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.
Take Care of the People That Take Care of You!
Take Care of the People That Take Care of You!
By Brian Wheeler, Principal, Keystone Wealth Advisors
One thing I have noticed over the years is that the true “value” of a company comes down to a handful of key people.
The True Value of a Company
The individuals who keep operations running smoothly, maintain important client relationships, are the keepers of the Company’s “Institutional Knowledge” and help the business grow year after year.
The operations leader keeps everything running smoothly.
The salesperson who maintains important client relationships.
The manager who keeps the team moving in the right direction.
The Impact of Losing Key People
Over the years, I have seen situations where the departure of just one of these individuals created a ripple effect that impacted growth, operations, and sometimes even the perceived value of the business.
One of the questions I sometimes ask business owners is simple, “If one of your key people decided to leave tomorrow, how difficult would it be to replace them?”
The answer often opens the door to some very good planning conversations.
Incentivizing and Retaining Key Employees
Many of the business owners we work with choose to create additional incentives for the key people who help build the business.
These might include things like:
- Deferred compensation plans
- Phantom equity or stock appreciation arrangements
- Executive bonus strategies
- Supplemental retirement benefits
A Strategic Approach: Non-Qualified Deferred Compensation
One approach that can work particularly well is non-qualified deferred compensation.
These arrangements allow business owners to reward loyalty and long-term contribution while aligning key employees with the future success of the company—often without giving up ownership in the business.
Why Leadership Stability Matters to Buyers
Interestingly, when we work with business owners who are preparing for an eventual transition or sale of their company, one of the most important factors buyers often look at is the strength and stability of the leadership team that will remain after the owner steps away.
Protecting the Value You’ve Built
Taking care of the people who help build your business is not just good leadership.
In many cases, it is also one of the smartest ways to protect the value you have worked so hard to create.
If you would like to explore some of the strategies available for aligning and rewarding key people in your organization, I would be happy to share a few ideas.
R&D Tax Credits: A Tax Opportunity Many Owners Miss
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.
Accountable Plans: A Smart Way to Reimburse Business Expenses Tax-Free
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.
The $200,000 Retirement Contribution Most Business Owners Don’t Know Exists
The $200,000 Retirement Contribution Most Business Owners Don’t Know Exists
By Brian Wheeler, Principal, Keystone Wealth Advisors
Many business owners assume their retirement plan is already doing everything it can.
After all, they’re contributing to their 401(k), their employees have a plan available, and their payroll provider handles the administration. Everything seems to be working.
But Here's the Surprising Reality:
Many successful business owners are leaving six-figure tax deductions on the table every year.
Not because they’re doing anything wrong — but because their retirement plan was designed for simplicity, not optimization.
The Hidden Opportunity
Most retirement plans set up through payroll providers are prototype 401(k) plans. These plans are convenient and easy to administer, but they are typically designed to serve the broadest possible group of employers.
That means they often don’t take full advantage of the flexibility available under the tax code.
For business owners with strong income and stable cash flow, there may be an opportunity to significantly increase retirement contributions through a more customized plan design.
When a Retirement Plan Becomes a Strategic Tool
In the right situation, combining a 401(k) plan with a Defined Benefit plan can dramatically increase the amount a business owner is able to contribute each year.
Depending on factors such as age, income, and employee demographics, total contributions can sometimes reach: $150,000 – $300,000+ annually.
These contributions are typically:
- Tax deductible to the business
- Compounding tax-deferred for retirement
- Building wealth outside the business
For owners in their peak earning years, this strategy can become one of the most powerful ways to reduce taxes while accelerating retirement savings.
Why Plan Design Matters
Retirement plans are not one-size-fits-all.
The amount a business owner can contribute depends heavily on how the plan is structured. Key factors include:
- Owner age and income
- Number and age of employees
- Compensation structure
- Business profitability
- Long-term retirement goals
A properly designed plan can allow owners to maximize their own contributions while still providing meaningful benefits to employees and remaining fully compliant.
The Limits of “Off-the-Shelf” Plans
Payroll providers often offer retirement plans as a convenient add-on to payroll services.
While these plans are easy to implement, they are typically built using standardized designs that may not incorporate strategies such as:
- Age-weighted allocations
- Cross-tested profit sharing
- Cash balance or defined benefit integrations
- Advanced plan design techniques
For high-income business owners, these limitations can translate into missed opportunities for significant tax savings.
Beyond the Business
For many entrepreneurs, the business itself becomes their largest asset.
