Is Your Business Ready to Fund Your Retirement?

Baddest Good Boy before the Razorback Handicap, Feb 23, 2025. Photo by Christa Jordan.

For small business owners in the thoroughbred racing industry—jockeys, trainers, breeders, and other horsemen—planning for retirement often falls to the bottom of a long list of priorities. However, failing to create a strategy for your financial future could leave you without the retirement you deserve after a lifetime of hard work. The truth is, there are only two paths to funding retirement for small business owners:

1. Build and sell the business to fund retirement.

2. Extract income from the business during its operation and invest it elsewhere.

Let’s explore these options and why the second scenario—extracting and investing business profits—is the most viable for nearly all small businesses in the horse industry. We’ll also delve into actionable steps you can take today to secure your financial future.

The Myth of Selling Your Business for Retirement

Many business owners hold onto the idea that they’ll eventually sell their business and use the proceeds to retire comfortably. While this is a possibility for some, the reality is much less certain for small businesses in niche industries like thoroughbred racing. Here’s why:

• Limited Market: Unlike larger, scalable businesses, a training or breeding operation often depends heavily on the owner’s skills, relationships, and reputation. Once you step away, much of the value disappears. Buyers may be hesitant to invest in a business that lacks inherent, transferable value beyond the current owner. And jockeys have nothing to sell as their business is literally themselves.

• Unpredictable Valuation: Assets like horses, equipment, and facilities have highly variable values tied to market conditions, making it difficult to rely on a sale as your retirement plan. The worth of these assets can fluctuate based on everything from age and economic trends to the success of particular racing seasons.

• Buyer Scarcity: Finding a buyer who is both capable and willing to take over your business can be challenging, especially in a specialized field like thoroughbred racing. The niche nature of this industry limits the pool of prospective buyers who understand its unique demands.

If your retirement plan hinges on selling your business, you’re taking a significant financial gamble. While preparing your business for sale is always wise, the reality is that the odds are against you.

The Practical Path: Extracting Income and Investing for Retirement

For most small business owners, including those in the horse industry, the second scenario—extracting profits from the business and investing them—is the only reliable way to build a retirement fund. This strategy ensures that you’re not dependent on uncertain factors like market timing or finding a buyer for your business. Here’s why this approach is essential:

1. Control Over Savings: By setting aside a portion of your profits regularly, you take charge of your financial future. You don’t have to rely on specific external events or market conditions to secure your retirement. Instead, you build a steady, predictable path toward financial independence.

2. Diversification: Investing outside your business spreads your risk across different assets, such as stocks, bonds, and real estate. This diversification shields your retirement savings from industry-specific downturns, such as a bad racing season or unexpected veterinary expenses.

3. Compounding Growth: The earlier you start investing, the more time your savings have to grow through the power of compounding. Even small, consistent contributions can grow into significant retirement assets over time. For example, investing $500 per month at a 7% annual return can grow to nearly $600,000 in 30 years.

4. Flexibility: Unlike relying on a business sale, building an investment portfolio gives you financial flexibility. You can retire on your terms without needing to find a buyer for your business. This flexibility is especially valuable in an industry as unpredictable as thoroughbred racing.

5. Peace of Mind: Knowing that your retirement doesn’t hinge on selling your business or achieving a specific profit margin allows you to focus on running your business without added stress.

Why This Matters in the Equine Industry

The horse industry is unique, but it faces many of the same challenges as other small business sectors. Here’s why extracting and investing profits is especially critical for professionals in thoroughbred racing:

• High Overhead: Maintaining horses, paying staff, and covering operational expenses often leaves little room for savings unless proactively managed. Strategic financial planning is essential to ensure day-to-day costs don’t entirely consume your profits.

• Irregular Income: Racing earnings, breeding fees, and other revenues can be inconsistent, making it even more critical to prioritize saving during profitable periods. A disciplined approach to saving ensures that lean times don’t derail your retirement goals.

• Physical Demands: Careers in thoroughbred racing are physically taxing, and many horsemen and jockeys are forced to retire earlier than in other industries due to age or injury. A shorter career span means less time to save and invest, making it even more crucial to start early. Of course, you may be able to start a second career, but do you want to be forced into that?

• Economic Sensitivity: The horse industry is deeply affected by economic trends, making diversification outside the industry a vital component of a robust retirement plan.

Don’t Let Your Business Be Your Only Plan

If you’re not consistently saving a portion of your business profits and investing them for the future, you’re essentially betting your retirement on a high-risk, low-probability scenario. Instead, take these steps to ensure your business supports your retirement:

1. Assess Your Finances: Determine how much income your business generates and identify areas where you can reduce expenses to free up money for retirement savings. A detailed financial review can uncover opportunities to boost profitability.

2. Create a Savings Plan: Commit to saving a specific percentage of your profits each month or quarter. Automating this process can help make it a consistent habit. For instance, allocate a specific portion of your earnings to a dedicated retirement account.

3. Invest Wisely: Work with a financial advisor like me to build a diversified investment portfolio tailored to your goals, timeline, and risk tolerance. Your advisor can help you navigate complex investment options.

4. Plan for the Unexpected: Ensure you have an emergency fund and appropriate insurance coverage to protect your financial stability if something goes wrong. This safety net allows you to maintain your retirement savings even in tough times.

5. Monitor and Adjust: Regularly review your financial plan and make adjustments as needed. Life changes, industry shifts, and market conditions can all impact your retirement strategy, so staying proactive is key.

The Bottom Line

For thoroughbred racing professionals, the key to funding retirement lies in proactively saving and investing a portion of your business profits. By starting now, you can build a financial foundation that ensures you’ll be able to enjoy retirement, whether your career spans decades or just a few years. Don’t wait for the perfect buyer or hope for a windfall—take control of your retirement today.

With the right plan in place, you can achieve financial independence and enjoy a comfortable retirement, regardless of the unpredictable nature of the horse industry. Start planning today to ensure a stable and rewarding future.

