TL;DR
  • Plan before the letter of intent. The sale structure, how the price is allocated, gifts, and any move to another state are hard or impossible to change once you sign one.
  • Structure is the biggest lever. In our hypothetical $20 million sale, the owner keeps $12.6 million after federal tax if the C corporation sells its assets, $15.5 million if the owner sells the stock, and $17.9 million if the stock qualifies for the Section 1202 exclusion.
  • Negotiate the allocation. For an S corporation or partnership owner at 2026 top rates, every $1 million of price moved from ordinary income (gain on equipment you already wrote off, or a noncompete) to capital gain on goodwill saves up to about $170,000, and more for consulting pay, which also carries Medicare tax.
  • Most moves defer tax rather than erase it. Installment payments, rollover equity, an ESOP, and Opportunity Zone funds push the tax later. Owners who actively run an S corporation or partnership also avoid the 3.8% Net Investment Income Tax.
  • Give early or not at all. In Estate of Hoensheid, an owner who gave stock to charity just before closing was still taxed on the gain, and a flawed appraisal cost him the deduction too.
  • Two 2026 timing points. Illinois now taxes federally excluded Section 1202 gain at 4.95%. And if your sale closes on or after about July 6, 2026, your 180-day window reaches January 1, 2027, when gain invested in an Opportunity Zone fund qualifies for the new program under IRS Notice 2026-40.
  • Talk to your own advisors first. Run every move here past a tax accountant and a wealth manager before you act. If you do not have them yet, we can introduce you to people we trust.

To minimize taxes when selling a business, settle three things before you sign a letter of intent: whether the buyer purchases your stock or your company’s assets, how the price is split between goodwill and ordinary-income items, and the timing of any gifts, move to another state, or reinvestment. After the letter of intent, most of these are hard or impossible to change. The legal moves that matter most:

  • Choosing the sale structure, and pricing any tax election into it
  • Negotiating the purchase price allocation
  • Qualifying for the Section 1202 small business stock exclusion
  • Staying outside the 3.8% Net Investment Income Tax by actively running the business
  • Deferring gain through installment payments, rollover equity, an ESOP, or an Opportunity Zone fund
  • Making charitable gifts, family gifts, and any change of residency years ahead rather than weeks ahead

None of these is a loophole. Each has conditions, and missing one can undo the benefit.

This guide is the planning companion to our guide to what you keep after selling a business, which lists everything that comes out of the headline price. Here we cover only the tax, and what an owner can still change.

How much capital gains tax do you pay when you sell a business in 2026?

Tax on a sale is figured on your gain, which is roughly what you receive minus your tax basis (generally what you paid for the stock or assets, less depreciation already deducted), and different parts of that gain are taxed at different rates. These are the federal figures for 2026, from the IRS inflation adjustments in Revenue Procedure 2025-32 and the Internal Revenue Code.

Tax2026 rate and thresholdWhat it applies to
Long-term capital gain0% up to $98,900 of taxable income (married filing jointly) or $49,450 (single); 15% up to $613,700 or $545,500; 20% above thatGoodwill and stock held more than a year. In a sale of any size, nearly all of the gain lands in the 20% band.
Ordinary incomeTop rate 37% above $768,700 (joint) or $640,600 (single)Depreciation recapture on equipment, inventory, noncompete payments, and consulting fees
Unrecaptured Section 1250 gainUp to 25%The part of gain on buildings that reflects depreciation already taken, per IRS Topic 409
Net Investment Income Tax3.8% above $250,000 of modified adjusted gross income (joint) or $200,000 (single); not indexed for inflationGain from businesses you own passively and from C corporation stock; usually not gain from an S corporation or partnership you actively run
Corporate income tax21% (Section 11)Gain a C corporation recognizes when it sells its own assets, before anything reaches you
Built-in gains tax21%, for five years after a C corporation converts to S (Section 1374)Value that built up while the company was still a C corporation
Free Valuation Range

About a dozen quick questions and two minutes get you a ballpark range for your business, built from published industry transaction multiple ranges, with the math behind it. It is a directional estimate, not a formal valuation.

