Healthcare Costs Threatening Your Retirement?
Healthcare expenses are a critical and often unpredictable component of any financial plan. As a successful professional, you can't afford to let surprise medical bills compromise your long-term goals for asset growth and legacy preservation. Our strategic framework outlines eight actionable steps to help you move from reactive expense management to proactive financial control. We'll show you how to leverage tax-advantaged accounts, optimize your insurance coverage, and integrate long-term care planning to safeguard your wealth against the rising cost of health.
Plan Now to Protect Your Wealth (And Sanity)
Read Andrew’s Story
For successful professionals and thriving business owners, achieving financial freedom is a journey mapped with investments, tax optimization, and legacy planning. You're not in retirement yet, but you're wisely looking ahead. However, a less-talked-about, yet potentially devastating, financial drain often lurks in the shadows, with the power to unravel even the best-laid plans: how healthcare costs impact retirement. These expenses, vital for ensuring the longevity to enjoy your carefully crafted financial plan, can be both unpredictable and substantial, presenting a unique challenge to your long-term financial goals and overall peace of mind.
You've dedicated years to building your wealth with diligence and foresight. Our objective now is to ensure that medical expenses, whether anticipated or a sudden surprise, never compromise your ability to grow assets or secure your family's future when you do reach retirement. With proactive planning for healthcare costs in retirement, these potential drains can be effectively managed, becoming a predictable component of your comprehensive financial picture rather than an unexpected and sanity-gutting threat to your future.
As a financial advisor specializing in integrating healthcare cost planning into broader financial strategies for clients like you, who are actively planning for retirement, I've compiled eight practical approaches. This guide will help you confidently manage these potential expenses now, keeping your financial progress steady and your future wealth secure.
Key Takeaways From This Article:
● Understand your current medical spending
● Plan ahead for expenses when possible
● Make sure your health plan works for you
● Take full advantage of your health benefits
● Comparison shop for medical services
● Maximize HSAs and FSAs
● Consider medical expense tax deductions
● Explore long-term care insurance
Understanding Your Current Medical Spending: A Baseline for Future Planning
Effective management of future healthcare needs begins with clear data. Take stock of your current healthcare expenditures to identify where your money is going. Reviewing past bills, bank statements, or patient portals can provide a comprehensive overview of your medical spending habits. This baseline is critical when you're planning for healthcare costs in retirement. Some key data to collect are items such as:
● Monthly health insurance premiums
● Copays and Coinsurance
● Prescription costs
● Vision and dental expenses
● OTC drugs and medical devices
Proactive Planning for Anticipated Medical Expenses: Don't Get Caught Off Guard
While medical emergencies are unforeseen, many healthcare costs can be planned for well in advance. Treating these expenses as a predictable part of your financial landscape allows for strategic preparation, safeguarding your retirement savings from medical costs. Some to consider are:
● Ongoing treatments for chronic conditions
● Maternity expenses or costs related to family expansion
● Elective procedures
● Genetic/hereditary conditions that will need to be addressed
Considering your family's health needs with a long-term perspective can help determine appropriate coverage and potential savings. Establishing a dedicated fund; such as an HSA, FSA, or even a cash reserve can ensure you're prepared without impacting your long-term strategy or incurring debt as you save for healthcare in retirement.
Optimize Your Health Plan: Is Your Coverage Aligned with Your Future Needs?
It's a common misconception that more extensive health coverage automatically equates to the best value, especially when planning for healthcare costs in retirement. Periodically assessing your health plan is crucial to ensure it aligns with your actual usage and your long-term financial objectives. Are you paying for benefits you rarely utilize, or are out-of-pocket costs becoming a burden?
● Low-Deductible Health Plans (LDHPs): These plans typically feature higher monthly premiums but lower out-of-pocket costs for medical services. They may be suitable for individuals with chronic health conditions or regular medical needs, providing immediate financial predictability.
● High-Deductible Health Plans (HDHPs): Characterized by lower monthly premiums and higher deductibles, these plans often offer eligibility for a Health Savings Account (HSA), which offers significant tax advantages for saving for future medical expenses. HDHPs can be an effective choice for healthy individuals with fewer anticipated medical expenses, particularly those focused on building substantial HSA for retirement planning.
Andrew's Insight: For many of my clients, an HDHP combined with an HSA proves to be a fiscally sound strategy. The blend of lower premiums and a tax-advantaged savings vehicle for future medical costs offers both immediate and long-term benefits, helping you fortify your retirement planning against medical costs.
Maximize Available Health Benefits: Don't Overlook Valuable Resources for Future Wellness
Your health plan often includes more than just coverage for illness or injury. Utilizing preventive care and wellness programs now can lead to both health improvements and financial savings by addressing issues before they become more complex or expensive, thereby reducing medical expenses in retirement.
● Annual physicals and routine screenings: These are an investment in your long-term health, helping to prevent more significant health issues down the road.
● Mental health services, fitness discounts, and wellness initiatives: Many plans offer these, contributing to overall well-being and potentially reducing your future healthcare needs.
Andrew's Insight: If a claim is denied, investigate. Errors occur, and a simple inquiry can often resolve coverage issues, saving you from unnecessary expenses. It’s a small effort now that can yield tangible financial returns later, protecting your retirement savings from medical costs.
Comparison Shop for Medical Services and Prescriptions: Smart Spending for Today and Tomorrow
When you can plan ahead for medical expenses, use the time to shop around for better pricing. Collaborate with your healthcare provider and insurer to obtain accurate cost estimates. Compare costs for prescriptions, procedures, and medical appointments (without sacrificing quality, of course). Generic medications, for instance, are often a cost-effective alternative to brand-name drugs, helping you stretch your healthcare budget as you plan for healthcare costs in retirement.
