Harry Stebbings

Harry Stebbings has transformed a bedroom podcast into a media and investment conglomerate, leveraging that platform to back ten unicorns. In conversation with Bobby Molavi, head of EMEA execution services and European primary distribution for Equity Capital Markets in Equities, Stebbings discusses his journey from an 18-year-old dropout to a leading venture capitalist, exploring how distribution and brand have become the ultimate weapons in a commoditized capital market. He shares his "science of content," the shifting loyalty in early-stage investing, and why he believes Europe is currently the greatest opportunity in the venture landscape. This session was recorded on March 4, 2026 at the 2026 Goldman Sachs Disruptive Technology Symposium in London. The opinions and views expressed herein are as of the date of publication, subject to change without notice, and may not necessarily reflect the institutional views of Goldman Sachs or its affiliates. The material provided is intended for informational purposes only, and does not constitute investment advice, a recommendation from any Goldman Sachs entity to take any particular action, or an offer or solicitation to purchase or sell any securities or financial products. This material may contain forward-looking statements. Past performance is not indicative of future results. Neither Goldman Sachs nor any of its affiliates make any representations or warranties, express or implied, as to the accuracy or completeness of the statements or information contained herein and disclaim any liability whatsoever for reliance on such information for any purpose. Each name of a third-party organization mentioned is the property of the company to which it relates, is used here strictly for informational and identification purposes only and is not used to imply any ownership or license rights between any such company and Goldman Sachs. A transcript is provided for convenience and may differ from the original video or audio content. Goldman Sachs is not responsible for any errors in the transcript. This material should not be copied, distributed, published, or reproduced in whole or in part or disclosed by any recipient to any other person without the express written consent of Goldman Sachs. Disclosures applicable to research with respect to issuers, if any, mentioned herein are available through your Goldman Sachs representative or at http://www.gs.com/research/hedge.html Goldman Sachs does not endorse any candidate or any political party. © 2026 Goldman Sachs. All rights reserved. Learn more about your ad choices. Visit megaphone.fm/adchoices

AGENDA: 00:03:00 – Harry's Wild Start: Making £1.75M at 19 in 36 Hours 00:06:00 – How Harry Got Marc Benioff on 20VC with Cold Emailing Alone 00:07:30 – Raising $70M on WhatsApp – Relationship Building Secrets 00:12:00 – Decision Framework: What Would Pat Grady (Sequoia) Do? 00:15:00 – Chase Your First Million – It Unlocks Everything 00:16:30 – Advice for 19-Year-Olds Today: Niche Down, Interview Leaders, Publish 00:18:00 – University Is a Waste for Most | Leverage Youth & Risk 00:22:30 – How Getting Kicked Out of School Changed Everything 00:30:00 – Why Should Everyone Be Creating Content Today and How to Start 00:35:30 – 7 Lessons from Billionaires 00:36:00 – #1: Never Accept No (The $12M Turnaround Story) 00:37:30 – #2: Beat Down the Door (53 Emails to Marc Benioff) 00:39:00 – #3: Just Start – 99% Never Do 00:40:30 – #4: Use a Role Model Framework for Hard Decisions 00:42:00 – #5: Chasing Money Won't Make You Happy – Enjoy the Art 00:44:00 – #6: Break Big Visions into Achievable Milestones 00:45:30 – #7: Win Over the Partner (Power of Pillow Talk)

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 🔗 FOLLOW US Phoebe Gates Sophia Kianni Harry Stebbings 20VC 🔥 FOLLOW THE BURNOUTS Instagram TikTok LinkedIn 📲 Support What We’re Building Phoebe 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 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. Subscribe for the insider playbook to build your dream career.

