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How the Wealthy Avoid Taxes and What the Tax Code Is Really Rewarding

January 16, 20267 min read

If you are a high earning professional, taxes probably feel like your biggest financial frustration.

You work long hours.

You earn a strong income.

And every year, a significant portion of that income disappears before it ever reaches your bank account.

After speaking with hundreds of high earning professionals, one concern comes up again and again.

Why does it feel like employees pay the most taxes, while businesses and investors seem to pay far less?

The numbers support that frustration.

The top ten percent of earners pay the majority of total taxes collected in the United States. Meanwhile, businesses and investors receive significant tax deductions and incentives.

At first glance, it can feel unfair.

But here is the truth that changes everything.

The tax code is not broken.

It is designed.

And once you understand what it rewards, you begin to see taxes very differently.


Why the Tax Code Looks Unfair but Is Actually Intentional

The government has one primary goal when it comes to taxation.

Economic growth.

That growth comes from people and entities willing to take risks, invest capital, create jobs, build housing, develop infrastructure, and expand industries like energy and technology.

The tax code is written to encourage those activities.

Employees provide stability to the system, but investors and business owners fuel expansion. Because of that, the tax code rewards behavior that involves risk and long term economic contribution.

This is why understanding taxes is not about finding loopholes or tricks.

It is about understanding incentives.

Once you understand the incentives, you can begin making decisions that align with them.


Principle One: The Tax Code Rewards Risk

The first principle behind most tax advantages is risk.

When you invest capital into a business or asset, you are taking on uncertainty. That uncertainty could come from market conditions, operational challenges, regulatory changes, or economic cycles.

The government wants individuals and entities to take those risks because they stimulate economic activity.

Real estate is one of the clearest examples of this.

Although real estate is often described as stable, it involves multiple layers of risk.

There is asset level risk. A specific property may have issues related to location, condition, or local demand.

There is market risk. Population shifts, job growth, and local economic health all influence rental demand and pricing. A single large employer leaving a city can change an entire housing market.

There is tenant risk. Vacancies, late payments, and nonpayment still require you to cover expenses like insurance, taxes, and debt service.

There is interest rate risk. Leverage can amplify returns, but rising rates or declining values can quickly change the economics of a deal.

There is liquidity risk. Unlike stocks, real estate cannot be sold instantly. Selling takes time and involves transaction costs.

There is operational risk. Poor property management, rising maintenance costs, or contractor issues can all impact returns.

With this many risks, it is reasonable to ask why anyone would invest in real estate at all.

The answer lies in incentives.

The government offsets these risks by offering tax benefits that reduce the financial burden of ownership.

That brings us to the second principle.


Principle Two: Reduce Taxes by Reducing Taxable Income

Business owners and investors are taxed very differently from employees.

Employees are taxed on gross income before expenses.

Business owners and investors are taxed on profit, which is revenue minus expenses.

The more legitimate expenses you have, the lower your taxable income.

In a business setting, deductible expenses can include equipment, software, marketing, education, professional fees, and operational costs that are ordinary and necessary.

In real estate, deductions may include mortgage interest, property taxes, insurance, repairs, maintenance, property management fees, utilities, legal fees, advertising, and travel related to the investment.

In some situations, certain investors may also qualify for the Qualified Business Income deduction, which can reduce taxable income further depending on income and structure.

In addition, real estate investors may generate passive losses that can sometimes offset other income, depending on income levels and participation. If losses cannot be used immediately, they are typically carried forward to future years.

Up to this point, these deductions represent real money spent.

But real estate introduces something even more powerful.


The Most Powerful Deduction Is One You Do Not Pay in Cash

Depreciation is one of the most misunderstood aspects of the tax code.

Depreciation allows investors to deduct the assumed wear and tear of a property over time, even though the property itself may be increasing in value.

On paper, the IRS treats buildings and certain components as assets that decline in value each year.

This creates a non cash deduction.

That means an investor can have positive cash flow while showing little or no taxable income from that property.

This is a core reason real estate can be so tax efficient.

However, it is important to understand that depreciation is generally a deferral, not a permanent elimination of taxes. When a property is sold, depreciation is typically recaptured and capital gains tax may apply.

Which leads to the third principle.


Principle Three: Defer Capital Gains and Let Compounding Work

Tax deferral is not just about paying less tax this year.

It is about keeping more capital invested and compounding over time.

Money that is not paid in taxes continues working inside the investment. Over years or decades, that difference can compound into significant wealth.

Real estate investors often use several strategies to defer capital gains.

One common approach is a 1031 exchange, which allows the proceeds from a sale to be reinvested into another qualifying property without triggering immediate taxes.

Another approach is refinancing instead of selling. By borrowing against increased property value, investors can access capital without triggering a taxable event, since loan proceeds are not considered income.

Some investors use structures like Delaware Statutory Trusts or Qualified Opportunity Funds to defer or potentially reduce capital gains, depending on holding period and structure.

Others use tax deferred accounts like self directed IRAs or HSAs, understanding that these come with restrictions similar to other retirement accounts.

Each of these approaches carries risk and complexity and should always be evaluated with qualified professionals.


The Final Step: Long Term Planning and Legacy

There is one additional concept that explains how wealth often stays within families across generations.

Many assets receive a step up in basis at death.

This means heirs inherit assets at their current market value rather than the original purchase price. In many cases, this eliminates accumulated capital gains and depreciation recapture.

This is one reason long term asset ownership plays such a central role in generational wealth planning.

It is not about avoiding taxes through shortcuts.

It is about understanding time, structure, and incentives.


Why the Government Allows This

At first glance, it may seem like the government is overly generous.

In reality, the government is playing a long term game.

Investments create businesses.

Businesses create jobs.

Employees pay income taxes.

Businesses pay corporate taxes.

Assets generate economic activity.

Sales eventually trigger capital gains taxes.

The government benefits many times over from the initial incentives it provides.

This is why the tax code consistently favors investment and ownership over wages alone.


The Bigger Picture

If you earn only W2 income, you will generally pay the highest effective tax rates.

If you invest in the areas the government wants to grow, real estate, businesses, energy, and innovation, you are rewarded for taking that risk.

This is not about exploiting loopholes.

It is about learning the rules of the system and choosing to play intentionally.

The goal is not to avoid responsibility, but to gain clarity.

When you understand why the tax code works the way it does, you stop feeling frustrated and start making informed decisions.

And that shift alone can change the trajectory of your financial life.

If you want to continue learning how investing, taxes, and long term planning fit together, make sure to explore the additional resources linked below and subscribe for future content.

Understanding the system is the first step to using it wisely.

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