The Cannon Journal · Liquidity Events

Selling to your partners and employees on a note, secured by the shares.

Your best buyers may already work for you. They rarely have the cash to pay all at once. A note secured by the shares is how many of these sales are built.

October 22, 20265 min readCannon Capital Management
Hands signing closing documents with a pen at a dark table

When owners sell their stake to internal partners or employees, the buyers usually pay part of the price over several years on a promissory note. Securing that note with the shares being sold, through a stock pledge, means that if the buyers stop paying, the seller has a legal right to take the ownership back. It protects the seller, and it gives the buyers a strong reason to keep paying through the final installment.

Why sell to insiders at all?

Insiders know the business, the customers and the culture. A sale to them can keep the company independent, reward the people who built it, and avoid the long marketing process of an outside sale. The catch is money. Employees and junior partners rarely have the full price in cash, and banks may lend only part of it. So the seller often finances the rest.

Seller financing turns the seller into a lender. A lender wants collateral.

What does "secured by the shares" mean?

A promissory note is the buyer's written promise to pay a set amount on set terms. On its own, an unsecured note leaves the seller as a general creditor: if the buyer defaults, the seller can sue, but has no special claim to any asset.

A secured note is backed by collateral. In an insider sale, the natural collateral is the very shares or membership interests being sold. The buyer gets ownership at closing, but signs a pledge agreement giving the seller a security interest in those shares until the note is paid. If the buyer defaults, the seller can enforce that interest and, following the agreement and state law, take the shares back or have them sold.

How does a pledge of shares usually work?

  • The pledge agreement. Sets out what counts as default, the notice and cure periods, and what the seller may do on default.
  • Perfecting the interest. Under Article 9 of the Uniform Commercial Code, which Utah has adopted, a security interest is usually perfected by holding the stock certificates, by a control agreement, or by filing a financing statement (a UCC-1) with the Utah Division of Corporations and Commercial Code.
  • Voting and distributions. The agreement usually lets the buyer vote and receive distributions while current on the note, and shifts those rights on default.
  • Other protections. Sellers often add personal guarantees, limits on new debt or large distributions, regular financial reporting and the right to a board seat until the note is paid.

Why does the pledge protect both sides?

For the seller, it means default does not leave them with a lawsuit and nothing else. Ownership can come back. For the buyers, it is a powerful reason to keep paying through the final payment, because walking away means losing the equity they have been paying for. That incentive can be worth as much as the legal remedy.

It is not a complete answer, though. If the buyers default because the business has declined, the shares that come back may be worth less than the balance owed. Sellers who finance a sale stay exposed to the business they sold. The note's size, the down payment, the term and the covenants all shape how much risk remains.

How is an installment sale taxed?

When part of the price is paid in later years, the installment method under section 453 generally lets the seller report the gain as payments arrive, rather than all at closing. Each principal payment carries a proportional share of gain. Interest on the note is taxed as ordinary income.

  • Interest rate. The note should carry at least the applicable federal rate (AFR) the IRS publishes each month. Otherwise, part of the principal can be recharacterized as interest.
  • Large notes. If installment notes from sales over $150,000 total more than $5 million at year end, an interest charge on the deferred tax can apply under section 453A.
  • Related buyers. Special rules apply when the buyer is a family member or a related entity, including a two-year resale rule. Employees and unrelated partners are usually not related parties, but the definitions should be checked.
  • Taking the shares back. Repossessing pledged shares after a default has its own tax consequences for the seller.

Utah taxes the gain at its flat individual rate as it is reported, following the federal installment method. Utah starts from federal adjusted gross income, which includes installment gain in the year it is reported, and makes no separate adjustment for it (Utah Code sections 59-10-103 and 59-10-114, current as of October 2026).

What else should be settled first?

  • Valuation. An independent valuation helps the price hold up with the IRS and keeps the conversation with your own team fair.
  • The operating or shareholder agreement. It should allow the pledge and say what happens to the shares on default, death or departure.
  • Your own plan. How much you need up front, how long you can wait for the rest, and how much of your net worth will still depend on the business.

A hypothetical example

Hypothetical. The founder of a Utah professional firm agrees to sell her stake to three partners and two senior employees. They pay part of the price at closing and sign a ten-year note, with interest at least at the AFR, for the rest. The note is secured by a pledge of the shares they are buying, with a personal guarantee from each buyer and limits on distributions while the note is outstanding. If the buyers keep paying, the founder reports her gain over ten years as she is paid. If they default, she can enforce the pledge and take the shares back, and the buyers lose the ownership they have been paying for.

We are not brokers and take no part in the transaction. Our business and exit planning page describes how we work alongside your attorney and CPA, so the deal terms, the tax and your own plan for after the sale point in the same direction.

Educational only. Not investment, tax, or legal advice. Every situation is different; the right answer depends on the numbers, and that's what the strategy session is for. Investing involves risk, including possible loss of principal.

Questions people ask

Why secure a promissory note with the shares being sold?

So that if the buyer defaults, the seller has a legal right to take the ownership back rather than only suing for payment. It also gives the buyer a strong reason to keep paying until the note is paid off.

How is a business sale paid over time taxed?

Under the installment method, the seller generally reports a proportional share of the gain as each principal payment is received. Interest on the note is taxed as ordinary income.

What interest rate should a seller-financed note carry?

At least the applicable federal rate the IRS publishes each month. A lower rate can cause part of the principal to be treated as interest for tax purposes.

What if the business declines and the buyers default?

The seller can enforce the pledge and take the shares back, but they may be worth less than the balance owed. That is why down payments, guarantees and covenants are part of the design.

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