We obsess over maximizing the number.
The banker presents three offers. The first is $47 million, all cash, close in sixty days. The second is $52 million with an earnout. The third is $58 million, but you’ll stay on for three years reporting to someone who doesn’t understand what you built.
Which one is worth more?
The math says $58 million. But math doesn’t measure what happens to your marriage during those three years. It doesn’t account for the innovative project you won’t start. It can’t quantify watching someone dismantle the culture you spent fifteen years building.
Maximum isn’t the same as optimal.
Here’s what the spreadsheet misses: You already have enough. Not enough to buy a yacht—enough to do the work that matters next. Enough to sleep well. Enough to say no to things that don’t fit.
The founder who takes $47 million and walks away might create more value in the world than the one who grinds through an earnout for an extra $11 million. Not because money doesn’t matter, but because freedom and energy and purpose matter differently at different stages.
The question isn’t “What’s the highest number I can get?”
The question is “What am I trying to buy with this exit?”
If the answer is time, autonomy, or the chance to build something new, then maximum might actually cost you everything you’re trying to purchase.
