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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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't what Silicon Valley thinks. His one word is focus — what he calls "mute the world and build your own." He walks through Dana White buying the UFC for $2 million and turning it into a nearly $8 billion TV deal by ignoring everything outside his own arena; why...
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 hierarchy is human nature, and that you can't flatten it away but you can build a company that improvises like a jazz band instead of marching in formation. Notion has roughly 60 ex-founders on staff and a deliberately decentralized structure to make that work. We ge...
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 chaotic collective into a public company, and learned a scale-up CEO playbook in the process. We get into how he killed group decision-making and replaced it with what he calls "bias to yes"—only your direct manager can tell you no. Why he stopped solving pro...
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 how that went. The others didn’t make it. Sally did, and she came out stronger. We spend a lot of time on sustaining meritocracy, which I think is one of the hardest things for any scaling CEO to pull off. Sally has a line I can't shake: if you take a lick of ...
Jack Dorsey, Block CEO, and Roelof Botha, Sequoia partner, delve into Block's revolutionary shift from a corporate hierarchy to an "intelligence layer" model, with AI at its core. This transformation, including a 40% workforce reduction, aims to optimize information flow, empower employees with AI agents, and establish a customer-driven roadmap. They also share insights on evolving CEO roles, building effective boards, and the importance of continuous learning and conviction in an era of rapid technological change.
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 conversation, we get into what the job actually feels like from the inside (spoiler: the kibble-to-champagne ratio is not what you think), and Tom shares some of the sharpest frameworks I've heard for scaling a company through the 200-to-2,000 employee gauntl...
OpenDoor CEO Kaz Nejatian shares his unique "founder mode" approach, emphasizing stewardship, deliberately overriding life's defaults, and taking responsibility for outcomes. He details his unexpected journey to refounding OpenDoor in just 16 days, Shopify's strategic pivots, and his vision for an AI-native company. Nejatian also delves into personal beliefs, including the role of faith, family alignment in career, and the deep value of marriage and children in leadership.
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 why overly deferring to experienced executives creates politics and fiefdoms, but avoiding senior talent altogether is just as risky. Founder mode is not about micromanaging. It’s really about taking responsibility for outcomes and having the confidence to ma...
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, and eliminated annual budgeting in favor of 90-day cycles. Bill offers up some gems on how to scale without becoming bureaucratic, explains why "professional managers" kill startups, why peer feedback beats manager reviews, and why bureaucracy isn’t a virus tha...
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% stock price drop, Vlad shares how he stays unflappable when everything is falling apart. We go deep on why "it's always wartime" should be your default mindset, not the exception. Vlad breaks down how he maintains breakneck speed at scale, why he limits planning t...
Winston Weinberg, CEO of Harvey, discusses the realities of scaling from zero to a $190M run rate, highlighting the inherent chaos and the need for constant reinvention every four months. He shares unconventional strategies for go-to-market, including cold-messaging thousands of lawyers and deliberately targeting the hardest enterprise law firms first. The episode also delves into his unique hiring criteria, his philosophy on leadership, and the crucial roles of a COO and Chief of Staff in managing hypergrowth.
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 his leadership, Palo Alto has become one of the most successful platform companies in enterprise software. In this episode, Nikesh and I go deep on what it actually means to be a modern CEO. We talk about why founders should sometimes not listen to customers, wh...
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 calls he’s had to make in the CEO seat, including the difficult decision to wind down Goldman's consumer banking ambitions. His perspective coming from a 156-year old banking giant is a little different than the common Silicon Valley wisdom. Hear why he thinks exp...
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 plan...
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 Intuit’s track record with SMBs. I even had the chance to shadow one of its former CEOs, the legendary Brad Smith.In this episode, Sasan and I talk about what it takes to reinvent a legacy company, what he learned shadowing Amazon’s Andy Jassy, and why curiosit...
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 build Rippling, a $17 billion juggernaut that blows his prior success out of the water. Parker has advice for founders: from productively harnessing the chip on your shoulder, to maintaining fast operational velocity to why you need founder-minded people on yo...
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
