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
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 10:02 – Why Robinhood Built a Secret ChatGPT for Support 12:11 – The One Customer Type That Transformed the Business 15:29 – “CoreWeave Is Retail’s Way Into AI” — The Meme Stock Defense 18:05 – Inside Robinhood’s Tokenized Private Shares Product 21:23 – “Capital as a Service” — Vlad’s Wild Vision for Startup Fundraising 24:10 – The $100M Revenue Line Vlad Wishes He Could Kill 26:45 – Robinhood Is Building... Cash Delivery Trucks?! 29:55 – “We Were Shipping Nothing”: Vlad on the 2020–2022 Culture Crisis 33:20 – What Line of Business Will Be the Biggest For Vlad in 5 Years Time 35:11 – The One Competitor Vlad Actually Respects 36:55 – From Men’s Health to Japanese Toilets: Vlad’s Weirdest Quickfire Yet 38:40 – “I Was in the Dumps”: What 2022 Taught Vlad About Resilience 40:00 – Where Robinhood Is Headed: The Next Decade of Financial Infrastructure
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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
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 Tripled Conversions 13:21 – From Software Budget to Labor Budget: The Shift is Happening 16:35 – The Big Lie: Why Autonomous Agents Still Suck 19:24 – The Secret Sauce Behind HubSpot’s Email AI Stack 21:44 – Segment-Based Marketing Is Dead. Enter Micro Audiences. 24:15 – Content Collapse: Why Google Organic Is Getting Torched 30:52 – The Future of AI SEO: 1 Product, 100 Pages, Infinite Prompts 33:16 – Memory = Moat: Why ChatGPT Is Becoming Unbeatable 35:46 – Prompt Engineering is the New Coding: Here's How to Win 41:03 – The Death of the Middle Manager Marketer 46:17 – OpenAI vs. Anthropic: Kieran’s $400M Bet 48:00 – Europe Is Falling Behind: The Harsh Truth on Regulation 52:39 – CMO Playbook 2025: Micro-Audiences, Creator-Led, AI at Scale
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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
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 Loophole You’re Missing [48:00] Microsoft’s AI Layoffs: Salespeople Are Dead, Long Live Engineers [50:00] “If You Need a Week to Learn AI, You Should Be Fired” [53:00] Will Sequoia’s Sean Maguire Be Pushed Out? Place Your Bets [57:00] Will There Be a Recession in 2025? Jason Bets $75K It’s a No [1:00:00] Is Linda Yaccarino Still CEO of X by Year-End? [1:03:00] Circle and CoreWeave’s Meme Rally: Real or Mirage?
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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
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 We Break Up Big Tech? 08:00 – Why Young People Have a Right to Be Angry? 11:00 – Why the Tax Code Is Rigged Against the Young 13:00 – Tax Changes That Would Make Young People Rich Again 17:00 – The Tinder Effect: Why Men Are Angry 20:00 – The Loneliness Epidemic in Men 23:00 – Remote Work & The Case for Alcohol 26:00 – Why Richer Families are Happier Families 30:00 – The Truth About Kids and Career 34:00 – Are Billionaires Happy? 38:00 – Becoming a Better Son, Father, Partner 46:00 – Behind the Persona: Who Scott Galloway Really Is
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20VC: Figma's IPO: The Full Breakdown | Index Returns $3.5BN on Two Deals | Why Melio's $2.5BN Acquisition is "Discouraging" | Asana's New CEO and the Great Founder Exodus | Oracle's $30BN AI Deal and What it Means for Incumbents
AGENDA: 00:00 – $400B in AI CapEx: Rational Investment or Madness? 05:00 – Figma's IPO: Rule of 80, $1.5B in cash, 40% margins. Unreal. 08:00 – Adobe Screwed the Deal—Should They Have Just Bought Canva? 16:00 – Pay-to-Play Deals: Heroic Hail Mary or Guaranteed Write-Off? 21:30 – How Index Is Returning $3.5B on 2 Deals 24:00 – Melio’s $2.5B Exit: Insane Growth… So Why Did They Sell?! 35:00 – Massive Penthouses and the Death of Focus: AI Founders Beware 39:00 – Chime, Anthropic, Menlo & The Art of Selling LPs the Future 41:00 – Couchbase Acquired: PE Buyers Are Back… Or Are They? 44:00 – Why No One’s Buying These 9-Figure SaaS Zombies 48:00 – If You Didn’t Grow from AI By June 30, You’re Already Dead 53:00 – Superhuman vs The AI-Natives: Who Wins the Replatforming War? 54:30 – Oracle's $30B AI Deal: Larry Did It Before You Even Started 56:00 – Scale Is Dead. Long Live Surge. The AI Data War Gets Bloody. 01:01:00 – Asana CEO Move & the Great Founder Exodus of 2025 01:06:00 – Will Cluely’s Founder Be a Billionaire by 2029? Place Your Bets
About The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch
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 Snowflake's Frank Slootman.
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