The Burnouts with Phoebe & Sophia $400M Investor Explains the Confidence Gap Holding You Back (ft. 20VC Harry Stebbings)
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Jan 8, 2026 
Harry Stebbings, founder of 20VC and a venture investor managing over $400M, shares his journey from law school dropout to influential podcaster. He discusses the confidence gap that holds many back, emphasizing how storytelling and relationships trump raw intelligence. Harry reveals the importance of content in building opportunities and the power of visualization in boosting confidence. He also reflects on mentorship, the traits of great founders, and the need for action over perfection, making this conversation a treasure trove for aspiring entrepreneurs.
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Bedroom Podcast Turned Fundraising Engine
- Harry started 20VC by interviewing top founders from his bedroom in 2015 and used those relationships to raise his first fund.
- His first fund grew to about $8M after guests committed checks like $250k following podcast exposure.
Regret Over A Hasty Partnership Exit
- Harry described breaking with his co‑founder Fred and regretted how he left that relationship too quickly.
- He says the way you exit a business or personal tie determines how you're remembered and regrets not leaving more gracefully.
Three Traits Common To Top Founders
- The top founders often share three traits: parental relationship breakdown, gaming skills, and frequent childhood moves.
- Entrepreneurship is glorified but most people are not masochistic enough to enjoy being "punched in the face" repeatedly.
