Last weekend, I assembled a propane fire pit. Even with step-by-step instructions, it took longer than I expected. I pre-watched an assembly video. I second-guessed a few steps. At one point, I realized I’d skipped ahead and had to undo my work.
I learned a lot in the process.
The problem is, I’ll probably never assemble another fire pit again. Or if I do, it’ll be years from now—and whatever I learned will be long forgotten.
That same weekend, I bought two identical bookcases. I tend to read digitally—but some books work best in print, like books about design and art history. As a result, I keep buying bookcases.
Assembling the first bookcase took time. The second one went together much faster. Not because the second was simpler—but because I knew what to expect. I knew which steps mattered most, which warnings in the instructions were overly cautious, and where rushing would come back to bite me.
Same goal. Same parts. Same tools. Very different experience.
Experience compounds—when you get to repeat the work
This “practice makes perfect” pattern shows up everywhere. The second presentation is better than the first. The second negotiation is calmer. The second time you hire for a role, you ask better questions.
Repetition creates judgment. Judgment creates speed. Speed creates confidence.
But here’s the catch: most of the things that matter most in business only happen once. Most agency owners:
- Start one agency
- Grow one agency
- Attempt to sell one agency
For most agency owners, the exit is a one-time event. And that’s exactly what makes it precarious. When you want or need to sell, you need to get it right.
But what about exceptions?
Yes, there are plentiful exceptions.
- I’ve had former clients return for advice after they exit and then launch a new agency—and I’m running my third business in three decades.
- If you sell to an investor-backed rollup that wants to exit at a higher multiple, you may get a “second bite of the apple.”
But when it comes to guaranteed money changing hands, you have just one chance to get it right—the “cash down” terms you negotiate when you sell your current agency.
If you don’t get offers—or you don’t like the offers—you have to go on the market again, and hope things improve in the future. I’ve helped clients do that—like a client who accepted an eight-figure offer after previously declining several smaller ones. Yet the exit itself was still a single transaction. If they had to sell the first time, they’d have missed out on millions of dollars.
Most agency owners don’t get that real-world practice, which leaves them at the mercy of acquirers seeking the best possible deal.
Knowing the theory isn’t the same as doing the work
You can read books about selling an agency. You can attend panels and webinars. You can talk to peers who’ve been through it. You can do my on-demand training: Control (and Maximize) Your Agency Exit.
All of that helps—but it’s not the same as doing it.
Airline pilots don’t train by reading manuals and then hopping into a real plane with real passengers. They train first in simulators. They practice handling emergencies and other surprises. They make mistakes safely. They learn how it feels when something goes wrong.
Because when it’s real, there’s no “rewind” button.
Selling your agency works the same way. When buyers show up, you don’t get a practice run. You won’t get to redo:
- How your financials are structured
- How dependent the business is on you
- How concentrated your client base looks under scrutiny
- How clean (or messy) your operations appear in diligence
Those things either help you—or they quietly get used against you.
And most owners don’t realize where they stand until the buyer’s diligence team points it out, usually right before trying to lower the valuation or shift the terms.
The cost of “learning on the job”
Acquirers do this for a living—or at least, they’ve explored agencies to buy longer than you’ve explored selling your one agency. Some have even seen hundreds of agencies. Buyers know exactly where to look for risk, or they’ve hired someone to do that for them.
Agency owners, by contrast, are often experiencing this process for the first—and only—time. That asymmetry matters.
It’s why deals fall apart late. It’s why owners feel blindsided by valuation cuts compared to the initial LOI offer. It’s why earn-outs end up far riskier than expected.
The issue usually isn’t that the agency is “bad.” It’s that the owner didn’t know what buyers would care about until it was too late to fix it. The buyer was ready—but the seller wasn’t.
What if you could simulate selling your agency?
That’s the idea behind my Exit-Readiness Audit. Instead of waiting for buyers to examine your agency, I review it first—from the perspective of someone who might acquire it, and who’s seen inside hundreds of agencies worldwide.
Within your agency, I look at:
- What will hold up in due diligence
- What will raise questions
- What strengthens valuation
- What quietly undermines it
But there’s a critical difference between this and buyer diligence: I’m on your side.
In contrast, a buyer’s diligence team is paid to:
- Find risk
- Reduce valuation
- Shift deal terms in the buyer’s favor
My job is the opposite. I’m focused on helping you:
- See what a buyer will see before they see it
- Make better decisions while you still have leverage
- Avoid “learning moments” that cost real money
You get the benefit of selling your agency a “second time”—without picking up the real-world scars.
Seemingly small choices can have a big impact. A client was speaking with several potential acquirers. They asked me if they could skip sharing finances from three years ago, because it was a down year. I advised them to share all three years—because savvy acquirers will want that anyway. And if they didn’t pre-disclose the down year, it’ll look like they were trying to hide something.
When you don’t have plans to sell
One common misconception is that exit planning is only relevant when you’re ready to sell.
In reality, the best exits are built years in advance.
An Exit-Readiness Audit isn’t about pushing you toward a transaction. It’s about understanding how your agency would be perceived if a buyer showed up—and what you can do now to improve that outcome over time.
By committing to improvement now, you can build an agency that’s smoother and more lucrative to operate—which gives you more options for the future.
Some owners use this insight to:
- Reduce personal risk
- Improve profitability
- Strengthen leadership depth
- Create optionality—even if they never sell
Others use it to prepare intentionally for a future exit, rather than hoping things “work out” when the time comes.
Don’t treat a once-in-a-career event like a one-off project
If you plan to build and sell agencies repeatedly, you might not need an exit advisor the third or fourth time you do it.
But if your current agency matters—if the outcome of the exit will shape your financial future—then leaving it to chance is a costly gamble.
You wouldn’t “assemble” your most important investment with half-read instructions and hope for the best. You don’t have to do that with your agency either.
If you want to understand how buyers would view your business—and how to improve your position while you still can—let’s talk.
Question: Where have you learned from others’ mistakes?
