Podcast
Harry Stebbings | Entrepreneur | Investor | Blogger
The Twenty Minute VC (20VC) interviews the world's greatest venture capitalists with prior guests including Sequoia's Doug Leone and Benchmark's Bill Gurley. Once per week, 20VC Host, Harry Stebbings is also joined by one of the great founders of our time with prior founder episodes from Spotify's Daniel Ek, Linkedin's Reid Hoffman, and Snowf
Avi Eyal is Co-Founder and Managing Partner of Entrée Capital, an early-stage VC fund with a portfolio including the likes of Monday.com, Stripe, Coupang, PillPack, and Snap. From their $15M investment into Monday, Entrée distributed a whopping $1.5BN, one of their $45M funds is a whopping 37x DPI. Avi is one of the greatest venture investors you might not have heard about. In Today's Episode with Avi Eyal We Discuss: 1. The Biggest BS "Rules" in Venture Capital: Why does Avi believe that it is BS for every deal to need to be a homerun and return the fund? Why does Avi believe that signalling is real and it is BS to suggest otherwise? Why does Avi believe that it is BS that ownership is crucial to make mega venture returns? Why does Avi believe that you do not have to win every deal to be one of the best in venture? Why should venture investors not manage the positions of their companies when they go public? Why is it BS to think they have asymmetric information when the company goes public? 2. What Makes the Best Founders: Does Avi prefer first or second time entrepreneurs? Why? Would Avi rather back a founder that is an expert in a market or one that is new to a market and has the naivety to not know what is hard? Are the best CEOs the best fundraisers? How does Avi rank the following when investing; team, market, traction and technology? When Avi has misread a founder, what was it that he missed? 3. The Biggest Hits and Biggest Misses: Monday: How did Entrée build such a large position in Monday over time? How did a Series A lead dropping out leading to a $1.5BN gain for Entree? Stripe: Entrée has now 50% of his Stripe position. Why? What is the three step process for Avi in selling positions? How does he know when to and what is the right amount? PillPack: Entrée made $15M from PillPack's exit. What did that teach Avi about ownership? Cazoo: How was Entrée the only one to make money from Cazoo? How did Entrée's sell strategy help him make millions when everyone else did not sell?
Jul 3
58 min 33 sec
Avi Eyal is Co-Founder and Managing Partner of Entrée Capital, an early-stage VC fund with a portfolio including the likes of Monday.com, Stripe, Coupang, PillPack, and Snap. From their $15M investment into Monday, Entrée distributed a whopping $1.5BN, one of their $45M funds is a whopping 37x DPI. Avi is one of the greatest venture investors you might not have heard about. In Today's Episode with Avi Eyal We Discuss: 1. The Biggest BS "Rules" in Venture Capital: Why does Avi believe that it is BS for every deal to need to be a homerun and return the fund? Why does Avi believe that signalling is real and it is BS to suggest otherwise? Why does Avi believe that it is BS that ownership is crucial to make mega venture returns? Why does Avi believe that you do not have to win every deal to be one of the best in venture? Why should venture investors not manage the positions of their companies when they go public? Why is it BS to think they have asymmetric information when the company goes public? 2. What Makes the Best Founders: Does Avi prefer first or second time entrepreneurs? Why? Would Avi rather back a founder that is an expert in a market or one that is new to a market and has the naivety to not know what is hard? Are the best CEOs the best fundraisers? How does Avi rank the following when investing; team, market, traction and technology? When Avi has misread a founder, what was it that he missed? 3. The Biggest Hits and Biggest Misses: Monday: How did Entrée build such a large position in Monday over time? How did a Series A lead dropping out leading to a $1.5BN gain for Entree? Stripe: Entrée has now 50% of his Stripe position. Why? What is the three step process for Avi in selling positions? How does he know when to and what is the right amount? PillPack: Entrée made $15M from PillPack's exit. What did that teach Avi about ownership? Cazoo: How was Entrée the only one to make money from Cazoo? How did Entrée's sell strategy help him make millions when everyone else did not sell?
