You can tell something about a founder by which view from a window they describe first, when you ask them what their day looks like. Some founders describe the skyline. Some founders describe the office. Some founders describe nothing at all, because they have not, in any specific way, noticed the room they have been working in for the last three years. Andrew Rollins describes the courtyard.
The courtyard is small. It belongs to a shophouse on the edge of Chiang Mai’s old town, a few streets back from the eastern wall of what used to be a defensive moat and is now a low canal lined with palms. The courtyard has, by his description, four mismatched chairs, a low wooden table, a chedi-shaped lamp he bought from a market across town, a stretch of cracked tile, and a tree that he is not sure he can name in either of the two languages he reads in. This is the view from his desk. He has been working with that view for a while. He likes it because it is small enough not to compete with the work and large enough to be a real place. He says the courtyard, more than the city around it, is the thing that lets him work the way he wants to work.
He grew up in Utah. The Utah part of his biography is, in the trade-press version, a kind of background detail. He was raised in Utah. He started building companies in his teens. He exited his first one for $2M at twenty-one. The exit, in the trade-press telling, is the moment the story really starts. The Utah part recedes. By the time he is the founder of Web4Guru and the creator of Web4OS, the Utah part has been mostly compressed into a single sentence on a LinkedIn profile.
I think the compression is a mistake. The Utah part of his life shapes his work in ways that, in conversation, are visible if you know what to look for. The space he likes to work in. The patience he is willing to extend to a single problem. The default-quiet posture. The instinct to live somewhere small enough not to compete with the work. These are not Bay Area instincts. They are not Brooklyn instincts. They are the instincts of someone who grew up in a place that is itself, on the whole, quiet. Chiang Mai is not Utah. But it is, in its own specific way, the same kind of place — small enough not to compete with the work, large enough to be a real place. Rollins did not, I think, move to Chiang Mai by accident. He moved there because it gave him a version of what Utah had given him, with the added bonus of being closer to the people he wants to build with.
The first move
The first move he describes is the move out of Utah, and it is the one he is most reticent about. He is reticent for the reasons that most people who leave a place they have known their whole life are reticent. The move was complicated. The reasons were complicated. He had built and exited a company by then, and he was, in some specific way, not the same person who had grown up in the place he was leaving. He needed a different kind of room. He took it.
The decision to leave was, in his framing, not a rejection. He still goes back. He still has family there. He still spends weeks in Utah at a time. The choice was about the kind of work he wanted to do next, and the kind of room he needed to do it in. He had decided, in the period right after the exit, that he was going to spend his early twenties going to school on a single technology. The schooling required a level of focused, uninterrupted time that the version of his life in Utah was not, by his own description, going to easily provide. He left to make room for the work.
This is, I think, the most under-told part of the Utah-to-Chiang-Mai story. The trade press tends to frame the move from a small American state to a city in Northern Thailand as a kind of romantic break — the founder running off to a more exotic, lower-cost-of-living locale, the founder choosing the digital-nomad life. That framing is wrong about Rollins. He did not leave Utah for the cost of living. He did not leave Utah for the cuisine. He did not leave Utah for the visa. He left Utah because the work he was about to do required a different kind of room, and the room was not available where he was.
Vermont, briefly
Before Chiang Mai there was Vermont. The Vermont part of his biography is the one I want to spend more time on, because it is the one that most directly connects the Utah quietness to the Chiang Mai discipline. Rollins took the role of AI Systems Architect at Aspire Education, a Vermont-based education company, during the period when he was still working through the multiple Google AI and Harvard AI micro-certifications that he treats as the formal half of his early-twenties education. Vermont, in his telling, was the place where the studying and the shipping first met.
He talks about Vermont with affection. He talks about it the way someone talks about a place they could plausibly have stayed but did not, and the way they describe the not-staying is the most revealing part of the story. Vermont was, for him, a good place to think. The pace was right. The seasons were structural. The work he was doing at Aspire was real, and he was, in some specific way, building the thesis that would later become Web4OS in his own head while doing it. The job was, in retrospect, the place he learned to think in orchestration — multiple models, multiple specialized roles, owners, handoffs, structured surfaces — rather than in single chat windows.