But relying on the eventual sale of the business alone can create risk.
A well-structured retirement plan allows owners to systematically move wealth out of the business and into personal assets while benefiting from meaningful tax deductions along the way.
A Question Worth Asking
If your business is having a strong year, it may be worth asking:
Is my retirement plan designed for convenience… or designed to maximize opportunity?
The difference can be substantial.
Better Together
At Keystone, our teams work together across tax, wealth advisory, and business consulting to help business owners design retirement strategies that align with both their business success and their long-term financial goals.
If you’d like to explore whether your retirement plan could be working harder for you, we would be happy to start that conversation.
March 16 Is More Than a Tax Deadline — Rethink Your PTET Election in 2026
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.
How Do Markets React to Global Conflicts?
How Do Markets React to Global Conflicts?
By Brian Wheeler, Principal, Keystone Wealth Advisors
What History Shows May Surprise You.
When global tensions rise, many investors begin asking the same question:
“What does this mean for the markets?”
A Concerning Ripple Effect
For many business owners and investors, these moments can create uncertainty not only about their portfolios, but also about the broader economy and the businesses they’ve worked hard to build.
News coverage can make the situation feel urgent and unpredictable. Headlines focus on uncertainty, potential economic disruption, and the ripple effects across global trade and energy markets.
It’s natural to wonder whether events like these should change how you think about your investments.
The Initial Market Reaction: Uncertainty
When a major geopolitical event occurs, markets typically respond with short-term volatility.
Investors dislike uncertainty, and global conflicts create plenty of it. Questions arise about economic stability, supply chains, energy prices, and how governments and central banks might respond.
Because of this, markets often experience an initial pullback or spike in volatility as investors digest new information.
But that initial reaction is usually only the first chapter of the story.
What History Shows
Over the past century, markets have navigated numerous wars and geopolitical crises. While each event has its own circumstances, a consistent pattern tends to emerge:
- Markets often react quickly at the onset of conflict.
- As more information becomes available, markets begin to stabilize.
- Long-term performance is ultimately driven by economic growth, innovation, and corporate earnings, not the conflict itself.
In many cases, markets begin recovering well before conflicts are resolved, as investors shift their focus back to long-term fundamentals.
A Look at History
While past performance never guarantees future results, history can provide helpful perspective:
Conflict / Event — Market Reaction — Longer-Term Outcome.
- World War II (1941) — Markets initially fell after Pearl Harbor — U.S. markets recovered within months and rose significantly during the war years
- Korean War (1950) — Short-term decline as uncertainty increased — Markets stabilized and resumed long-term growth
- Vietnam War (1960s–1970s) — Volatility and inflation concerns — Long-term growth continued through economic expansion
- Gulf War (1990–1991) — Markets declined leading up to the invasion — Rapid recovery once military action began
- September 11, 2001 — Sharp but brief decline after markets reopened — Markets recovered within months
- Russia–Ukraine Conflict (2022) — Initial volatility across global markets — Markets stabilized as investors refocused on fundamentals
While the events themselves were significant and often tragic, the broader lesson is that financial markets have historically been resilient over time.
Why Long‑Term Investors Stay Disciplined
Major geopolitical events can feel unprecedented in the moment, but history reminds us that markets have navigated:
- wars
- recessions
- political shifts
- inflation cycles
- global crises
And yet over time, markets have continued to grow alongside the global economy.
This doesn’t mean volatility disappears. It simply means that long‑term investment success is usually driven by discipline, diversification, and patience — not by reacting to headlines.
The Value of Perspective
Periods of global tension remind us that investing is not just about numbers and charts. It’s also about maintaining perspective during uncertain times.
A well‑constructed financial plan is designed to account for volatility, uncertainty, and the unexpected events that inevitably occur over time.
While the world can feel unpredictable in the short run, long‑term investors who remain focused on their goals often find that staying the course is the most productive strategy.
For business owners in particular, moments like these often highlight the importance of coordinating investment strategy, tax planning, and long‑term business goals within a single, thoughtful financial plan.
Why Guidance Matters During Uncertain Times
Moments of global uncertainty often remind investors why having a thoughtful plan — and someone to help interpret the noise — can be so valuable.
Markets will always experience periods of volatility, whether driven by economic cycles, political developments, or global events. What matters most is having a strategy designed around long‑term goals, diversification, and risk tolerance, rather than reacting to each new headline.
During times like these, one of the most valuable roles an advisor can play is helping clients separate signal from noise, remain focused on their long‑term objectives, and make thoughtful decisions that align with their broader financial plan.
