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You check your account. The wire came through.
$8 million. $15 million. $50 million. Maybe more. Years of blood, sweat, and tears, embodied by a single transaction.
A medley of feelings typically ensue: relief, euphoria, and then an overwhelming urge to do something. Buy a lake house. Pay off your parents’ mortgage. Invest in your friend’s startup. Splurge just because you can.
And while your newly liquid wealth likely can afford many extravagant and generous purchases, the first few months after a liquidity event are categorically consequential. People tend to hastily, sometimes emotionally, make life-changing decisions without the right infrastructure in place.
Let’s map out the first 90 days after a business sale: what to do immediately, what can wait, and what should be avoided entirely.
Why the First 90 Days Are So Critical
You just closed the biggest financial transaction of your life. Adrenaline, relief, exhaustion, and euphoria aren’t synonymous with clear thinking.
You wouldn’t make major business decisions after pulling an all-nighter. But post-sale, many founders treat wealth decisions casually.
Then there’s the pressure. Financial advisors, insurance brokers, private equity funds, real estate agents, family members, friends with “opportunities” — everyone wants a piece of your attention and your money.
“This deal won’t last.”
“Rates are about to change.”
“You need to act now.”
Without a framework, it’s easy to say yes just to stop the noise. While building wealth calls for speed and conviction, preserving it is predicated upon patience and discipline. Consider the following steps to help create structure, protect against reactive decision-making, and thoughtfully evaluate opportunities during the first 90 days after a liquidity event.
Days 1-30: Assessment and Team Building
You’ll likely spend your first month understanding your new financial reality and assembling the right advisory team, if you haven’t already.
Calculate Your After-Tax Net Worth
There’s a material difference between sale proceeds and after-tax proceeds. A $10 million sale might net $6.5 to $7.5 million after taxes, depending on deal structure and state.
Work with an accountant to calculate federal capital gains tax, state tax, Net Investment Income Tax, and any other applicable taxes. Understand what you’ll owe and when.
Update (or Create) Your Estate Plan
Beneficiary-designated accounts, such as retirement accounts and life insurance policies, do not pass according to the terms of your will. If they’re outdated or nonexistent, fix them now.
Your will and trust documents may need updating. Powers of attorney for both financial and healthcare decisions should be current. You may also want to explore revocable trusts for probate avoidance and privacy, as well as irrevocable trusts for wealth transfer.
If your net worth now exceeds estate tax exemption thresholds (currently $15 million per individual in 2026), you should consider working with an estate planning attorney and financial advisor who specializes in high-net-worth clients.
Hire or Upgrade Your Advisory Team
This is the time for a coordinated team, not siloed advisors.
A financial advisor or wealth advisor builds your investment strategy and coordinates your overall financial plan. An accountant or tax professional handles tax planning and models scenarios. An estate planning attorney updates documents and structures wealth transfer.
Red flags when vetting advisors: pushy sales tactics, unwillingness to collaborate with other advisors, lack of transparency on fees, promises of guaranteed returns.
Build a Preliminary Financial Plan
This doesn’t need to be perfect yet. Planning is a process not a product. It’s a working draft.
- What are your goals for your wealth? Lifestyle experiences, wealth transfer, charitable giving.
- What’s your cash flow need? Annual spending, near-term large purchases.
- What’s your risk tolerance and time horizon?
Conduct a Spending Stress Test
Model different spending scenarios. What if you spend $300,000 per year? $500,000? $1 million? How long does the money last under each scenario?
This helps set realistic expectations and prevents lifestyle inflation from eroding wealth faster than anticipated.
Days 30-60: Strategic Tax and Estate Planning
Once your advisory team is assembled, which is likely by the second month, you can execute time-sensitive tax and estate planning moves. Some founders move faster and tackle these in the first 30 days. The key is having the right advisors in place before you act.
Offset Capital Gains With Strategic Charitable Giving
If you haven’t already, consider donor-advised funds to offset capital gains from the sale. And if you donate appreciated assets like stock or real estate instead of cash, you avoid capital gains and get a full charitable deduction.
You could also front-load multiple years of charitable giving in a high-income year to maximize deductions. This would need to happen in the same tax year as the sale to offset gains.
Execute Tax-Efficient Roth Conversions (If Applicable)
If you have traditional IRA or 401(k) balances, consider converting to Roth in a low-income year. Post-sale, if you’re not working, this may be an optimal window.
By paying income taxes at lower rates, you can then enjoy tax-free compound growth in a Roth IRA and not taxes are due upon withdrawal. Coordinate with your accountant to avoid pushing yourself into higher brackets though.
Make Estimated Tax Payments
Federal and state estimated taxes are due quarterly. Missing deadlines triggers penalties. Your accountant should calculate what you owe and when.
Review and Update Insurance Coverage
With higher net worth, you may need more umbrella liability protection — consider having coverage that matches your net worth less retirement accounts. Consult with a trusted advisor to discuss how much coverage is recommended for your situation.
