People ask me about my path to becoming a business owner more than almost anything else. It comes up on panels, in client meetings, and in casual conversations that somehow turn serious. So, I figured it was time to actually share my personal journey and what I learned along the way about entrepreneurship.
The honest answer is I never intended to become a business owner. It wasn’t a plan I hatched or a dream I chased. It was a response to shrinking options and the willingness to act when others waited. That distinction matters more than most people realize.
How It Started
My first foray into entrepreneurship began when I discovered a product called Invisible Fencing. When I contacted the company to buy one, they told me there was no local dealer. I wasn’t looking for a side hustle or a business opportunity. I genuinely just liked the product, so I offered to act as a part-time dealer. They agreed to try it as an experiment, and suddenly I was in business.
I learned marketing and sales directly from them. Informal, unplanned, and it worked for several years until it didn’t. Because I kept treating it as a side hustle rather than committing full-time, they eventually told me I had to make a choice. I hadn’t built enough traction to give up my day job, so I walked away. But my experience planted the entrepreneurial seed. I now knew I could make sales and manage cash flow.
During that same period, I held a full-time job as a cost center and site manager at a minicomputer company. I was a high performer and generally good at what I did. But the minicomputer industry was in decline as personal computers were replacing them. I began getting calls from my manager back east every few months, telling me to lay off a few more staff. Each call was another data point. I could see where it was heading, and I started thinking about what came next.
The Move That Changed Everything
When the right moment came, I made a calculated move. The work itself wasn’t going away. But the company needed to meet its layoff targets, and their death-by-a-thousand-cuts approach, cutting people in small waves every few months, was destroying morale. The people who had options were already looking around.
I negotiated an alternative. If I quit and launched my own company, they would contract with me for the services my team had been providing. It solved their problem cleanly and gave me a foundation to build on.
I gave notice. My manager flew out to formally lay off my remaining staff. Every one of them received a generous severance package, including two colleagues I had already lined up as business partners. That severance gave them the capital to invest. They came in as minority partners, each at 10%, while I retained 80%.
As my former colleagues walked out of the building that day, I was waiting in the parking lot with employment contracts in hand. I hired many of them on the spot and immediately sold their services back to the same company that had just let them go.
Over the next several years, we opened offices in the Boston area, diversified our client base from minicomputer companies into telecommunications and smaller regional businesses, and deliberately reduced our dependence on that single founding contract. We started with roughly 10 employees and about $1 million dollars in revenue. By the time we reached our first exit, we had grown to around $1.6 million. Starting with one anchor client is a practical way to get off the ground. Staying dependent on one client indefinitely is just trading one vulnerability for another. We knew that and built accordingly.
That growth eventually drew the attention of a publicly held company based in Boston, which acquired us and brought me in to run their services division. But what actually attracted them wasn’t our revenue. It was our infrastructure. We had spent years building the kind of operation that could recruit talent away from corporate America. That meant competitive salaries, health benefits, SOPs, and an employee stock purchase plan. None of the other companies they had acquired had anything close to that. My company became the platform that everything else rolled into, essentially operating as a subsidiary of the parent.
Within that larger organization, my bosses quickly noticed something. I could walk into a prospective client’s office, read the situation, and reframe the entire pitch on the spot. Our product was a robust XML-based technical documentation tool with a steep learning curve. Most clients were struggling to get their existing staff to adopt it. Their writers had spent careers working on yellow legal pads and handing copy off to typesetters. Asking them to learn markup language was a hard sell. So instead of pushing the software harder, we changed the offer entirely. Don’t buy the tool. Hire us to do the work instead.
That pivot, combined with opening offices in cities where our clients operated, is what drove the next phase of growth. But what my bosses recognized, and what their career corporate peers couldn’t replicate, was something deeper than a sales technique. I could build and scale an operation from scratch. I understood what clients actually needed, how to compete for talent, and how to structure a business that could grow fast under pressure. Those instincts don’t come from a management course. They come from having run your own business and felt the consequences of every decision personally.
They handed me an open checkbook and told me to grow. This was the height of the dot-com boom. Revenue was the metric that mattered, and capital was not the constraint. We went on a hiring frenzy, opened offices across the country, and grew the combined revenue of three acquired companies from roughly $8 million to $32 million in under two years. At our peak, we were running between 250 and 300 people. It was a rocket ship, and for a while, it felt like it would just keep climbing.
Then they, too, were acquired.
The new acquiring company had one specific agenda. They wanted the engineers who had built the XML software. Those engineers represented roughly half of all trained XML professionals in the country at that time, and the acquirer was effectively buying access to that talent pool. The $32 million services division I had built didn’t fit what they came to buy. It wasn’t that the division was struggling. It simply wasn’t the asset they wanted. And just like that, my people were exposed again.
Same movie, different chapter.
