add-on’s. And beyond Unlimited snacks, you’ll receive perks such as free kitchen setup, no contracts, a dedicated account manager and more. Simply click here to and use the offer code VC20 to get 20% of your first Naturebox month.

Leesa is the Warby Parker or TOMS shoes of the mattress industry. Leesa have done away with the terrible mattress showroom buying experience by creating a luxury premium foam mattress that is ordered completely online and ships for free to your doorstep. The 10-inch mattress comes in all sizes and is engineered with 3 unique foam layers for a universal, adaptive feel, including 2 inches of memory foam and 2 inches of a really cool latex foam called Avena, design to keep you cool. All Leesa mattresses are 100% US or UK made and for every 10 mattresses they sell, they donate one to a shelter. Go to Leesa.com to start the New Year with better nights sleep!

Eurie Kim is a General Partner @ Forerunner Ventures, the early stage firm dedicated to investing in entrepreneurs defining the next generation of commerce. Fun fact, they are the only firm to have investments in both Jet.com and Dollar Shave Club, two of the biggest and highest-profile e-commerce exits in recent years. Forerunner also counts Birchbox, Bonobos, Glossier, Hotel Tonight, Warby Parker and Zola among its portfolio companies. Prior to Forerunner, Eurie was a consultant at Bain and before that an investor at Castanea Partners. Eurie currently sits on the boards of companies such as Away, MoveWith and The Farmers Dog, just to name a few.

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In Today’s Episode You Will Learn:

1.) How Eurie made her into the world of VC and investing in the next generation of commerce with Forerunner?

2.) How does Eurie look to argue that commerce deals do attain the same revenue multiple on exit as enterprise deals? Do Forerunner think about exit potential when investing in companies? How does this Eurie’s thesis on both ownership and price sensitivity? What are the required fund-returning ownership levels today?

3.) With the time it takes for brands to flourish, how does Forerunner think about reserve allocation? How does Forerunner determine which companies to double down on and which to constrain capital? Why does Eurie believe that it takes less time than ever for brands to flourish today? What is a good example of this?

4.) How does Eurie define the term “digitally native vertically integrated brand”? What are the core components that make those all star brands of today shine in the early days? What are the commonalities in those successful founders that build these mega brands?

5.) Given the rise of some prominent new brands eating incumbent market share, does Eurie believe this is a market of consolidation or new incumbents will be made? How does Eurie view the role of Amazon? To what extent does Eurie observe and analyse Amazon’s activity?

Items Mentioned In Today’s Show:

Eurie’s Fave Book: Blue Ocean Strategy 

Eurie’s Fave Blog: Business of Fashion

Eurie’s Most Recent Investment: Shop Shops

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

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

NatureBox Unlimited snack plans offer all you can eat snacks for one fixed price per employee. Naturebox use simple ingredients you can trust to create bold flavors you can’t find anywhere else. All NatureBox snacks are free from artificial junk and variety is endless with options from sweet or savory to vegan or gluten-free. Simply choose the plan that fits your team’s unique snacking habits and select any of NatureBox’s time-saving add-on’s. And beyond Unlimited snacks, you’ll receive perks such as free kitchen setup, no contracts, a dedicated account manager and more. Simply click here to and use the offer code VC20 to get 20% of your first Naturebox month.

Leesa is the Warby Parker or TOMS shoes of the mattress industry. Leesa have done away with the terrible mattress showroom buying experience by creating a luxury premium foam mattress that is ordered completely online and ships for free to your doorstep. The 10-inch mattress comes in all sizes and is engineered with 3 unique foam layers for a universal, adaptive feel, including 2 inches of memory foam and 2 inches of a really cool latex foam called Avena, design to keep you cool. All Leesa mattresses are 100% US or UK made and for every 10 mattresses they sell, they donate one to a shelter. Go to Leesa.com to start the New Year with better nights sleep!

Florian Leibert is the Founder & CEO @ Mesosphere, the most flexible platform for containerized, data-intensive applications. They are trusted by some of the world’s leading companies from Yelp to Yammer to Verizon and have raised over $120m in VC funding from the likes of a16z, Kleiner Perkins, Khosla, Data Collective and then incumbents such as Microsoft and Hewlett Packard. Prior to founding Mesosphere, Florian spent time with Twitter and Airbnb, both as a tech lead and if that was not enough, Florian also has a stellar angel portfolio including the likes of Away, Cockroach Labs, Drift and Buoyant.

