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) artwork

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)

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

January 24, 2026

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?
Speakers: Harry Stebbings, Simon Squibb
**Harry Stebbings** (0:00)
This is 20VC with me, Harry Stebbings. Now, I'm very often asked to reveal a little bit about my story, and I'm always quite reserved in doing so. I think you have to really return a lot of money to investors before you think you're worthy of being interviewed. And I think too many young VCs are too out there when they haven't made a lot of money for investors. And then I get a lot of people say, we want to hear more about you, we want to hear your story. And so I did a show with Simon Squibb, a brilliant entrepreneur in the UK. My mother said that she loved the show and that she thought that it should be heard by our community and our fans. And so today we released a very special one where Simon interviews me. You hear a little bit behind the scenes of 20VC, the fundraising strategy for a $400 million fund, how I got Marc Benioff to come on 20VC through 53 cold emails and many, many more cool stories. But before we dive into the show today, this episode is brought to you by Perk, the intelligent platform for travel and spend, every successful founder remembers their breakthroughs, those moments in the journey that changed their trajectory, whether it was going from burning cash to building leverage or from headcount growth to operational scale. Breakthroughs don't come from spending hours buried in spreadsheets, booking and rebooking travel or chasing their teams for last quarter's coffee receipts. That's shadow work and that's what Perk was built for. One recent study found shadow work cost companies over $1.7 trillion every year as employees waste hour after hour on manual, time-consuming work instead of the jobs they were hired to do. Perk's AI is purpose-built to automate shadow work so teams can focus on real work with real impact. Don't let anything get in the way of your next breakthrough. Leave the travel and spend to Perk. Visit perk.com/20vctoday.
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That's dailybodycoach.com/twozerovc, and take the next step. While Daily Body Coach helps you build healthier habits, Air Wallis helps you get paid globally without the headache. Founders, let's get real about the growth tax. You've raised VC funding and you're scaling globally, and it's no longer about shipping product. It's about orchestrating operations across continents. But suddenly, your payments and finance stack is choking your growth. You're logging into lots of different banking portals, waiting days for transfers and wasting hundreds of hours on manual reconciliation and reporting across entities. It's operational drag and it's at your scale. It's costing millions. That's why I'm so excited to partner with Air Wallis. Air Wallis are more than just a banking alternative to HSBC or Citi. Air Wallis brings you an intelligent financial operating system that powers how global businesses operate and grow, allowing you to manage and automate banking, treasury, payments and spend. The most exciting part for me, they're heavily investing in agentic finance. If you're scaling globally, you need a banking and finance platform that's borderless, real-time and intelligent. Check out Air Wallis today and see how they're helping thousands of businesses like Canva, McLaren and Deal. Scale at airwallis.com/20vc. Terms and conditions apply. Your moneys are safeguarded, not FSCS protected. See airwallis.com for more details.

**Simon Squibb** (4:24)
You have now arrived at your destination. Harry, thanks for being here. Off camera, we were just talking about like you're 19 years old, you made in a million and a half pounds. Can you talk a little bit about that quickly before we get into all the lessons you're going to teach us today?

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