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Buy-Sell Agreements

One of the most commonly used tools in the estate plans of small business owners is the buy-sell agreement. Simply defined, a buy-sell agreement is a contract between a business owner and a potential purchaser (or purchasers) detailing the terms of a potential sale of the owner’s business interest. The sale is typically triggered by the owner’s death, but can be written to cover disability, retirement, divorce, personal insolvency, or loss of a professional license.

Depending on the owner’s and purchaser’s circumstances, the agreement may take several forms — obligating the purchaser to buy, or simply providing a right of first refusal; including a formal funding provision, or leaving financing to future arrangements. A properly designed buy-sell agreement can:

  • Establish a value for the business acceptable to the IRS for estate tax purposes
  • Provide the owner’s estate with liquid assets that can be distributed to heirs or invested to provide income for survivors
  • Free surviving business owners from interference by the deceased owner’s heirs

Beyond estate planning, a properly executed and funded business succession plan can increase employee morale, reduce turnover of key employees, retain customer loyalty, and improve credit standing with banks and suppliers — all parties with a direct stake in the business’s continued success.

Establishing Business Value for Tax Purposes

A major advantage of a bona fide buy-sell agreement is that it fixes the business’s value for estate tax purposes, potentially avoiding a much higher IRS appraisal. To qualify, the agreement must:

  • Be a bona fide business arrangement — not a device to transfer property to family members for less than full consideration
  • Give the potential purchaser at least the option to buy the deceased owner’s interest
  • Establish a determinable price or formula (which may or may not approximate fair market value at the time of sale)
  • Be comparable to terms arrived at through arm’s-length transactions
  • Not allow the owner to dispose of the business during their lifetime at a price higher than allowed in the agreement

The valuation clause is among the most important features of the agreement. Three approaches to establishing a determinable price:

Stated Dollar Amount
Simple and certain; freezes future growth in the estate. Drawback: the price may not reflect true value at death. If the business grows, heirs are shortchanged; if it shrinks, the buyer may refuse to complete the purchase.
Formula
Most commonly used. Accounts for changing conditions using book value, replacement cost, income capitalization, or other methods. Advantages and drawbacks depend on the formula selected and the type of business.
Professional Appraisal
Uses the most current value at the time of sale. Drawback: may not meet the IRS definition of “determinable” price, risking IRS disputes. Also makes estate planning more difficult since the estate size cannot be predicted accurately.
Important restriction: A bona fide buy-sell agreement locks the owner into the agreed value for lifetime sales as well. The owner cannot sell during their lifetime at a price exceeding the buy-sell price — otherwise the IRS will disregard the agreement for estate tax valuation purposes.

Potential Buyers

Partnerships

When a partner dies, the partnership technically must dissolve. Surviving partners must either liquidate or reorganize. Liquidation is almost never desirable. If they reorganize, surviving partners typically want to continue without interference from the deceased partner’s heirs. Because of the legal situation created by a partner’s death, the surviving partners are both the most motivated and most logical potential buyers for a buy-sell arrangement.

Closely Held Corporations

Although a corporation’s legal existence is not affected by a shareholder’s death, closely held corporation shareholders face the same practical problems as partners — and typically want to continue operations without interference from the heirs. They are natural candidates for buy-sell agreements. Shareholders have two options: they can act individually (cross purchase) or the corporation itself can act as the buyer (stock redemption). These structures are compared in detail below.

Family Members

An owner who wants to keep the business in the family but has only one willing heir faces the challenge of treating all beneficiaries fairly. A buy-sell arrangement can solve this: the estate sells the business to the capable heir at the agreed price; the sale proceeds are then distributed among all the beneficiaries (including the purchaser). This allows the owner to treat heirs equally while directing the business to those who can manage it.

Employees and Others

In sole proprietorships — and corporations with a single shareholder — finding a buyer is more difficult. Key employees, management teams, or all employees through an ESOP are possibilities. Competitors, vendors, and customers are also potential buyers. Business brokers can help when no buyer can be found independently.

