My wife Jamie and I bought our first rental property when I was 21 and she was 19. A three-unit in upstate New York — two tenants already in place and one unit that was a complete disaster. Which meant, of course, that's the one we moved into.
We'd used everything we had for the FHA loan. We had no idea how to be landlords. I grew up in construction so I could handle the remodel, but the landlord part? You learn fast when you have to.
Three years later we bought a two-family in a bigger city. I call it the house where we went to school to be landlords.
Non-paying tenants. Section 8 headaches. A drunk friend of a tenant who helped move a couch, slipped, and sued me for ten grand — and won. Then a lead paint issue on the eave of the house that shut us down for nearly two weeks.
After that one we went back to small towns.
Over the next 20 years we did land contracts, flips, full gut rehabs. I managed properties for friends for a while — got up to about 150 units at one point. Found out fast that managing other people's properties wasn't for me.
Then we bought a barn. Literally a barn.
We cleaned out the old milk house and converted it into a 3,300 square foot two-story home. Something everybody says they want to do.
I'll tell you this — it's something everybody always wants to do but I can tell you I'll never do it again lol.
We stayed there about 8 years. Currently living in our next project — split our home into a duplex, back half for Jamie and me, front half for my mother.
About six years ago I blew my back out. Had to step back from contracting and pivot to equipment repair — lighter work physically. That bought me some time but it wasn't a long-term answer either.
I started messing around with local AI models just to see what they could do. No real plan. One of them suggested building a landlord tool and I laughed at first — but I kept thinking about it over the next few days. So I looked at what was out there and didn't really see much except for large property management platforms built for people with a hundred units, not a handful.
I knew rentals. I knew nothing about building an app. So back to AI I went with the question "how do I build an app?" — and after months of very little sleep, juggling this and keeping the repair business going, here we are.
I'm proud of RentalGuards and what it's grown into. From a crazy idea to an app I genuinely think will help people.
It's free to download and I load a few credits on every new account so you can try it before you spend anything. If you like it, let me know. Hell, if you hate it — let me know that too.