What if the right entry point into entrepreneurship is not buying a business but learning whether you are actually built to run one?
Most first-time buyers assume acquisition is the faster, safer path. They picture stepping into an established operation and skipping the messy early years. But when Stephen Olmon looked back on his first attempts to buy a company, he had a different conclusion. Buying looked attractive. Building was what prepared him.
Stephen put two deals under LOI early in his career. Both failed in diligence. At the time, he did not have capital, operating reps, or a background in business ownership. That combination forced him to confront an uncomfortable truth. He was trying to buy before he understood what it meant to run something.
That realization shaped everything that came next.
Build the Skill Before You Take the Risk
Stephen did not come from a business family or from private equity. He had no early exposure to M&A, no financial backers lined up, and no real deal experience. After the failed LOIs, he and his wife were still working through student debt. Buying was not off the table, but it was clear he was not ready.
So he went the NewCo route. He started a marketing agency. He launched a few small ventures. He learned what it meant to sell work, deliver work, and sustain cashflow. These early businesses were not glamorous, but they gave him confidence, capability, and leverage. They gave him the foundation he did not have when he first tried to buy.
Building was not a philosophical choice. It was a practical one.
Why New Entrepreneurs Miss This
Stephen believes many first-time buyers underestimate how difficult buying a business actually is. He has watched friends go bankrupt. He has seen people chase deals because they look accessible, not because they fit their skillset. He has seen entrepreneurs get drawn in by the idea of acquisition without understanding the operational realities waiting on the other side.
He is explicit about the danger. Buying requires self-awareness. It requires knowing what you are good at, what you are not good at, and whether you have the network and support system to take on meaningful debt. Too many people skip this step and walk directly into a business they are not equipped to lead.
In his view, that is where most new buyers go wrong.
The Shift That Changes Everything
Today, Stephen has acquired multiple companies. He helps run a growing fire and life safety platform. He manages M&A activity while building out sales, marketing, and operations. But he only reached this stage after years of building businesses that taught him how he operates, what environments he thrives in, and what kinds of companies he should buy.
He does not argue that everyone must build first. He argues that most people should, unless they have a specific background, network, and support system that makes buying less risky. His message is not “never buy.” It is “understand yourself before you buy.”
That shift changes the outcome of the first acquisition more than anything else.
What Building Gives You That Buying Cannot
Stephen’s path highlights the practical advantages of building before buying. Building forces you to learn the fundamentals that acquisition often masks. It gives you clarity, discipline, and resilience. It teaches you who you are as an operator long before closing day.
Here are the benefits that shaped his later success:
- A realistic understanding of how businesses behave day to day
- Better judgment during diligence and negotiation
- More credibility with lenders, investors, and sellers
- Cashflow and experience that reduce personal risk
- The ability to walk away when a deal is not a fit
These are advantages building creates naturally. Buying does not guarantee any of them.
Why Stephen Recommends Building First (For Most People)
When Stephen answers the question “Do you recommend buying over building?” he calls it dangerous. Not because buying is wrong, but because the right answer depends entirely on self-awareness. People with a strong financial background, a supportive network, and clear alignment with a specific industry may be well suited to buy immediately. Most people are not.
For those people, starting something small is the cleaner way to learn. Building reveals your strengths. It exposes your blind spots. It helps you understand whether entrepreneurship is the right path at all. These insights matter more than deal terms, valuation, or lender selection.
If buying is a leap, building is preparation.
The Takeaway
Buying a business gets you into the operator’s seat. Building a business prepares you for the realities of staying in that seat. Stephen’s experience shows that timing matters. Sequence matters. And the people who start by building often enter acquisitions with more clarity, capability, and control than those who try to skip the reps.
Buying is not wrong. It is simply not always first.
For most entrepreneurs, building is what makes buying possible. Here’s my entire conversation with Stephen.
