The best exits are timed, not lucky. The window is usually visible in your trailing 12 months before it shows up in your feelings.
Key Takeaway: If your trailing 12 months is the best in three years and you’re at least 18 months away from a known disruption, you may be in a sell window right now.
It was a Tuesday in July. The owner was alone in the office before anyone showed up. Not the loud office. The quiet one. Coffee, fluorescent lights, the faint hum of the printer warming up.
He had his trailing 12 months open on the screen. Revenue was up. Margin was up. Cash was steady. Nothing looked dramatic. That was the point. It looked calm.
His phone buzzed with a broker’s name he had ignored twice already. He stared at it long enough to feel his own resistance form.
Not yet. We are not ready. We can do one more year.
Then he did what owners rarely do when they are busy. He pulled up the last three years of profit and loss and looked at the numbers like a buyer would.
This year was the best of the three. Not by a little. By enough to matter.
The broker call was not the decision. The numbers were.
He picked up the phone. They started in July. Signed a letter of intent in December. Closed in March.
From the outside, it looked like lucky timing. It was not.
Most owners don’t miss the window because they’re lazy. They miss it because they tell themselves they’re being responsible. This post is how to see the window while you’re still in it.
Reality
Buyers do not pay premium multiples for complicated stories. They pay for stories that are easy to underwrite:
Most owners miss their best window because they wait until they feel done. By then, the strongest twelve months has already rolled off and the story is harder to tell.
Fix It
Ask one question:
If a buyer asked why the last twelve months was your best, could you answer in three sentences without apologizing?
If the answer is no, you do not have a timing problem yet. You have a clarity problem.
This is where the Exit Stack matters:
Pro Move
Write your buyer story in exactly three sentences:
If you cannot write those three sentences cleanly, the market is not your constraint. Your story is.
Quick Win (solo, under 20 minutes)
Pull your last three years of profit and loss. Circle your trailing 12 months.
Ask:
Is this year tracking to be your best?
If yes, your sell window may be twelve to eighteen months away. That means the right time to start is earlier than your emotions want it to be.
Reality
Most owners think the calendar starts when they decide to sell. The calendar actually starts when the business becomes easiest to underwrite.
A real process takes time. It is preparation, buyer conversations, a letter of intent, diligence, and closing. You do not need to forecast macro perfectly. You do need runway.
The owners who get the best outcomes align two clocks:
Fix It
If your trailing 12 months is strong, treat time as an asset, not a threat. Waiting until you are emotionally done turns the process into a sprint. Sprints create mistakes. Mistakes create structure that punishes you.
If a buyer tries to set the pace for you, read Am I Being Rushed and Lowballed? before you answer.
Pro Move
Treat your best trailing 12 months like fresh concrete. It sets whether you touch it or not.
Circle your strongest trailing 12 months. That’s the mix buyers will pay for. Then back into a close date and start earlier than feels comfortable, because comfort is how owners miss the window.
You don’t get paid for being tired. You get paid for being undeniable.
Quick Win (solo, under 15 minutes)
Block three recurring windows for the next eight weeks:
If you cannot protect those blocks, you are not ready to run a process even if the business is strong.
Reality
Owners time exits off feelings. Buyers time offers off underwriting. This checklist forces you onto underwriting logic.
Fix It
Answer the three questions:
A) Trailing 12 months strength
Is your trailing 12 months the strongest in the last three years?
B) Disruption distance
Are you at least 18 months away from a known disruption?
Known disruptions are not theoretical. They are calendar items:
C) Process readiness
Are you emotionally ready for a six to twelve month process that includes scrutiny, delays, and negotiation?
If C is weak, that is usually burnout, not timing. Start by reading How Do I Exit Without Burning Out?
Pro Move
Here is what it looks like when the checklist outputs Wait even though the numbers look great.
Example shop
On paper, this looks like Go. Now apply the checklist.
A) TTM strength: Yes
Strongest in three years. Margin expanding.
