Exit Strategy Archives - Keystone CPAs

October 15, 2026October 15, 2026Business, Economy, Finance, InvestmentMaggie Tredwell

If You Didn’t Show Up Tomorrow, What Happens to Your Business?

If You Didn't Show Up Tomorrow, What Happens to Your Business?

By Brian Wheeler, Director of Wealth Management & Business Brokerage

Business owners are busy. There is always a customer issue, an employee problem, a deadline, or another opportunity demanding attention. Somewhere further down the list may be updating the estate plan, reviewing the buy-sell agreement, or figuring out what happens to the business if something happens to you.

Important? Absolutely. Urgent? Usually not.

When Tomorrow Becomes Urgent

The problem is, when it finally becomes urgent, you may no longer be the one making the decisions. That may help explain why one widely cited business-owner study found that 68% of owners didn’t have a buy-sell agreement in place.

So here’s a question every business owner should be able to answer: If you didn’t show up tomorrow, what happens to your business?

If you have a partner, who owns your share?

Does your spouse suddenly become your partner’s new business partner?

Is there an agreement requiring your interest to be purchased, how is the value determined, and where does the money come from?

Maybe you already have life insurance intended to fund the purchase. That’s a great start, but is it enough based on what the business is worth today?

And do the insurance, buy-sell agreement and your estate plan all say the same thing should happen?

Having all three doesn’t necessarily mean you have a plan. The pieces have to work together.

A Continuation Plan for the Sole Owner

And if you’re the only owner, this may matter even more.

I once heard a group of business-planning attorneys give some pretty sobering advice about what a family should do when the sole owner of a business dies without a written and adequately funded continuation plan.

Their advice was simple: Don’t try to save the business. Sell the assets, preserve whatever value remains, and move on.

Their experience was that the odds of a family successfully stepping into an owner-dependent business without a plan were simply too small to justify risking more family money trying to keep it alive.

Think about that for a minute. A business you may have spent 20 or 30 years building could go from being one of your family’s largest assets to something they’re being advised to liquidate—simply because no one knew how to keep it going without you. A single-owner business may not need a traditional buy-sell agreement, but it absolutely needs a written continuation plan coordinated with the owner’s estate plan.

This isn’t really about creating more documents. It’s about protecting the value you’ve spent years creating—and the people who depend on it. Recent Gallup research found that among business owners without a long-term plan, 18% said they were simply too busy to think about the future. I suspect a lot of business owners can relate.

You spend an incredible amount of time protecting your equipment, cash flow, contracts, employees and customers. How much time have you spent protecting the business from the possibility that you aren’t there tomorrow?

Maybe the question isn’t whether you’re too busy to deal with it. Maybe it’s whether what you’ve spent a lifetime building is too valuable not to.

At Keystone Wealth Advisors, we help business owners coordinate the business, insurance, buy-sell or continuation planning, personal financial planning and estate planning so the pieces work together when they matter most.

concentration risk and having too much dependent on one asset.

September 24, 2026September 24, 2026Business, Economy, Finance, InvestmentMaggie Tredwell

Would You Put 80% of Your Net Worth in One Stock?

By Brian Wheeler, Director of Wealth Management & Business Brokerage

If you own a business, you may already have.

I heard an interesting comparison recently that got me thinking about the way business owners view their wealth. If you came into my office with 80% of your net worth invested in one stock, we’d probably have a conversation about risk. It could be a great company. You might know the company better than anyone and believe its best years are still ahead. But having that much of your financial future riding on one investment would still deserve some attention. Now let me change one thing. What if that investment is YOUR business?

When the “Stock” Is Your Business

For many successful business owners, that’s exactly what their personal balance sheet looks like. The business may represent the majority of their net worth, but the concentration often goes even further.

It may also provide their paycheck, bonuses and retirement contributions. They may own the building the company occupies. Their future retirement and financial independence may ultimately depend on what that business is worth when they’re ready to leave.

That’s a lot riding on one company.

Of course, there’s a good reason this happens. Concentration is often exactly how entrepreneurs create wealth. You put your time, money and energy into something you believe in, take risks other people aren’t willing to take, and hopefully build something valuable.

But creating wealth and preserving wealth aren’t necessarily the same thing.

Why Concentration Risk Matters

The problem with concentration is that you rarely worry about it when everything is going well. You notice it when something changes. A major customer leaves. Margins get tighter. A key employee moves on. The economy slows. A competitor changes the game. Or maybe nothing is wrong with the business at all. You simply reach a point where you don’t want to work this hard anymore.

That can be a difficult time to discover that your income, retirement and net worth are all tied to the same asset.

Taking Chips Off the Table

So, how do you take a few chips off the table without leaving the table?

