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)

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)

Author: Harry Stebbings January 24, 2026 Duration: 42:54
The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch
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AGENDA:

00:03:00 – Harry's Wild Start: Making £1.75M at 19 in 36 Hours

00:06:00 – How Harry Got Marc Benioff on 20VC with Cold Emailing Alone

00:07:30 – Raising $70M on WhatsApp – Relationship Building Secrets

00:12:00 – Decision Framework: What Would Pat Grady (Sequoia) Do?

00:15:00 – Chase Your First Million – It Unlocks Everything

00:16:30 – Advice for 19-Year-Olds Today: Niche Down, Interview Leaders, Publish

00:18:00 – University Is a Waste for Most | Leverage Youth & Risk

00:22:30 – How Getting Kicked Out of School Changed Everything

00:30:00 – Why Should Everyone Be Creating Content Today and How to Start

00:35:30 – 7 Lessons from Billionaires

  • 00:36:00 – #1: Never Accept No (The $12M Turnaround Story)

  • 00:37:30 – #2: Beat Down the Door (53 Emails to Marc Benioff)

  • 00:39:00 – #3: Just Start – 99% Never Do

  • 00:40:30 – #4: Use a Role Model Framework for Hard Decisions

  • 00:42:00 – #5: Chasing Money Won't Make You Happy – Enjoy the Art

  • 00:44:00 – #6: Break Big Visions into Achievable Milestones

  • 00:45:30 – #7: Win Over the Partner (Power of Pillow Talk)

 


Hosted by Harry Stebbings, The Twenty Minute VC (20VC) pulls back the curtain on the high-stakes worlds of venture capital and startup building. Each episode is a compact, twenty-minute dive into the minds shaping the future of technology. You’ll hear candid conversations with legendary investors, the very individuals who fund and guide the next generation of companies, featuring voices like Sequoia's Doug Leone and Benchmark's Bill Gurley. Beyond the capital, this podcast dedicates time to the founders themselves. Weekly, Stebbings sits down with transformative entrepreneurs such as Spotify's Daniel Ek, LinkedIn's Reid Hoffman, and Snowflake's Frank Slootman, unpacking the real journeys behind their iconic companies. The format is direct and focused, cutting straight to the core insights on funding strategies, pitch dynamics, and the personal philosophies that drive success. Tuning into this podcast means gaining an unfiltered perspective from both sides of the table, all delivered in a concise and accessible style that fits into your day.
Author: Language: English Episodes: 100

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