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.