Nobody Warns You About Deal Fatigue

The way selling a company gets described, y ou would think it happens in an afternoon. There is a handshake, a signing, a wire transfer, and then presumably a vacation.

What actually happens is six to twelve months of grinding process while you are still expected to run the business and hit your numbers.

I have been through the full cycle twice, first selling my technology services firm to a private equity group in 2021, then working with that group to sell again to a strategic buyer in 2024. Both times, the hardest part was not the negotiation. It was the duration.

Here is what nobody prepares you for

Diligence does not end. You will produce financials, contracts, employee records, customer concentration analyses, and tax documents. Then you will produce revised versions because the buyer's team changed. Then a new request will arrive for something you already sent three months earlier. Each individual ask is reasonable. The cumulative weight of them is not.

Meanwhile the business still has to perform. Buyers are watching your monthly numbers throughout the process, and a soft quarter mid-diligence can trigger a renegotiation of price. So, you are running a full-time transaction and a full-time company simultaneously, usually without telling most of your team what is happening.

That last part is its own kind of exhausting. You are carrying the single biggest thing happening in your professional life and you cannot discuss it with the people you spend every day with.

The real danger is what all of this does to your judgment

By month eight, you want it done. Not for good reasons, just to make it stop. This is precisely when buyers tend to introduce a revised working capital calculation, or a larger escrow holdback, or an earn out structure that shifts more of your proceeds into future performance. Those changes arrive when your resistance is lowest, and they are frequently accepted by founders who would have pushed back hard in month two.

I am not suggesting buyers are acting in bad faith. Most are not. But their team does this for a living and rotates fresh people onto the deal. You are doing it once, alone, on top of your actual job. The asymmetry is real, and fatigue is where it costs you money.

A few things that help

Build your team early. A good investment banker and an experienced M&A attorney absorb enormous amounts of process load. Founders who try to save that fee usually pay for it many times over in worse terms.

Bring your CFO or a trusted senior person inside the tent as soon as you responsibly can, so you are not the only person carrying it.

Set your walk-away terms in writing, at the start, while you are still clearheaded. Then treat that document as binding on your future exhausted self.

And protect your health deliberately. Sleep, exercise, and time away from it are how you preserve the judgment you are going to need in month nine.

The deal will take longer than you think. Plan for the endurance, not just the outcome.