Value My Business

One caution if you look these up yourself: the IRS’s capital gains topic page, last reviewed in September 2026, still shows the 2025 brackets. The 2026 figures above come from the revenue procedure itself. State tax comes on top, and we cover it in move 10.

A hypothetical worked example: one price, five tax outcomes

Take a hypothetical company that sells for $20 million. Its assets have a tax basis of $2 million, and the owner’s basis in the stock is $1 million. The owner is married, files jointly, and has held stock issued after September 27, 2010 for more than five years. For simplicity we apply the top federal rates, 21% at the corporate level and 23.8% (20% plus the 3.8% Net Investment Income Tax) to the owner’s capital gain on C corporation stock, and we ignore state tax, transaction costs, debt, and depreciation recapture. The figures are illustrative, not a Salt Creek transaction or a typical deal, and the example differs from the one in our net-proceeds guide, which also nets out debt and escrow.

How the $20 million sale is structuredFederal taxOwner keeps, before state tax
C corporation sells its assets, then distributes the cash to the owner$7.4M ($3.78M corporate, then $3.62M on the distribution)$12.6M
C corporation sells assets, but $6M is the owner’s personal goodwill, sold directly$6.4M$13.6M
Owner sells the C corporation stock$4.5M$15.5M
Same company had always been an S corporation; it sells its assets and the owner is active in the business$3.8M$16.2M
Owner sells C corporation stock that qualifies under Section 1202 ($10M of gain excluded)$2.1M$17.9M

The math, row by row. In the asset sale, the corporation pays 21% on its $18 million gain, or $3.78 million, and distributes the remaining $16.22 million. The owner then pays 23.8% on $15.22 million of gain, or $3.62 million. In the personal goodwill row, the corporation sells $14 million of assets and pays $2.52 million, the owner pays $2.49 million on the distribution, and the owner pays $1.43 million on the $6 million of goodwill sold directly, at the same 23.8% for consistency. In the stock sale, the owner pays 23.8% on a $19 million gain. In the S corporation row, the $18 million gain on the assets passes through to the owner and raises the owner’s stock basis to $19 million, so the $20 million distributed adds $1 million more; the total $19 million gain is taxed once at 20%, with no 3.8% because the owner is active. In the Section 1202 row, stock acquired after September 27, 2010 and before July 5, 2025 and held more than five years can exclude the greater of $10 million or ten times basis, here $10 million, so tax applies to the remaining $9 million.

The table leaves three things out. First, a buyer of C corporation stock does not get to restart depreciation on the assets at the price it paid (a “stepped-up basis”), so it may pay less for stock than for assets; the comparison that matters is after-tax cash across real offers, not tax alone. Second, real S corporation asset sales usually include some ordinary income from equipment recapture, so the $3.8 million is a floor. Third, state tax changes the totals: an Illinois resident owes 4.95% on top in every row, and from the 2026 tax year that includes the $10 million excluded federally under Section 1202, about $495,000 more. In the asset-sale rows, an Illinois company also owes tax on its own gain: 9.5% combined for a C corporation and a 1.5% replacement tax for an S corporation, per the Illinois Department of Revenue.

When each move has to happen

Many of these moves work only if they happen early enough. The table sorts the moves in this guide by the latest point at which they still reliably work.

Latest safe timeMoveWho it fits
Five or more years before a saleEither hold qualifying C corporation stock long enough for Section 1202, or, if the stock cannot qualify, convert to an S corporation to start the five-year built-in gains clock (not both: converting ends Section 1202 eligibility)C corporation owners
Years before, with a real moveChange state of residenceOwners who genuinely plan to live elsewhere
Before a buyer is in the pictureGifts and trust transfers of company interests to familyOwners whose estate may exceed the $15 million per-person federal exclusion ($30 million for a married couple)
Before the sale is a practical certainty, in practice before a letter of intentGifts of shares to a donor-advised fund or charitable remainder trust; personal goodwill planningCharitably inclined owners; C corporation owners whose relationships drive the business
In the letter of intentStock or asset sale, tax elections and any gross-up, purchase price allocation principles, rollover equityEvery seller
In the purchase agreementInstallment payments, earnout terms, consulting and noncompete paymentsEvery seller with deferred or post-closing payments
During the year of saleState pass-through entity tax election, with the tax paid by December 31; choosing the closing dateS corporation and partnership owners in an asset sale
After closingReinvest gain in an Opportunity Zone fund within 180 days; buy ESOP replacement securities within 12 monthsOwners with gain to reinvest; C corporation owners selling to an ESOP