Leverage HSAs and FSAs: Powerful Tools for Saving for Healthcare in Retirement
If eligible through an HDHP, a Health Savings Account (HSA) is an invaluable tool for saving for healthcare in retirement. Similarly, Flexible Spending Accounts (FSAs), if offered by your employer, can provide significant tax advantages for common medical expenses such as copays, dental work, prescriptions, and vision care. These accounts are crucial for optimally planning for medical expenses in retirement.
Be aware, however, that there is a variation in utility between HSAs and FSAs, especially regarding their long-term potential for retirement planning:
● HSAs: These accounts offer a triple tax advantage: pre-tax contributions, tax-free growth, and tax-free withdrawals for qualified medical expenses. This translates into substantial tax efficiency for your healthcare spending. These accounts can accumulate value year after year and are portable, meaning they are not tied to a specific employer, making them ideal for long-term medical expenses retirement savings.
● FSAs: Funded with pre-tax dollars, these accounts typically operate on a "use it or lose it" basis within the plan year, though some employers offer limited grace periods. This account is employer-sponsored, meaning if you are to leave your employer, any funds in the account are forfeited. While useful for current expenses, they lack the long-term retirement savings benefits of an HSA.
Andrew's Insight: Beyond immediate expenses, an HSA can serve as a potent long-term savings vehicle. Funds roll over annually and can be invested, growing tax-free. Consider covering future medical needs in retirement with an account that has compounded tax-free for decades. This is a powerful component of comprehensive financial planning for healthcare and a key strategy to mitigate how healthcare costs impact retirement.
Consider the Medical Expense Tax Deduction for Significant Costs: A Potential Relief Valve
For years with unusually high medical expenditures, you may be eligible for a tax deduction. If your qualified unreimbursed medical expenses exceed 7.5% of your Adjusted Gross Income (AGI) and you itemize deductions, this can provide notable tax relief, helping to alleviate the burden of significant medical expenses on your retirement savings.
Eligible expenses can include:
● Fees for doctors, specialists, and mental health professionals
● Inpatient hospital care
● Prescription medications
The IRS has a complete list of medical expenses which are eligible for deducting.
Long-Term Care Insurance: Safeguarding Your Legacy
While Medicare provides crucial support once you reach retirement, its coverage for long-term care needs, such as in-home care, assisted living, or nursing facilities, is limited. Long-term care insurance fills this critical gap, helping to protect your accumulated assets and ensuring that future care costs do not erode your legacy plans or retirement savings.
Exploring this option earlier can lead to more favorable premiums. For example, acquiring a policy in your 40s when in good health typically results in lower costs than waiting until later in life when health issues may arise. This proactive step is a key part of planning for healthcare costs in retirement and securing your financial future.
Ready to Integrate Healthcare Planning into Your Financial Strategy?
Managing healthcare costs doesn't have to be a source of stress as you plan for retirement. As part of your holistic financial plan, we can help you strategically address these expenses. Our objective is to ensure that medical costs are a managed component of your financial journey, allowing you to focus on achieving financial freedom and securing the legacy you envision for your family.
Questions we can solve together:
● How can I plan for the costs of a future medical procedure?
● I don't have access to an HSA; where should I save money for future medical expenses that might arise?
● How much should I contribute to my HSA to maximize its benefits for my financial future and retirement planning?
● What are the best strategies for saving for healthcare in retirement given my specific financial situation?
● How can long-term care insurance fit into my overall retirement plan?
Recent Articles Written By Andrew:
Recent Publications Featuring Andrew:
Podcasts Featuring Andrew:
Fiduciary Financial Advisors, LLC is a registered investment adviser and does not give legal or tax advice. Information presented is for educational purposes only and does not intend to make an offer or solicitation for the sale or purchase of any securities. The information contained herein has been obtained from a third-party source which is believed to be reliable but is subject to correction for error. Investments involve risk and are not guaranteed. Past performance is not a guarantee or representation of future results.
Fiduciary Financial Advisors does not give legal or tax advice. The information contained does not constitute a solicitation or offer to buy or sell any security and does not purport to be a complete statement of all material facts relating to the strategies and services mentioned.
"All-Time-High" Anxiety? Relax.
We’ve all felt the anxiety when the market hits a new all-time high. But what if that feeling is based on a media narratives and emotion, rather than logic? We'll use data to explain why the market isn't defying anything, it's just doing its job; and why staying the course on a well-defined plan is more important than timing the market.
The Market Isn't Defying Gravity. It's Just Doing Its Job.
Read Andrew’s Story
Key Takeaways
Market highs are not a red flag. The fear that an up market "must come down" is a myth. All-time highs are a sign that the system is working exactly as it should and are a normal and expected part of a market with a positive expected return.
Market prices aren't arbitrary numbers. A stock is a "perpetual claim ticket" on a company's future earnings and dividends. Its value isn't fighting a force of nature but is based on the collective judgment of its future profitability.
Patience beats panic. Data shows that investing at a market high has generated similar returns to investing after a sharp decline over the subsequent one, three, and five years. Your efforts to improve results by trying to time the market is more likely to penalize them.
Your mind is your biggest opponent. The real challenge isn't the market itself, but managing the emotional responses it triggers. A disciplined strategy is more important than trying to time the market
Time, October 15, 1990 (High Anxiety); Money, August 1997 (Don’t Just Sit There… Sell Stock Now!)
There's a persistent myth in financial news, especially when the market is climbing: that stocks are "defying gravity" and are due for a painful fall. You see the headlines; the ones that talk about the market "heading back to Earth". It's a great story, but it's a terrible metaphor for how markets actually work.