If you have questions about how current events may impact your financial plan or investment strategy, we are always happy to talk.
Sometimes the most valuable thing an advisor can provide during uncertain times is clarity and perspective.
Buying or Selling a Franchise: Lessons from the Owner’s Seat
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.
Buyer Beware: How Deferred Maintenance Destroys Enterprise Value
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.
Before You Buy the Golf Course: Protecting the Wealth You’ve Spent a Lifetime Building
Before You Buy the Golf Course: Protecting the Wealth You’ve Spent a Lifetime Building
By Brian Wheeler, Principal, Keystone Wealth Advisors
There is something deeply appealing about owning a “lifestyle” business. You love golf, so buy a golf course! Be the central gathering point for friends and family at your newly purchased restaurant, having private tastings at your winery.
The list goes on and on.
The Allure of the Lifestyle Business
For many successful business owners and professionals, these opportunities feel like the natural next chapter — a blend of passion, prestige, and investment.
But as wealth advisors, we have to ask a harder question: Are you investing… or are you risking the “farm”?
Charlie Lieder, former PGA professional and one-time owner of Arrowcreek Country Club once said, “our members are generally captains of industry, and are very successful. But they don’t know what it takes to run a golf course!”
Golf courses, restaurants, hotels, wineries — these are not just financial assets. They are emotional assets. And emotional assets are often priced differently in the mind than they are in the market.
When Passion Meets Concentration Risk
The danger is not the dream.
The danger is over-concentration.
If 60–80% of your net worth is tied up in one operating business, and you leverage additional capital to buy a capital-intensive lifestyle asset, you may unknowingly expose everything you have worked decades to build.
The Hidden Cost of Lifestyle Businesses
These Businesses Are Capital Hungry. Unlike asset-light advisory firms or professional practices, lifestyle businesses are infrastructure-heavy.
Golf Courses
- Irrigation systems
- Equipment fleets
- Clubhouse maintenance
- Seasonal labor swings
- Weather dependency
Restaurants
- High failure rates
- Labor volatility
- Food cost compression
- Lease exposure
- Thin operating margins
Hotels
- Cyclical occupancy
- Renovation cycles every 5–7 years
- Brand standard capital requirements
- Heavy fixed debt structures
These are not passive investments. They require consistent reinvestment just to maintain cash flow — let alone grow it.
I’ve seen successful entrepreneurs leverage real estate, brokerage accounts, and even retirement assets to support a struggling lifestyle acquisition.
That is when passion turns into panic.
Wealth Planning Before the Purchase
Before signing a letter of intent, I encourage clients to walk through five critical questions:
1. What Percentage of My Net Worth Is at Risk?
- If this investment fails entirely, what does my life look like financially? Do I have enough time left in this life to recover financially?
2. Is This Funded With Excess Capital — or Core Capital?
- Excess capital is investable surplus.
- Core capital is retirement security.
- Never confuse the two.
3. What Is the Downside Scenario?
Model:
- 20% revenue decline
- Two years of flat cash flow
- Major capital expenditure
- Higher interest rates
If the model breaks your personal balance sheet, the deal is too large.
4. How Correlated Is This to My Other Income?
- If you own a business sensitive to economic cycles, adding another cyclical asset compounds risk.
5. Is There a Defined Exit Strategy?
- Lifestyle businesses are often harder to sell than they are to buy.
Debt Magnifies Emotion
Lifestyle acquisitions are often financed with significant leverage.
Debt:
- Amplifies returns in good years
- Accelerates losses in bad years
- Removes flexibility
- Forces decisions under pressure
When personal guarantees are involved, the line between business risk and personal risk disappears.
The Psychological Trap
Many high achievers believe:
“I built one successful business. I can fix this one too”, and sometimes that’s true. But lifestyle businesses often operate on lower margins, require different skill sets, and face customer expectations that are far less forgiving.
A Smarter Approach
Owning a lifestyle business can absolutely be rewarding — financially and personally.
The key is structure and scale.
- Keep it to a manageable percentage of total net worth.
- Avoid cross-collateralizing core family assets.
- Maintain personal liquidity reserves.
- Stress test the numbers with conservative assumptions.
- Separate identity from investment.
You can pursue passion — without jeopardizing protection. Protect what you’ve built — so you can enjoy what you buy.
Michael D. Bosma, CPA Brian Wheeler
Keystone CPAs Keystone Wealth Advisors
Better Together.