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Business owners: Which buy-sell arrangement is right for you?

Kelly Kowalski, Cliff Noreen, and Bronwyn Shinnick

Posted on August 17, 2022

Business owners: Which buy-sell arrangement is right for you'
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Describe the most common types of buy and sell arrangements.

Discuss the advantages each type may have for your business. 

Note how each could present challenges, depending on your business circumstances.

There are several types of buy and sell arrangements, each with its own advantages and disadvantages. Ultimately, all are methods to plan for the orderly transition of a business after a triggering event, such as the retirement, death, or disability, of one of the owners.

The type you’ll choose is largely based on the form of your business organization (e.g., sole proprietorship, partnership, S corporation or LLC) and the number of owners or stockholders.

Here’s a quick description of the most common types of arrangements.

Here is a closer look at each.

The Cross-Purchase Arrangement

This arrangement is between two or more co-owners, each of whom agrees to purchase the interest of the other(s) after a triggering event.

The purchase is typically funded with life insurance. Each co-owner buys a life insurance policy on the other(s) and is also the policy beneficiary. Either a death benefit or a loan from the policy’s cash value 1 provides the necessary funds.

· The Advantages

If the death of an owner is the triggering event, then the proceeds pass directly to the other owner(s) tax free. They also receive a step-up in tax basis that will reduce their income taxes if and when they eventually sell their shares.

The life insurance proceeds go to the individual owner(s) and aren’t subject to claims of corporate creditors.

· The Disadvantages

If there are multiple owners, then there are multiple life insurance policies that can be costly and difficult to administer.

Each business owner must meet the underwriting requirements for their specific life insurance policy coverage.

There may also be a big difference in the premiums each owner pays due to significant differences in the ages and health of the others.

The Entity Purchase (aka Stock Redemption Arrangement)

Here, it’s the company that agrees to redeem the shares of an owner after a triggering event. To fund the purchase, the business buys life insurance on all of the owners, pays the premiums, and is the beneficiary.

· The Advantages

This simplifies matters when there are a number of owners and number of policies. The corporation owns only one policy per owner.

The business absorbs any disparities in premiums so younger, healthier owners don’t have to.

· The Disadvantages

There’s no step-up in basis for the owners of the business. After a triggering event, the remaining owners will pay capital gains tax on a large sum if they exit the business before they die.

Each business owner must meet the underwriting requirements for their specific life insurance policy coverage. The proceeds from the insurance may force the company to issue a dividend or pay a retained earnings tax.

One-Way Buy-Sell Arrangement

If you’re a sole proprietor or have a single shareholder corporation, a One-Way Buy-Sell Arrangement can be designed to provide the business owner with a willing buyer in the event of retirement, disability, or death. This will typically be a key employee, another business entity in a related market or industry, or a family member that you want to inherit and continue managing the business.


The legal complexity and tax consequences of buy-sell arrangements means you’ll need professional advice to select and structure an appropriate agreement.

Seek the advice of an attorney, tax adviser, and financial professional.

  • MassMutual financial professionals have helped thousands of business owners with their business transfer needs. You can count on us to answer your questions.
  • Contact your MassMutual financial professional today.

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1 Access to cash values through borrowing or partial surrenders will reduce the policy's cash value and death benefit, increase the chance the policy will lapse, and may result in a tax liability if the policy terminates before the death of the insured.

The information provided is not written or intended as specific tax or legal advice. MassMutual, its subsidiaries, employees and representatives are not authorized to give tax or legal advice.
Individuals are encouraged to seek advice from their own tax or legal counsel.

Insurance products issued by Massachusetts Mutual Life Insurance Company (MassMutual)
(Springfield, MA 01111) and its subsidiaries, C.M. Life Insurance Co. and MML Bay State Life
Insurance Co. (Enfield, CT 06082).C.M. Life Insurance Co. and MML Bay State Life Insurance Co., are non-admitted in New York.