The best planning happens before the sale closes
Once the deal is signed, most of the tax outcome is fixed. Structure, timing, and charitable strategy are all decided in the months beforehand — which is when to have this conversation, not afterward.
Who we serve
Selling the business converts something you controlled into something you have to manage.
One year, one large number, and the rest of your life to fund from it. The planning window around the sale is short and usually valuable.
What changes after a sale
A business sale concentrates years of value into a single taxable year, then leaves you funding a full retirement from liquid assets rather than from operating income. The tax consequences are largely set by decisions made before closing, and the income plan has to be built from scratch afterward.
- The tax year of the sale
- Often the highest-income year of your life. What you do before closing matters far more than what you do after.
- Deal structure
- An installment sale, an earnout, or seller financing spreads income across years and changes the whole picture. So does an asset sale versus a stock sale.
- Charitable timing
- If you give at all, a high-income year is when a deduction is worth the most. A donor-advised fund lets you take it now and give it out over time.
- Your income stops on closing day
- The operating income that funded your life disappears, and the portfolio has to replace it immediately rather than gradually.
What this complicates
Where the standard advice breaks down
Going from operator to income recipient is a real adjustment
You are used to a business that produced cash and responded to your decisions. A portfolio does neither. Building an income plan that behaves predictably matters more here than for almost anyone else.
A lump sum invites bad timing
Putting the entire proceeds to work at once, in whatever market exists that month, is its own version of sequence risk. Funding the near-term segments first and staging the rest removes the need to be right about the date.
Why us
Based in Colorado Springs. Working with clients across the country.
Colorado Springs has a deep base of owner-operated businesses, and the years around a sale are when planning is worth the most.
If you are nearby, you can come in and sit down with us. If you are not, we meet by phone or video call. Either way, when something changes, you reach someone who knows you.
Questions
Common questions
Before the deal is structured, ideally a year or more out. Once it closes, most of the tax outcome is locked. The months beforehand are when structure, timing, and charitable strategy can still change the result.
Rarely by avoiding it, usually by spreading and offsetting it. Installment structures, charitable giving in the high-income year, harvested losses, and how the deal is characterized all matter. Your CPA and attorney should be in the room for this.
Not usually. Fund the near-term income segments first so your paycheck is settled, then stage the longer-horizon money in. That removes the need to be right about what the market does the month your deal closes.
Then the plan should ring-fence the money that funds your life from the money you are willing to risk on the next thing. Keeping those genuinely separate is what lets you take the risk without it threatening your retirement.
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Executives with Concentrated Stock
You did not set out to hold this much of one company. It accumulated — and now selling has a cost, so it keeps growing.
Pre-Retirees, 55–65
This is the window where the decisions are still reversible and the numbers are finally real.
Retiring Without a Pension
This is the case the Next Phase Plan was built for — where every dollar of income beyond Social Security has to come from what you saved.
Let us find out what your portfolio can actually pay you.
Thirty minutes to see where your income will come from. If we are not the right fit, we will tell you.