Most founders fall in love with the idea they’re most excited about. The better question is which idea customers are already paying for. In my case, those were two very different things, and it took a failure to show me which one mattered.
I recently spoke with Tyn Magazine about how my company started as a side service I almost didn’t take seriously.
Early on, my attention was on a different venture entirely. On the side, I started offering software development services. I hired a small team, took the project manager role myself, and earned roughly a 20% margin on the work. It brought in revenue and kept people busy, but it wasn’t where my ambitions were pointed. Then the main venture failed, and that side service is what kept me afloat.
That’s the part I think most founders overlook. A service that keeps clients coming back while you’re barely paying attention has already been tested in the toughest conditions. That’s stronger proof than a pitch deck or a waitlist. In the article, we talk through the three signals I’d look for: repeat clients, a margin that survives paying other people, and a service someone else can deliver to the same standard.
The team mattered as much as the clients. As I told Tyn, “We build teams like we build products: custom, lean, and aligned with the business model.” Hiring specialists early and stepping into a coordinating role, rather than doing everything myself, is what turned side income into something repeatable.
That service eventually became Alive DevOps and the base I used to launch two more companies, all without outside investment. Within a few years, the businesses moved from six-figure revenue to seven figures.
Looking back, what surprises me most is how little of it came from a perfect plan. Like a lot of what I learned in competitive golf, it came from reading which shot actually had momentum and committing once the evidence was clear.
The article also opens with a number that stopped me. According to QuickBooks, 47% of Americans earned side income last year, but only 20% registered it as a business. Some of those people are sitting on a real company and don’t know it yet.
If you’ve got side work that keeps quietly paying off, it’s worth a read. Read the full article on Tyn Magazine. Sometimes the business you’re waiting to build is the one already paying you.
