I find myself asking the same question over and over again:
Do I buy an existing business – or build something of my own again?
This question is not abstract anymore. It’s not a thought experiment or a conversation over drinks. It is real. It’s here. It’s happening now. Weeks after selling my own company, after the transition period slowed down and the calendar went quiet, I’m staring at this fork in the road in full daylight.
I’ve had capital. I’ve had experience. I’ve worked with due diligence teams on my own sale. I’ve lived through buyer questions – twice. I should be well-positioned to acquire something that’s already running, and start from an operational leg up.
At least, that’s what I used to believe.
Reality – The Acquisition Search
Once I decide to explore the acquisition route seriously, the process accelerates quickly.
I start taking calls. Introductory conversations at first, then deeper discussions with founders who are actively looking to sell. On the surface, it feels efficient. These are businesses with customers, revenue, and some form of operating history. In theory, I’m buying momentum rather than creating it from scratch.
But almost immediately, the gap between theory and reality starts to show.
The early conversations are usually optimistic. The story is familiar: solid growth, loyal customers, a great product, and a founder who’s “ready for the next chapter.” I listen, ask questions, and nod along. I’ve told similar stories myself in the past.
Then I begin to dig.
I ask for financials. I ask for customer data. I ask how decisions are made, how work actually flows through the business, and what happens when the founder steps away for a few weeks. These aren’t trick questions. They’re basic questions – the same ones buyers asked me during my own exit.
That’s when things start to slow down.
Documents arrive late or partially. Numbers don’t quite reconcile. Metrics are described confidently but supported loosely. Answers become more qualitative than quantitative. What initially sounded like a business starts to feel more like a collection of habits held together by the founder’s daily involvement.
I’m not looking for perfection. I know better than that. But I am looking for coherence – a system that exists independently of the person telling me the story.
Too often, it doesn’t.
And as these conversations pile up, a quiet discomfort starts to replace the initial excitement. Not because the founders are dishonest or incapable – most of them are neither – but because what I’m being shown isn’t leverage.
It’s a lot of work.
What I Actually See Once I Look Closer
Once the conversations move beyond surface-level storytelling, a consistent pattern emerges.
The financials are often incomplete, or at least not decision-grade. Statements exist, but they don’t always reconcile cleanly across periods. Revenue is real, but the underlying drivers aren’t clearly articulated. Margins shift depending on how the question is framed. Simple follow-ups – the kind any serious buyer would ask – take time to answer, not because the data is confidential, but because it doesn’t exist in a usable form.
Operationally, things are even less defined.
Processes aren’t written down. Roles are loosely understood rather than explicitly designed. Job descriptions, if they exist at all, reflect intentions rather than reality. Knowledge lives in conversations, memory, and improvisation. When I ask how work gets done when the founder steps away, the answer is almost always some version of “we figure it out.”
Customer data tells a similar story. Lists are outdated or fragmented. Contracts vary by relationship rather than policy. Terms evolve organically. There’s no single source of truth. Sales activity happens, but without a consistent system behind it. Forecasting is hopeful rather than disciplined.
None of this makes the founders bad operators. In many cases, it’s exactly how scrappy businesses survive and grow.
But it does make one thing very clear: what’s being offered isn’t a clean handoff. It’s an ongoing obligation.
What I’m evaluating isn’t just a business. It’s how much reconstruction I’ll have to do before the business can even be managed properly, let alone scaled or sold again in the future.
And slowly, the realization sets in that buying something like this doesn’t save time. It simply moves the rebuild to a different starting line – one that comes with inherited assumptions, emotional baggage, and constraints I didn’t choose.
Why Buying Starts to Feel Like the Wrong Kind of Work
At some point, the pattern becomes impossible to ignore.
Every potential acquisition begins to feel less like leverage and more like a deferred cleanup project. No matter how promising the surface metrics look, the underlying reality is the same: before anything meaningful can be built, a significant amount of foundational work has to be done. Systems need to be designed. Data needs to be cleaned. Roles need to be clarified. Processes need to be documented.
In other words, the real work hasn’t been avoided at all. It’s simply been postponed – and made more complex by the fact that none of the original decisions were mine.
That distinction matters.
I don’t mind doing hard work. I don’t even mind doing unglamorous work. What I do mind is spending my time unwinding other people’s accumulated shortcuts before I can apply my own judgment. There’s a subtle but important difference between building something deliberately and inheriting something accidentally.
Buying an existing business promises speed, but what it often delivers is obligation. You inherit not just customers and revenue, but also history – assumptions baked into the product, compromises baked into the org, and decisions that made sense at one moment but no longer do.
The more I think about it, the clearer it becomes that this is not the kind of work I’m actually looking for.
What I want isn’t to retrofit order onto chaos. I want to design order from the beginning. To build systems that reflect how I think, how I like to work, and what I believe actually scales – not just financially, but operationally and psychologically.
Once I see that clearly, the original question starts to shift.
It’s no longer “buy or build” in the abstract.
It’s about what kind of work I want my days filled with.
And the answer isn’t pointing toward acquisition anymore.
Buy vs. Build – Reframed Through Experience
From the outside, the buy-versus-build decision is often framed as a clean trade-off.
Buying is supposed to be faster, safer, and more predictable. Building is supposed to be slower, riskier, and more uncertain. Those distinctions look neat on a whiteboard. They break down quickly once you’re actually in the process.
What buying really offers is immediacy – not simplicity. You step into a business that already exists, but you also step into every unresolved decision that came before you. The past doesn’t disappear just because ownership changes. It shows up in the data, in the team dynamics, in the product architecture, and in the operational habits that have calcified over time.
Building, by contrast, is slower in obvious ways and faster in subtle ones. You don’t inherit momentum, but you also don’t inherit friction. You make fewer decisions, but you make them intentionally. There’s no archaeology phase, no need to decipher why things are the way they are. The structure reflects your judgment from day one.
What surprises me most is how similar the effort curve actually is.
Buying doesn’t eliminate the need to design systems. It just delays it.
Building forces that work upfront – but rewards it later.
Once I see that clearly, the decision becomes less about risk and more about alignment. About whether I want to spend my energy untangling complexity I didn’t create, or shaping something clean from the beginning.
At this point, the answer is no longer theoretical.
I’m not trying to avoid work.
I’m trying to choose the right kind of work.
Why I Decided to Build Instead
By the time I reach this point, the decision no longer feels dramatic.
It feels obvious.
Buying an existing business might make sense for someone looking to deploy capital quickly or assemble a portfolio at scale. It doesn’t make sense for me. Not now. Not in this phase. What I’m after isn’t acceleration for its own sake, but authorship – the ability to design systems intentionally and build businesses that reflect how I actually want to work.
Building my own thing again gives me that.
It allows me to start with clarity rather than compromise, and to apply everything I’ve learned – about structure, discipline, and transferability – from the very beginning. It also lets me avoid recreating the operational sprawl and psychological overhead that tend to accumulate when growth becomes the goal rather than the outcome.
That doesn’t mean I’ll never acquire a business. It means I’m not forcing that path simply because it looks efficient on paper. The structure I’m designing gives me the freedom to build first, learn continuously, and make acquisition a choice rather than a default.
So I stop looking.
I stop taking calls. I stop reviewing decks. And I redirect my energy toward designing a container for the kinds of businesses I actually want to operate – small where they should be small, scalable where it matters, and built from the ground up with leverage in mind.
That decision doesn’t come with a detailed roadmap yet. It doesn’t need one.
What it comes with is conviction – not the loud kind, but the quiet kind that makes it easy to move forward.
Either way, wish me luck!
Thomas Michael
CEO
Tomco Capital Corporation
