Harry Stebbings & Jason Lemkin: AI's Real B2B Impact

Why This Crossover Conversation Matters for SaaS Leaders

This session starts at 2:53:59 in the SaaStr AI London recording.

This is the live crossover episode: Harry Stebbings (20VC, the most popular venture podcast) joins Jason Lemkin on stage for an extended conversation. The format allows for deeper exploration than typical conference talks.

The OpenAI discussion is timely - they note that "the OpenAI story today is almost the exact opposite" of yesterday's story. It's "code red focus on the core" - a reminder of how fast things move at the frontier. What seems like stable strategy can shift overnight.

The conversation covers a range of B2B companies: Snowflake's new CEO appearance at SaaStr Annual, Eventbrite's challenges (Jason jokes "he's going to be extra pissed with me"), and broader market dynamics. These aren't abstract discussions - they're specific takes on specific companies from two people who talk to founders and investors daily.

The live format creates moments of candor you don't get in polished keynotes. When you put two people with strong opinions in front of an audience for over an hour, you get real perspective rather than talking points.

4 Insights From Stebbings and Lemkin on B2B AI

• OpenAI's strategy shifts rapidly - yesterday's narrative can be "almost the exact opposite" of today's
• Live conversations between industry figures reveal more candid takes than prepared talks
• The B2B landscape is in flux - even established players like Snowflake and Eventbrite face questions
• Having strong opinions on specific companies (not just trends) is what makes commentary valuable