Inside the playbook behind the podcast turned into a $400,000,000 venture fund - Harry Stebbings

Today on BILLIONS, I’m sitting down with Harry Stebbings — the guy who turned a microphone in his bedroom into a $400 million venture fund.

He started The Twenty Minute VC as a teenager, and it became the place where the smartest founders of unicorns, and the world’s best investors all lined up to talk.

In this episode, Harry opens up about the deals he missed, the unicorns he caught early like Linktree and Tripledot, and how he turned content into capital.

If you’ve ever wondered how storytelling can build an empire, this is the playbook.

TIMELINE :

00:00:00 - 00:03:36 : Turning content into deal flow: The 20VC playbook
00:03:36 - 00:06:26 : From obsession to insight: How Harry predicted the future of VC
00:06:26 - 00:09:03 : Why most VCs suck at content—and how to stand out
00:09:03 - 00:12:48 : $400M facepalms: Inside Harry’s biggest investment regrets
00:12:48 - 00:17:35 : What separates great founders from everyone else
00:17:35 - 00:27:50 : Building the fund: Raising $8M from a podcast mic to $400M
00:27:50 - 00:36:22 : The underrated VC weapon: High-impact content as revenue driver
00:36:22 - 00:44:52 : Going public vs staying private: Who really wins?
00:44:52 - 00:58:52 : Charisma, crisis, and credibility: The raw truth about founder DNA
00:58:52 - 01:04:23 : Bullish on Europe: Beating Silicon Valley at its own game

REFERENCES :

- Peter Thiel

- Michael Moritz

- Alex Bouaziz (Deel)

- Christina Cacioppo (Vanta)

- Peter Fenton

- Daniel Ek

- Nick Storonsky 

- Marc Benioff

- Guy Kawasaki

- Steve Ballmer

- Thibault Elziere 

- Torsten Reil

- Mati Staniszewski

- 20VC

- Project Europe

- a16z