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Vanguard’s Advisor’s Alpha research found that good advice can add roughly 3 percentage points of value a year, on average — some years more, some years less. Most of that doesn’t come from picking better investments. It comes from things like not panicking during a downturn, choosing the right accounts, and drawing money out in the right order. It’s an industry estimate, not a guarantee.
Without one, transition deadlines pass silently: a Medicare enrollment window closes, a pension survivorship election locks by default, the withdrawal order gets set by whichever account was easiest to tap. With one, someone whose job is watching your deadlines catches these while they’re still movable — and keeps your CPA, attorney, and accounts working from the same plan.
What the relationship actually looks like, decision by decision →
Almost everything that determines what you keep from a sale is decided before the wire arrives — and most of it is fixed by the time the letter of intent is signed.
Structure drives the tax outcome. Whether the deal is written as a sale of assets or a sale of shares changes who owes what, and the buyer and seller usually prefer opposite answers. It is a negotiating point with a real price attached, so it belongs in the conversation early rather than being conceded as a technicality.
How you are paid matters as much as how much. Cash at close, an earn-out, a note, rolled equity — each carries a different risk and a different timing of tax. An earn-out that depends on the buyer running the business well is not the same asset as cash, and should not be counted as though it were.
Some shares qualify for treatment others do not. Depending on how the company was formed, how long you have held the stock and what the business does, part of the gain may be treated differently. The eligibility test is technical and it is checked against records from years ago, so it is worth asking well before a sale, not during one.
Charitable and family transfers have to happen first. Anything you intend to give away is generally best moved before the sale is binding. Once there is a signed agreement, the opportunity narrows sharply.
Then the concentration problem inverts. For years your wealth sat in one company. After close it sits in one pile of cash, usually with no plan, and the decision about what to do with it gets made under time pressure and unfamiliar pressure from people who suddenly want to help.
The advisor conversation worth having is the one before signing, when structure is still negotiable and the answer can still change the number.