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In Today’s Episode You Will Learn:

1.) How Florian came to found Mesosphere? What were the big takeaways for him from his more formative years at Twitter and Airbnb?

2.) Why does Florian believe that sometimes “you should not listen to your investors”? What is the right way to communicate this disagreement to them? What supporting evidence is required to substantiate your thoughts? What method would Florian prefer to receive such feedback?

3.) What are the biggest benefits of having strategics such as Microsoft and Hewlett Packard on the cap table? What are some potential drawbacks? What advice would Florian give to founders contemplating taking strategic investment? When is the right time for these staretgics to insert themselves?

4.) With the scaling of Mesosphere, how have Florian’s thoughts and approach to sales execution changed? What have been the core struggles? Why does Florian think it is imperative to build the sales team slowly?

5.) At what point does Florian think that operational efficiency must be front and centre for founders scaling their companies? What has Florian found to be the most challenging personally in achieving such operational efficiency?

Items Mentioned In Today’s Show:

Florian’s Fave Book: Alchemist: A Fable about Following Your Dream

Florian’s Fave Blog: Seeking Alpha

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

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

NatureBox Unlimited snack plans offer all you can eat snacks for one fixed price per employee. Naturebox use simple ingredients you can trust to create bold flavors you can’t find anywhere else. All NatureBox snacks are free from artificial junk and variety is endless with options from sweet or savory to vegan or gluten-free. Simply choose the plan that fits your team’s unique snacking habits and select any of NatureBox’s time-saving add-on’s. And beyond Unlimited snacks, you’ll receive perks such as free kitchen setup, no contracts, a dedicated account manager and more. Simply click here to and use the offer code VC20 to get 20% of your first Naturebox month.

Leesa is the Warby Parker or TOMS shoes of the mattress industry. Leesa have done away with the terrible mattress showroom buying experience by creating a luxury premium foam mattress that is ordered completely online and ships for free to your doorstep. The 10-inch mattress comes in all sizes and is engineered with 3 unique foam layers for a universal, adaptive feel, including 2 inches of memory foam and 2 inches of a really cool latex foam called Avena, design to keep you cool. All Leesa mattresses are 100% US or UK made and for every 10 mattresses they sell, they donate one to a shelter. Go to Leesa.com to start the New Year with better nights sleep!

Sam Altman is the president of Y Combinator, the world’s most successful accelerator with alumni that includes the likes of Airbnb, Dropbox, Reddit, Flexport and many more incredible companies. Sam is also the co-chair of OpenAI, thenon-profit AI research company, discovering and enacting the path to safe artificial general intelligence. Prior to YC, Sam was co-founder and CEO of Loopt, which was funded by Y Combinator in 2005 and acquired by Green Dot in 2012. Sam also founded Hydrazine Capital, whose stellar portfolio included the likes of Zenefits, Flexport and Soylent.

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In Today’s Episode You Will Learn:

1.) How Sam made his way into the world of startups with Loopt and YC? How he came to invest with Hydrazine Capital and then rejoin YC as Partner and now President?

2.) Having watched and seen Paul Graham since Batch 1, what does Sam believe makes Paul Graham the special leader he is? What makes Sam and Paul such great Partners? How did they enact the transition of Sam to President? How did it change the relationship?

3.) What is Sam’s tactic that he uses to fully evaluate the skills and execution of a founder? When investing where did Sam make his most frequent mistakes? Why does Sam expect seed stage investing as a whole, will compress? Is Sam concerned of too much capital in the market at present?

4.) Question from Jack Altman: what is the main difference between a great seed investor and a great Series A investor? Sam has said before he likes to invest in messy, somewhat broken companies”. How does Sam determine between the fixable and the unfixable? How much of a role does price play in his evaluation of an opportunity?

5.) One of Sam’s recent goals was “figure out how to scale YC 2x”. How does Sam think about this in terms of stage? Will YC replace VC with lifecycle funding? How does Sam think about YC’s expansion geographically into China? How does Sam assess the vertical expansion of deep tech and bio tech that YC is going after?

