Here is the version of closing day most owners imagine: the wire lands, the champagne opens, and then, finally, there is time to figure out what to do with the money. That version is the problem. By the time the money arrives, every important decision about it should already be made. The first 90 days aren’t a planning period. They’re the first quarter of a plan that already exists.
Why so many owners regret selling
The Exit Planning Institute, which trains and certifies exit planners, has cited the same number for years: of owners who succeed in selling their business, about three in four experience “profound regret” within a year. Nobody should treat the exact figure as gospel; the original survey’s method was never published in detail. But ask anyone who works with owners after a sale and the pattern is familiar.
It is rarely the price. The regret comes from things that were never planned:
The identity went with the company
For decades the business decided what Monday looked like, who called, and who needed you. Then it stopped. Nobody replaced it.
The money wasn’t what they thought
Taxes, escrows, earnouts and fees turned the headline price into a smaller number, and nobody had shown them the real one in advance.
The family wasn’t ready
Promises made in the excitement of the deal, children who heard the number from someone else, and no plan for who gets what, or why.
The buyer changed things
Long-time employees, customers and the culture they built, handled in ways they didn’t expect and can no longer influence.
None of those get fixed in the 90 days after closing. Every one of them can be addressed in the year before it. In EPI’s 2023 national survey, only 41% of owners had a formal, written plan for what they would do after selling. Half had an informal one, which is a polite way of saying it lived in their head.
What should already be decided before the wire
A planned sale arrives at closing with these answered, in writing, with a name next to each one:
| Area | What’s already settled | Why it can’t wait |
|---|---|---|
| Taxes | The estimated federal and New York bill, where the reserve sits, and when each payment goes out | Elections and structure decisions happen at signing, not after |
| The money’s jobs | The spending reserve, the tax reserve, near-term goals, and a written plan for building the long-term portfolio | Decisions made in closing week are made under the worst conditions |
| Gifts and giving | Shares given to family or charity before the deal was set; amounts for later gifts decided | The best gifting moves expire before the purchase agreement |
| The estate | Wills, trusts and beneficiaries rewritten for cash instead of a company | Documents built around business shares may not fit a balance sheet |
| Risk | Liability coverage resized for visible wealth; health coverage after the company plan | Coverage gaps open the day the company is gone |
| Security | A verified, phone-confirmed wire procedure agreed with the closing attorney and the custodian | Fraud targets the exact week money moves |
| The owner | The role with the buyer, the transition period, and what the months after it are for | This is where most regret starts |
| The team | CPA, estate attorney and wealth advisor working from one action list, with owners and dates | Without one list, things fall between three offices |
This is the real work of exit planning. Not a pitch book, not a valuation. A plan for the money, the family and the owner, finished while there is still time to act on it. Our guide to giving the proceeds clear jobs walks through the money side.
The first 90 days, mapped
When the plan exists, the first 90 days look less like a scramble and more like a checklist being worked. Here is the shape of it.
| When | What happens | Who owns it |
|---|---|---|
| Closing week | The wire is confirmed by phone against instructions agreed in advance. Proceeds are reconciled to the closing statement line by line. The tax reserve moves where the plan said it would go. | Wealth advisor and CPA, with the closing attorney |
| Weeks two to four | The portfolio starts getting built on the schedule set before closing. Planned gifts and grants go out. The estate attorney confirms the documents match the new balance sheet. | Wealth advisor and estate attorney |
| The first team meeting | CPA, attorney and wealth advisor in one room, checking the plan against the actual numbers and updating one action list. | The whole team |
| Month two | Estimated tax payments checked against what actually came in. Insurance changes confirmed in force. Escrow, earnout and adjustment dates on the calendar. | CPA and wealth advisor |
| Month three | The first full review: what arrived against what was expected, what changed, and what gets adjusted. The family meeting where the plan is explained. | Wealth advisor and the family |
Wire fraud is the one risk that doesn’t care how good your plan is. Deals get announced, and criminals read the same announcements you do. A spoofed email with “updated wire instructions” is the classic play. The FBI’s 2025 Internet Crime Report counted about $3 billion in reported business email compromise losses, second only to investment fraud. In a planned sale, the instructions are agreed and verified by phone long before closing week, and nobody acts on a change that arrives by email.
