The conversations we keep having
We spend a lot of time with founders who have already sold — sometimes to us, more often to someone else, sometimes years before we ever met. They are, almost without exception, willing to talk candidly about what they would do differently. The regrets are remarkably consistent.
None of them are about price. Price is the easiest thing to negotiate and the easiest thing to make peace with afterwards. The regrets are about everything else.
"I should have started preparing two years earlier"
The most common regret, by a wide margin. Not preparing the business — preparing themselves and the company for the conversation.
Two years is roughly the time it takes to build the things that materially increase value: a second-line management team that can run things without you, clean financials that survive diligence, contracted recurring revenue replacing handshake renewals, written documentation of how the business actually operates.
Owners who started this work at the point they decided to sell ran out of runway. Owners who started two years earlier had options.
"I chose the wrong buyer"
Usually not because the wrong buyer paid the most — although sometimes that is the case. More often because the seller did not interrogate, before signing, what the buyer would actually do with the business.
A buyer with a five-year fund horizon has different incentives than one with a perpetual horizon. A buyer who plans to consolidate has different priorities than one who plans to keep the brand. A strategic acquirer who needs your client list will treat your team differently than a financial buyer who needs your earnings.
These are not abstract distinctions. They show up in week three after close, when the new owner starts making decisions that the seller did not anticipate but that were entirely predictable from the buyer's structure.
The single question that would have changed most of these outcomes: what does this buyer need to be true in three years for this acquisition to be considered a success? The honest answer tells you almost everything you need to know.
"I did not give myself enough handover time"
Founders often negotiate the shortest possible transition because they want to be free. Three months later, they are taking calls from former employees who do not know who to ask, customers who feel abandoned, and a new owner who is learning the business at the same time as trying to run it.
Six to twelve months of active handover, with a clear end date, is almost always the right answer for a healthy transition. Three months is usually too little. An open-ended advisory role is usually too much.
"I did not protect what I cared about in writing"
The buyer made verbal commitments. The team would be kept. The office would stay. The brand would survive. The founder believed them — and they may even have meant them at the time.
But businesses change hands, strategies shift, the person who made the promise leaves. Verbal commitments evaporate. Provisions in the sale agreement do not.
If something matters to you — the name on the door, your charity commitments continuing, key employees being retained for a defined period, the office not being closed — write it into the documents. A good buyer will agree. A buyer who refuses is telling you something important.
"I underestimated what life after the business would feel like"
For thirty years, the business was the structure of your week, your identity, your social life, your purpose. Then one day it is not.
Many founders sell with a vague plan to "spend more time with family", travel, sit on boards. The first six months feel like a holiday. The next eighteen months can be harder than anything they experienced as a founder.
The owners who navigate this best tend to have planned the next chapter before closing, not after. Sometimes that is a new venture. Sometimes a serious philanthropic commitment. Sometimes board work with real responsibility. The specific answer matters less than the fact of having one before the keys change hands.
What we have learned from listening
We do not pretend a sale is a small decision. It is one of the largest most founders will ever make. The owners who look back on it with satisfaction — even years later — almost all share three things: they started preparing early, they chose a buyer whose incentives matched their hopes, and they had a life ready to walk into on the other side.
We mention this not because it sells anything. We mention it because most of the founders we meet are at the start of that process, and these are the lessons they tell us they wish they had heard earlier.