Long Strange Trip: CEO to CEO with Brian Halligan

Sequoia Capital 17 episodes

The CEO rulebook is getting rewritten. Brian Halligan, Sequoia partner and co-founder and longtime CEO of HubSpot, sits down with some of the CEOs who are defining the new one—from hypergrowth AI-native startups to 150-year-old behemoths. Whether you’re an early-stage founder or a scale-up CEO, Brian will be digging for advice you can use on the long strange trip of your own CEO journey.

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Jun 4, 2026 56m

David Senra: Mute the World and Build Your Own

David Senra has spent a decade reading the biographies of 400+ founders for his podcast Founders - and lately he's started interviewing the living ones face ...

May 21, 2026 1h 3m

Notion’s Ivan Zhao: The Refounder

Ivan Zhao, founder and CEO of Notion, joins me to introduce a new contender in the founder mode debate: jazz mode. Ivan has a different take than Jack Dorsey...

May 7, 2026 1h 8m

Surviving Twitter's Growing Pains: Ex-CEO Dick Costolo

Dick Costolo took over as CEO of Twitter in 2010, inheriting what he calls "the drama queen of hypergrowth companies." Hired as the adult in the room behind ...

Apr 16, 2026 44m

What Founders Can Learn About Excellence From MIT President Sally Kornbluth

Sally Kornbluth is president of MIT and one of the best crisis leaders I've come across. Within a year of starting the job, she got summoned – not invited – ...

Apr 2, 2026 1h 3m

Jack Dorsey: Every Company Can Now Be a Mini-AGI

Jack Dorsey (Block CEO) and Roelof Botha (Sequoia partner and Block board member) join to discuss a bold claim they wrote about recently: the traditional cor...

Mar 26, 2026 59m

Oura’s Tom Hale: What People Don’t Tell You About Being CEO

Tom Hale didn't originally set out to be a CEO - then he put it on his bucket list to prove something to himself. Now he runs Oura, the Finnish health tech c...

Mar 12, 2026 1h 2m

The Most Founder Mode CEO Working Today Isn’t the Founder: Opendoor’s Kaz Nejatian

Kaz Nejatian reveals how he left Shopify to pull off a highly unusual feat: refounding a struggling public company in just 16 days. From first attempting to ...

Feb 26, 2026 49m

Ben Horowitz On What Makes a Great Founder

A16z’s Ben Horowitz joins me for a raw, unfiltered conversation on what actually breaks founder CEOs, and what separates the great ones from the rest. We un...

Feb 12, 2026 1h 12m

Bayer’s Bill Anderson: Turning a 168 Year-Old Tanker Like a Speedboat

Bill Anderson runs Bayer, a 160-year-old pharmaceutical giant that had 100,000+ employees when Bill took the helm. In just two years after becoming CEO, he f...

Jan 29, 2026 43m

The Wartime CEO: Vlad Tenev of Robinhood

In this episode, Vlad Tenev pulls back the curtain on what it takes to lead through the kind of crises that would break most CEOs. From waking up at 5 AM to ...

Jan 15, 2026 56m

Harvey CEO Winston Weinberg: Why You Should Reinvent Yourself Every 4 Months

This might be my favorite episode yet. Harvey’s Winston Weinberg is the canonical 2026 hypergrowth CEO. He takes us inside what it's really like to scale f...

Jan 8, 2026 1h 4m

Palo Alto Networks’ Nikesh Arora: Why Context Switching is a CEO’s Most Critical Superpower

Nikesh Arora is one of the most fascinating CEOs in tech. He didn’t come up through cybersecurity. He wasn’t a founder. And when he took over Palo Alto Netw...

Dec 18, 2025 57m

Goldman Sachs CEO David Solomon: What Startup Founders Get Wrong About the CEO Job

David Solomon, CEO of Goldman Sachs, says that no easy decisions reach the CEO’s desk - only “51/49” decisions. When I was leading HubSpot, I described the j...

Dec 11, 2025 57m

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

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 ...

Nov 20, 2025 49m

Intuit CEO Sasan Goodarzi’s Grown-Up CEO Playbook

When Intuit was born, the world ran on DOS. Forty years later it is a $180 billion powerhouse serving millions of small businesses, and Sasan Goodarzi has le...

Nov 13, 2025 1h 16m

Parker Conrad’s Revenge Fantasy

I didn’t think Parker Conrad would get up off the mat when he got ousted from his previous startup, Zenefits. No one in Silicon Valley did. Instead, Parker l...

Nov 11, 2025 0m

Long Strange Trip hosted by Brian Halligan

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, ...

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