20VC: Turning a $15M Investment in Monday into $1.5BN in Cash | The Strategy Behind a 37x DPI $45M Fund | The Three Step Process to Selling Positions that has Netted Top Percentile Returns with Avi Eyal, Co-Founder @ Entrée Capital

20VC: Turning a $15M Investment in Monday into $1.5BN in Cash | The Strategy Behind a 37x DPI $45M Fund | The Three Step Process to Selling Positions that has Netted Top Percentile Returns with Avi Eyal, Co-Founder @ Entrée Capital

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?

Avsnitt(1398)

20VC's Big Fat Quiz of the Year: Founder, Fund and Breakout Company of 2025 | Predictions for 2026: The Company to Buy, The Biggest Short | Why Salesforce Could Win 2026 and The Tailwinds NVIDIA Will Face

20VC's Big Fat Quiz of the Year: Founder, Fund and Breakout Company of 2025 | Predictions for 2026: The Company to Buy, The Biggest Short | Why Salesforce Could Win 2026 and The Tailwinds NVIDIA Will Face

AGENDA: 03:48 Founder of the Year 2025 06:58 Product of the Year 10:05 Fund of the Year 20:52 Breakout Companies of 2025: Who Made the Biggest Impact? 26:57 Biggest Surprises of 2025 32:57 Predictions for 2026: Top Performing Tech Stocks of the Year 35:25 B2B Stocks to Watch 38:31 Why Salesforce Could Be the Buy of 2026 47:11 Google, Meta, Apple, NVIDIA, Microsoft: Buy One, Short One 55:38 IPO Speculations: Who Will Go Public in 2026 01:00:57 The Impact of AI on Employment

22 Dec 1h 9min

20Product: On Running's CPO on How to Create Emotion Through Product | Why 99% of Products Fail and How to Create Cults Around Products | The Biggest Product Mistakes On Have Made & Lessons Learned with Gérald Marolf

20Product: On Running's CPO on How to Create Emotion Through Product | Why 99% of Products Fail and How to Create Cults Around Products | The Biggest Product Mistakes On Have Made & Lessons Learned with Gérald Marolf

Gérald Marolf is the Chief Product Officer at On Running. Gérald oversees the full range of On's shoes, apparel and accessories to make sure each delivers performance, comfort and style. Before On, Gérald spent over a decade building consumer brands with collaborators such as Microsoft and Ferrari. AGENDA: 00:00 – Why Most "Great Products" Fail to Create Emotion 03:00 – How Perfume Taught Me Everything About Desire & Product 06:10 – The Brutal Reality of Building Physical vs Digital Products 16:00 – Why "Simple Design" Is Overrated and Dangerous 23:00 – Why Vuori is the Brand to Short in Consumer  28:30 – The Biggest Product Mistake: Listening to Customers Too Much 32:10 – On Only Do Tennis Because of Roger Federer 38:30 – Were We Too Late to Marathon Running? A Painful Admission 43:40 – The Most Controversial Product On Has Ever Launched 49:00 – Are Counterfeits Good or Bad in Fashion?

19 Dec 56min

20VC: Will SpaceX IPO at $1.5TRN | Will Cursor Kill Figma | Lightspeed Raises $9BN | OpenAI: $1BN from Disney, New CRO & #1 App in App Store | Oracle and Broadcom Hit: Now the Time to Buy?

20VC: Will SpaceX IPO at $1.5TRN | Will Cursor Kill Figma | Lightspeed Raises $9BN | OpenAI: $1BN from Disney, New CRO & #1 App in App Store | Oracle and Broadcom Hit: Now the Time to Buy?

AGENDA: 03:32 Lightspeed's $9 Billion Fundraise 05:20 The Impact of Mega Funds on Seed VCs 10:09 The Supercycle of Growth and Late-Stage Investments 13:06 Disney Invests $1BN into OpenAI and What It Means 23:19 Oracle Hit Hard: Is Now the Time to Buy 28:34 Broadcom's Market Cap Drop and Anthropic's AI Chip Orders 35:04 Cursor Competes with Figma: The Convergence of Design and Coding Tools 46:20 The Biggest Danger for Incumbents: Being Maimed by AI 55:28 Boom Supersonic Raising $300M to… Power Data Centres… WTF 01:00:24 Will SpaceX IPO at $1.5TRN and The Elon Option Value

18 Dec 1h 22min

20VC: a16z's David George on How $BN Funds Can 5×, Do Margins & Revenue Matter in AI & the Most Controversial Bet at a16z

20VC: a16z's David George on How $BN Funds Can 5×, Do Margins & Revenue Matter in AI & the Most Controversial Bet at a16z

David George is a General Partner at Andreessen Horowitz, where he leads the firm's Growth investing team. His team has backed many of the defining companies of this era, including Databricks, Figma, Stripe, SpaceX, Anduril, and OpenAI, and is now investing behind a new generation of AI startups like Cursor, Harvey, and Abridge. AGENDA: 03:05 – Why Everyone is Wrong: Mega Funds Does Not Reduce Returns 10:40 – Is Public Market Capital Actually Cheaper Than Private Capital? 18:55 – The Biggest Advantage of Staying Private for Longer 23:30 – The #1 Investing Rule for a16z: Always Invest in the Founder's Strength of Strengths 31:20 – Why Fear of Theoretical Competition Makes Investors Miss Great Companies 35:10 – Does Revenue Matter as Much in a World of AI? 44:10 – Does Kingmaking Still Exist in Venture Capital Today? 49:20 – Do Margins Matter Less Than Ever in an AI-First World? 53:50 – My Biggest Miss: Anthropic and What I Learn From it?  56:30 – Has OpenAI Won Consumer AI? Will Anthropic Win Enterprise? 59:45 – The Most Controversial Decision in Andreessen Horowitz History 1:01:30 – Why Did You Invest $300M into Adam Neumann and Flow?

