What selling the first company taught me, and what it did not

OneWho is telling this?

I run a manufacturer in Portugal: sixty people, family-owned, and I am not the family. Before this I founded and ran a logistics software company for eleven years and sold it at ninety-four people.

This is a postmortem rather than a decision story. The decision to sell was slow and boring and mostly made by circumstances. What is worth writing down is the eighteen months afterwards and the seventh month of the job after that.

TwoWhat actually ended, and why?

The company did not fail. It was bought by a strategic acquirer at a price I was content with, closed in fourteen months from first approach, with a twenty-four-month earn-out I completed.

What ended was my reason for getting up. I had spent eleven years with one question (does this work, will this survive), and the sale answered it. I had not appreciated how much of me was the asking.

The earn-out is the part nobody describes accurately. For two years I was the CEO of something that was no longer mine, reporting to people who were polite, with a team who correctly understood that I was leaving. It is not a job. It is a supervised handover that pays well and slowly removes every reason you had to do the work.

ThreeWho did you talk to during it?

Lawyers, constantly. My wife, who bore the whole thing. Three other founders who had sold, all of whom told me the same untrue thing: that the first six months afterwards are wonderful.

Nobody who had sold and then gone back to work told me what that transition was like, because the people who tell you about selling are people who are still selling the story of having sold.

I did not talk to anyone at all in months four through nine of the break. That was the real cost and I did not identify it as a cost at the time; I described it to myself as rest.

FourWhat did the money change?

Less than I expected and in the wrong direction. It removed the fear, which I had assumed was the problem, and it turned out the fear had been doing a lot of load-bearing work.

It changed my relationships with three friends, all of whom I am still in touch with and none of whom I speak to the same way. It did not change my marriage, which I attribute to luck rather than character.

The money answered a question I had been asking for eleven years. It turned out to be the wrong question, and I had built a personality around asking it. Eighteen months is how long it took to find a different one, and I only found it by going back to work.

The money answered a question I had been asking for eleven years. It turned out to be the wrong question, and I had built a personality around asking it.

FiveWhat happened in month seven of the new job?

I tried to fire the operations director and the family who own the company said no.

In my first company that conversation would have taken four minutes. Here it took four months, and at the end of it the operations director, who had been there nineteen years and who I had judged in about six weeks, was still in post and substantially better, because the chairman had insisted we actually find out why he was underperforming rather than concluding he was the wrong person.

He was not underperforming. He was doing two jobs because a role beneath him had been vacant for a year, and I had read the output and diagnosed the man.

SixWhat did it cost?

Eighteen months of my working life, which I would take again. Somewhere around four months of the new company's momentum, which I regret.

It cost me most of my credibility with the operations director for a year, and I have not fully recovered it. He knows what I tried to do. He has never mentioned it once, which is worse.

The number that surprised me was seven: the months it took me to repeat the exact habit that had worked for eleven years and was wrong here. I had expected the transferable things to transfer and the non-transferable things to announce themselves. They do the opposite. The dangerous habits are the ones that were rewarded.

SevenWas it the right call?

Selling: yes, and I would not change the price or the timing. The earn-out: no. I would have taken meaningfully less money for a six-month handover instead of twenty-four.

The eighteen months off: right in length, wrong in shape. I should have had one standing commitment: a board seat, a teaching slot, one group that met monthly, anything with a date in it. Unstructured rest after eleven structured years is not rest, it is drift with a good explanation.

Going back to being a CEO rather than an investor: yes, unambiguously, and it is the decision I am least able to justify. I like the work. That turns out to be sufficient, and it took me eighteen months to accept a reason that simple.

Still unclear: whether I am any good at running a company I did not build. Ask me in four years.

EightWhat does the next CEO need to hear?

Negotiate the earn-out like it is the job, because it is. Everyone spends their energy on the headline number, which is decided in a week, and signs away two years in a clause discussed on a Thursday afternoon.

Put one dated commitment in the calendar before you finish. Not a plan. A date, with other people in it. The gap is not a holiday and it does not fill itself.

Your best habits are the dangerous ones. In a new company, the instincts that got rewarded for a decade will fire fastest and fit worst. Mine was speed on people decisions, which had been a genuine strength and was, in a nineteen-year business with no bench, close to vandalism.

The thing everyone says that turned out to be false: 'the second one is easier.' The building is easier. The being is not. Nobody at the new company cares that you did it before, and they are right not to.