When I started my career, I was fully remote, nominally hybrid. In practice this meant two people showing up to say hi to a VP quarterly. It was a post-COVID hangover period: Amazon hadn’t gone full-throttle on RTO yet, and the first big round of layoffs was looming.
In contrast, my new job at a small startup in San Francisco is in person five to six days a week. That might not sound unusual — except that in-person work is deeply tied to what makes the company move.
Our earliest market tests included a huge amount of outbound email, LinkedIn, and cold calling. These did not yield much progress. We didn’t really start meeting customers or building momentum until we got in a car and drove out to see people. We started building real relationships with property managers in California by doing a literal traveling-salesman loop: mapping offices, deciding the best order to visit, and showing up in person. That early bias toward “being there” has become basic company culture.
Our first meaningful interaction with a customer came from driving out to Sacramento, buying a property manager, Cheryl, lunch at the Rebel Hen Cafe, and talking about what might be worth building (we didn’t have anything to sell yet). We used Clay and publicly available property-management lists to identify medium-to-large single-family property management companies in Sacramento, mapped them out, and planned our route.
Lunch with Cheryl covered a lot, quickly — many of the same themes we’re still working through from a product perspective. Reviewing our list of targets, Cheryl made a key introduction: she connected us to one of the best-regarded companies in the area. RentPros. The owner of RentPros told us, “If you’re willing to come by, we’ll see you.”
So we went. We found ourselves in the conference room at RentPros Property Management, where we spent the next three hours going through their business in careful detail. Their biggest pain points and where software vendors had failed in the past. Again, we had nothing to sell, but they appreciated the handshake and the seriousness it signaled.
We kept building relationships face-to-face. Up next was sitting in on breakfast with members of the National Association of Residential Property Managers Granite Bay chapter. There we met an AI-pilled, fast-moving operator in the room — someone who became the perfect first client and test case. He was genuinely excited by automation, understood change was coming, and was unusually open with his time. That partnership gave us room to experiment and stress-test a bunch of our earliest ideas.
Building in person with our customers has produced some surreal moments. We returned to RentPros’ conference room having ingested their data and armed with the Supabase MCP + Claude. We cast onto their boardroom TV and chatted live about their data — finding recent tenant issues, spotting patterns, and answering questions on the fly (like what percentage of maintenance requests were reported over the phone vs email). They were used to their data being locked behind restrictive ERPs with terrible reporting for two decades. Sitting together with a conversational interface that could answer any question about their business felt like magic.
This pattern of “Show, don’t tell” is much more effective than asking someone to speculate about software. In another moment, we showed up to the office of a property management company with a software duplicate of a pencil-and-paper logbook used to run a maintenance department for thirty years. We sat alongside a low-vision older man observing how he used our software. We watched every unintuitive interaction and pushed changes live in the room — changing UI, adding to the data model, and adapting to his accessibility needs. In-person we improved the product by a degree we couldn’t have imagined over weeks remotely.
On a different axis, building in person has also meant building an office environment and vibe from scratch. We obsess over the little things in a way that’s strangely satisfying. We hunted for a ground-floor, but protected from the street office, that had a busy feel but had to have a private entrance to escape the co-working “maze walk of shame”. As we drifted into something like a 996 schedule, we taped a long, torn, Costco receipt into “tendrils” around our motion-detecting light sensor and pointed an oscillating fan at it to prevent our lights from shutting off every 15 minutes, triggering the crab-waddle in our desk chairs to regain light.
We even have some “core infrastructure” bleeding into the office: a Raspberry Pi setup with a particular ngrok tunnel that gives us a sticky residential IP, for god knows what 👀.