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)
Timestamps are as accurate as they can be but may be slightly off. We encourage you to listen to the full context.
Podcast Summary
In this compelling episode, Harry Stebbings, founder of 20VC, shares his remarkable journey from a struggling 19-year-old to raising $70 million on WhatsApp and interviewing 107 billionaires. The conversation covers his incredible story of making £1.75 million in 36 hours to help pay for his mother's MS medication, his persistence in cold emailing Marc Benioff 53 times, and his unconventional fundraising approach that leveraged personal relationships through WhatsApp messaging. (03:00)
- Main themes include entrepreneurial persistence, relationship building, content creation as a business strategy, and seven key lessons learned from billionaires that can transform how ambitious professionals approach success and wealth building
Speakers
Harry Stebbings
Harry Stebbings is the founder of 20VC, one of the world's leading venture capital podcasts, and manages a $400 million fund. He dropped out of university at 19 to pursue entrepreneurship and has since interviewed 107 billionaires, raised $70 million through WhatsApp messages, and built a media empire that generates millions in revenue from a single LinkedIn post.
Simon Squibb
Simon Squibb is a successful entrepreneur and content creator based in the UK. He founded multiple businesses including Fluid agency and has built a significant social media following through his "What's Your Dream" content series where he interviews people on the street about their entrepreneurial aspirations.
Key Takeaways
Never Accept "No" as a Final Answer
When fundraising for his venture capital fund, Harry was turned down by potential investors but refused to accept their rejection. He sent follow-up emails explaining how he had previously missed $500 million investment opportunities due to market skepticism, suggesting the investors might be making the same mistake. (19:40) This persistence resulted in securing $12 million from two investors who had initially declined. The lesson: rejection is often just the starting point for negotiation, and most people give up too early when persistence could unlock significant opportunities.
Leverage Social Proof and Personalization in Cold Outreach
Harry's success in getting high-profile guests like Marc Benioff (after 53 cold emails) demonstrates the power of combining social proof with personal details. (20:21) Each email included personalized elements like "PS, I hope you're enjoying the McAllen 75, it's also my favorite" and leveraged previous successful interviews as social validation. This approach transforms cold outreach from spam into compelling, relationship-building communication that busy executives actually want to respond to.
Focus on Building Your First Million Aggressively
Harry emphasizes that "the hardest to make is your first million by far" and explains how the financial system inherently favors those who already have wealth through better interest rates, investment products, and exclusive opportunities. (11:26) The first million acts as a key that unlocks exponentially more opportunities, making it crucial to prioritize this milestone above other goals when starting out in business or investing.
Distribution Beats Product Innovation
Rather than focusing solely on revolutionary new ideas, Harry advocates for taking existing concepts and improving them by 10-20% while building superior distribution channels. His venture fund's success comes not from having a completely new investment model, but from adding media distribution that competitors lack. (17:56) A single LinkedIn post generated $4 million in revenue for one of his portfolio companies, demonstrating how distribution can create more value than product innovation alone.
Use Role Models as Decision-Making Frameworks
When faced with difficult decisions, Harry uses Pat Grady from Sequoia Capital as his decision-making compass, asking "What would Pat do?" because he admires Pat as a great father, investor, and husband. (25:46) This framework helps ensure decisions align with long-term values rather than short-term impulses, providing clarity in complex situations where multiple valid options exist.
Statistics & Facts
- Harry made £1.75 million in 24 hours at age 19 by cold emailing 25 CEOs and pricing sponsorships at $95,000 each, just under the $100,000 procurement budget threshold, with 19 of them accepting. (05:05)
- It took Harry 4 years to reach 1,000 podcast plays, demonstrating that success in content creation requires extreme long-term persistence, with most people giving up before seeing results. (16:11)
- A single LinkedIn post from Harry generated $4 million in revenue for his portfolio company Fixer, illustrating the concrete financial value that distribution and audience can bring to investments. (17:56)
