Long Strange Trip: CEO to CEO with Brian Halligan

Afleveringen

1. Crusoe CEO Chase Lochmiller: Turning Stranded Energy Into Intelligence

   29 oktober 2026 · 1 uur 1 min

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   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 just closed a round at a $31 billion valuation, and he got there by selling off the Bitcoin mining business that was paying the bills. Lees meer

   Chase explains why Crusoe is modeled on Exxon, not a cloud provider, and why he partners with companies that look like competitors. He makes the case that a company that outgrows the person who got it there is the rule, not the exception, and that CEOs almost always fire too slowly. He also talks candidly about hiring a coach, working hard to become a polished speaker when it didn’t come naturally, and why the data center industry’s biggest problem is a marketing problem.

   I meet with a group of Sequoia founder CEOs between 20 and 2,000 employees, and one of them told me his business is becoming dizzyingly complex beneath him. Chase has the clearest answer I’ve heard for how to hold that in your head.

   And yes, we talk about summiting Everest.

   0:00 – Introduction

   2:12 – The boiling frog: how a founder holds a 2,000-person company in his head

   8:16 – DRIs, the weekly staff meeting, and saying it until you're sick of it

   11:19 – Urgency at scale: Elon's "change the world or die tomorrow" tension

   14:55 – Startups die of suicide, not homicide

   19:29 – Energy first: flared gas, Iceland hydro, and nuclear

   23:26 – Bitcoin to AI was the plan all along

   32:36 – Polish is learned: coaches, public speaking, and Felicis's self-improvement budget

   37:48 – Firing too slowly, and when the company outgrows the person

   42:39 – Welders and AI researchers, the data center backlash, and mining for bad news

   50:54 – Everest: designing around the Khumbu Icefall's stochastic risk

   57:31 – Brian's takeaways

2. Luca Ferrari: The Operating System Behind Bending Spoons

   8 oktober 2026 · 1 uur 6 min

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   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. Lees meer

   Bending Spoons got 800,000 job applications last year and hired fewer than 300 people. Luca runs hiring the way a quant runs a portfolio — hundreds of signals tested against future performance — and he's blunt about what the data says. Harvard and Stanford barely predict anything. Interviews are the worst signal in the process unless they're scripted. The best candidates were politically active as teenagers and stopped in their 20s. He hires for slope over experience, which is why a 25-year-old routinely shows up to run a company Bending Spoons just bought, and why he thinks experienced hires from big tech lose motivation and struggle to adapt. He also explains why Bending Spoons has no executive team, why the burden of proof always sits with whoever wants to add complexity, and why he stayed in Milan on purpose.

   I called three founders whose companies Luca acquired before this interview. All three, unprompted, said the same thing: exceptionally high integrity. His answer about where that comes from is the most honest closing I've had on this show.

   Chapters:

   0:00 – Introduction

   1:13 – The Bending Spoons model: buy to hold forever, then rebuild from the ground up

   8:07 – 800,000 applicants, fewer than 300 hires: industrializing talent density

   13:45 – Hiring like a quant trader: hundreds of signals, scripted interviews

   21:45 – Why strategy and talent trump org structure

   25:34 – Leader or manager? Head in the clouds, feet on the ground, but never both at once

   30:38 – Slope over experience: why 25-year-olds run the companies Bending Spoons buys

   41:08 – Radical candor, the 360 that found Brian's bugs, and picking one flaw a year

   47:00 – No exec team, no sacred org chart: whoever is CEO should rewrite the system

   51:27 – Quest…

3. Databricks’ Ali Ghodsi Never Wanted to Be CEO. Now He’s Among the Best

   17 september 2026 · 1 uur 14 min

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   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 even give him a CEO salary. When I had Ben Horowitz on this podcast and asked him who the best CEO in Silicon Valley is outside his own portfolio, he didn't hesitate. He said Ali. Lees meer

   We get into how he actually runs the place: find the single biggest bottleneck in the company, then put an absurd, disproportionate amount of attention on it for two or three years. That's how the Lakehouse category got built, back when the strategy consultants, his own sellers, and most of the internet were laughing at the name. Ali breaks down the playbook he ran against Snowflake, why he's said no to phenomenal executives who still hold a grudge about it, and what he learned shipping code himself.

   He's also blunt that conflict aversion disqualifies you from this job. I over-indexed on being liked at HubSpot. Ali doesn't.

   0:00 – Introduction

   1:22 – The secret CEO search and why the board bet on a founder

   4:11 – Professor or CEO? Always taking the harder option

   8:18 – Build your own playbook and pour everything into one bottleneck

   12:16 – Killing PLG and learning what great enterprise sellers actually have

   19:09 – Hiring ahead of the curve: sales leaders, execs, and back-door references

   27:02 – The Snowflake rivalry: study your enemy, never copy them

   33:22 – Lakehouse: conviction, ridicule, and the case for second acts

   41:02 – The killer instinct and why conflict-averse CEOs fail

   44:10 – Dunbar's number and rethinking the org chart around AI

   48:00 – AGI is already here — enterprises just use it as a chatbot

   52:55 – Does he still code? Two days for a connector vs. three quarters

   57:18 – A day in the life, and why the Monday meeting isn't theater

   1:04:53 – Why Databricks will go public, just not yet

   1:08:09 – Get over conflict aversion, or…

4. The Philosopher CEO | Clay Co-Founder Kareem Amin

   23 juli 2026 · 1 uur 9 min

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   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. Lees meer

   Kareem builds from what he calls "a place of wholeness" rather than lack — nothing to prove, no enemy to beat. It makes him sound like a philosopher, but the operating instincts underneath are sharp. He spent roughly five years wandering before Clay clicked, and his takeaway is that the hard part of building isn't working hard — it's the courage to commit to one idea and stop listening to everyone else, customers included. He flipped every assumption in his market: sell to technical "go-to-market engineers," charge for usage instead of seats, pick power over simplicity.

