BILLIONS Inside the playbook behind the podcast turned into a $400,000,000 venture fund - Harry Stebbings
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Jan 5, 2026 
Harry Stebbings, a venture capitalist and founder of The Twenty Minute VC, turned his podcast into a $400 million fund by leveraging storytelling. He discusses the secrets of turning content into capital and the importance of founder quality over market trends. Harry shares his biggest investment regrets and insights on why many VCs shy away from content creation. With successes like Linktree, he highlights how media can accelerate portfolio growth and outlines strategies for effective outreach and fundraising. His bullish perspective on European startups adds a fresh twist!
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The $400M Miss: Passing on Deel
- Harry missed investing in Deel at seed because he let market incumbents and sector bias influence him.
- He calls that a "$400 million mistake" and says he carries the scar as a daily lesson.
Bet On Founders, Not Markets
- Invest in founders first, market second: great founders will find or create the right market over time.
- Back generational founders even if the current market seems crowded or incumbents exist.
Disclose Weaknesses And Prove Progress
- When fundraising, state your weaknesses and show concrete mitigation and trending metrics to build LP trust.
- Use recent deal data and clear ownership targets to prove progress toward stated goals.