Avoiding Tax Underpayment Penalties in the Thoroughbred Industry

Photo by Erik MacLean

The racing industry has some of the highest highs and the lowest lows of any vocation. For most people in the industry, their business profits and losses tend to track closely with those emotional highs and lows. A win at the track or a successful sale can bring a rush of euphoria, while setbacks can feel devastating. However, when it comes to your taxes, riding that emotional rollercoaster is a risky strategy.

The Challenge of Early-Year Tax Projections

In other posts, I’ve emphasized the importance of staying on top of your business profits and losses and regularly updating your tax estimates so you pay the right amount of taxes at the right time. But let’s face it: for many in the racing and breeding business, projecting a realistic full-year estimate by April 15th—the deadline for your first quarterly estimated payment—is no small feat.

For example, if you’re in the breeding business like I am, most of your income arrives in the second half of the year, with the yearling sales kicking off in July and the weanling sales wrapping things up in November. That kind of income pattern makes early-year tax projections especially challenging.

The Consequences of Underpaying Taxes

Unfortunately, getting your estimated tax payments wrong can have serious consequences. If you don’t pay in enough throughout the year, you’re not only facing a large tax bill when you file but also potential penalties for underpayment. That’s an added expense no one wants.

The IRS Safe Harbor Rule: Your Safety Net

Fortunately, there’s a way to protect yourself: the IRS safe harbor rule. This rule provides a safety net to help you avoid underpayment penalties, and it comes in two forms:

Option 1: The Prior-Year Safe Harbor

The first method relies on your previous year’s tax liability. If you pay in at least 100% of the total tax you owed last year (110% if your adjusted gross income was over $150,000), you’ll meet the safe harbor requirements and avoid penalties, even if your actual tax liability is higher this year.

For many in the racing industry, where income can be unpredictable, this is often the safer and more reliable option. It provides a fixed target and removes some of the guesswork from the equation.

Option 2: The Current-Year Safe Harbor

The second method is based on your actual income for the current year. If you calculate your tax liability in real time and ensure you’ve paid at least 90% of what you’ll owe by year-end, you’ll also meet the safe harbor requirements.

While this method can save money if your income is significantly lower than the prior year, it requires frequent updates to your income projections and tax estimates—a tall order in an industry with so many variables.

Why the Prior-Year Safe Harbor Often Wins

Given the variability in racing and breeding income, the prior-year safe harbor method is often the better choice. It’s predictable and gives you a concrete benchmark to aim for, regardless of how your year unfolds. While it might result in slight overpayment if your income drops, it’s a small price to pay for the peace of mind that comes with avoiding penalties.

Mixed-Income Households: Special Considerations

It’s important to note that the safe harbor rule applies to your combined household tax liability, even if your spouse has a W-2 job with tax withholding.

While W-2 income generally has taxes withheld throughout the year, those with self-employment or variable income—like many in the racing industry—often have less predictable earnings and no automatic withholding. In this case, the taxes your spouse’s employer withholds may not be enough to cover your total household liability.

By using the safe harbor rule, you can ensure that your combined tax payments meet the required thresholds, reducing the risk of penalties. This makes choosing the right safe harbor method even more critical for couples with mixed income types.

The Bottom Line

Staying compliant with your tax obligations doesn’t have to feel like trying to pick the winning horse in a crowded field. By understanding and leveraging the IRS safe harbor rule, you can avoid costly penalties and keep your focus on what matters most: growing your business and enjoying the ride.

Evaluate your situation carefully and choose the safe harbor method that works best for you. Just like in racing, preparation and strategy are the keys to long-term success. With the right approach, you’ll ensure that both your financial and professional journeys are on the right track.

Lastly, keep in mind that this article primarily addresses this topic at the federal level. Individual states will have their own tax rules. Some states make every effort to match their tax rules to federal tax rules but many states do not.

If your tax-preparer, accountant, CPA, or financial advisor is not proactive in helping you navigate the financial aspects of your thoroughbred business, reach out to me at Derek@TrophyPointFP.com.

Are Hidden Tax Penalties Inflating Your Tax Bill?

The author visiting Mind Your Mo in training at the Thoroughbred Center. Photo by Kristyn Whitican, Lexington, KY.

If you’re a racing jockey, you know all too well how unpredictable your income can be. One week, you’re earning a big payday from a major win, and the next, you might have little to no income. This inconsistency makes it especially tough to know how much to pay in estimated taxes, which can lead to unexpected penalties that quietly add to your tax bill.

Are you unknowingly paying these penalties?

Why Do Underpayment Penalties Exist?

The IRS requires taxes to be paid throughout the year, not just at tax time. For salaried employees, this happens automatically through employer withholding. But as a jockey, most of your income comes from riding fees, purse winnings, and endorsements, which often don’t have tax withholding. Instead, you’re expected to make quarterly estimated tax payments.

If you underpay your estimated taxes during the year, the IRS may impose a penalty—even if you pay your total taxes owed when you file your return. These penalties exist to ensure taxpayers keep up with their obligations, but for someone like you, whose income fluctuates wildly, meeting the quarterly deadlines can be a significant challenge.

How Underpayment Penalties Hide in Your Tax Return

Underpayment penalties are calculated using IRS Form 2210, the “Underpayment of Estimated Tax by Individuals, Estates, and Trusts.” However, this form often gets buried in hundreds of pages of tax forms and documents, making it easy to overlook.

What’s worse, the penalties themselves are usually rolled into the “amount due” on your tax return, without any obvious explanation. That means you could be paying these penalties year after year without even realizing it. The result? A tax bill that’s higher than it should be.

Why It’s Tough to Get Estimated Tax Payments Right as a Jockey

The racing industry is all about highs and lows. Your income depends on your performance, the quality of horses you ride, and the frequency of races you participate in. Early in the year, income might be low, while the summer and fall bring big purses and riding opportunities.

