The Year I Was Gone But Not Gone

In my first year in business, I cleaned the office toilets myself. Not as a gesture. There was no one else. Twenty-six years later, I ended the same company with a signature in a lawyer's office. This chapter is about the distance between those two rooms, and about the year it took to cross the last of it, which was the strangest and, in one afternoon I'll get to, the hardest year of my working life.

It started on a beach, with a decision that took six hours and felt, in the moment, easy. What nobody tells you is that easy and difficult are not opposites. Deciding to sell was easy. Being the man who had decided, for the year it took to actually do it, was the difficult part. Because from the day I called the M&A advisors to the day everyone found out, I was running a company I had already, privately, left.

The Performance

Nobody tells you how difficult the selling itself is. You are staring down your freedom, and to get to it you go back and forth with lawyers over clauses and minutiae, week after week, in secret, on top of the day job. The advisors sent a list of the information the buyers would need and it ran to 150 lines; I was overwhelmed just reading it. I've written separately about what that year costs in fees and taxes, for anyone standing at the start of it. This chapter is about the cost that never appears on any invoice.

Because here is the part that compounds everything: while you are selling the business, the business has to keep climbing. The buyer is watching, closely. Any hiccup in the numbers, and they can walk. A whiff of panic from the staff, and they panic. So you perform. The business was there, and succeeding. The captain wasn't. I had checked out months before anyone knew, and for a year I ran the meetings, gave the updates, watched the numbers, all of it already past tense on the inside, all of it under the eyes of a buyer looking for reasons to reprice or run. Keeping the sale confidential was manageable. Keeping the checkout confidential, performing a passion I no longer felt for people whose livelihoods depended on believing it, while an audience with a term sheet graded the performance, was the loneliest sustained act of my life.

Two months before the close, my director of sales resigned. He and I were on great terms; he had been offered an enormous opportunity at a Fortune 100 company, and I was genuinely glad for him. I also needed a new director of sales immediately, quietly, without the buyer reading it as a crack in the hull. We found one, fast, and two weeks later he was sitting beside me in meetings with the private equity buyers, and he did a fantastic job. On the outside: seamless succession. On the inside: two of the most nerve-shredding weeks of the whole year, and nobody in the building knew the stakes but me.

The Afternoon

Then, two weeks before the close, the network went down.

A major outage. Then, the next day, another one. Our customers were upset, understandably, and the phones rang off the hook. Clients wanting to know what was going on. Staff wanting to know what was going on. And I stood in the middle of it holding the one piece of information nobody else had: somewhere in the letter of intent, as I remember it, was a clause requiring us to disclose any material change to the business before close. Two outages in two days, two weeks out. I was going to have to tell the buyer, and I believed, in my bones that week, that they might walk. Twenty-seven years, one signature away, coming apart over forty-eight hours of infrastructure.

There is an irony in it I only saw later. In 1992, phones ringing off the hook saved my company. It was the sound of being rescued, the sound I would chase for thirty years. In 2017, two weeks from the finish, phones ringing off the hook was the sound of the whole thing possibly ending. Same sound. I have never heard it the same way since.

That afternoon I did something I had never done in 27 years of running the company. I left the office in the middle of the day, drove home, and cried. I sat on the bed and cried from the stress, the only time in my entire working life. My wife came home and found me lying there. She had stood in a parking lot in 1992 while I dismantled my own product, and now she stood in our bedroom while the sale of everything that had come after hung on a network switch and a disclosure clause. There was nothing to fix and nothing to say. Some afternoons the performance just runs out.

The outage was resolved. The deal held; the buyer did not walk. But I want that afternoon on the record, because every exit story, including the ones I used to tell, skips it. Somewhere between the beach and the wire, almost every seller has a day like that one. Nobody talks about it. I just did.

The Announcement

Everyone was in the room. Fifty people, most of whom had heard me give the ship speeches in that same spot: sailing together through rough seas, rowing in the same direction. My talk. My speeches. The vision I had stood in that very room, three years earlier, and asked them to believe in.

I was nervous in a way I hadn't been since the first State of the Union, and it was two dreads braided together: the announcement itself, and the open question of what came next for me. I made the announcement. And the room was shocked.

I know that face. I had seen it before, from the other side, as a kid, the day my parents sat us down and told us they were divorcing. The face that says: you're leaving us? And now the captain, of all people, was the one stepping off.

What they couldn't know was that the captain had stepped off months earlier. The hardest part of the announcement wasn't delivering the news. It was knowing the news was old.

People weren't happy, and I understood. Many congratulated me, and they meant it, and I stood there receiving congratulations for the thing I had just done to them. Because here is the plain arithmetic of that day, and I have never dressed it up successfully: the business was my child. I raised it for almost thirty years. I cleaned its toilets. And I gave up my child for a few bucks in my pocket. The few bucks happened to be a life-changing number, and it does not matter; against thirty years, every number is a few bucks. What I actually bought that day was my freedom. That was the real transaction. The company wasn't what I sold. It was what I paid.

And then the strangest feeling of the whole strange year: the moment the announcement was made, the room inverted. They were still on the inside, with the desks and the deadlines and each other and the Monday mornings. I was suddenly on the outside, looking in at the thing I had built, through glass I had installed myself. I had spent the year dreading that I was abandoning them. It took about an hour to understand that, of the two of us, I was the one who had just been left.

I've come to think this is true of almost every departure, not just mine. The person who leaves rehearses the leaving for months, grieves in advance, walks out the far side of it. The people who stay keep the rooms, the routines, and each other. Whoever announces the ending is rarely the one it strands. If you are planning an exit from anything, a company, a career, a city, a chapter, plan for this part: the world you're leaving will close behind you like water, and it will do it by Tuesday, and the strangest grief you'll carry is for a place that has already stopped missing you.

The Signature

The deal closed in a lawyer's office, in the fall of 2017. I would like to report that the pen trembled, that the room held its breath, that twenty-seven years announced themselves somehow in the moment. None of that happened. It was paperwork. Initials, signatures, more initials. The truth is that all the real endings had already happened by then: on the beach, in that room full of faces, on the bed that afternoon two weeks earlier. The signature was just the receipt.

The Envelopes

A few weeks after the sale closed, I took a dozen of my people out for dinner. The longest-serving, the ones who had rowed through the roughest of it. They thought it was a goodbye dinner, and it was.

At the end of it I handed each of them an envelope. Inside was money, real money; for some of them it was the equivalent of a year's salary. I hadn't announced it, and I didn't make a speech about it, because there was no speech. There had been no speech since the day in that room. I had spent a year unable to tell them the truth and one afternoon telling them the worst version of it, and an envelope was the only sentence I had left that I knew how to mean.

I won't pretend it settled the account. You cannot buy back a divorce face, and a year's salary is, by the arithmetic of this chapter, also a few bucks. But I will tell you the truth about that night, because it surprised me then and it instructs me now: handing over those envelopes was the single most rewarding thing the money ever did. Not the freedom. Not anything I bought. The leaving of it.