Types of Buy-Sell Agreements

First Offer (Right of First Refusal)
The estate simply agrees to offer the business to the potential buyer before offering it to others. Neither party is obligated — the estate is not required to sell, and the buyer is not required to purchase. Most flexible, but most uncertain. Drawbacks: Does not meet IRS determinable-price requirement (estate may not be obligated to sell). Surviving co-owners may be forced to share control with heirs. Estate has no guarantee of liquidity.
Option to Purchase
The buyer is granted an option to purchase the interest at a stated price within a set period (usually 60–90 days). If the price reflects an arm’s-length transaction, it establishes the estate tax value even if the true value has increased since the agreement was signed — an estate freezing benefit. Drawbacks: Owner cannot sell during lifetime at a higher price. Buyer is not required to purchase — if the option lapses, the estate may be left with an illiquid, taxable asset and no buyer. Favors the buyer at the expense of the estate.
Mandatory Buy-Out
Both parties are locked in: the estate must sell, and the buyer must purchase at the predetermined price. Eliminates uncertainty for both sides. IRS accepts the price as the estate tax value. The only arrangement that achieves all three buy-sell objectives: establishes a tax value, provides estate liquidity, and ensures business continuation without the heirs. Drawback: No flexibility — family members cannot retain the business, and buyers cannot reverse their prior commitment.
Recommended approach: Mandatory buy-sell agreements are the only arrangement that reliably achieves all three estate planning objectives. First offer and option-to-purchase agreements leave too much uncertainty for the estate and its heirs.

Structuring the Buy-Out

Sole Proprietorships

A one-way buy-out between the proprietor and the potential buyer (family member, key employee, etc.). The owner drafts the terms of the agreement, which becomes effective upon the owner’s death.

Partnerships — Cross Purchase vs. Entity Plan

Partnership buy-outs take one of two forms:

Cross Purchase Plan
Each partner agrees individually with the other partners to purchase a proportionate share of any partner’s interest upon death. The partnership itself is not a party. Every partner has a separate agreement with each other partner.

Example: Adam, Ben, and Charlie are equal partners in ABC Accountants. In a cross purchase, Adam and Ben each agree to purchase one-half of Charlie’s interest if Charlie dies; Ben and Charlie do the same for Adam; Adam and Charlie for Ben.

Key advantage: Surviving partners purchase the interest at a stepped-up cost basis, reducing future capital gains tax.
Entity Plan
The partnership itself (the entity) agrees to purchase the interest of any partner who dies. The interest purchased is then allocated among surviving partners in proportion to their ownership stake.

Example: Using the same ABC Accountants example, if Adam dies, the partnership buys Adam’s interest. Ben and Charlie equally absorb Adam’s former share.

Key advantages: Fewer insurance policies needed; more equitable when partners have different ages or health conditions; easier to administer.

Corporations — Cross Purchase vs. Stock Redemption

Corporate buy-outs mirror the partnership structures. In a cross purchase, individual shareholders agree to buy one another’s shares. In a stock redemption, the corporation agrees to repurchase a deceased shareholder’s shares — the remaining shareholders’ proportionate ownership automatically increases as the redeemed shares are retired.

A “wait-and-see” agreement gives the corporation the first option to redeem; if it declines (or only partially redeems), individual shareholders purchase the remainder. If any shares remain after that, the corporation redeems the balance. This provides maximum flexibility while still guaranteeing a mandatory outcome.

Cross Purchase vs. Redemption — Basis Example

April and Beth are equal shareholders in a boutique, each contributing $10,000 at formation. The business has grown to $200,000 in total value. April dies.

Redemption plan: The corporation pays April’s estate $100,000 for her half-interest and retires the shares. Beth now owns 100% of a $200,000 business — but her cost basis is still only her original $10,000. If Beth sells the business, her taxable capital gain is $190,000.

Cross purchase plan: Beth (not the corporation) pays $100,000 for April’s shares. Beth’s total cost basis: original $10,000 + purchase price of April’s shares $100,000 = $110,000. If Beth sells the business at $200,000, her taxable gain is only $90,000.

At a 20% long-term capital gain rate, the cross purchase saves Beth $20,000 in taxes on the $100,000 difference in cost basis.

Cross Purchase vs. Entity Plan — Comparison

Factor Cross Purchase Entity / Redemption
Basis treatmentStepped-up basis for survivors — lower future capital gainNo step-up for surviving shareholders (redeemed shares retired)
Number of insurance policiesMore: n × (n−1) total policies (e.g., 6 for 3 partners, 12 for 4)Fewer: one policy per owner/partner life
Premium equity among ownersYounger owners pay higher premiums for older partners’ policiesBusiness pays all premiums; cost shared equally among owners
Personal liabilitySurvivors personally liable to buy; estate can sue individualsEstate’s contract is with the business; surviving owners not personally liable
AdministrationComplex; many policies and agreementsSimpler; one entity manages all policies
Corporate tax (C corp)No deduction for premium or interest (individual pays)No deduction for premium; interest on borrowed funds deductible by corporation
Best forPartners/shareholders of similar age; plans where step-up matters mostMultiple partners; partners of different ages; S corp or partnership step-up planning with trust
Insurance trust option: Some planners use an irrevocable life insurance trust to combine the administrative advantages of an entity plan (fewer policies) with the tax benefits of a cross purchase plan (stepped-up basis). The trust owns one policy per partner, with each partner a beneficiary of the trust. Because a trust — not the business — owns the policies, a stepped-up basis for surviving partners may be available. Additional benefit: cash values remain outside the deceased’s taxable estate. This requires careful drafting by an experienced tax attorney.

