Harry Stebbings

About Harry Stebbings

Harry Stebbings is the founder and general partner of 20VC, one of the most influential venture capital media platforms in the world. He started The Twenty Minute VC podcast from his bedroom at age 18 with a 50-pound microphone and cold outreach, building it into a media empire that has conducted hundreds of interviews with the biggest names in technology and venture capital.

What began as a podcast evolved into a full investment operation. The 20VC Fund has grown to over $800 million in assets under management, with 13 or more unicorn investments. Stebbings has become one of the most connected figures in the global startup ecosystem, interviewing CEOs, founders, and investors at the intersection of technology, business, and AI.

Based between London and San Francisco, Stebbings brings an unusually broad view of the venture landscape. His interview style — direct, self-deprecating (“that’s great Jerry, but what about me?”), and focused on practical implications — has made 20VC required listening for founders and investors navigating the AI transition.

Career Highlights

• Founded The Twenty Minute VC podcast at age 18
• Built 20VC Fund to $800M+ AUM with 13+ unicorn investments
• Interviewed hundreds of top VCs, founders, and tech leaders
• Regular speaker at SaaStr and major tech conferences
• One of the youngest prominent venture capitalists globally

Notable Positions

On the VC Landscape in the AI Era

Stebbings consistently probes whether traditional venture capital frameworks — triple-triple-double-double growth expectations, seat-based SaaS metrics, PE-style buyouts — survive the AI transition. His interviews reveal a generation of investors grappling with the possibility that everything they learned in the past decade may be irrelevant.

On Enterprise SaaS Disruption

Through interviews with leaders like Sebastian Siemiatkowski (Klarna), Jerry Murdock (Insight), and Jason Lemkin (SaaStr), Stebbings has built one of the most comprehensive records of how AI is reshaping enterprise software economics.

Key Quotes

• “Is everything that we’ve been taught for the last 5 to 10 years completely irrelevant?” (on the AI disruption of venture investing)
• “Will enterprise software just be entirely vibe-coded, personalized, customized?” (on the future of SaaS)

Related Reading

• SaaS-to-AI Transformation - A recurring theme across 20VC interviews
• Knowledge Work Disruption - Explored in multiple episodes
• AI Agents - Central topic in 20VC’s AI coverage