Insurance & Protection
Size the life insurance needed to fund a buy-sell agreement, and compare cross-purchase vs entity redemption.
Insurable interest (per owner)
$999,900
Additional coverage needed
$999,900
Cross-purchase policies
6
Cross-purchase, per policy face
$499,950
6 policies (n × (n − 1))
Entity redemption, per policy face
$999,900
3 policies owned by the entity
Cross-purchase requires n * (n - 1) policies; entity redemption uses n policies owned by the business.
If you own a piece of a business with other people, a buy-sell agreement is one of the most important legal documents you will ever sign. It answers a simple, painful question in advance: what happens to your share of the company if you die, become disabled, get divorced, or want out. Without a buy-sell, your family could end up as unwanted business partners of your co-owners, and your co-owners could end up in court negotiating with your spouse.
A written buy-sell is a promise. Life insurance turns that promise into cash on the exact day it is needed. When an owner dies, the policy pays the death benefit, typically tax-free, to whoever is set up to buy the shares. That party writes a check to the family in exchange for the deceased owner's interest. The business keeps operating, the family gets fair value, and nobody has to borrow.
In a cross-purchase, each owner personally buys a policy on every other owner. When an owner dies, the surviving owners use the proceeds to buy the deceased owner's shares directly. The upside is that the survivors get a stepped-up basis on the shares they buy, which reduces tax on a future sale. The downside is the number of policies. Two owners need 2 policies. Three owners need 6. Four owners need 12. It grows quickly with the formula n times (n minus 1).
In an entity redemption, the business itself owns one policy on each owner. When an owner dies, the business collects the death benefit and uses it to redeem the shares. This structure needs only n policies and is much simpler administratively. The tradeoff is that the surviving owners do not get a stepped-up basis on the redeemed shares, which can cost them tax later.
Two owners? Cross-purchase is usually the cleaner answer. Four or more owners? Entity redemption or a trusteed cross-purchase is usually more practical. Three owners is the classic borderline case. The right answer depends on the age spread, tax situation, and legal preferences of the group. An attorney and a tax advisor should sign off.
The policy face on each owner should equal that owner's insurable interest: total business value multiplied by that owner's ownership percentage. Undersize it and the survivors are still short. Oversize it and premium dollars are wasted, and you can create tax and valuation issues. Review the number every few years as the business grows.
Insurance is only half the job. The buy-sell agreement itself has to be up to date, with a defensible valuation formula or a scheduled appraisal. Many old agreements list a value from a decade ago that has nothing to do with the current business. Revisit the agreement any time the numbers, the owners, or the tax law materially change.
Educational estimates only. Not financial, tax, or legal advice.