24 Jan 2026
42m

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)

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The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch

Harry Stebbings is interviewed by Simon Squibb, delving into Stebbings' journey as a young venture capitalist and podcaster. Stebbings shares how he raised $1.75 million in 24 hours at age 19 by leveraging FOMO and personalization in cold emails to tech CEOs to help his mother. He emphasizes the importance of persistence, detailing how he emailed Marc Benioff 53 times to secure an interview. Other topics include building relationships through platforms like WhatsApp, the value of starting even when not fully prepared, and the significance of distribution in today's market. Stebbings also outlines seven lessons learned from billionaires, including never accepting "no" and focusing on achievable goals.

Outlines

Part 1: Introduction, Background

Part 2: Sales, Psychology, Networking

Part 3: Mindset, Drive, Early Career

Part 4: Media, Content, Personal Brand

Part 5: Lessons on Persistence

Part 6: Taking Action, Risk

Part 7: Success, Happiness, Mentorship

Part 8: Work Ethic, Innovation

Part 9: Vision, Influence, Conclusion

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