Your investments aren't heavy objects being kept aloft by some mysterious effort. They're not a hot air balloon that must eventually descend. They are, in a far less poetic but more accurate sense, perpetual claim tickets on companies' future earnings and dividends. The value of a stock isn't fighting a force of nature; it's simply a reflection of the market's collective judgment on a company's future profitability. In other words, when stocks hit a new high, it's not a sign that the system is broken; it's a sign that it's working as expected.
Think about it: every day, thousands of businesses are working to innovate, grow, and generate profits. Their success, over time, is what drives market values higher. To put it bluntly, it would be difficult to imagine a scenario where investors freely put money into stocks with the expectation of losing money.
The Data Doesn't Lie.
The idea that you should avoid buying at market highs is a powerful emotional signal, but the data tells a different story. In fact, reaching new record highs is a normal and expected outcome if stocks have a positive expected return. Over the 94-year period ending in 2020, the S&P 500 Index produced a new high in more than 30% of those monthly observations.
But here’s the the real take: a study from Dimensional Fund Advisors shows that purchasing shares at all-time records has, on average, generated similar returns over subsequent one-, three-, and five-year periods to those of a strategy that purchases stocks following a sharp decline:
The numbers don't show a clear advantage to waiting for a drop. All they show is that staying invested pays off over time.
The Real Job of a Financial Advisor
Your biggest opponent isn’t the market; it's your own mind. Our human brains are conditioned to think that after a rise, a fall must follow, tempting us to "fiddle" with our portfolios. But as the data shows, these signals only exist in our imagination, and trying to act on them can hurt your long-term results.
That's where I come in. My job isn’t to predict the market, it’s to help you navigate your emotions and stick to the plan we've built together. It's about ensuring your portfolio is structured to handle the market's ups and downs so you can focus on what really matters: your business, your family, and your legacy.
We’re not fighting the laws of physics. We're embracing the power of a disciplined strategy.
Let's Talk About Your Strategy
If you're a business owner or a successful professional, you've already built your wealth on a foundation of discipline and long-term vision. Let’s make sure your financial plan is built with the same strategy.
Frequently Asked Questions (FAQ)
Q: What is "all-time-high anxiety"?
A: This is the common feeling of apprehension or hesitation that investors experience when stock prices reach a new record high. This feeling is often fueled by the belief that "what goes up must come down" and that a market downturn is imminent.
Q: Should I wait for the market to drop before investing more?
A: The data suggests that trying to time the market in this way is not an effective strategy. A study showed that purchasing stocks at all-time records has, on average, generated similar returns over subsequent one-, three-, and five-year periods to a strategy that purchases stocks following a sharp decline.
Q: How does a financial advisor help with this type of anxiety?
A: A financial advisor helps by providing a disciplined, long-term strategy. My role is to help you navigate your emotions and biases so you can stick to your plan, allowing you to focus on your personal and professional life while your wealth works for you.
Recent Articles Written By Andrew:
Recent Publications Featuring Andrew:
Podcasts Featuring Andrew:
Fiduciary Financial Advisors, LLC is a registered investment adviser and does not give legal or tax advice. Information presented is for educational purposes only and does not intend to make an offer or solicitation for the sale or purchase of any securities. The information contained herein has been obtained from a third-party source which is believed to be reliable but is subject to correction for error. Investments involve risk and are not guaranteed. Past performance is not a guarantee or representation of future results.
Fiduciary Financial Advisors does not give legal or tax advice. The information contained does not constitute a solicitation or offer to buy or sell any security and does not purport to be a complete statement of all material facts relating to the strategies and services mentioned.
Your Business May be Your Rocket Ship. But Where is Your Mission Command?
Your business is a rocket ship; an unparalleled engine for wealth creation. But relying on it for 100% of your net worth creates a dangerous concentration risk and is one of the biggest financial mistakes an owner can make. The single most important move for your family's long-term security is to consistently and strategically move money out of your business. This video is not about being less committed to your company; it’s about building a financial fortress around it. We break down the four critical strategies for building your family's "Mission Command": a structure of outside assets that protects your wealth, funds your life, diversifies your tax strategy, and secures your legacy for generations to come. Are you the CEO of your business, or the CEO of your family's future?
Why the smartest thing a successful business owner may do is systematically build wealth outside their company.
Read Andrew’s Story
Key Takeaways
Diversify Your Wealth: Relying solely on your business for wealth creates dangerous concentration risk. Building outside assets provides critical diversification.
Fund Your Life Separately: Use outside wealth to fund personal milestones like retirement and education, decoupling them from your business's performance.
Embrace Tax Diversification: Complement your business's pre-tax retirement plans with post-tax Roth accounts and taxable brokerage accounts to hedge against future tax changes.
Build a Complete Estate Plan: A true legacy plan goes beyond a will and includes trusts, powers of attorney, and strategies for liquidity and gifting to protect your family and assets.
In our last discussion, we broke down why comparing a dynamic business like the Lakers to a passive S&P 500 fund was like comparing a rocket ship to a passenger train. The business, with its leverage, cash flow, and tax advantages, is an unparalleled engine for wealth creation.
And I stand by that. Your business is likely the cornerstone upon which your family's greatest financial assets will be built.
So, what I'm about to say might feel a little hypocritical: The single most important financial move a successful business owner may make in their career is to consistently and strategically move money out of their business.
This isn't about being less committed to your company. It’s about being more committed to your family's long-term security. You’ve already built the empire; now it's time to build the fortress around it.
What is Concentration Risk for a Business Owner?
Being the owner is exhilarating. You control your destiny. The flip side? All of your financial destiny is tied to a single asset. We love to talk about diversification when it comes to a stock portfolio, but we often ignore the fact that for most owners, their business represents the least diversified portfolio imaginable.
