20VC: The Wild Story Raising $450M From Masa and Softbank | Why My Biggest Mistakes Came From Listening to VCs | Why 100 VCs Turned Us Down | Why European Founders Are Tougher Than US Founders with Johannes Reck, GetYourGuide
The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch
Release Date: 06/23/2025
20VC: a16z's Martin Casado on Anthropic vs OpenAI: Where Value Accrues | Cursor vs Replit vs Lovable: Who Wins and Who Loses | The One Sin in AI Investing | Why Open Source is a National Security Risk with China
The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch
Martin Casado is a General Partner @ a16z where he leads the firms $1.25BN infrastructure fund. At a16z, Martin has led investments in companies like Cursor, dbt Labs, and Fivetran to name a few. Before joining a16z, he co-founded Nicira, acquired by VMware for $1.26B. At VMware, he served as CTO of Networking. Widely regarded as a visionary in enterprise infrastructure, Martin has helped shape the modern cloud computing stack. Agenda: 00:00 – Analysis of Current AI Investment Landscape 04:45 – Will Anthropic Kill the AI App Layer? 09:20 – “The Oligopoly Is Coming—Just Like Cloud”...
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20Product: Should We Kill the PM Role Entirely | How Does Product Design Change Most in a World of AI | How Do Monzo Build Product Today: What Works, What Does Not | Why Most Product Sucks and What Makes Truly Great Product
The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch
Fernando Fanton is one of the most respected product leaders in Europe, having held Chief Product Officer roles at Monzo and Just Eat. He previously led product and tech at Rappi, one of Latin America's most valuable startups. Today, Fernando is the CPO @ Property Finder; one of the biggest breakout unicorns from MENA. Agenda: 00:00 – Is “having a vision” actually killing great product teams? 03:15 – Why do most products suck—and what separates the great ones? 07:20 – Should we kill the PM role entirely? Fernando says maybe. 11:45 – Is Monzo’s obsession with trust more...
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20VC: Lovable Raises at $2BN & Hits $100M ARR | Is Cursor Worth $28BN at $1BN in ARR | How Do All Providers Deal with Anthropic Dependency Risk | Are Seed Funds F******: Have Mega Funds Won | Figma IPO Breakdown: Where Does it Price?
The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch
Agenda: 00:00 – Did Jason Just Kill Replit? 03:45 – Why Claude Lies To You and Cannot Be Trusted 06:50 – You Cannot Trust Agents. Period. 10:20 – Why Windsurf Was Dead Without Claude 12:30 – Cursor vs. Lovable: What’s the Better Bet? 14:40 – Should You Still Invest in Cursor at $28B? 18:05 – Would You Bet on Anthropic at $100B or OpenAI at $300B? 24:15 – Inside OpenAI’s Secret Weapon: The Calvin French-Owen Memo 27:50 – Perplexity Just Crushed ChatGPT and Claude 32:15 – Will Cursor Build Their Own Models Before Anthropic Cuts Them Off? 33:20 – Figma’s IPO at...
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20VC: Scaling to $1BN+ in Revenue with No Funding: Surge AI | The Most Insane Scaling Story in Tech |
The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch
Edwin Chen is the Founder and CEO of Surge. Founded in 2020, Surge has scaled to $1BN+ in revenue with zero external funding. At the same time, their competitor, raised over $1.3BN to reach $850M ARR. Today, Surge have the world’s largest model providers as customers and have just 120 employees. Agenda: 00:00 — “Everyone Else Is Just a Body Shop” — Edwin Calls Out the Whole Industry 01:05 — Why 90% of Big Tech Is Wasting Time on Useless Problems 03:45 — “I Don’t Do 1-on-1s” — How Surge Kills Meetings and Still Moves 10x Faster 05:55 — Will a Single Person Build a...
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20VC: Cognition CEO Scott Wu on Acquiring Windsurf: The Process, The Deal, The Rationale | Did Google Overlook a Goldmine in the Core Asset and Did Founders Leave a Sinking Ship | How Cursor and Cognition Deal with Ever Increasing Reliance on Anthropic
The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch
Scott Wu is the co-founder and CEO of Cognition, the company behind Devin, the world’s first AI software engineer. On Friday last week they pulled off the acquisition of the year, acquiring Windsurf, following their licensing agreement with Google. Previously a world-class competitive programmer, he was a gold medalist at the International Olympiad in Informatics and a member of the U.S. Math and Physics Olympiad teams. Before Cognition, he was a founding engineer at Scale AI, helping shape the early AI infrastructure stack. AGENDA: 00:00 – Why are founders walking away instead of going...
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20VC: Windsurf x Google x Cognition: Full Breakdown: Who Made Money, Who Did Not | Lovable vs Replit: Will These Be $100BN Businesses | Why Elon Could Beat Sam Altman with the New Grok | Why Every S&P 500 Company Will Buy Bitcoin?
The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch
Agenda: 00:00 Windsurf was dead—then this deal changed everything 05:00 The Windsurf x Google x Cognition saga explained 09:00 The OpenAI deal collapsed—what really happened 15:00 FTC rules forced a brutal deal structure—who lost? 17:00 The investors’ returns: who actually made money? 21:30 Will Google’s corp dev team get fired over this? 23:00 Cognition’s genius $220M acquisition of Windsurf: Most brilliant Deal of the Year 26:00 The biggest recruiting flex in Silicon Valley this year 35:00 “Roll your own SaaS” is complete nonsense 38:00 Lovable vs Cursor vs Replit: who wins...
