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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)

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

The Twenty Minute VC

Business, Investing, Tech News, News

4.4 β€’ 693 Ratings

πŸ—“οΈ 24 January 2026

⏱️ 43 minutes

🧾️ Download transcript

Summary

AGENDA:

00:03:00 – Harry's Wild Start: Making Β£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)

Β 

Transcript

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0:00.0

This is 20 VC with me, Harry Stebings. Now, I'm very often asked to reveal a little bit about my story, and I'm always quite reserved in doing so.

0:07.9

I think you have to really return a lot of money to investors before you think you're worthy of being interviewed.

0:13.6

And I think too many young VCs are too out there when they haven't made a lot of money for investors.

0:19.0

And then I get a lot of people say,

0:21.2

we want to hear more about you, we want to hear your story. And so I did a show with Simon Squib,

0:25.8

a brilliant entrepreneur in the UK. My mother said that she loved the show and that she thought

0:30.9

that it should be heard by our community and our fans. And so today we release a very special one

0:36.6

where Simon interviews me.

0:38.3

You hear a little bit behind the scenes of 20VC, the fundraising strategy for a 400 million

0:43.1

fund, how I got Mark Benny off to come on 20VC through 53 cold emails and many, many more

0:49.4

cool stories. But before we dive into the show today, this episode is brought to you by Perk, the intelligent

0:55.2

platform for travel and spend. Every successful founder remembers their breakthroughs, those

1:00.1

moments in the journey that changed their trajectory, whether it was going from burning cash to

1:04.6

building leverage or from headcount growth to operational scale. Breakthroughs don't come from

1:09.7

spending hours buried in spreadsheets,

1:11.8

booking and rebooking travel or chasing their teams for last quarter's coffee receipts. That's

1:16.4

shadow work and that's what Perk was built for. One recent study found shadow work cost

1:21.4

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.

1:31.6

Perk's AI is purpose-built to automate shadow work so teams can focus on real work with real impact.

1:38.6

Don't let anything get in the way of your next breakthrough.

1:41.5

Leave the travel and spend to Perk.

1:43.6

Visit perk.com forward slash

...

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