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Compare a DST with a Self Directed 401K

Reef Point LLC · April 29, 2025 ·

When it comes to deferring capital gains on the sale of appreciated assets such as real estate, a business, or collectibles, the Deferred Sales Trust (DST) continues to stand out as a flexible and powerful strategy. One of the most effective ways to explain its advantages is by comparing it to something more familiar self-directed 401(k).

At Reef Point, we often use this comparison to help clients understand the unique benefits of the DST structure. Here’s how a DST operates similarly to a personal or self-directed 401(k) and in many ways, offers even greater adaptability and efficiency.

1. You Direct Reinvestment Decisions

Once your asset is sold and the proceeds are placed into the DST, the trust operates much like a personal self-directed 401(k). As the note holder, you have the ability to recommend how proceeds are reinvested, whether into real estate, stocks, private equity, or alternative investments.

2. Flexible Distributions Aligned With Your Needs

One of the most appealing features of a DST is the ability to customize the timing and amount of distributions. You decide what distributions to request and when, and those requests can be modified as your financial situation evolves.

3. Taxes Only on What You Withdraw

With a DST, you will only incur taxes on the distributions you choose to receive. Even if the trust earns income, you are only taxed on the amount you elect to take out in a given year. This provides meaningful opportunities for strategic tax planning.

4. Seamless Legacy and Estate Integration

The DST also works in tandem with your estate planning goals. When paired with a revocable living trust, the DST becomes one of your estate’s assets. You can establish beneficiaries, set distribution preferences, and leave detailed guidance for your successor trustee. Importantly, your passing does not trigger taxation, allowing your heirs to continue using the DST with the same tax deferral benefits.

5. Strong Asset Protection

Like a 401(k), the DST offers significant protection from potential future creditors. The assets within the DST are difficult, if not impossible to access through legal claims, making it a powerful safeguard for preserving your wealth.

If you’re planning to sell an appreciated asset and want to mitigate capital gains taxes, the Deferred Sales Trust offers unmatched flexibility, estate planning benefits, and financial protection. It’s not just a strategy for tax deferral it’s a long-term planning tool designed to help you preserve and pass on wealth more efficiently.

Interested in learning how the DST might fit into your financial goals? Contact Reef Point LLC free personalized consultation.

Schedule a Consultation or call us at 866-867-8633.

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Reef Point LLC was founded by Gregory H. Reese who is one of only 13 Trustees in the US for Deferred Sales Trusts.

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Costa Mesa, CA 92626
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As an authorized and approved Trustee for the Deferred Sales Trust and Member of the Estate Planning Team (EPT), Reef Point, LLC promotes the use of the Deferred Sales Trust™ or other estate planning techniques and is not responsible for recommendations made by other members of the Estate Planning Team, including the Deferred Sales Trust or other tax, legal or estate planning strategies.

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