I moved quickly. Working with one of my original partners, who again came in as a minority shareholder, we reacquired the assets of my original company and the Milwaukee operation, both of which had been picked up by the publicly held company during the Boston years.
That acquisition was strategic on two levels. It brought in an entirely different client base: a major crane manufacturer, a large farming equipment company, and a significant power systems client, and it reduced my original minicomputer client’s share of our overall revenue from a dangerous concentration down to something significantly more manageable. Client diversification wasn’t a nice-to-have at that point. It was the whole point.
I was deliberate about what I took. The dot-com era was over, and the rules had changed. As a publicly held company, revenue was the metric that mattered because Wall Street rewarded growth. Back on our own as a private company, profit was what kept the lights on. Revenue without margin wasn’t a strategy anymore. It was a liability.
Most of those contracts weren’t profitable, and we couldn’t absorb the fixed costs of maintaining a 250 to 300-person operation across multiple offices without serious outside investment. We were funding the reacquisition with the proceeds of the first sale, which defined what was possible.
So, we cherry-picked. We took the contracts closest to profitability and the employees who were the strongest performers. The contracts I left behind looked attractive on paper but were quietly bleeding money. Loss leaders that required enormous effort for margins that never materialized. I personally negotiated the underperforming contracts to competitors, who largely jumped at them because the revenue numbers looked impressive. Many of them eventually choked on it. They saw big dollars and didn’t see the pain that came with it. Those clients drained their organizations while we stabilized ours.
Everyone I didn’t bring with me landed softly. I made sure of that.
Over the next few years, we stabilized operations, tightened the model, and built something that could run without chaos. What had been a 250- to 300-person operation at its peak became a focused team of around 30. The underlying business was solid. For a cash buyer coming in without the debt we were carrying, the numbers worked cleanly. That was the version I sold to a private buyer who could take it to the next level. Exactly the right outcome at the right time.
Let me be direct about the real advantages, because they are significant and most people who haven’t done this underestimate them.
Autonomy. The ability to direct my own work without waiting for an institution to decide what I’m worth or whether I still had a seat at the table. That part mattered more than most people knew. I never went to college. I never had the kind of pedigree that makes a resume impressive. On paper, I was easy to undervalue. Employers could look at my background and make a quick judgment that had nothing to do with what I could actually deliver. Owning a business fixed that. Results don’t care about credentials. I learned early that the only reliable way to be judged on output was to own the scoreboard.
Resilience through diversity. When you work for someone else, you have one income source. All your eggs in one basket. One decision by someone above you, and it’s gone. When you own a business with multiple clients, losing one hurts, but it doesn’t end you. That’s the same principle behind a diversified investment portfolio, and it’s just as real. I lived this directly. Every time an acquisition put my people at risk, having a diversified base of clients and relationships gave me options that a single-employer dependency never would have.
Speed and maneuverability. Small businesses are lighter on their feet. I watched large organizations schedule meetings to discuss opportunities that had already closed by the time they convened. I could read a market shift, make a decision, and be moving before a corporate counterpart had finished drafting the agenda. That’s not a personality trait. It’s a structural advantage that comes with owning the decision.
Better thinking overall. Running a business forces you to develop a working understanding of incentives, customer behavior, cash flow, and organizational dynamics that most employees never have to engage with seriously. When you’re on payroll, you can specialize and stay in your lane. When you own the business, every broken system is your problem. Markets are brutally honest feedback mechanisms. That discomfort is uncomfortable on purpose. It makes you sharper.
A quiet kind of job security that nobody talks about. When the economy contracted, I knew I was the last one who would lose my job. I was the one who decided who stayed and who didn’t. That confidence was more than I expected, and it’s something a W-2 paycheck can never fully replicate.
The Part Nobody Talks About
Here’s where I want to be more precise, because the entrepreneurship content machine glosses over this far too easily.
There were days I questioned everything. Not in a philosophical way. In a real, 3 a.m., staring-at-the-ceiling kind of way. I had lives in my hands. People with families, mortgages, and kids in school. That weight doesn’t stay at the office. You carry it home.
Having to lay off people you recruited, people who trusted you, people who followed you from one company to the next, that doesn’t get easier. It’s one of the hardest things I’ve done in business, and I’ve had to do it more than once.
Freedom and anxiety are a package deal. The same independence that made me feel capable also created a kind of chronic vigilance that was hard to turn off. I managed it. But not everyone has the same tolerance for that kind of sustained pressure, and anyone who tells you otherwise hasn’t carried a payroll through a slow quarter.
Getting a business or personal loan is also harder when your income fluctuates. Lenders are built around predictable salaried income. When you’re self-employed, even with a profitable business, you often look riskier on paper than an employee making half what you do. That’s a real friction point, especially early on, and anyone considering this path should go in with eyes open about it.
Entrepreneurship is work. Real work. Anyone telling you otherwise is selling something.
Is entrepreneurship something you chose, or just something you’ve never seriously examined as an option?
