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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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Crusoe CEO Chase Lochmiller: Turning Stranded Energy Into Intelligence
Chase Lochmiller runs one of the most operationally complex companies in AI: Crusoe builds power plants, manufactures electrical equipment, operates gigawatt-scale data centers, and runs a managed AI cloud on top, all under one roof. He jus
Luca Ferrari: The Operating System Behind Bending Spoons
Luca Ferrari is co-founder and CEO of Bending Spoons, a serial acquirer of AOL, Vimeo and Evernote, Airtable, etc, that buys to hold forever, and whose only real edge is that it operates software companies better than almost anyone else. Be
Databricks’ Ali Ghodsi Never Wanted to Be CEO. Now He’s Among the Best
Ali Ghodsi never wanted the CEO job. In 2015, Databricks had a wildly successful open source project, $1.5 million in revenue, and a board quietly interviewing other candidates behind his back. He got the seat as a trial run. They didn't ev
The Philosopher CEO | Clay Co-Founder Kareem Amin
I had Kareem Amin all wrong. When Clay first crossed my radar, I thought he was too laid-back: no chip on his shoulder, not the hungry founder I expected to win. Clay has since exploded. Kareem builds from what he calls "a place of wholenes
Kalshi’s Tarek Mansour vs. the Federal Government
Tarek Mansour calls himself a paranoid risk manager - the guy who can list 20 ways a hot air balloon will go down before it leaves the ground. Then he bet his entire company on suing its own regulator. Kalshi spent years walking through the
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 to face. He joins me to share what all of them actually have in common, and it isn'
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's circular org chart or Brian Armstrong's player-coach approach. He thinks hierarc
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 founders Jack Dorsey and Ev Williams, Dick spent five years dragging Twitter from a
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 – to testify before Congress alongside the presidents of Harvard and UPenn. You know
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 (https://sequoiacap.com/article/from-hierarchy-to-intelligence/): the traditional corporate hierarchy i
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 company behind the most talked-about wearable on the market - the Oura ring. In this
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 take the company private and then becoming CEO with an unwavering commitment to pri
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 unpack founder mode, where it works and where people are taking it too far. Ben shares
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 flattened 11 layers of management, expanded managers' direct reports from 6 to 90, a
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 raise $3 billion in a few hours during the GameStop frenzy to navigating a 90% stoc
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 from zero to $190M run rate in just a few years. What stands out? His obsessive intens
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 Networks, he openly admits he didn’t know what cybersecurity even meant. Today, under hi
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 job as “choosing between two shitty options.” David discusses some of the tough call
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 a world that’s moving 10X faster than it was when I was CEO of HubSpot. We dig into t
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 led its evolution from boxed software to an AI-driven platform. I’ve always admired I
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 let his rage propel him into an all-consuming mission to prove the haters wrong and
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, from hypergrowth AI-native startups like Lovable and ElevenLabs to scaleup juggerna