It’s like being a Michelin-star chef who only eats his own cooking. The food is brilliant, but you’re crippling future growth by not expanding your, or your family’s, horizons.
Market shifts, industry disruption, a key employee leaving, or your own health can put the entire enterprise at risk. This is concentration risk. You've spent years building your golden goose; a savvy financial plan ensures you have a stockpile of golden eggs held safely in a completely different basket.
Why Fund Your Personal Goals Outside the Business?
Your company's balance sheet is not your personal balance sheet. The business needs to retain capital for growth, but your life has its own capital requirements. Systematically building wealth outside the business allows you to firewall your personal goals from your business's performance.
Retirement on Your Terms:
You may plan to sell the business for your retirement, but what if the perfect buyer doesn't show up the month you want to hit the golf course? What if the market is in a downturn and valuations are compressed? A separate, liquid nest egg gives you the power of choice. It means you can retire when you want to, not when you have to.
Funding Life’s Big Moments:
Your daughter's wedding, your son's college tuition, that vacation home you've been dreaming of; these things shouldn't be dependent on your company's Q3 revenue. Funding these goals with assets completely decoupled from your business removes immense pressure from both you and the company.
What is Tax Diversification and Why Does It Matter?
In the last article, we’ve established the incredible tax advantages of running a business; from deducting vehicles to super-charging retirement accounts. Plans like a 401(k) or a Cash Balance Plan allow for massive pre-tax contributions that lower your income today. But true tax strategy, like investment strategy, benefits from tax diversification.
Building wealth outside the business opens up a new set of tools:
The Roth Bucket:
Business retirement plans are fantastic for those massive pre-tax contributions, but you're creating a future tax liability. By funding Roth IRAs (or executing Roth conversions), you use post-tax dollars to build a bucket of money that is 100% tax-free in retirement. This is a critical hedge against the uncertainty of the future tax landscape
The Taxable Brokerage Account:
It sounds simple, but having a standard brokerage account, funded with after-tax money, is a cornerstone of liquid wealth. It's not locked up in a retirement plan, and when you sell assets held for more than a year, you benefit from lower long-term capital gains tax rates. It’s your financial multi-tool: liquid, flexible, and tax-efficient.
What Does a Complete Estate Plan Look Like?
For many business owners, an "estate plan" often means having a will and a buy-sell agreement. While essential, that’s like a master builder commissioning the quarrying of a mountain of exquisite marble but only drafting a blueprint for the front steps of the actual building he’s constructing. A true estate plan is the full architectural design for the entire multi-generational estate your business has given you the power to build.
The goal is to construct a legacy that protects your family from taxes, probate, and internal conflict. This requires several key structural elements:
Powers of Attorney and Medical Directives:
These are the most crucial, yet often overlooked, documents. Who makes financial decisions for your business and personal life if you're incapacitated? Who makes healthcare decisions on your behalf? Without these directives, your family could face a costly and agonizing court process to gain control, leaving your business and assets in limbo when they need stability most.
Trusts:
A Revocable Living Trust is the foundational drawing for your entire estate. It dictates how your non-business assets are structured and distributed, ensuring they pass to your heirs without the costly, time-consuming, and public process of probate. It provides the framework for the entire structure, giving you control over the final design
Strategic Liquidity:
This is where the challenge of fairness comes in, especially when some children are in the business and others aren't. How do you ensure equity without having to dismantle the main structure? This is where life insurance can become a critical utility. Often held within a specialized trust (like an ILIT), a policy can provide a tax-free, liquid infusion of capital to provide a cash inheritance to non-participating children or give the estate the cash needed to pay hefty estate taxes.
Strategic Gifting:
The tax code allows you to give to your heirs' by gifting significant amounts to them each year (as well as over your lifetime) tax-free. A strategic gifting program, specifically one where the gifts are given with a specific intended goal, methodically reduces the future size of your taxable estate while allowing you to see your family enjoy the security and comfort you’ve worked so hard to create.
Are You a Business Owner or a CEO of Your Family's Future?
Loving your business and protecting your family's future are not mutually exclusive goals. In fact, the latter requires you to look beyond the former.
Building a fortress of outside assets; liquid investments, tax-diversified accounts, and legacy-protecting trusts: is what separates a successful business owner from the founder of a financial dynasty. It’s the difference between merely launching a rocket and establishing a Mission Command that directs the entire operation.
Your business may be your powerhouse for creating wealth. A plan that strategically moves that wealth into your family's Mission Command is the blueprint for ensuring your mission succeeds for generations to come.
Recent Articles Written By Andrew:
Frequently Asked Questions (FAQ)
Q: Why should a business owner build wealth outside of their company?
A: Business owners should build wealth outside their company to diversify away from the concentration risk of having all their assets tied to one entity. This strategy provides liquidity for personal goals, creates retirement options not dependent on a business sale, and enhances family legacy planning.
Q: What is tax diversification for an entrepreneur?
A: Tax diversification is the strategy of holding wealth in different types of accounts to minimize future tax burdens. It involves balancing pre-tax retirement accounts (like a 401(k)) with post-tax accounts (like a Roth IRA) and taxable brokerage accounts, providing flexibility against a changing tax landscape.
Q: What are the most important parts of an estate plan besides a will?
A: For a business owner, a complete estate plan should also include: 1) Powers of Attorney and Medical Directives for incapacitation, 2) a Revocable Living Trust to avoid probate, and 3) strategies for liquidity (often using life insurance) and gifting to manage estate taxes and ensure fairness among heirs.
Q: How can a business owner ensure fairness when leaving the business to only some of their children?
