20VC: Ashton Kutcher on Early Lessons From Investing in Airbnb and Spotify, Why VC Ownership Requirements Are Becoming More and More Egregious & What Being Good At Product Truly Means
The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch
Release Date: 02/17/2020
20VC: From $6.2BN Market Cap to $2.8BN: What Is Not Translating About Navan's Public Story | Are Any Public Company CEOs Actually Happy? | Why Navan Built It's Own Customer Service AI and What it Could Mean For Customer Service AI with Ariel Cohen
The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch
Ariel Cohen is the Co-Founder and CEO of Navan (formerly TripActions), an AI-powered travel and expense platform. Last month, Ariel took the company public, since being a public company, they have faced a torrid time seeing stock price decline by 50%. The company is currently valued between $4BN-$5BN. AGENDA: 0:00 The Truth About Going Public After 11 Years 5:50 Why We Couldn't Wait: The Real Reason for the IPO 8:15 Disrupting the Giants: Amex, Concur, and the $1T Opportunity 11:50 "If We Don't Build This, We're Dead": Seeing ChatGPT Early 18:35 Why Navan Built Their Own Customer Service...
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20VC: SpaceX Completes Acquisition of xAI | The 2026 SaaS Massacre: Public Market Collapse | Microsoft’s $360 Billion Market Cap Loss | NVIDIA's $100BN Investment Dispute with OpenAI | Waymo Raises $16 Billion at a $110 Billion Valuation
The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch
AGENDA: 00:00 - SpaceX Completes Acquisition of xAI in $1.25 Trillion Merger 08:44 - The Rehabilitation of the IPO and the End of "State Private Forever" 15:53 - The 2026 SaaS Massacre: Public Market Collapse 31:20 - Next-Gen CRM War: Hubspot Down 50%+ vs Next Gen Heavily Funded 45:30 - Microsoft’s $360 Billion Market Cap Loss and the Shift in AI Narrative 52:45 - Nvidia’s Strategic Retreat: The Dispute Over the $100 Billion OpenAI Investment 01:03:30 - Waymo Raises $16 Billion at a $110 Billion Valuation 01:17:30 - The Launch of OpenClaw and Moltbook: 1.5 Million Agents Join a...
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20VC: 50% of Funds Will Go Out of Business | Why Growth Expectations Today are BS and Will Not Last | Why Oren Zeev Takes $0 Management Fees But 30% Carry | Why GPs Should Not Tell LPs Their Strategy
The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch
Oren Zeev is one of the most prominent solo capitalists in venture. He is one of the most no BS investors of our time. Oren manages over $1BN in AUM and is known for his "radical alignment" approach, often taking $0 in management fees. His track record includes massive successes like Navan, Audible, and Houzz. AGENDA: 03:11 – Why the Best Investments Always Look "Wrong" at the Start 05:58 – The AI Tsunami: How to Spot Beneficiaries vs. Victims 10:43 – The Death of Incumbents? Why Most AI Predictions Are Wrong 14:12 – Why Chasing Hyper-Growth is a "Disaster Waiting to Happen" 19:41 –...
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20Growth: How Wix Built a $100M Marketing Machine | Why LTV is BS and Why Time Return On Investment is the Most Important Metric | How to 10x Your Growth: What is the Next Great Channel with Omer Shai, CMO @ Wix
The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch
Omer Shai serves as the CMO at Wix. Shai leads a team of over 400 people and is responsible for the company’s global online and offline marketing activity, which boasts an incredible growth of approximately 3 million new users every month. Under Shai, the marketing department has executed hundreds of worldwide campaigns for television and social including 5 Super Bowl commercials, creative videos, podcasts and more. AGENDA: 00:00 — The AI Agent Revolution: 93% Automation? 03:55 — Why I’m Buying TWO Super Bowl Ads This Year 08:58 — The $100M Marketing Secret: Brand vs. Performance...
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20VC: Brex Acquired for $5.15BN | a16z Companies are 2/3 AI Revenues | Anthropic Inference Costs Skyrocket | OpenEvidence Raises at $12BN Valuation | The IPO Market: EquipmentShare, Wealthfront and Ethos Insurance
The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch
AGENDA: 03:36 Brex Acquisition by Capital One for $5.15BN 10:54 Does Brex’s Acquisition Help or Hurt Ramp? 16:28 TikTok Deal Completed: Who Won & Who Lost: Analysis 19:30 Anthropic Inference Costs Higher Than Expected 37:50 Open Evidence Raises at $12BN from Thrive and DST 53:56 Wealthront IPO Disaster: Is $1.5BN IPO Too Small? 01:07:27 Salesforce Wins $5BN Army Contract: The Last Laugh for SaaS
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20VC: From Only OpenAI to Die-Hard Anthropic: The Downfall of OpenAI in Enterprise | Harvey vs Legora: Legal AI is a Winner Take All | $7M ARR in a Single Day and Raising $200M Across 3 Rounds with No Deck with Max Junestrand, CEO @ Legora
The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch
Max Junestrand is the Co-Founder and CEO @ Legora, the legal AI company that has scaled to 750 of the world’s leading law firms as customers and over 300 employees in just 2 years. They have raised over $200M from some of the best in the business including Benchmark, General Catalyst, Redpoint and ICONIQ. AGENDA: 04:16 Why Does Everyone Think Harvey When They Hear Legal AI? 07:35 Why OpenAI is Toast? Switching to Anthropic! 11:47 24 Months: Which Foundation Models Will Win? 23:53 Lessons Scaling from Europe into the US 28:53 Do Americans Work As Hard As They Say? 32:20 Why Seat...
