
Guest
Nick Kokonas
Owner, Tangle Ranch Vineyards
Built Chicago's Alinea Group and co-founded Tock, the restaurant reservations platform later acquired by American Express.
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Real Alpha has cut 6 moments of Nick Kokonas (Owner, Tangle Ranch Vineyards) talking, from an interview on My First Million published Oct 26, 2026.
What Nick Kokonas said
How to find your arbitrage (from the guy who’s done it 3x)
6 moments · 29 min
- 1:26:46
A restaurant group returned investors about 28 times their investment
“And then they got 8x their initial investment walking out the door, right? So I think overall it was like 27 or 28x.”
at 1:28:05 - 1:32:51
He took control of diligence to move a sale forward
Facing a sale deadline, Kokonas and his team handled 896 diligence questions themselves and finished in three days. They also cut out an investment bank, keeping control of the process and its incentives.
- 36:02
The trading firm expanded before it built management systems
“we didn't know how to build a layer of management and accounting and we're terrible at that”
at 37:03 - 43:13
Restaurant prices should vary by time and location
“I genuinely believe that geofence, meaning localized dynamic and variable pricing for time-slotted businesses is something that someone's going to make hundreds of billions of dollars with.”
at 46:58 - 56:41
Publishing Alinea's process built an audience before opening
“And so I was like, let's just open source the whole business plan.”
at 57:57 - 1:10:34
Magician techniques can improve restaurant recommendations
“if you want to gain people's trust you don't sit across from them or stand across from them you will stand next to them”
at 1:12:46
- 1:26:46