Items Mentioned In Today’s Show:

Sam’s Fave Book: The Making of The Atomic Bomb

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

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

NatureBox Unlimited snack plans offer all you can eat snacks for one fixed price per employee. Naturebox use simple ingredients you can trust to create bold flavors you can’t find anywhere else. All NatureBox snacks are free from artificial junk and variety is endless with options from sweet or savory to vegan or gluten-free. Simply choose the plan that fits your team’s unique snacking habits and select any of NatureBox’s time-saving add-on’s. And beyond Unlimited snacks, you’ll receive perks such as free kitchen setup, no contracts, a dedicated account manager and more. Simply click here to and use the offer code VC20 to get 20% of your first Naturebox month.

Leesa is the Warby Parker or TOMS shoes of the mattress industry. Leesa have done away with the terrible mattress showroom buying experience by creating a luxury premium foam mattress that is ordered completely online and ships for free to your doorstep. The 10-inch mattress comes in all sizes and is engineered with 3 unique foam layers for a universal, adaptive feel, including 2 inches of memory foam and 2 inches of a really cool latex foam called Avena, design to keep you cool. All Leesa mattresses are 100% US or UK made and for every 10 mattresses they sell, they donate one to a shelter. Go to Leesa.com to start the New Year with better nights sleep!

Emilie Choi is Head of Corporate Development @ Linkedin where she has led 40+ acquisitions, acquihires or investments. In terms of acquisitions, Emilie led the acquisitions of Lynda, Bizo, Newsle, Bright, Pulse, SlideShare, and Rapportive just to name a few. On the strategic investment side, she led Linkedin’s investment in Cornerstone On Demand and G2 Crowd. Before Linkedin, Emilie enjoyed roles such as Director of Digital Business Strategy and Operations at Warner Bros, International Strategy and Ops @ MySpace and Corp Dev and Strategy @ Yahoo. Emilie has also sat on the Naspers board for the last 10 years.

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In Today’s Episode You Will Learn:

1.) How Emilie made her way into the world of M&A and came to lead over 40+ game-changing acquisitions for Linkedin?

2.) In 2016, M&A made up 95% of startup exits, how does Emilie evaluate the current state of exit environments? What 2 reasons have caused the drop in startup M&A? How does Emilie view the rise of PE and strategic investors to the acquisition markets?

3.) Paul Graham said ‘startups should only talk to corp dev when they are doing really well or really badly’. What are Emilie’s thoughts on when is the right time for startups to have conversations with Corp Dev teams? When does Emilie you most like to begin the relationship? How does Emilie like to work with VCs in this relationship building?

4.) Paul Graham also described the structure of M&A as “grueling”. Does Emilie agree with this? How does Emilie map out the structure of a typical M&A deal, from start to finish? How much of a role does price play in her evaluation of a deal? How does Emilie measure the success of an acquisition?

5.) Matt Switzer @ Hootsuite stated the biggest M&A risk to be integration. What does smooth integrations look like for both consumer vs enterprise? Why do they differ? How can this integration work be de-risked and front loaded?

Items Mentioned In Today’s Show:

Emilie’s Fave Book: The Bonfire of the Vanities 

Emilie’s Most Recent Investment: Heighten

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

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

NatureBox Unlimited snack plans offer all you can eat snacks for one fixed price per employee. Naturebox use simple ingredients you can trust to create bold flavors you can’t find anywhere else. All NatureBox snacks are free from artificial junk and variety is endless with options from sweet or savory to vegan or gluten-free. Simply choose the plan that fits your team’s unique snacking habits and select any of NatureBox’s time-saving add-on’s. And beyond Unlimited snacks, you’ll receive perks such as free kitchen setup, no contracts, a dedicated account manager and more. Simply click here to and use the offer code VC20 to get 20% of your first Naturebox month.

Leesa is the Warby Parker or TOMS shoes of the mattress industry. Leesa have done away with the terrible mattress showroom buying experience by creating a luxury premium foam mattress that is ordered completely online and ships for free to your doorstep. The 10-inch mattress comes in all sizes and is engineered with 3 unique foam layers for a universal, adaptive feel, including 2 inches of memory foam and 2 inches of a really cool latex foam called Avena, design to keep you cool. All Leesa mattresses are 100% US or UK made and for every 10 mattresses they sell, they donate one to a shelter. Go to Leesa.com to start the New Year with better nights sleep!

