You Just Sold the Business. Now What? A Founder’s Guide to the First 90 Days

The week after a sale closes is usually quieter than founders expect. The calls from the buyer’s counsel stop. The data room goes dark. There is a number in an account that did not exist a month ago, and for the first time in years, nobody needs a decision from you by Friday.

That quiet is useful. It is also where many of the expensive mistakes we see after a liquidity event begin.

Earlier this year I wrote about the planning moves worth making before a sale. This piece picks up on the other side of the closing table. It is written for the owner who has already signed and wants to use the next three months well.

What should you do in the first 90 days after selling a business?

Make very few irreversible decisions. The first 90 days are for securing the proceeds, understanding exactly what you received, and setting aside what you will owe. The investment strategy, the estate updates, and the larger lifestyle questions come next, and they go better when this groundwork is done first.

DAYS 1 TO 30 · SECURE AND ORGANIZE

1. Put the proceeds somewhere boring.

The right home for sale proceeds in the first few weeks is liquid, low risk, and dull. Treasury bills, a government money market fund, or bank deposits spread across institutions so balances stay within FDIC coverage limits are common choices. Each has trade-offs: money market funds are not FDIC-insured and can lose value, and yields on all of these options change over time. The goal here is not return. The goal is to buy yourself time to think without taking on more risk than necessary while you do.

2. Write down what you actually received.

The headline price in the announcement is rarely the number that lands. Between the purchase price and your account sit escrow and holdbacks, working capital adjustments, transaction fees, and sometimes an earnout tied to results you no longer fully control. Many owners also hold rollover equity in the combined company or shares of the acquirer.

I ask every founder we work with to build a one page inventory: cash received, cash still contingent, equity retained and its restrictions, and any consulting or employment terms that carry income. That page becomes the foundation for every decision that follows. If an earnout is part of the deal, I suggest treating it as possible income rather than certain income until it is actually paid.

3. Set aside the tax before you feel wealthy.

The tax on a sale is often due well after the money arrives, which makes it easy to treat the gross proceeds as spendable. They are not. Work with your CPA to estimate the federal and state liability, confirm whether estimated payments are needed this year, and move that amount into its own account. For New Jersey residents, capital gains are taxed at the same state rates as ordinary income, so the state share of a large gain deserves its own line in the plan.

4. Check your insurance and liability coverage.

A sale changes your risk profile in ways that are easy to miss. Coverage that once sat with the company, from liability policies to life and disability insurance, may have ended at closing. At the same time, newly liquid wealth can make you a more visible target for claims. A review of umbrella liability, personal coverage, and how accounts are titled belongs in the first month, not the first year.

DAYS 31 TO 90 · PLAN BEFORE YOU INVEST

What are the most common mistakes after a liquidity event?

In our experience, the costly ones fall into four patterns. None of them involve poor judgment, and all of them are easier to avoid than to unwind.

Moving too fast.

Within weeks of a sale becoming known, the opportunities arrive: a friend’s company raising a round, a real estate project, an investment pitched as built for exactly your situation. Some may be worth considering. Almost none need an answer this month. A useful rule is that no new commitment gets made until the overall plan exists.

Treating the number as the plan.

A large balance can hide a simple problem: the paycheck stopped. For many owners, the business covered salary, benefits, a vehicle, and a range of expenses that now come out of personal accounts. Before deciding how much is enough, it helps to know what your life actually costs without the company underneath it.

Staying concentrated by default.

Selling the business often reduces concentration risk without removing it. Rollover equity, acquirer stock, or a large stake in a single new investment can leave much of your net worth tied to one outcome again. That can be a deliberate choice. It should not be an accidental one.

Leaving the estate plan where it was.

Most estate documents were drafted when the bulk of an owner’s wealth sat inside an illiquid company. Liquid wealth behaves differently, passes differently, and may call for different structures. A plan that was reasonable last year may now direct assets in ways nobody intended.

How do you decide what the sale proceeds are for?

Before choosing investments, give the money jobs. I find it helps to sort the proceeds into four purposes, each with its own time horizon and its own tolerance for movement.

The first is income: the amount that replaces what the business used to pay you, for as long as you need it. The second is reserve: a cushion that lets you ride out a difficult market or an unexpected expense without selling at the wrong time. The third is long term growth: capital that will not be touched for a decade or more and can be invested accordingly. The fourth is family and giving: what you intend to pass on, give away, or set aside for the people and causes that matter to you.

The proportions are different for every family, and they will shift over time. What matters is that each dollar has a job before it has an investment. When that is true, the portfolio decisions tend to follow from the plan rather than from the market headlines of the month you happened to sell.

