20VC: Lessons Learned Scaling PillPack from Seed to Amazon Acquisition, Why Investors Should Spend More Time Assessing Human Capital Risk Taken by Founders & The Right Way To Think About Capital Efficiency in Scaling with David Frankel, Managing Partner @ Founder Collective


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.



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 HarryThe Twenty Minute VC and David on Twitter here!

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

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20VC: Are VCs Still “Open For Business”, How VCs Attitude To Risk Has Changed & The 2 Most Valuable Assets To Founders Today with Fred Destin, Founding Partner @ Stride VC

Fred Destin is a Founding Partner @ Stride.VC, one of Europe’s newest and largest early-stage seed firms. Prior to co-founding Stride, Fred was a General Partner @ Accel where he was the lead investor and board member at Deliveroo, Pillpack (acq. AMZN for $1BN) and Carwow. Prior to Accel, he was a partner at Atlas Venture (now Accomplice) where he invested in and served on the board of Pillpack, Zoopla (IPO), Secret Escapes, Integral Ad Science (partial exit to Vista at $850M) and TheCurrencyCloud to name a few. Fun fact, his portfolio has a total enterprise value of more than $10BN and he generated in excess of $700M in exit value to investors.



In Today’s Episode You Will Learn:

1.) How did Fred make his way into the world of venture and come to co-found one of Europe’s newest and largest seed funds in Stride.VC?

2.) If you look to Twitter, all VCs are “open for business”, does Fred really believe the market is still open for business? How will deal volume be affected? How bad does Fred think this could get? How does this downturn compare to that of the dot-com and 2008?

3.) Why did Stride decide to take the decision to pause on investing at this moment in time? How does Fred respond to the suggestion of better pricing and less competition at this time? How does Fred believe venture investors view of risk evolves at this time? What is the first to change?

4.) With many new funds deploying their first fund in 18 months, does Fred think we will see a gravyard of new fund managers out of cash and with cash hungry portfolios? What advice does Fred give to newer managers of other elements they have to be minfdul/aware of?

5.) How does Fred think about the right way for managers to communicate with their LPs at this time? What has Stride done that has worked? Does Fred believe we will see many LPs defaulting on their initial commitments? How does Fred think emerging managers can navigate this?

Items Mentioned In Today’s Show:

Fred’s Fave Movie: Mulholland Drive

Fred’s Most Recent Investment: Collective Benefits

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

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

20VC: BoxGroup’s David Tisch on Whether Concentrated Investing At Seed Works, Do Founders Really Want Direct Feedback and Is It Good For Them & Why Consumer Social Is Interesting Again

David Tisch Headshot

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



In Today’s Episode You Will Learn:

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

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

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

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

Items Mentioned In Today’s Show:

David’s Fave TV Show: Survivor

As always you can follow HarryThe Twenty Minute VC and David on Twitter here!

20VC: Techstars Founder David Cohen on Why Seed Investing Is A Different Asset Class To Venture, What Makes The Best And The Worst Board Members & Why Every Company Has To Have A Pessimist In The Room


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.



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 HarryThe Twenty Minute VC and David on Twitter here!

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

20VC: Stride’s Fred Destin on Acceptable vs Non-Acceptable Risks When Investing, How Startup Founders Can Improve The Quality of Their Decision-Making & Why Plans Do Not Matter and No Board Member Should Bash An Entrepreneur For Missing Their Numbers

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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.



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 HarryThe Twenty Minute VC and Fred on Twitter here!

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

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20VC: Why Partners Are There To Save Each Other From Themselves, Why Effective Reserve Allocation Is The Hardest Question In Venture & What Makes The Truly Special Board Members with Jeff Fagnan, Founding Partner @ Accomplice


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.



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.

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20VC: Why Founders Should Not Focus On Top Line Valuation, Why Capital Efficiency Is Key To Returns And Investment Success & Why Despite Popular Thought, $100m Is An Exciting Exit For VC with Micah Rosenbloom, Managing Partner @ Founder Collective

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Micah Rosenbloom is Managing Partner @ Founder Collective, one of the leading seed funds in the world with investments in Uber, Buzzfeed, Makerbot, PillPack, Coupang and Cruise, just to name a few. As for Micah, prior to VC with Founder Collective, his career was varied starting as a Hollywood agent before becoming a serial entrepreneur founding 3 companies with the last, a successful exit alongside his now Partner Eric Paley with Brontes Technology. Micah also is a Board Member with Sequoia Funded Dia and Co and board observer with both MoveWith and Sense360.



In Today’s Episode You Will Learn:

1.) How Micah made the move from Hollywood agent to leading seed stage VC?

2.) Why does Micah believe it is wrong to have themes to invest against? Why does he believe that the most interesting businesses can be found in weird and wonderful places?

3.) Why does Micah believe it is a problem for founders to focus exclusively on top line valuation? Why does Micah disagree with the common notion that a $100m exit is not exciting for VC?

4.) Why does Micah believe it is wrong for founders to build their company for the next round? Why does Micah disagree with Jason Lemkin in stating, ‘the best investors know the benchmarks clearly for the next round’.

5.) How does Micah deal with the fire hose of activities inherent within venture? How does he prioritise those activities? What thesis does he base all his decisions around?

Items Mentioned In Today’s Show:

Micah’s Fave Book: Thinking Fast and Slow

Micah’s Most Recent Investment: Skysafe

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

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

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