This unpredictability makes it nearly impossible to know how much to pay in estimated taxes at the start of the year. If you pay too little, penalties add up. If you pay too much, you’re parting with cash that you might need for travel expenses, gear, or even healthcare.

How to Find Out If You’re Paying Penalties

To see if you’re being penalized, ask your tax preparer to include a copy of IRS Form 2210 with your return. This form breaks down how much you’re being charged for underpayment penalties. If you prepare your own taxes, check your software’s reports section for a detailed breakdown of penalties and interest.

Understanding whether you’re paying penalties is the first step to fixing the problem. By knowing where your tax dollars are going, you can start to take control of your finances.

What’s Next?

If you’ve been paying underpayment penalties, don’t worry—there’s a solution. The IRS safe harbor rule can help you avoid penalties, even if your estimated payments aren’t perfect. In the next article, we’ll explain how the safe harbor rule works and how it can provide peace of mind for jockeys with unpredictable income.

Stay tuned to learn how to take the reins on your taxes and avoid unnecessary penalties!

Lessons from a Dinner Table Debate: What Jockeys and Horsemen Can Learn About Financial Priorities

At a recent dinner with friends, I found myself entertained by an unexpectedly passionate debate about car maintenance. The topic? How often you should check your car’s oil.

Friend #1’s approach: She checks her oil before every drive, just in case.

Friend #2’s approach: She never checks her oil and relies entirely on the dealer’s service department to ensure everything is in order. From her perspective, the worst-case scenario—an engine blowout—is covered by warranty.

For ten minutes, they argued their cases: vigilance versus trust in systems. I laughed, not because the debate was trivial, but because both perspectives have merit (also because it was funny that they just thought each other's position was absurd). The truth is, their choices reflect personal priorities, preferences, and opportunity costs.

How Does This Relate to the Racing Industry?

As a jockey, trainer, or horse owner, your financial decisions often mirror this debate. Some of you are "check the oil every drive" types: you meticulously monitor your income, expenses, and your horses! Others may take a more hands-off approach, trusting professionals to guide you.

Neither approach is inherently wrong. The key, however, is making a deliberate decision.

Breaking Down the Priorities

The Proactive Approach

Friend #1’s method works because she values control and precision. She may enjoy the hands-on aspect of car maintenance or simply prefer the lower cost of buying a used car and maintaining it herself. In the racing world, this might look like:

• Budget-conscious trainers who carefully track every expense.

• Jockeys who invest time learning about personal finance to manage their earnings effectively.

• Owners who strategize every purchase and mating and keep a close eye on their stable’s cash flow, profitability, and ability to pay upcoming expenses.

This approach requires diligence but can help mitigate risks and stretch your resources further.

The Delegated Approach

Friend #2 represents a different mindset. She’s willing to pay a premium for peace of mind, trusting her dealer’s warranty and service plan. Her time is better spent elsewhere, and she’s comfortable with the trade-off. In your world, this might look like:

• Relying on financial advisors to manage your investments and taxes.

• Hiring experienced staff to oversee day-to-day stable operations.

• Choosing top-tier service providers to ensure your horses get the best care.

This approach can save time and stress, allowing you to focus on your core strengths—whether that’s riding, training, or business development.

Opportunity Costs in Action

Every decision has an opportunity cost. For Friend #1, the time spent checking oil could be used elsewhere. For Friend #2, the added expense of a new car and maintenance plan might reduce her financial flexibility. Similarly, in the racing industry:

• Time spent on detailed financial management could take away from training or competing. 

• Financial and tax mistakes and misunderstandings can be costly.

• Outsourcing everything could lead to missed opportunities or higher costs.

The key is finding the balance that works for you.

Which Approach Works Best for You?

Your financial strategy, like your approach to horse care, should reflect your unique circumstances:

• Are you comfortable with details, or do you prefer to delegate?

• Do you have the time and interest to manage your finances closely?

• What trade-offs are you willing to make to focus on your priorities?

Final Thoughts

Whether you’re a "check the oil every drive" type or a "trust the warranty" person, the goal is the same: keeping your financial engine running smoothly. By understanding your priorities and making intentional choices, you can build a strategy that supports your success in the racing industry and beyond.

So, which type are you? And how does it influence your approach to managing your career and finances?

As you think about this topic. If you come to the conclusion that you want an experienced financial planner on your side of the table, reach out to me at Derek@TrophyPointFP.com.

Jockeys: 7 Tax Moves to Consider in 2025

As a horse racing jockey, managing your finances efficiently is critical to maintaining long-term financial success. With the unique income structure and expenses involved in your profession, careful tax planning can help you maximize earnings and minimize liabilities. Here are essential tax moves jockeys should consider for 2025.

1. Develop a Bookkeeping Process or Hire a Bookkeeper

Accurate and consistent bookkeeping is the foundation of good business and tax planning. Jockeys often have numerous business-related expenses, including travel, lodging, and equipment. Without proper tracking, it’s easy to miss valuable deductions and fail to understand your true earnings.

Why It Matters:

• Helps you understand your financial health.

• Aids accurate tax filings.

• Prevents missed deductions and minimizes audit risks.

Action Step:

Invest in accounting software like QuickBooks, tailored for small business owners, or hire a professional bookkeeper. Additionally, consider maintaining separate bank accounts for personal and business finances to streamline the bookkeeping process.

2. Regularly Update Tax Projections

Tax liabilities can fluctuate based on race winnings, sponsorship income, and other variables. Regularly updating tax projections ensures you’re prepared for estimated tax payments, prevents unexpected liabilities, and allows for better financial planning.

Why It Matters:

• Helps avoid penalties for underpayment of estimated taxes.

• Enables smarter business and financial decisions.

• Helps forecast cash flow for business and personal goals.