Jul 3
58 min 33 sec
Matt Clifford is the Co-Founder of Entrepreneur First (EF), the leading global talent investor and incubator. EF has incubated startups worth over $10bn, including Cleo, Tractable and Aztec Protocol. Matt is also Chair of ARIA, the UK’s Advanced Research and Invention Agency, and advises the UK government on AI and in 2023 served as the Prime Minister’s Representative for the AI Safety Summit at Bletchley Park. In Today's Episode with Matt Clifford We Discuss: 1. The Most Important Questions in AI: Are we seeing diminishing returns where more compute does not lead to a significant increase in performance? What is required to reach a new S curve? What do we need to see in GPT 5? Why does Matt believe that search is one of the biggest opportunities in AI today? 2. The Biggest Opportunities in AI Today: How does Matt see the future for society with a world of autonomous agents? What is the single biggest opportunity around agents that no one has solved? Is society ready for agentic behaviours to replace the core of human labour? How does warfare change in a world of AI? Does AI favour states and good actors or criminals and bad actors more favourably when it comes to offence and defence? 3. China and the Race to Win the AI War: Does Matt believe that China are two years behind the US in terms of AI capability? What are Matt's biggest lessons from spending time with the CPP in China working on AI policy? In what way is the CCP more sophisticated in their thinking on AI than people think? What is the bull and the bear case for China in the race for AI? What is the core impact of US export controls on chips for China's ability to build in AI? Does a Trump vs a Biden election change the playing field with China? 4. What Makes Truly Great Founders: Does Matt agree that the best founders always start an entrepreneurial activity when they are young? What is more important the biggest strength of one of the founders or the combined skills of the founding team? What did EF believe about founders and founder chemistry that they no longer believe? Does Matt believe that everyone can be a founder? What are the two core traits required?
Jul 1
1 hr 2 min
Samir Vasavada is the Co-Founder & CEO of Vise, a technology-powered asset manager. Samir and his co-founder, Runik founded Vise from the Midwest at 16 years old. They bootstrapped the company before dropping out of high school and raising $128M in just 6 months from some of the best including Sequoia Capital and Founders Fund. The company achieved unicorn status when the pair turned 20 years old, making them the youngest founders of a $BN company at the time. In Today's Episode with Samir Vasavada We Discuss: 1. The Biggest Hiring Mistakes That Broke Us: Why is hiring people who come with a playbook one of the most damaging things you can do? Why is it impossible to build a remote company that performs the same as in person? Why is it the worst thing to hire people who have a reputation they are obsessed with maintaining? Why do you never want to hire people who join because of who your investors are? Why does Samir regret not firing people faster? How much time is enough time to know? Why is hiring in a hot market one of the most dangerous things you can do? 2. Fundraising: 3 Rounds and $126M in 6 Months: Does Samir regret raising so much money so soon in the company life? What did Samir do that he regrets doing, having had so much money so early? How did the need for free food at an event lead to a term sheet and $50M from Sequoia? Did Samir feel that he could talk to investors when things were going really badly? Why does Samir believe that liquidation preference matters more than valuation? 3. The Depression, The Pressure and Wisdom From Jensen Huang: What did Jensen Huang teach Samir when it comes to wealth and leadership? How did Samir deal with the pressure of raising $126M in 6 months and being the youngest unicorn founder, ever at the time? Was Samir hurt when people he thought were his friends, no longer stuck with him when the company was no longer "hot"? What was Samir's darkest time? How did he overcome and get out of it? Does Samir blame his parents for the pressure they put on him from such a young age?
Jun 28
59 min 8 sec left
Andrew Bialecki is the Co-Founder and CEO of Klaviyo, the platform that powers smarter digital relationships for businesses and their data. To date, Klaviyo has raised over $778M from the likes of Accel, Summit Partners, Sands Capital, and Shopify, and raised an additional $700M after its IPO in September 2023. In Today’s Episode with Andrew Bialecki We Discuss: Founding a $6.23BN Machine in Klaviyo: The Aha Moment What was the aha moment for Klaviyo? How important does Andrew think it is for founders to stick with their initial vision vs when is the right time to pivot? Does a great product sell itself? If you build it, will they come? Bootstrapping Klaviyo: Would it Have Worked with More VC Cash Earlier? Why did Andrew decide to bootstrap & not take VC money with Klaviyo? Does Andrew think Klaviyo would have been successful if they raised a seed round? What would they have done differently? Why does Andrew believe companies should take their time to find product-market fit? What are the most common mistakes founders make? What is Andrew’s advice to founders on fundraising? When did Andrew decide to raise a seed round when he did? How to IPO in an IPO Winter: Advice & Lessons Why did Andrew decide to take Klaviyo public in a bad public market? How was the IPO roadshow process? What were Andrew’s lessons from it? How has Andrew’s role as CEO changed after taking Klaviyo public? Does Andrew think Klaviyo is undervalued today? What is Andrew’s advice to founders on secondaries? Behind the Shopify Partnership How did Klaviyo’s partnership with Shopify happen? What were Andrew’s lessons working with Tobi Lütke & Harley Finklestein? How does Andrew define a win-win partnership? What does Andrew mean by “Partnerships are like a tug of war?” What does Andrew think are the most common reasons partnerships go sideways?