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

SaaStr 834: Why OpenAI Doesn't Pay Sales Commission (And Why It Works) with OpenAI GTM Leader Maggie Hott, and Harry Stebbings, Founder of 20VC Discover how OpenAI's unique approach to B2B sales compensation is changing the game. In this interview with Harry Stebbings, Founder of 20VC, Maggie Hott, OpenAI GTM leadership, shares her experience at OpenAI, including why they don't pay sales commissions, and what B2B sales leaders can learn from this disruptive model. --------------------- This episode is Sponsored in part by HappyFox: Imagine having AI agents for every support task — one that triages tickets, another that catches duplicates, one that spots churn risks. That'd be pretty amazing, right? HappyFox just made it real with Autopilot. These pre-built AI agents deploy in about 60 seconds and run for as low as 2 cents per successful action. All of it sits inside the HappyFox omnichannel, AI-first support stack — Chatbot, Copilot, and Autopilot working as one. Check them out at happyfox.com/saastr --------------------- Hey everybody, the biggest B2B + AI event of the year will be back - SaaStr AI in the SF Bay Area , aka the SaaStr Annual, will be back in May 2026. With 68% VP-level and above, 36% CEOs and founders and a growing 25% AI-first professional, this is the very best of the best S-tier attendees and decision makers that come to SaaStr each year. But here's the reality, folks: the longer you wait, the higher ticket prices can get. Early bird tickets are available now, but once they're gone, you'll pay hundreds more so don't wait. Lock in your spot today by going to podcast.saastrannual.com to get my exclusive discount SaaStr AI SF 2026. We'll see you there.

This Panel took place at LSI Europe ‘25 Emerging Medtech Summit in London. Join venture capitalist Harry Stebbings of 20VC Fund as he hosts a signature conversation with Henry Peck from LSI, exploring insights on investment strategies and market trends in the life sciences industry. This Panel featured: Henry Peck — LSI Harry Stebbings — 20VC Fund Join us at our next event: https://www.lifesciencemarketresearch.com/why-lsi-summits Follow us on social: LinkedIn: https://www.linkedin.com/company/life-science-intelligence/ Twitter: https://twitter.com/lsintelligence Instagram: https://www.instagram.com/lifescienceintelligence/ Facebook: https://www.facebook.com/LifeScienceIntelligence/ Spotify: https://open.spotify.com/show/7LnmGOwBMmRHJeDXmv3KEI?si=a93200169a884c09 Subscribe to our YouTube: https://www.youtube.com/channel/UCxAwCTpHCMTScEJbgW7Scjw

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.

“You really have to be unwaveringly obsessed..." Harry Stebbings’ career began at the age of 13, when he watched The Social Network — David Fincher and Aaron Sorkin’s brooding portrayal of the earliest days of Facebook. But whereas many of us watched that film and thought: “I’d quite like to be a tech founder”, Harry watched it and thought: “Gosh. I want to be a venture capitalist.” A few years later, and with £200 pounds in the bank and not a single contact in the VC world, Harry started his podcast, The Twenty Minute VC. Now, more than 10 years and 1400 episodes later, Harry has pivoted his juggernaut-like podcast into his very own VC fund — one that has backed 13 unicorns to-date. Here, in a beautifully candid interview, Harry tells the podcast about the AI start-up sphere; why he chooses to work nine-to-nine, six days a week; how his often lonely childhood formed his entrepreneurial mindset; the dangers of social media usage; and the things that make him optimistic about the future.