Action Step:

Schedule quarterly meetings with your tax advisor to analyze income changes and adjust estimated payments. Use these projections to determine optimal times for major purchases, contributions to retirement accounts, or other financial moves.

3. Consider Converting to an S Corporation

Operating as a sole proprietor may result in higher self-employment taxes. Converting to an S Corporation can reduce these taxes by enabling you to pay yourself a reasonable salary while taking the remaining income as business distributions, which are not subject to FICA taxes.

Why It Matters:

• Saves on self-employment taxes (Social Security and Medicare).

• Provides a more tax-efficient way to structure income.

Action Step:

Consult with a tax professional to assess whether S Corporation status is beneficial for your business. They will also guide you through the process and ensure compliance with IRS guidelines regarding reasonable compensation.

4. Create a Solo 401(k)

A solo 401(k) is an excellent retirement savings vehicle for self-employed individuals like jockeys. It allows higher contribution limits compared to traditional IRAs, enabling significant tax-deferred savings.

Contribution Limits for 2025:

• Employee Contribution: Up to $23,500 ($30,000 if age 50+).

• Employer Contribution: Up to 25% of net earnings, with a combined limit of $70,000.

Establishment Deadline:

• The plan must be established by December 31, 2025, but contributions can be made up until your tax filing deadline, including extensions.

Action Step:

Speak with your financial planner to establish a solo 401(k) and determine the appropriate contribution levels based on your earnings.

5. Make Roth IRA Contributions if Eligible

Roth IRAs offer tax-free growth and withdrawals in retirement, making them a valuable tool for jockeys who qualify under income limits. Additionally, contributions for 2024 can still be made until April 2025, providing extra flexibility.

Key Details:

• Income Limits for 2025: Single filers earning up to $150,000 can make full contributions, with a phase-out of up to $165,000. For married filers, the phase-out range is $236,000 to $246,000.

• 2024 Contribution Deadline: April 15, 2025.

Action Step:

Determine your eligibility and contribute the maximum amount to a Roth IRA if possible. If you exceed the income limits, consider a backdoor Roth IRA contribution by funding a traditional IRA and executing a Roth conversion.

6. Tax Loss Harvesting in Brokerage Accounts

If you hold investments in taxable brokerage accounts, tax-loss harvesting can help you reduce your tax bill. This strategy involves selling underperforming investments to offset realized capital gains or up to $3,000 of ordinary income annually. Unused losses can be carried forward to future tax years.

Why It Matters:

• Lowers your current tax liability.

• Improves the after-tax performance of your investment portfolio.

Action Step:

Work with your financial advisor to review your portfolio before year-end. Identify opportunities to sell underperforming assets strategically while maintaining a balanced investment strategy.

7. Tax Gain Harvesting in the 0% Long-Term Capital Gains Bracket

If your income is low enough to qualify for the 0% capital gains tax bracket, you can sell appreciated assets without incurring taxes on the gains. For 2025, this bracket applies to single filers with taxable income up to $48,350 ($96,700 for married filing jointly).

Why It Matters:

• Realizes gains tax-free at the federal level.

• Resets the cost basis, reducing future tax liabilities.

Action Step:

Monitor your income levels and consult with your tax advisor to determine if you qualify for tax gain harvesting. This strategy can be especially beneficial in years with lower-than-usual earnings.

Final Thoughts

For horse racing jockeys, proactive tax planning is an essential part of financial success. Implementing these strategies in 2025 will not only help you minimize your tax burden but also position you for long-term financial growth. From creating a robust bookkeeping system to leveraging advanced tax strategies like S Corporations and tax gain harvesting, the right moves can make a significant difference.

As a financial planner who focuses on working with jockeys, I’m here to help you navigate these complex decisions. Let’s create a customized tax and financial strategy that fits your unique needs. Contact me today to get started on securing your financial future.

529 Education Savings Accounts: What Jockeys Should Know About Planning for the Future

For horseracing jockeys, education savings might not seem like a top priority—especially in the earlier stages of your career when your focus is on building your reputation and achieving success on the track. However, as your career grows, so do your opportunities to plan for the future, including the education of your children or other loved ones.

529 education savings accounts are a flexible, tax-advantaged way to prepare for future educational costs. Even if you’re not yet thinking about college or trade school, understanding how these accounts work can help you make smart financial decisions down the road. Let’s address some common questions and concerns about 529 plans, especially for jockeys who often face unique financial and career challenges.

1. What if my child gets a scholarship?

As a jockey, you know the value of hard work and dedication—and your child might achieve their own success in the form of a scholarship. If this happens, the money you’ve saved in a 529 account won’t go to waste. You can withdraw an amount equal to the scholarship without facing the usual 10% penalty for non-qualified expenses. You’ll only owe income taxes on the earnings portion of the withdrawal.

Alternatively, you can keep the money in the account for future use, such as graduate school or other educational needs. This ensures that the funds you’ve set aside continue to work for your family.

2. What if they don’t go to college at 18?

Many jockeys know that life doesn’t always follow a traditional timeline. If your child isn’t ready for college right after high school, there’s no need to worry. 529 accounts don’t have an expiration date, so the money can stay in the account until it’s needed. This flexibility gives your family time to figure out the right path, whether it’s a gap year, pursuing a professional career, or even joining the horseracing industry themselves.

3. What if they never go to college?

The question of “what if they never go to college” comes up often, especially for jockeys whose children might consider following in their parent’s footsteps within the horseracing world. While 529 plans are primarily designed for higher education, they can also be used for other qualifying educational opportunities, such as vocational or trade schools, apprenticeships, and eligible certificate programs.

If none of these options apply, you can change the account’s beneficiary to another family member, such as a sibling or even yourself if you want to pursue your own education or certifications later in life. If no one ends up using the funds for education, you can withdraw the money for other purposes, although earnings will be subject to income tax and a 10% penalty.