The 12 moves, in order of how much they usually matter

1. Choose the structure, and price the tax election into it

The first question is whether the buyer is purchasing your stock or your company’s assets, and the answer interacts with your entity type. A C corporation that sells its assets is taxed twice, once at 21% and again when the cash reaches you, which is why C corporation owners usually push for a stock sale. An S corporation or LLC taxed as a partnership is taxed once either way, so for those owners the questions are allocation and ordinary income rather than double tax. A sole proprietorship or single-member LLC is treated as an asset sale for tax purposes, so allocation (move 2) is its main lever. Our guide to asset sales versus stock sales covers the legal side of that choice.

Buyers usually want an asset purchase because it gives them a stepped-up basis they can depreciate and amortize. When the company is an S corporation or a subsidiary of another corporation, tax elections can bridge the gap; they are not available for a C corporation owned by individuals. A Section 338(h)(10) or Section 336(e) election treats a stock sale as an asset sale for tax purposes, which The Tax Adviser describes as giving the buyer “the convenience of a stock purchase with the tax benefits of an asset acquisition.” Private equity buyers of S corporations often use an F reorganization instead, a pre-sale restructuring that lets the buyer purchase an LLC holding the business, under Revenue Ruling 2008-18, which delivers a step-up without the 80% change of ownership a 338(h)(10) election requires and still allows a tax-deferred rollover. Both can shift tax onto the seller when the deemed asset sale (a stock sale the tax law treats as an asset sale) creates ordinary income, and sellers, as The Tax Adviser puts it, “typically require a gross-up” for that cost, meaning the buyer pays extra to cover the added tax. Ask for the gross-up in the letter of intent. Once you have agreed to negotiate only with that buyer, it is a concession you are asking for rather than a term you are trading.

If you run a C corporation and a sale is five or more years out, ask your tax advisor about converting to an S corporation now. After conversion, gain on value that built up while the company was a C corporation is still taxed at the corporate rate under Section 1374 if the assets are sold within the five-year recognition period, so conversion helps only if the clock has time to run. Converting also gives up any future Section 1202 exclusion, so check that first (move 4).

2. Negotiate the purchase price allocation

In an asset sale or deemed asset sale, the price is split across seven classes of assets, from cash through inventory and equipment to goodwill, and both sides report the split to the IRS on Form 8594. The split matters because the classes are taxed differently. Gain on equipment up to the depreciation already taken is ordinary income, as IRS Publication 544 states, while gain on goodwill is generally capital gain. Payments for a noncompete are ordinary income to you, and The Tax Adviser notes that sellers therefore generally prefer the price allocated to capital assets “like goodwill and real estate” rather than to covenants not to compete. Consulting agreements are worse still for the seller: they are compensation, taxed as ordinary income and subject to payroll or self-employment tax.

