Most business owners assume that when it’s time to sell, the numbers will speak for themselves. But in lower middle market and main street deals, it’s not just what your financials say—it’s how cleanly and credibly you say it.
At High Point Advisory Group, we’ve seen countless sellers leave money on the table simply because their financials weren’t packaged in a way buyers and lenders could trust. And we would know—we support a high volume of buy-side diligence projects, so we’re trained to spot every crack, inconsistency, and risk buyers will use to chip away at your valuation.
This post breaks down the three most common financial issues we uncover when helping sellers prepare for exit. These problems don’t just make diligence harder—they actively reduce your enterprise value. The good news? If you catch them early, they’re fixable.
Most brokers and sellers talk in terms of SDE or EBITDA multiples. And yes, those are foundational metrics. But here’s what too many people miss: the quality of your earnings drives the strength of your multiple.
A business with $1M in clean, well-documented EBITDA may sell for 5–6x. But a business with the same $1M in EBITDA, masked by messy books, missing documentation, and unclear adjustments? It might sell for 3–4x—or not close at all.
Buyers don’t pay top dollar for potential. They pay for confidence. If your financials raise questions, delay responses, or fail to tie back to reality, they’ll assume the worst and reprice accordingly.
We regularly see sellers present financials that show the wrong picture—not because they’re trying to deceive anyone, but because their books simply weren’t maintained with an exit in mind.
This typically shows up in three ways:
Many business owners legitimately run personal or hybrid expenses through the business: vehicle costs, travel, meals, family payroll, even home utilities. That’s fine—until it’s time to sell.
The problem? Buyers don’t take your word for what’s an add-back. They want proof. If your books don’t clearly document these items, expect pushback.
What buyers flag:
What we do:
We work backwards through 1–3 years of financials, creating an add-back schedule that can be justified and verified. We highlight these in your seller package so you’re not negotiating on defense.
If you record revenue when cash hits your account—regardless of when work is performed—you’re on the cash basis. Many small businesses operate this way, but it causes problems when:
What buyers flag:
What we do:
We adjust your income statements to reflect revenue earned—not just received. We may recommend shifting to accrual accounting or, at minimum, clarifying recognition policies during the sale process.
This is a huge trust breaker. If your P&Ls say you made $800K in SDE but your tax returns only show $500K, you’ll need a bulletproof explanation—or the deal will stall.
Buyers use third-party advisors (like us) to verify your numbers through Proof of Cash—a reconciliation of your bank activity against reported income.
What we do:
We run a Proof of Cash ourselves before a buyer ever sees your business. We proactively find discrepancies, resolve missing entries, and make sure that what’s in the P&L matches what’s actually in the bank.
Most sellers don’t realize that working capital can be a silent deal killer. Here’s how it works:
Buyers assume they’re buying a business that can continue operating without needing an immediate cash injection. That means there needs to be enough receivables, inventory, and payables on Day 1 to support operations.
But if your working capital is mismanaged—or misrepresented—buyers will:
Are there invoices that are 90+ days old and probably won’t be paid? If they’re still on the books, you’re overstating your assets and working capital.
If your inventory hasn’t turned in 12+ months, it may be obsolete. Buyers won’t value it at cost—and neither should you.
Some sellers delay recording liabilities until year-end or lump credit card charges into a catch-all account. This creates a false impression of cash flow.
What we do:
We normalize working capital by:
This protects your valuation—and helps avoid painful post-close reconciliations.
One of the biggest drivers of perceived risk is when the business is too dependent on the owner—or when the team structure is unclear. Buyers don’t just want a set of financials. They want a business that runs.
If you’re the head of sales, the production lead, the bookkeeper, and the operations manager—all in one—buyers will wonder what’s left when you’re gone.
Even if you plan to stay on for a transition period, a buyer doesn’t want to be dependent on you long-term. The more institutionalized your team and systems are, the more valuable the business becomes.
We understand why many business owners have structured payroll the way they have—especially in founder-led or family-run companies. Maybe you’ve used 1099 contractors instead of W-2 employees to stay flexible. Maybe your spouse or kids are on payroll for tax efficiency. Maybe you’ve paid yourself primarily through draws or distributions. That’s all perfectly normal in the day-to-day reality of running a small business.
But when it’s time to sell, those same practices can muddy the waters.
Buyers will want to see a clear and consistent payroll structure that reflects what it would cost them to operate the business without you. If compensation is split between multiple accounts, off-books, or includes non-operational family members, it becomes hard to model—and that introduces risk.
What buyers worry about:
What we do:
We help untangle the reality from the reporting. That means:
You don’t need to change your structure overnight—but you do need to help buyers see through it. That’s where we come in. We make your payroll understandable, justifiable, and most importantly—not a reason to lower your valuation.
Each of these financial issues—messy P&Ls, working capital traps, and owner-dependence—can reduce enterprise value by hundreds of thousands of dollars. They also increase the likelihood of:
The fix? Start early and work with an advisor who knows how buyers think—because we are the team buyers hire when it’s their money on the line.
If you’re 6–24 months out from a potential sale, now is the time to get your financials ready for prime time. At High Point, we support sellers with:
Want to see how we’ve helped other sellers protect their valuation? Check out:
We’ll help you think like a buyer—before a buyer tells you what your business is worth.