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Stop PAYING taxes and start PLAYING Taxes – How To Keep Money On Your Side Of The Court

Writer's picture: Greg ClementGreg Clement

Taxes, a subject that often makes people cringe. I get it—nobody likes thinking about taxes, but the sooner you deal with them head on the better off you’ll be. 


Taxes are the single greatest destroyer of wealth. If you don’t understand how to minimize them legally, you’re leaving money on the table—money that could fund your dreams, your family’s future, or your next big adventure.


Think about this: if you were coaching a basketball team, would you go out onto the court with only three players when you’re allowed five? Of course not! Yet that’s exactly what most people are doing with their taxes—they’re not using all the tools available in the IRS

Playbook. 


Let’s fix that.


The IRS Tax Code: A Playbook for Entrepreneurs and Investors

Here’s something that’ll blow your mind: about 90% of the IRS tax code isn’t about taking your money—it’s about showing you how to keep more of it. Yes, you read that right. The tax code is essentially a strategy manual for building wealth if you know how to use it.


The ultimate hack? Stop looking at taxes as a burden and start seeing them as a game.

If you know the rules and play strategically, you can turn taxes into one of your greatest allies.

taxes
taxes

Play 1: Start a Side Hustle or Small Business

Starting a business, even as a side hustle, is one of the most powerful tax strategies out there. Why? Because businesses get to deduct their expenses before paying taxes.


For example, as a business owner, you can legally deduct:

  • Home office expenses (a portion of your rent or mortgage, utilities, and even internet).

  • Miles driven for business (currently about 65.5 cents per mile).

  • A percentage of your phone bill.

  • Meals and networking costs (if you’re meeting someone for a business purpose).


This means that, unlike an employee, you’re taxed on your net income—what’s left after your expenses. For someone earning $50,000 to $100,000 per year, this simple shift could end up saving you thousands annually.


Play 2: Shift to an S-Corp for Bigger Savings

If your side hustle or business is generating $60,000 or more, consider structuring it as an S-Corp. Why? It allows you to split your income into two parts:

  1. A reasonable salary (which is subject to payroll taxes).

  2. Profit distributions (which are not).


Let’s break it down:Imagine you’re earning $100,000 through your S-Corp. You pay yourself a $50,000 salary, and the other $50,000 is taken as a profit distribution. That $50,000 avoids the 15.3% payroll tax, saving you $7,650. Multiply that over several years, and you’re keeping tens of thousands of dollars in your pocket—all legally.


Play 3: Invest in Real Estate

Real estate isn’t just about passive income or appreciation; it’s a tax-saving powerhouse.


One of the biggest benefits being depreciation.


The IRS lets you write off the wear and tear on your property—even if it’s actually increasing in value! This depreciation can offset your rental income, making it a win-win.


Want to supercharge this? Use component depreciation or bonus depreciation to accelerate those savings. For example, if you buy a property for $1 million, a cost segregation study could allow you to deduct $200,000 or more in the first year. That’s $200,000 you don’t pay taxes on, which can be reinvested or used to build your portfolio faster.


Real estate also offers some serious benefits for high-income earners. If you or your spouse qualify as a real estate professional, the IRS removes limits on how much depreciation you can use to offset your taxable income. This can potentially save you loads of cash. 


Play 4: Max Out Retirement Contributions

Retirement accounts are another underutilized tool in the wealth-building Playbook. Two of my favorites are the Roth IRA and Health Savings Account (HSA):

  • Roth IRA: Contributions are made with after-tax dollars, but your investments grow tax-free, and withdrawals in retirement are also tax-free. Over decades, this can compound into millions without a penny going to Uncle Sam.

  • HSA: This is the unicorn of accounts—pre-tax contributions, tax-free growth, and tax-free withdrawals for qualified medical expenses. If you have a high-deductible health plan, open an HSA immediately. You can even use it for expenses like eyeglasses, physical therapy, and certain doctor-prescribed health aids.


Play 5: Use Self-Directed IRAs to Invest Outside the Box

Most people think their IRA or 401(k) can only be invested in stocks or mutual funds, but that’s a myth. With a self-directed IRA, you can invest in real estate, startups, private loans, or even livestock!


Here’s an example: Peter Thiel, one of PayPal’s founders, used his Roth IRA to buy early shares of the company. Fast forward, and that Roth IRA grew to over $5 billion—all tax-free.

I know that’s a far fetched example but I’m telling you, there’s a million other testimonials out there. Anyone can do this!


This strategy isn’t just for billionaires. 


Imagine using your IRA to invest in a rental property or lend money at a high interest rate. The returns could be exponential, and all the growth stays within the tax-free walls of the account.


Why Winning The Game Matters:

Here’s the bottom line: the more money you keep, the more freedom you have. Freedom to invest, freedom to pursue your passions, and freedom to live the life you’ve always dreamed of.


Taxes don’t have to be this dirty concept you avoid. They’re just part of the game. And once you learn the rules, you can start playing to win.


So, stop paying and start playing taxes. Here’s my challenge for you: Be curious. Ask questions. Learn from experts. Start layering these strategies into your financial plan, and watch how it transforms your life.


Remember, the IRS has given you the Playbook—you just need to use it. Put all five players on the court and take control of your financial future.


To hear more from us check out our financial challenges inside the Freedomology app! Join our next F40 Sprint to learn everything you need to know to reach financial freedom at www.freedomology.com/f40.

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