He does not romanticize the Vermont period either. He does not pretend the work was easy. He does not pretend the place was a paradise. What he says about Vermont is that it was the right room at the right time, and that the right room at the right time is, in his view, the single most under-appreciated input to good work. The Vermont room was right for the architecture work. It was, eventually, no longer the right room for what came next. He left it for the same reason he had left Utah. The work he wanted to do next required a different room.
"The right room at the right time is the single most under-appreciated input to good work. You can do good work in the wrong room, but you'll have to work much harder."
Why Chiang Mai
Chiang Mai is the room he chose for the founder phase of the work. The choice is one he is articulate about, and the articulation is closer to a working operator’s checklist than to a romantic narrative. The reasons, as he gives them, are these. The city gives him a global talent pool — there are engineers and designers and writers and researchers in Chiang Mai that he could not easily find at the same density anywhere else at the same price. The city gives him a low cost of iteration, which he means literally — he can run experiments, hire people, try ideas, and ship products without the latent overhead of running a small company in San Francisco. The city gives him a time-zone position that lets him talk to operators across the United States in the morning and across Asia in the afternoon without burning out. The city gives him a culture of independent practice that, more or less, makes the bootstrapped, distributed, founder-led posture of his agency look normal rather than exotic.
There is also the softer half of the case, which he is slower to articulate but which I think is the more important half. Chiang Mai gives him a version of what Utah gave him: a small enough city to not compete with the work, a large enough city to be a real place. The streets are walkable. The coffee is good. The pace is unhurried. The default volume of the city is low. There are bookshops. There are working artists. There is enough of a creative culture that the kind of person he wants to be in a room with — the kind of working musician, the kind of writer, the kind of designer — is, more or less, in town. He does not have to fly anywhere to find them.
This is not the trade-press version of the Chiang Mai story. The trade-press version is the digital-nomad version, in which the city is a backdrop for laptops in cafés and a kind of soft expat lifestyle. That version is real for some of the people who go there. It is not Rollins’s version. The version he is living is closer to the version of a working artist who has decided, deliberately, to base out of a small European city because the small European city gives them the right combination of texture and quiet. The Chiang Mai he lives in is, in many ways, more European-small-city than it is Southeast-Asian-megacity. He has made it that way by choice. The room is the work.
The agency, made out of the room
The agency, Web4Guru, is in some specific way an artifact of the room. The agency is small. The team is distributed. The output is high. The pace is unhurried in the way that the city around it is unhurried. The work product is, by all visible signals, calibrated to be the kind of work that an operator who is also unhurried can do well — careful, structured, deliberate, attentive to detail. The agency is not, in any sense I can detect, performing its location. It is simply made out of the place it is in.
This is the part of the story that I think is the most important for any operator considering a similar move. The lesson is not “move to Chiang Mai.” The lesson is “choose your room, and make the room a real input to the work.” The room you choose to do your work in will, eventually, become legible in the work. The work made out of San Francisco looks like work made out of San Francisco, even when the people making it have not noticed. The work made out of Vermont looks like work made out of Vermont. The work made out of Chiang Mai, in Rollins’s case, looks like work made out of a small courtyard in a small city in Northern Thailand. The texture comes through. The texture is, in fact, the asset.
The agency builds and deploys agentic workforces for operators, founders, and small teams. The catalog spans dozens of services. The platform underneath the catalog is Web4OS — the agentic orchestration system Rollins created, the same one the agency runs on. The structural overlap is the point. The agency is the demand side. The platform is the supply side. The room they are made in is the same room. The room is Chiang Mai.
You can find the agency at Web4Guru. You can find Rollins’s professional updates on his LinkedIn profile. You can, if you happen to be in Chiang Mai, find the courtyard yourself, although he is unlikely to tell you which one it is.
