Show Notes
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.
More from Long Strange Trip: CEO to CEO with Brian Halligan
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.
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.
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.
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.
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.