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20VC: Vlad Tenev on Robinhood’s $85BN Resurgence | Tokenizing SpaceX & OpenAI | Building Nine Revenue Lines Over $100M | Why Crypto Will Be Robinhood's Biggest Revenue Line | Why Stablecoins Will Replace Banking Rails
The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch
Vlad Tenev is the Founder and CEO of Robinhood, the greatest story on Wall St of the last decade. In the previous 18 months, Robinhood has increased its net revenue by 58% to nearly $3B; a $500M loss in 2023 turned into a $1.1B profit in 2024. Robinhood’s stock is up roughly 4x, lifting their market cap to north of $80B. Today, Robinhood has nine lines of business that do over $100M in revenue. Agenda: 00:00 – “Tokenization Is The Biggest Innovation in Finance” 03:28 – How Robinhood 4x’d Its Market Cap in 8 Months 06:40 – AI Writes 50% of All Net New Code at Robinhood...
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20Growth: The Death of Growth Teams? | How Hubspot Use AI to Triple Email Conversion | The Future of AI SEO | Why Prompt Engineering is the New Coding | What Every CMO Needs to Know About AI in 2025
The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch
Kieran Flanagan is the CMO at HubSpot, where he’s led the transformation of their growth strategy from SEO-led to multi-channel and AI-powered. Formerly SVP of Marketing, he helped scale HubSpot’s user base to millions and revenue past $2B. Before HubSpot, he drove breakout growth at Marketo and Salesforce. Kieran is one of the most respected voices in SaaS marketing and a pioneer in growth-driven content strategy. Agenda: 00:03 – The Death of Growth Teams? Kieran's Wild Prediction 06:44 – AI Innovation Pods: The New Org Structure for Startups 10:18 – Email Personalization That...
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20VC: Daniel Gross and Nat Friedman: Acquired by Meta | OpenAI’s SBC Bombshell: More Stock Comp Than Revenue | Privat Equity is Back: Olo Bought for $2BN | Microsoft Lays Off 9,000 People: Is This Just the Start | Will Sequoia Part with Shaun Maguire
The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch
Agenda: [00:00] The AI Talent Crisis No One’s Ready For [03:00] Daniel Gross and Nat Friedman: Why Two Legendary VCs Walked Away From $1B to Join Meta [12:00] Meta’s AI Talent Magnet: Will It Actually Work? [15:00] Cursor Is Breaking the Market: Can Anyone Compete? [18:30] OpenAI’s SBC Bombshell: More Stock Comp Than Revenue [22:00] CoreWeave’s Power Play: Buying Their Landlords [26:00] Is Circle Next to Go Shopping with Meme Equity? [28:00] PE Is Back: The Olo Take-Private Explained [35:00] Why Triple, Triple, Double, Double Is No Longer Sexy [41:00] QSBS Hack: The Billionaire’s Tax...
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20VC: Scott Galloway on Are Billionaires Happy & The Impact of Money on Psychology and Self-Worth | Becoming a Better Father & Husband | Why We Should Drink More and Not Work From Home | The Tinder Effect & How it Makes Young Men Radical
The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch
Scott Galloway is a Professor of Marketing at NYU Stern, where he’s taught for over two decades. He’s the founder of several successful companies, including L2 (acquired by Gartner for over $150M), Red Envelope, and Prophet. He’s a New York Times bestselling author of four books on business and tech, and co-hosts the award-winning Pivot podcast. Galloway also serves on the boards of The New York Times Company and Panera, and his public talks have been viewed tens of millions of times globally. In Today’s Episode We Discuss: 02:00 – How to Win in a New Economy of AI 06:00 – Should...
info_outlineJohannes Reck is the Founder and CEO of GetYourGuide, the $2BN company that started with a holiday to China and nothing to do. For the first two years, GetYourGuide received only 5 bookings. Today the platform is worth $2BN. They have raised from some of the best, including an amazing story with Masa Son and Softbank.
In Today’s Episode We Discuss:
01:45 – “I Regret Our Series A — Too Much Dilution”
03:50 – US vs Europe: Why European Founders Are Tougher
06:10 – “Germany Spends €100B on Pensions, €7B on VC – It’s Insane”
08:40 – Why Europe Fails to Build $10B Startups
10:25 – 90% of Our Team in Berlin Aren’t German. Here’s Why.
12:20 – Recruiting Netflix’s Head of Growth Nearly Killed Me
16:20 – “We Had 5 Bookings in 2 Years. 3 Were My Mum.”
18:00 – “I Asked My Parents to Remortgage Their House for a Pivot”
21:15 – The Vatican Tour That Changed Everything
23:30 – Why VCs Rejected GetYourGuide 100+ Times
28:30 – The $14M Series A That Nearly Killed the Company
31:00 – “I Hired All the Wrong People – Then Laid Off 30%”
36:30 – The $450M SoftBank Deal... Then COVID Hit
40:00 – “We Went to $0 in Revenue in 3 Weeks”
42:10 – The Sequoia Tree Mindset: Grow Through Fire
49:30 – What SoftBank’s Masa Son Was Really Like in Person
52:00 – How He Thinks About Secondary, Wealth, and Not Losing His Soul
55:30 – “My Worst Hires Came from Listening to VCs Too Much”
58:30 – Angel Investing in Trade Republic and TravelPerk: My Lessons
01:01:00 – Do You Have to Work 7 Days a Week to Win?