Notion’s Ivan Zhao: The Refounder

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 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.

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'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 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.

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 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 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

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 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 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.

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 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 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.