Installment Trusts for Deferred Business Exit Taxes

 

English Alt Text: A four-panel comic shows a business owner learning about installment trusts. Panel 1: She asks how to reduce taxes from selling her company. Panel 2: A tax advisor suggests using a Deferred Sales Trust. Panel 3: He explains it spreads payments over time, deferring taxes. Panel 4: She says, “So I can invest the proceeds and pay taxes later?” and smiles.

Installment Trusts for Deferred Business Exit Taxes

Exiting a business can be one of the most financially rewarding — and tax-heavy — moments in a founder’s life.

If you're selling a company, especially one with highly appreciated value, a Deferred Sales Trust (DST) or similar installment trust strategy can help you defer capital gains taxes and smooth your income across years.

In this guide, we’ll explore how Installment Trusts work, how they differ from standard installment sales, and why they’re becoming popular with mid-market founders and exit-ready entrepreneurs.

📌 Table of Contents

💼 What Is an Installment Trust?

An Installment Trust — often called a Deferred Sales Trust (DST) — is a legal structure that enables a business owner to sell a company and defer taxes on the capital gain by receiving sale proceeds over time.

The business is sold to a trust (not the ultimate buyer), and the trust later sells it to the end buyer, creating a payment schedule for the seller.

This allows the seller to:

- Spread income over several years

- Invest proceeds inside the trust

- Control tax brackets and timing of income

⚙️ How a Deferred Sales Trust Works

Step-by-step overview:

1. Seller sets up an installment trust with help from legal counsel

2. Seller transfers ownership of the business to the trust

3. The trust sells the business to the buyer and receives the full sale proceeds

4. The trust invests proceeds and pays the seller over time based on a promissory note

Key benefit: Taxes are paid only as the seller receives principal back over years, not all at once.

📈 Tax Deferral Benefits and Income Smoothing

- Spreads capital gain tax liability over 5–20 years or more

- Smooths retirement income across lower tax brackets

- Keeps more money invested and compounding inside the trust

- May reduce exposure to Net Investment Income Tax (NIIT)

Example: A $10M business sold all at once may generate a $2.3M tax bill. But a DST structure can reduce the first-year tax hit to nearly zero.

Installment Trusts must comply with:

- IRS Code Section 453 (Installment Sales)

- Proper arm’s length transaction rules

- Documentation showing economic substance

- State-specific rules (California may treat it differently than Florida)

Important: These are not IRS-listed abusive transactions — but must be executed precisely.

🧠 When to Use Installment Trusts

Installment Trusts are ideal for:

- Founders selling businesses valued at $2M+

- Landowners selling highly appreciated real estate

- Serial entrepreneurs planning multiple exits

- Retirees with major liquidity events on the horizon

They can also work alongside Opportunity Zone investments or 1031 exchanges.

🔗 Further Resources

Explore more on business exit and tax-deferred sale strategies:

Important Keywords: deferred sales trust, business sale tax deferral, installment trust IRS, exit planning strategies, DST for founders