The buyer often wants the opposite. Equipment can now be written off immediately: the July 4, 2025 tax law (Pub. L. 119-21, often called the One Big Beautiful Bill Act) restored 100% bonus depreciation for property acquired after January 19, 2025 (Section 168(k)), while goodwill and noncompetes are amortized over 15 years under Section 197, and a consulting agreement gives the buyer a current deduction. So every dollar the buyer moves to equipment or consulting is worth more to them and costs you more. For an S corporation or partnership owner at 2026 top rates, moving $1 million from ordinary income at 37% to capital gain at 20% saves up to about $170,000, and more for consulting pay, which also carries Medicare tax. The saving is smaller where recapture qualifies for the 20% qualified business income deduction, a deduction for owners of pass-through businesses (S corporations, partnerships, and sole proprietorships, whose income is taxed on the owners’ returns). In a C corporation asset sale the math changes: the company pays a flat 21% on recapture and goodwill alike, and its goodwill is taxed again when the cash reaches you (about 39.8% in all), so a noncompete paid to you personally at 37% can cost less than the same dollars allocated to the company’s goodwill. Under Section 1060, an allocation the two sides agree in writing binds both of them, so settle it during negotiation rather than leaving it to the buyer’s accountants after closing. Keep it defensible: in Kennedy, the Tax Court held that payments a seller reported as capital gain on goodwill were ordinary income, because the terms were “determined to minimize taxes” rather than based on economic realities.

If the business owns its building, it can often be carved out. Keeping the real estate and leasing it to the buyer leaves the building’s gain, including any unrecaptured Section 1250 gain, untaxed until you sell it, and gives you rental income in the meantime. A like-kind exchange will not help with the rest of the business: under the 2017 tax law, Section 1031 “now applies only to exchanges of real property and not to exchanges of personal or intangible property,” per the IRS, so goodwill, equipment, and company stock do not qualify.

3. In a C corporation, sell your personal goodwill directly

When customers buy from a business because of the owner’s own relationships, reputation, or skill, part of the goodwill can belong to the owner rather than the company. Selling that personal goodwill directly to the buyer takes it outside the corporation, so it is taxed once instead of twice. The principle dates to Martin Ice Cream Co. (1998), and in our example it adds about $1 million to what the owner keeps.

It fails when the paperwork says the goodwill already belongs to the company. In Howard, the owner’s employment agreement and noncompete with his own company made the goodwill the corporation’s, and the court upheld the IRS’s treatment of the payment as a dividend. If you have a noncompete or employment agreement with your own company, raise this with your tax advisor well before a letter of intent, and expect it to need a separate purchase agreement and an appraisal.

4. Check whether your stock qualifies under Section 1202

Qualified small business stock can exclude some or all of the federal gain on a sale. Under Section 1202, as amended in July 2025:

  • The company must be a domestic C corporation (including an LLC that has elected to be taxed as one) for substantially all of your holding period, with at least 80% of its assets used in a qualifying active business, and you must have acquired the stock at original issue, for money, property, or services, rather than buying it from another shareholder.
  • Its gross assets must not have exceeded $50 million when the stock was issued, or $75 million for stock issued after July 4, 2025.
  • Stock acquired after September 27, 2010 and on or before July 4, 2025 must be held more than five years for a 100% exclusion; stock acquired earlier gets only 50% or 75%, and the gain it does not exclude is taxed at up to 28%. Stock acquired after July 4, 2025 can exclude 50% after three years, 75% after four, and 100% after five.
  • The exclusion is capped per company at the greater of ten times your basis or $10 million ($15 million for stock acquired after July 4, 2025, indexed after 2026).
  • Excluded fields include health, law, engineering, architecture, accounting, consulting, financial services, and any business whose principal asset is the reputation or skill of its employees, plus banking, insurance, financing, leasing, farming, mining, hotels, and restaurants.

Two planning points follow. First, the cap applies per taxpayer, and stock given away keeps its status: under Section 1202(h), a person who receives the stock by gift is treated as having acquired it the same way, and as holding it for the giver’s holding period. That is why some families spread qualifying stock among relatives or trusts well before a sale. Spouses filing jointly share one cap, and a gift to a grantor trust (one whose income is still taxed to you) does not create a new one. A gift made once a sale is a practical certainty can still be taxed to the giver, so ask tax counsel whether it works for you. Second, state treatment differs. For tax years ending on or after December 31, 2026, Illinois requires the federally excluded gain to be added back to state income, per the Illinois Department of Revenue, and California does not follow the federal exclusion either. S corporation stock and LLC interests taxed as a partnership do not qualify at all, and rolling qualifying stock into a partnership holding company can forfeit future benefit, as our rollover equity guide explains.