4. What if there’s money left over?

In some cases, families save more than what’s needed for education. If this happens, the leftover funds can remain in the account for future educational needs, such as graduate school. Starting in 2024, the IRS allows certain unused 529 funds to be rolled into a Roth IRA for the beneficiary, provided the account has been open for at least 15 years and other conditions are met. This creates an opportunity to repurpose the savings for retirement.

5. What if one child doesn’t need the money, but another does?

For jockeys with multiple children, this is a common question. Fortunately, 529 accounts allow for easy beneficiary changes among qualifying family members. If one child doesn’t use the funds, you can transfer the account to a sibling, cousin, or even a grandchild. This flexibility ensures the money you’ve saved continues to benefit your family.

6. What if my child pursues a career instead of education?

If your child decides to follow in your footsteps in the horseracing industry or pursue another professional career that doesn’t require a college education, the 529 funds can still be used in creative ways. For example, some vocational training programs may qualify as eligible expenses. If not, you could withdraw the funds for other purposes, with the understanding that taxes and penalties will apply to earnings.

7. Why should I think about this now?

Early in your career as a jockey, your focus might be on managing race schedules, securing mounts, and building financial stability. But as your career advances and your financial position strengthens, it’s important to think about long-term planning. A 529 account is a great way to ensure that your children enter adult life better off than you were—whether it involves college, trade school, or other educational paths.

Planning for Success Off the Track

As a jockey, you know the value of preparation and strategy. Just as you plan your races, planning your finances is crucial for long-term success. A 529 education savings account is one tool that can help you build a legacy for your family, no matter what paths they choose.

Whether you’re just starting your career or riding at the peak of your success, it’s never too early—or too late—to explore your financial options. If you have questions about 529 plans or other strategies to secure your family’s future, I’m here to help. Let’s work together to create a plan that works for you, both on and off the track.

5 Things I Wish Jockeys Knew About Money

As a financial advisor who works with horseracing jockeys, I’ve seen the unique challenges you face both on and off the track. Your career demands incredible skill, discipline, and sacrifice, but it also comes with financial and physical risks. Here are five essential lessons to help you take control of your financial future:

1. It’s Not a Forever Career

Jockeying is a short-lived profession for most. The physical demands, weight requirements, and injuries mean that few can maintain a long career in the saddle. This makes financial planning critical. While you may be earning well today, you need to treat those earnings as a limited resource. Build savings, invest wisely, and prepare for the day when you’ll need to transition to a life outside of racing.

2. You’re in a Race Against Time

Your career doesn’t just end early—it’s grueling while it lasts. Long hours, constant travel, and the ever-present risk of injury mean you need to start putting money away immediately. Compounding works in your favor the sooner you begin. Think of every dollar saved as a seed that can grow into a larger financial safety net for your future. Don’t wait until your best earning years are behind you to start thinking about retirement.

3. Injuries Are a Question of When, Not If

As a jockey, injuries aren’t hypothetical—they’re inevitable. That’s why you need a plan in place before an accident sidelines you.

• Savings: An emergency fund can help cover expenses when you’re unable to ride.

• Disability Insurance: This is a must-have. It provides income when you’re unable to work.

• Support System: Identify people who can help care for you during recovery and ensure your financial obligations are met.

Planning for these scenarios isn’t pessimistic—it’s realistic and smart.

4. Investing: Your Dollar Army

Think of investing as sending out an army of dollars to work for you. Each dollar has the potential to go out, earn more dollars, and return stronger. This isn’t about chasing quick gains or risky ventures; it’s about creating a disciplined, long-term plan. A diversified portfolio can help you grow wealth steadily over time, giving you the financial freedom to step away from racing when the time comes.

5. Minimizing Taxes Isn’t Always the Best Move

Many jockeys focus on minimizing taxes today, but this can lead to missed opportunities for long-term growth. For instance, maximizing contributions to tax-advantaged retirement accounts might reduce your tax bill slightly now but can result in additional taxes in retirement. Additionally, if you look to make a career transition or major purchases well before typical retirement ages, you may face stiff taxes and penalties to access your money. Lastly, tax-deductible business purchases can reduce taxes but they only make sense if the purchase is necessary for your business. Work with a financial advisor to strike the right balance between short-term tax strategies and long-term wealth-building goals.

Bonus Tip: Plan for Your Money Before You Earn It

Without a clear plan for your earnings, it’s easy to fall into financial traps. The thrill of a big payday might tempt you to splurge on unnecessary things like flashy cars, luxury items, or extravagant trips. You might also forget to set aside money for taxes, leading to a nasty surprise when the bill comes due. And without a strategy, windfalls can vanish before you’ve invested them to secure your future. Budgeting isn’t just about controlling spending—it’s about giving every dollar a purpose. By planning ahead, you can avoid common pitfalls and make sure your earnings set the foundation for lasting financial security.

Take the First Step Toward Financial Success

You don’t have to figure all of this out on your own. Managing your finances as a jockey is challenging, but with the right guidance, you can create a plan that works for you now and in the future. I help jockeys navigate these financial complexities—whether it’s saving for the long term, reducing taxes appropriately, planning for injuries, or investing to grow your wealth. Let’s work together to ensure your hard-earned money works as hard as you do.

Contact me today to start building your personalized financial game plan. Your career may have a finish line, but your financial success doesn’t have to.

Understanding Depreciation Recapture: What Every Horseman and Jockey Should Know

Depreciation is a cornerstone of tax planning for horsemen and small business owners who own assets such as broodmares, tractors, and rental properties. While depreciation provides immediate tax benefits, it also brings long-term tax consequences when selling an asset. Specifically, depreciation recapture can impact your net proceeds and overall tax liability. This article will walk you through the concept of depreciation, its role in the tax code, and how recapture works when selling assets commonly held by horsemen and small business owners.

What is Depreciation?

