Blog Classic - Keystone CPAs

October 8, 2026October 8, 2026Business, Economy, Finance, InvestmentMaggie Tredwell

The Best Time to Sell Your Business May Be When You Least Want To

By Brian Wheeler, Director of Wealth Management & Business Brokerage

What if the best time to sell your business comes at exactly the moment you have the least interest in selling it? That’s one of the more difficult conversations I have with business owners. When the business is growing, profits are strong and everything seems to be working, selling can feel almost ridiculous. Why walk away now? Why not enjoy another few years of growth?

When the Timing Changes

The problem is that buyers may be looking at those same results and thinking something very different:

“This is exactly the kind of business we want to buy.”

And sometimes that window doesn’t stay open as long as we think. I’ve watched this happen firsthand.

We worked with an owner who considered selling while the business was performing very well. Ultimately, the decision was made to keep going. And at the time, that decision made perfect sense. Business was good.

About a year and a half later, the owner was ready to revisit the sale. Only now, things had changed. Results were beginning to decline. Some of the momentum was gone. The owner was more ready to sell—but unfortunately, the business wasn’t quite as attractive as it had been 18 months earlier.

It was still a good business. But the conversation around value had changed.

That’s the irony of timing a business sale: when everything is going well, selling can feel unnecessary. When things aren’t going as well, selling can suddenly feel very necessary.

And buyers know the difference.

What Buyers See in Your Business

This is also why understanding what actually drives the value of your business matters long before you’re ready to sell.

Revenue and profitability certainly matter, but buyers look much deeper. They want to understand the quality and transferability of the business they’re buying.

There are eight key drivers of business value that we spend time discussing with owners—things like financial performance, growth potential, recurring revenue, customer concentration, management strength, competitive differentiation, systems and processes, and how dependent the business remains on the owner.

An owner may look at the company and see 20 or 30 years of hard work, relationships and sacrifice. A buyer looks at the same company and asks:

“What happens to this business after you leave?”

That’s a very different perspective.

The good news is that many of the things that influence value can be improved. The problem is that they usually can’t be fixed six months before you want to sell.

Preparing Before You're Ready

Which brings me to another point I make with owners: selling a business probably shouldn’t begin with waking up one morning and deciding, “Today’s the day.”

There are too many other pieces that need to line up.

What does life after the business look like? How much income will you need? What does the business need to sell for to support that lifestyle? What are the tax implications? How does the sale fit with your estate plan? And what do you actually want to do when Monday morning no longer means going to the business?

As a wealth advisor and CEPA®, that’s where much of my work with business owners begins. Before we’re talking about a transaction, we’re trying to connect the value of the business with the owner’s personal financial plan and the life they want to have afterward.

Sometimes that planning tells us they’re closer than they thought. Sometimes it tells us there is work to do. Either answer is valuable—especially when you still have time to do something about it.

The Advantage of Having Choices

I think one of the best positions a business owner can create is having a valuable, transferable business, a personal financial plan that works, and no immediate need to sell.

That’s when you have choices.

You can continue growing. You can watch the market. You can consider an unexpected offer. Or, when the business is performing exceptionally well and buyers are willing to recognize that value, you can decide that maybe this actually is the right time.

After spending decades building a business, the final chapter deserves more thought than simply deciding you’re ready to be done.

Top value usually comes from thoughtful preparation, a business built to transfer, and the ability to recognize exceptional timing when you have it.

October 8, 2026October 8, 2026Business, Finance, Investment, TaxesMaggie Tredwell

The IRS Is Getting Smarter: Is Your Tax Return Ready for a Data-Driven Audit?

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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October 1, 2026October 1, 2026Business, Economy, Finance, InvestmentMaggie Tredwell

What Changes When Your Paycheck Stops? Why adding certainty may be just as important as pursuing investment returns.

By Brian Wheeler, Director of Wealth Management & Business Brokerage

Let’s talk about something I don’t think gets nearly enough attention when people are preparing for retirement.

When Your Investments Become Your Paycheck

For most of our working lives, we have something we probably take for granted—a paycheck. Every couple of weeks, money shows up. We pay the bills, enjoy life, save for retirement and invest what we can.

Then one day the paycheck stops, and the money we spent 30 or 40 years accumulating suddenly has a different job. Now it must become the paycheck.

Think about what that means. While you’re working, a 20% market decline certainly doesn’t feel good, but you still have income coming in. Now imagine that same decline six months after you retire, when you may need to sell those investments to pay the bills.

Those dollars are gone. They aren’t there to participate when the market eventually recovers.

The Risk of Retiring Into a Down Market

This is called sequence-of-returns risk, and retirement-income researcher Wade Pfau has spent years studying it. But the interesting part isn’t simply understanding the risk. It’s what we might be able to do about it.

What if reducing retirement risk doesn’t mean making your entire portfolio more conservative?

What if instead we identify the income you absolutely need and create more certainty around that part of your life?

Creating More Certainty Around Retirement Income

Social Security may provide some of it. Cash and high-quality fixed income might provide another layer. For the right person, guaranteed lifetime income from an annuity may play a role. Properly structured cash-value life insurance can potentially provide another source of money with different market and tax characteristics.

The objective isn’t necessarily to replace your investment portfolio. It may be to take some of the pressure off it.

If your lifestyle isn’t entirely dependent on selling stocks every month, what happens when the market falls 20%?

Maybe you don’t have to sell. And you’ve just given the long-term portion of your portfolio something incredibly valuable: time to recover.

That’s the part I think many people miss. Adding certainty to one part of your financial life may actually allow you to be more comfortable taking appropriate investment risk with another.

Why This Matters for Business Owners

For business owners, this can be especially important. You may have spent decades with your income, net worth and financial security tied largely to one company. Then you sell the business and suddenly have several million dollars to invest.