5. Stay outside the 3.8% Net Investment Income Tax

The 3.8% tax reaches gain from a trade or business that is a passive activity for you, measured by the material participation rules of Section 469 (Section 1411). In its Q&A, the IRS lists “gains from the sale of interests in partnerships and S corporations (to the extent the partner or shareholder was a passive owner)” as covered, and operating income from a nonpassive business as not covered. So an owner who works in an S corporation or partnership usually pays no 3.8% on the sale, while a co-owner who has not materially participated in at least five of the last ten years may owe it on their share of the gain: $38,000 per $1 million.

If you are winding down your role before a sale, ask your tax advisor how that affects your participation, and keep a record of the hours you work. C corporation stock is different: gain on it is investment income whether or not you work in the business, which is why the C corporation rows in our example use 23.8%.

6. Spread the gain: installment payments, earnouts, and the closing date

When at least one payment arrives after the year of sale, Section 453 generally lets you pay tax as you are paid. Earnouts are reported the same way by default under Treasury Regulation 15a.453-1. Be clear about what that buys. In a sale of any real size, nearly all of the gain is taxed at 20% whether it arrives in one year or five, so spreading it mostly defers tax rather than reducing it. The value is the use of the money in the meantime, set against the risk of holding a buyer’s note, which our guide to seller protection after closing covers.

The deferral has limits. Depreciation recapture is taxed in the year of sale even if the cash comes later (Section 453(i)), so a note does not defer that part. If installment obligations from sales over $150,000 that arise in one year total more than $5 million at year-end, Section 453A adds a yearly interest charge on the deferred tax. And borrowing against the note is treated as receiving payment on it. Our guide to earnouts, escrows, and holdbacks covers how often those deferred payments are actually collected.

The closing date is the simplest timing lever. A sale that closes on January 4 rather than December 30 generally moves the tax to the following year’s return, which can matter if you expect a lower-income year. It does not change the rate unless the law changes in between.

7. Roll part of the price into the buyer’s equity

With a private equity buyer, the part of the price you reinvest as rollover equity can usually be received without tax at closing under Section 721 or Section 351 (the rules for tax-free contributions to a partnership or a corporation), with the gain deferred until the stake is later sold. It is deferral, not forgiveness, and it only makes sense if you want the investment for its own sake. Our rollover equity guide covers the tax tests, the terms that decide what the stake is worth, and the six-year median wait for the second payout.

8. Sell to an ESOP and use Section 1042

An owner of a C corporation who sells to an employee stock ownership plan can defer the gain under Section 1042 by reinvesting the proceeds in qualified replacement property, generally stocks and bonds of US operating companies. The conditions: the ESOP must own at least 30% of the company immediately after the sale, you must have held the stock at least three years, and the replacement securities must be bought between three months before and twelve months after the sale. Today this applies to C corporations only. For sales after December 31, 2027, the SECURE 2.0 Act opens it to S corporation stock, but only for up to 10% of the amount realized. Compare an ESOP on after-tax proceeds against other buyers’ offers rather than on the tax deferral alone.

9. Give to charity before the sale, not during it

Giving appreciated shares to a donor-advised fund or charitable remainder trust before a sale can produce a deduction and keep you from being taxed on the gain on the donated shares. The gift has to come early enough. In Estate of Hoensheid (2023), the Tax Court found that by the time the owner gave shares to a donor-advised fund, the sale had already become a “practical certainty,” so he was taxed on the gain anyway. It also denied the deduction outright because the appraisal did not meet IRS requirements, as Lathrop GPM summarizes. The court weighed the actions already taken toward the sale, the contingencies still open, and the status of corporate approvals, not only whether the charity was legally obligated to sell. The practical rule: if you want to give, do it before a letter of intent, and get a qualified appraisal. From 2026 the deduction is also worth a little less for top-bracket owners: only gifts above 0.5% of your income count (Section 170(b)(1)(I)), and itemized deductions are trimmed so each dollar saves about 35 cents rather than 37 (Section 68). Giving shares away removes the tax on them because it removes their value from your pocket, so give only what you meant to give anyway.