If you owned a stock that had appreciated significantly over the years, you probably wouldn’t have to choose between owning all of it and selling all of it. You could sell some shares, diversify the proceeds and reduce your exposure while still participating in the company’s future growth.

A privately held business isn’t nearly that liquid, but I think the concept is worth considering.

Taking some chips off the table could be as simple as becoming more intentional about moving excess cash out of the business and building investments elsewhere. It might mean accumulating retirement assets, investments or real estate that aren’t dependent on the company. For other owners, it could eventually mean selling a minority interest, bringing in a strategic or financial partner, creating an employee or management ownership strategy, or completing a partial sale that provides some liquidity while allowing the owner to continue participating in the future growth of the company.

There isn’t one answer that works for every business owner, and taking chips off the table doesn’t necessarily mean you’re getting ready to sell.

In fact, I think the better time to have this conversation is long before you’re ready to sell.

Two Questions Worth Asking

Here’s a question I think every successful business owner should ask occasionally: if my business disappeared from my personal balance sheet tomorrow, what would be left?

Not because I expect that to happen. The answer simply tells us something about how dependent your financial future is on that one asset.

And there’s another question I think may be even more important: does my business have to be sold before I become financially independent?

If the answer is yes, that’s worth knowing now.

Building Wealth Outside the Business

At Keystone, we spend a lot of time helping business owners look at the relationship between the value they’re building inside their business and the wealth they’re building outside of it. We believe those are two very different things, and ideally, over time, both should be growing.

Your business may very well be the best investment you’ve ever made. The goal isn’t necessarily to change that. The goal is to reach a point where you continue to own the business because you want to, not because your financial future depends on it.

Maybe that’s what taking a few chips off the table is really about.

The Goal: Choice, Not Dependence

If most of your wealth is tied up in your business, you may not need an exit plan today. But it might be worth having a conversation about how you begin creating financial independence from the business long before you’re ready to leave it.

August 27, 2026August 27, 2026Business, Economy, Finance, InvestmentMaggie Tredwell

Is Your Business Holding Too Much Cash?

By Brian Wheeler, Director of Wealth Management & Business Brokerage

Having cash in the bank feels good when you own a business. It gives you flexibility, protects against surprises, and lets you sleep a little better at night.

But there’s another question worth asking: Is all of that cash really working for you?

The Benefits of Brokerage Accounts

We regularly see successful businesses carrying hundreds of thousands of dollars—and sometimes considerably more—in checking or low-yield bank accounts.

The reasoning usually makes perfect sense: We may need it, so we want to keep it liquid.

I agree. Business cash needs to be available. But available doesn’t necessarily mean sitting idle. For the portion of cash that isn’t needed tomorrow, there may be better options.

A brokerage account established in the name of the business can be linked to the company’s operating bank account, allowing excess cash to be moved into highly liquid, interest-producing investments while still maintaining ready access to the money.

When the business needs the cash, it can generally be moved back to the operating account within a few business days. The goal isn’t to take unnecessary risk with operating capital. Quite the opposite.

It’s to be more intentional about what the business is already doing with its money. Think about your own business for a minute. How much cash do you typically keep in the bank? How much do you actually need immediately? And what is the rest earning?

If a business consistently carries $250,000, $500,000 or $1 million of excess cash, even a modest improvement in yield can translate into meaningful additional income over the course of a year—without changing how the business operates.

That’s the part I think gets overlooked.

Business owners spend an enormous amount of time trying to improve margins, control expenses and increase profitability. Meanwhile, one of the easiest places to improve the financial efficiency of the business may be sitting right there on the balance sheet.

There’s a better way to manage excess business cash—and it doesn’t have to be complicated.

If you’re wondering whether your business is holding more cash than it needs, let’s take a look at it together. We can help determine what should remain immediately available, what could potentially be working harder, and how to structure it so you still have access when the business needs it.

Sometimes better financial planning isn’t about making a big change. It’s simply about making the money you already have work a little harder.

August 13, 2026August 13, 2026Business, Economy, Finance, InvestmentMaggie Tredwell

Selling Your Business? How You Receive the Money Matters.

By Brian Wheeler, Director of Wealth Management & Business Brokerage

If you’re preparing to sell a business that you’ve spent 20 or 30 years building, you’re probably spending a lot of time thinking about one number: the sale price.

That’s understandable. But I’ve found that there is another number that deserves almost as much attention.

The Number That Matters After the Sale Price

How much of the sale price will you actually keep?

Consider an owner who sells a business for several million dollars with very little remaining tax basis. Receiving all of those proceeds in one year could create a significant taxable gain. You may have negotiated a great price for your business, only to discover that how you receive the money has a significant impact on what ultimately stays in your pocket.

