Harry Stebbings

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)

Harry Stebbings

Founder & General Partner

20VC

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.

Maggie Hott

GTM Team Member

OpenAIWebflow

Harry Stebbings

Founder & General Partner

20VC

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/HarryStebbingsLinkedIn: 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 time at https://Lemon.io/twist(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(30:49) CLA. Get started with CLA's CPAs, consultants, and wealth advisors now at https://www.claconnect.com/tech Great TWIST interviews: Will Guidara, Eoghan McCabe, Steve Huffman, Brian Chesky, Bob Moesta, Aaron Levie, Sophia Amoruso, Reid Hoffman, Frank Slootman, Billy McFarland Check out Jason’s suite of newsletters: https://substack.com/@calacanis Follow TWiST: Twitter: https://twitter.com/TWiStartups YouTube: https://www.youtube.com/thisweekin Instagram: https://www.instagram.com/thisweekinstartups TikTok: https://www.tiktok.com/@thisweekinstartups Substack: https://twistartups.substack.com Subscribe to the Founder University Podcast: https://www.youtube.com/@founderuniversity1916

Harry Stebbings

Founder & General Partner

20VC

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

Founder & General Partner

20VC

Jason recently joined Harry Stebbings on 20VC to discuss VC in 2023. Hear why you shouldn't wait to raise (if you're fundable), even though the venture landscape will look better by the end of 2023. This episode is an excerpt of Jason and Harry's discussion. You can watch the full video here: https://youtu.be/dHIWdwljt7Q Want to join the SaaStr community? We're the 🌎largest community for B2B software. Subscribe for weekly updates: https://www.saastr.com/subscribeform Twitter: https://twitter.com/saastr LinkedIn: https://www.linkedin.com/company/2724976 Quora Group: https://www.quora.com/q/cloud Facebook: https://www.facebook.com/SaaStr/ Instagram: https://www.instagram.com/saastr/ Our North American Event: https://bit.ly/2OXeAYh Our European Event: https://bit.ly/2OZTad8

Harry Stebbings

Founder & General Partner

20VC

We're celebrating episode 500 of the SaaStr Podcast! Our SaaStr 'OG' podcaster, Harry Stebbings, Founder of The 20 Minute VC and, Jason Lemkin, SaaStr CEO and Founder discuss the future of the markets and how to build a successful SaaS sales team from the ground up. Blog post & video: https://www.saastr.com/how-to-scale-saas-sales-team-with-harry-stebbings-jason-lemkin/ Sponsors: https://shortcut.com/saastr https://www.litmus.com/saastr https://flatfile.com/saastr/

Harry Stebbings

Founder & General Partner

20VC