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One Stop Tax Strategists
May 24, 2025
3 min read

3 overlooked tax strategies the wealthy use…and how you can too.

Let’s face it…most real estate investors and business owners are unknowingly tipping the IRS every year.

Not because they want to.

But because they’re simply not aware of the tax strategies available to them.

We’re on a mission to change that.

Here are 3 tax-saving strategies that high-level investors are using, and most accountants never bring up.

1. Reduce Capital Gains Without a 1031 Exchange

Selling a property or business with a big gain? You’re probably bracing for that massive tax bill. But what if you didn’t have to pay it—at least not all at once?

Here are a few lesser-known strategies that can reduce or eliminate capital gains:

Charitable LLC: Structure deals in a way that supports causes you care about while slashing your capital gains exposure.
Deferred Escrow Trust: Defer capital gains by keeping the transaction in extended escrow and strategically managing the timing.
Charitable Lead Trust (CLT): Donate the income from an asset to charity for a period of time, then return the asset (or its remainder value) to your heirs.
Charitable Remainder Trust (CRT): Transfer appreciated assets to a trust that pays you income for life or a set term, then donates the remainder to charity—minimizing or eliminating capital gains upfront.
Step-Up in Basis (aka the Grim Reaper Strategy): Transfer appreciated property to an aging parent to avoid capital gains altogether.

📌 Real Example: One client was facing a $2.2M tax bill after selling his business. We helped him set up a Charitable LLC and reduced it to $128,000. That’s over $2 million in savings… without a 1031 or giving up control.

2. Move Income Strategically to Someone in a Lower Tax Bracket

You might be thinking: "I make the money, so I pay the taxes."

But the IRS doesn’t require you to carry the whole load.

Here’s how we help savvy investors shift income to family members in lower tax brackets:

Create a second business that performs real services (e.g., admin or marketing).
Make your spouse, parent, or adult child a passive shareholder.
Pay that business from your main company and let the income be taxed at their lower rate.

📌 Real Example: Our client Juan used this with his mom. She became a shareholder in his second business. Instead of paying her $80K in post-tax money to help with expenses, he shifted income through the business…saving $40,000 in taxes in one year alone.

📌And bonus: One client used this strategy to help his college-aged daughter qualify for in-state tuition.

3. Defer Income Like the Wealthy Do

Most people get stuck asking, “How much tax do I owe?”

The better question is: “When do I want to pay tax?”

With a properly structured deferral strategy (what we call the Kick the Can Plan), you can push income into future years and invest the savings today.

📌 Real Example: One client deferred over $15 million in income and used that capital to build a real estate portfolio now worth $26 million. After layering in depreciation and cost segregation studies, we helped reduce his final tax bill to under $2 million—with more deferral still in place.