Try Pro free

My First Million · 5 min · Oct 26, 2026

He took control of diligence to move a sale forward

Facing a sale deadline, Nick Kokonas and his team handled 896 diligence questions themselves and finished in three days.

The episode’s best minutes

Full analysis
  1. 1:26:46A restaurant group returned investors about 28 times their investment3 min
  2. 1:32:51He took control of diligence to move a sale forward5 min
  3. 4 more moments in the full episode
Up next · The Shawn Ryan ShowRocket parts can double as data center hardware6:49

Takeaways

  1. The team color-coded and assigned the diligence questions.
  2. They completed the 896-question list in three days.
  3. Kokonas questioned whether the advisers' incentives matched the deal.

About this segment

Facing a sale deadline, Nick 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.

Nick Kokonas

Nick Kokonas is an entrepreneur, options trader, restaurateur and software founder.

Built Chicago's Alinea Group and co-founded Tock, the restaurant reservations platform later acquired by American Express.

  • Shaan Puri, Host · Co-host, My First Million

    Sold Bebo to Twitch in 2019; co-founded the crypto newsletter Milk Road.

From “How to find your arbitrage (from the guy who’s done it 3x)”, Oct 26, 2026. Watch the full episode

Transcript

Transcribed by machine (Whisper) from the episode’s audio, so a word may be off here and there.

  1. 1:33:03

    where you kind of like took control of it entrepreneurially rather than being a passenger to the process. We had incredible growth during COVID. And the trader in me was like, we are going to lap this growth and we're still going to do well, but we're not going to go 200% next year. Right. This is my moment. Like it looks really good right now. And with technology, you know, you could have something that that's, you know, growing 200% a year.

  2. 1:33:33

    And then all of a sudden you grow 50% one year. And even though that's amazing, the world of M&A and VC just goes, oh, like you are on your way down and pretty soon you're going to be like a legacy. You're Comcast pretty soon, you know, even though it's not true. So Steve Bernacki, Jeff Kaplan, my COO, myself, the lawyers would go like, well, we just got the diligence list. And it's 896 questions.

  3. 1:33:57

    And we would convert it from Excel into Google Docs. And then Steve would go through and he would color code it all. And we would assign it to the people that could answer all the questions. And, of course, like the investment bankers and lawyers kind of thing would go, okay, well, this will take like four to six weeks. right and i was like we built dashboards for all this i could have it like two days but then they realize they ain't getting paid if it's in two days right right you know it's like they're billing hourly and there's four of them so they're incentive yeah you're at 3200 an hour or whatever every time you get on a zoom call with them and then you know the Investment bankers want whatever, 3% to 4% or whatever.

  4. 1:34:38

    So we just went, we don't need an investment bank. Like, there's nothing here that we can't figure out on our own. And of course, the board hated that idea. But we still had a controlling interest. And so I just said, like, awesome, we'll do it for 2%. Does that make you feel better? For real. So you were your own investment banker? Yeah. And I'm like, I wasn't going to do that, but they were so adamant that it was hard.

  5. 1:35:04

    And I said, well, you know, like, look, they're getting paid 4%. I'll save you 2%. We'll take it. And that way we'll be beholden. If we don't get it done, like you can, you know, we won't get paid. Which is weird. They should just say no to that. But they didn't say no. They said yes. And we did that whole list in three days. We just stayed up. You just locked yourself in a room, right? Locked yourself in a room.

  6. 1:35:24

    Did the whole thing in three days. There was like, you know, there was a lot of questions that were like unclear what this, what you're asking here, you know, or irrelevant. but and then they just went what is this we're like that's your diligence you got to tell the spock the spock story oh god there was i'm not letting you up okay yeah there was a guy on the other side we won't use his name or the firm but you know there'd be this is during covid too so they wouldn't be in person and there'd be like 30 people i mean i have screenshots zoom call zoom call of 30 people all lawyers all lawyers our side their side a couple people from squarespace and then the three of us basically and we knew the answers to all this stuff because we did it ourselves there's no one to parse it through whatever and so then i would just ask a question

  7. 1:36:11

    or steve would ask a question or jeff would ask a question and the lawyer would literally go i will take that to my client and i'd be like your client's on the fucking like i can see your like we're here we've got two weeks left let's not leave it till like and it had to be done one of the critical things and and the reason it got done is because they were going to go public the following quarter and all of their s1 information whatnot need to be locked down end of q1 which happened to be on march 31st okay like it actually followed the calendar year so march 31 we had to be done otherwise it was good not going to happen for six months to a year and maybe never right and finally i just looked and i was like hey spock shut the out and everyone even some people on his own team were kind of like you know kind of tried not to giggle but

  8. 1:37:00

    you could see them you know and i was taking screenshots the whole time because this guy it takes guts to say that to the other side well i was so angry because like did he wonder why you were calling him spot no no no no this was his entire strategy was simply to close at noon on the last day possible. Right. Because that's how they could get the most out of it. Right. And that's one of the you know, you were we were talking earlier, like one of the superpowers is not a superpower. It's just what what is this person's motivation if they're on your team?

  9. 1:37:35

    Even are they are your incentives aligned? I learned very quickly at Alinea that my manager's