How to find your arbitrage (from the guy who’s done it 3x) ft. Nick Kokonas
October 26, 2026 · 2 h 7 min
🎙️ Full episode
DEBRIEFWritten and voiced by AI from the episode's audio
Nick Kokonas has built three fundamentally different businesses—trading, restaurants (Alinea), and software (The Infatuation/Tock)—by applying the same principle: finding arbitrages across different time scales. Starting with just $60 on the trading floor in Chicago, he identified pricing gaps between New York and Chicago markets, eventually scaling to $100+ million in annual profits. He then left finance to create Alinea, one of the world's best restaurants, by studying theater, magic, and customer psychology instead of traditional restaurant playbooks. He later applied dynamic pricing insights to build Tock, which revolutionized how restaurants manage reservations. Throughout his career, Kokonas has embraced discomfort as a signal—not of failure, but of growth. He deliberately seeks the "tingle of uncomfortableness" and reinvents himself every decade to avoid expertise becoming a trap. His philosophy centers on showing up (consistently and early), studying adjacent industries for fresh ideas, making sauces 99 times to find one great one, and viewing every business as fundamentally about finding or closing gaps in time, information, or experience. He's now building "Strange House," an immersive magic theater experience beneath Wall Street that merges his interests in illusion, human connection, and experiential design.
🎧 AI Debrief
Show notes
Database on how long it takes to become a millionaire: https://clickhubspot.com/tyvc
Episode 876: Shaan Puri ( https://x.com/ShaanVP ) sits down with Nick Kokonas ( https://x.com/nickkokonas ) to talk about finding arbitrages and how to win an many different games.
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Show Notes:
() Intro
() How I Became a Trader With $60K
() Surviving Day 1 of Anything
() The Comfort Trap
() Finding Your Arb
() No Boats. No Women. No Drugs.
() Showing Up
() Everything Is an Arbitrage
() Greatness
() Working Backwards
() The Magic of Alinea
() Controlling Attention
() Remixing Old Mechanics
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Links:
• Alinea – https://www.alinearestaurant.com/
• Tock – https://www.exploretock.com/
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My First Million is a HubSpot Original Podcast // Brought to you by HubSpot Media // Production by Arie Desormeaux // Editing by Ezra Bakker Trupiano /