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The $10M Mistake 90% of Founders Make Right Before Selling Their Business
Wall Street Buyers Have a Playbook to Lowball You. This Is Page One.
TL;DR: At exit stage, buyers are not paying for upside stories, they’re pricing risk they can’t explain away. Most value erosion comes from unresolved fears around concentration, cash timing, working capital, and structural ambiguity. Founders who prepare by removing these fears early don’t just avoid retrades; they create momentum, preserve certainty, and often realize higher net proceeds without chasing additional growth.
Exit Value Isn’t Created by Growth. It’s Created by Removing Fear.
Most founders believe exit value is built by adding something.
More growth.
More customers.
More revenue.
More story.
That belief is understandable. It’s also wrong at the stage where most serious exits actually happen.
In the final 6 to 12 months before a transaction, buyers are rarely looking for upside to believe in. They are looking for risk they can’t explain away. And every unexplained risk becomes a discount, a delay, or a retrade.
The uncomfortable truth is this:
At exit stage, removing buyer fear is often worth more than adding growth.
And the founders who understand that early don’t scramble when diligence starts. They control it.
Where Buyers Quietly Apply Discounts
Buyers almost never say, “We’re discounting you because we’re nervous.”
They say things like, “We need to normalize this.” or “We’ll address that in confirmatory diligence.” and “Let’s talk about structure instead of price.”.
What they really mean is: there’s something here we don’t fully trust.
Customer concentration is one of the fastest examples. If your top few customers represent an outsized share of revenue, buyers don’t need churn to penalize you. The risk alone is enough. That penalty doesn’t disappear when you explain it. It disappears when the exposure is diluted, even modestly.
The same dynamic shows up with carve-out risk, even in businesses that are never intended to be carved out. Buyers worry about what isn’t clean, what is shared, and what would be painful to unwind. If those answers aren’t already documented, the fear becomes structural.
Exit value erodes not because the business is weak, but because the buyer can’t prove to themselves that it’s strong.
Why Quality of Earnings Becomes the Battleground
Most retrades happen late, not because the numbers were wrong, but because the interpretation of those numbers changed.
Revenue timing is a classic example. If bookings, billings, and revenue recognition don’t reconcile cleanly, buyers assume they’re looking at pull-forwards, not performance. Even if the economics are solid, ambiguity gives them leverage.
Support costs tell a similar story. Buyers don’t just care what support costs are. They care whether those costs are reactive or proactive, rising or stabilizing, predictable or chaotic. A business with flat revenue and improving support efficiency often feels safer than a faster-growing business with rising reactive load.
Even reserves can work against you. Over-reserving may feel conservative, but at exit it quietly depresses EBITDA and invites debates about “true earnings power.”
At this stage, the game is no longer about optimism. It’s about eliminating interpretive ambiguity.
Working Capital Is Where Deals Get Emotional
Few things sour a deal faster than a working capital dispute.
Founders often assume this is mechanical. It isn’t. It’s psychological.
Trailing-month pegs feel arbitrary to sellers and opportunistic to buyers. Median-based pegs grounded in seasonality feel defensible to both sides. The difference is math, but the outcome is trust.
The same applies to accruals. Stale or inconsistent accruals signal sloppiness, even when they don’t materially change cash. Cleaning them up early removes a reason for buyers to hesitate or reopen discussions.
When working capital is clean and well-documented, buyers stop negotiating with emotion and start negotiating with logic. That alone can preserve seven figures.
Why Some Buyers “Can’t Say No”
Not all buyers stretch, the right buyers stretch.
The ones who stretch are those for whom your business solves a near-term problem they already have. A revenue mix they need to rebalance. A geography they need to enter. A regulatory shortcut they can’t build fast enough.
Timing matters more than founders realize. Strategic buyers are most flexible when guidance pressure is real, not theoretical. Approaching them when they are about to report or revise expectations changes the conversation entirely.
This is not manipulation. It’s understanding who has urgency and why. Deals feel easier when the pressure is on the other side.
Why Data Rooms Kill or Save Momentum
Most sellers think data rooms are about completeness.
They’re not. They’re about eliminating unknowns that trigger fear.
Buyers get nervous when they can’t answer basic questions quickly. How pricing has moved historically. Whether customers accepted increases. How pipeline quality varies by rep. Whether security incidents have occurred, even minor ones.
Providing this information upfront does something subtle but powerful. It shifts the buyer from detective mode into confirmation mode. That shift is often the difference between a smooth close and a grinding renegotiation.
Momentum is fragile. Fear kills it faster than bad numbers ever will.
Structure Is Where Real Money Is Made or Lost
At the final stage, many founders focus entirely on headline price.
That’s a mistake.
Small structural decisions often matter more than the number. Seller notes priced intelligently can bridge valuation gaps without introducing earn-out risk. Indemnity baskets and survival periods determine how much cash you actually keep and how long it’s tied up.
Two deals with the same headline price can produce radically different outcomes for the seller. One closes cleanly. The other drags on for years through escrow, disputes, and delayed releases.
Structure determines which one you’re in.
The Through-Line Most Founders Miss
Across hundreds of exits, one pattern repeats.
The founders who win don’t try to make buyers excited. They try to make buyers comfortable.
Comfort accelerates diligence.
Comfort reduces retrades.
Comfort improves terms.
Comfort preserves momentum.
And comfort is created by preparation, not persuasion.
What to Do in the Next 60 to 180 Days
If you are within a year of a potential transaction, your highest-leverage move is not chasing growth.
It is systematically removing the reasons buyers hesitate.
That means diluting concentration risk, even slightly. Cleaning up carve-out assumptions before anyone asks. Making revenue timing and support economics painfully clear. Normalizing working capital with defensible math. Mapping buyers who have real urgency. And structuring the deal so you keep more of what you earn, sooner.
You don’t need to do everything. You need to remove enough fear that the buyer stops negotiating defensively.
That’s when value shows up. At exit stage, growth is a bonus and certainty is the product.
Founders who understand that stop trying to impress buyers and start making them comfortable. The irony is that comfort is exactly what buyers pay a premium for.
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