The Twenty Minute VCAvi Eyal: Making $2.3BN on Monday, Stripe & PillPack from Entrée Capital MP | E1173
Episode Details
EPISODE INFO
- Released
- July 3, 2024
- Duration
- 1h 5m
- Channel
- The Twenty Minute VC
- Watch on YouTube
- ▶ Open ↗
EPISODE DESCRIPTION
*The content here is for informational purposes only; should not be taken as legal, business, tax, or investment advice or be used to evaluate any investment or security; and is not directed at any investors or potential investors.* ----------------------------------------------- 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. ----------------------------------------------- Timestamps: (00:00) Intro (00:51) Impactful Childhood Hardship (01:51) Luck vs Skill in Achieving Success (03:39) The Speed of Conviction in Venture Capital (05:22) Sustaining Companies Through Financial Droughts (06:34) Insiders vs. Outsiders To a Market (10:10) Navigating VC Competition in Angel Deals (12:29) Concentrating Capital in Successful Startups (15:15) Navigating Price Sensitivity & Valuation Discipline (21:27) Strategic Approaches to Competitive Markets (23:58) The Monday.com Success: Defying Market Skepticism (30:24) Lessons on Settling Down: Timing & Approach (33:26) Avi's Strategy for Selling Stripe Positions (38:48) VCs' Pre-Product-Market-Fit Role (41:14) Avi’s Biggest Investing Mistake (48:02) Sourcing, Selecting, & Servicing (50:13) Learning from Misses (53:37) Advocating for Israel & Countering Anti-Semitism (01:00:37) Prospect on Long-term Palestinian-Israeli Relations (01:02:57) Quick-Fire Round ----------------------------------------------- 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?
1. 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?
1. The Biggest Hits and Biggest Misses: Monday: How did Avi build such a large position in Monday over time? How did a Series A lead dropping out leading to a $250M gain for Entree? Stripe: Avi has now sold all 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: Avi made $15M from PillPack’s exit. What did that teach Avi about ownership? Cazoo: How was Avi the only one to make money from Cazoo? How did Avi’s sell strategy help him make millions when everyone else did not sell? ----------------------------------------------- Subscribe on Spotify: https://open.spotify.com/show/3j2KMcZTtgTNBKwtZBMHvl?si=85bc9196860e4466 Subscribe on Apple Podcasts: https://podcasts.apple.com/us/podcast/the-twenty-minute-vc-20vc-venture-capital-startup/id958230465 Follow Harry Stebbings on Twitter: https://twitter.com/HarryStebbings Follow Avi Eyal on Twitter: https://twitter.com/aeyal1 Follow 20VC on Instagram: https://www.instagram.com/20vchq Follow 20VC on TikTok: https://www.tiktok.com/@20vc_tok Visit our Website: https://www.20vc.com Subscribe to our Newsletter: https://www.thetwentyminutevc.com/contact ----------------------------------------------- #20vc #harrystebbings #avieyal #enreecapital #venturecapital #founder #ceo #mondaycom #stripe #cazoo #pillpack
SPEAKERS
Avi Eyal
guestHarry Stebbings
host
EPISODE SUMMARY
In this episode of The Twenty Minute VC, featuring Avi Eyal and Harry Stebbings, Avi Eyal: Making $2.3BN on Monday, Stripe & PillPack from Entrée Capital MP | E1173 explores avi Eyal Reveals Monday.com Windfall, Venture Discipline, And Zionism Avi Eyal, co-founder of Entrée Capital, breaks down how a $15M total investment in monday.com turned into over $1.5B in distributions and why one extreme outlier can outweigh a decade of other wins. He explains Entrée’s disciplined, concentrated approach to early-stage venture: a small number of core and “angel” positions, strict rules for selling, and deep, hands-on involvement with founders pre–product-market fit. Eyal outlines his investment framework (technology + TAM to the power of team, multiplied by timing), his aversion to over-capitalized, overvalued rounds, and how he thinks about ownership, signaling risk, and follow-ons in an era of institutionalized mega-funds. The conversation ends with his views on Israel’s political crisis, antisemitism, and the need for a new generation of leadership and moral renewal.
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