Nick Kokonas

Kokonas says his trading firm made over $100 million in one year from the New York–Chicago arbitrage.

“Well, I think that year we made over $100 million”

My First Million: How to find your arbitrage (from the guy who’s done it 3x) ft. Nick Kokonas (Oct 26, 2026) · Listen from 30:09

Kokonas says he deliberately shut down the initial arbitrage to avoid provoking the big investment banks, preferring modest gains over years.

“We're much better off picking their pocket a little bit for years than we are just destroying them on day one”

My First Million: How to find your arbitrage (from the guy who’s done it 3x) ft. Nick Kokonas (Oct 26, 2026) · Listen from 30:54

Kokonas argues that every arbitrage comes down to timescale.

“I am now convinced that every arb is just about time scale”

My First Million: How to find your arbitrage (from the guy who’s done it 3x) ft. Nick Kokonas (Oct 26, 2026) · Listen from 25:00

Kokonas predicts in-person experiences will become more important every year as AI spreads.

“In-person experiences are going to be more important every single year from now till we hit deep, like the holodeck”

My First Million: How to find your arbitrage (from the guy who’s done it 3x) ft. Nick Kokonas (Oct 26, 2026) · Listen from 2:05:19

Kokonas says Strange House has secured a 90,000-square-foot space beneath Wall Street after lengthy lease negotiations.

“90,000 square feet underneath Wall Street in Manhattan, six months of negotiating the LOI on the lease”

My First Million: How to find your arbitrage (from the guy who’s done it 3x) ft. Nick Kokonas (Oct 26, 2026) · Listen from 2:00:50

Kokonas says Alinea Group investors received quarterly distributions from 2005 until he sold the group in 2023.

“Our investors got quarterly distributions from the time I started it in 2005 all the way to when I sold it in 2023”

My First Million: How to find your arbitrage (from the guy who’s done it 3x) ft. Nick Kokonas (Oct 26, 2026) · Listen from 1:29:34

Kokonas argues that excellence comes from producing many mostly bad attempts, as with Grant Achatz testing many versions of a sauce.

“You have to know what great is. And knowing what great is, is making mostly shit 99% of the time”

My First Million: How to find your arbitrage (from the guy who’s done it 3x) ft. Nick Kokonas (Oct 26, 2026) · Listen from 54:04

Kokonas believes localized dynamic pricing for time-slotted businesses will be worth hundreds of billions of dollars to someone.

“geofenced, meaning localized, dynamic and variable pricing for time slotted businesses is something that someone's going to make hundreds of billions of dollars with”

My First Million: How to find your arbitrage (from the guy who’s done it 3x) ft. Nick Kokonas (Oct 26, 2026) · Listen from 47:00

Kokonas argues, against calls to ban dynamic pricing, that the best way to avoid gouging is to price dynamically as quickly as possible.

“But the best way to do that is to dynamically price things as fast as you possibly can”

My First Million: How to find your arbitrage (from the guy who’s done it 3x) ft. Nick Kokonas (Oct 26, 2026) · Listen from 46:24

Kokonas told Napa grape growers they were wrong to assume decades of rising prices would never reverse.

“you had 30 years up into the right and you thought you weren't going to get kicked in the face at some point”

My First Million: How to find your arbitrage (from the guy who’s done it 3x) ft. Nick Kokonas (Oct 26, 2026) · Listen from 1:45:23

Kokonas says his team answered Squarespace's roughly 900-question diligence list in three days without an investment bank.

“And we did that whole list in three days. We just stayed up”

My First Million: How to find your arbitrage (from the guy who’s done it 3x) ft. Nick Kokonas (Oct 26, 2026) · Listen from 1:34:33

Kokonas argues that Michael Lewis's Flash Boys was wrong because traders tell journalists only strategies that no longer work.

“When he finally wrote about something I actually knew about, I went, this is all wrong. Flash Boys is all bullshit”

My First Million: How to find your arbitrage (from the guy who’s done it 3x) ft. Nick Kokonas (Oct 26, 2026) · Listen from 1:31:36

Kokonas criticizes a famous TV chef who claimed during COVID that restaurants make only 2–3%, saying the chef was not a skilled restaurant operator.

“But he was a very successful TV chef, not a very successful restaurant owner”

My First Million: How to find your arbitrage (from the guy who’s done it 3x) ft. Nick Kokonas (Oct 26, 2026) · Listen from 1:29:07

Kokonas says he deliberately designs software with dead ends to guide users on a journey, contrary to most UX designers.

“I like to build dead ends in software that every software designer hates”

My First Million: How to find your arbitrage (from the guy who’s done it 3x) ft. Nick Kokonas (Oct 26, 2026) · Listen from 1:09:44

Kokonas says Alinea adopted a magician's technique of having servers stand beside diners, on their side, rather than across from them.

“We're going to start doing service in a way where we are on the side of the diner”

My First Million: How to find your arbitrage (from the guy who’s done it 3x) ft. Nick Kokonas (Oct 26, 2026) · Listen from 1:13:22

Kokonas argues that being open about why you are doing something wins as long as it is authentic.

“the more open you can be about why you're doing it, as long as it's authentic, you win. Period”

My First Million: How to find your arbitrage (from the guy who’s done it 3x) ft. Nick Kokonas (Oct 26, 2026) · Listen from 1:02:06

Kokonas argues that expertise is a trap because a hungrier non-expert will eventually displace you.

“expertise is such a trap, right? It's such a trap. And you know that a non-expert is going to come after you”

My First Million: How to find your arbitrage (from the guy who’s done it 3x) ft. Nick Kokonas (Oct 26, 2026) · Listen from 21:37