What I Was Surprised to Lose When I Sold My Company

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I showed up at the office on a Saturday morning to grab something I had left in the supply closet.

The building was empty.

A few weeks earlier, we had sold the company to a large acquirer in Australia. It was a sale I had been working toward for years. I had imagined the relief I might feel when it was done. The money would be in the bank. The uncertainty would be over. After years of carrying the company, I would finally have some flexibility.

What I had not imagined was the grief.

As I walked through the empty office that morning, it swept through my body. Something about being there alone made the loss inside the change suddenly real.

It would not be long before this team would no longer be my team. This building would no longer be my home away from home. The rooms where we had argued, celebrated, struggled, and tried again would belong to someone else.

Even as I write this now, I can feel something surge in my chest.

In hindsight, I can see that part of the reason I built the company was to find my own place of belonging.

I wanted a corner of the world where I would not have to keep navigating changing jobs and rooms full of strangers. I wanted to make things among people I cared about. I wanted a tribe.

I did not understand that clearly at the time.

I thought I was building a product. Then I thought I was building a business. As the company grew, I learned to think about market share, shareholder value, and the eventual possibility of an exit.

But somewhere along the way, the company also became a place where a group of people found one another.

This is one of the strange things about building a startup.

We often begin with the hope that one day we will sell it. Founders and CEOs fantasize about the moment when we will no longer be needed, when the money will be in the bank and our time will once again belong to us.

And then, sometimes, we get what we wanted.

Only then do we understand more clearly what we are losing.

When soldiers are interviewed about why they keep fighting, a common answer is that they are fighting less for the country or even the mission than for the person on their left and their right.

Startups can become like this too.

Somewhere along the way, the work became less about the outcome and more about the people beside me. It became about the tribe we were creating, the memories we were building, and the friendships growing in the middle of a professional experience none of us would ever quite be able to explain to anyone who had not been there.

We had survived things together.

We had watched ideas fail and people leave. We had raised money and nearly run out of it. We had celebrated launches and mourned versions of the company we had once believed in. We had spent years trying to make something real together.

I wish I had understood sooner how much that mattered.

I spent much of my time as a CEO thinking about how to motivate the team, strengthen the culture, and build greater resilience. I searched for the right values, rituals, goals, and ways of working.

Those things mattered.

But I think I sometimes missed the simpler truth beneath them.

People are more resilient when they feel that they belong. They can carry more when they are carrying it alongside people who know them. The work becomes more meaningful when the people to their left and right are not merely colleagues, but people with whom they are sharing a chapter of their lives.

I missed some of that because I was always looking ahead.

I was waiting for the next fundraise, the next milestone, the next version of the product, the next moment when the company might finally feel safe. I believed the destination would justify the difficulty of the journey.

Standing alone in the office that Saturday morning, I wondered whether I had it backward.

The journey had not merely been the price of building the company.

The journey was the company.

The years beside those people were not something to endure on the way to the outcome. They were the thing I would miss when the outcome finally arrived.

A company is, in the end, a group of people choosing to build something together.

That may be the whole thing.

I spent years believing the product was what we were building.

Walking through that empty office, I realized the thing I would miss most was not the product, the company, or even the role.

It was the people.

And maybe that was what I had been building all along.

—Matt

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