A: A common strategy is to use life insurance, often held in a trust, to provide a tax-free cash payout equal to the business's value to the
Recent Publications Featuring Andrew:
Podcasts Featuring Andrew:
Fiduciary Financial Advisors, LLC is a registered investment adviser and does not give legal or tax advice. Information presented is for educational purposes only and does not intend to make an offer or solicitation for the sale or purchase of any securities. The information contained herein has been obtained from a third-party source which is believed to be reliable but is subject to correction for error. Investments involve risk and are not guaranteed. Past performance is not a guarantee or representation of future results.
Fiduciary Financial Advisors does not give legal or tax advice. The information contained does not constitute a solicitation or offer to buy or sell any security and does not purport to be a complete statement of all material facts relating to the strategies and services mentioned.
Business Ownership vs. Index Investing: A Deeper Look at the Buss/Lakers Debate
A popular stat suggests indexing the S&P 500 would have been a better investment than Jerry Buss's purchase of the Lakers. This article dismantles that myth, revealing how the real math of leverage, cash flow, and tax efficiency tells a much different, and more profitable, story about building true wealth through ownership.
Why the viral stat about the Lakers' sale misses the point on how real wealth is built.
Read Andrew’s Story
There's a fascinating piece of financial trivia that often circulates among investors and sports fans alike. It lays out a simple, and seemingly mind-blowing, comparison:
At first glance, the takeaway seems simple: even owning a storied franchise like the Los Angeles Lakers couldn't beat a simple index fund. But for savvy owners, advisors, and executives, this comparison immediately raises red flags. It represents a fundamental misunderstanding of how strategic wealth is built, and it overlooks the immense financial and personal advantages of business ownership.
This article is for anyone who suspects there's more to the story. We’re going to go beyond the surface-level analysis and break down what the one-dimensional math ignores, from the real financial returns to the priceless advantages that ownership provides.
Key Takeaways:
IRR vs. ROI: When accounting for leverage and annual cash flow, the Lakers investment likely produced an Internal Rate of Return (IRR) more than double that of the S&P 500.
Tax Efficiency: Business owners can use before-tax dollars and deductions (like Section 179 and QBI) to significantly increase their financial efficiency compared to passive investors.
Priceless Returns: The true value of ownership includes non-financial returns like legacy, hands-on experience, and networking opportunities that an index fund cannot provide.
The Problem with the $13 Billion Number
Let me be clear: the S&P 500 is a fantastic investment tool, and its long-term performance is a powerful force for passive wealth creation. The problem isn’t with the index; it's with using it as a simplistic benchmark against a complex, multi-faceted asset like a business. The headline comparison falls apart under the weight of two realities that every business owner understands intuitively: Leverage and Cash Flow.
The Initial Investment Wasn't $67.5 Million in Cash
The first flaw in the comparison is the initial figure. Jerry Buss was a master of the deal. The $67.5 million transaction was for a portfolio of assets that included the Lakers (NBA), the Los Angeles Kings (NHL), The Forum arena, and a 13,000-acre ranch. More importantly, the deal was incredibly complex and highly leveraged. It involved multiple escrows, property swaps (including a transaction involving the Chrysler Building), and the efforts of over 50 lawyers. While the exact cash out of his pocket is not public, reports from the time estimated that Buss’s actual cash invested in the entire transaction may have been as low as $125,000, not including closing costs. Another analysis suggests his down payment was closer to $16 million. Let's be conservative and use the higher figure. If a $16 million investment grows into a stake worth billions, the return multiple is astronomical; far exceeding the S&P 500. This is the power of using leverage to control an asset, a tool unavailable to a typical index fund investor.
The Final Sale Price Ignores 45 Years of Income
The second, and arguably bigger, flaw is that the $10B valuation only represents the asset's value at the end. It completely ignores the decades of annual income the Lakers generated for the Buss family. The Lakers are a financial powerhouse. Even going back a decade, Forbes estimated the team's operating income for 2015 was $133 million. For the 2022-2023 season, their revenue was $516 million with an operating income of $159 million. This doesn't even account for the team's league-leading local TV deal with Spectrum SportsNet, worth hundreds of millions per year. While precise distributions are private, the publicly available data shows that the team generated billions in both revenue and profit over the Buss family's ownership tenure. That profit is money that could be enjoyed, reinvested in other ventures, or used to more quickly service the very debt that bought the team in the first place. This is why, for complex assets, a simple return multiple is the wrong tool. The only way to properly measure a deal like this is with a metric that accounts for all the cash flows (in and out) over the entire life of the investment: the Internal Rate of Return (IRR).
A Tale of Two IRRs: The Headline vs. Reality
The table below models the two approaches. The first column details the 'headline' scenario, which assumes an unlevered $67.5 million investment in the S&P 500. The second column models the more realistic 'reality' scenario of a leveraged $16 million investment in the Lakers, including estimated annual distributions.
The key takeaway is staggering. The Lakers ownership deal generated nearly an identical total net profit, but did so using less than a quarter of the initial capital and produced an IRR that was more than double that of the S&P 500.
The Money You Don’t See (Cash Flow & Perks)
The fundamental error in the "S&P is better" argument is its failure to recognize that a business is not a static number on a screen; it’s a living, breathing engine designed to generate income. The final sale price of an asset like the Lakers ignores the decades of cash flow produced along the way. This ongoing financial benefit generally comes in two forms: direct compensation and integrated perks.
