On Owning and Operating Things
The fantasy of freedom, the reality of stewardship
Palmer House I, 2020
We celebrate vision. We celebrate exits.
But in between is the slow, often overlooked work of actually keeping something alive. That’s the part no one talks about—and the part that’s taught me the most.
When my wife and I bought our first house in 2015, we were 27, broke, and all-in. We did nearly everything ourselves. We got flooded. We rebuilt. And in the process, we found something larger than homeownership: a break from abstraction. From desk work. From the mental churn. A chance to move, to make, to solve. It wasn’t a side hobby. It was the beginning of something deeper.
By 2019, we bought our first two investment properties and started what became a full-fledged portfolio. I was still working full-time at YIELD, the design company we had co-founded—deskbound and drained. Getting to peel off for a day or two each week to move, to fix, to build felt like freedom. The work was tangible. Embodied. And it gave me something I didn’t realize I was missing: control.
But there’s a strange arc to building things. In the early days, you’re at the wheel, doing everything you can to get the vehicle moving. And then, at some point, you look up and realize you’re not driving anymore—you’re being dragged behind the thing, flailing, trying to climb back in.
I’d felt that way with YIELD and I soon found myself feeling the same way towards the property work: a reluctant landlord, a jack-of-all-trades juggling AC units, water heaters, roof leaks, guests, tenants, inspectors. What once felt like creative release now felt like a weight I couldn’t put down.
So we tried to outsource the burden. We hired a high-end property management firm promising a turnkey solution: maintenance, guest communication, tax compliance—everything. The pitch was seductive: automation, scale, freedom.
The reality? Less so. And honestly, I don’t blame them. The problem wasn’t their execution—it was the structure itself. The incentives were misaligned, and the added layers made things slower, more expensive, more impersonal.
I still found myself pulled into decisions I’d hoped to avoid. And worse, I started to feel foolish. Why am I paying someone to mismanage what I could do faster, cheaper, and better? Why am I handing over authority to someone who has no skin in the game—no real stake in the outcome?
Eventually, we pulled the plug. Because here’s the hard-earned truth:
There’s no such thing as a self-sustaining system. Not when you actually care.
Third parties can handle tasks. But they can’t replace presence.
They can’t replicate judgment.
And they can’t teach you what the thing is trying to tell you.
The fantasy of freedom through outsourcing is everywhere.
“Set it and forget it.”
“Build systems, not jobs.”
“Don’t work in the business—work on it.”
It’s the gospel of scale, and I get the appeal. But the deeper I’ve gone—first in our design business, then in real estate—the more I’ve come to believe that some weight is worth carrying. Being close to the work—close to the thing you’ve made—keeps you honest.
No, I don’t do every repair. I’m not a martyr, or a total control freak. But I know this: when an issue arises late on a Saturday night, I can usually tell whether it’s a nuisance or a real emergency—because I know the space. I know the systems. I know what we’ve built.
There’s a dignity in operation that gets lost in our obsession with vision.
We celebrate founders, not stewards. But the long-term health of anything—a business, a building, a marriage—depends not just on how well it was imagined, but on how well it’s tended.
That’s the difference. Operating isn’t about control.
It’s about care.
We’re now in the process of lightening the load—selling one property, listing another. It’s not defeat. It’s clarity. Owning and operating things isn’t about hoarding responsibility. It’s about taking seriously the things you choose to keep.
We don’t need to own everything.
But the things we do own—the spaces we shape, the teams we lead, the tools we build—we’d do well to stay close to them.
To understand them.
To tend them.
To stay in the driver’s seat, even if the road gets rough.
It’s easy to dream up a system that runs without you.
Harder to build one that deserves your presence.
The trick is knowing the difference.