The founder transition guide

Bring both teams into the conversation

Your transaction work and personal planning have different questions to answer. Prepare a list for the professionals involved: what closes when, what is paid later, which decisions belong to the company, and which affect you personally? Ask who will keep the shared list current and raise unresolved items before a deadline.

Distinguish price from proceeds

Identify cash at closing, debt repayment, transaction costs, escrows, earnouts, and retained or rollover interests. Enter only your own expected cash receipt in the worksheet. Do not count contingent payments as cash already available. The tax treatment of a business sale depends on the facts and the assets involved; the IRS describes why a sale can involve multiple asset classifications.⁷

Make reserves explicit

Work with your tax professional to estimate the reserve appropriate to your situation. Our worksheet asks for a dollar amount you supply; it does not calculate tax or assess QSBS eligibility. Then identify personal commitments and near-term spending. The remaining number is a planning remainder, not a recommendation to invest that amount or a claim about your after-tax wealth.

Build the ongoing scope

Decide what help you want after the transaction: investments, cash planning, coordination with your attorney and CPA, family conversations, or reporting. Ask who would handle each responsibility and how outside costs are billed. Review advisory and investment fees together, using the actual assets covered by the proposal.²

Choose a relationship for the next chapter

Prepare questions about the advisor’s relevant experience, communication, conflicts, and continuity. Check registration and disciplinary information through the resources linked below.³ A substantial transaction does not by itself tell you which service model to choose. Use a clear list of decisions and responsibilities to evaluate whether the proposed team fits your life after the business.

Sources & further reading

Source pages reviewed September 2026. Worksheets use your inputs, not tax rates or provider quotes.