He had been at the same insurance company for twelve years. Nobody knew that his evening project, by year ten, had been earning more than his salary.
The insurance company was a small regional commercial-auto underwriter with offices in the South Side Works development along the Monongahela River in Pittsburgh. The company had about two hundred employees. Daniel Wojcik had been employee number seventy-three when he had started in 2013. He had been twenty-six. He had stayed.
He had stayed in the small same role for the first six years — junior commercial underwriter, then commercial underwriter — before being promoted, in 2019, to senior commercial underwriter. He had been promoted again in 2023, to underwriting team lead. He was, in the year I am writing about, a quiet thirty-eight-year-old man who managed a team of six underwriters, wore the same kind of small flat-front khakis every weekday, and drove the same 2017 Subaru Outback he had bought used in 2018 with a loan from his credit union.
He lived in a small two-bedroom rental house in the Brookline neighborhood with his wife Joanna and their two daughters, Iris and June, who were eight and five. Joanna worked as a pediatric occupational therapist at a private practice in Mount Lebanon. They were, by every visible reading of their small loose neighborhood, the small steady kind of Pittsburgh family that the slow careful Brookline streets were full of.
He had also, since 2015, been quietly building something else.
II. The thing he had been building.
The thing he had been building had started, by his own honest later description, as a irritation.
He had been, in his second year as a junior commercial underwriter in 2014, spending approximately ten hours a week of his small underwriting work on the task of pulling small commercial driving records from the small loose patchwork of small state-by-state department-of-motor-vehicle systems. The task had been the small most tedious portion of his underwriting workflow. Each small state’s small DMV system had its own quirks. Pennsylvania’s system was the bad one. Ohio’s was the worse one. West Virginia’s was the worst one. He had been, by his own honest later description, watching himself spend approximately twenty percent of his working hours on a data-pulling task that, by every honest engineering reading, ought to have been automatable.
He had begun, in the evenings of late 2014, to teach himself Python.
He had taught himself Python by the method of buying a small paperback book called Automate the Boring Stuff with Python, by Al Sweigart, and working through the exercises in the slow patient evenings at his small kitchen table between approximately seven and nine in the evening, Monday through Thursday. He had finished the small book, by his honest later spreadsheet, on the Sunday afternoon of the third weekend in March of 2015.
He had then, in the slow patient evenings of the spring of 2015, written a script that automated the data-pulling task he had been doing manually at the small insurance company. The script had taken him, by his honest later spreadsheet, approximately eighty-two evening hours over fourteen weeks to write.
It had reduced the weekly time he spent on the task from approximately ten hours per week to approximately twenty minutes per week.
He had not, in any way, mentioned the script to his manager. He had not, in any way, mentioned it to his colleagues. He had simply, by his honest later description, continued to do the task — now in twenty minutes per week instead of ten hours — and had used the recovered nine hours and forty minutes of small weekly small office time to do the other work that the small insurance company paid him to do, with the result that he had, in 2015, hit one hundred and forty-eight percent of his underwriting productivity targets and had received a year-end bonus of approximately five thousand four hundred dollars.
He had decided, by the honest evening conversation he had had with his wife Joanna at the kitchen table on the Sunday of the second weekend in December of 2015, to keep building.
III. The first sale.
The first sale had been to a small commercial-auto underwriter in Erie.
Daniel had identified the underwriter — a firm called North Erie Commercial Risk — through a industry directory he had been quietly reading in the evenings of early 2016. The firm had about thirty employees. It had been founded in 1971. It was, by every reasonable reading of the commercial-auto-underwriting market, the kind of firm that was likely to be doing the manual data-pulling task that Daniel had automated and that was, by its size, the kind of firm that could not, in any practical sense, afford the six-figure enterprise software solutions that the larger industry vendors were selling.
He had cold-emailed the underwriting manager at North Erie Commercial Risk on the evening of the third Wednesday in February of 2016. The email had been about three hundred words. The email had said, in summary, that he had built a tool that automated the data-pulling task across forty-seven state DMV systems, that he was willing to license the tool to firms like North Erie at a monthly fee, and that he was willing to provide a two-week free trial to any firm willing to try it.
The underwriting manager — a man named Frank Bellotti — had emailed back at six in the morning the following day. The email had said only: Send me the trial. I have been looking for this tool for four years.
Daniel had sent the trial. North Erie had used it for fourteen days. Frank Bellotti had emailed Daniel on the evening of the third Sunday in March with a offer to license the tool at three hundred and fifty dollars per month, with a annual contract.
Daniel had accepted.
He had not, by his honest later description, expected the cold email to result in the paying customer in five weeks. He had expected, by his honest internal estimate at the time, to cold-email approximately forty firms over six months and to acquire perhaps two paying customers.
By the end of 2016, RouteCheck — the name he had given the tool — had eleven paying customers, all small commercial-auto underwriters in Pennsylvania, Ohio, and West Virginia. The revenue, by his honest spreadsheet at the kitchen table on the Sunday afternoon of New Year’s Eve 2016, was approximately forty-six thousand dollars in annualized recurring revenue.