Spreading Payments May Spread the Tax Impact

That’s where a Structured Installment Sale can become interesting.

Instead of receiving the entire purchase price at closing, a seller may be able to take the cash they need today and structure the balance into payments over 10, 15 or 20 years. If properly designed under the installment-sale rules of IRC Section 453, the taxable gain associated with those future payments may also be recognized over time rather than entirely in the year of sale.

Think about that for a moment. If you don’t need all of the money today, does it make sense to potentially pay tax on all of the gain today?

You May Not Have to Finance the Buyer

There is another part of this strategy that I find equally compelling. A business owner might hear “installment sale” and immediately think, I don’t want to finance the buyer for the next 15 years. I wouldn’t blame them.

That’s not what we’re talking about.

With a properly structured arrangement, the buyer can fund the applicable purchase price at closing and move on with the business. The structured portion is then used to fund the seller’s future payment stream. The seller isn’t relying on the new owner to successfully operate the company for the next decade or two in order to make those payments.

For someone approaching retirement, that can be an interesting combination: liquidity today, predictable income tomorrow, potential tax benefits over time, and less exposure to the future financial condition of the buyer.

Of course, this isn’t the right answer for every business owner or every sale. There are specific tax and legal requirements, and your CPA and other advisors should be involved in determining whether the strategy makes sense.

There is also one very important catch.

Timing Is Critical

You need to have this conversation before the sale closes.

The buyer needs to participate in the arrangement, and the structure generally needs to be established before you take possession of the proceeds. If the money has already landed in your bank account, you’ve likely lost the opportunity to go back and restructure how you received it.

So, if a business sale may be somewhere in your future, I’d encourage you to think beyond simply asking, “What can I sell my business for?”

Questions to Ask Before You Close

Ask a few more questions.

How much cash do I really need at closing?
Could spreading some of the gain over time improve my tax picture?
And if I want income from my business sale for the next 10 or 20 years, do I really want to depend on the buyer to provide it?

Selling your business isn’t just about getting the highest price. It’s about what happens to that money after the business you’ve spent a lifetime building is no longer yours.

If you’re thinking about selling in the next few years—or already have a buyer at the table—let’s have the conversation before you close. There may be opportunities available today that won’t be available after the transaction is complete.

Structured installment sales involve legal, tax and financial considerations and may not be appropriate for every transaction. Installment-sale tax treatment is subject to applicable requirements under IRC Section 453. Business owners should consult with their tax and legal advisors before implementing any strategy.

August 6, 2026August 6, 2026Business, Economy, Finance, InvestmentMaggie Tredwell

Did You Build a Business… or Did You Buy Yourself a Job?

Did You Build a Business... or Did You Buy Yourself a Job?

By Brian Wheeler, Director of Wealth Management & Business Brokerage

Let me ask you a question that may be a little uncomfortable: If you disappeared from your business for the next ninety days, would your company keep growing… or would it simply wait for you to come back?

Most business owners don’t like that question because they already know the answer.

Leadership or Dependency? Know the Difference

The irony is that many owners wear their indispensability as a badge of honor. Every important decision runs through them. Their customers want to talk to them. Their employees rely on them. They solve the biggest problems, approve the biggest purchases, and hold the key relationships. It feels like leadership.

But what if it’s actually dependence?

I’ve met plenty of business owners who have built impressive companies with loyal employees, growing revenues, and years of hard work behind them. From the outside, they look successful. Yet underneath, many have unknowingly created something very different.

They haven’t built a business that works for them—they’ve built a business that can’t function without them.

That’s not freedom. That’s a very demanding job.

A Stronger Business Starts with Letting Go

The surprising part is that the path to a better business and a more valuable business is often the same. It starts by intentionally reducing the owner’s dependency. That doesn’t mean becoming less important. It means building a company that’s strong enough to succeed because of the team, the systems, and the culture you’ve created—not because you’re present every minute of every day.

Great employees become trusted leaders. Clear systems replace tribal knowledge. Customer relationships are diversified so the business isn’t dependent on one or two key accounts—or one owner’s personal relationships. Decision-making is shared with capable people who have earned that responsibility. Those changes don’t just make the owner’s life better; they make the company stronger.

And here’s where it gets interesting. Those are the exact qualities sophisticated buyers are looking for. The business becomes more profitable because it operates consistently. It becomes more resilient because it doesn’t rely on one individual. It becomes more attractive because a buyer can envision success continuing after the transition. And perhaps most importantly, it gives the owner something many entrepreneurs haven’t experienced in years—options.

Whether you plan to sell in two years, twenty years, or never, that’s a worthwhile goal.

