People spend a lot of time arguing about purchase price. But in many small business acquisitions, that is not the most dangerous number in the room. The most dangerous number is the one underneath it: the cash flow everyone assumes is there.
That is where bad deals hide. Not in the headline number. Not in the LOI. Not in the broker deck.
They hide in the earnings story. Because once the conversation starts, everyone has a version of that story: The seller believes the business is stronger than the reported numbers suggest. The buyer believes they can improve operations immediately. The broker believes the adjustments are obvious. The lender hopes the cash flow coverage works. And somewhere in the middle, the valuation has to determine what is actually transferable.
That is where things get uncomfortable. Because “cash flow” in a deal often includes a little too much imagination:
- expenses that supposedly will disappear
- compensation that supposedly can be reduced
- capex that supposedly is not a real issue
- customer concentration that supposedly is manageable
- revenue trends that supposedly will continue
- rent arrangements that supposedly do not matter
That word—supposedly—has destroyed a lot of value.
I have seen many transactions where the price itself did not initially alarm anyone. What should have alarmed them was how much faith the deal required in adjusted or future earnings.
That is why normalized free cash flow matters so much. Not theoretical cash flow. Not seller-presented cash flow. Not emotionally preferred cash flow. Normalized, supportable, economically grounded cash flow.
Because if the earnings do not hold, the value does not hold. And if the value does not hold, the transaction becomes fragile the moment it closes.
This is one of the hardest truths in dealmaking: A business is not worth what people hope it will produce. It is worth what a rational buyer can reasonably expect to receive, adjusted for risk.
Everything else is negotiation theater.