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20VC: Raising $400M for 20VC: Fundraising Lessons | Getting Marc Benioff Through 53 Cold Emails: How to Master Cold Outbound | 7 Lessons from 101 Decacorn Founders with Harry Stebbings (Simon Squibb Edition)
The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch
AGENDA: 00:03:00 – Harry's Wild Start: Making £1.75M at 19 in 36 Hours 00:06:00 – How Harry Got Marc Benioff on 20VC with Cold Emailing Alone 00:07:30 – Raising $70M on WhatsApp – Relationship Building Secrets 00:12:00 – Decision Framework: What Would Pat Grady (Sequoia) Do? 00:15:00 – Chase Your First Million – It Unlocks Everything 00:16:30 – Advice for 19-Year-Olds Today: Niche Down, Interview Leaders, Publish 00:18:00 – University Is a Waste for Most | Leverage Youth & Risk 00:22:30 – How Getting Kicked Out of School Changed Everything 00:30:00 – Why Should...
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20VC: Sam Altman vs Elon Musk: The $100BN Battle | The Implosion of Thinking Machines | Can VC Survive Public Market Pricing Today? | ClickHouse and Replit's New Rounds: Analysed
The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch
AGENDA: 03:30 Can VC Survive With Public Market Prices Today 15:20 The Implosion of Thinking Machines 21:13 Elon Musk vs. OpenAI: The Legal Battle 40:50 Can OpenAI Win Ads? 55:50 ClickHouse’s $15BN Deal: Analysed 58:55 Replit’s $9BN Deal: Analysed 01:08:35 There Are Only Two Types of Deals VCs Want To Do Today
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20VC: How Model Performance is Plateauing | Two Key Rules for Effective Deal-Making | Company Building Lessons from Keith Rabois, Brian Halligan and Pat Grady | Why Enterprise AI Adoption is Years Off with Harvey CEO Winston Weinberg
The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch
Winston Weinberg is the CEO and Co-Founder of Harvey, the leading professional services platform engineered with AI for law, tax, and finance. Winston has raised over $980M for Harvey from Sequoia, a16z, GV, Elad Gil and more with a last round price of $9.2BN post-money. Before founding Harvey in August 2022, Winston was an attorney at O'Melveny & Myers LLP, specializing in antitrust and securities litigation. AGENDA: 04:10 #1 Thing Every Founder Needs to Do Everyday 05:33 Must Do Daily Routines and Productivity Tips for CEOs 12:45 How to Get Sequoia and a16z Term Sheets 15:06 Why...
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20Product: Is the Design Phase Dead in a World of AI | Has Claude Code Crushed Anthropic Already | What Roles of a PM Are Less and More Important with AI | How the Best Product Leaders Tell Stories with Noam Lovinsky, CPO @ Superhuman
The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch
Noam Lovinsky is the CPO @ Superhuman (formerly Grammarly). Prior to Superhuman he was a Senior Director of Product Management at Facebook. In his earlier years, he was CPO @ Thumbtack and spent 5 years as a Director of Product Management at Google where he was responsible for all of Youtube’s applications. AGENDA: 03:43 What is Great Product Leadership in a World of AI 07:45 Does the Design Phase Die in a World of Vibe Coding 12:21 How AI Changes Product Development Most 22:23 Accelerating Product Development 29:32 AI's Impact on Product Building 34:19 Predictions for 2026 34:45 Quick...
info_outlineAshton Kutcher is a Founder & General Partner @ Sound Ventures. Over the last 5 years, Ashton and his partner, Guy Oseary, have built Sound into one of the West Coast's leading new entrants with a portfolio including Lambda School, Calm, Gitlab, Affirm, Bird and many more incredible companies. As for Ashton, he started his investing career as an angel with early home runs including Spotify, Alibaba, Skype, Airbnb and Optimizely. Due to his immense success both in media and technology, Ashton has been named one of TIME magazine’s “100 Most Influential People in the World”.
In Today’s Episode You Will Learn:
1.) How Ashton made his way into the world of startups with his foray into angel investing in Skype, Spotify etc? How did that lead to his founding Sound Ventures most recently?
2.) How does Ashton's background in the world of media impact Sound's investment strategy and the type of deals they get excited by? Question from Daniel Ek @ Spotify: How did your deal sourcing look lin the early days? How has that changed over time and with the institutionalisation of Sound?
3.) Why does Ashton believe people creating the future are perpetually young? What question does Ashton always like to ask founders? What does he look for in their answer? How does Ashton ensure founders feel comfortable with him? What does he do to allow them to open up? What is the hardest thing Ashton feels he has persevered through?
4.) How does Ashton build strong product intuition about products in areas he is not familiar with? In terms of great product, Ashton backed Spotify with Daniel Ek and Shak Khan, what did Ashton see in Spotify way back then? How did Shak and Daniel innovate on distribution and customer acquisition with him and Spotify?
5.) What have been Ashton's learnings in what it takes to truly win the best and most competitive deals? Before as an angel, Ashton's check size was friendly, now with Sound it is competitive with VCs, how does Ashton approach the element of now competing with many VCs he once co-operated with? What does Ashton make of the rise of many celebrity investors today?
Items Mentioned In Today’s Show:
Ashton’s Fave Book: The Undoing Project: A Friendship that Changed the World, Scale: The Universal Laws of Life and Death in Organisms, Cities and Companies
Ashton’s Most Recent Investment: Community
As always you can follow Harry, The Twenty Minute VC and Ashton on Twitter here!
Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.