$400M Investor Explains the Confidence Gap Holding You Back (ft. 20VC Harry Stebbings)

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.Chapters00:00 – The Reality of Entrepreneurship00:40 – From The Social Network to Dropping Out of Law School01:55 – Building a Fund Through Media & Network Effects02:31 – Why Venture Capital Over Being a Founder03:38 – Co-Founders, Breakups & Hard Personal Lessons07:18 – What Actually Makes a Great Founder08:55 – Gender, Confidence & Entrepreneurship14:23 – Mentorship vs Coaching & How to Get Access16:40 – Content as a Distribution Weapon23:29 – Finding Your First True Fans25:18 – Building & Managing High-Performance Teams29:22 – Investment Mistakes & Missed Billion-Dollar Deals31:35 – Vulnerability, Trust & People Skills36:05 – WhatsApp, Fundraising & Relationship Scaling37:30 – Trust, Endurance & Outworking Everyone40:00 – Storytelling, Creativity & the Risk of AI44:16 – Being a Great Investor When Things Go Wrong45:02 – Final Advice: Take the First Step 🔗 FOLLOW USPhoebe GatesSophia KianniHarry Stebbings20VC🔥 FOLLOW THE BURNOUTSInstagramTikTokLinkedIn📲 Support What We’re BuildingPhoebe and Sophia aren’t just your hosts—they’re the founders of Phia, a fashion-tech app helping shoppers find the best prices across retail and resale. Download the app and help us grow.About The BurnoutsThe 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.Subscribe for the insider playbook to build your dream career. Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.