Depreciation is a tax concept that allows businesses and individuals to recover the cost of a tangible asset over its useful life. The IRS recognizes that assets used in a trade or business wear out, become obsolete, or lose value over time. Depreciation allocates this loss of value across several years, reducing taxable income annually.

Why Depreciation Exists in the Tax Code

The purpose of depreciation is to encourage investment in business assets by providing tax relief for their gradual wear and tear. For example, a horseman who purchases a new trailer or upgrades farm equipment can deduct part of the cost each year, helping offset the expense. Without depreciation, the full cost of the asset would have to be recovered only at the time of sale, creating a significant financial burden.

Depreciation is Not Optional

Once an asset is placed in service for business use, depreciation is mandatory. The IRS requires you to claim depreciation, and it assumes you’ve done so whether or not you include it on your tax return. This is important because depreciation recapture applies to any allowable depreciation, even if you choose not to claim it.

Depreciation and Your Adjusted Cost Basis

The adjusted cost basis of an asset is its original purchase price, adjusted for depreciation and other factors. Depreciation reduces your basis, which in turn increases your taxable gain when you sell the asset.

Depreciation Recapture: The Basics

When you sell an asset for more than its adjusted basis, the IRS requires you to "recapture" the depreciation deductions you claimed (or could have claimed) in previous years. Depreciation recapture treats this portion of your gain as ordinary income or subjects it to specific tax rates, depending on the type of asset.

Tax Rates Applicable to Depreciation Recapture

The tax rates for depreciation recapture depend on the type of asset:

• Real Property (e.g., rental property): Recapture is taxed as ordinary income with a maximum rate capped at 25%.

• Personal Property (e.g., tractors, trucks, broodmares): Recapture is taxed at your ordinary income tax rate, which, for federal income taxes) can be as high as 37% (2024).

Detailed Example: Depreciation Recapture for a Broodmare

Broodmares used in a horse breeding business are typically classified as 7-year property under the Modified Accelerated Cost Recovery System (MACRS). The 200% declining balance method is used for depreciation. Depreciation tables can be found in Appendix A of IRS Publication 946.  Here’s how depreciation recapture would apply in a real-world scenario for a broodmare.

Purchase:

You purchase a broodmare for $100,000 in Year 1 and place her in service for your breeding operation.

Depreciation Schedule:

Under MACRS, the broodmare is depreciated over 7 years using the 200% declining balance method. This method allows higher depreciation in the earlier years. The IRS provides standard depreciation percentages for 7-year property, as shown below:

Depreciation Claimed:

If the broodmare is used for 5 years, the total depreciation claimed is:

• Year 1: $14,290

• Year 2: $24,490

• Year 3: $17,490

• Year 4: $12,490

• Year 5: $8,930

• Total Depreciation Claimed (5 years): $77,690

Adjusted Basis:

The adjusted cost basis is the original cost minus the depreciation claimed:

• Original Cost: $100,000

• Less Depreciation Claimed: $77,690

• Adjusted Basis: $22,310

Sale

At the end of year 5, you sell the broodmare for $80,000.

Taxable Gain:

Your taxable gain is the difference between the sale price and the adjusted basis:

• Sale Price: $80,000

• Adjusted Basis: $22,310

• Taxable Gain: $57,690

Depreciation Recapture

The IRS requires you to "recapture" depreciation up to the total depreciation claimed ($77,690 or the amount of the gain, whichever is lower). This portion of the gain is taxed at ordinary income tax rates, while any additional gain is taxed at the lower capital gains rate.

• Depreciation Recaptured: $57,690 (equal to the taxable gain).

• Tax Rate on Recapture: Depreciation recapture for personal property (like a broodmare) is taxed at ordinary income tax rates, up to 37%.

Tax Calculation

Assume your ordinary income tax rate is 32%. Since the entire gain is due to depreciation recapture, the entire $57,690 is taxed as ordinary income.

• Depreciation Recapture Tax: $57,690 x 32% = $18,460.80

Net Proceeds After Tax

Your sale proceeds after taxes are calculated as:

• Sale Price: $80,000

• Less Taxes Owed: $18,460.80

• Net Proceeds: $61,539.20

Modified Example: Depreciation Recapture for a Broodmare Sold Above the Original Purchase Price

Let’s consider a scenario where a broodmare is sold for more than the original purchase price, $120,000 in this case, highlighting the impact of both depreciation recapture and capital gains tax. This situation demonstrates how gains are taxed differently based on depreciation and appreciation.

Taxable Gain:

Your total taxable gain is calculated as:

• Sale Price: $120,000

• Adjusted Basis: $22,310

• Taxable Gain: $97,690

Depreciation Recapture and Capital Gain

The IRS separates the taxable gain into two parts:

1. Depreciation Recapture: The portion of the gain attributable to depreciation is recaptured and taxed at your ordinary income tax rate.

2. Capital Gain: Any gain exceeding the original purchase price ($20,000 in this case) is taxed at long-term capital gains rates if the property was held for more than one full year. Note: Broodmares must be held for 2 years to qualify as a long-term capital gain.

Tax Breakdown:

• Depreciation Recaptured: $77,690 (the total depreciation claimed, limited to the gain attributable to depreciation).

• Capital Gain: $120,000 - $100,000 = $20,000 (the amount above the original purchase price).

Tax Calculation

Assumptions:

• Ordinary Income Tax Rate: 32% (applied to depreciation recapture).

• Long-Term Capital Gains Rate: 15% (applied to the portion above the original purchase price).

1. Depreciation Recapture Tax:

• $77,690 x 32% = $24,860.80

2. Capital Gains Tax:

• $20,000 x 15% = $3,000

Total Taxes Owed:

• Depreciation Recapture Tax: $24,860.80

• Capital Gains Tax: $3,000

• Total Tax Liability: $27,860.80

Net Proceeds After Tax

Your sale proceeds after taxes are calculated as:

• Sale Price: $120,000

• Less Taxes Owed: $27,860.80

• Net Proceeds: $92,139.20

Note: The two scenarios presented here are for illustrative purposes and should not be used as a basis for actual calculations of depreciation. They ignore specific changes to deprecation calculations in the year of purchase or sale such as the Half-year or Mid-quarter conventions. Additionally, certain property may be eligible for Bonus or Section 179 depreciation, which are outside the scope of this article. Finally, they account for Federal Taxes only and exclude state and local income taxes.

