Long Strange Trip: CEO to CEO with Brian Halligan

Scaling AI Rocketships: ElevenLabs’ Mati Staniszewski & Lovable’s Anton Osika

Long Strange Trip: CEO to CEO with Brian Halligan

Show Notes

This one’s a treat: two AI-native CEOs building some of the world’s fastest-growing startups from outside of Silicon Valley.

Mati and Anton are navigating a world that’s moving 10X faster than it was when I was CEO of HubSpot. We dig into the realities of what it’s like scaling today: managing co-founder relationships when you're the only person you can complain to, delegating while staying in founder mode, building exec teams that blend experience with homegrown talent, and why lightweight planning rhythms are key when the AI tech stack changes every six months.

Both share tactical advice on managing chaos, from email triage systems to no-meeting days. They open up on Europe's advantages (hungry talent, less competition) and disadvantages (thinner executive bench), the 9-9-6 work culture debate, and why the next generation of European founders could finally build trillion-dollar companies. I thought these guys shared an honest look at what it really takes to lead through hypergrowth these days.

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