In 2019, my wife and I bought a 530-square-foot cabin outside Joshua Tree and welcomed our first guests two weeks later. We were not real estate investors. We were two people running an experiment.
Our friends Rich and Sara at The Joshua Tree House made it look possible. The Bluegrass Cabin was small, turnkey, and fairly priced: low enough risk that we could answer two questions at once. Did we actually like hosting, and could vacation homes work for us financially?
The first answer came fast. We loved it.
Some of that was the obvious pleasure of a good review. Most of it was something else. People save up for a trip, weigh a dozen options, and choose your house, often for a birthday, an anniversary, or a week they've needed for months. You build the container; they fill it with the memory. That mattered to us more than we expected.
The rest of it was a surprise, and it's the reason I'm writing.
I've spent just over 20 years doing digital product design, user experience design, for technology companies, as a hands-on designer and as a leader of teams up to 20 people. Software is temporary by design. You ship, you measure, you change it next quarter, and the thing you made a year ago no longer exists. A house is the opposite. It's a physical product built for permanence, meant to change slowly and deliberately. After two decades of designing things that dissolve, designing something that stays turned out to be deeply satisfying.
You build the container; they fill it with the memory.
The second experiment
In 2020, at the start of the pandemic, we sold our home in Berkeley and moved to Saint Helena. Another experiment: find out whether we liked living in the Napa Valley, knowing that if it didn't work, we could rent the house out long-term and move back to the Bay Area.
We liked it. We have three young kids in the local public schools, which are excellent. It's a beautiful town with a real economic mix, enough that we feel connected to people whose lives look nothing like ours. We've since moved into a house we rent and hope to buy someday, and put that first Saint Helena home into the long-term rental market here.
The third experiment, and the flood
We also added a second vacation rental near the Sonoma Coast, a stretch of country that's carried us through a family loss, given us long days outside with our kids, and pulled us out of the day-to-day for years.
This one was not turnkey. Then, in October 2021, a faulty toilet flooded the house and we had to remodel it. Nothing about that was in the plan, and it taught us a great deal in a very short time. I'll write about what it taught us.
What's next
We're finishing our first major renovation of the Joshua Tree cabin, the first real work we've done to it in four years. New professional photos arrive next week, and I'll use them to walk through what we changed, why we chose those upgrades over others, how we managed the work, and what we still haven't fixed.
That project is the model for what I want to write here. I want to bring 20 years of design and technology thinking to real estate and hospitality: the decisions, the numbers behind them, the mistakes, and the parts nobody puts in the listing photos. I'm not writing as an expert. I'm writing as someone three properties in, learning fast, and hoping the dialog teaches me as much as it teaches you.
If real estate, short-term rentals, hospitality, design, and the business of running all of it sound interesting, there's more to come. If you know someone deep in their own first experiment, send this to them.
I'm still learning what these houses can teach me about design, permanence, and hospitality.
Tell me about your experiment