Funding a Buy-Sell Agreement

Executing a buy-sell agreement is only the first step. Unless the potential buyer has financing available, the plan has little chance of success. Four funding mechanisms exist, with widely varying reliability:

Personal or Business Assets
Leaves much to chance. Economic downturns, illness, disability, or divorce can impair resources precisely when they are most needed. Murphy’s Law applies.
Sinking Fund / Reserve Account
Regular contributions into an investment account to accumulate the purchase price. Must be actuarially based on life expectancies — if an owner dies prematurely, the fund is insufficient. Earnings are taxable. Contributions divert resources from productive uses.
Borrowing
The death of the owner weakens the business’s credit standing — lenders are most reluctant to lend precisely when they are most needed. Debt service is an additional burden going forward. Rarely a viable primary funding mechanism.
Installment Note from Heirs
Heirs accept a promissory note instead of a lump sum. Does not provide estate liquidity for the 9-month estate tax deadline. Heirs bear the risk of business failure during the installment period. The new owner faces additional debt service on top of normal operations.

Who Pays the Premiums?

In a one-way buy-out (sole proprietorship), the potential buyer owns and is the beneficiary of the policy on the proprietor’s life and pays the premiums. Since the proprietor relies on the buy-out to protect heirs, the buyer’s ability to pay premiums is critical. Several solutions exist: the proprietor may lend funds to the buyer; give the employee-buyer a raise to cover premium cost; or the business may adopt a split-dollar arrangement where the proprietor pays the portion of the premium attributable to the increase in cash value and the employee-buyer pays the rest.

In a cross purchase plan, each partner or shareholder individually owns and pays premiums on policies covering the other owners’ lives. The buy-out agreement should contractually obligate each party to pay premiums — a lapsed policy can cause the entire plan to fail. The agreement should also address what happens to policies on the surviving partners’ lives held by the deceased’s estate after the buy-out is completed (survivors may purchase the policies from the estate, or the estate may surrender them).

In an entity or stock redemption plan, the business owns the policies, is named as beneficiary, and pays the premiums. The premium is not a tax-deductible business expense; death proceeds received by the business are income-tax-free. For C corporations in a lower tax bracket than the shareholders, premiums are paid in after-tax dollars that cost less than if the shareholders paid personally. If borrowed funds finance any portion of the buy-out, the interest is tax-deductible for the corporation (but not for individual shareholders in a cross purchase).

The entity plan also requires fewer policies: three policies for a three-partner firm vs. six under a cross purchase; twelve vs. six for four partners; twenty vs. ten for five partners. Fewer, larger policies also typically cost less per dollar of coverage than many smaller ones. Many insurers offer joint “first-to-die” policies for entity plans covering multiple lives.

Summary — Insured Mandatory Buy-Sell Agreements

An insured mandatory buy-sell agreement should include provisions that:

  • Properly value the business interest (stated price, formula, or appraisal); the IRS requires the price to reflect fair value at the time the agreement is drafted
  • Obligate the estate to sell and the buyer to purchase at the agreed price (eliminates uncertainty of first offer and option-to-purchase alternatives)
  • Prevent the owner from selling during their lifetime without first giving the potential buyer an option at the agreed price
  • Prevent the owner from selling during their lifetime at a price higher than the buy-out price (establishes the IRS-acceptable tax value)
  • Release the owner’s heirs from any business debts upon completion of the transaction
  • Obligate the potential buyer to maintain adequate life insurance and pay premiums
  • Address disposal of insurance policies on surviving partners’ lives after the buy-out (purchase from estate, surrender, or continuation in trust)
  • Provide contingency financing if business value exceeds insurance proceeds; address who receives any excess insurance proceeds

Benefits to All Parties

Owner’s Estate & Heirs
  • Provides much-needed estate liquidity
  • Ensures fair value for the business interest
  • Converts an illiquid asset into cash with minimal transaction costs
  • Assures prompt, full payment — avoids estate shrinkage
  • Establishes a tax value; eliminates IRS disputes
  • Freezes the business’s estate tax value
Surviving Owners
  • Eliminates inactive interests held by heirs
  • Avoids interference and disputes with heirs
  • Guarantees funds to complete the purchase
  • Allows careers to continue uninterrupted
  • Avoids unfavorable reorganizations
  • Relieves survivors from acting as liquidating trustees
  • Provides peace of mind that the business can continue
The Business
  • Continues uninterrupted
  • Enhanced credit standing with lenders
  • Retained customer loyalty
  • Improved employee morale
  • Easier retention of key employees
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