Long Strange Trip hosted by Brian Halligan

11 Nov 2025 · 1 min

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In short

Brian Halligan (HubSpot co-founder/longtime CEO) introduces “Long Strange Trip,” focusing on how startup founders evolve into scale-up CEOs as leadership playbooks are “torn up” and rethought across industries.

Guest backgrounds

Anton (Lovable) is an early-stage founder; Parker (Muppling) leads a scale-up; David Solomon (Goldman Sachs) represents a large-company executive.

Key claims

leadership approaches used by CEOs are being fundamentally reconsidered, with examples spanning Elon Musk’s empire, Jensen (noted as a major tech leader), and Brian Chesky’s “founder mode.”

Notable examples

Elon Musk’s operating style, Jensen’s leadership, and Brian Chesky’s approach are referenced as contrasts to traditional CEO playbooks.

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Transcript

Automatic transcript. May contain errors.

0:00Hey, I'm Brian Halligan, co-founder of HubSpot and its longtime CEO. The CEO playbook I grew up with seems like it's getting torn up. Everyone from Elon and how he runs his empire to Jensen in his 60 Direct Reports to Brian Chesky in his founder mode.

0:17Brian Halligan:Everything is sort of being rethought from scratch. I'm fascinated with this. I'm fascinated with thinking about how do I help startup founders turn into scale up CEOs. So I started this podcast. Hopefully you'll like it. I interview a lot of my friends who are going through that journey from early stage founders like Anton from Lovable to scale ups like Parker from Muppling to big companies like David Solomon from Goldman Sachs. Hope you enjoy it. I'll see you on the other side.

From the publisher

Brian Halligan–Sequoia partner and co-founder and longtime CEO of HubSpot—is on a quest to uncover the new rules of CEO-ing from the best CEOs in the world, from hypergrowth AI-native startups like Lovable and ElevenLabs to scaleup juggernauts like Robinhood and Rippling, to 150-year-old behemoths like Goldman Sachs.Watch at: 

https://www.youtube.com/sequoiacapital

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