A charitable remainder trust lets you defer tax on the sale of the assets you put in and receive an income stream of at least 5% and no more than 50% of the trust’s value each year, for life or up to 20 years, with at least 10% of the initial value left to charity. The payments are taxed to you as they arrive. S corporation stock generally cannot go into one, because a charitable remainder trust is not an eligible S corporation shareholder (Section 1361), so S corporation owners usually need a different route.

10. Plan the state tax: residency, sourcing, and the pass-through entity tax election

State tax on the gain ranges from nothing in Texas and Florida to 4.95% in Illinois and more than 13% at the top in California; our guide to what you keep has the state detail. Residency, sourcing, and one election can change it.

Residency, if the move is real. States tax their residents on all income: California says residents are “taxed on all income regardless of source,” per the Franchise Tax Board. Moving before a sale can help, but the old state may audit. New York says your domicile does not change until you show by “clear and convincing evidence” that you have abandoned it, and that filing a certificate of domicile or registering to vote elsewhere is not enough, per its Department of Taxation and Finance. A move made in the months before a closing invites exactly that question.

Sourcing. Gain on stock you sell is generally taxed by your state of residence, Venable explains, but an asset sale by an S corporation or partnership can be taxed in each state where the business operates. In 2022, a California appeals court held that a nonresident shareholder’s gain from an S corporation’s sale of goodwill was partly California-source, Grant Thornton reports. A business with operations in several states should model both structures.

The pass-through entity tax election. The 2025 law raised the federal cap on deducting state and local taxes to $40,400 for 2026. But the higher cap shrinks by 30% of income above $505,000 and never falls below $10,000, so in a sale year you are almost certainly back at $10,000, as Cooley explains. The same law left state pass-through entity tax elections intact. When an S corporation or partnership elects to pay state tax at the entity level, that tax is deducted in computing the owners’ federal income rather than lost to the cap. To deduct it against the sale-year gain, the entity generally has to pay the tax by December 31 of the year of sale, because IRS Notice 2020-75 allows the deduction for the year in which the payment is made. On an asset sale, where the entity itself recognizes the gain, that can be worth a great deal: Illinois tax at 4.95% on an $18 million gain is about $891,000, and deducting it at the entity level instead of losing it to the cap saves federal tax on that amount, roughly $180,000 to $330,000 depending on the rate it offsets. Illinois removed the expiration date from its election in June 2026, per Sikich. Each state sets its own election deadline, so put it on the calendar early. Illinois S corporations and partnerships also owe a 1.5% replacement tax, a separate Illinois tax on business income, per the Illinois Department of Revenue, which reaches gain when the entity sells its assets.

11. Move future growth to family before the value is fixed

For 2026, each person can give away $15 million during life or at death before federal estate or gift tax applies, per the IRS, and the 2025 law indexes the amount for inflation from 2027. Owners whose estates may exceed that often transfer non-voting interests to family trusts years before a sale, at values that reflect discounts for lack of control and marketability, or use grantor retained annuity trusts, which pay you a fixed annuity for a set term and pass any growth above an IRS-set interest rate to heirs free of gift tax. Katten cautions that if the estate planning transaction and the sale happen too close together, the IRS can argue the valuations should be equal, which erases the discount. This is estate tax planning rather than income tax planning, but for a family business it is often where the largest numbers sit, and it is one reason our succession planning guide starts the clock years out.

12. Reinvest the gain in a Qualified Opportunity Fund

Capital gain invested in a Qualified Opportunity Fund within 180 days of the sale can be deferred, and if the investment is held at least ten years, its own appreciation can be excluded, per the IRS. Only the gain needs to be invested, not the whole price. The 2025 tax law replaces the original program, whose deferral ends on December 31, 2026, with a permanent version: for investments made on or after January 1, 2027, deferred gain is recognized on the fifth anniversary of the investment, and investments held five years get a 10% basis increase, meaning 10% of the deferred gain is never taxed, or 30% in a rural fund, RSM explains.