The Annual Paycheck: Salary & Distributions
Unlike a passive stock holding, a profitable business pays its owner. For an active owner, this typically begins with a reasonable salary for the work they perform in the company. This is the reward for the day-to-day effort of running the enterprise. But the more significant reward comes from the profits. After all expenses are paid, including that salary, the remaining profit (the "net income") belongs to the owner and can be taken as a distribution (or dividend). This is the direct return on investment an owner receives for their capital and risk. This ability to generate cash without selling the underlying asset is a cornerstone of an owner's financial freedom
The "Lifestyle Asset": An Apples-to-Apples Look at Your Dollars
Beyond direct pay, the ability to run legitimate expenses through a business creates a massive financial advantage through the power of paying with before-tax dollars versus after-tax dollars. To show the real-world impact, let's create a clear, apples-to-apples comparison using only the 2025 federal income tax brackets for simplicity. Imagine two individuals: one is a high-income salaried employee, and the other is a business owner. Both need a new $80,000 vehicle. For an employee at this income level, their earnings for that purchase alone would place them in the 24% federal marginal tax bracket if they were to purchase the vehicle outright. This means the last dollars they earn, the ones they'd use for a large purchase, could be taxed at an even higher rate.
The Salaried Employee:
To have $80,000 in cash to buy the car, they must first earn that money and pay federal income tax on it. To get $80,000 of take-home pay, they would need to earn approximately $105,263. After paying 24% in federal taxes on those earnings (about $25,263), they are left with the $80,000 they need.
$105,263(Gross Pay)−$25,263(24%Federal Tax Owed)=$80,000(Net Pay)
The Business Owner:
The owner also needs an $80,000 vehicle, which will be used solely for legitimate business purposes. The business can purchase the vehicle directly. That $80,000 is a business expense. Thanks to tax provisions like Section 179 or bonus depreciation, the business may be able to deduct the full purchase price from its income in the first year. This deduction reduces the business's taxable income by $80,000, saving the company (and by extension, the owner) $19,200 in federal taxes (24% of $80,000).
The Bottom-Line Impact
To afford the exact same vehicle, the employee had to use $105,263 of their gross earning power. The business owner, by using their company as the purchaser of the vehicle, effectively only used $60,800 of their earning power ($80,000 cost - $19,200 tax savings). This isn't a loophole; it's a fundamental principle of the tax code designed to encourage business investment.
A Masterclass in Tax Efficiency
If cash flow is the engine of day-to-day wealth, then tax strategy is the high-performance oil that keeps that engine running at maximum efficiency. It's not about 'finding loopholes'; it's about strategically using a rulebook that is specifically designed to reward business investment and growth. For a business owner, the U.S. Tax Code provides a rich and dynamic playbook for legally minimizing tax liability. This advantage is built on three pillars: choosing the right foundation, understanding the full universe of deductions, and leveraging industry-specific opportunities.
The Foundation: Why Your Entity Structure is Your Financial Blueprint
Before a single dollar is earned, the most critical decision a business owner makes is choosing their entity structure. This choice dictates how profits are taxed, what deductions are available, and how the owner is compensated.
LLC (Limited Liability Company):
A popular starting point, the LLC is a legal entity (not a tax entity) that offers liability protection. Many sole proprietors will elect to have this treated as a "disregarded entity" for tax purposes, making filing simpler as it can all be done on their personal return: the 1040. As income increases, the next step is to choose how the entity is taxed.
S-Corporation (S-Corp):
For many profitable small businesses, the S-Corp is the gold standard of tax efficiency. It allows the owner to pay themselves a reasonable salary (subject to payroll taxes) and then take any additional profits as distributions. These distributions are not subject to self-employment taxes, which can result in thousands of dollars in annual tax savings compared to taking all compensation as salary.
C-Corporation (C-Corp):
The structure of major enterprises like the Lakers, a C-Corp is a separate tax-paying entity. While its profits are subject to corporate income tax, potentially leading to double taxation, it offers maximum flexibility for growth, raising capital, and providing more extensive, and deductible, employee benefits; many of which can also be additional forms of compensation for the owner.
The Universe of Deductions: Lowering Taxable Income Year After Year
Once the structure is set, owners can leverage a vast array of legitimate business expenses to lower their taxable income. We saw the power of this with the vehicle example, but it extends much further into building personal wealth.
A Deeper Dive: Super-Charging Retirement Savings
This is where your choice of entity becomes incredibly powerful. A primary example is in retirement savings. While a traditional employee might be limited to their company's 401(k), a business owner can establish plans with dramatically higher contribution limits. Let's look at the popular Solo 401(k) for an owner with no employees. For 2025, the savings potential is split into two parts:
The Employee Contribution: The owner acts as their own "employee" and can defer up to 100% of their salary, up to a maximum of $23,500 for 2025.
The Employer Contribution: The business then acts as the "employer" and can contribute up to 25% of the owner's compensation. The power is in combining them. The total contributions from both sources cannot exceed $70,000 for 2025. This allows a business owner to save nearly three times more in a tax-advantaged account than a typical employee, drastically reducing their current taxable income while accelerating their retirement goals. A SEP IRA is another strong option, consisting solely of employer contributions up to 25% of compensation.
This entire strategy is made possible by the salary and compensation structure you can create with the right business entity.
For owners looking to save even more aggressively, a Cash Balance Plan can be a powerful tool. This is a type of "private pension" that allows for massive, age-dependent, tax-deductible contributions that can often exceed six figures annually. These plans can also be used in addition to a 401(k), allowing for a stacked approach that can drastically reduce a high-income owner's tax bill while rapidly building wealth.
Other High-Impact Deductions
Beyond retirement, an owner has a toolkit of other powerful deductions to enhance financial efficiency:
The Qualified Business Income (QBI) Deduction: Also known as Section 199A, this is one of the most significant deductions available to owners of pass-through businesses (S-Corps, partnerships, sole proprietorships). It allows for a deduction of up to 20% of qualified business income directly from your taxable income. It's a complex deduction with limitations based on income level and business type, but for those who qualify, it's an incredibly powerful tax-saving tool.
