Situations · The business sale

You sold the business. Don't let the tax bill enjoy it first.

The wire hit, and the number is bigger than anything you've managed before — and so is the tax exposure. The window to do something about it is short, and it mostly closes at year-end. This is the moment coordinated planning earns its keep.

What's actually at stake

The clock starts the day you close.

Most sellers meet their CPA in April — after every good option has expired. The difference between planning before year-end and after it is usually measured in six figures.

01

The capital gains bill is not fixed yet

Installment structure, timing across tax years, loss harvesting, and state residency questions all still move the number — but only before deadlines pass. After that, the bill is just the bill.

02

Charitable intent is worth the most right now

If giving is part of your plans at all, a donor-advised fund or charitable vehicle funded in the sale year deducts against your highest-ever income. The same gift next year is worth a fraction as much.

03

The proceeds need a job

Cash after a sale tends to sit — or get spent on the first exciting thing. A written plan gives every dollar an assignment: income now, growth later, reserves always.

04

Your estate plan is suddenly out of date

The documents written when the company was illiquid probably don't fit a liquid eight-figure balance sheet. Exemptions, trusts, and titling deserve a fresh look before the next tax year.

How Cannon helps

One table: investments, tax, and what it's all for.

Our CPA-led tax strategy team and your advisor work the same plan — so the reinvestment strategy, the tax moves, and the estate documents stop contradicting each other. Fee-based, fiduciary, no products.

Common questions

People in this spot usually ask.

How long do I have to reduce taxes on my business sale?
Some decisions must happen before the sale closes; most of the rest close at year-end of the sale year. The sooner planning starts — ideally before the letter of intent — the more options stay open. If you've already closed, there is usually still meaningful ground to cover before December 31.
Should I invest the proceeds all at once?
It depends on the plan, not on a rule of thumb. What matters first is separating money with a near-term job (taxes, reserves, planned purchases) from long-term capital — then investing the long-term portion deliberately rather than reactively.
What is a donor-advised fund and why does everyone mention it after a sale?
A donor-advised fund lets you take a charitable deduction in your highest-income year while granting the money to charities over time. In a sale year, that timing difference can be worth a great deal — which is why it comes up in nearly every post-sale plan where charitable giving matters to the family.
Do you work with my existing CPA and attorney?
Yes. We coordinate with the professionals you already trust — and our in-house tax practice can carry the strategy work if you'd rather have it all at one table.

Educational only — not investment, tax, or legal advice. Every situation is different; the right answer depends on the numbers, and that's what the strategy session is for.

Start here

One conversation. No pressure, no pitch.

Sit down with a fiduciary — not a salesman — and leave with a complimentary strategy for your exact situation, whether or not you ever hire us.