He had not, in any way, mentioned RouteCheck to anyone at the insurance company.
IV. The arithmetic of staying.
I want to be careful, in writing the next part, about how I describe the decision Daniel made between 2016 and 2024 to keep his day job at the insurance company even as RouteCheck slowly grew. The popular American story of quiet employee who builds a side business tends, by its shape, to compress the decision into a dramatic moment of the employee finally quitting in triumph. The actual shape of Daniel Wojcik’s eight years between his first paying customer in March of 2016 and the Sunday-afternoon decision he made in October of 2024 was not, by his honest spreadsheet, a dramatic moment.
It was a slow careful set of years.
By the end of 2017, RouteCheck had twenty-seven customers and approximately one hundred and twelve thousand dollars in annual recurring revenue. Daniel’s salary at the small insurance company that year had been about eighty-four thousand dollars.
By the end of 2018, RouteCheck had fifty-one customers and approximately two hundred and ten thousand dollars in annual recurring revenue. Daniel’s salary had been eighty-nine thousand.
By the end of 2019, RouteCheck had ninety-four customers and approximately four hundred and twelve thousand in revenue. Daniel’s salary, after his promotion to senior underwriter, had been ninety-six thousand.
By the end of 2020 — the Covid year, during which Daniel had quietly worked from home and during which RouteCheck's market had quietly accelerated as small underwriting firms had been forced to operate remotely without their in-office data-pulling workflows — RouteCheck had two hundred and eight customers and approximately one million two hundred thousand in annual recurring revenue. Daniel’s salary had been ninety-eight thousand.
The arithmetic of staying at the insurance company had begun, by the end of 2020, to be a arithmetic that did not, on its face, make any sense.
He had stayed.
He had stayed, by his own honest later description in our conversation in late August, for three reasons.
The first reason was Joanna. They had agreed, by gentle joint conversation in late 2018 when Iris had been five months old and RouteCheck had been at one hundred and seventy thousand in revenue, that they would treat the small RouteCheck income as a separate household line item and that they would not, by their gentle joint decision, allow it to change the shape of their small Brookline life until Daniel had built up at least three years of stable household reserves equivalent to three times Daniel’s insurance-company salary. The reserves, by their honest spreadsheet, would protect the family if RouteCheck ever failed.
The second reason was the work itself. Daniel had, by his honest later description, genuinely enjoyed his work at the small insurance company. He had liked his colleagues. He had liked the intellectual texture of commercial-auto underwriting. He had liked the people on his team. He had not, by any honest internal accounting, been in any hurry to leave a job he liked simply because a side business had grown larger than the salary the job was paying him.
The third reason was the structural fact that he could not, by his honest internal reading, let any of his small RouteCheck customers know that he was, in his day job, an employee of one of their competitors. The commercial-auto-underwriting industry was a industry. If word had got around that Daniel Wojcik of the Pittsburgh insurance company was the owner of RouteCheck, the customers would have, by every reasonable industry reading, churned within weeks. He had kept the separation absolute. He had not, by his honest later admission, ever met any of his small RouteCheck customers in person.
V. The October of 2024.
The Sunday afternoon in October of 2024 had been, by Daniel’s honest later description in our conversation in August, the Sunday afternoon when the arithmetic had finally, by gentle joint conversation with Joanna at the kitchen table in Brookline, crossed the threshold that they had agreed in 2018 would be the moment of change.
RouteCheck had, by his honest spreadsheet that Sunday, approximately seven hundred and forty paying customers and approximately three million eight hundred thousand dollars in annual recurring revenue. The household reserves had crossed, in late September, the three-times-salary threshold by a multiple of approximately fourteen.
The arithmetic, by every honest reading, had finally finished arguing with itself.
Daniel and Joanna had sat at the kitchen table for almost three hours that Sunday afternoon. Iris had been at a soccer practice. June had been at her grandmother’s house in Mount Lebanon. They had drunk coffee. They had gone over the spreadsheet line by line.
They had decided, by gentle joint agreement at approximately four-fifteen on the Sunday afternoon, that Daniel would, in the November, give the insurance company a three-month notice and would, by gentle joint decision, leave the job at the end of January.
He had given the notice on the Monday morning of the second week of November.
He had not, in the notice conversation with his direct supervisor — a slow woman named Anita Castillo, who had been his manager since 2019 — disclosed the reason. He had said only that he was, by his honest description, ready to do something different.
Anita had asked him, in the gentle way of careful slow managers, whether he had a job lined up.
He had said yes. He had not elaborated.
She had nodded. She had thanked him for the three months of notice. She had said only: Daniel, I have managed you for five and a half years. Whatever you are going to do next, you are going to be good at it.
VI. The January.
He left the insurance company on the last Friday of January.
The company had thrown him a farewell lunch at the restaurant on East Carson Street that they used for farewell lunches. The team had given him a framed photograph of the underwriting team from 2019 and a gift card to a Pittsburgh bookstore.