   We both created categories, in opposite ways. I flogged "inbound marketing" with a book, a conference, and relentless content. Kareem coined "go-to-market engineering" and then refused to take credit, letting agencies own it because a category has to be bigger than you. We also get into his "momentum detective" theory of the CEO job, why he's deleting his standing one-on-ones, and why apologizing is one of his sharpest tools. There's no single way to run a company. Kareem is my proof.

5. Kalshi’s Tarek Mansour vs. the Federal Government

   9 juli 2026 · 1 uur 3 min

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   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. Lees meer

   Kalshi spent years walking through the desert. The CFTC pocket-vetoed its election markets ahead of the 2022 midterms, people left, and the company took a layoff while the government piled on audits and enforcement actions. Death by a thousand paper cuts. Instead of pivoting, Tarek and co-founder Luana Lopes Lara sued the federal government against the guidance of nearly all their investors and advisors. They won, three and a half weeks before the 2024 election, and Kalshi now claims 95% U.S. market share in prediction markets.

   We get into how two co-founders run 150 people with nearly everyone reporting directly to them, why it’s intentionally chaotic, why the two of them disagree by design, and Tarek's poker-player theory of expected outcome vs. outcome. He also breaks down his obsession with marketing timing - like launching the Timothée Chalamet spot 12 hours after the Knicks news broke - and his "hole in the ship" rule: a founder has to be the one staring at the leak.

   Tarek and Luana's dynamic reminded me a lot of me and Dharmesh at HubSpot: total opposites, and one plus one equals three.

6. David Senra: Mute the World and Build Your Own

   4 juni 2026 · 57 min

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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. Lees meer

   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 Daniel Ek believes founder-problem fit matters more than product-market fit. We get into the idea that the best founders are driven by control, not money - and why selling your best company and trying to recapture the magic at 60 almost never works.

   David’s perspective on overcoming negative self-talk: at some point you have to change your fuel source from something that punishes you to something that generates.

   If you've ever wondered whether the founder mythology is real, David has read more of the source material than anyone alive.

7. Notion’s Ivan Zhao: The Refounder

   21 mei 2026 · 1 uur 3 min

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   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. Lees meer

   We get into why Ivan rebuilt his engineering org around a barbell — super junior ICs paired with very senior architects — which is the opposite of what most AI-pilled CEOs are doing right now. He explains why building with language models is "more like brewing beer than engineering a bridge," and how Notion's first candidate interview no longer involves a resume.

   Ivan is the king of refoundings. He's done it twice, once from a small apartment in Kyoto with five employees left, once from Cancun the day he got early access to GPT-4. When I was running HubSpot, I described our scale-up years as boring compared to what's happening now. Ivan's advice for any CEO who's calcified and wondering if it's time to blow it up: feel the AGI first, then trust your body when it tells you to move.

   00:00 Introduction
   02:22 From Founder Mode to AI Org
   11:00 Hiring for Taste and Agency
   24:28 Refounding Notion in Kyoto
   30:27 Craft Versus Commerce
   32:26 When to Refound
   34:07 GPT-4 Refounding Shock
   45:35 Leadership and Founder Energy
   53:17 Sales Culture and Closing Thoughts

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

   7 mei 2026 · 1 uur 8 min

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   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. Lees meer

   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 problems with processes ("the launch checklist was 17 pages long") and started solving them with DRIs and operating control. How he managed by walking around the engineering floor at 9:30 PM to figure out what was actually getting built. And the Steve Jobs trick he stole from Pixar for finding out what's really going on inside a team.

   Dick is candid about the misses, too, including trying to buy Instagram for around $700 million before Facebook did, and his own struggles to fire fast. When I was running HubSpot, I fired slow almost every time and regretted it. Dick did better, but he'll tell you it never gets easier.

   If you're scaling past 150 people and feeling the organizational barnacles build up, this one's for you.

9. What Founders Can Learn About Excellence From MIT President Sally Kornbluth

   16 april 2026 · 44 min

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   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. Lees meer

   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 the lollipop of mediocrity, you suck forever. That's how MIT has operated for 150+ years. We get into how you actually hold the bar as you scale, why most founders drop it without realizing it, and what to do once you've dropped it.

   We also get into the crisis playbook – staying calm on the outside when you're screaming inside, why explaining is losing, and why having a board that's truly behind you is the most underrated variable in whether you survive. The board backing her was the pivotal moment, full stop.

   Other things we cover: what managing PhD students taught her about leading without being overbearing, the 5:1 praise ratio and why it doesn't cost you anything, how she told the federal government "no thanks" on their higher ed compact, and what AI actually means for education, including why writing is still thinking.

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

    2 april 2026 · 1 uur 4 min

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    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 corporate hierarchy isn't just inefficient — it's obsolete. Jack made one of the toughest calls in recent business history: cutting 40% of his workforce and rebuilding the company from the ground up around what he calls an AI "intelligence layer." We get into how that conversation went down, the math they used to land on a number, and why he's convinced that acting from a position of strength beats reacting from one of weakness. Lees meer

    Jack breaks down his vision for simplifying into just three roles, and what it means to replace a pyramid org chart with a circle — AI at the center, and people at the edge. Roelof, who helped think through the restructuring, shares his perspective on how AI-native startups are building differently, and what CEO qualities are timeless.

    I've eliminated org charts before. I know how hard this is. But Jack is doing something I never had the tools to pull off. If you're a founder wondering whether your hierarchy is working for you or against you, this one will make you uncomfortable in the best way.

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