How an Exit Planning Roadmap Actually Works: 18 Months Before, 6 Months Before, Day Of

Most business owners spend years building something valuable and then compress all the financial planning into the last 90 days before closing. That compression is expensive. The tax decisions you can no longer make after a letter of intent is signed will cost more than almost anything else in the deal.

Here is what a disciplined exit timeline actually looks like.

18 to 24 Months Out: Get the House in Order

This is the period most owners skip entirely because a sale feels abstract. It is also where the most money is made or lost.

Three things belong on your list at this stage. First, get a formal valuation. Not a back-of-napkin multiple, but a written opinion from a qualified business appraiser. It tells you what you are working with and surfaces gaps in documentation that a buyer will find anyway. Second, clean up your books. Owner perks, related-party transactions, and inconsistent add-backs all compress your multiple in due diligence. Fixing them now gives you 12 to 24 months of clean financials to present. Third, review your entity structure. An S-corp election, a reorganization into a holding company, or a trust ownership change can meaningfully shift how sale proceeds are taxed. The Soil layer of the plan, meaning how your ownership is structured and where income lands for tax purposes, is almost impossible to rearrange once a buyer is at the table.

6 to 12 Months Out: Build the Team and the Room

At this stage, the sale is real. You need a CPA who does M&A work, an M&A attorney, a financial advisor who understands post-liquidity planning, and in many cases an investment banker or broker depending on deal size.

You also need a data room: three to five years of tax returns, financial statements, customer concentration analysis, contracts, and key-employee agreements. Buyers who find surprises in diligence either walk or reprice. Neither outcome is good.

This is also the moment for family conversations. If your spouse, adult children, or aging parents are part of your financial picture, they need to know a liquidity event is coming before it happens. Estate planning documents, beneficiary designations, and titling decisions take time to execute properly.

90 Days Out: Last Moves Before the Clock Stops

Once you sign a letter of intent, most tax planning windows close. The 90 days before signing are the final opportunity to act.

A few specific moves to consider. Pre-sale Roth conversions can make sense if your taxable income will spike in the year of sale and push you into a bracket that makes future conversions prohibitively expensive. Charitable bunching, including a contribution to a donor-advised fund, lets you accelerate deductions into a high-income year. If you hold appreciated assets outside the business, reviewing their location and timing before the liquidity event matters. These are the Harvest-stage decisions that determine how much of your sale price you actually keep.

The 2026 annual gift tax exclusion is $19,000 per recipient. If wealth transfer to family members is part of your plan, the 90-day window is a good time to confirm those gifts are documented and funded.

What to Do This Week

Pull your last three years of tax returns and financial statements and ask yourself one question: would a sophisticated buyer have questions about any line on these documents? If the answer is yes, you still have time to clean it up. Start there.

The information provided is for educational purposes only and does not constitute investment, legal, or tax advice. Consult with qualified professionals for guidance specific to your situation.