← Jacob’s writing
May 19, 2026 · Personal

The exit nobody warns you about

Most founders chase the exit. What you gain is obvious. What you lose, nobody warns you about.

Founders rarely start companies just to sell them. But if they want what they built to survive and scale, an exit often becomes part of the story.

I was at an MIT VMS event recently where someone mentioned that one of the most common things the community counsels founders on isn't fundraising or product strategy. It's what happens after the company is sold.

That stuck with me. Because despite how common it apparently is, nobody really prepares you for it.

It feels taboo. You've "won." Maybe you've created wealth for yourself and your family. Who are you to feel anything other than gratitude?

But here's the truth: when the exit finally comes, you're not just handing over a business. You're handing over a piece of yourself.

The excitement is real when the deal closes. But after that fades, something else often shows up:

A loss of purpose.
A loss of routine.

A loss of relationships.

A loss of identity.

This is because, it's hard for your company not to become you.

The nights. The weekends. The lack of other hobbies. The years of uncertainty. The investor no's. The near-death moments. The loneliness. The constant pressure of carrying something nobody else fully understands. The first question I heard at every gathering was, "How's Perch doing?"

You go to sleep thinking about it. You wake up thinking about it. Over time, the company stops being something you work on. It becomes part of your identity.

Talking with other post-exit founders, I keep hearing the same thing reflected back. The thing that gave structure and meaning to their lives suddenly disappears.

You think you've reached the peak of a mountain. In reality, you've reached a cliff. The path you were on simply ends. And now you have to face some of life's hardest questions: Who am I? And what do I do now?

So if you're building toward an exit, don't just spend time building the company. Spend time understanding what you actually love about the journey, and building a life, identity, and sense of purpose that can survive beyond it. Because one day, the company may be gone. And you'll still have to figure out who you are without it.