Your Situation
"I'm Selling My Business"
You built something real, and now you're cashing out. It's the financial event of a lifetime — and it comes with a tax bill and a short window to act. Suddenly every advisor in the country wants a meeting. Let's slow down and do this right.
The two things that sneak up on founders
The first is the tax. A lifetime of work can mean a seven- or eight-figure gain landing all at once — and a big slice of it heading straight to the IRS unless you've planned ahead. How the deal is structured — asset versus stock sale, how the price is allocated, whether part of it is a consulting agreement — can swing the tax bill by a startling amount, and most of that is decided before closing, not after.
The second is quieter: for the first time in years, there's no paycheck and no company to run. That cash has to become your income now, and that's a different job than building a business. We've watched founders who were brilliant operators feel completely at sea three months after the sale, because nobody ever helped them turn the lump sum into a paycheck.
The best time to talk about both is before the deal closes. Once the wire hits your account, some of the most powerful doors quietly close behind it.
What we help you think through
Defer the gain where the code allows
Opportunity Zone funds, installment sales, and charitable structures can defer — and sometimes reduce — the tax on a business sale, if we move inside the window.
Turn the proceeds into income
The paycheck is gone. We build a plan so the sale proceeds generate steady, durable income for the next chapter instead of slowly eroding.
Diversify out of one big bet
Your net worth was tied up in one company. Now’s the time to spread it thoughtfully across assets that don’t all move together.
Coordinate the whole team
Your CPA, your M&A attorney, your estate planner — we make sure everyone’s rowing in the same direction before and after close.
What this can look like
From operator to a paycheck that runs itself
Picture a founder selling the company they'd run for twenty-two years — an eight-figure deal, most of their net worth in one place. They called us during diligence, before terms were final, which made all the difference. "I know how to run the business," they told us. "I have no idea how to run the money."
Working alongside their M&A attorney and CPA while the deal was still being papered, we weighed in on the purchase-price allocation, mapped which portion of the gain could be deferred, and — crucially — built the after-sale income plan before the wire ever arrived. By closing day they weren't staring at a scary lump sum; they had a written plan for what each dollar was doing.
Pre-LOI
we were in the conversation while terms could still be shaped
3 advisors
CPA, M&A attorney, and us — rowing in the same direction
Day 0
an income plan was ready the moment the wire landed
Illustrative composite based on common client situations. Names, figures, and details are representative, not a specific client, and not a promise of results.
How a first conversation actually goes
Step 1
We start before the deal closes whenever possible
That’s when the most options are still on the table — deal structure, gain deferral, the works. Even a single conversation early can change the outcome.
Step 2
We listen first
What does the next chapter actually look like for you? Travel, a new venture, time with family, giving? The plan follows that — not a product.
Step 3
We coordinate with your existing team
Your CPA, M&A attorney, and estate planner stay central. We make sure nothing falls through the cracks during a busy, emotional stretch.
Step 4
No pressure, no pitch on day one
A sale of a lifetime deserves patience, not a sales sprint. We’re comfortable telling you to wait until the dust settles.
How we approach it
- We start before the deal closes whenever possible — that’s when the most options are still on the table.
- We listen first. What does the next chapter actually look like for you? The plan follows that, not a product.
- We coordinate with your existing team so nothing falls through the cracks during a busy, emotional stretch.
- No pressure and no pitch on day one. A sale of a lifetime deserves patience, not a sales sprint.
Questions we hear a lot
When should I start tax planning for a business sale?
Before a letter of intent is signed, ideally — and certainly before the deal closes. Some of the most powerful tools, like structuring the deal to qualify for installment treatment or setting up a trust, have to be in place before the wire hits. Once the proceeds land in your account, several doors quietly close. If you're even thinking about selling in the next year or two, that's the right time to talk.
How is the gain on a business sale taxed?
It depends heavily on the structure — asset sale versus stock sale, how the purchase price is allocated, and your entity type. Some of the proceeds may be long-term capital gain, some may be ordinary income (for example, depreciation recapture or a consulting agreement), and state tax sits on top. That allocation is negotiable during the deal, which is exactly why getting advisors involved before the terms are locked matters so much.
Can I defer the tax on my business sale the way you can with real estate?
Not with a 1031 — that's real-estate-only — but yes, there are paths. A Qualified Opportunity Zone investment can defer the capital gain portion if you reinvest within 180 days. Installment sales spread the gain (and the tax) across years instead of bunching it into one. Charitable remainder trusts can defer and reduce it while creating an income stream. The right one depends on your number and what you want next.
The paycheck is gone. How do I replace that income?
This is the part founders underestimate. For years your income came from running the company; now a lump sum has to become a durable, multi-decade income stream. We build a plan that turns the proceeds into reliable cash flow — blending income-producing investments with growth — so the sale funds the rest of your life rather than slowly eroding.
Every advisor wants a meeting. How do I know who to trust?
A sale brings the whole industry to your door, and the pressure can be intense. Our honest advice: slow down. Anyone pushing you to commit a large slice of the proceeds in the first few weeks is doing it for their reasons, not yours. A good advisor listens to what your next chapter looks like before recommending anything, coordinates with the CPA and attorney you already trust, and is comfortable telling you to wait.
Want the deeper how-it-works?
A quick, important note
This page is educational and general in nature — it isn't tax, legal, or investment advice, and it isn't a recommendation to pursue any specific strategy. The tax treatment of a business sale depends heavily on its structure and your individual facts. The strategies referenced are subject to specific IRS rules, deadlines, and qualification requirements, and all investments carry risk, including possible loss of principal. Please consult your own CPA, M&A attorney, and estate counsel before acting.
Thinking about selling? Talk to us first.
The earlier we're in the conversation, the more we can do. Tell us where you are in the process and we'll map out what's possible.
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