How do you diversify concentrated stock after a sale without a large tax bill?

There is rarely a single answer, but there is a consistent approach: model the full position, then reduce it in deliberate steps rather than all at once. Common tools include staging sales across more than one tax year, pairing gains with losses realized elsewhere in the portfolio, and giving appreciated shares rather than cash to charity or to a donor advised fund. Lockup periods and trading windows often set the pace before taxes do.

This is where an analytical lens earns its keep. The right path depends on how the position is likely to behave, how much of your plan relies on it, and what you would owe at each step. Putting those three things on one page usually makes the decision clearer than any rule of thumb.

How should your estate plan change after selling a business?

Start by reviewing the basics with fresh eyes: wills, trusts, powers of attorney, and every beneficiary designation. Then look at the questions new liquidity raises. Should some of the proceeds move to the next generation now rather than later? Does a charitable vehicle make sense? Who would manage this money if you could not?

For New Jersey families, the state’s inheritance tax rules for certain beneficiaries are worth understanding as part of that review. Your estate attorney leads the drafting. Our role is to make sure the documents and the financial plan describe the same intentions.

Why does selling a business feel harder than expected?

I come to this work through numbers, so I will say it plainly: the spreadsheet is often the easier part. Owners who have run a company for twenty or thirty years tell us the hardest adjustment is not financial. It is waking up without a team to lead, a problem to solve, or a calendar someone else is filling.

That matters to the plan. Founders who feel unmoored are more likely to make fast decisions simply to feel useful again. Giving yourself a season before committing to the next venture, board seat, or investment is a planning decision as much as a personal one.

Who should be on your team after a liquidity event?

At minimum, your CPA, your estate attorney, and an advisor who coordinates between them and keeps the whole plan in view. The problem we see most often is not bad advice from any one professional. It is three capable professionals working from three different pictures of your situation. One shared plan, reviewed together, closes most of those gaps.

At Tilson Financial Group, our planning team includes a CPA, CFP® professionals, and a CFA charterholder, which lets us work through the tax, planning, and investment questions in the same conversation.

If you want a second read

If you have recently sold a business, or expect to close in the coming months, we are glad to walk through your one page inventory with you and talk about what comes next. Our Liquidity Event Planning Framework is a good place to start on your own. When you want a conversation, real people answer the phone at our office in New Providence, New Jersey.

This material is for informational and educational purposes only and is not personalized investment, tax, or legal advice. The strategies discussed may not be appropriate for everyone, and results depend on each person’s circumstances. Tax laws are subject to change. Consult your own tax and legal advisors regarding your situation. Tilson Financial Group, Inc. is an SEC-registered investment adviser. Registration does not imply a certain level of skill or training.

Frequently asked questions

What should I do with the money right after selling my business?

Keep it liquid and low risk while you plan. Treasury bills, government money market funds, and insured deposits spread across banks are common short term homes. The priority in the first weeks is protecting the proceeds and giving yourself time, not earning a return.

When is tax due after selling a business?

The gain is generally reported on the return for the year the sale closes, but estimated tax payments may be required during that year to avoid penalties. Earnouts and installment terms can shift timing. A CPA should estimate federal and state liability as soon as the deal closes.

How long should I wait before investing the proceeds from a business sale?

There is no fixed rule. Many owners choose to hold proceeds in low risk accounts until a written plan covers spending needs, taxes, and estate goals. For most, that takes weeks to a few months. The goal is to invest on purpose, not on a deadline.

How do I reduce concentration in acquirer stock or rollover equity?

Most owners reduce a concentrated position in stages. Common approaches include spreading sales across tax years, offsetting gains with losses elsewhere, and gifting appreciated shares to charity. Lockups and trading windows often set the timeline. The right pace depends on your plan and tax picture.

Do I need to update my estate plan after selling my business?

Usually, yes. Estate documents written when wealth sat inside a private company may not fit liquid assets. Review wills, trusts, powers of attorney, and beneficiary designations, and revisit gifting and charitable goals with your estate attorney and financial advisor. Changes in liquidity often change the right structure.

What is a liquidity event?

A liquidity event is any transaction that converts an illiquid asset, such as a privately held business or company equity, into cash or tradable securities. Common examples include a business sale, a buyout, an IPO, or the vesting and sale of stock compensation.

Is an IPO a liquidity event?

Yes. An initial public offering converts private company shares into publicly tradable stock, which makes it one of the most common liquidity events. Lockup periods and trading windows usually determine when those shares can actually be sold, so planning often starts before the proceeds are accessible.