The First 90 Days After Exit

Part of Running a Family Office Under $100M

The wire hits. The number in your account has more digits than feels real. You refresh the screen a few times to make sure it's actually there.

Now what?

The first 90 days after a liquidity event are strange. They're when founders make their best and worst decisions. The pressure to do something is enormous—from advisors, from friends, from your own restlessness. But most of the big mistakes I've seen happened in this window, made by smart people who moved too fast.

This post is about managing those 90 days. What's actually urgent. What can wait? What you should actively avoid.

Strange Period

Nobody prepares you for how weird it feels.

For years, maybe a decade, your net worth was mostly theoretical. Equity on a cap table. A number that your accountant updates occasionally. Real in some legal sense, but not real in the sense of being able to do anything with it. You couldn't buy groceries with your Series B shares.

Now it's cash. Real, liquid, spendable cash. And the psychological adjustment takes longer than people expect.

Some founders feel euphoria. Finally, validation. The risk paid off. They want to celebrate, buy things, tell people.

Others feel anxiety. The number is large but finite. What if they lose it? What if they make mistakes? The responsibility feels heavier than the opportunity.

Many feel a strange emptiness. The thing they worked toward for years has happened. Now what? The goal that structured their days is gone. The identity that came from building is suddenly past tense.

All of these responses are normal. Research backs this up. A UCSF and UC Berkeley study found that 72% of entrepreneurs report mental health concerns—significantly higher than the general population. Rates of depression, anxiety, and ADHD run 2–3x higher among founders than in the broader workforce. Transition out of a business amplifies these vulnerabilities.

Exit Planning Institute's 2023 research is even more striking: roughly 70% of business owners who sold their company reported they 'deeply regretted' the decision within a year. Not because the deal was bad. Because they weren't prepared for who they'd be afterwards.

You can see the patterns. Euphoric founders commit to three angel deals and a vacation property in the first month. Anxious ones freeze, unable to make any decision, while opportunities pass. Empty ones start a new company immediately, not because it's the right move, but because they can't stand the stillness.

I'm not a therapist. I can't tell you how to feel. But I can tell you this: the first 90 days are not the time for major decisions. The psychological ground is shifting. Your judgment isn't what it normally is. The best thing you can do is create space to stabilise before you commit to anything significant.

Week 1: Secure the Cash

The first week is about one thing: making sure the money is safe and accessible. Nothing fancy. Nothing optimised. Just secure.

Where should the cash sit? Somewhere boring. A major bank with proper protections. In the UK, the FSCS covers £120,000 per person per institution—increased from £85,000 in December 2025. For temporary high balances from a business sale, you may qualify for up to £1.4 million of protection for six months under FSCS rules. In the US, FDIC covers $250,000. If you've just received $15 million, the vast majority isn't protected by deposit insurance at any single bank.

This doesn't mean you need to open 60 bank accounts. But it does mean you should think about where the money sits.

A few options for the initial parking spot:

Government money market funds hold short-term government securities. Your cash isn't technically a 'deposit', but it's backed by government obligations. Very safe, very liquid, currently paying 4–5%.

Treasury bills directly—you can buy these through most brokerages. 4-week, 8-week, 13-week maturities. Backed by the government. Liquid.

Split across multiple banks if you want deposit insurance coverage. Two or three major institutions, each under the insurance limit. More hassle but more protection.

High-yield savings at a major bank works fine, too, understanding the insurance limits. In the UK right now, the best easy-access accounts are paying 4.25–4.50% AER. Notice accounts (90–120 days) push slightly higher.

The goal for week one isn't optimisation. It's not finding the best yield or the smartest structure. It's just making sure the money is somewhere safe while you figure everything else out. A few basis points of yield difference don't matter. Having the money accessible and protected does.

One thing to avoid: don't put it all in a brokerage account and start buying things. Not yet. The temptation is there—money sitting in cash feels like waste. But you have work to do before you deploy anything. Let it sit.

Weeks 2–4: Triage Your Obligations

Once the cash is secure, figure out what you actually owe.

