Written by , CEO & Founder, Timeless AI™ · Published 20 September 2026

Buy-sell agreements: cross-purchase vs entity purchase, valuation clauses, and funding with insurance

What happens to a co-owner's shares when they die or cannot work, how the agreement fixes the price and the buyer, and how insurance funds it so the family is paid and the business survives.

General information, not advice.

The problem: the widow as your new business partner

Two partners own a firm. One dies. His shares pass under his will to his wife, who now owns half of a business she has never worked in, needs the income from, and cannot sell to anyone but the surviving partner, who cannot afford them. Every outcome from there is bad for both: a forced sale at a discount, a dividend policy fought over at every board meeting, or a lawsuit. The buy-sell agreement is written the day before, when both partners are alive and can agree.

Structures compared

Cross-purchase

Entity purchase (redemption)

Hybrid or trust-owned

Who buys

The other owners personally

The company buys back the shares

A trust or insurance LLC holds the policies; the company or the owners buy as the agreement directs

Policies

Each owner insures each other: with four owners, twelve policies

The company insures each owner: one policy per owner

One set, held by the trust or LLC

Tax basis

Buyers get a stepped-up basis in the shares bought (US), so less gain on a later sale

Remaining owners' basis unchanged; and after the US Supreme Court's 2024 decision in Connelly v United States, company-owned life insurance is counted in the company's value for estate tax without deducting the redemption obligation, which raised the estate tax on the deceased owner's shares

Avoids the Connelly problem and the policy-count problem; more to set up

Best for

Two or three owners

Many owners; simplicity; non-US companies without the Connelly issue

Larger or family-owned firms; US companies since 2024

The valuation clause

The price is the fight. Options: a fixed value reviewed annually (and never reviewed, so the price is a decade stale), a formula (a multiple of earnings or revenue, updated each year end), or an independent valuation at the trigger (fair, slow, expensive, and argued over). Most well-drafted agreements use a formula with an independent valuation as the fallback, require the owners to sign the annual number, and set a floor equal to the insurance in place. The tax authorities in the United States, Canada and Australia will not accept a buy-sell price as the estate value unless it was arm's length and binding in life as well as at death, so the formula has to be defensible.

Funding with insurance: a worked example

Two owners, 50% each, business valued at US$4 million. Under a cross-purchase agreement each insures the other for US$2 million. On the first death the survivor receives US$2 million tax-free, pays it to the estate for the shares, and owns 100% with a US$2 million basis in the shares bought. The widow has cash instead of half a company. The premiums, perhaps US$4,000 a year each for ten-year term at forty-five, are the cost of that certainty. Disability cover on the same terms covers the trigger that is statistically more likely before sixty-five, and is the cover most agreements forget: a disabled partner who cannot work and cannot be bought out draws a salary from a business the other partner is now running alone.

Triggers beyond death

Permanent disability, divorce (so an ex-spouse cannot end up an owner; the agreement gives the company or the other owners a right to buy any shares awarded in a property settlement), bankruptcy, retirement, departure, and, in some agreements, a "shotgun" clause for deadlock. Each needs a price and a funding source; insurance covers the first two, and an instalment plan over three to seven years with security over the shares usually covers the rest. Good-leaver and bad-leaver pricing (full value for retirement, a discount for a breach) is standard in shareholders' agreements and belongs here too.

Where the agreement lives

In the shareholders' agreement or the partnership deed, cross-referenced by the company's constitution, with the policies listed in a schedule and the insurer told the agreement exists. The will should leave the shares to the estate or a trust, not to a named person, so that the agreement can operate; a will that leaves the shares to the widow directly creates the problem the agreement was drafted to avoid. In Australia, the family trust that usually owns the shares needs the agreement to bind the trustee; in the United States, S-corporation status needs the buyer to be an eligible shareholder.

The agreement fixes the price

It does not say what the founder thought the business was for, or what she would have said to the buyer. That can be kept.

Insurers, lawyers and advisers: Make an enquiry

Frequently asked

What is a buy-sell agreement?+

A contract among business owners fixing who buys an owner's interest on death, disability or departure, at what price, funded how.

Cross-purchase or entity purchase?+

Cross-purchase for two or three owners (better tax basis in the US, and no Connelly problem); entity purchase for many owners outside the US; a trust or insurance LLC for larger US firms.

How is the price set?+

Usually a formula reviewed each year, with an independent valuation as the fallback at the trigger.

What did Connelly v United States decide?+

That life insurance a company holds to redeem a deceased owner's shares counts in the company's value for US estate tax, without deducting the redemption obligation, so the deceased's shares are worth more and taxed more. Cross-purchase or trust-owned structures avoid it.

Written and reviewed by , CEO & Founder, Timeless AI™

Published 20 September 2026

Chris Williams is the founder and CEO of IDY Pty Ltd, the company behind Timeless AI and its sibling brand Afterlife AI. He writes about personal AI, digital identity, and how people can build a living AI self they own and govern.

Buy-sell agreements: structures, valuation, funding | Timeless AI