From a wealth planning perspective, this matters even more than most owners realize. For many entrepreneurs, their business is their largest asset. The decisions you make today about leadership, systems, client diversification, and owner independence don’t just affect the future sale of your company—they influence your retirement, your tax planning, your estate plan, and ultimately the legacy you leave behind.

That’s why I don’t believe exit planning starts when you’re ready to exit. I believe it starts the day you decide to build a business that’s capable of thriving without you.

Final Thoughts

So let me leave you with one final question:

If someone offered to buy your business tomorrow, would they be buying a valuable company… or would they really just be hiring you?

If that question gives you pause, now is the perfect time to find out where you stand.

Keystone Business Brokers is currently offering complimentary business valuations.

Even if selling isn’t on your radar today, understanding what drives the value of your business can help you make better decisions today, create more freedom tomorrow, and put yourself in the strongest possible position whenever that next chapter begins.

July 30, 2026July 30, 2026Business, Finance, Investment, TaxesMaggie Tredwell

From “Just Sold” to Tax Strategy: How a Commercial Property Acquisition Can Create Immediate Cash-Flow Benefits

You know the old saying: “Debt forgiven is income earned.” The IRS agrees. But like most things in the tax world, the truth depends on why and how that debt disappeared.

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July 14, 2026July 14, 2026Business, Economy, Finance, InvestmentMaggie Tredwell

Experience Is a Wonderful Teacher

Experience Is a Wonderful Teacher.

By Brian Wheeler, Director of Wealth Management & Business Brokerage

The Problem Is That Life’s Biggest Financial Decisions Rarely Give Us the Opportunity to Practice First.

The Reality of Once-in-a-Lifetime Moments

A colleague and I were talking this week about a friend who’s preparing to become more involved in her mother’s business. Her mother is in her eighties, still active in the company, and like many successful business owners, has spent a lifetime building something that’s much more than a source of income. It’s part of her identity.

Naturally, the conversation has begun to shift toward the future. At some point they’ll need to decide how ownership should transition, what roles each of them wants to play, and what the next chapter of the business should look like.

As we talked, one thought kept coming back to me: why would anyone expect themselves to know all of their options the first time they face one of life’s biggest financial decisions?

They’ve probably never been here before.

The more I thought about it, the more I realized this isn’t really a story about business succession. It’s a story about life. Most of us only retire once. We sell one business. We become an executor for the first time. We help aging parents navigate difficult financial decisions. We settle an estate. We transition a family business. These aren’t decisions we make every year. They’re once-in-a-lifetime moments.

Yet we often expect ourselves to know exactly what to do. Over the years, I’ve come to appreciate something that’s both simple and easy to overlook.

Experience is a wonderful teacher. The problem is that life’s biggest financial decisions rarely give us the opportunity to practice first.

Discovering the Questions We Need to Ask

That’s why I find it interesting when people hesitate to ask for another perspective because they think they should already know the answers. In reality, the greatest value often isn’t someone giving you the answer. It’s someone helping you discover questions you didn’t know needed to be asked. I’ve found that clarity doesn’t usually come from having all the answers. It comes from asking better questions before important decisions become permanent.

I’ve watched business owners learn there were succession strategies they never knew existed. I’ve seen families discover tax opportunities after decisions had already been made. I’ve watched people realize there were more flexible ways to transfer wealth, protect a business, or care for the next generation than they ever imagined.

None of those people made mistakes because they weren’t intelligent. They simply hadn’t been there before. The longer I’ve been doing this, the less surprised I am by what people don’t know. I’m much more surprised by how often they assume they’ve already seen all of their options.

The True Value of Experienced Advice

That’s one of the reasons I believe experienced advice has value. Not because someone else should make your decisions, but because they’ve helped many other families through similar moments. Experience doesn’t replace your goals or your values. It simply helps you make important decisions with a broader understanding of the possibilities in front of you.

Here’s something I’d encourage you to think about this week: is there an important financial decision on your horizon that you’ve never faced before?

Maybe it’s retirement. Maybe it’s selling a business. Maybe it’s helping aging parents.

Maybe it’s updating your estate plan or preparing the next generation to carry on something you’ve spent a lifetime building.

If this is the first time you’ve faced that decision, don’t let it also be the first time you’ve explored all of your options.

Ask questions. Seek perspective. Have conversations with people who’ve walked this road many times before.

One of the most rewarding moments in my profession is watching someone realize they have more options than they thought they did.

Sometimes that realization changes everything. And sometimes, it begins with a conversation they almost never had.

June 30, 2026June 30, 2026Business, Finance, InvestmentMaggie Tredwell

Strike While the Iron Is Hot

As we move into the final stretch of the year, it’s time for every business owner to take a closer look at their policies and documentation for company-provided vehicles and employee reimbursements.

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