He built Thrillist. He bet on media. Now Ben Lerer is navigating a world obsessed with AI.

In this episode, Jason sits down with Ben Lerer, co-founder of Thrillist, creator of Group Nine Media, and now Managing Partner at Lerer Hippeau. They talk about the shifting tides of media, tech, and early-stage investing. From building one of the first great digital brands to navigating the rise of creators, platforms, and AI, Ben shares hard-earned insights on what it takes to survive—and thrive—through disruption.

Key Takeaways:
✅ Media brands chased scale, but the platforms took the audience (and the money)
✅ In today’s startup world, no AI in the pitch means something’s off
✅ Cost-cutting kills companies; real growth comes from bold bets
✅ Great founders—not trends—should guide where you invest

Memorable Moments:
💡 “The winners weren’t the publishers—it was the pipes.”
💡 “We almost named it Ape Alert. That would’ve been a disaster.”
💡 “If I need a calendar reminder to make a decision, it’s a no.”
💡 “We believe founders are smarter than us. If we’re around great talent, we’ll end up in interesting markets.”

Brought to you by Mekanism.