Health Insurance Premiums: For self-employed individuals and S-Corp owners, the cost of health insurance premiums is often 100% deductible, turning a major personal expense into a significant tax deduction. For businesses electing to file as a C-Corp, the premiums for all employees are deductible to the business.
Asset Depreciation: This is a game-changer. When a business buys a significant asset: be it manufacturing equipment, computer hardware, or even a sports stadium; it can deduct the cost over time. Provisions like Section 179 and bonus depreciation often allow an owner to deduct the entire cost of an asset in the year it was purchased, creating a massive, immediate reduction in taxable income.
Industry-Specific Opportunities: It's Not Just for Sports Teams
Different industries also benefit from tailored tax incentives designed to encourage specific economic activities. This proves that tax advantages aren't just for billion-dollar franchises. Some examples are as follows:
Real Estate Investors: Beyond standard deductions, real estate professionals can use depreciation as a powerful tool to create losses that can offset other income. Advanced strategies like cost segregation studies can accelerate this depreciation, maximizing tax savings in the early years of owning a property.
Tech & Manufacturing: These industries can benefit from the R&D Tax Credit, a significant dollar-for-dollar credit for expenses related to innovation and improving products or processes.
Professional Services (Doctors, Lawyers, Consultants): For these owners, the primary advantage often lies in optimizing the S-Corp structure for salary and distributions and maximizing contributions to sophisticated retirement plans, like a defined benefit or cash balance plan, which allow for even larger, six-figure deductions.
The Priceless Premiums: Legacy, Experience, and Opportunity
If we stopped after the financial analysis, we would still be missing the most important part of the story: the elements of ownership that don't appear on a balance sheet but represent what is often the deepest forms of wealth. An index fund can give you a return. A business can give you a life. This "builder's premium" is a powerful form of return that manifests in three key areas:
The Legacy Asset: Building for the Next Generation
You cannot teach executive-level life skills by showing your children a brokerage statement. An entrepreneur creates an environment where the next generation can gain hands-on experience. When Jerry Buss passed away, he didn't just leave his children stock; he left them an empire. This is the ultimate goal for many entrepreneurs: creating a generational asset that provides purpose and opportunity not only for them, but those they most care about.
The Experiential Return: The 'Fun' Factor
A purely numerical comparison misses a simple, undeniable fact: the journey of building a business is often its own reward. The passion, the challenges, and the victories create a psychological income that can be more valuable than any financial return. The word "wealth" itself is derived from an Old English term for a state of being happy and healthy, not the financial riches that we often equate it with in modern times.
The Opportunity Network: Doors Opened and Deals Done
Owning a significant business creates a universe of opportunities that passive investing cannot. It puts you in rooms with other high-level operators, investors, and centers of influence. This network is, in itself, an asset that can lead to new ventures and strategic partnerships far beyond the scope of the original business.
Are You Building a Nest Egg or an Empire?
So, where does this leave our comparison? We've seen that the initial headline stat withers under scrutiny when you account for leverage, cash flow, and tax efficiency. The financial return on an asset like the Lakers is in a different universe than that of a passive index. But the analysis runs deeper. We've explored the benefits that can't be quantified: legacy, experience, and other opportunities.
The S&P 500 is an exceptional tool for building wealth passively. But it is just that: a tool. It is not an engine for creating a family legacy or a tax-efficient cash flow machine. To compare it to owning and building a business isn't just comparing apples to oranges; it's comparing a passenger train to a rocket ship. Both can move you forward, but they operate in entirely different dimensional planes with vastly different purposes.
Ultimately, your financial strategy must reflect what you are trying to build. If your goal is simply a number, a passive approach may be sufficient. But if you are building an engine for your family, for your life, for your future; you need a financial partner who understands that your business may be your most powerful asset. You need a plan that enhances its growth, not one that fights it.
Recent Articles Written By Andrew:
Frequently Asked Questions (FAQ)
Q: Is owning a business a better investment than the S&P 500? A: While the S&P 500 is an excellent passive tool, this analysis shows that a well-run business, utilizing leverage, cash flow, and tax advantages, can offer a significantly higher Internal Rate of Return and provides non-financial benefits like legacy and experience.
Q: What is the biggest tax advantage of an S-Corp? A: A primary advantage is the ability to pay yourself a "reasonable salary" and take remaining profits as distributions, which are not subject to self-employment taxes.
Q: What is the IRR? A: The Internal Rate of Return (IRR) is a financial metric that calculates an investment's profitability by accounting for all cash inflows and outflows over its entire lifetime, making it more accurate for complex assets than a simple return on investment.
Recent Publications Featuring Andrew:
Podcasts Featuring Andrew:
Fiduciary Financial Advisors, LLC is a registered investment adviser and does not give legal or tax advice. Information presented is for educational purposes only and does not intend to make an offer or solicitation for the sale or purchase of any securities. The information contained herein has been obtained from a third-party source which is believed to be reliable but is subject to correction for error. Investments involve risk and are not guaranteed. Past performance is not a guarantee or representation of future results.
Fiduciary Financial Advisors does not give legal or tax advice. The information contained does not constitute a solicitation or offer to buy or sell any security and does not purport to be a complete statement of all material facts relating to the strategies and services mentioned.
House Rich, Cash Poor: Managing Wealth When Your Largest Asset is Real Estate
Managing wealth when your largest asset is real estate requires thoughtful strategies. From tax-efficient tools like 1031 exchanges to diversification through DSTs and UPREITs, each option offers unique benefits and trade-offs. Finding the right path depends on balancing growth, liquidity, and long-term goals while navigating the complexities of real estate investment.