The exit itself probably triggered tax obligations. Depending on structure, jurisdiction, and how the deal was done, you might owe capital gains tax, potentially income tax on certain components, and maybe state or local taxes if you're in the US. In the UK, Business Asset Disposal Relief (formerly Entrepreneurs' Relief) caps CGT at 10% on the first £1 million of qualifying gains—but that's a lifetime limit, and anything above it faces standard CGT rates of 18% or 24% depending on your income. The amount could be substantial—20% to 40% of the proceeds isn't unusual across different jurisdictions.

This is urgent to understand, even if payment isn't due immediately. The worst outcome is spending or committing money you'll need for taxes. I've seen it happen. The founder receives $10M, commits $3M to investments and a house deposit, then discovers they owe $3.5M in taxes. Suddenly, they're scrambling for liquidity they don't have.

Talk to a tax advisor in the first two weeks. Not to do complex planning—there's time for that later. Just to understand what you owe and when. Get a number. Set that money aside mentally. It's not yours to deploy.

Beyond taxes, what other obligations exist?

Debts. Do you have a mortgage, business loans, personal loans? You don't have to pay these off immediately—we'll talk about that decision. But know what they are.

Commitments. Did you promise investors you'd roll proceeds into a new fund? Commit to a real estate deal that's closing soon? Have earnout components that affect your behaviour? List everything you're obligated to.

Family. Are there promises you made—explicit or implicit—about what you'd do after exit? Helping parents, funding education, supporting a sibling? These aren't legal obligations, but they're real.

Write it all down. What's owed, to whom, when. Then you know what you're actually working with. The balance in your account, minus obligations, is your real starting point.

Month 2: Start the Conversations

Now you can start talking to people about what comes next. But the sequence matters.

Tax advisor first. Before wealth manager, before investment platforms, before anyone who wants to manage your money. The structural decisions—what entities to use, how to hold assets, what jurisdiction considerations matter—affect everything downstream. Making investment decisions before you've sorted out the structure can lead to unwinding later.

Find someone who specialises in high-net-worth individuals, ideally with experience in founder situations. Not your startup's accountant, unless they've grown into this kind of work. Ask other founders who've been through exits. The big accounting firms have private client practices. Boutique firms specialising in entrepreneurs exist. Either can work—what matters is relevant experience.

The initial conversation isn't about implementing complex strategies. It's about understanding your situation and options. What structure makes sense given your residency, family situation, and goals? What should you be thinking about? What decisions need to be made soon, and which can wait?

Estate solicitor second. While tax and structure conversations are happening, engage someone on estate planning. Yes, you probably won't die soon. But the documents should exist, and some structural decisions (like trusts) intersect with both tax and estate planning. Getting these conversations running in parallel makes sense.

Then—and only then—wealth managers or investment platforms. Once you understand the structure and have basic documents in place, you can think about where and how to invest. Not before.

This sequence frustrates wealth managers who want your assets immediately. They might suggest you're losing returns by waiting. The math doesn't support their urgency. Vanguard's research shows that even if lump-sum investing beats dollar-cost averaging 68% of the time, the median difference is modest—a few hundred dollars per $100,000 over a year. A month or two of cash returns while you sort structure costs almost nothing. A structural mistake because you deployed before you understood your situation can cost enormously.

Month 3: Stabilise, Don't Optimise

By month three, you should have:

• Cash is secure and accessible
• Tax obligations understood and reserved
• Tax advisor engaged and structure conversations underway
• Estate solicitor working on basic documents
• Starting to think about investment approach

What you shouldn't have: a fully deployed portfolio, multiple fund commitments, a new property, significant illiquid investments.

Month three is about stabilisation, not optimisation. The goal is a functional foundation. Structure decisions are made or nearing completion. Basic documents done. A clear picture of what you have and what you owe. Maybe start deploying into simple, liquid investments for the core portfolio.

The pressure to do more is real. Advisors want to show progress. Friends are asking about your plans. You might feel behind compared to founders who seem to have it all figured out.

Ignore this pressure.

The cost of cash sitting for another month or two is minimal. High-yield savings or money market pays 4–5%. If your long-term expected return is 7–8%, the 'cost' of waiting is 2–3% annualised. On $10M, that's maybe $25,000 per month of delay. Real money, but not compared to the cost of a mistake.

