The Interview That Never Happened — Part V: The Deal You Think You’re Making

Structure decides what you keep long after the headline number fades

Joe’s next question sounds like it belongs to lawyers and bankers: “What should entrepreneurs know about deal structure and negotiation when it comes to selling their business?” Most founders hear that and think, I’ll figure it out when I get there.

That’s a dangerous assumption.

Because this is one of the few moments in business where success in operating does not translate into competence in execution. You can build a great company and still get outmaneuvered in the deal that defines its value.

The Game You’ve Never Played

There’s an asymmetry here that’s easy to underestimate. Buyers do this for a living. You do it once, maybe twice. They know the patterns, the pressure points, the sequence of moves. You’re walking into something that looks like a negotiation but is really a system—a system you’ve never seen before.

That alone should tell you something: this is not the place to rely on instinct or past success. This is where you bring in people who have already lived through it, many times.

In 2004, I hired an investment banker. I paid a market price for expertise I did not have. In 2008, when the business was ultimately sold, I was partnered with First Atlantic Capital, and we were sitting on the same side of the table. I already knew I was in good hands. That difference matters more than most people realize.

Price Is the Headline. Structure Is the Story.

Most entrepreneurs focus on the number. Sophisticated buyers focus on the structure. And the uncomfortable truth is this: the number you agree to is not the number you take home. Structure decides timing, risk, control, and ultimately what that headline is actually worth to you.

Take earnouts. I’ve never been a fan. I understand why they exist, but unless you are already getting what you consider your minimum at close, you are taking on risk you may not fully control. You’re tying part of your outcome to a future that may no longer be entirely yours to influence.

Contrast that with equity. In my case, I wanted to keep as much equity as I could while still getting the capital needed to grow. That alignment mattered. If private equity succeeded, I succeeded. That’s a very different position than hoping to earn what you thought you already sold.

Structure is not just financial engineering. It’s philosophy.

You Are Not Paying for Advice

The instinct to avoid expensive advisors is understandable. The fees feel large, especially in the moment. But that thinking misses the point entirely. You are not paying for advice. You are paying for what you don’t know that you don’t know—for the pattern recognition that only comes from having done this over and over again, for the checklist that exists in someone else’s head that you don’t even realize should exist.

Think about a pilot. Every flight begins with a checklist. It’s not optional. It’s not improvised. It’s muscle memory built from thousands of repetitions. Now imagine reading the manual once and deciding to fly the plane yourself. That’s what most entrepreneurs are doing when they try to handle deal structure and negotiation on their own.

I didn’t pay for one thing.

I paid for 10,000 hours I don’t have—and never will.

The Emotional Trap

There’s another layer that makes this harder than it looks. You are negotiating something you built. They are negotiating something they can walk away from. That difference shows up everywhere—in patience, in pressure, in decision-making. Without the right people around you, it’s easy to concede ground you don’t even realize you’re giving up. This is not about intelligence. It’s about position.

Who’s Actually on Your Side?

In 2004, I hired expertise. In 2008, I had alignment. Both worked, but in different ways. One was transactional support. The other was a partner whose outcome was tied directly to mine. That’s the real question you need to answer: who is actually sitting on your side of the table?

Because not all “help” is equal.

You are not looking for someone who understands deals in general. You are looking for someone who understands your deal, your situation, your goals—and knows how to navigate that specific terrain. A great firm that isn’t right for you is the wrong choice.

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🌱 Seed Thought: The most important parts of a deal are the ones you don’t yet understand. That’s exactly why you shouldn’t be doing them alone.