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Buy-Sell Agreement vs Cross-Purchase Agreement: What Business Owners Need to Know

May 18, 2026 | Podcasts

What is a buy-sell agreement and why is it important for business owners?

A buy-sell agreement outlines how a business owner’s ownership interests will be handled in scenarios like retirement, death, or disability. It specifies the terms for purchasing the owner’s shares or membership interests, ensuring a smooth ownership transition. This agreement is crucial for business continuity and clarity in ownership changes.

How does a cross-purchase agreement differ from a buy-sell agreement?

A cross-purchase agreement is a type of buy-sell agreement where fellow owners in a company purchase the shares of a departing owner. The key difference is that in a cross-purchase agreement, the purchasing parties are other owners within the company. This setup allows for direct ownership transfer among co-owners.

Who typically buys the ownership interests in a buy-sell or cross-purchase agreement?

In scenarios like retirement, winning the lottery, divorce, death, or disability, the remaining owner or owners usually buy out the departing owner’s shares. This process is facilitated by a pre-agreed upon buyout amount and terms outlined in the buy-sell or cross-purchase agreement to ensure a smooth transition of ownership.

How is life insurance utilized in funding a buyout transaction in these agreements?

Life insurance can be used to fund a buyout transaction by providing a source of capital for purchasing a departing owner’s shares. Each owner can take out a life insurance policy on the other owner(s), ensuring that in the event of death, the insurance proceeds can be used to buy out the deceased owner’s shares, facilitating a seamless transition in ownership.

Are there any potential downsides to using insurance in cross-purchase agreements?

One potential downside of using insurance in cross-purchase agreements arises when there are multiple owners involved, leading to a complex arrangement with several insurance policies to manage. In such cases, larger companies might opt for a company-owned insurance policy instead to simplify the process and avoid complications.

What are the alternatives to using insurance for funding a buyout transaction?

While insurance is a common and preferred method for funding buyout transactions, other alternatives include borrowing from private lenders or institutions. However, borrowing from traditional lenders like banks might not be feasible in certain cases, making insurance the primary choice for ensuring a secure and efficient ownership transfer.

What are the tax implications of different ownership transfer methods in these agreements?

One significant tax difference lies in the step-up in cost basis benefit that owners receive when using insurance to fund a buyout. With insurance-funded buyouts, owners get a step-up in basis, reducing capital gains taxes upon selling the business later on. On the other hand, when the company buys the shares, owners do not receive this step-up in basis, potentially resulting in higher capital gains taxes.

How do control and ownership change with a cross-purchase agreement compared to an entity purchase agreement?

In a cross-purchase agreement, the purchasing owner’s ownership interest increases as they buy out the departing owner’s shares directly. Conversely, in an entity purchase agreement, where the company buys back the shares, the remaining owners’ ownership interests are adjusted proportionally, without any increase in ownership relative to other owners.

How are buy-sell and cross-purchase agreements typically created and when are they used?

Buy-sell and cross-purchase agreements are created as standalone contractual documents that outline the terms of ownership transfer in various scenarios. These agreements are usually established after a company has been formed and matured. Cross-purchase agreements are commonly used for smaller companies with fewer members, while entity purchase agreements (redemptions) are preferred for larger companies with more capital and complex ownership structures.

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