What’s still moving after closing, and already on the calendar
The headline price was never the number that hits the account on day one. In a planned sale, every remaining piece is known in advance, with a date and a risk attached.
| Piece | What it is | When it usually resolves |
|---|---|---|
| Indemnity escrow or holdback | A slice of the price held back to cover the buyer’s claims if something promised in the agreement turns out wrong | Commonly 12 to 18 months after closing |
| Working capital adjustment | A true-up comparing the working capital delivered at closing against the agreed target | Usually within a few months, and it can go either way |
| Earnout | Price that depends on the business hitting future targets after you’ve lost control of it | One to several years, if ever |
| Seller note | Price paid over time by the buyer, on credit | On the note’s schedule, subject to the buyer paying |
| Rollover equity | Ownership in the buyer’s company instead of cash | When the buyer sells, often years later |
SRS Acquiom, which administers thousands of private-company deals, publishes the norms each year. In its latest study, the median indemnity escrow was 10% of the price in deals without representations-and-warranties insurance, and 0.5% in deals with it. More than 90% of deals included a purchase price adjustment, and roughly a quarter included an earnout. A plan that spends the headline number is a plan built on money that may never arrive.
What the 90 days are actually for: real numbers
A good plan is built on estimates. The first 90 days replace them with facts, and the plan adjusts. That is the only kind of decision-making the first quarter should involve.
- The final working capital adjustment, and what it does to the cash.
- The actual tax bill, once basis, allocation and state questions are settled with the CPA.
- The real terms of escrow releases and earnout measurements, read against the calendar.
- How the owner actually feels about the days, which no spreadsheet predicts.
The tax bill has a timing advantage, and the plan uses it. For federal estimated taxes, paying at least 100% of last year’s total tax on time (110% if last year’s income was over $150,000) generally avoids the underpayment penalty even when this year’s tax is far larger, and a sale late in the year can use the annualized income method. New York uses a similar test. In a planned sale, the CPA has already decided which payments go out when, and the reserve earns until it’s due.
What still gets a no
A sale makes you visible. Everyone you know will suddenly have an idea for your money. In a planned sale, the answer to most of them is already written down:
- The private deal your friend can get you into, but only this week
- Annuities, insurance policies or anything with a surrender period that isn’t already in the plan
- Loans to family outside the amounts the family already agreed on
- Announcing the number. To anyone.
“It’s not in the plan” is a complete sentence. It is also a far easier one to say than “let me think about it.”
The part most owners skip: you
Nobody warns you about the first Monday. No calls, no decisions, nobody waiting on you. This is where the regret statistic lives, and it is the part of exit planning most owners skip because it doesn’t involve a spreadsheet.
Decided before closing: what your role with the buyer is and when it ends, what the months after it are for, which boards or ventures you will and won’t take on, and how much of your time belongs to family. Owners who answer those questions in advance are choosing a next chapter. Owners who don’t are just waiting for one.
Health coverage has a clock. COBRA can usually extend the company plan for up to 18 months. Owners 65 or older have a separate deadline: Medicare generally gives eight months after work or the employer coverage ends to sign up for Part B without a lifetime penalty, and COBRA doesn’t stretch that window. In a planned sale, that date is on the calendar before the last day of work.
How Morrowgate handles this. At Morrowgate, the first 90 days are written down before closing: every reserve, every gift, every deadline, and who owns each one. Greg runs the closing-week reconciliation with your CPA, keeps the family balance sheet current from day one, and brings your CPA and attorney together in the first month to check the plan against real numbers. Client accounts sit in your own name at Fidelity, or Schwab where preferred. The wire should be the least eventful part of the sale.
Questions owners ask
What if the sale already closed and nothing is mapped out?
Then the first 90 days become the planning period, and the order matters: secure the accounts, reconcile what arrived, set the tax money aside, and make nothing irreversible until the plan exists. It’s recoverable. It’s just slower and more expensive than doing it before closing.
How far before closing should the planning start?
Ideally a year or more. Some of the most valuable moves, like gifting shares or confirming QSBS, only work before a buyer is at the table. At the latest, before a letter of intent is signed.
When are federal estimated taxes due?
Generally April 15, June 15, September 15 and January 15 of the following year, with adjustments when a date falls on a weekend or holiday.
Is the earnout money mine to plan around?
Plan around it as a possibility, not a promise. Earnouts depend on targets you no longer control. Families that treat them as upside avoid the worst surprises.
Where this guidance stops
This article is general education on the period right after a business sale: how the rules and the options generally work. It is not tax, legal or investment advice, and nothing here is a recommendation for your situation. Rules change and outcomes turn on the facts, which is why a CPA and an attorney look at a family’s own numbers before anything is done.
Sources
- Exit Planning Institute: Vision statement citing owner regret after a sale
- Exit Planning Institute: A decade of owner readiness research
- SRS Acquiom: Deal Terms Study
- FBI Internet Crime Complaint Center: 2025 Internet Crime Report
- IRS: Underpayment of estimated tax by individuals penalty
- IRS: Form 2210 and instructions (annualized income installment method)
- Medicare: COBRA coverage and Part B