Most of the calls I take from CPA firm owners evaluating a PE offer happen on a Tuesday or Wednesday evening. There is a reason for the timing, and it is not random.
By Tuesday evening, the second meeting with the buyer has happened. The number on the table is no longer hypothetical. The owner has been carrying the conversation alone for somewhere between three and ten days, and he has reached the point where his own thinking has stopped being useful to him. The calls usually come from a parking lot, a home office with the door closed, or a car in the driveway with the engine off.
The owners on these calls share a pattern that took me a few years to see clearly. They are not calling because they cannot do the math. They are calling because the math turned out to be the easy part.
The owner I worked with last spring had a $4.2M practice and a buyer offering 8.4x EBITDA. He had spent the previous weekend modeling the deal in a spreadsheet on his kitchen table. The numbers worked. His CPA brain had verified the numbers three different ways. He still could not sleep.
By the time we got on the phone, he had figured out what was actually keeping him up. It was not whether the deal was a good deal. It was a question he had not been able to phrase yet, and the question was: what does my firm become the day after the wire hits, and what do I become with it.
That question does not appear on a quality-of-earnings report. It does not appear in the LOI. It does not appear in any of the materials the buyer's team has sent over. And it is the only question that actually matters.
I have been on the inside of this profession for twenty years. I was the first customer success leader at an accounting SaaS company managing $20M in ARR. I ran a BPO serving 150+ US CPA firms for twelve years before that. I have sat across the table from hundreds of firm owners in moments of decision, and I have watched what happens after the decision more times than I care to count. The evening calls have a shape. The shape is consistent across firm sizes, across geographies, across whether the owner is 48 or 62.
What the owner is usually carrying, in the order it surfaces:
First, the deal looks better on paper than it feels in the chest. The multiple is real. The earnout is structured. The buyer has been respectful in every meeting. And yet there is a quiet weight that the spreadsheet does not capture, and the owner is starting to suspect the weight is the actual data.
Second, the people he could normally talk to about a decision this size are unavailable to him for this one. His spouse is supportive but careful, the way spouses are when they sense a decision has already been made and is being processed out loud. His partners are in different life stages and pulling in different directions, and any conversation with them turns into a negotiation rather than a reflection. His state society peers have opinions, but he has spent twenty years being the one with the answers in those rooms, and he is not going to be the one asking the question now.
Third — and this is the one that surprises owners the most when I name it — he has not yet figured out what he is selling. Not legally. Legally he knows. He is selling equity in a firm. But the firm is also the thing that has organized his identity for two or three decades. The thing that has explained him to his wife, his kids, his community, his chapter. The thing that has answered the question what do you do at every dinner party since 1998. He has not separated the equity sale from the identity transition, and the buyer's team is not going to help him separate them, because their job is to close the deal, not to close the chapter.
The owners who do well after the deal are the ones who run that separation before the wire hits, not after. The ones who do not — the ones I see most often a year later — are the ones who let the closing day be the day they discovered they had not done the work.
The work is not financial. The financial work is the easy part, and the buyer's team will help with that one because their incentives are aligned with the owner's on the math. The work is structural and personal and, in my experience, almost impossible to do alone. It requires someone who has been in the room before, who has no angle on the outcome, and who can ask the questions the owner has not been able to phrase yet.
Most owners do this work in two or three conversations. Sometimes one is enough. The conversations are not therapy, and they are not financial advisory. They are the conversation the owner has been trying to have with himself in the parking lot, externalized, with someone qualified to hear it.
If you are reading this and the parking lot detail registered with you in a way the rest of the article did not — that is the signal. The Tuesday evening call is the part of the work I do. The conversation is private, structured, and exists outside the deal team's incentives.
The number on the table will still be there next week. The decision underneath the number is the part most owners have not given themselves time to make.
DM open here. Mention the parking lot.
