Big Deal Misses and Lessons Learned

He started a podcast in his bedroom before most people land their first job.

Now, Harry Stebbings runs one of the most influential platforms in venture capital and manages a $400M fund.

In this episode of The Burnouts, Harry sits down with Phoebe Gates and Sophia Kianni to unpack what actually drives success — and why so many smart, ambitious people stay stuck. From dropping out of law school to building leverage through content, Harry shares the lessons he learned the hard way about confidence, decision-making, and playing the long game.

This conversation goes far beyond startups and investing. Harry opens up about the confidence gap holding people back, why men bluff and women wait, and how likeability, storytelling, and persistence often matter more than raw intelligence. He explains how content became one of the most powerful tools in his career, why distribution now shapes opportunity, and how relationships — not resumes — drive the biggest decisions.

Harry also reflects on regret, missed deals, mentorship, and the uncomfortable truth that success often comes from taking action before you feel ready. Whether you’re early in your career, thinking about building something of your own, or just feeling behind, this episode offers a rare, honest look at what actually works.

Chapters
00:00 – The Reality of Entrepreneurship
00:40 – From The Social Network to Dropping Out of Law School
01:55 – Building a Fund Through Media & Network Effects
02:31 – Why Venture Capital Over Being a Founder
03:38 – Co-Founders, Breakups & Hard Personal Lessons
07:18 – What Actually Makes a Great Founder
08:55 – Gender, Confidence & Entrepreneurship
14:23 – Mentorship vs Coaching & How to Get Access
16:40 – Content as a Distribution Weapon
23:29 – Finding Your First True Fans
25:18 – Building & Managing High-Performance Teams
29:22 – Investment Mistakes & Missed Billion-Dollar Deals
31:35 – Vulnerability, Trust & People Skills
36:05 – WhatsApp, Fundraising & Relationship Scaling
37:30 – Trust, Endurance & Outworking Everyone
40:00 – Storytelling, Creativity & the Risk of AI
44:16 – Being a Great Investor When Things Go Wrong
45:02 – Final Advice: Take the First Step

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About The Burnouts
The Burnouts brings you raw, unfiltered conversations with today’s top founders, creators, athletes, and culture-shaping entrepreneurs. Hosted by Stanford roommates turned startup co-founders Phoebe Gates and Sophia Kianni, the show goes beyond the headlines to reveal the real stories behind ambitious careers.

Past guests include Paris Hilton, Chelsea Handler, Kris Jenner, Karlie Kloss, and more.

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