Types of Depreciation Recapture That May Surprise People

Now that we’ve reviewed depreciation recapture in two similar scenarios, here is a short list of types of depreciation recapture that often surprise people.

1. Home Office Depreciation:
   Even if you sell your primary residence and qualify for the capital gains exclusion, depreciation claimed for a home office must be recaptured and taxed as ordinary income.

2. Equipment Sold for Less than Purchase Price:
   Even if you sell equipment like a tractor or truck for less than its original cost, you may still owe recapture tax on depreciation claimed if the sale price exceeds the adjusted basis.

3. Rental Property:
   Depreciation recapture on rental properties is recaptured at a federal tax rate of up to 25%, even if the property is sold at a loss overall compared to its original purchase price.

4. Partially Business-Used Assets:
   Depreciation claimed on assets used partially for personal purposes (e.g., a car or horse trailer) must be recaptured for the business-use portion upon sale.

5. Assets Given as Gifts:
   If you gift a depreciated asset, the recipient inherits both the basis and the depreciation history, potentially triggering recapture when they sell the asset.

6. Early Sale of Assets:
   Selling an asset before the end of its useful life doesn’t eliminate recapture liability; you still owe tax on depreciation claimed up to the sale date.

Final Thoughts

Depreciation is a valuable tool for horsemen and small business owners to reduce taxable income and allow them to reduce cash lost to taxes when reinvesting in their business, but it comes with long-term implications. Depreciation recapture can significantly impact your tax liability when you sell an asset and often catches people by surprise. By understanding the rules and planning ahead, you can maximize the benefits of depreciation while minimizing surprises at tax time. Always consult with a tax professional to navigate these complex rules and create a strategy tailored to your situation.

If you need help understanding the impacts of depreciation recapture on your business, contact me at Derek@trophypointfp.com

Additional Sources:

IRS Publication 946: How to Depreciate Property

IRS Publication 544: Sales and Other Dispositions of Assets

Dean Dorton: Federal Equine Depreciation Summary

5 Common Tax Mistakes Jockeys and Small Business Owners Should Avoid

Managing taxes can be an overwhelming task, particularly for jockeys and small business owners who must balance operating their business with being the primary employee. It's tempting to delay or overlook the tax responsibilities, but this can lead to problems down the line. Through my experience with numerous small business clients, I have identified the most common tax mistakes they make.

1. The Importance of Separating Personal and Business Expenses

Mixing personal and business expenses is a prevalent mistake that can lead to a tangled financial web and unwanted attention from the IRS. Picture this: using one bank account for groceries, hay and feed, and business travel can obscure your financial story. To prevent this, maintain separate accounts for personal and business transactions. This distinction not only ensures cleaner records but also simplifies tax reporting, deduction claims, and is one of the factors that the IRS uses to determine if your business is actually for profit.

2. Effective Profit and Loss Tracking and Bookkeeping

Accurate bookkeeping and profit and loss tracking are the backbone of a financially sound business. Neglecting these can result in missed deductions and leave you in the blind regarding the status of your business. Implementing reliable accounting software such as QuickBooks or Xero, which can automate processes and provide real-time financial insights. Hiring a professional accountant can further enhance accuracy, offering expert advice tailored to your specific needs. Detailed record-keeping empowers you to make informed financial and tax decisions instead of guesses.

3. Understanding and Paying Estimated Taxes

For small business owners and independent contractors like jockeys, understanding the obligation to pay estimated taxes quarterly is crucial. Missing these payments can lead to penalties and interest charges. Additionally, not setting aside money for taxes often puts people in a position where they owe the money but have already spent it on something else. Proactively developing tax estimates is a necessity and should be updated throughout the year, especially if income is highly variable. Set aside a portion of your income regularly to cover these payments. Being proactive in managing estimated taxes helps avoid cash flow disruptions and ensures smoother financial management.

4. Clarification on Tax Filing Extensions vs. Payment Deadlines

A common misconception is that a tax filing extension also extends the payment deadline. However, this is not the case. While an extension gives you additional time to file your return, any taxes owed are due by the original deadline. Failing to pay on time can result in late fees and interest. To prevent this, estimate your tax liability accurately and pay by the standard due date, even if you plan to file for an extension. Understanding this distinction helps in avoiding unnecessary financial penalties.

5. How 'Write-Offs' Really Work

Many business owners are under the impression that write-offs reduce taxes dollar for dollar. I've seen many people make an unnecessary purchase and justify it by stating "It's a tax write-off." In reality, they reduce your taxable income. For example, if you have $2,000 in deductible expenses and are in the 25% tax bracket, your tax savings would be $500. Common deductions include business travel, equipment, feed, hay, etc. Understanding how these deductions impact your taxable income can help you plan more effectively and maximize your financial strategy.

While tax deductions can significantly lower your taxable income, it's crucial to discern between necessary and unnecessary expenses. The primary consideration for any deductible purchase should be its relevance and necessity to your business operations. Just because a purchase is tax-deductible does not inherently justify expenditure; it should serve a functional purpose that supports or your business. Unnecessary purchases justified solely by their deductibility are not prudent financial decisions and can strain your cash flow without providing real value.  A great example would be buying a brand new vehicle when a functionally equivalent used vehicle is available. This strategic approach ensures that your deductions genuinely contribute to the health and growth of your business, rather than misleadingly reducing short-term tax obligations at the cost of long-term fiscal responsibility.