A $500K commitment to the wrong fund because you rushed? A structural error that creates a $200K tax liability? A property purchase that locks up the liquidity you need? These cost multiples of what the waiting costs.

Stabilise first. Optimise later. There's time.

What NOT to Do

The first 90 days are as much about what you don't do as what you do.

Don't commit to illiquid investments. PE funds, venture funds, real estate syndications, direct deals. These can all be sensible eventually. They're not sensible when you've had money for six weeks and haven't sorted the basic structure. You'll have plenty of opportunities later. The deals that require you to commit immediately, right now, this week—let them pass. There will be others.

Don't restructure aggressively. Complex offshore structures, elaborate trust arrangements, multi-jurisdictional setups. Maybe these make sense for your situation. Maybe they don't. You can't know yet because you haven't done the work to understand. Advisors who push for immediate, aggressive restructuring are serving their interests, not yours.

Don't buy the house. Or the car, or the boat, or the art. I'm not saying never. I'm saying not now. Large lifestyle purchases in the first 90 days tend to be emotional. You're buying the feeling of having made it. That feeling fades. The asset remains. Wait until the psychological ground stabilises before making big purchases.

Don't angel invest in your friends' startups. The requests will come immediately. Everyone knows you have money now. Some opportunities will be legitimate. Most won't be. And you can't evaluate them properly when you're still adjusting to your own situation. Create a polite standard response: 'I'm not making any investment decisions for the next six months while I get my situation sorted. Happy to talk after that.'

Don't hire an army. Family office director, full-time accountant, personal assistant, investment analyst. You don't know what you need yet. Hiring creates obligations. Employees are hard to unwind. Get through the first six months with existing advisors and contractors. Add permanent staff only when you understand what functions actually require it.

Don't tell everyone. The more people who know about your exit, the more requests, pitches, and complications you get. There's no obligation to broadcast. Close friends and family, sure. But the broad network doesn't need to know your numbers.

The first 90 days are about protecting optionality. Every commitment closes doors. Every decision uses bandwidth you don't have much of right now. The goal is reaching day 90 with the cash secure, the obligations understood, the foundation started, and the options still open.

Saying no is the main job.

90-Day Checklist

By day 90, aim to have these done:

• Cash secured in appropriate accounts
• Tax obligations from exit are understood and quantified
• Tax advisor engaged with relevant experience
• Structure conversations underway (holding company, etc.)
• Estate solicitor engaged
• Basic estate documents drafted or in progress
• Insurance reviewed for obvious gaps
• Cybersecurity basics in place (hardware keys, etc.)

These started but are not necessarily complete:

• Structure implementation
• Investment approach defined
• Wealth manager or platform evaluated (if using one)
• Core portfolio beginning to deploy

These were deliberately deferred:

• Illiquid commitments (PE, VC, real estate)
• Complex restructuring
• Major lifestyle purchases
• Hiring permanent staff
• Angel investments
• Optimisation of anything

What Comes After

Day 90 isn't the finish line. It's the point where the foundation should be stable enough to build on.

Months 4–6 are when the structure gets implemented, the core portfolio deploys more fully, and you start evaluating the satellite opportunities that will come later.

Months 6–12 are when you might make first illiquid commitments, once you understand your liquidity and have a portfolio framework that makes sense.

Year two is when optimisation happens. Refinements to structure. Building out the alternative portfolio. Sophisticated planning.

This trajectory assumes you're moving at a reasonable pace. Some founders move faster because their situation is simpler or they have relevant experience. Some move more slowly because life is complicated, or they need more time to adjust. Both are fine.

What matters is recognising that the first 90 days are a specific phase with specific priorities. Not the time for optimisation. Not the time for aggressive deployment. The time to stabilise, understand, and protect your options.

The decisions you make in the next few years will compound for decades. The decisions you make in the first 90 days will shape whether those years go well or poorly.

Move slowly. Say no. Let it be boring.

The exciting part comes later.

Playbook Hub: Running a Family Office Under $100M

Related guides:

• Pre-Exit Wealth Planning
• Auditing Your Existing Setup
• The Minimum Viable Setup
• The One-Page Framework