Selling a business is a planning problem before it is an investment problem. Charitable timing, entity structure, state residency, and proceeds allocation all have windows that close at signing. Planning that begins twelve to eighteen months ahead keeps those options open; planning that begins after the wire works with what remains.
Almost everything written for business owners about a sale is about the transaction: valuation, diligence, terms, deal counsel. That work is real and it is not ours. What tends to go unattended is the parallel track — what happens to the household, the tax position, and the family, all of which are decided by choices made long before closing.
The sequence below is the one we work through with families in Northern Virginia. Timings are typical rather than prescriptive; a deal that moves faster compresses the early stages rather than removing them.
The planning sequence
- 0118–12 months out
Establish the baseline
Total what actually depends on the company: equity, salary, deferred compensation, and often the mortgage. Model the household after a sale at a plausible range of outcomes, including one where the sale does not happen. Most owners have never seen the concentration written as a single number.
- 0218–12 months out
Settle charitable intent early
Contributing appreciated equity to a donor-advised fund or foundation before a sale is treated very differently from donating cash afterward. Whether it suits a family depends on their circumstances, but the option generally has to be exercised well ahead of a signed agreement, and it needs the CPA in the room.
- 0312–6 months out
Entity, titling, and residency
How the selling entity is structured, how ownership is titled between spouses or trusts, and which state the household is resident in at closing can each change the after-tax outcome. These are decisions for your deal counsel and CPA; our role is making sure they are raised while they are still open.
- 046–0 months out
Decide where proceeds go before they arrive
Write the investment policy before there is a balance to invest. A documented policy agreed in advance is considerably easier to hold to than one drafted in the weeks after a large deposit, when the pressure to act is highest and the reasoning is least clear.
- 05The first 12 months after
Do less than you expect to
The most common regret we hear is not a missed investment; it is a commitment — a property, a business, a gift — made in the first few months, before the family had settled what the wealth was for. Liquidity is easy to deploy and hard to reassemble.
- 06Year one onward
Bring the family into it
A sale is usually the point at which adult children learn the size of the number. Governance gives that a structure: a documented family narrative, a mission statement drawn from the values that built the company, and a meeting rhythm that keeps both in use.
Common questions
How far in advance should I plan for selling my business?
Twelve to eighteen months is a common working horizon, because that is roughly the window in which charitable timing, entity structure, titling, and residency can all still be adjusted. A faster deal compresses the sequence rather than removing it, but options that depend on acting before a signed agreement do close permanently at signing.
Should I donate stock before selling my company?
It depends entirely on the circumstances, and it is a decision for you with your CPA and counsel. What is generally true is that contributing appreciated equity to a charitable vehicle before a sale is treated differently from donating cash afterward, and that the option usually has to be exercised ahead of a signed agreement.
Who else should be involved besides a financial advisor?
Typically deal counsel, a CPA, and — depending on the structure — an estate attorney and a trust professional. Jason Howell Company coordinates with the professionals already engaged, and introduces independent ones where a family has a gap, receiving no commissions or referral compensation for any introduction.
This guide is provided for educational purposes by Jason Howell Company. It is general information, not investment, tax, or legal advice, and it does not account for any individual circumstances. Decisions described here generally require a CPA, an attorney, or both.