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Pillar guide

Deal structures beyond the all-cash offer

Very few businesses sell for all cash on day one. Earnouts, seller notes, and the rest of the terms decide what you really take home.

15 min readUpdated May 20266 guides in this pillar

Somewhere in your sale, a buyer will slide a number across the table, and everything in you will want to compare it to the number in your head. Resist that for one beat, and ask the better question: how much of it arrives, when, and what has to go right first? The offer is not the number. The structure is the number.

Very few small businesses sell for all cash on the day of closing. The typical Main Street deal is a stack: a bank loan for most of it, the buyer's down payment, often a seller note, sometimes a consulting agreement, occasionally a contingent piece riding on how the business performs after you leave. Two offers with the same headline can differ by six figures in what the seller actually banks, and the difference lives entirely in terms most sellers meet for the first time mid-negotiation, at the exact moment they are least equipped to study them.

This pillar is the study session, held early, before there is a buyer across the table. It covers the five structural decisions that shape every deal, each with a full guide behind it. And it carries one theme you will not find in most deal-structure writing, because most of it is written for buyers or for bigger deals: on Main Street, the SBA is the invisible party to your negotiation. Most sub-$5 million buyers finance through an SBA 7(a) loan, and the SBA's rulebook quietly forbids or reshapes half the structures sellers read about elsewhere. A term that cannot finance is not a term; it is a delay with your business off the market. Every guide in this pillar answers the same two questions: what is this structure, and what does the SBA do to it?

One standing caveat for the whole pillar. Deal structure is where the sale gets closest to law and tax, and these guides are education, not advice. The pattern that serves sellers well is to learn the landscape here, then bring in a deal attorney and a CPA before terms go on paper. At Main Street scale, that costs hours of professional time and routinely pays for itself many times over.

The stack, and who carries the risk

Picture a $1.5 million deal the way the money actually moves. The buyer brings roughly $150,000 of their own, ten percent, the SBA's minimum injection. A bank funds most of the rest across a ten-year loan. If the pieces do not quite reach, you carry a seller note for the gap, paid over years, subordinate to the bank. Maybe a slice rides on a contingent structure. Maybe a consulting agreement pays you for twelve months of transition work.

Now read the same stack as a risk map. The bank is paid first and holds the collateral. The buyer risks their down payment. And every dollar of yours that is deferred, in a note, a contingent structure, an escrow, is a dollar still exposed to a business you no longer control. That is the seller's master key to this whole pillar: structure is the art of deciding which dollars are certain and which are hopeful, and pricing the hopeful ones honestly. A smaller number that is all cash and closes can beat a bigger number assembled from promises.

The five decisions

The seller note. The workhorse. Most Main Street deals include seller financing, and the 2025 rules made its terms sharper: a note counted toward the buyer's down payment now sits on full standby for the life of the loan. When to carry one, how to secure it, and what standby really means for when you see the money: our guide on seller financing is the foundation the rest of this pillar builds on.

The contingent piece. Buyers bridge valuation gaps with performance-based payments, and here the SBA's hand is heaviest: earnouts are prohibited in 7(a) deals outright. What survives is a precise substitute, the seller note with fixed principal whose terms flex against the business's own history, never against hoped-for growth. The one-sentence test, the forgivable note, and the seller's defenses when one is proposed: earnouts and the SBA.

The form of the sale. Asset sale or stock sale decides your tax treatment, the buyer's risk, and whether your contracts and licenses move cleanly, and inside every asset sale hides a second negotiation, the allocation, that moves your after-tax check by five figures while nobody is watching. The buckets, the C corp trap, and the worked example: asset sale versus stock sale.

The buyer who already works here. Selling to a manager or a child solves transferability and keeps the sale quiet, at the cost of competition on price, and with a 2025 rule that surprises everyone: keep any equity in a partial sale and you personally guarantee the buyer's whole loan. The two shapes of an insider deal and the down-payment problem at the heart of both: management buyouts.

The paper that locks it in. Every structural decision above should be settled in the letter of intent, because the LOI is where your leverage peaks and exclusivity is where it goes to die. What must be specific before you sign, and the five-minute screen that catches terms an SBA lender will reject in week three: the letter of intent. Its close cousin, the closing-table fight over what the price includes, gets its own guide: working capital adjustments.

Reading an offer like a seller who has done this before

When a real offer arrives, run it through four questions in order. What is certain? Cash at closing, and nothing else, goes in this bucket. What is deferred? Note terms, standby provisions, security, and what happens if the buyer resells. What is contingent? Find the trigger, and check which direction it points; if any dollar requires the business to beat its own history, the structure cannot finance with an SBA loan and the offer needs rebuilding before it needs answering. And what does this buyer's financing actually allow? A generous structure from a buyer whose loan cannot support it is generosity on paper only, which is why vetting the buyer and pre-qualification sit next to this pillar rather than after it.

Then do the one thing that separates prepared sellers from everyone else: compare offers on after-everything terms. After tax, which the form of sale and the allocation decide. After risk, which means discounting the contingent pieces honestly. After time, because a dollar in year six is not a dollar at closing. The spreadsheet takes an afternoon with your CPA. It has changed more sellers' decisions than any negotiation tactic ever has.


Common questions

What percentage of the price should I expect in cash at closing?

On a typical SBA-financed Main Street deal, most of it: the loan plus the buyer's injection commonly delivers 80 to 90 percent of the price at closing, with a seller note covering the remainder. Be wary at both ends. An all-cash offer at a strong price deserves scrutiny of where the cash comes from, and an offer where a third or more of the price is deferred or contingent is a buyer proposing that you finance their acquisition while they hold the keys.

A buyer offered more money with a creative structure. How do I compare it to a smaller, cleaner offer?

Convert both to the same currency: expected after-tax dollars, with the contingent pieces discounted by an honest probability, and deferred pieces discounted for time and risk. Creative structures are not inherently bad; they are how real gaps get bridged. But complexity is a cost you pay, in risk, in legal fees, in things that can go sideways, and the premium has to be big enough to cover it. Run the comparison with your CPA before you fall for the bigger number.

Do I really need a deal attorney for a small sale?

Yes, and specifically one who does business transactions regularly, not a generalist. This pillar exists to make you a better client, not to replace counsel: you will recognize the structures, know your priorities, and spend attorney hours on drafting instead of orientation. The same goes for a CPA on the tax side. On a transaction measured in hundreds of thousands or millions, professional fees are rounding errors against a single badly drafted term.

When in my sale process should I start thinking about structure?

Before you list, in outline: know whether you can carry a note, what form of sale your entity favors, and what your after-tax floor is under a realistic structure. The detailed decisions arrive with offers, but the sellers who get run over by structure are the ones meeting these ideas for the first time with an LOI in hand and a buyer waiting on an answer. An afternoon with this pillar and an hour with your CPA, months early, is the cheap version of that education.

From reading to running it

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