Tax Implications of Selling a Business Using a Structured Installment Sale

A Structured Installment Sale (SIS) allows business owners to defer capital gains taxes by directing sale proceeds into a trust instead of receiving them at closing. Rather than losing 20–40% of your sale price to federal capital gains, NIIT, depreciation recapture, and state taxes in a single year, you receive quarterly payments over 5–20 years and pay taxes on the gain portion of each installment as received — authorized under IRS Code Section 453.

What Makes Business Sales Different

Unlike real estate, business sales involve multiple asset categories — each taxed differently. How the purchase price is allocated directly impacts your total tax burden.

Asset CategoryExamplesTax TreatmentRate
Capital AssetsGoodwill, going-concern value, client listsLong-term capital gains15–20%
Depreciable PropertyEquipment, furniture, dental chairs, technologyDepreciation recapture (ordinary income)Up to 37%
InventorySupplies, materials, work in progressOrdinary incomeUp to 37%
Non-Compete AgreementCovenant not to compete with buyerOrdinary incomeUp to 37%

Add the 3.8% NIIT and state income tax (up to 13.3%), and a business seller can lose over one-third of the sale price to taxes in a single year.

How a Structured Installment Sale Changes the Math

Maria started her dental practice with $250,000 in 2005. After 20 years of building the business, it's now worth $800,000 — a $550,000 capital gain. Here's how a traditional sale compares to a Structured Installment Sale.

Traditional Sale

Sale Price$800,000
Cost Basis($250,000)
Capital Gain$550,000
Estimated Tax Due at Closing($135,000)
Annual Income After Sale$0
Net Proceeds$665,000

Structured Installment Sale — 10-Year Note

Sale Price$800,000
Cost Basis($250,000)
Capital Gain$550,000
Tax Due at Closing$0
Annual Income (6%)$90,000/yr
Quarterly Payments~$22,500
Replaces Practice IncomeYes
$135K
Tax Deferred at Sale
$90K/yr
Replacement Income
10 Years
Predictable Payment Term

Based on estimated federal and state capital gains taxes. Actual results depend on individual tax situation and asset allocation. Consult your CPA for specific advice.

How It Works: 3-Step Process

Step 1

Promissory Note Issued

You select payment terms (5, 10, 15, or 20 years) and receive a secured promissory note from the IGH Trust. The note terms, interest rate, and payment schedule are fully documented.

Step 2

Business Sold & Funds Enter Trust

At closing, the proceeds go directly from escrow into the IGH Trust. You never take constructive receipt of the funds. This is the critical IRS requirement under Section 453.

Step 3

Deferred Taxation & Income Begins

You receive regular quarterly payments per your note. Capital gains taxes are deferred — recognized only on the gain portion of each installment as you receive it. This replaces the active income from your business with predictable passive payments.

Eligible Business Types

Dental & Medical Practices

Dentistry, orthodontics, dermatology, primary care

Law Firms & Accounting Practices

Legal practices, CPA firms, advisory firms

Consulting & Professional Services

Management consulting, IT services, engineering

Sole Proprietorships

Owner-operated businesses with appreciable goodwill

Partnerships & LLCs

Multi-member LLCs, general and limited partnerships

S-Corporations

Pass-through entities with appreciated business assets

Note on C-Corporations

C-Corporation stock sales qualify for a structured installment sale. C-Corporation asset sales face double taxation (corporate-level and shareholder-level) and typically require S-Corp conversion with a 5-year waiting period before an installment sale structure is most effective. Consult with your CPA and attorney on the optimal approach for your entity.

IRS Compliance for Business Sales

Business structured installment sales comply with the same IRS framework as real estate transactions:

  • IRS Code Section 453 — Governs installment sales for business assets, including goodwill and depreciable property
  • IRC Section 453B — Additional rules for dispositions of installment obligations
  • No Constructive Receipt — Funds flow directly from escrow to trust; seller never touches the proceeds
  • Fiduciary Trustee — Professional trust management with Craig S. Redler, JD, TEP as trustee

Frequently Asked Questions — Business Sale Tax Deferral

See How Much You Could Save on Your Business Sale

Use our free Revenue Estimator to compare a traditional sale vs. a Structured Installment Sale — or schedule a consultation with a specialist.

Important Disclosure

This information is provided for general educational and informational purposes only. It is not intended to be specific investment, tax, or legal advice and should not be relied upon as such. Tax rates and regulations are subject to change.

Always consult your tax advisor and/or attorney for specific advice pertaining to your specific situation. Rates and terms are subject to change. Past performance is not indicative of future results. Iron Gate Holdings and its affiliates do not provide tax or legal advice.

Tax Implications of Selling a Business — Structured Installment Sale | IGH Trust