Agency to €2.5M Platform: The Anti-Prompting Revolution That Caught 20VC's Attention Thibaut de la Grand'rive, CEO of Delos, reveals how they evolved from an AI consulting agency into a €2.5M-funded orchestration platform backed by Harry Stebbings' 20VC—without building a single AI model. Inside This Episode: • Why 90% of enterprise employees can't prompt AI (and how Delos eliminates prompting entirely) • The strategic agency-first approach that validated their product while getting paid for R&D • How orchestrating Claude, GPT, and Mistral creates more value than building your own LLM • Why Allianz and Shiseido chose Delos over 250+ vertical AI competitors The "Post-RAG" technology that goes beyond traditional AI implementations • How they're retaining elite French engineers (Polytechnique, ENS) against 9x salary competition Perfect For: • Startup founders exploring agency-to-product strategies • AI entrepreneurs avoiding the "build your own model" trap • Enterprise leaders struggling with AI adoption and prompting challenges • CTOs seeking orchestration solutions over single-model dependencies • European tech founders planning US market expansion Key Insights: • Why most enterprise AI fails at the UX layer, not the technology layer • How Delos creates "cockpit" experiences where users "just click buttons" • The funding strategy that attracted Team Aventures (Xavier Niel) and Plug and Play • Why avoiding vertical AI plays (meeting notes, etc.) builds sustainable moats • How French engineering culture creates competitive advantages in AI talent retention Episode Timeline: 00:00 - Introduction to Thibaut and Delos platform overview 00:59 - Founding story: Starting 2 days after GPT-3.5 release 03:27 - David's distributed team problem and platform demo request 05:34 - Live demo: Newsletter creation and AI orchestration workflow 11:37 - Using custom prompts and agent templates in Delos 12:52 - Website localization and international expansion plans 13:28 - From agency to product: The strategic validation journey 16:18 - Investor relationships and fundraising philosophy 19:12 - Meeting Harry Stebbings and the 20VC investment story 20:22 - War for AI talent: Competing with OpenAI's Paris office 23:36 - Future fundraising plans and capital allocation strategy 27:51 - Competitive threats: Will OpenAI copy their approach? 31:15 - US expansion strategy and investor considerations 33:55 - Pricing strategy and roadmap for agentic AI features Where to find me: • David: Linkedin • Email: hello@thehomebase.ai Want to stay ahead of AI's impact on jobs and future opportunities? Join 18000+ tech leaders and founders who are shaping the future of AI here: • Newsletter: Join Here </p

This Week in Startups is brought to you by… Lemon.io - Get 15% off your first 4 weeks of developer time at https://Lemon.io/twist Squarespace - Use offer code TWIST to save 10% off your first purchase of a website or domain at https://www.Squarespace.com/TWIST CLA. Get started with CLA's CPAs, consultants, and wealth advisors now at https://claconnect.com/tech Today’s show: Jason and Alex break down the biggest tech stories of the moment. OpenAI is pushing to rewrite copyright laws to benefit AI companies while suing others for doing the same—hypocrisy or smart strategy? Meanwhile, European startups are fleeing to the U.S. as overregulation and weak IPO markets make scaling harder. Harry Stebbings joins to discuss whether Project Europe can reverse the trend. Plus, with AI-driven startups staying lean, angel investing is evolving—should investors wait for traction or bet on potential? Jason shares his 2024 playbook. Watch the full episode now! Timestamps: (0:00) Episode Teaser(1:15) OpenAI's recommendations, stance on copyright, and ethics(8:30) Sam Altman's political donations and the media's response (9:41) Lemon.io - Get 15% off your first 4 weeks of developer time at https://Lemon.io/twist (15:48) Introduction of guest Harry Stebbings and his venture capital journey(19:51) Squarespace - Use offer code TWIST to save 10% off your first purchase of a website or domain at https://www.Squarespace.com/TWIST (22:05) Discussing the human aspect of investing and handling criticism(27:37) Project Europe and its support for EU founders(30:49) CLA. Get started with CLA's CPAs, consultants, and wealth advisors now at https://www.claconnect.com/tech (32:16) Balancing roles as an investor and public figure(33:04) Analyzing the European startup ecosystem(35:48) Addressing Project Europe's age cap and mentorship(38:09) Global talent competition and Europe's stance(42:29) Economic impacts and the future of Project Europe(45:18) Growth and housing in Austin compared to other tech regions(47:36) Startup funding strategies and angel investment advice(55:27) Evolving startup and content creation landscapes(57:37) Founder University announcement Subscribe to the TWiST500 newsletter: https://ticker.thisweekinstartups.com Check out the TWIST500: https://www.twist500.com Subscribe to This Week in Startups on Apple: https://rb.gy/v19fcp Links from the show: Check out Project Europe: https://www.projecteurope.co/ Check out 20VC: https://www.thetwentyminutevc.com/ Check out Stride VC: https://stride.vc/ Follow Harry: X: https://x.com/HarryStebbings LinkedIn: https://www.linkedin.com/in/harrystebbings Follow Alex: X: https://x.com/alex LinkedIn: ⁠https://www.linkedin.com/in/alexwilhelm Follow Jason: X: https://twitter.com/Jason LinkedIn: https://www.linkedin.com/in/jasoncalacanis Thank you to our partners: (9:41) Lemon.io - Get 15% off your first 4 weeks of developer

