The Business Was Built to Run, Not to Evolve

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Hey, it’s David

Welcome back to M&A from the Plane, quick stories and insights drawn from the many miles I log in the air talking to business owners, founders, and dealmakers.

A few months back, I reviewed a company that, on paper, looked like it had everything lined up…
Strong revenue, recurring contracts, a solid team, and decent margins.

But the deeper we got into diligence, the more one thing stood out:

This business wasn’t learning.

Data wasn’t being collected, systems weren’t talking to each other, and decisions were still being made by gut feel, even when signals suggested otherwise.

It wasn’t broken.
But it wasn’t evolving either.

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The Flight Was on Time… Until We Sat on the Tarmac for an Hour

Everything looked good.
On-time departure... Smooth boarding… Luggage loaded… Crew ready.

Then we stopped.
We sat.
No updates… No movement…

Just a delay caused by something behind the scenes we couldn’t see.

That’s what this particular business felt like.
From the outside, it looked flight-ready. But inside, the systems weren’t coordinated.
In essence, the “business machine” wasn’t talking to itself.

There was no obvious “broken” part, yet there was no momentum either.

Here’s what started to show up the deeper we got:

• They had metrics… but only after the fact. No real-time visibility, no way to course-correct in motion.

• Teams were operating in silos. Sales had their system, finance had theirs, ops was doing something entirely different.

• Decisions were still coming from gut feel - not from a feedback loop that actually learned from past performance.

• And everywhere we looked, there were manual workarounds. People were filling the gaps the systems should’ve been solving.

These aren’t surface-level issues. They’re structural.
And they show up post-close… when it's expensive.

The Thought of the Day

At some point, every business lands in one of two camps:

1. The kind that can move! They have good people, decent structure, and they get the job done

2. The kind that actually learns …and gets better every time it does!

That second kind?
It’s not just faster. It’s safer to buy. It handles change without spinning out.

And in today’s market, that kind of business gets rewarded… because buyers know it won’t stall when things shift.

Final Thought
You don’t need to be a tech company to think like one.
You just need to wire your business to learn from what it does every day.

If you’re preparing for a future exit, ask yourself:
Is your company just operating… or is it getting smarter as it runs?

If you’re not sure, that’s a signal worth exploring.

Let’s talk.

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Thank you!

David