Ten Years Gone: What Owning a Company Taught Me
Just over a decade ago, I walked away from the company I helped start. I didn’t know it at the time, but I was already burned out, broken, and drifting away from the person I wanted to be. It’s taken time, space, and a lot of reflection to understand what happened — and what I’ve learned.
Starting From Chaos
In 1997, at the age of 21, my coworkers and I found ourselves caught in the crossfire of a corporate power struggle. The company we worked for was imploding from the top down. We liked working together, though — so we left. We spun off and started doing the same kind of work as a new company, initially still serving our former employer.
That relationship didn’t last. Eventually, we were competing directly.
The early years were brutal. Long hours, little money, endless uncertainty. But we believed in what we were building, and eventually, it started to click. For the next five years, the company grew rapidly — 20% year-over-year, sometimes more.
We felt unstoppable.
Then the cracks started showing.
Three of our six original partners separated. (And yes — six founders. At 21, that seemed reasonable. It wasn’t.) Somehow, we pulled through. We landed a major client, three times the size of our next biggest. It should have been a turning point.
It was.
But not the one we hoped for.
When Values Slip
We started making decisions based on money instead of merit. We cut corners. We let marketing dictate strategy. We bid on projects we had no business touching. Technical standards — the ones we swore to uphold — were quietly sidelined. One client got their own version of the code. Then another. Soon we were living the exact nightmare we’d once escaped: fragmented systems, mounting technical debt, and a culture that prioritized sales over substance.
We stopped building the company we set out to create — and started constructing something else entirely.
We made choices I wish we hadn’t, and problems we created still linger. They may always be haunted by them.
The Breaking Point
By 2015, I was hollowed out. I wasn’t just tired of the work — I didn’t like the person I had become. The final straw came during a demo we shouldn’t have taken, presenting a project we shouldn’t have bid on. One too many questions from “that person” — the one trying to play gotcha and prove they’re the smartest in the room — and I snapped. I said something cutting enough that three years later, they were still complaining about it to my former coworkers.
I don’t regret what I said. They had it coming.
But I do regret what it revealed about me. I had nothing left. I wasn’t showing up as a leader, a partner, or even a decent human being.
So I left.
Life After
Since then, I’ve worked in places I never expected. I led development on a massively multiplayer online game. I built a web application firewall for a global hosting company. I’ve helped develop software for Fortune 50 companies in industries ranging from banking to manufacturing to insurance.
Today, I work at a company that builds applications for nonprofits and community foundations. I manage a team focused on CRM and accounting systems. And most days, I enjoy it — not just because the work is meaningful, but because I see how much helping others help others matters to me.
I didn’t know I needed that. Now I do.
Lessons I Had to Learn the Hard Way
Working Harder Isn’t Always Enough
You can’t fix a broken system by working harder. There’s a small circle of things you control, and a vast world outside that circle. I tried to change things outside my reach — people, partnerships, priorities, values. It didn’t matter how hard I worked. Some things were just broken. Some people didn’t want to change.
Your People Deserve Better
If someone shows up and truly cares — about the product, the process, the company — take care of them. Give them raises. Time off. Recognition that actually means something. The worst thing you can do to a great employee is reward their hard work with… more hard work.
And if you’re reaping rewards while they’re stuck with old equipment, no raises, and long hours — don’t be surprised when they check out or walk out.
Your team owes you nothing beyond the hours they’re paid for. Anything extra has to be earned. You’re the person who has to put in that work.
Boundaries Matter
“Work family” isn’t family. They’re coworkers. Maybe even friends. But the second you blur that line, you open the door to manipulation — or worse, self-delusion. Meanwhile, the people who are your real family watch you disappear into late nights, missed events, and creeping emotional distance.
Entrepreneurship doesn’t just ask something of you. It takes something from everyone close to you. And if you don’t see that, you’ll lose more than your company.
Don’t Chase Money
Money can make you stupid. I’ve watched smart people compromise core values for short-term gains that turned into long-term nightmares. We did it too. We took on big clients who demanded custom code, then scrambled to rebuild what we had broken.
In hindsight, the most expensive thing we ever bought was the illusion of fast growth.
Build Systems, Not Stress
Throwing bodies at a problem is a short-term fix. Building tools and processes is what buys you freedom. We could have done more with less — and saved our sanity — if we’d prioritized solving our own internal problems the way we solved client ones.
Success Is a Revealer
Adversity brings people together. But success? That’s when true colors come out. I saw partners change. I changed too. If someone’s values shift with their paycheck, pay attention. Get away from those people on your own terms — before they drag you with them.
What I Learned About Myself
I wasn’t as good a developer as I thought — mostly because I wasn’t challenged enough. Being the best programmer in a small company doesn’t help you grow. Working with smarter people did. I still have blind spots. I tend to gravitate toward dying technologies. But I’m working on that.
I also learned that I can be a good leader — if I’m not being micromanaged, and I have peers and leaders who believe in me. I do my best work in collaborative, supportive teams.
Most of all, I learned that confidence doesn’t mean arrogance. Over the years, I learned to hold my own in rooms full of executives, to speak honestly, and to stand my ground — even when I knew it might not be welcome. That’s a skill I wouldn’t have had without everything that came before.
And on the personal side…
Entrepreneurship is lonely. But it doesn’t have to be isolating. Let people in. Let them help. Your family is on the ride whether they signed up or not. Don’t disappear into your business and expect home to stay whole without you. Be present. Be kind to your partner. Apologize when you fail at that.
And when you can’t sort it out yourself — find a therapist. It’s not weakness. It’s wisdom.
Ten Years Later
It took leaving to understand what went wrong — and more importantly, what really mattered. I still carry guilt, but I also carry growth. I made mistakes I hope others won’t have to repeat. I left behind a company, but not the lessons it gave me. A decade later, I’m still building — not businesses, maybe, but better habits, better teams, and a better version of myself.