Life insurance may no longer be necessary if your estate is now self-insured. Unless you may need it for estate planning strategies. Disability insurance is likely no longer needed if you’re financially independent. Long-term care insurance is worth considering if you’re in your 50s or 60s and want to protect assets.
Days 60-90: Selective Action and Long-Term Positioning
By day 60, you should have a plan and a team. Now you can start executing, but selectively.
Build Your Diversified Portfolio
Work with your investment advisor to design a personalized asset allocation. Diversification across asset classes — stocks, bonds, real estate, alternatives — reduces risk without sacrificing long-term returns.
Avoid the temptation to “put everything to work” immediately. Staged investing can help reduce timing risk.
Address Concentrated Positions (If Applicable)
If you have rollover equity from the sale or other concentrated stock positions, build a diversification plan. It’s typically unwise to liquidate everything at once (the tax hit is severe) but don’t leave 70% of net worth in one stock either.
Strategies include staged selling, exchange funds, options strategies, and tax-loss harvesting.
Set Up Cash Flow and Liquidity Management
Determine how much cash you need accessible for near-term spending (typically 12 to 24 months of expenses). Establish a systematic withdrawal strategy if you’re no longer working.
Keep enough liquidity so you’re not forced to sell investments at inopportune times.
Begin Exploring Future Ventures
If you want to invest in startups, real estate deals, or other entrepreneurial ventures, use the 90-day period to research opportunities (not commit). Create a separate “venture allocation,” which could be 5% to 10% of your investable net worth.
What to Avoid Entirely in the First 90 Days
Some financial decisions should wait.
Don’t make large purchases. Wait until you’ve seen the full tax liability and built a financial plan before purchasing real estate, cars, boats, or other discretionary assets. Premature purchases can lead to liquidity constraints and regret.
Don’t invest in friends’ or family members’ businesses. Emotion and obligation are terrible investment criteria. If you want to support them, wait six to twelve months and treat it as a gift versus an investment.
Don’t lend money to anyone. Loans to family or friends usually end badly. If you want to help, make it a gift with no expectation of repayment.
Don’t commit to long-term illiquid investments. Private equity funds, real estate syndications, hedge funds with lock-ups — you likely don’t yet know your liquidity needs. No need to lock up capital prematurely.
Don’t hire advisors based on relationships alone. Your friend’s brother-in-law who’s a financial advisor may be a great guy, but you need competence and coordination. Vet advisors professionally: check credentials, ask for references, understand fee structures.
Don’t make large gifts to family without a plan. Gifting $500,000 to each of your kids sounds generous, but it can inadvertently raise expectations, evoke potential resentment among siblings, and trigger tax complications. Wait until you’ve worked with an estate attorney to structure transfers thoughtfully.
Don’t rush into philanthropy without strategy. Charitable giving is wonderful, but there’s no reason to do it hastily. Use the 90 days to clarify your philanthropic goals, research organizations, and structure giving tax-efficiently.
The 90-Day Checkpoint: Building the Foundation of Your Future
A sale is worth celebrating. But you worked this hard to achieve such a coveted milestone. Now it’s time to build the system that protects what you’ve accomplished.
At Simon Quick Advisors, we help business owners navigate exits with clarity and confidence. As your dedicated wealth advisor and planning quarterback, we coordinate your CPA, estate attorney, and investment team to help sequence wealth management decisions and position you for a fulfilling next chapter.
Is a sale on the table (or even in progress)? We’re happy to talk — one conversation today can change your life.
Disclaimer
This material is provided for informational and educational purposes only and should not be construed as investment, legal, accounting, or tax advice, or as an offer to sell or solicitation of an offer to purchase any security or investment advisory service. Any references to planning strategies, investment opportunities, or market conditions are general in nature and may not be appropriate for your individual circumstances.
Simon Quick Advisors & Co., LLC (“Simon Quick”) and its representatives do not provide legal or tax advice and are not a law firm or certified public accounting firm. Simon Quick does not prepare tax returns. Clients and prospective clients should consult their attorney, accountant, or other qualified professional regarding their specific legal, tax, and financial circumstances before implementing any strategy discussed herein. Insurance products and services are not offered through Simon Quick.
Investing involves risk, including the possible loss of principal. Past performance is not indicative of future results, and there can be no assurance that any investment strategy will achieve its intended objectives. Alternative and illiquid investments involve additional risks and may not be suitable for all investors. Diversification and asset allocation strategies do not guarantee profit or protect against loss.
Certain statements contained herein may constitute forward-looking statements, which are based on current expectations, estimates, and assumptions that are inherently subject to change and uncertainty. Actual results may differ materially from those anticipated.
Information contained herein has been obtained from sources believed to be reliable; however, Simon Quick does not independently verify and makes no representation or warranty as to the accuracy or completeness of such information.
Simon Quick Advisors & Co., LLC is an SEC-registered investment adviser headquartered in Morristown, New Jersey. Registration does not imply any level of skill or training. Additional information about Simon Quick, including its Form ADV Part 2A, is available upon request or through the SEC’s Investment Adviser Public Disclosure website.