 

 

Henry Davis is the President and COO @ Glossier, a New York brand that has taken the beauty world by storm. To date they have raised close to $35m in VC funding from some of the best in the business including past guests on the show Kirsten Green @ Forerunner, Index Ventures, IVP and our friends at Thrive. As for Henry, prior to entering the world of beauty and brands with Glossier, he sat on the other side of the table as a VC with Index Ventures in London. Before that, for his sins, Henry spent time in the world of corporate finance with Citi Group.

Crystal Huang is a Principal @ GGV Capital, one of the world’s leading venture firms partnering with entrepreneurs in the world’s largest markets, the US and China. At GGV Crystal led the firm’s investment in Wigo (acquired by Cinemagram) and attends board meetings at Tile and Flightcar. Crystal is also a board member @ NextGen partners, the organization representing the future General Partners within the bay area. Prior to joining GGV, Crystal worked as an analyst in Blackstone’s Technology M&A Advisory Group and due to her immense promise and success already, Crystal has been named to Forbes’ 30 Under 30 Venture Capital.

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In Today’s Episode You Will Learn:

1.) How Crystal made her way into the world of VC from Tech M&A with Blackstone?

2.) How does Crystal view the ongoing debate of operator vs non-operator experience? Does Crystal agree with Pat Grady that the rate of decay on operating experience has never been greater? What elements of operational experience, applied to VC, do stand the test of time?

3.) What does Crystal believe are the 3 key differences when comparing the US and Asian tech markets? How do deal sizes change across geographies? What does this do to the unit economics of the businesses? How does vendor engagement and sales cycles differ?

4.) In a world of Baidu, Alibaba and Tencent quickly acquiring or copying innovative ideas, is there a market for true later stage VC in Asia? Where are the market opportunities? How does incumbent power in Asia differ to incumbent power in the US?

5.) How does Crystal fundamentally see distribution models vary between the US and Asia? Has Asia enjoyed the same rise of the “self-service model” enacted by many in the US? What does this mean for internal org structures and unit economics?

Items Mentioned In Today’s Show:

Crystal’s Fave Book: The Code Book

Crystal’s Most Recent Investment: BitSight

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

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

NatureBox Unlimited snack plans offer all you can eat snacks for one fixed price per employee. Naturebox use simple ingredients you can trust to create bold flavors you can’t find anywhere else. All NatureBox snacks are free from artificial junk and variety is endless with options from sweet or savory to vegan or gluten-free. Simply choose the plan that fits your team’s unique snacking habits and select any of NatureBox’s time-saving add-on’s. And beyond Unlimited snacks, you’ll receive perks such as free kitchen setup, no contracts, a dedicated account manager and more. Simply click here to and use the offer code VC20 to get 20% of your first Naturebox month.

Leesa is the Warby Parker or TOMS shoes of the mattress industry. Leesa have done away with the terrible mattress showroom buying experience by creating a luxury premium foam mattress that is ordered completely online and ships for free to your doorstep. The 10-inch mattress comes in all sizes and is engineered with 3 unique foam layers for a universal, adaptive feel, including 2 inches of memory foam and 2 inches of a really cool latex foam called Avena, design to keep you cool. All Leesa mattresses are 100% US or UK made and for every 10 mattresses they sell, they donate one to a shelter. Go to Leesa.com to start the New Year with better nights sleep!

Hans Tung is a Managing Partner @ GGV Capital, one of the world’s leading venture firms partnering with entrepreneurs in the world’s largest markets, the US and China. Evident when looking at Han’s incredible investments in the likes of Wish, Poshmark, musical.ly, Slack and OfferUp in the US and then Xiaomi, Forgame, and Domob Ads in Asia. Previously, Hans was with Bessemer Venture Partners, where he helped global players such as Skype expand into China. Hans was also a founding member of two pan-Asian internet startups that were subsequently sold to telcos. Due to his incredible success, Hans has been ranked as a top VC on the Forbes Midas list since 2013 and was recognized by The Founder and CBN News magazines in the past as a Top 10 most entrepreneur-friendly VC in China.

