The First 90 Days After Selling Your Tech Company: A Founder's Playbook

You did it. After years of building, grinding, and betting on yourself, you sold your company. Whether it was a $2M acqui-hire or a $50M acquisition, you just had the biggest financial event of your life.

Now what?

This is the playbook I wish every tech founder had before their exit. The decisions you make in the first 90 days will determine whether your wealth grows or erodes over the next decade. I've seen founders lose 30-40% of their exit proceeds to avoidable tax mistakes and bad investments made in the excitement of a big payday.

Here's exactly what to do, week by week.

Week 1: The Emotional Rollercoaster (and Why You Should Do Nothing)

The "Now What?" Feeling Is Completely Normal

After years of your identity being wrapped up in your company, the sudden absence of that purpose hits hard. You might feel elated, lost, anxious, relieved, and bored all in the same day. This is normal.

Give yourself permission to sit with it. Take a vacation. Sleep in. Tell yourself that no financial decision needs to happen this week.

Do NOT Make Major Financial Moves Yet

Seriously. Don't buy a house, a car, or start angel investing in the first week. You're in an emotional state that leads to impulsive decisions.

The money isn't going anywhere. It can sit in a high-yield savings account earning 4-5% while you get your head straight.

The only action item for Week 1: if you received a wire or check, deposit it in a safe place. A high-yield savings account or money market fund at your bank is fine for now.

Days 7-14: Assemble Your Advisory Team

This is the most important step, and it needs to happen fast. You need three professionals, and ideally they should work together.

Tax Attorney (Not Optional)

A tax attorney is different from a CPA. You need someone who can advise on the legal structure of your deal, not just file your return. Key areas they'll help with:

Reviewing your purchase agreement for tax implications
Installment sale and earnout taxation
QSBS qualification (more on this below)
State tax nexus issues if you've worked in multiple states

Financial Advisor Who Understands Tech Exits

This is not the time for your uncle's financial advisor who specializes in retirement planning for teachers. You need someone who has worked with founders and understands:

Concentrated stock positions
Equity compensation structures
Tax-efficient investment strategies for sudden wealth
The founder psychology (risk tolerance, future ventures)

Estate Planning Attorney

If you don't have a will, a trust, and updated beneficiary designations, this is urgent. A $5M exit without proper estate planning could mean your family loses $2M+ to estate taxes if something happens to you.

Days 14-30: Understand Your Tax Exposure

Federal Capital Gains

How much tax you owe depends on how the deal was structured:

Stock sale vs asset sale. In a stock sale, you typically get capital gains treatment. In an asset sale, the allocation between different asset categories affects your tax rate.

Short-term vs long-term. If you held your shares for more than one year, you qualify for long-term capital gains rates (0%, 15%, or 20% depending on income, plus the 3.8% Net Investment Income Tax).

Installment sales. If you're receiving payment over multiple years, you can spread the tax liability across those years. This requires careful planning.

QSBS Exclusion (Section 1202): The Biggest Tax Break You Might Qualify For

This is the single most valuable tax provision for startup founders. If your company was a C corporation, and you held the stock for at least 5 years, you may be able to exclude up to $10 million (or 10x your cost basis, whichever is greater) from federal capital gains tax.

Requirements:

C corporation with gross assets under $50M at the time of stock issuance
Stock held for at least 5 years
Company must be in a qualified active business (most tech companies qualify)
Stock must have been acquired at original issuance (not secondary market)

If you qualify, this could save you $2-4 million in federal taxes on a $10M exit. This is not something to figure out on your own. Your tax attorney should evaluate QSBS qualification as their first priority.

State Tax Planning

Michigan has a flat 4.25% state income tax on capital gains. There's no special exclusion at the state level for QSBS (though some states do conform to the federal exclusion).

If you've been working remotely from multiple states, your tax situation gets more complex. Some states will claim a portion of your gain based on days worked in their jurisdiction.

Key consideration: if you're thinking about relocating to a no-income-tax state (Florida, Texas, Nevada), you generally need to establish residency BEFORE the sale closes for it to count. Moving after the sale won't help.

Days 30-60: Build Your Wealth Framework

Emergency Fund: 12 Months, Not 6

Most financial advice says keep 3-6 months of expenses in cash. After an exit, bump that to 12 months. Why?

