How do I compare offers to buy my business?

Establish what each proposal is actually buying

Check the business perimeter, ownership percentage, retained assets and whether the quoted value is enterprise or equity value. Identify cash, debt and debt-like treatment, the working-capital target and adjustment process. Mintz identifies these and other deal terms as matters to examine at the letter-of-intent stage. ^[1]

Ask for a bridge from the headline to estimated equity consideration and then to expected closing cash. List unresolved definitions beside the calculation rather than burying them in a footnote. If the buyer will price the deal after further diligence, make that assumption visible. Two offers cannot be compared fairly if one includes the property or assumes more working capital and the other does not.

Keep different forms of consideration separate

For an earnout, examine the metric, measurement period, accounting definitions, buyer operating discretion, reporting rights and dispute process. A maximum earnout is not assured proceeds. Holland & Knight’s October 2026 drafting discussion explains why those details matter. ^[2]

With rollover, ask what entity and security you would own, its economic priority, minority rights, dilution exposure and exit or repurchase terms. Goodwin highlights these issues and notes that tax treatment depends on structure. Do not assume you receive the same economics or control as the buyer. ^[3]

See why the highest headline may not tell the whole story

Assume these proposals acquire the same existing 100% interest, with enterprise-to-equity adjustments already reconciled. Offer A’s rollover is a continuing investment in the post-transaction ownership structure. Taxes, fees and other obligations are excluded. The illustration does not value the rollover, estimate the earnout’s probability or assume escrow release. It is not a recommendation between offers.

Offer A has the larger stated headline, but less cash at closing and more future exposure. Offer B still requires examination of the escrow and all other terms. Ask what you need to receive, what risks you would retain and what must happen for the proposed value to become available.

Compare the route to closing and your responsibilities afterward

Ask what funding and approvals are in place, which conditions remain and what happens if a source of funding fails. A buyer’s expression of confidence is different from documented funding arrangements, and a commitment may itself contain conditions. Have the transaction team examine the documents and the allocation of risk in the proposed agreement. ^[4]

Review exclusivity, closing conditions, representations, indemnities and other continuing liabilities with counsel. Ask which obligations could exceed a stated holdback and which matters might allow a party not to close. The practical question is what you would agree to, not whether a term sounds customary.

Discuss your role after the sale and the buyer’s intentions for employees, management, location, brand and customers. Separate an expressed intention from an enforceable commitment, and ask counsel what can be documented. The Liberty Cedar transaction includes the owner’s account of cultural fit.

Use one comparison sheet and mark the unknowns

An unknown is not automatically a reason to reject a proposal. It is a question to assign and resolve before relying on the comparison. Ask the relevant advisors to explain assumptions and examine the actual proposal together.

The IRS distinguishes tax treatment for different assets and ownership interests. Compare relevant after-tax outcomes with your tax advisor using the proposed structure, not one assumed tax rate applied to each headline. ^[5]

For a first discussion with ThirdSide, describe the situation and the questions to resolve. Agree a suitable exchange process before sending confidential proposals or detailed financial records.