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In Today’s Episode You Will Learn:

1.) How Hans made his way into VC with Bessemer having founded and exited 2 prior startups?

2.) Why does Hans believe that the globalisation of consumer mobile companies is the biggest trend in his career? Why is Hans still so attracted to consumer with lacking distribution channel availability and incumbents like Amazon? Have Amazon already won?

3.) What were Hans’ biggest lessons from investing in China that have allowed him to invest better in the US? How does Hans evaluate prior US companies entering strategies into China? How does he analyse Uber’s entering into China?

4.) Hans has backed some of the hottest companies in the business from Airbnb to Wish, how does Hans respond to price sensitivity and having to pay up to get into the round? How does Hans think about the opportunity cost of capital deployment?

5.) Why does Hans remain so bullish on the globalisation of tech? In a world of Trump and Brexit are we not in ever more atomistic times? How does Hans see the convergence of millenial consumers when comparing the US and Asia?

Items Mentioned In Today’s Show:

Hans’ Fave Book: The Information, Stratechery

Hans’ Most Recent Investment: iBotta

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

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

NatureBox Unlimited snack plans offer all you can eat snacks for one fixed price per employee. Naturebox use simple ingredients you can trust to create bold flavors you can’t find anywhere else. All NatureBox snacks are free from artificial junk and variety is endless with options from sweet or savory to vegan or gluten-free. Simply choose the plan that fits your team’s unique snacking habits and select any of NatureBox’s time-saving add-on’s. And beyond Unlimited snacks, you’ll receive perks such as free kitchen setup, no contracts, a dedicated account manager and more. Simply click here to and use the offer code VC20 to get 20% of your first Naturebox month.

Leesa is the Warby Parker or TOMS shoes of the mattress industry. Leesa have done away with the terrible mattress showroom buying experience by creating a luxury premium foam mattress that is ordered completely online and ships for free to your doorstep. The 10-inch mattress comes in all sizes and is engineered with 3 unique foam layers for a universal, adaptive feel, including 2 inches of memory foam and 2 inches of a really cool latex foam called Avena, design to keep you cool. All Leesa mattresses are 100% US or UK made and for every 10 mattresses they sell, they donate one to a shelter. Go to Leesa.com to start the New Year with better nights sleep!

Ben Marcus is the Founder & CEO @ Airmap, the startups that provides everything one needs to unlock and scale drone operations in the ever-changing world of airspace. They have raised over $40m in funding from industry heavyweights Sony, Rakuten, Qualcomm, Airbus Ventures and then also many friends of the show including Semil Shah, Lux Capital, Microsoft Ventures, General Catalyst, BullPen Capital and David Waxman at TenOneTen, just to name a few. Prior to AirMap, Ben co-founded and was CEO of the world’s largest light business jet sales company, Jetaviva and before that started his career as a flight instructor and later became a flight test engineer. Fun fact, Ben is also an FAA-certified Airline Transport Pilot and Flight Instructor with over 4,500 hours of flight experience.

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In Today’s Episode You Will Learn:

1.) How Ben made his way into the world of startups and drones from being a pilot and flight test engineer?

2.) What does Ben think is a strong investment strategy when investing in the drones? What 4 categories present nascent opportunities to Ben? What elements of the tech stack should potential investors further drill down on with potential investments?

3.) Question from Hemant Taneja: How does Ben assess the presence and desires of Amazon and Google with their pre-existing mission to win the airspace? Question from Semil Shah: Does this lead to a world of consolidation and startup M&A by incumbents?

4.) What does Ben believe are the core catalysts that will take drones to 100s of millions of people? How does Ben assess the similarties and differences in serving enterprise vs consumer drone markets? Does Ben agree with Jonathan Downey in his expression that enterprises like “boring” offerings?

5.) How does Ben evaluate the hardware vs software paradigm in the drone market? Does Ben see the commoditisation of drone hardware in the coming years? How does Ben evaluate the likes of DJI with their prominence? Does the weaponisation of drones cause significant alarm for Ben?