Conclusion

Avoiding these common tax mistakes requires diligence and a proactive approach to financial management. By separating personal and business finances, keeping accurate records, paying estimated taxes, understanding extension limitations, and correctly interpreting write-offs, jockeys and small business owners can navigate tax season with confidence. Empower yourself with the right tools and advice to ensure your financial journey is as smooth as your ride to success. With careful planning and expert guidance, you can turn these insights into a robust foundation for your financial future.

If you or someone you know needs help getting their business finances organized, please reach out to me at Derek@trophypointfp.com.

Debunking the Myth of Mortgage Interest Deduction for Jockeys and Small Business Owners

Introduction

When considering a home purchase, jockeys and small business owners often hear a compelling argument about the benefits of the mortgage interest deduction. It's a common refrain, "You can save on taxes!" But is this really the financial boon it’s touted to be? In this blog post, I’ll dissect the mortgage interest deduction, explore who can actually benefit from it, and uncover why you might not want to fall for the hype. By the end, you’ll have a clearer understanding of how this deduction works and whether it truly makes sense for your financial situation.

The Allure of Tax Savings

Who doesn’t want to save on taxes? The idea of reducing your tax bill by deducting mortgage interest is undeniably attractive. For many, it seems like a no-brainer to take advantage of these potential savings. However, it's essential to understand the specifics before making any decisions.

In theory, the mortgage interest deduction allows homeowners to deduct the interest paid on their mortgage from their taxable income. This can significantly reduce the amount of taxes owed. But the reality is more nuanced, and not everyone stands to benefit equally.

The Basics of Mortgage Interest Deduction

Before we dive deeper, let's clarify what mortgage interest deduction entails. Essentially, it's a tax incentive designed to encourage homeownership. Homeowners can deduct the interest they pay on their mortgage, potentially lowering their taxable income and thus reducing their overall tax liability.

However, this deduction only applies if you itemize your deductions on your tax return. Itemizing involves listing all eligible deductions individually, as opposed to taking the standard deduction—a flat amount that reduces your taxable income.

The Requirement to Itemize Deductions

The catch with the mortgage interest deduction is that it only benefits those who itemize their tax deductions. This requirement significantly limits who can take advantage of it. For many taxpayers, the standard deduction is more advantageous and straightforward.

By choosing the standard deduction, taxpayers forego itemizing their deductions. This means they can't claim the mortgage interest deduction, among other itemizable expenses, such as medical expenses and charitable contributions.

The Importance of Understanding Tax Implications

The advice from a real estate agent, friend, or family about tax savings could be incorrect, and you might only realize this when filing your tax return.  Taxation is complex, influenced by factors like individual income, the standard deduction, and specific deductions for which you may qualify. Relying solely on anecdotal advice or sly comments meant to influence your decision may lead to false expectations and financial errors. Consulting a tax professional or researching thoroughly is crucial to accurately assess the benefits of the mortgage interest deduction before filing.

The Impact of the TCJA on Itemization

The Tax Cuts and Jobs Act (TCJA) of 2017 had a profound impact on itemized deductions. One of the most significant changes was the substantial increase in the standard deduction. For 2024, the standard deduction is $14,600 for single filers and $29,200 for married couples filing jointly.

This increase means that far fewer taxpayers benefit from itemizing their deductions. With the higher standard deduction, the threshold for itemizing is much higher. Consequently, fewer people are able to claim the mortgage interest deduction, as the standard deduction often provides greater tax savings.

You can find up-to-date standard deduction information on the IRS website here.

Why Fewer People Are Itemizing

The TCJA's changes led to a dramatic drop in the number of taxpayers who itemize their deductions. According to the Tax Policy Center, the percentage of taxpayers who itemized fell from 30% in 2017 to just under 10% in 2020. This shift highlights the reduced relevance of the mortgage interest deduction for most people.

For jockeys and small business owners, this trend is particularly important to consider. Even if you're paying significant mortgage interest, you may find that the standard deduction offers a better financial outcome than itemizing.

The Potential Expiration of the TCJA

One crucial aspect to keep in mind is that the TCJA is set to expire at the end of 2025. If Congress does not extend or make these provisions permanent, the tax landscape will change once again. The standard deduction could revert to previous levels, potentially making itemization more attractive.

If the TCJA expires, more taxpayers may find it beneficial to itemize their deductions, including the mortgage interest deduction. However, this is speculative, and it's essential to stay informed about potential tax law changes.

What This Means for Homebuyers

For prospective homebuyers, it's vital to approach the mortgage interest deduction with a clear understanding of its limitations and potential changes. While it can be a valuable tax benefit, it shouldn't be the sole reason for purchasing a home. Many other factors, such as your financial goals, housing market conditions, and personal circumstances, should also play a role in your decision.

Alternatives to Consider

Instead of relying solely on the mortgage interest deduction, consider other ways to maximize your financial well-being. For example, focus on building equity in your home, investing in diverse assets, and managing your overall tax strategy.

Working with a financial advisor or tax professional can provide valuable insights tailored to your specific situation. They can help you develop a comprehensive plan that aligns with your financial goals, ensuring you're making informed decisions.

Conclusion

The mortgage interest deduction is often hailed as a significant tax benefit for homeowners. However, the reality is more complex, and many taxpayers, including jockeys and small business owners, may find that the standard deduction offers greater advantages.

Understanding the nuances of this deduction, the impact of the TCJA, and potential future changes is crucial for making informed financial decisions. Rather than falling for the myth of the mortgage interest deduction, take a holistic approach to your finances, considering all available strategies to maximize your financial well-being.

For personalized guidance and tailored solutions, consider consulting with a financial advisor. They can help you navigate the complexities of tax deductions and develop a strategy that aligns with your unique circumstances.

In the end, the goal is to make sound financial decisions that support your long-term goals, rather than being swayed by common misconceptions. By staying informed and proactive, you can achieve greater financial stability and success.