The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch 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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Jan 24, 2026 
Simon Squibb, entrepreneur and podcast host known for founder interviews, sits down with Harry Stebbings. They cover wild early wins, relentless cold outreach that landed Marc Benioff, and raising big rounds via personal relationships. Short, punchy stories on persistence, content as distribution, turning failure into opportunity, and seven billionaire lessons packed into practical takeaways.
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Rapid Sponsorship Win
- Harry emailed 25 top tech CEOs offering sponsorship slots and got 19 yes answers at $95k each.
- He raised £1.75M in ~24 hours to help pay for his mother's MS medication by creating urgency and personalization.
Personalize Every Outreach
- Use personalization and small human touches to triple your response rate when cold outreaching.
- Mention specific preferences or a PS line to build rapport and stand out from generic pitches.
Fundraise On WhatsApp
- Harry raised $70M by courting wealthy individuals and moving conversations off email to WhatsApp.
- He built decade-long relationships first and used informal messaging to close commitments quickly.