That makes timing unusually important right now. IRS Notice 2026-40 confirms that gain arising before 2027 can go into the new program as long as the investment is made after December 31, 2026, per EisnerAmper. An owner whose sale closes on or after about July 6, 2026 has January 1, 2027 inside the 180-day window (gain that flows through a partnership or S corporation can start the window later), a point CLA and HCVT both flag. Check that the fund invests in zones designated under the new program, since property bought after 2026 in the original zones generally no longer qualifies, and evaluate the fund as an investment first: the tax benefit does not make a weak fund a good one.

Moves that backfire

The moveWhy it backfires
Giving shares to charity or family after a letter of intentOnce the sale is a practical certainty, the gain can be taxed to you anyway, as in Hoensheid, and close timing can erase valuation discounts on family gifts.
Labeling as “goodwill” price that is really for consulting or a noncompeteTerms driven by tax rather than economics can be recharacterized as ordinary income, as in Kennedy.
Claiming personal goodwill while you have a noncompete or employment agreement with your own companyCourts have treated that goodwill as the company’s, and the payment as a dividend, as in Howard.
Agreeing to a 338(h)(10) election or F reorganization without a gross-upThe buyer gets the tax benefit of an asset purchase, and you may pay ordinary income tax on part of the gain.
Converting to an S corporation a year before sellingThe built-in gains tax still applies to an asset sale inside the five-year recognition period.
Moving states shortly before closing without really relocatingThe former state can still tax you as a resident, and a large gain is exactly what draws a residency audit.
Taking a large seller note mainly for the tax deferralRecapture is taxed upfront anyway, notes above $5 million can carry an interest charge, and you become the buyer’s lender.
Rolling qualifying C corporation stock into an LLC holding companyThe Section 1202 benefit does not carry into a partnership rollover.

Tax planning by sector

The same rules land differently by industry, and our M&A glossary defines the deal terms used here. Dental practices, accounting firms, consulting businesses, and engineering firms fall in Section 1202’s excluded fields, so owners in those sectors should not count on the exclusion even as C corporations; our guides to dental practice valuations and valuing an accounting firm cover how those deals are usually priced. Equipment-heavy businesses such as HVAC and plumbing companies and manufacturers have the most depreciation recapture at stake in the allocation, and manufacturers that own their buildings have unrecaptured Section 1250 gain to plan for as well. MSPs are often sold to private equity platforms with rollover equity, which makes the rollover tax tests central. Owners in MSP and IT services, dog daycare and pet care, preschool and childcare, business services, and industrials and manufacturing can find sector-specific buyer and structure detail on those pages. In every sector, whether a business falls in an excluded field for Section 1202 depends on what it actually does, not on its industry label.

What this guide cannot tell you

This guide summarizes general federal rules and a few state rules as of October 2026, from the Internal Revenue Code, IRS publications, state tax authorities, and law and accounting firm analyses. Several of the planning cases cited are older decisions; the principles still apply, but the facts of each case drove its result. The worked example is hypothetical, uses top marginal rates, and ignores state tax, recapture, deal costs, and how a buyer prices stock against assets. What you actually owe depends on your entity, basis, residence, holding periods, and the documents you sign. Salt Creek Advisory is not a tax advisor: a CPA and tax attorney experienced in business sales should model your transaction before you sign a letter of intent.

How Salt Creek works with your tax advisors

Before acting on anything in this guide, consult a tax accountant and a wealth manager who know your situation. We are not your tax advisor, and we do not try to be, but we have a strong network of tax accountants and wealth managers who work with owners before and after a sale, and we are glad to introduce you if you do not already have the right people.

What we do is bring your CPA and tax counsel in before the letter of intent, when structure, allocation, gross-ups, and rollover are still negotiable, and then compare every offer on the cash you keep after tax rather than on the headline price. Competing offers matter here too: a buyer that knows other bidders are at the table is more likely to agree to a gross-up or a fair allocation. If a sale may be years away, our guide to when to start exit planning covers what to put in motion first. Jack and Connor Pitts are directly involved in any engagement we take on, and our standard M&A engagements have no upfront retainer.

