This is not working

I’m taking calls with founders who want to sell their businesses.

On paper, this feels like the logical next step. I’ve just exited my own company. I have capital. I have experience. Acquiring an existing business should be faster than starting from scratch. Less risk. Less friction. A shortcut, at least in theory.

So I say yes to conversations.

At first, they’re polite. Optimistic. Everyone tells a version of the same story: the business is “doing well,” there’s “strong demand,” and they’re “ready for the next chapter.” I’ve heard these phrases before. I used them myself, once.

Then the questions start.

And that’s when things begin to unravel.

Simple things are missing. Financials that should exist don’t, or exist only in fragments. Numbers don’t reconcile. Revenue figures shift depending on how they’re explained. Basic metrics – customer counts, churn, margins – are answered vaguely, if at all.

I ask how the business actually runs day to day.

There are no written processes. No documented workflows. No clear ownership of roles. Job descriptions, if they exist, live in someone’s head. Customer lists are outdated or incomplete. There’s no real CRM – just inboxes, spreadsheets, and memory. Contracts are scattered, some signed, some unsigned, some “standard,” others improvised.

What I’m looking at isn’t a company ready for transition.
It’s a collection of habits held together by the founder’s presence.

And suddenly it’s obvious: this isn’t diligence yet.
This is archaeology.

The Reaction I Didn’t Expect to Have

What surprises me most is not the mess itself.

It’s how viscerally I react to it.

I’ve just come out of a full due diligence process on my own company – actually, two of them, but that’s for another blog post – so I know exactly what this looks like when it’s done properly. I know how invasive the questions get. I know how unforgiving the numbers are. I know how quickly vague answers get exposed.

So when I’m met with hand-waving, half-formed explanations, and an almost casual relationship with reality, something in me tightens.

At first it’s disbelief.
Then frustration.
Then a kind of dark, almost incredulous amusement.

How does someone expect to sell a business like this?

Not in theory. In practice. To whom?

Because what I’m being shown isn’t an asset ready to change hands. It’s a dependency disguised as a company. A fragile system held together by personal heroics, informal agreements, and the founder’s daily involvement.

I don’t feel excited.
I feel like running for the hills.

And I realize something uncomfortable: I don’t want to inherit someone else’s chaos.

Why This Isn’t Sellable – At Least Not to Anyone Serious

Stripped of optimism and storytelling, most of these businesses share the same underlying problem.

They are not designed to exist without the founder.

There are no clean financial statements that reconcile month to month. No consistent definitions of revenue, margin, or profit. The numbers don’t tell a coherent story because no one ever needed them to – as long as cash kept coming in.

Operations live in people’s heads instead of on paper. There are no standard operating procedures. No documented workflows. No clear handoff points. Knowledge is tribal, not transferable.

Customers are real, but the data isn’t. Lists are outdated. Contracts are inconsistent. Terms vary by relationship. Renewal logic is informal. There’s no single source of truth.

Sales happens, but there’s no system behind it. No CRM. No pipeline discipline. No way to forecast anything beyond hope.

In short, these are not businesses you acquire – they are problems you absorb.

Someone might buy them, of course. But only one of two people:

A strategic buyer willing to rebuild everything from scratch.
Or a sucker who mistakes revenue for readiness.

I’m neither.

And the more of these calls I take, the clearer it becomes: buying a company like this doesn’t save time. It just delays the inevitable rebuild – with more risk, more resentment, and less freedom.

Which leads me to a conclusion I’m not yet fully ready to articulate, but can’t ignore:

If I’m going to clean up a mess anyway, it might as well be my own.

A Pattern Starts to Emerge

After enough of these conversations, it stops feeling coincidental.

Different founders. Different industries. Different personal stories. And yet, beneath the surface, the same structural weaknesses keep appearing. Not because these founders are careless or incapable, but because their businesses were never designed with transferability in mind.

They built companies to function, not to be inspected.

In almost every case, the focus was on forward motion: shipping product, closing customers, solving the next urgent problem. Processes evolved organically. Decisions accumulated informally. Knowledge lived in people’s heads rather than in systems. As long as the founder remained at the center, everything worked well enough.

Until someone like me enters the picture and starts asking questions that aren’t about survival, but about continuity.

Questions about financials that should reconcile across periods.
Questions about how work actually flows through the organization.
Questions about ownership, systems, processes, accountability, and repeatability.

And what becomes clear, again and again, is that the business doesn’t truly exist independently of the founder. It operates because the founder remembers, corrects, intervenes, and improvises. Remove that presence, and the structure starts to wobble.

This isn’t incompetence. It’s misalignment.

The founders I’m speaking with want liquidity, optionality, or an exit – but they’ve never been forced to think about their companies as transferable assets rather than personal vehicles. Running a business and preparing one for transition are related, but they are not the same discipline.

As this realization settles in, something shifts for me.

If this many capable, driven founders are this underprepared for scrutiny, then what I’m seeing isn’t a series of isolated issues. It’s a systemic gap between how businesses are built and how they are eventually sold.

I don’t yet know what to do with that insight. I’m not turning it into a plan or a product. I’m simply registering it, repeatedly, as it shows up across conversation after conversation.

Something here isn’t working.

I don’t draw a conclusion yet. I’m not ready to. All I know is that the acquisition path I thought might make sense feels increasingly misaligned with how I actually want to spend my time and energy. Buying someone else’s unfinished systems, no matter how well intentioned the founder, doesn’t feel like leverage. It feels like inheriting responsibility without conviction.

So for now, I stop taking calls. I pause the search. And I sit with the discomfort of a realization that hasn’t fully formed yet – but is becoming harder to ignore.

Cheers,

Thomas