Fifteen years in tech, two seasons in the right seat of a Subaru, and one mountain town later.
One person, several seats. The operator who runs the company. The co-pilot who reads the road. The founder who built the next thing. The local who rides the lift line. The builder who keeps shipping. Read top to bottom, or skip to whichever chapter you needed.
Fifteen years in tech and the lesson is always the same: the unglamorous middle layer is where companies live or die. Networks, identity, security, uptime. Backups that actually restore. Alerts that fire before the customer notices. The kind of work nobody photographs.
As CEO of a small California managed IT firm, I sit in three chairs on a busy day — operator, finance, and the person handling whatever broke at 4 AM. I'm joined by a co-founder who runs deep on the technical side and a full-time engineer who keeps the floor swept. Small team, sharp blade.
What I learned running it is the through-line for everything else on this site: shipping is not the same as delivering, software is not the same as a working system, and the difference between an idea and an outcome is usually somebody who is willing to stay late.
A few principles I keep around because they refuse to age: ship the smallest thing that proves the point; instrument before you optimize; if a process exists only in someone's head, it doesn't exist. And the one I come back to most often — strategy decks are fine, but working software is better.
A short detour into the strangest job I've ever had: sitting next to a rally driver in a Subaru, reading the road two corners ahead of where they could see.
For a couple of seasons, the title on my hat said co-driver. The job is straightforward to describe and impossible to make easy: you sit on the passenger side of a 200-horsepower Subaru with a six-point harness, and you tell the driver — calmly, by your watch, regardless of the rocks coming at the windscreen — what the next thirty seconds of road are going to do.
The notes are a dialect: "Five right, opens, into long four left, crest, caution rocks on inside." You don't get to look up. You can't ask if the driver heard you. You can't second-guess the line. You read, you time, you communicate the next corner, and you trust the seat.
It rewires how you make decisions everywhere else. You stop arguing about which corner you should have taken three corners ago. You get good at delivering bad news quickly, with the right amount of detail. You learn to trust your instruments more than your stomach. And you accept that the driver is going to do what they're going to do — your job is to make sure they have the information when they need it, not when it's convenient.
I don't run stages anymore. But the seat is still in my head every time a customer asks a hard question, every time a system is on fire, every time a deadline is closer than the team thinks. Pace notes get you home.
OwnerSight is the company I'm building right now. It started with a problem I see walking around my own valley — a whole neighborhood of beautiful houses, almost none of them lived in.
Up here you can drive past a hundred million dollars of real estate on the way to the grocery store, and most of it sits empty ten months a year. The owners are in Dallas, Chicago, Atlanta. The cleaner shows up between bookings. The property manager handles arrivals. Nobody is paid to walk in on a quiet Wednesday in February and notice the heat is off in the guest wing.
OwnerSight is the third party watching, in three layers. A real person walks the property on a scheduled cadence — that's Eyes. Smart sensors watch for water, freezing, and entry 24/7 between visits — Sensors. And a local rep is on the ground to let the plumber in when something actually breaks — Hands. Most home-watch services stop at the first layer. Most monitoring companies stop at the second. We do all three.
The math is blunt. A burst pipe in a watched house is around two grand. The same pipe in an empty one, six weeks of flooding before anyone notices — twenty. And many insurance policies quietly reduce or cancel coverage on homes that sit empty more than thirty days unless someone is documenting visits. We document everything.
Every install ships with a redundant Starlink uplink — deployed by HighCountryConnect, the other company I'm involved in up here that handles connectivity for places the grid doesn't quite reach. Storms knock out power right when empty homes are most at risk; that's exactly when the sensors have to keep talking.
One person walking the property. Smart sensors watching the rest of the time. A local rep on the ground when something breaks. Built for second-home owners with a lot at stake and a long way away.
I live at the foot of Beaver Creek. On a clear winter morning the lift line is fifteen minutes from my coffee. That is not a small input on a person's life.
I am not a professional snowboarder. I am, like a lot of the locals up here, a person who chose to live close to the hill so that "I'm just going to run a few laps before lunch" becomes a legal weekday activity. There's a directness to mountain-town life that rubs off on everything else: people are blunt, weather is real, and you can't fake your way through a black diamond at the end of the day when your legs are gone.
OwnerSight exists, in part, because I'm here. The valley is full of houses sitting empty ten months of the year — owned by people in Dallas, Chicago, Atlanta — and watched over by property managers whose incentives don't quite line up with the owner's. Once you see that gap, you can't un-see it.
The work I'm most interested in right now isn't the demo-on-a-stage kind. It's the kind that survives contact with real users, and saves them twenty minutes a day, every day, forever.
A lot of AI work right now is theater. A demo runs in a controlled environment, gets a standing ovation, and quietly falls apart in week two when a real user does something unexpected. I have less and less patience for that. Either it survives the user or it doesn't.
What I'm building now: agents that handle real workflows for real teams, AI-assisted reporting that improves the longer it runs, and the kind of internal tooling that lets a small business punch three weight classes above its size. OwnerSight uses some of this work directly — the inspector reports are scored by AI before a human sees them, which is the only reason a small network of contractors can deliver consistent quality at scale.
If you've got a workflow stuck on a person's calendar, a pile of data you can't unlock, or a piece of software that everyone hates but no one has time to fix — there's a good chance I can help. Open a channel.
Project, idea, or just curious about a corner of any of the above? I read every message. Most replies go out within 24 hours.