It's been a bit over a year since we started winding down my startup, Simpo. While we eventually sold the assets and found a soft landing for some of our employees, I have no interest in framing this as a success story for the sake of optics. Objectively, Simpo failed.
I think that it would be much more useful to write about the mistakes I've made and the subsequent lessons learned. My hope is that by speaking openly, other founders who may experience something similar realize that they are not alone, and perhaps even manage to sidestep some of my errors.
The process of starting, growing, winding down, and eventually selling Simpo was hands-down the most difficult thing I've done in my career, and perhaps in my life.
I've made loads of mistakes throughout the process. While many of them deserve their own posts, today I'd like to focus on what I consider to be the single biggest mistake I made as a founder: starting a company for the wrong primary reason.
The main reason I started Simpo was to prove to the world, and thereby to myself, that I was enough - that I was worthy of love and acceptance.
"...if we got it wrong and the company tanked, it would mean that I wasn't enough."
I didn't do this fully consciously, but the net effect was the same: from the first day at Simpo to the last, every single decision, problem, and event felt extremely personal and extremely high stakes - if we got it wrong and the company tanked, it would mean that I wasn't enough.
It made work way more difficult and anxiety-provoking than it should have been - not only for me, but for my whole team.
Origins
In hindsight, I can trace the origin of the connection between success and my self-worth to my early childhood:
Back in the mid-90s, as a kid in elementary school, I felt like a total outsider. I tried hard to fit in, but despite my attempts, had almost no real friends. I was often ostracized and left out. Moreover, it was a violent environment, and I experienced traumatizing physical and emotional bullying that carried on into middle school.
My one escape was computers: I had become interested in them at an early age and wrote my first line of code by age 8 or 9.
When things got bad at school, I would get back home and dive into coding. Over time, this escape has developed into a coping mechanism. It sounded like this:
"I might not have friends, but at least I'm good at coding. One day I'll be rich and famous and all those kids who rejected me will see how wrong they were."
The goal of being "rich and famous" eventually morphed into "being a billionaire CEO with a wildly successful tech company." A high bar! But one that I felt I had to pass to prove to the world that I was "good enough."
Having something to prove
I carried this mistaken notion with me as I started Simpo. I ended up raising millions of dollars, hiring a team, devoting every single ounce of my energy to the company, and needlessly losing sleep over many decisions that weren't actually that important. I was constantly trying to mitigate failure because of how catastrophic I perceived its implications on my worth to be.
This continued for over 5 years.
And then something happened that I did not let myself believe ever could: Simpo failed.
In a big way, I am deeply grateful that it did. Had it gone on to become a major success, it would have been much more difficult for me to disconnect my self-worth from external successes, to recognize how unhealthy it was to rely on such validation, and to begin healing from it.
After shaking off the initial temptation to jump into something new right away, I ended up taking some time for myself. I started writing, working out, and thinking about what I really wanted out of my life.
Over a year has gone by since we shut things down - a year full of introspection and self-work.
"What I wanted above all else was to feel loved and accepted - by my own self." With therapy, and with the help of my coach, I discovered just how much there was to unpack. I began to understand that what I was really primarily seeking wasn't external success or the money and status that came with it. What I wanted above all else was to feel loved and accepted - first and foremost by my own self.
This is very much work in progress, and my internal sense of love and acceptance and of "being enough" ebbs and flows daily.
But the recognition that my sense of self-worth should come from within is constant. It should not come from building a successful startup, or for that matter, from any external circumstances or the attainment of goals.
All of that said, I may yet start another startup. But if I do, it won't be to prove to anyone that I am inherently worthy. It would be because I'm excited to solve some problem in a better way.
If any of this feels familiar
I am reluctant to give out advice. By no means am I an expert, and everybody's situation is different. But if you're a founder and this feels familiar, I would at least say this:
There isn't anything wrong with having something to prove. In fact, when things get tough, it might just be what gets you out of bed. But what you set out to prove if you start a company should not be your self-worth. Therapy, coaching, and meditation are all better paths to resolving that particular issue.
If I could go back in time, that's what I would tell my 26-year old self. For the record, I wouldn't discourage him from starting a company, I would just advise him to do it for different reasons.
If you're setting out to create a startup to prove something, let that something be that you can solve a problem in a better way, or that something that isn't necessarily obvious to others is actually a good idea.
Don't start a company to prove that you're worthy of love.
You already are