B) Disruption distance: No
Top customer contract renews in 14 months. That’s inside the 18-month window.
C) Process readiness: Yes
Owner is calm. Can hold a six to twelve month process.
Output: Wait or Not Yet, depending on how controllable the disruption is.
If the contract renewal is a coin flip, it is Not Yet. If you have a strong renewal history and a plan to diversify further, it can be Wait with a clear project list.
Great numbers do not always mean sell now. Sometimes they mean protect the next twelve months and start preparing.
Quick Win (solo, under 10 minutes)
Write your output: Go, Wait, or Not Yet. Then write one sentence:
“What has to be true for this to become Go?”
That is your 90-day plan.
Reality
Buyers don’t pay for today’s number. They pay for a direction they believe will hold after you’re gone.
That direction shows up in three places on your financials, and each one has a way owners accidentally talk themselves out of a premium multiple.
Fix It
Track these annually and look at the trend, not the point.
A) Revenue trend
Owners celebrate top-line growth. Buyers ask what it cost. The warning sign isn’t that revenue is up. The warning sign is when revenue is up and the business quietly got harder to run.
That shows up on the P&L like this:
Buyers see that and think: “They bought growth with margin.” That is not a premium story. That is a risk story.
B) EBITDA margin trend
Owners remember the jobs that went wrong. Buyers remember whether margin expands or compresses. Expanding margin tells a buyer you have control. Compressing margin tells them you’re fighting your own operation.
The P&L version is subtle:
Owners call it noise. Buyers call it drift. Drift is what kills the best time to sell window. Not a dramatic collapse. A slow, believable decline.
C) Customer concentration direction
Owners get comfortable with one big relationship. Buyers get nervous. Concentration doesn’t show up as a line item. It shows up as a question the buyer asks twice, two different ways:
“What happens if they leave?”
If your top customer went from 28% to 19% over the last year, that is a sellable story. It means you’re reducing single-point risk. If your top customer went from 19% to 28%, you might be having your best year and still be getting closer to a discount.
If you’re not sure whether the stall is you or the business, read What's Really Stalling My Exit: Me or The Business? before you decide you’re waiting for the market.
Pro Move
Pick one lever that is currently helping your story and protect it like you would protect your best tech. Then pick one lever that is drifting and fix it before it turns into a buyer excuse.
That is timing strategy.
Quick Win (solo, under 25 minutes)
Open your last three years and write three arrows:
Now write one sentence:
“The arrow that will move my multiple most is ___ because ___.”
That sentence tells you whether this is a Go window, a Wait window, or a Not Yet window.
Reality
Many owners start a process when they are tired. That is when they are most vulnerable to:
This is why the best exits look obvious in hindsight. Owners miss the clean window because the clean window doesn’t feel urgent. Exhaustion does.
Fix It
If you’re tempted to sell because you’re tired, stabilize first.
Pro Move
If your checklist output is Wait, use the wait.
Don’t sit still. Use that period to make the next trailing 12 months clean:
That is how you arrive at Go with leverage instead of arriving at Go with panic.
Quick Win (solo, under 15 minutes)
Write down two sentences:
If you can’t answer, you’re not timing. You’re drifting.
The July morning wasn’t dramatic. That’s why it mattered.
The owner sat under fluorescent lights with a coffee that had gone lukewarm and a three-year P&L open on his screen. No music. No pep talk. Just numbers.
He saw the strongest trailing 12 months. He saw the next disruption far enough away to run a real process. He saw that he still had the energy to make decisions well.
Then he did the hardest part. He started before he felt like he had to.
Most owners only see that window in the rearview mirror. The best ones recognize it while they’re still sitting in it.
If your trailing 12 months is your best in three years and the next 18 months is clear, you may not be past it. You may be standing in it.
When you want a custom exit play built around your numbers, timing, and goals, that is what the Exit Workplan is for. For a quick gut check on your business, run the Buyout Potential Scorecard to gauge whether or not now is good time to sell.
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