Frequently asked questions

How can I legally reduce taxes when I sell my business? The largest legal levers are the structure of the sale (stock or assets, and any tax election), how the price is allocated between goodwill and ordinary-income items, the Section 1202 small business stock exclusion for qualifying C corporations, avoiding the 3.8% Net Investment Income Tax by being active in the business, and deferral through installment payments, rollover equity, an ESOP, or an Opportunity Zone fund. Gifts and residency changes work only when made well before the sale.

What is the federal tax rate on selling a business in 2026? Long-term capital gain is taxed at 0%, 15%, or 20%; for married couples filing jointly, 20% applies to taxable income above $613,700. Equipment recapture, noncompete payments, and consulting fees are ordinary income, taxed at up to 37%. A 3.8% Net Investment Income Tax can apply on top for passive owners and on C corporation stock.

Is an asset sale or a stock sale better for taxes? For the seller, a stock sale is usually better, especially for a C corporation, where an asset sale is taxed twice. For S corporations and partnerships the gap is smaller and depends on how much of the price is ordinary income. Buyers usually prefer assets for the stepped-up basis, so the real comparison is after-tax cash across actual offers. Our asset sale vs. stock sale guide compares the two in full.

Can I avoid paying taxes entirely when I sell my business? Rarely. Most legal moves reduce or defer the tax rather than erase it. The main exceptions are the Section 1202 exclusion for qualifying C corporation stock and shares given to charity well before a sale, though you give up the value of those shares. A Section 1031 like-kind exchange does not apply to goodwill, equipment, or company stock, only to real estate.

Does the 3.8% Net Investment Income Tax apply when I sell my business? It applies to gain from a business you own passively and to gain on C corporation stock. It generally does not apply to gain from an S corporation or partnership you actively run. The threshold is $250,000 of modified adjusted gross income for joint filers and $200,000 for single filers, and it is not indexed for inflation.

Can I avoid capital gains tax by giving shares to charity before I sell? Yes, if the gift happens before the sale is a practical certainty and is backed by a qualified appraisal. In Estate of Hoensheid, the gift came too late, so the owner was taxed on the gain anyway, and a defective appraisal separately cost him the deduction. In practice, give before signing a letter of intent.

Does an installment sale reduce my taxes? It mostly defers them. In a large sale nearly all of the gain is taxed at 20% whether it arrives in one year or several. Depreciation recapture is taxed in the year of sale regardless, and installment obligations over $5 million can carry an annual interest charge.

Does my company qualify for the Section 1202 exclusion? Only if it has been a C corporation for substantially all of your holding period, you acquired the stock at original issue, its gross assets were under the limit when the stock was issued, at least 80% of its assets are used in an active qualifying business, you have met the holding period, and it is not in an excluded field such as health, law, accounting, consulting, engineering, or financial services. S corporation stock and LLC interests taxed as a partnership do not qualify, and stock acquired before September 28, 2010 gets a partial exclusion at most.

Does Illinois tax gain excluded under Section 1202? Yes, for tax years ending on or after December 31, 2026. Illinois requires taxpayers to add federally excluded Section 1202 gain back to state income, so it is taxed at the 4.95% state rate.

Should I move to a state with no income tax before selling? Only if you are genuinely relocating. States tax residents on all their income, and states such as New York require clear and convincing evidence that you have abandoned your old domicile. An asset sale by a pass-through business can also be taxed where the business operates, regardless of where you live.

Can I put my 2026 sale gain into an Opportunity Zone? You can invest the gain in a Qualified Opportunity Fund within 180 days of the sale. Under IRS Notice 2026-40, gain from 2026 qualifies for the new program if the investment is made after December 31, 2026, which brings five years of deferral and a 10% basis increase, or 30% for rural funds.

When should I start tax planning for a business sale? Ideally years ahead for entity conversions, Section 1202 holding periods, residency, and family gifts, and in every case before you sign a letter of intent, while structure, allocation, and gross-ups are still negotiable.

Sources