An office chair is an unlikely place to look for a founder’s philosophy. At Jason T. Roff’s software company, it is a reasonable place to start. He bought rollerblade wheels for the chairs so they would roll quietly. There are grander ways to announce that you care about the people writing your code. Few are quite so attentive to the sound of somebody moving six feet to the left.
The detail comes from Don Gregori, First Factory’s chief operating officer. It belongs alongside the company’s open workspaces and natural light: small decisions about the place where work happens. A chair is furniture, certainly. It is also something a person encounters repeatedly during a working day. Roff seems interested in that second description.
His company takes its name from Andy Warhol’s creative studios. The product here is software, and the founder’s background includes computer science, development management, and a shelf of programming books. Put those pieces together and a particular kind of entrepreneur emerges: a programmer who became interested in organizing the conditions around other programmers.
The programmer before the founder
Roff began developing software around age ten. He went on to study computer science with applied mathematics at the University at Albany, SUNY. His professional career began in the 1990s, well before First Factory became his full-time occupation. The company grew out of work he already understood from the inside.
At Isogon, his work included C/C++ client/server applications. That description has the pleasingly solid sound of an earlier computing era. It also locates him in the business of making systems work together, rather than merely discussing what software might someday accomplish. His later roles included development leadership and project management.
The books make this part of his career unusually tangible. ADO: ActiveX Data Objects, published by O’Reilly in 2001, concerns getting information across different formats and platforms. Its contents run through connections, recordsets, commands, events, and a substantial reference section. There is very little room in such a book for waving one’s hands.
UML: A Beginner’s Guide followed through McGraw-Hill, published in December 2002 with a 2003 copyright. It teaches a visual language for describing software. Where the ADO book helps a developer reach information, UML helps people describe what they intend to build. Roff was also one of the credited authors of Wiley’s ASP.NET Professional Secrets, published in October 2003.
A book also leaves a dated record. Software companies often describe themselves through their latest services; a bibliography preserves earlier interests with much less opportunity for revision. In Roff’s case, the record includes both the machinery of accessing data and the diagrams people use to agree on a design. That combination puts implementation and explanation on the same shelf.
These subjects offer a useful way into his working life. They involve turning something complicated into something another person can use. A technical author has to anticipate confusion, choose an order, and explain the missing step. Readers cannot summon the author each time a connection fails. The explanation has to survive on its own.
A factory with a different product
First Factory was founded in New York on March 14, 2000. The date happens to be Pi Day. Roff noticed the mathematical coincidence only years later, which is rather more endearing than a carefully engineered founding legend. Sometimes a company’s symbolism arrives after the paperwork.
The name was deliberate. Warhol’s Factory suggested a place in which creative people could work together. Roff translated that idea into an environment for software engineers. It is an interesting borrowing because the word “factory” ordinarily suggests repetition, while the work he describes depends on people solving unfamiliar problems.
Joel Spolsky’s writing supplied another influence, this time from inside the software business. Roff credits Spolsky’s ideas about treating developers well. The combination of an artist’s studio and a programmer’s management advice is less peculiar than it first sounds. Both put attention on the people doing the making.
It also gives the company name a practical burden. A creative environment has to be arranged, equipped, and maintained. Naming the place cannot settle questions about distraction, authority, or access to tools. Those questions recur after the sign goes up. They are the daily work concealed inside an attractive founding idea.
The office a client helped build
By 1998, Roff was working with 18 Ukrainian developers. First Factory later began as a side business; the move into a full-time operation came in 2006, when he opened its office in Heredia, Costa Rica. The starting team there consisted of four engineers. An early client helped finance the office.
That sequence matters. The founder did not simply choose a country and then go looking for a reason to be there. He had experience of operating across borders and wanted a more workable arrangement. The relationship with a customer helped turn that preference into an actual workplace.
Working hours were part of the calculation. So were direct conversations with developers, dependable office operations, and travel that would make visits practical. Costa Rica’s education system and relationship with the United States also figured in the choice. Roff wanted a place where the business could put down roots.
Nearshore development can sound abstract when reduced to a point on a map. Its consequences are ordinary and immediate: when a question can be answered, whether people can meet, how much of the day they share. Time zones have a way of becoming management decisions without asking permission.
The move also became personal. Costa Rica came to be a second home, and the company’s account says Roff and his family acquired dual citizenship. A decision about software operations had developed into a continuing relationship with a country. The office was part of a life as well as a business.
The customer who changed sides
Gregori joined First Factory as chief operating officer in 2017, after eight years as a client. He had experienced the company from the other end of the relationship before becoming responsible for helping run it. A customer’s knowledge is a useful kind of institutional memory to bring into management.
The transition also gives context to his observation about the chairs. He describes an attention to detail that extends into the working environment. Seen from his position, the office is part of what the company supplies: a setting in which the people serving customers can concentrate on their work.
The customer’s side of the desk brings its own education. You learn what it feels like to wait for an answer, to explain a requirement, and to depend on another team’s judgment. Bringing that experience into the company gives its promises a reader who has already tried to use them.
First Factory’s history includes five consecutive Inc. 5000 appearances, from 2020 through 2024. Such recognition records a stretch of business growth. It leaves open the more intimate questions that make a founder interesting: what he notices, whose judgment he trusts, and what sort of working day he is trying to make possible.
The habit of staying useful
One clue appears in a public recommendation Roff wrote for developer Jose Trejos. He described an employee who joined in 2021, earned two promotions, and worked with React, React Native, and Node.js. He also singled out Trejos’s decision to teach himself Python and deepen his understanding of cloud technology.
The specific technologies matter less here than the act of noticing. A recommendation gives a manager space to say what he values about another person’s work. Roff chose reliability, preparation, follow-through, and learning undertaken without waiting to be assigned it. Those are observable habits, useful well beyond a particular programming language.
His own career has crossed several generations of tools. The subjects of his books belong to a different technical moment from the AI development and cloud services First Factory offers today. In 2026, the company added Claude Select Partner status to its history. Roff remains its founder and CEO, with a biography that describes him as involved in daily operations.
“There are a thousand companies like us.”
Jason T. Roff
That is an unusually plain admission for a founder selling professional services. It puts the emphasis on what happens once somebody decides to work with you. An industry can contain many suppliers while an individual relationship remains quite specific: the people who answer, the context they remember, and the care they take with an unfinished problem.
Roff’s story has no shortage of larger markers: a company founded in New York, an office in Costa Rica, technical books, and years of customers and colleagues. Yet the quiet wheels remain a useful final detail. Somebody had to notice the noise, decide it mattered, and change the chairs. For a business built around concentrated thought, that is a perfectly respectable piece of engineering.