For many Americans, homeownership is their most significant financial asset. However, real estate investments can leave much of your wealth tied up in real estate, and limited liquidity for a more balanced investment strategy.
Fortunately, several strategies exist to manage real estate wealth tax-efficiently, turning equity into liquidity while preserving long-term value. Below, we explore tools like 1031 exchanges, Delaware Statutory Trusts (DSTs), and 721 exchanges (UPREITs) to help you make informed decisions about your financial future.
Strategies for Real Estate Wealth Management
1031 Exchange
The 1031 exchange is one of the most commonly used tools for managing real estate capital gains. This IRS-approved strategy allows you to defer taxes when you sell an investment property and reinvest proceeds into another “like-kind” property.
Pros
Capital Gains Tax Deferral: By deferring taxes, you keep more capital available for reinvestment, enhancing the potential for your wealth to grow over time. This strategy can be applied multiple times as your portfolio evolves, enabling you to align your investments with changing goals or market opportunities.
Estate Planning Benefits: Upon inheritance, heirs receive a stepped-up cost basis, eliminating the deferred capital gains taxes that have been accumulating by using this approach.
Cons
Stringent Timelines: You must identify a replacement property within 45 days of selling your current one and complete the purchase within 180 days.
Active Management Required: You remain responsible for property upkeep and operations unless you combine this strategy with a passive structure like a DST. More on that to come.
Strict Property Rules: Only real property, such as land or buildings, qualifies under 1031 exchange rules, excluding personal property, stocks, or other asset types. This limitation narrows flexibility for investors who may wish to diversify beyond real estate.
When to Use It: Ideal for active investors aiming to upgrade properties, defer taxes, or diversify their portfolios while staying involved in management.
Delaware Statutory Trust (DST)
DSTs provide a way to own fractional shares of large, professionally managed properties while retaining eligibility for 1031 exchanges.
Pros
Passive Investment: Investors enjoy hands-off property ownership with management handled by professionals. This is perfect for those seeking income without operational headaches.
Access to High-Quality Assets: DSTs often include institutional-grade properties like office buildings, multifamily units, or industrial spaces. They offer diversification across geography, tenant types, and sectors.
Ongoing 1031 Eligibility: You can defer taxes on the eventual sale of DST shares by reinvesting through another 1031 exchange.
Cons
Limited Liquidity: DST shares are illiquid, with investors needing to wait for the property’s eventual sale to access funds.
Lack of Control: Investors have no say in operational or sales decisions, which could impact returns.
When to Use It: Best for investors looking for passive income while still leveraging the tax benefits of 1031 exchanges.
721 Exchange (UPREIT)
The 721 exchange allows property owners to convert real estate into operating partnership (OP) units in a Real Estate Investment Trust (REIT), offering exposure to a diversified real estate portfolio.
Pros
Tax Deferral: Immediate deferral of capital gains taxes during the exchange process.
Diversification: Instead of holding a single property, you gain fractional ownership in a REIT, which may include residential, commercial, and industrial properties across markets.
Improved Liquidity: REIT shares are easier to sell compared to physical real estate, offering greater flexibility if you need cash.
Simplified Estate Planning: REIT shares can be divided among heirs more easily than physical properties.
Cons
No Re-Entry to 1031: Once in a REIT, you cannot use 1031 exchanges for future tax deferrals.
Market Volatility: The value of REIT shares can fluctuate, introducing new risks compared to holding a single property.
When to Use It: Ideal for investors ready to exit property management entirely, seeking diversification and either a more liquid portfolio or access to cash.
Choosing the Right Path
Deciding on the right strategy for managing real estate wealth requires careful consideration of your financial goals, risk tolerance, and long-term priorities. Each option—whether a 1031 exchange, DST, or UPREIT—offers specific benefits that cater to different needs, but also comes with trade-offs that must be weighed.
For those seeking to maximize growth, strategies like the 1031 exchange allow for tax-deferred reinvestment, enabling properties to evolve alongside your financial objectives. If diversification and passive management are priorities, transitioning into structures such as DSTs or UPREITs can provide exposure to a broader range of assets without the burdens of direct property management. When planning for future generations, these tools also facilitate tax-efficient wealth transfer, simplifying estate planning and easing the complexities of distribution.
Ultimately, the best approach depends on how you balance factors like liquidity, diversification, and tax efficiency against your personal and financial goals. Thoughtful planning and a clear understanding of your options are essential to ensuring that your strategy aligns with both current needs and future aspirations.
Recent Articles Written By Andrew:
Recent Publications Featuring Andrew:
Podcasts Featuring Andrew:
Fiduciary Financial Advisors, LLC is a registered investment adviser and does not give legal or tax advice. Information presented is for educational purposes only and does not intend to make an offer or solicitation for the sale or purchase of any securities. The information contained herein has been obtained from a third-party source which is believed to be reliable but is subject to correction for error. Investments involve risk and are not guaranteed. Past performance is not a guarantee or representation of future results.
Fiduciary Financial Advisors does not give legal or tax advice. The information contained does not constitute a solicitation or offer to buy or sell any security and does not purport to be a complete statement of all material facts relating to the strategies and services mentioned.
Healthcare expenses are a critical and often unpredictable component of any financial plan. As a successful professional, you can't afford to let surprise medical bills compromise your long-term goals for asset growth and legacy preservation. Our strategic framework outlines eight actionable steps to help you move from reactive expense management to proactive financial control. We'll show you how to leverage tax-advantaged accounts, optimize your insurance coverage, and integrate long-term care planning to safeguard your wealth against the rising cost of health.