Deep Questions to Reveal Character

In this episode, Wouter Teunissen sits down with Harry Stebbings, founder of 20VC, to explore how he turned a teenage side project into one of venture capital’s most influential media empires. At just 18, Harry launched The Twenty Minute VC from his childhood bedroom. Within a few years, it became the go-to show for the world’s top investors and founders—from Sequoia to Stripe.

That momentum became the foundation for 20VC Fund, which has now raised more than $800 million to back early-stage startups. Harry’s story is one of relentless curiosity and consistency. He shares what he’s learned from interviewing thousands of founders, how he built trust with Silicon Valley’s elite before ever setting foot there, and why he believes the key to success isn’t speed—it’s stamina. Today, 20VC isn’t just a podcast. It’s a bridge between storytelling and capital allocation—an inside look at how the best founders think, decide, and build.

This episode is presented by Rho , the all-in-one banking platform for startups. Thousands of startups like Perplexity, Product Hunt, and more use Rho. You get everything you need to manage your startup’s cash. Exclusively for Biography Pod listeners and viewers, you’ll get a $1500 statement credit plus a ton of exclusive perks when you manage your company cash with Rho. To learn more, visit https://rho.co/biography

Follow Harry: https://x.com/HarryStebbings

20VC: http://20vc.fund/

Follow Wouter: https://x.com/WouterTeunissen

Biography Newsletter: https://biography.beehiiv.com/

Timestamps: 00:00:00 Intro

00:00:57 - Falling in love with technology as a teenager

00:03:15 - The greatest founders have these two qualities

00:06:34 - Self belief is everything

00:08:41 - How to make sure you have a mediocre team

00:10:05 - How do you raise $800 Million for your fund?

00:14:05 - Fuck Vision. Be Micro-Ambitious

00:14:52 - You can manufacture luck

00:18:47 - Cold Emailing Marc Benioff from Salesforce

00:21:00 - The best founders make you ....

00:26:03 - In VC today, this is why a billion dollars is not enough

00:30:33 - Wiring $5 Million in less than 24 hours

00:34:15 - VC is becoming commoditised

00:40:24 - Focus on your winners

00:42:25 - What is your North Star Metric?

00:45:19 - Project Europe and Why Paul Graham is wrong

00:52:54 - I don't want to fucking brainstorm.

00:55:55 - The 3 things great founders do

00:59:04 - I look for deep trauma when hiring

01:00:51 - Be a Purple Cow.

01:05:41 - Why I didn't invest in Vanta or Deel at pre-seed (Mistake)

01:10:51 - How an investment led to the hospital.

01:13:50 - Everything in life comes from how you respond to hardship.

01:19:14 - Everyone is going through a battle you know nothing about

01:20:20 - You're never wrong to do the right thing.

01:22:01 - We spend too much time on culture.