15 Dec 1h 6min

20Growth: How Wiz Built a $30BN Brand in Enterprise | What Worked vs What Was a Mega Failure: Lessons Learned | Why Marketers Make the Worst CMOs & What To Look for in Growth with Raaz Herzberg

20Growth: How Wiz Built a $30BN Brand in Enterprise | What Worked vs What Was a Mega Failure: Lessons Learned | Why Marketers Make the Worst CMOs & What To Look for in Growth with Raaz Herzberg

Raaz Herberg is the Chief Marketing Officer and VP Product Strategy at Wiz, the fastest-growing cloud security company in history. As one of the first 10 employees, Raaz has helped scale the business from nothing to a multi-billion-dollar ARR business. Before Wiz, Raaz was a Senior PM working on Azure at Microsoft.  AGENDA: 03:51 What No One Knows About The Early Wiz Days 09:08 Most Effective Marketing Wiz Ever Did? Lessons from it? 24:11 How Wiz Mastered Enterprise Sales and Product Development 39:12 The Value of Proof of Concept an Why Everyone Gets Them Wrong 44:23 Why The Best Leaders Give More Equity Than They Should 52:55 The Impact of COVID on Business Operations 01:01:33 What in AI is No One Talking About That Everyone Should Be? 01:07:29 Why Does Raaz Think Custom Tools Will Dominate the Enterprise?

12 Dec 1h 16min

20VC OGs: SpaceX Valued at $800BN & Harvey Raises $160M at an $8BN Price | Airwallex Raises $330M and The Battle with Keith Rabois | Netflix Acquires Warner Brothers | IPO Market Predictions for 2026: Anthropic, Stripe, Databricks and SpaceX

20VC OGs: SpaceX Valued at $800BN & Harvey Raises $160M at an $8BN Price | Airwallex Raises $330M and The Battle with Keith Rabois | Netflix Acquires Warner Brothers | IPO Market Predictions for 2026: Anthropic, Stripe, Databricks and SpaceX

AGENDA: 03:46 SpaceX's $800 Billion Valuation: A Deep Dive 09:18 IPO Market Predictions for 2026 18:18 Netflix's Bold Move: Acquiring Warner Brothers 27:43 Tiger's New Fund Strategy 33:02 Databricks' Head of AI $500 Million Seed Round 36:38 Harvey Raises $160M at an $8BN Valuation 48:22 Will LLMs Kill the App Layer 01:02:02 Google's AI Capabilities 01:06:58 Chinese Open Source Models in US Startups 01:08:57 Airwallex Raises $330M at an $8BN Valuation 01:23:50 Prediction Markets and Insider Trading

11 Dec 1h 31min

20VC: Kalshi's $1BN Raise, the Polymarket Feud, and the Battle to Replace Traditional Media

20VC: Kalshi's $1BN Raise, the Polymarket Feud, and the Battle to Replace Traditional Media

Tarek Mansour is the Co-Founder and CEO @ Kalshi, the leader in the world of prediction markets. Just last week, they announced their $1BN raise at an $11BN valuation. In total, they have raised $1.59BN from some of the best, including Sequoia, a16z, General Catalyst, IVP, Meritech, and more. They also last week announced exclusive partnerships with CNN and CNBC, marking their move into mainstream media and news.  AGENDA: 03:28 Why Did Kalshi Need to Raise $1BN 10:35 Why is Kalshi vs Polymarket Such a Fierce Rivalry? 20:44 The Future of Prediction Markets 25:09 Why Does Kalshi Partner with CNN When They Could Replace Them? 26:27 Why Did Tarek Fight For the Rights of his Early Investors So Much? 27:25 What Makes Alfred Lin The Best? 29:19 Does Having Sequoia as an Investor Change the Game? 36:58 Are Teenage Founders Today Emotionally Ready to Lead Companies 38:30 Quick Fire Round: Celebrity Investors, Relationships with Parents

8 Dec 47min

20VC: Inside Bending Spoons Acquisition Machine: Evernote, Eventbrite, Vimeo | How Evernote Evaluates Acquisitions and New Product Ideas | How Evernote Mastered Product Launches, User Retention and Monetisation with Federico Simionato

20VC: Inside Bending Spoons Acquisition Machine: Evernote, Eventbrite, Vimeo | How Evernote Evaluates Acquisitions and New Product Ideas | How Evernote Mastered Product Launches, User Retention and Monetisation with Federico Simionato

Bending Spoons is the acquisition machine of the tech world. They have acquired the likes of Evernote, Vimeo, Eventbrite, Streamyard and more. However, they never open their gates to the secrets behind Evernote's product machine. Today that changes with Federico Simionato joining 20Product. Fede has been a Product Lead at Bending Spoons for 8 years where he has led product teams at Evernote, WeTransfer and more.   AGENDA: 03:02 From Dentist Games to $11BN Bending Spoons 04:54 Advice for Aspiring Product Managers 05:38 Building a Coveted Brand at Bending Spoons 07:43 Evaluating and Testing New Product Ideas 13:35 How Evernote has Mastered User Retention 25:24 The Impact of AI on Product Design and Prototyping 31:19 How Bending Spoons Does Product Launches and Lessons Learned 33:27 How Every Product Team Should Do Monthly Updates to Users 36:38 Recording and Transparency in Updates 38:06 Lessons from Failed Product Launches 45:14 Structuring Teams and Acquisitions 47:12 Monetization Strategies and Push Notifications 57:21 Quick Fire Round: Insights and Reflections

5 Dec 1h 5min

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