What Happens After the Exit Wire Clears?

Honestly, it was kind of jarring how quiet it got.

I spent twenty years building Vala Secure. When we sold it in 2022, I stayed on a few months for the transition. Most of my responsibilities were already delegated, so it was mostly oversight. Then it ended. No more phone calls. No meetings. No tasks assigned. Nobody waiting on a decision from me.

Just me, alone with the same questions every morning. What do I do from here? What's my purpose now?

Nobody warns you about that part. The money's the easy part. The quiet's a lot harder to explain.

After twenty years of tight cash, I finally had something I hadn't had in a long time: real liquidity. Money that wasn't owed to payroll, a vendor, or next quarter.

A mentor told me to take a year off and not do anything. It was good advice and bad advice. Good, because the quiet is when owners rush a big decision just to feel busy again. Bad, because a year off isn't a plan. The calendar can sit empty. The cash still needs a job.

That liquidity felt precious. It also didn't last long. Which is why this week's tip comes before anything else: before you spend or lock up any of the exit cash, decide how liquid you need to stay, including cash set aside for taxes. Once that money goes into something illiquid, getting it back to cash is hard and slow.

The number one issue after selling wasn't what to buy. It was the tax bill. I wanted to move the proceeds in a tax-efficient, mindful way, so I spent a lot of time learning nuances of the tax code and researching real estate, crypto, private investments, oil and gas, and the stock market.

In the end, I bought a commercial building. Part of the logic was the tax side. Bonus depreciation, combined with a cost segregation study, can pull a large share of a building's deductions into the early years. On paper, that's attractive (and helped my tax bill).

In practice, I ended up asset-rich and cash-poor. The deductions were real. The liquidity was gone. A building can be a fine asset. But it's not a checking account.

This isn't a story about real estate being good or bad. It's a story about sequence. The tax play came before the liquidity plan.

Most owners spend years cash-poor inside the business. The exit is the first real chance to fix that. The common miss is converting the exit right back into the same shape: big, illiquid, and hard to get out of.

A deduction lowers what you owe. It doesn't put cash in the account for a new venture, a year off, a kid's tuition, or a market that goes sideways.

After the sale, you're not just an owner anymore. You're managing a pool of capital. Allocators start with one question: how much of it should stay liquid?

And as I’ve stated before - The entrepreneurial brain is way different than the investor brain.

Put the liquid side first: living needs for the next chapter, a cushion for the unexpected, and the cash set aside for taxes. Your CPA sizes the tax piece. Then look at your net worth balance sheet and track the ratio of liquid to illiquid assets. In plain English: how much could you get to in a month if you needed it, versus how much is tied up? Start early, and check it often. Once cash goes illiquid, it's hard to get back to cash quickly.

How much liquidity is enough depends on what comes next.

If you're starting another company, liquidity is runway. The household keeps living while the new venture isn't paying you yet, and the venture itself needs a cushion.

If you're stepping back, liquidity is the bridge. It covers living years without forcing a sale of long-term assets at a bad moment.

Same exit. Different answer. That's why the next chapter has to be named before the cash gets locked up.

One thing I'd do differently: hold off on major six- or seven-figure purchases in the first year after the sale. A building, a big private deal, a second home. The quiet makes those decisions feel urgent. Most of them can wait until the plan is clear.

That's not a rule for everyone, and waiting isn't a promise of a better outcome. It's a way to avoid locking yourself into an illiquid spot the way I did with the building.

Bonus depreciation and cost segregation rules change, and they depend on facts your CPA has to own. What happens on a later sale, including depreciation recapture, belongs in that same conversation. If the tax bill is your number one issue after the sale, start there with your CPA, before anything gets bought to solve it.

Skyrise doesn't give tax advice. We help owners coordinate the personal wealth side: how much capital stays liquid and for how long, how the liquid vs illiquid mix on the balance sheet holds up over time (in plain English, what you could get to in a month versus what's tied up), and how the pieces fit before anything gets locked up.

Take these to the kitchen table with your spouse or significant other, the person who shares the consequences:

Once the quiet settles and the liquid side is set, the bigger questions show up. You don't have to answer them alone:

• What comes next? 

• Do I still need to work?

• What’s my purpose now?

• How should I think about taxes?

• Is the rest of my financial house in order?

• What does my projection for the rest of life look like around money?

Those questions come next. Your CPA owns the tax side. Your attorney owns the legal side. A fee-only adviser can help coordinate the rest so the pieces fit together.

The quiet comes first. Sit with it before you make a big move. Then think like an allocator: set the liquid side, tax cash included, before anything gets locked up. Let your CPA own the tax mechanics, and get help with the questions that come next.

If you want a plain look at how we help owners organize their financial world after a sale, read our Services page, where you can Book a Fit Call.

(General education and personal reflection from Skyrise Financial, a Colorado fee-only registered investment adviser. Registration does not imply a certain level of skill or training. Brad's commercial building purchase is a personal illustration only, not a recommendation to buy real estate or to pursue bonus depreciation, cost segregation, or any tax strategy. Holding off on major purchases in the first year is a general educational idea, not a rule or a recommendation for any individual. Tax rules change and depend on individual facts. Skyrise does not provide tax or legal advice or prepare tax returns. This is not personalized financial, tax, or legal advice and not a promise of any outcome. Investing involves risk, including possible loss of principal. Consult your CPA and attorney as needed.)