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He Raised $800M Starting at 18 to Invest In Startups (Harry Stebbings, 20VC)

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Nov 13, 2025

Guest

Harry Stebbings

Harry Stebbings, founder of 20VC and a venture capital pioneer, shares his incredible journey from launching a podcast at just 18 to raising over $800 million for early-stage startups. He discusses his passion for technology and the importance of hiring with long-term relationships in mind. Harry emphasizes the significance of founder quality over market size and reveals how interviewing skills enhance investor trust. With personal stories of overcoming hardship, he highlights empathy and perseverance as keys to success in venture capital.

01:30:06

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Episode notes

insights

INSIGHT

Founder Quality Trumps Early Metrics

The only thing that truly matters at seed is founder quality; market and traction matter far less early.
To return a big fund you need extreme outsize exits, so bet on obsessive, relentless founders.

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ADVICE

Make Founders Open Up By Changing Context

Make founders comfortable to open up by walking, showing vulnerability, or asking for advice.
Use interviewing skills to get honest signals fast and build stronger founder relationships.

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ANECDOTE

Project Europe: Finding Hidden Young Talent

Project Europe started after Harry saw too few European founders in elite programs and wanted to change that.
The program found and funded teenage founders across Europe, including early acquisitions and strong outcomes.

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Becoming Obsessed with Tech and Venture

00:21 • 3min

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Turning Early Curiosity into Action

03:02 • 13sec

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How Personal Struggles Shaped Drive

03:15 • 3min

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Preparation, Inferiority Complex, and Leadership Style

06:30 • 2min

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Hiring Deliberately and Avoiding Team Churn

08:52 • 1min

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Fundraising as Relationship Building

10:16 • 2min

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Rapid Fund Growth and Tactical Outreach

12:08 • 35sec

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The Simple Job of Venture: Maximize Returns

12:44 • 1min

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Rejecting Vision in Favor of Micro-Ambition

14:05 • 3min

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Cold Emailing Techniques That Work

16:40 • 5min

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Making Your Own Luck Through Activity

Founder Quality Over Market at Seed

26:00 • 2min

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How Interviewing Improves Investing

28:18 • 2min

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Customer Experience for Founders

30:46 • 2min

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Speed, Network, and High-Quality Decisions

33:12 • 57sec

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Why Media Strengthens Venture Edge

34:10 • 2min

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Editing for Attention and Product Quality

36:19 • 3min

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Handling Unreleased Interviews and Reputation

39:36 • 55sec

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Passing on Investments with Kindness

40:30 • 2min

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Relentless Focus on Winning

42:26 • 2min

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Using a North Star to Make Decisions

44:48 • 32sec

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Project Europe: Building European Founder Infrastructure

45:20 • 3min

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Why Europe Can Produce Global Winners

48:12 • 3min

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Project Europe as Legacy Work

51:06 • 4min

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Traits of Founders Who Reach $100M ARR Fast

55:10 • 4min

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Hiring: Look for Hardship and Grit

59:00 • 1min

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Being the Purple Cow in Competitive Term Sheets

01:00:28 • 4min

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Rapid Decisions, In-Person Meetings, and Cultural Signals

01:04:20 • 6min

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Authenticity and Directness with Founders

01:10:00 • 52sec

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Intense Operating Cadence and Discipline

01:10:52 • 2min

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Sobriety, Family Motivation, and Purpose

01:12:28 • 3min

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How Early Hardship Fuels Ambition

01:15:28 • 3min

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Turning Adversity into Opportunity

01:18:11 • 1min

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Be Kind: Everyone Fights Hidden Battles

01:19:32 • 42sec

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Reputation, Doing the Right Thing, and Decision Filters

01:20:14 • 1min

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Leadership as Conducting Diverse Talents

01:21:36 • 51sec

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Winning Drives Culture and Development

01:22:27 • 54sec

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First Big Win: Sponsorship Validation

01:23:21 • 44sec

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The Marathon and Tokyo Tests to Reveal Fit

01:24:05 • 2min

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Deep Questions to Reveal Character

01:25:50 • 3min

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Nuance Over Absolutes and Final Advice

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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