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.

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. 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. 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. For twenty-seven years I had been the man with the answers. That afternoon I couldn't answer a single question, including the one I wanted most: what if twenty-seven years ends like this? 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-five 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. Under the bright halogen lights, beads of sweat dripping from my forehead, I could almost feel my heartbeat. 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, 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

People imagine selling a company ends with the signature. It doesn't. By the time I walked into my lawyer's office, in the fall of 2017, the negotiations were over, the lawyers had spent months turning commas into billable hours, and the decision had been made months earlier on a beach in Florida.

And yet.

I remember the elevator. Why I remember an elevator ride after almost a decade, I couldn't tell you. But I do. As the doors closed, one thought kept circling in my head: I'm about to sign away my child. After twenty-seven years, every scare, every near miss, every victory, it didn't feel like paperwork. It felt like goodbye.

Then another thought arrived. It's not signed yet. I can still stop this. I can still walk back out of this building. Nobody has made me sign anything.

I imagine almost everyone who signs something life-changing has a moment like that. A marriage certificate. Divorce papers. The papers to sell a company. Adoption papers. Maybe even a will. There is always one final moment when the future still has two possible versions. The trouble is, there is no little voice telling you which one is right. No whisper saying, go ahead, you'll never regret this. Or, don't do it, you'll wish you'd turned around. You're left standing in an elevator with twenty-seven years behind you and two futures in front of you, trying to make peace with the fact that certainty isn't one of the documents waiting upstairs.

I walked in. I signed.

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.

People sometimes ask whether I knew, in that moment, that selling was the right decision. No. I hoped it was. Those are two very different things. Looking back, I believe it was one of the best decisions I ever made. But looking forward, standing in that elevator, I was just a man wondering whether he was about to make the biggest mistake of his life.

The Wire

The deal officially closed at five o'clock. I wasn't sitting in a boardroom. I was driving my seventeen-year-old daughter home from an appointment.

My phone rang. It was my lawyer. I answered and put him on speaker.

"Jeff," he said, "it's done." There was a pause. "The wire was sent to your account." And he said the number.

For a moment, I didn't say anything. Twenty-seven years. It had all been reduced to a sentence that lasted less than ten seconds.

Then another thought hit me. She heard that.

The ink on the documents wasn't even dry, and the conversation I'd imagined having with my children someday had suddenly arrived, completely uninvited. Not next year. Not after I'd thought carefully about what I wanted them to understand about money. Now.

I glanced over at my daughter. She looked back at me, waiting to see what came next.

In business, I had spent decades preparing for difficult conversations. With customers. Employees. Banks. Lawyers. I had rehearsed every important meeting of my career. I hadn't rehearsed this one.

How do you explain to a seventeen-year-old what just happened without letting the money become the story? Because it wasn't. The story wasn't the wire transfer. The story was everything that came before it. The years of wondering whether payroll would clear. The customers who said no. The loans. The mistakes. The fear. The persistence.

The money was simply the receipt.

Nothing further was said in that car. Strangely, we both pretended it hadn't happened. For her, it was probably eye-opening. For me it was, in its own way, traumatizing. Not in a scared way. In the way of being handed a conversation with my kids that I had not yet digested.

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.

One thing from that dinner stands out above the rest, and it happened the next day. One employee came up to me and gave me a big hug. She explained how much the funds would help her, not just with getting her out of a financial bind, but by letting her invest for the first time in her life. The feeling of finally getting ahead of her debts. As a working mother of two, that cheque made a difference. It made far more of a difference in her life than losing it made in mine. And it made me realize I could have that much of an impact on people's lives, some quiet, some thankful. That is what I remember most.

My controller was at that table too. Employee number four, hired in 1998. She stayed until the day the company sold, and one of the envelopes was hers. She is almost seventy now, and she is still my controller today.

The Last to Leave

On my final day in the office, at the end of December 2017, Dave came by. Employee number two, hired in 1994. When he started, neither of us was engaged. Neither of us had kids. We were both just young and energetic, and the company was small enough that the two of us were most of it.

We talked about the business. Where it started, what it had been through, the people who had come and gone. We reminisced. Twenty-three years of it, and now his future with the company and mine without it.

I was the last to leave that day, like always. It took me a while. I sat in my chair longer than I needed to, knowing it was the last time I would sit in it, the last time I would be the one to close shop. Then I closed it.