He had been small specifically moved.
He had not, in the lunch or in the subsequent farewell email he had sent to the company, said anything about RouteCheck.
He drove home that Friday afternoon at approximately three-thirty. He sat at the kitchen table in the Brookline house. He opened his laptop. He logged into the RouteCheck admin dashboard.
He looked at the list of seven hundred and forty paying customers, the annual recurring revenue of approximately three million eight hundred thousand dollars, and the list of customer support tickets that had come in over the previous twenty-four hours.
He started, by his honest later description, with the customer support tickets.
VII. The first nine months out.
I sat with Daniel Wojcik at his new office in a shared workspace in the South Side Flats neighborhood in late August, almost seven months after the Friday afternoon he had left the insurance company.
The new office was the opposite of dramatic. It was a small private office in a WeWork-style shared workspace. It had a standing desk. It had a second monitor. It had a framed photograph of Iris and June on the desk, and a small framed wedding photograph of Daniel and Joanna from 2014.
He had, by his gentle later description, hired four employees in the seven months since leaving the insurance company. The four employees were two software engineers, one customer support specialist, and one accounting and operations manager. The four employees did, by gentle joint description in our August conversation, approximately the portion of the work that Daniel had been previously doing in the evenings and on the weekends.
Daniel had, in his honest later description, finally been able to spend more than two hours an evening with his daughters.
He had, by his honest later description, finally been able to coach Iris’s Saturday-morning soccer team, which he had been wanting to do for two years and which the evening RouteCheck work had been preventing him from doing.
He had, by his honest later description, finally been able to be at every one of June’s kindergarten end-of-week show-and-tell sessions, which had been happening every small Friday morning at ten and which he had been able to attend, by the accidents of his underwriting schedule, only three times in the previous year of RouteCheck still being a evening business.
I asked him, near the end of our conversation, whether he regretted not having left the insurance company earlier.
He thought about it for a long moment.
“No,” he said. “The seven years between 2016 and 2024 were the years when Iris was small. They were the years when June was being born. They were the years when Joanna was building her practice in Mount Lebanon. If I had left the insurance company earlier, the household would have been, by every honest reading, less stable. The arithmetic was not, by my honest later reading, an arithmetic of how much money I could make. The arithmetic was an arithmetic of how stable the household needed to be in order for the children to grow up the way Joanna and I wanted them to grow up. The stable salary at the insurance company was, in that arithmetic, the anchor. The RouteCheck income was the accumulating buffer.”
He paused.
“I do not, in any sense, regret being a quiet employee for twelve years,” he said. “I regret only — by the smallest possible specific honest internal margin — that I did not manage to be at more of June’s Friday morning show-and-tell sessions in 2024.”
The slow careful arithmetic of an honest American small-business builder is, sometimes, the arithmetic of building the stability under the household for as long as the household needs it, and not a minute sooner.
VIII. Why it stays.
I have been writing for The Chapbook for almost nine years, and the stories I have come to write most carefully are the stories where the shape of an American small-business success is not, by any honest reading, the dramatic departure from the corporate job. It is the slow patient overlap of the corporate job and the evening project for as long as the household requires both.
Daniel Wojcik was not, by any honest reading, the kind of founder that business publications like to write about. He was not, by any honest reading, the kind of founder who quit a job at thirty to chase a dream. He was, by his own honest description, a quiet thirty-eight-year-old Pittsburgh insurance employee who had spent twelve years at the same company while quietly building, in the evenings, a software business that had become — by the October of his thirty-eighth year — large enough to justify the departure he had been arithmetically preparing for since 2018.
The shape of his work is, in every honest reading, the shape of the majority of American small-business builders. Most of them are not twenty-five-year-olds quitting tech jobs in San Francisco. Most of them are quiet thirty-eight-year-olds in Brookline rentals running evening businesses at the kitchen table.
Across the United States, in insurance offices and software companies and kitchen tables in Brookline rentals, the quiet long-tail majority of American small-business builders are building, in the evenings of Monday through Thursday, the things that will, by the arithmetic of the next eight or ten or twelve years, become the actual businesses they will, in the time, leave the corporate jobs to run. For broader context on the long American history of bootstrapped software businesses and the available infrastructure of employee-to-founder transitions, readers can spend time with the materials at the U.S. Small Business Administration or the long-form reporting at PBS NewsHour. The Chapbook keeps its narratives clean, human, and responsible — read more in the Editorial Policy.
RouteCheck is, this October, at approximately eight hundred and eighty paying customers and approximately four million six hundred thousand dollars in annual recurring revenue. Daniel has, by his honest later description in our August conversation, no plans to sell the company. He has, by his gentle joint decision with Joanna in August, only plans to continue, by the evening-and-weekend rhythm of careful steady Brookline parenting, to run it the way he has been running it.
He is, this October, the assistant coach of Iris’s Saturday-morning soccer team.
He has, by his honest gentle later description, not missed a single Friday-morning show-and-tell of June’s kindergarten class since the Friday of February the seventh.
