Man with black hair sitting down with a blue shirt pointing to a board with a pie chart and a bar graph with an arrow indicating upwards. A girl with black hair faces towards the man. The words "How the Richest Men in the US Avoided Taxes (Legally)

How to Avoid Taxes Like the Richest Man in U.S. History

Did you know that when John D. Rockefeller and Andrew Carnegie were nearing the end of their lives, they competed to see who could give away more of their fortune?

At the time, Rockefeller’s net worth in 1937 was $1.4 billion. That was about 1.5 percent of the entire U.S. GDP. In today’s dollars, that is equivalent to more than $37 trillion.

This was not just a philanthropic effort. It was also a savvy tax move.

Fast forward to today, and there is a charitable giving tool that allows everyday business owners, professionals, and high earners to take advantage of similar tax rules. It is called a Donor Advised Fund (DAF).

Let’s dive in.


 

What Is a Donor Advised Fund?

A Donor Advised Fund is like having your own charitable foundation without the administrative complexity. You contribute money or assets to the fund, receive an immediate tax deduction, and then direct those funds to your favorite charities over time.

This approach creates flexibility. You can donate when it is most advantageous for tax purposes while waiting to decide which causes to support.

Learn more from the IRS about Donor Advised Funds.

 

How Does a DAF Work for Tax Savings?

When you contribute to a Donor Advised Fund, you get an immediate tax deduction, even if the money does not go to a charity right away. This creates powerful tax planning opportunities:

    • Reduce taxable income in high-earning years.

    • Bunch donations together to maximize deductions if you itemize.

    • Avoid capital gains tax on appreciated assets.

    • Grow your charitable dollars tax-free until you decide where to give.

For high earners, this strategy can be a game-changer. It lets you move money into the fund when you need the tax break most while still taking your time to allocate donations.

Cyan colored background with cartoon arm of someone dropping a coin into a donation box

 

What Can You Donate to a Donor Advised Fund?

Cash is the simplest option, but the biggest benefits often come from donating appreciated assets such as:

    • Stocks and securities: Deduct the full market value and avoid capital gains tax.

    • Real estate: Vacation homes or investment property can provide significant deductions.

    • Private business interests: Ideal for entrepreneurs or those with equity holdings.

    • Cryptocurrency: Even digital assets can be donated to avoid large taxable gains.

By donating these assets, you remove them from your taxable estate, deduct their fair market value, and avoid capital gains tax. That is a triple benefit.

For a deeper dive on rules for donating appreciated assets, see Fidelity Charitable’s guide to DAF contributions.

 

How Do Funds Get to Charities?

Once your contribution is in the DAF, you recommend grants to IRS-recognized charities. The administrator then sends the funds on your behalf.

Eligible organizations include:

    • National nonprofits like the American Red Cross.

    • Local food banks, shelters, and schools.

    • Religious institutions.

    • Accredited educational institutions.

To evaluate charities before donating, tools like Charity Navigator can help ensure your dollars create the greatest impact.

 

Why Should Professionals and Business Owners Care?

Donor Advised Funds are not just for the ultra-wealthy. They provide:

    • Tax-efficient wealth management: Keep more of your income while supporting causes you value.

    • Long-term charitable impact: Contributions can grow tax-free until you distribute them.

    • Flexibility with timing: Make contributions in a high-income year and distribute over time.

In other words, you do not need Rockefeller’s fortune to benefit from this strategy.

 

Final Thoughts

A Donor Advised Fund is more than a tax deduction. It is a tool for building a legacy. By using a DAF, you can support meaningful causes, reduce your tax burden, and take a strategic approach to giving.

You work hard for your money. With the right strategy, you can keep more of it and make a bigger impact.

If you are ready to explore how a Donor Advised Fund could fit into your tax and wealth plan, schedule a consultation with Bement Company.