Nobody loves a parking enforcement company (and why I bought one anyway)

Tell someone you run a hat brand and they smile. Tell them you run a parking enforcement company and they tell you a story about the worst ticket they ever got. I’ve heard hundreds of these stories. I keep a mental top ten.

Here’s the thing though: every one of those stories has a second character nobody mentions — the person who couldn’t park at their own building that day.

The customer isn’t who you think

TG’s customers aren’t drivers. They’re property owners and tenants — the dental office whose patients circle the block, the apartment resident who pays for a spot someone else is sleeping in. Enforcement is a service to people who follow the rules, funded by people who don’t. Once you see it that way, the business stops feeling adversarial and starts feeling almost boringly fair.

Unglamorous is a moat

Nobody dreams of starting a parking company, which is exactly why it was available. The businesses everyone wants to start are crowded. The ones that make people wrinkle their nose have room to breathe, steady demand, and customers who are relieved you exist.

If you’re hunting for a business idea, make a list of things people complain about but nobody wants to run. Somewhere on that list is your margin.

Rules are a kindness

The lot with no enforcement isn’t free — it’s just allocated to whoever is most shameless. Clear signs, consistent enforcement, no exceptions: that’s not hostility, that’s legibility. People relax when the rules are real.

I think about that more than I expected to, in all three of my jobs.