Items Mentioned In Today’s Show:

Ben’s Fave Book: The Wealth of Nations

Ben’s Fave Blog: Social Capital Newsletter

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

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

NatureBox Unlimited snack plans offer all you can eat snacks for one fixed price per employee. Naturebox use simple ingredients you can trust to create bold flavors you can’t find anywhere else. All NatureBox snacks are free from artificial junk and variety is endless with options from sweet or savory to vegan or gluten-free. Simply choose the plan that fits your team’s unique snacking habits and select any of NatureBox’s time-saving add-on’s. And beyond Unlimited snacks, you’ll receive perks such as free kitchen setup, no contracts, a dedicated account manager and more. Simply click here to and use the offer code VC20 to get 20% of your first Naturebox month. 

Leesa is the Warby Parker or TOMS shoes of the mattress industry. Leesa have done away with the terrible mattress showroom buying experience by creating a luxury premium foam mattress that is ordered completely online and ships for free to your doorstep. The 10-inch mattress comes in all sizes and is engineered with 3 unique foam layers for a universal, adaptive feel, including 2 inches of memory foam and 2 inches of a really cool latex foam called Avena, design to keep you cool. All Leesa mattresses are 100% US or UK made and for every 10 mattresses they sell, they donate one to a shelter. Go to Leesa.com to start the New Year with better nights sleep!

 

 

Kevin Thau is a General Partner @ Spark Capital, one of the best performing funds of the last decade with a portfolio including the likes of Twitter, Slack, Oculus, Medium, PostMates, Cruise (acq $1Bn) the list goes on. As for Kevin, he has led investments in Medium, LOLA, CTRL Labs, Aura and Haven. Prior to Spark, Kevin enjoyed an incredible 7 years at Twitter, when he joined they had less than 20 employees and 1m users and he carried roles such as Director of Mobile Products and VP of Business & Corporate Development. Before Twitter, Kevin was employee number 7 at Software.com (which became Openwave) where he helped ship the first mobile browser, mobile messaging services and mobile websites.

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In Today’s Episode You Will Learn:

1.) How Kevin made his way into VC with Spark having spent years in operations with Twitter and Silicon Graphics?

2.) What were Kevin’s biggest lessons from watching the hyper-scaling of Twitter? What are the most prominent challenges companies face at this stage? What were his takeaways from working with product visionaries like Jack Dorsey & Sonos’ John MacFarlane?

3.) As an operator turned investor, how does Kevin characterise his approach to working with portfolio companies? What were Kevin’s early VC learnings from his discussions with Fred Wilson and Bijan Sabet on VC profile and psychology?

4.) Why does Kevin believe that VC is a game of “maximizing serendipity”? How does Kevin assess personal time allocation, today as a VC? What has Kevin found most challenging since making the move to VC from operations?

5.) How does Kevin assess the consumer landscape at present? Does Kevin agree with Kirsten Green that “Amazon does more to make the market than crush it”? Why does Kevin find Instagram such a special tool for evaluating brands? What does he look for in the Instagram profiles of these emerging brands that really excites him?

Items Mentioned In Today’s Show:

Kevin’s Fave Book: Moneyball: The Art of Winning An Unfair Game

Kevin’s Most Recent Investment: CTRL-Labs

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

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

NatureBox Unlimited snack plans offer all you can eat snacks for one fixed price per employee. Naturebox use simple ingredients you can trust to create bold flavors you can’t find anywhere else. All NatureBox snacks are free from artificial junk and variety is endless with options from sweet or savory to vegan or gluten-free. Simply choose the plan that fits your team’s unique snacking habits and select any of NatureBox’s time-saving add-on’s. And beyond Unlimited snacks, you’ll receive perks such as free kitchen setup, no contracts, a dedicated account manager and more. Simply click here to and use the offer code VC20 to get 20% of your first Naturebox month. 

Leesa is the Warby Parker or TOMS shoes of the mattress industry. Leesa have done away with the terrible mattress showroom buying experience by creating a luxury premium foam mattress that is ordered completely online and ships for free to your doorstep. The 10-inch mattress comes in all sizes and is engineered with 3 unique foam layers for a universal, adaptive feel, including 2 inches of memory foam and 2 inches of a really cool latex foam called Avena, design to keep you cool. All Leesa mattresses are 100% US or UK made and for every 10 mattresses they sell, they donate one to a shelter. Go to Leesa.com to start the New Year with better nights sleep!