As a reminder, each Transaction Debrief breaks down a real deal, what the business looked like going in, what drove the valuation, and what the owner did (or didn't do) that shaped the outcome. Think of it as the comp sheet for your future exit.

I came across a deal recently that's worth breaking down, not because it's a unicorn story, but because the mistakes the original owner made (and the moves the buyers made) are patterns I see constantly in the lower middle market.

Here's the short version.

A founder had built a B2B SaaS product over five or six years. Solid enterprise customers. Real revenue. But he was running it as a side project alongside his services business. Growth was flat. He was pricing 5–10x below market just to collect logos. No sales team, no customer success function, and engineering resources were borrowed from his other company.

He tried to sell. Shopped it for about 12 months. Buyers did diligence and walked.

A group of experienced operators saw the opportunity, acquired it, and within 36 months flipped it to a major strategic acquirer for 9 figures.

Same product. Same market. Completely different outcome.

Here's what they actually did and why it matters if you're running a business today.

They built a sales engine the founder never did.

The original owner was a classic solo-salesperson founder. The buyers had previously built and run a 30-person inside sales org across 13 offices. They stood up a full go-to-market operation.

Their philosophy was simple: if you're not building pipeline, nothing else matters.

Most owners I talk to have a version of this gap. The business runs on the founder's relationships and reputation. That works until you want to exit because a buyer isn't paying for your Rolodex. They're paying for a system that works without you.

They turned customer success into a revenue engine.

There was no formal CS function before the acquisition. The new operators built one and used it to expand within existing accounts. One customer went from a single-division deployment to a global rollout. That kind of expansion revenue is what gets you noticed by strategic acquirers.

If your current customers are on autopilot, you're sitting on your most underleveraged asset. Expansion revenue doesn't just improve your top line, it changes the multiple an acquirer is willing to pay.

They raised their prices immediately.

The original owner had been charging $25K per customer. The buyers moved the floor to $125–250K on day one.

Underpricing isn't a growth strategy. It's a signal to acquirers that you don't believe your product is worth much. If your best customers would pay 3–5x what you're charging and you haven't tested it, you're leaving value (and money) on the table every single month.

They positioned for the exit from the start.

The buyers knew who the most likely acquirer was going to be and invested deliberately in that relationship with executive access, ecosystem visibility, and strategic co-selling. When their product beat the acquirer's own competing solution in a head-to-head evaluation, the acquisition conversation started for real.

You don't have to know your exact buyer today. But you should be building the kind of business that the logical acquirers in your space can't ignore. That means understanding who they are, what they value, and making sure you show up on their radar before you're ready to sell.

The messy part nobody talks about.

When the strategic offer came in, the company's institutional investor tried to block the deal. They offered more money and threatened litigation. The founders chose the clean exit anyway with no earnout, employees landing at a world-class organization, and a return they could lock in now instead of grinding for years under a financial sponsor playing with house money.

Know your number before someone else's incentives override yours. A PE firm optimizing for a 10x fund return and a founder optimizing for a life-changing exit are playing two completely different games. Neither is wrong but you have to decide which one you're in before you're sitting at the table.

The bottom line:

The product didn't change. The market didn't change. What changed was the operating infrastructure around it such as GTM, pricing, customer expansion, and strategic positioning. That's what turned a $2M side project into a 9-figure outcome.

Most of the owners I work with aren't sitting on bad businesses. They're sitting on underleveraged ones. The gap between what you've built and what an acquirer would pay for it is almost always an operations gap, not a product gap.

Inspired by a episode of Built to Sell Radio, hosted by John Warrillow. If you're thinking about exits, it's one of the best podcasts in the space. Worth a listen.

In next week’s email, we’ll be going over another interesting transaction debrief to help you learn how the best operators are positioning their businesses for a maximum valuation.

To your future exit,

Andrew,

Unlock Your Exit Team