šŸ’ø #0012 - 3 Tax-Saving Strategies for Big Gains

Most investors leave money on the table when selling assets. Don’t make the same mistake.

Big Gains, Big Problems

How to Save More When You Sell

When your investments soar, so do the taxes.

Without a strategy, selling highly appreciated assets could mean handing over 20% or more of your gains to Uncle Sam.

But with smart planning before you sell, you can keep more of your wealth working for you instead of paying it out in taxes.

Read on for the details…

In today’s issue:

  • Weekly Wisdom - From Jean-Baptiste Colbert…

  • Best Links - Wildfires crushing the insurance industry…

  • Deep Dive - How three celebrities can support causes and stay rich…

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The Secret That Changed the Way I Manage My Wealth Forever

Most high earners lose millions over time—see how I learned to avoid the hidden traps

Last week, I met with one of our readers who had a familiar problem. They were earning a great income, saving consistently, and even investing. But their wealth wasn’t growing as quickly as they would like.

They told me, ā€œI don’t get it. I’m doing everything I’m supposed to, but my money just isn’t growing the way I planned.ā€

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Fifteen years ago was the first time I had a seven figure income in one year, but I didn’t realize how many pigs would be at the trough.

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WISDOM

ā

"The art of taxation consists in so plucking the goose as to obtain the largest amount of feathers with the least amount of hissing." 

– Jean-Baptiste Colbert

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DEEP DIVE

3 Tax-Saving Strategies for Big Gains

Plan ahead to keep more of your wealth. The right strategy before selling can save you thousands—or even millions.

Imagine this: You’ve been holding onto that Bitcoin or Tesla stock for years.

It’s grown significantly, but now you’re stuck—sell and face a massive tax bill, or hold and risk losing gains to market swings?

The key to maximizing your wealth lies in planning your tax strategy before you sell.

Let’s break it down…

Why Tax Planning Matters Before Selling

Once you sell an investment, the tax liability is locked in. This is bad.

You’ve created the tax obligation to Uncle Sam for a cut of your gains, whether you’re ready or not.

Planning ahead gives you flexibility and tools to reduce or even eliminate those taxes.

As real estate mogul Donald Trump demonstrated with 1031 exchanges, the real power of tax strategies lies in avoiding the liability before it starts.

1. Defer Taxes with a 1031 Exchange

Turn real estate profits into bigger opportunities—tax-free.

If you’re a real estate owner, the 1031 exchange is your best friend. It allows you to sell a property and reinvest in a ā€œlike-kindā€ property without paying immediate capital gains tax.

Celebrity Example:

When Tom Cruise sold his Telluride ski chalet, he could have used a 1031 exchange to reinvest in other real estate without triggering taxes. This could have helped him preserve millions for reinvestment while upgrading his portfolio.

Why Plan Ahead?

To qualify for a 1031 exchange, you must identify replacement properties within 45 days and complete the purchase within 180 days. Start strategizing before you sell.

2. Reinvest Gains in Opportunity Zones

Save on taxes and make an impact.

Opportunity Zones let you defer and reduce taxes by reinvesting gains into designated funds that support underserved communities.

Celebrity Example:

LeBron James has invested in numerous projects to build schools and develop communities. This would be ideal for Opportunity Zone structure because they take place in low-income neighborhoods. These investments reduce his tax liability while aligning with his philanthropic goals.

Why Plan Ahead?

You need to move gains into an Opportunity Zone Fund within 180 days of selling the asset. Missing this window can cost you the tax benefits.

3. Sell Tax-Free with a Charitable Remainder Trust (CRT)

Turn your gains into income and a legacy.

A CRT allows you to transfer appreciated assets to a trust, avoiding immediate capital gains taxes.

The trust sells the assets tax-free, provides you with income for the rest of your life, and donates the remainder to charity.

Celebrity Example:

Jackie Chan, known for his philanthropy, has an opportunity to use trusts to balance charitable giving with financial security and asset protection. While details of his charitable aren’t public, this strategy aligns with his legacy planning goals.

Why Plan Ahead?

Setting up a CRT takes time and legal coordination. Waiting until after the sale forfeits this option.

Try it out at:

Recap

How the Wealthy Save on Taxes

  • 1031 Exchanges: Sell and reinvest real estate tax-free (e.g., Tom Cruise).

  • Opportunity Zones: Reinvest gains to defer and reduce taxes (e.g., LeBron James).

  • Charitable Remainder Trusts: Sell tax-free, earn income, and donate the remainder (e.g., Jackie Chan).

Act Now to Keep More of What You Earn

The biggest mistake you can make? Waiting until after you’ve created a tax liability to think about strategy.

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The content provided in this newsletter is for informational purposes only and should not be considered as specific advice for any specific individual. The information is prepared by knowledgeable individuals and is not written by certified tax professionals or investment advisors. For personalized advice tailored to your unique financial situation, consult with a qualified tax professional, financial advisor, or attorney.

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