I Started Four Companies. The Best One Was an Accident.
I've started four companies and sold three of them.
The one I never plan to sell is the one I never meant to start.
People assume founders run on some grand plan. A vision on a whiteboard, a five-year roadmap, a clean line from idea to exit. My career has looked nothing like that. It's been more like a series of accidents I got lucky enough to pay attention to.
So here's the honest version.
The first one taught me how NOT to do things
I was a 22-year-old college dropout trying to build software for car dealerships, an industry I barely understood. That company was VinSolutions, and it became the number one CRM in automotive.
We bootstrapped it. No outside funding, all the way through the 2008-09 recession, to $35 million in annual revenue. It sold for $147 million in 2011.
That sounds like a victory lap. It wasn't, really.
What I mostly learned from that first exit was how not to do things. Be careful taking anything but cash in a deal. Be careful what you wish for. Some days I wish we'd never sold it, because I think it would be a unicorn by now.
A big exit doesn't fix you. It just hands you a new set of problems and a little more money to make them with.
The offshore thing I swore I'd never do
My second company was Stackify. We built monitoring and logging tools to help developers find and fix bugs in production.
For years I avoided offshore developers. I'd heard nothing but horror stories from other founders: language barriers, late-night calls, code you had to rewrite anyway. Everyone seemed to know someone who'd tried it and hated it.
Then I did it by accident.
We needed Java developers to build our Linux support and couldn't find any in Kansas City. A friend who ran a dev agency said he had some. We trusted him, didn't even interview them. First phone call, I find out they're in St. Petersburg, Russia. (This was 2012, long before the Ukraine conflict. I wouldn't hire in Russia today.)
They were excellent. We worked with them for two years.
So I tried it again on purpose. A firm in Uruguay. Also great. Then the Philippines, where the talent was strong, the English was excellent, and honestly they were some of the nicest people I'd ever worked with.
Three for three. After years of swearing I'd never touch offshore development, I'd quietly become a believer.
An accidental business was born
In 2018, my friend and I set up a small team in the Philippines for Stackify. That team grew to more than 20 developers and ended up being a big part of why Stackify worked, and why we eventually exited in 2021.
Here's the lucky part. When we set that team up, we set it up as its own company.
It worked so well that all my friends and connections started asking if they could get access to the same talent. We hired 100 developers in the first year just to keep up.
That accidental side business turned into Full Scale.
Today it has more than 300 engineers helping companies build and scale their teams. I didn't pitch it. I didn't raise for it. I solved my own problem, other founders had the exact same problem, and a company fell out of the side of that.
I've sold VinSolutions, Stackify, and one other company. Full Scale is the one I'm not selling.
What four companies actually taught me
If you want the unglamorous lessons, here are the ones I'd actually stand behind.
Building is the easy part. Selling is the hard part. Engineers like me fall in love with building things. But "if you build it, they will come" is not a real thing. Writing the code is maybe ten times easier than figuring out how to get anyone to care about it. I had to learn that the slow way.
You'll never be the best, so aim to be the best known. It is far more important to be best known for what you do than to be best at it. That's why I write, post, and put my opinions out there even when they're half-formed.
The real money is in the niches. When you sell to everybody, you sell to nobody. VinSolutions worked because I picked one industry and went deep, not wide.
The hardest moment is realizing you're the bottleneck. At some point the founder becomes the reason the company stops growing. Seeing that honestly, and letting go of the work other people should be doing, is harder than any technical problem I've ever solved.
None of that showed up on a roadmap. It showed up in the mess.
Why I write about it now
For most of my career I just put my head down and built. These days I spend a lot of time sharing what I got wrong, because I wish someone had told me earlier.
I write a weekly newsletter called Product Driven for founders and engineering leaders. It's where I work through the stuff nobody warns you about: hiring, scaling teams, when to build versus buy, what a real exit actually feels like. I also host a podcast called Startup Hustle, where I talk to other founders and CTOs about the same things.
It's not a highlight reel. It's mostly the mistakes, told straight, so maybe you make new ones instead of mine.
That's the whole reason I keep showing up.
I still don't have a grand plan. I just pay closer attention to the accidents now.
Matt Watson is a four-time founder and CTO with 20+ years in software. He co-founded VinSolutions (acquired for ~$150M), founded Stackify, and is CEO of Full Scale, which helps companies build software teams with developers in the Philippines. He writes the Product Driven newsletter and hosts the Startup Hustle podcast.