Your income pattern has completely changed
You may not have regular paychecks for a while
You need a buffer to avoid selling investments at bad times
It gives you psychological freedom to make deliberate, not desperate, decisions

Diversification Strategy for Concentrated Wealth

If your exit was mostly stock in the acquiring company, you now have a concentrated position. This is one of the biggest risks to post-exit wealth.

The general guideline: no more than 10-15% of your total portfolio in any single stock. Getting there may take time due to lockup periods and tax considerations, but start planning the diversification path now.

A tax-efficient diversification approach:

Sell shares over multiple tax years to manage capital gains brackets
Use charitable giving (donating appreciated shares to a Donor-Advised Fund)
Consider exchange funds or other sophisticated strategies for very large positions
Invest proceeds in a diversified portfolio aligned with your risk tolerance and timeline

Real Estate, Index Funds, or Angel Investing?

Every founder gets pitched on angel investing after an exit. Before you write your first check, consider:

Index funds should be the foundation. Low cost, diversified, and they compound without any effort from you. 60-80% of your liquid wealth should probably be here.

Real estate can be a solid income-producing asset, but it's also illiquid and management-intensive. Don't buy a property just because you can.

Angel investing is high risk by nature. Set a firm budget (5-10% of liquid assets) and treat it as discretionary. Don't let FOMO drive you to over-allocate.

Days 60-90: Protect and Structure

Estate Planning Essentials

With a meaningful exit, you need:

Revocable living trust: Avoids probate and gives you control over asset distribution.
Pour-over will: Catches anything not in the trust.
Power of attorney and healthcare directive: Covers incapacity scenarios.
Beneficiary audit: Update every account, insurance policy, and retirement plan.

If your exit was over the federal estate tax exemption ($13.6M in 2026 for individuals, $27.2M for married couples), you need advanced strategies like irrevocable trusts, GRATs, or family limited partnerships. This is complex. Use an experienced estate attorney.

Insurance Review

Post-exit, your insurance needs change:

Umbrella insurance: Essential. $2-5M in umbrella coverage is inexpensive and protects against lawsuits.
Life insurance: May need to increase if your family now depends on investment income.
Disability insurance: Still relevant if you plan to work in any capacity.
Key change: You may no longer need employer-sponsored benefits. Evaluate marketplace or private insurance.

Charitable Giving Strategy

If philanthropy matters to you, the post-exit period is the most tax-efficient time to give.

Donor-Advised Fund (DAF): Contribute appreciated assets to a DAF in the year of sale for an immediate tax deduction. Then distribute grants to charities over time. This "bunches" your deductions into a high-income year when they're most valuable.

Charitable Remainder Trust: For larger exits, a CRT can provide you with income while reducing your tax bill and eventually benefiting charity.

The Biggest Post-Exit Mistakes I've Seen

Lifestyle inflation that eats the proceeds. A $5M exit sounds like a lot until you buy a $2M house, two cars, and furnish everything from scratch. Suddenly you've spent $3M and your "retirement fund" is $2M.

Investing in friends' startups. Saying no is hard. Set boundaries early.

Not paying estimated taxes. If you owe $500K in taxes and don't pay quarterly estimates, you'll owe penalties on top. Work with your CPA to set up estimated payments immediately.

Skipping estate planning. "I'll get to it" turns into years. Do it now while the motivation is fresh.

Going back to work too soon. Many founders jump into a new company within months, then burn out. Give yourself at least 90 days (ideally 6 months) before committing to a new venture.

Michigan Founders: Local Considerations

Michigan's startup ecosystem is growing fast, especially in Ann Arbor, Detroit, and Grand Rapids. A few Michigan-specific notes for post-exit founders:

Michigan's flat 4.25% tax applies to your capital gains. No special exclusion.
Detroit Renaissance Zones and other local incentives may apply if you reinvest in Michigan businesses.
Michigan Estate Tax: Michigan does not have a separate state estate tax (repealed in 2019). This is an advantage over states like New York, Massachusetts, and Oregon.
Angel investing locally: Michigan has a strong angel network (Michigan Angel Fund, Invest Detroit). If you want to give back to the ecosystem, these are reputable channels.

Your Next Step

The first 90 days after an exit are a window of opportunity. The decisions you make now compound for decades. Don't rush, but don't wait too long either.

If you're a tech founder who has recently exited (or expects to within the next 1-2 years), I'd love to help you build a plan. At Money Talk with Malik, we specialize in exactly this moment: helping tech entrepreneurs turn a one-time event into lasting wealth.