You’ve diversified the asset. But have you actually created financial security?

Maybe some of that money needs to provide income next year. Some needs to grow for another 20 years. Some is there for emergencies, and some may ultimately be intended for your children or grandchildren.

If every dollar doesn’t have the same job, why should every dollar take the same risk?

Planning Beyond Accumulation

If you’re within five or ten years of retirement—or getting closer to selling a business—I wouldn’t only ask whether you’ve accumulated enough.

I’d ask:

How much of your future do you want dependent on what the markets happen to do next?

There isn’t one right answer, and these strategies aren’t appropriate for everyone. But there are ways to create more certainty, address longevity risk, improve tax diversification and reduce the need to sell investments at exactly the wrong time.

Those are conversations worth having before the paycheck stops. Because retirement planning isn’t simply about how much you’ve accumulated.

It’s about turning what you’ve accumulated into a life you can confidently live.

October 1, 2026October 1, 2026Business, Finance, Investment, TaxesMaggie Tredwell

Why Does the Partnership Pay the Tax? The History Behind the BBA Audit Regime

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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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.

September 24, 2026September 24, 2026Business, Finance, Investment, TaxesMaggie Tredwell

When a Positive Adjustment Does Not Mean More Tax: The BBA Balance-Sheet Problem

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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September 17, 2026September 17, 2026Business, Economy, Finance, InvestmentMaggie Tredwell

BUSINESS OWNERS: ARE YOU READY?

By Brian Wheeler, Director of Wealth Management & Business Brokerage

If someone offered to buy your business tomorrow, would you know whether the offer was actually a good one? Not whether the number sounded good, but what your business is really worth, what you would actually keep after taxes, debt and transaction costs, and maybe most importantly, whether that amount would be enough to fund the life you want after the business.

Your Business Value Is More Than a Number

Recent research from Value Builder found that 21% of business owners received a written offer for their company during the past year, but only 1% were considered ready to sell. At the same time, 58% expect to exit within five years. That’s quite a gap.

Most owners naturally start with, “What is my business worth?” I think there’s another question that matters just as much: What do I need it to be worth?

Those two numbers aren’t always the same. For many business owners, the company is their largest asset, and eventually that business value needs to translate into personal financial independence.

The good news is you don’t have to be planning to sell anytime soon to start working on value:

Can the company operate without you?
Are the finances clean?
Do you have strong people?
Is revenue overly concentrated?
Have you thought about taxes before a transaction occurs?

These are things that can make your business stronger today while giving you more choices tomorrow. At Keystone, we believe business planning and personal financial planning belong in the same conversation. The business, the taxes, the eventual exit and your personal financial future are all connected.

You don’t necessarily need to be ready to sell. You should be ready to choose. So, if someone called tomorrow and asked what it would take to buy your business, would you be ready to answer?

September 17, 2026September 17, 2026Business, Finance, Investment, TaxesMaggie Tredwell

The First Number Is Not Always the Final Number: Understanding BBA Partnership Audit Modifications

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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September 10, 2026September 10, 2026Business, Economy, Finance, InvestmentMaggie Tredwell

Does Bitcoin Belong in Your Portfolio?

By Brian Wheeler, Director of Wealth Management & Business Brokerage

Bitcoin has a way of getting people’s attention. When the price is going up, people wonder if they’re missing out. When it drops, the question quickly becomes whether it was ever a good investment in the first place. Maybe there’s a better way to look at it.

Instead of trying to predict where Bitcoin is headed next, I think the more useful question is: does Bitcoin deserve a small place in a well-diversified portfolio?

There are good arguments on both sides.

The Case for a Small Allocation

One of the most interesting things about Bitcoin is that the supply is limited. There will never be more than 21 million Bitcoin. At the same time, it’s becoming much easier for everyday investors, investment firms and large institutions to own it.

Limited supply and growing demand can be a powerful combination.

The Risks to Keep in Mind

But let’s not ignore the other side.

Bitcoin doesn’t produce earnings or pay a dividend. We can’t look at its profits and calculate what we think it’s worth like we can with a business. And we’ve already seen how quickly the price can rise—or fall.

That’s why I don’t think this needs to be an “all in or all out” decision.

Why Position Size Matters

Think about a 3% allocation.

If you put 3% of a portfolio into Bitcoin and Bitcoin fell 80%, the impact on the overall portfolio would be about 2.4%, assuming everything else stayed the same.

Nobody wants to lose 80% on an investment. But losing 80% on 3% of your portfolio is very different from losing 80% on 30% of it.

Now look at the other side.

If Bitcoin continues to gain acceptance over the next 10 or 20 years and increases significantly in value, even a small investment could have a meaningful impact on your portfolio.

You don’t have to make a huge bet to participate in a potential opportunity.

A Broader Way to Think About Investing

And really, this isn’t just about Bitcoin. It’s about how we think about investing.

We don’t have to know exactly what will happen next. We need to understand the opportunity, understand the risk, and decide how much of that risk makes sense for you.

For some people, the right amount of Bitcoin may be zero. For others, maybe it’s 1%, 3% or 5%.

There isn’t one answer that works for everyone.

Your investments should fit your financial plan, your goals and the amount of risk you’re comfortable taking—not what’s getting the most attention in the news.

Bitcoin’s future is uncertain. But that doesn’t mean we should ignore it.

It means we should understand it.

Ready to Talk It Through?

Wondering whether Bitcoin—or another alternative investment—belongs in your portfolio? Let’s have a conversation.

We can help you look at the opportunity, understand the risk and decide whether it makes sense as part of your overall financial plan.

September 10, 2026September 10, 2026Business, Finance, Investment, TaxesMaggie Tredwell

Is AI Hallucinating, or Did the Human Make It Hallucinate?

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.

Continue Read

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