SaaStr 718: Predictions for Venture, IPOs, and the State of SaaS in 2024 with SaaStr CEO and Founder Jason Lemkin and Harry Stebbings, Founder and Host of the 20 Minute VC Harry Stebbings, Host of the 20VC, recently hosted SaaStr CEO and Founder, Jason Lemkin for one of the first podcasts of the year. Together, they talk about the best of SaaS from 2023, the state of SaaS in 2024, and their predictions for Venture and IPOs for the year ahead. -------------------------------------------------------------------------------------------- SaaStr hosts the largest SaaS community events on the planet. Join us in 2024 at: SaaStr Annual: Sept. 10-12 in the SF Bay Area. Join 12,500 SaaS professionals, CEOs, revenue leaders and investors for the world's LARGEST SaaS community event of the year. Podcast listeners can grab a discount on tickets here: https://www.saastrannual2024.com/buy-tickets?promo=fave20 SaaStr Europa: June 5-6 in London. We'll be hosting the 5th SaaStr Europa in London for two days of content and networking. Join 3,000 SaaS and Cloud leaders. Podcast listeners can grab a discount on Europa tickets here: https://www.saastreuropa2024.com/buy-tickets?promo=fave200 -------------- This episode is sponsored by: Northwest Registered Agent When starting your business, it's important to use a service that will actually help you. Northwest Registered Agent is that service. They'll form your company fast, give you the documents you need to open a business bank account, and even provide you with mail scanning and a business address to keep your personal privacy intact. Visit https://www.northwestregisteredagent.com/saastr to get a 60 percent discount on your next LLC.

Harry Stebbings is the Founder of 20VC, building the next great financial institution at the intersection of media and venture capital. 20VC has reached over 125M downloads in 100+ countries and has featured the likes of Doug Leone, Bill Gurley, Marc Benioff, Daniel Ek and more. On the investing side, Harry has raised over $400M and made investments in the likes of Pachama, Linear, TripleDot , Superhuman, AgentSync, Linktree, Sorare and more. In Today's Episode We Cover: Are LPs Open for Business: How has what LPs look for in new manager investments changed? What type of funds will be able to raise? Which will not be able to raise? What can managers do to significantly increase their chances of raising a new fund? 2. The Seed Investing Landscape: Harder Than Ever Why is seed pricing as high as ever ? Why are multi-stage funds more active in seed than ever? How does this impact seed? How will seed change and evolve over the next 6-12 months? 3. Series A + B: The Best Place to be Investing Why is Series A the best risk/reward insertion point when investing today? How has the competition level at Series A and B changed? What do many people not see or know about this stage of the market today? 4. Is Growth Dead: Are Growth Deals Getting Done: What two core elements are needed if you want to raise a growth round today? How have growth round valuations been impacted over the last 12 months? To what extent do founders need to change their expectations on the price of rounds they will be able to get done today? 5. M&A and IPOs: Tough Times Ahead Why will we see continued low levels of activity in M&A markets? What acquisitions are we seeing take place? When will the IPO window crack open? Why were Klaviyo, Instacart and Arm not enough to open the windows?