Nick Kokonas on Dynamic Pricing for Time-Slotted Businesses
Nick Kokonas explains why geofenced dynamic pricing across time-slotted businesses is a multi-billion dollar opportunity founders miss.
How to find your arbitrage (from the guy who’s done it 3x)
With Shaan Puri, Nick Kokonas · Sunday, November 1, 2026
Shaan Puri interviews multi-disciplinary entrepreneur Nick Kokonas about finding high-conviction arbitrage across trading, hospitality, and software. Kokonas explains how he generated $100M+ trading options by exploiting latency between Chicago and New York, how he and Grant Achatz created world-renowned restaurant Alinea through relentless experimentation and theatrical principles, and how he challenged traditional M&A bankers when selling Tock for hundreds of millions.
Key takeaways
- Nick Kokonas generated over $100M trading options by exploiting latency between Chicago and New York before applying those same principles to hospitality. Read more →
- Nick Kokonas found chef Grant Achatz at Alinea at 6:00 a.m. testing 20 variations of a single sauce labeled on blue tape to isolate the winning preparation. Read more →
- Nick Kokonas generated over $100M trading options by exploiting latency between Chicago and New York, but walked away after realizing that mastering an industry makes founders vulnerable to hungrier newcomers. Read more →
- Nick Kokonas generated over $100 million in a single year trading options by exploiting latency between Chicago futures and New York exchange-traded funds like the QQQ. Read more →
- Nick Kokonas decided to sell Tock to Squarespace when pandemic growth peaked, knowing the company could not repeat a 200% annual growth rate the following year. Read more →
5 articles from this episode
Nick Kokonas on Alinea: Greatness Requires 99% Failure
Nick Kokonas explains why Alinea's Grant Achatz made 25 sauces at dawn, and how raw iteration volume beats intuition in startups.
Nick Kokonas on the Tingle of Nausea Risk Metric
Nick Kokonas explains why career expertise is a trap and shares the risk framework he used across trading, Alinea, and Tock.
How Nick Kokonas Used Jameson to Make $100 Million
Nick Kokonas found a regulatory loophole and bribed union workers with whiskey to build a $100M options arbitrage engine.
Nick Kokonas on Selling Tock: How to Run a 3-Day M&A Sprint
Nick Kokonas bypassed external bankers to sell Tock in three days. Here is his playbook for running an internal M&A diligence sprint.
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