THE TAX RULE THAT SAVED A $4 MILLION DEAL
few years back a client called us. He was about to sell his distribution business to his nephew.
$4 million sale price. $400,000 down payment. The rest on a seller-financed note.
He’d built the business from nothing over twenty years. His basis was next to zero. 95% of every dollar he received was taxable gain.
His tax bill on the deal: ~$1 million.
His cash at close: $400,000.
The math didn’t work. He was about to either kill the deal or borrow against the note to pay the IRS.
We told him about installment sales.
Have you heard about IRC 453?
An installment sale election lets you recognize gain as the buyer pays down the note, not at close. Same total tax. Different timing.
The IRS treats each payment as 95% gain (the proportion of his total gain to his total sale price).
$400K down payment × 95% = $380K of gain recognized in year one. Tax on that: ~$90,000. Not $1 million.
He paid ~$90K in year one. The rest of the tax came in over the life of the note, as payments arrived. The nephew runs the business. The seller gets a check every month. Everyone moved on.
That’s the unlock that no one told him about until he called us.
Another problem with sales we see all the time
A business owner sells. The CPA reports the sale. The owner pays an extra 3.8% on the entire gain in Net Investment Income Tax.
That tax shouldn’t apply. The owner participated in the business. Active business gain is not subject to NIIT.
The mechanic: when you sell S-Corp stock or a partnership interest in a business you ran, the gain on sale should be backed out on Form 8960, line 5c. Many CPAs don’t catch it. Many don’t know the line exists.
3.8% on a $2M gain is $76,000. On a $5M gain it’s $190,000.
The good news: you have three years from filing to amend a return. If the sale was in the last three years and your CPA never backed out the gain on Form 8960 line 5c, you can recover it.
After the tax year closes the money is gone.
If you’ve sold a business in the last three years, pull the sale year’s return. If line 5c is blank, you might be owed a refund.
The timing matters more than the tools
Tax planning at exit isn’t really at exit. The most valuable decisions get made years before.
Setup decisions, years before any sale
Jeff Bezos calls this kind of decision a “one-way door.” He may have stolen the mental model from someone, but I am taking it from him. Two-way doors are reversible. One-way doors aren’t. The biggest tax mistakes in exits are one-way doors people walked through years ago while not knowing it.
Entity choice. C-Corp or S-Corp. Different tax treatment at exit.
QSBS (Qualified Small Business Stock). Original-issue stock in a domestic C-Corp with under $75M in assets at issue. Hold five years and exclude up to $15M of gain from federal capital gains tax. Or 10x basis, whichever is greater. Under OBBB, partial exclusions at year three (50%) and year four (75%). Excluded industries: consulting, financial services, healthcare, law. Doesn’t apply to S-Corps. If your future exit could clear $10M and you’re forming the entity now, run the QSBS analysis before you file Form 2553.
These choices can’t be undone after the fact. You don’t convert your S-Corp to a C-Corp the year before sale and claim QSBS. One-way door.
Three to five years before
This is where the highest-leverage planning lives.
Asset separation. Your S-Corp should own the business, not the things the business uses. Real estate goes in a separate LLC. Heavy equipment too. When you sell the operating business, those assets stay with you, sold on your timeline, at capital gains rates instead of ordinary recapture.
EBITDA normalization. Personal expenses running through the business get scrubbed. The buyer’s diligence team will do this anyway. Doing it first gives you a defensible number to negotiate from.
Books and records cleanup. Buyers price uncertainty. Clean books cost you less in the multiple.
Estate planning if business value is material. GRATs and FLPs move equity to heirs at discounted valuations. Get qualified counsel and a real appraiser. This can’t be done the week before the sale, as discounts won’t apply.
At sale
Installment sale election when the math says so. The story above is the version where it saved the deal. The version where it doesn’t apply is rarer than you’d think.
Purchase price allocation. Buyer wants depreciable short-life assets. You want goodwill. Negotiate when the LOI is signed.
F-Reorg, Section 338(h)(10) election for S-Corp asset sales. Lets the buyer get the step-up basis without costing you stock-sale tax treatment. Negotiate it with the term sheet.
Asset vs. stock sale: Does it matter? It depends..
Stock sale. You sell equity. Buyer inherits everything. Long-term capital gains rates. Clean.
Asset sale. The buyer steps up basis on each asset. You pay tax on each asset class at its own rate. Depreciation recapture at ordinary income rates. Goodwill at capital gains.
The spread depends on three things.
C-Corp sellers: massive. Double taxation on asset sales. Sometimes 15% of price.
S-Corp sellers with depreciated real estate or equipment in the operating entity: meaningful. 5 to 8% of price.
S-Corp sellers with goodwill (consulting, agencies, professional services): small. 1 to 3% of price.
For most TGL readers running service businesses, the consultants who say asset vs. stock is the biggest decision are overselling. The bigger decisions are the ones above. Asset separation. NIIT cleanup. Installment election. Allocation. The 338(h)(10) when it fits.
From the buyer’s seat
Everything in this letter is also what the buyer’s diligence team is checking on the seller’s return.
The seller spent twenty years dressing the business up. The buyer needs someone trained to undress it.
That’s what a Quality of Earnings report does. Inflated add-backs. Personal expenses buried in COGS. Revenue that won’t transfer. Asset ownership structures that hide margin. Salary that was suppressed to inflate the EBITDA line. The seller’s “EBITDA is $1.2M” is not $1.2M. Two-thirds of the P&Ls we've reviewed for buyers this year had material adjustments. The seller's number is wrong more than it's right.
Bedrock is the QoE firm we built with Will McCurdy, Roger Ledbetter, Michael Girdley, and Robyn Smith for this exact moment. Will spent his career doing QoE work at PwC and RSM. He’s the person you want reviewing the numbers before you wire $4M to a seller.
The timeline most sellers get wrong
If you’re planning to sell in five years, the planning starts now.
The owners who net the most at exit are not the ones who got the highest offers. They’re the ones who set up the foundation years before any offer arrived.
Book the call
Selling in the next three to five years? Book a Visor consultation. 30 minutes. We’ll review the four things every owner needs in place before they can sell well. Entity setup. Asset separation. Books cleanup. NIIT exposure on prior sales if relevant.
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Buying or Selling a business in the $1 to $30M range? Book a call with Will at Bedrock. We’ll tell you whether the seller’s number is real before you commit to a price. The QoE pays for itself on the first add-back we catch.
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