Should I Start Another Business After Selling One? Why I Might Not

If you are asking should I start a business again after an exit, or what to do after selling a business, this is the part people skip, recovery, identity, and space to become yourself again.

TLDR, what I learned after selling a business

• After selling a business, the urge to start again can be identity, not truth
• A venture backed startup can crush curiosity and drive over time
• The first job after an exit is often rest, freedom, and space
• If new ideas trigger fatigue or despair, listen to that signal
• You can start again later, but starting from obligation can be emotionally dangerous

A therapist story that reframed everything

Last week, my therapist and I were talking about the challenges of parenting. She told me a story that was intended to be illustrative for a challenge I’m facing on the parenting front, but it ended up being incredibly illustrative for me personally.

She told me about an experiment run in an English school. The school was designed to be an alternative school for ‘troubled’ kids, kids that were failing to succeed in mainstream schools. What was special about this school was how little the schoolmaster changed from a normal school. He made one major adjustment. There were no rules, save one: you use not impede on the space or rights of another student. Aside from that, students were left to their own devices.

They could go to class when and if they liked. Roam the hallways. Hang out in the library or on the playground. Whatever struck their fancy.

The crazy and almost unbelievable outcome is within six months nearly every student was regularly attending class and excelling academically. These seemingly troubled students were crushing school.

So what made the difference? Ostensibly, at least according to my therapist, children struggle when rules and order are imposed on them. Their natural curiosity and drive is squashed out. The route back to their natural tendencies is one of space, freedom, and time.

Why I cried after that story

As my therapist finished the illustrative story, I found tears welling up in my eyes. Not tears on behalf of my son (who largely is doing just great), but tears for myself. I realized 7 years running a venture-backed startup had crushed the curiosity and drive out of me. But the tears weren’t about the loss.

The tears were tears of hope that what I’d lost might return. The story connected me with a framing that helped to cast light on the truths that much of what I’ve been experiencing around fatigue and burnout is normal and that there is a well-worn path back to my natural state. And the path that’s needed is one of freedom, space, and most likely rest.

 If you have sold a business and you are wondering what to do next, this is the first signal to take seriously, your body may be telling you it needs recovery before reinvention.

What happened when I tried to start again after selling

We sold Twenty20 in April of this year. By July, I found myself beginning to tinker with new business ideas. For years, I’ve kept a backlog of all the ideas that came up over the course of my time founding and running my company and I felt excited, or so I thought, to have time and space to begin exploring those ideas. However, whenever I sat down for a half a day to dive in, I found myself hitting an emotional wall. I’d get excited for a few hours, dive into the early exploration and validation process, then find myself overwhelmed with fatigue, depression, or despair.

 What it looked like in my body

• Excitement for a few hours
• Then a sudden wall
• Fatigue, depression, despair

A week ago, during dinner with a close friend and a conversation about this experience, I came to a realization that I needed to let go of the idea that I would start another company.

Should I start a business again, identity versus aliveness

For more than a decade now, my identity has been in large part one of ‘founder,’ ‘entrepreneur,’ and ‘CEO.’ Even as I approached the sale of the company, I found myself talking with friends about what I might do next, what I would start. After all, I was an entrepreneur. Starting companies is what we do. But as I’ve begun to look into the abyss of what might be next, I am realizing there is no way to find my way to a real answer of the work that is mine to do without casting off this identity and these assumptions.

I might start another company. I might start 10 more companies. That’s not the point. The point is that jumping to starting another company out of a sense of identity, obligation, or a need to prove that I can feels life-threatening. Maybe not in the physical sense, although perhaps that also, but definitely in the emotional sense.

What to do after selling a business, a simple 30 day reset

 If you are between chapters, here is a simple plan that matches what I needed.

• Protect sleep, your nervous system needs it
• Remove optional commitments for 30 days
• Spend time in freedom, walks, reading, play
• Talk to friends without turning it into a plan
• Notice what brings curiosity back, then follow that thread

Letting go of the founder identity

So during that dinner, I decided to announce to my friend, and more importantly to myself, that I was going to let go of the belief that I will start another company. I’ve realized since, I must also let go of my identity as entrepreneur, CEO, or founder.

For now, to find my way, to remember my heart and my true identity, I must be simply Matt.

The beginning of freedom, becoming myself again

For me, that line in the sand, and the step I’ve taken past it into being simply me, is the beginning of my time of freedom in this new school for troubled and recovering students. I need to be here, to rediscover what it is that makes me me. To rediscover the innate parts of me that are curious, driven, and creative. To remember that before I raised money, hired a team, went through the countless struggles to build a company that supported thousands of customers around the world, before I ran face-first into burnout and exhaustion, before we found a safe and wonderful place for our product and team to carry on beyond my tenure, before all that, I was a curious kid who liked playing with computers. Liked reading about new things. Liked thinking with friends about what might exist in the world that doesn’t yet.

 And maybe that is the real answer to should I start a business, not yet, not until it comes from that place again.

So here I sit.

Just Matt.