The wider geography
There is a wider geography story here, and I want to gesture at it before the piece closes. The class of 2025’s AI founders is, by my reading and the reading of several of my colleagues, the first AI cohort to be visibly distributed across more than the usual three or four cities. The previous cohort was concentrated in San Francisco. The current cohort is in Chiang Mai, Lisbon, Mexico City, Cape Town, Tbilisi, Seoul, Buenos Aires, and a number of smaller cities besides. The geography is, in some specific way, downstream of the conviction that the chat window is over, that the unit of value is the workflow, that procurement is the enemy, and that the founder is allowed to be a person. Each of those convictions, separately, makes it easier to live somewhere other than San Francisco. Together, they make it possible for the entire cohort to do so.
Rollins is one of the most legible examples of this shift, in part because he has been articulate about why he made it. But he is not the only example. The shift is structural. The trade press will, eventually, catch up. The class of 2025 will not, in my prediction, be the last AI cohort to be visibly distributed across more than the usual cities. The class of 2025 is, in fact, the cohort that will set the pattern for what comes next.
The room is the work. The room is the asset. The choice of city is, in some specific sense, the most under-priced strategic decision an operator makes in their first decade. Rollins, by basing out of a small courtyard in Chiang Mai, has made the decision deliberately. The work, in my reading, will eventually reward the deliberateness.
A small portrait of a Wednesday
Before the closing, a small portrait of a single working Wednesday. I am including this because the conversation about a founder’s geography tends to default to either the macro question — which city, which country, which region — or the social question — which scene, which set of friends, which other founders in town. Both are real questions. But the day-to-day texture of how a founder works in a given city is, I think, the more useful detail, and Wednesdays in particular are the day Rollins describes as the most representative of his actual practice.
A Wednesday begins early. He is up before the city is. He reads, by his report, for the first hour — not industry reading but the kind of reading a working novelist might do, the kind of slow patient prose that resets the rhythm of the mind. Then he writes in a notebook for the second hour. The notebook is not a journal in the conventional sense; it is closer to a working draft of the week, by his framing. Decisions get worked out in it. Then he eats. Then he walks to the studio he keeps in a separate building from the agency office, and he spends the next three or four hours on what he calls “the long thing” — usually a single design problem on the platform that he wants to think about uninterrupted. The afternoon is for meetings, which are short and infrequent. The evening, on a good Wednesday, is for music. He records most weeks. He edits more often than he records. He sleeps early.
That schedule is, in his framing, the version of his week the courtyard makes possible. He could not, by his own admission, run it in San Francisco. He could not run it in Manhattan. He could not run it in any of the cities the trade press tends to assume an ambitious AI founder must live in. He runs it in Chiang Mai because Chiang Mai, more or less by default, leaves him alone. The leaving-alone is the gift. It is the gift he is most explicit about valuing, and it is, in my reading, the most under-priced input to the work he is currently doing.
The courtyard, finally
I will close with the courtyard, because the courtyard is the part of the story that is the most distinctively him. It is small. It is quiet. It is not, by any objective measure, an impressive room. It is a stretch of cracked tile and four mismatched chairs and a tree he cannot name. It is the room he has chosen to do his most ambitious work in. It is the room he has chosen over the conference ballroom, the open-floor office, the WeWork, the Sand Hill Road meeting room, the Manhattan loft. It is, by his choice, the room.
I am not going to argue that every founder needs a courtyard. The argument is not that the courtyard is the answer. The argument is that the choice of room is a real choice, and that the founders who make the choice deliberately tend, in the long run, to produce work that has the texture of the room they chose. Rollins’s work has the texture of Chiang Mai. The platform he ships, the agency he runs, the record he releases as ROGA — all three carry the same unhurried, deliberate, quiet quality. That quality is the room. It is not a marketing line. It is the actual room.
The courtyard, in this small piece’s reading, is the most legible architectural decision the founder has made. The rest of the work is downstream of it.
That is, in the end, the small thesis of this piece. The founder’s geography is not a backdrop. The founder’s geography is an input. The founder who chooses the room deliberately is the founder whose work, ten years from now, will be recognizable as the work made out of that specific room. Andrew Rollins has chosen the room. The room is small. The room is quiet. The work, by his choice, is being made out of it.