Long Strange Trip: CEO to CEO with Brian Halligan

Sequoia Capital
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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.

Episodes

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

    1D AGO

    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 prioritizing product, Kaz shares his unconventional playbook and approach to life. We go deep on why most enduring companies are built on "first derivatives" of their core business and not the obvious thing everyone focuses on. Kaz explains why he reads the Bible every day, how overriding life's defaults requires going full force (not halfway), and why founder mode means taking responsibility for outcomes, not processes. He breaks down the mechanics of the Opendoor turnaround, why he tethered his compensation to stock performance, and how he’s making the company AI-native. Essential listening for understanding true founder mode, or for anyone building something that matters.

    1h 3m
  2. Ben Horowitz On What Makes a Great Founder

    FEB 26

    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 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 manage people who may have more experience than you. Ben goes deep on “constructive confrontation” and why running away from the truth to preserve feelings is one of the most dangerous things you can do in a tech company. He explains why bad news has to travel fast, how decision debt paralyzes organizations, and why hesitation, not lack of intelligence, is what usually gets CEOs replaced. We also dive deep into hiring, especially the VP of Sales role founders mess up more than any other. Ben breaks down why great sales leaders qualify you in the interview, why references matter more than charisma, and why selling a hard product builds a different kind of operator. Along the way, we cover the psychology of being a first-time CEO, what Zuckerberg, Jensen, and Elon actually have in common, why culture is defined by behavior not values, and why feeling like you don’t know what you’re doing is more normal than most founders admit.

    49 min
  3. Bayer’s Bill Anderson: Turning a 168 Year-Old Tanker Like a Speedboat

    FEB 12

    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, 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 that infects healthy companies but rather something that grows from within the heart of your org chart. If you're scaling from 100 to 1,000 employees and want to avoid the death spiral that slows most growing companies, this is essential listening. Bill's created a playbook for organizational transformation that challenges what you think you know about building companies.

    1h 13m
  4. The Wartime CEO: Vlad Tenev of Robinhood

    JAN 29

    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% 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 to days instead of weeks, and how product events create forcing functions that keep thousands of employees moving with startup urgency. He discusses the counterintuitive truth that, if you need something done fast, you should give it to your busiest person.  We also explore the mechanics of rebuilding trust after very public failures, why co-CEOs might actually work better than investors think, and how Vlad stays connected to customers despite leading 15,000 employees. This conversation is essential listening for any founder trying to build resilience, any operator at a scaling company, or anyone who wants to understand what separates good CEOs from legendary ones.

    43 min
  5. Harvey CEO Winston Weinberg: Why You Should Reinvent Yourself Every 4 Months

    JAN 15

    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 intensity and willingness to do uncomfortable things on a weekly basis. Winston shares how he cold-messaged thousands of lawyers to land his first customers, why he deliberately chose the hardest enterprise law firms as his first target customers, and how he thinks about hiring and org structure when everything breaks every four months. We also explore his unconventional background - he wasn't a developer, was new to the legal industry, and figured out sales from scratch. It's raw, honest, and incredibly practical for any founder navigating (or hoping to navigate) the chaos of hypergrowth.

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

    JAN 8

    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 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, why most M&A fails, and how Palo Alto built a multi-platform business by betting big (and early) on second acts. Nikesh breaks down his very unconventional approach to acquisitions, where founders run the acquiring company’s teams, not the other way around. He explains how platform companies are built one decisive product insight at a time, why “more features” is often a trap, and how great CEOs balance product obsession with go-to-market reality. We also spend time on leadership psychology: imposter syndrome, conviction, risk appetite, and how to project confidence while you’re still figuring things out, and how to remain physically and emotionally healthy while you do it. If you’re a founder, an operator, or an aspiring CEO thinking about second acts, platforms, or scaling yourself along with your company, this episode is a masterclass.

    1h 5m
  7. Goldman Sachs CEO David Solomon: What Startup Founders Get Wrong About the CEO Job

    12/18/2025

    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 s****y 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 experience is vastly underrated in Silicon Valley, why "smart enough" matters more than being the smartest person in the room, and why serendipity and timing play bigger roles in being a great CEO than people realize. David reflects on mentorship from Lloyd Blankfein and Hank Paulson and how he thinks apprenticeship culture will evolve with AI. There are some great, unexpected lessons here for founders who are scaling, confronting the messy reality of building enduring companies.

    57 min
  8. Scaling AI Rocketships: ElevenLabs’ Mati Staniszewski & Lovable’s Anton Osika

    12/11/2025

    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 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.

    57 min
  9. Intuit CEO Sasan Goodarzi’s Grown-Up CEO Playbook

    11/20/2025

    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 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 curiosity and grit matter more than raw talent. We talk about how to run a grown-up company without losing speed, from the mechanisms Intuit uses to challenge its own assumptions to the ways he stays close to customers through “follow-me-homes.” Sasan also shares his approach to winning in the SMB market, building effective channel partnerships, and creating second acts that actually succeed. He even tells the story of how Intuit was four years late to SaaS and still managed to come out stronger. Sasan shows that if you love the customer problem and keep disrupting yourself, you can stay young even after 40 years in business.

    49 min
  10. Parker Conrad’s Revenge Fantasy

    11/13/2025

    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 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 your team instead of manager-minded people—even among your managers. And yes, he spills the dirt on Deel.  Parker is one of the new greats who is tearing up the old CEO rulebook and writing his own. - Brian Halligan, Sequoia Capital

    1h 17m

  11. 11/11/2025

    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 juggernauts like Robinhood and Rippling, to 150-year-old behemoths like Goldman Sachs.Watch at:  https://www.youtube.com/sequoiacapital

    1 min

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About

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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