Exit Strategy Archives - Keystone CPAs

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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June 3, 2026June 3, 2026Business, Finance, InvestmentMaggie Tredwell

The Importance of Proper Financial Planning Before Selling Your Business

The Importance

of Proper Financial Planning Before Selling Your Business

Planning to sell your business is a significant decision that requires meticulous preparation, particularly in the financial realm. Proper financial planning is vital to ensure a smooth and successful transition and to maximize the value of your business. Keystone CPAs, with their deep understanding of the critical role that financial planning plays in selling a business, are here to offer essential tips that will guide you through this important phase, instilling confidence in your financial planning.

Understanding the Value of Your Business: As a business owner, your role is crucial in preparing to sell your business. One of the initial steps is obtaining a comprehensive understanding of its value. Keystone CPAs advise engaging in a thorough business valuation to accurately assess the worth of your company. This assessment, in which you play a crucial part, will serve as a foundation for setting a realistic selling price and understanding potential areas for improvement to enhance the value of your business. Financial Documentation and Reporting: Organized and accurate financial documentation is essential when selling your business. Keystone CPAs emphasize the importance of maintaining detailed financial records and reports to provide prospective buyers with a clear and transparent insight into your company’s economic health and performance. This includes financial statements, tax records, profit and loss statements, and other pertinent financial documents.

Tax Planning and Optimization: Proper tax planning is crucial when selling a business. Keystone CPAs advise business owners to engage in tax optimization strategies to minimize tax liabilities and maximize the after-tax proceeds from the sale. Understanding the tax implications of the sale and implementing tax-efficient strategies can significantly impact the financial outcome of the transaction.

Financial Forecasting and Projections: Prior to selling your business, creating detailed financial forecasts and projections can be invaluable in demonstrating the future potential and profitability of your company to potential buyers. Keystone CPAs recommends preparing realistic and data-driven financial projections that align with the growth trajectory of your business, providing a compelling case for its future success. This forward-looking approach can instill a sense of hope and optimism in the business owner.

Exit Strategy and Succession Planning: Crafting a well-defined exit strategy and succession plan is fundamental to proper financial planning before selling your business. Keystone CPAs stress the importance of outlining a clear path for the transition of ownership and leadership, ensuring a seamless transfer of control and responsibilities.

In conclusion, selling a business demands meticulous financial planning and strategic decision-making. Keystone CPAs understand the complexities involved in this endeavor and offer invaluable guidance to business owners embarking on this important journey. By leveraging their expertise and following these essential tips, business owners can navigate the financial aspects of the sale with confidence, ultimately achieving a successful outcome.

Keystone CPAs stand ready to assist business owners in achieving their financial objectives. Contact us today to learn more about preparing your business for a successful sale.