THE TOM DUPREE SHOW | PODCAST SHOW NOTES

What Happens to Your Money When You’re Gone: A Practical Guide to Legacy Planning

The Tom Dupree Show | Dupree Financial Group | dupreefinancial.com | 859-233-0400

Air Date: April 25, 2026

Episode Description

Most people spend decades building their wealth. Far fewer spend even an hour making sure it ends up where they intend. In this special edition of The Tom Dupree Show, Tom Dupree and Mike Johnson walk through the essentials of legacy planning — not as a legal formality, but as a practical, ongoing discipline that protects both the people you love and the assets you’ve spent a lifetime growing.

The conversation covers beneficiary designations that override your will, the difference between who gets your assets, when they get them, and how much they actually keep after taxes. Tom and Mike also address Roth conversion strategies, required minimum distributions, the underappreciated advantages of taxable accounts, and creative charitable giving techniques that can reduce your tax burden while supporting causes that matter to you.

Most people spend a lifetime accumulating what they have — it’s a shame not to take an hour to make sure it goes exactly where you want it to go.

Topics Covered

Why beneficiary designations supersede your will — and what happens when they’re out of date
The three-bucket framework for legacy planning: who gets what, when they get it, and how much they keep
Trusts: when they’re genuinely necessary and when simpler solutions work just as well
The 10-year distribution rule for inherited IRAs and how it affects your heirs’ tax burden
Roth conversion strategies — and why they’re not a one-size-fits-all solution
Required minimum distributions: planning, consolidation, and the stiff penalties for getting it wrong
Qualified charitable distributions and how to gift appreciated stock tax-efficiently
Stepped-up cost basis in taxable accounts — a benefit that’s often overlooked in legacy planning
The oxygen mask principle: taking care of yourself financially before transferring assets to heirs
Why a dividend-income portfolio helps ensure you don’t outlive your money — and still have something to leave behind

Key Takeaways

Beneficiary designations override your will. Whatever your will says, the name on the beneficiary form wins. IRAs, 401(k)s, pensions, and life insurance policies all transfer directly to the listed beneficiary — bypassing probate entirely. Review these after every major life event.
Legacy planning doesn’t have to be complicated. A well-drafted basic will, combined with properly updated beneficiary designations, accomplishes what most families need. Complexity is occasionally warranted, but it should match your situation — not someone else’s billing rate.
Think in three buckets. Who gets your assets, when they receive them, and how much they keep after taxes. Each question has its own planning tools — and answering them clearly is the foundation of a solid plan.
Inherited IRAs now come with a 10-year clock. Non-spouse beneficiaries generally must fully distribute an inherited IRA within 10 years, paying income tax at their rate. Depending on your heirs’ tax situation, proactive planning — including Roth conversions — may reduce the overall tax hit.
Roth conversions are a tool, not a mandate. There’s a lot of marketing noise around Roth conversions. They make sense in some situations and not in others. The key is evaluating them in the context of your full financial picture, not as a standalone strategy.
Gifting appreciated stock to charity is one of the most tax-efficient moves available. You avoid capital gains on the appreciation, receive a deduction for the full fair market value, and the charity pays no tax. If you’re already planning to give, this approach can accomplish more with the same dollars.
Taxable accounts have underappreciated legacy advantages. Assets in taxable accounts receive a stepped-up cost basis at death, eliminating capital gains for your heirs. In some cases, a taxable account is a more tax-efficient inheritance than a pre-tax IRA.
Secure your own retirement first. Gifting assets while you’re still living can be meaningful — but not at the cost of your own financial security. Take care of your retirement income needs before making irrevocable transfers.

About The Tom Dupree Show

The Tom Dupree Show is hosted by Tom Dupree, founder of Dupree Financial Group and a 47-year veteran of the investment business. Each episode covers the financial topics that matter most to retirees and those approaching retirement — in plain English, without the Wall Street spin.

Dupree Financial Group is a fee-only, fiduciary Registered Investment Advisory firm based in Lexington, Kentucky. The firm manages separately managed accounts focused on income-generating, dividend-paying portfolios — no products sold, no commissions, no conflicts of interest.

Past episodes are available at dupreefinancial.com under the Radio tab.

Dupree Financial Group, LLC is an SEC-registered investment adviser located in Lexington, Kentucky. This content is provided for informational purposes only and does not constitute investment advice. Investments involve risk and are not guaranteed. Past performance is not indicative of future results.

Schedule a Complimentary Portfolio Review

If you’re not sure whether your beneficiary designations are current, your accounts are structured efficiently, or your legacy plan reflects where you are in life today — we’ll take a look. No charge. No pressure. Just an honest conversation about what you own and whether it’s working for you.

Call: 859-233-0400 | Visit: dupreefinancial.com

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