HeyJaredA Smarter Way To Retire with Tony Leonardi, CFP®
A Smarter Way to Retire is your guide to building a confident financial future. Hosted by Tony Leonardi, CFP® this podcast breaks down the key steps to retirement planning in a clear, actionable way.
- Indexed episodes, last 90 days
- 12
- Latest publication
- Sep 25, 2026
- Audience
- Checking…
- Earliest in this view
- Jul 10, 2026
Latest episodes
Medicare Enrollment and IRMAA: The Other October Deadline (opens the original)
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October 15 through December 7 is Medicare Annual Enrollment— not the Social Security claiming window. Tony Leonardi, CFP®, explains what you can change this fall,why the January–March window is only for people already on Medicare Advantage, and how IRMAA uses a two-year lookback. Official 2026 CMS figures: standardPart B is $202.90; the first surcharge starts above $109,000 single or $218,000 joint. Roth conversions, RMDs, capital gains, and even municipal-bond interest can push MAGI over that l
Social Security Optimization: Claiming Age, COLA Headlines, and Taxes (opens the original)
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Does a 3.6% Social Security COLA mean more money to spend? Not automatically. Medicare premiums, IRMAA, and taxes can take a bite out of the raise. In this episode of A Smarter Way to Retire, CFP® professional Tony Leonardi covers Social Security optimization before October: claiming age, how benefits get taxed, and what to model so you are not reacting to a headline. What you’ll learn • Why the 2027 COLA estimate (~3.6%) may not spend like a raise • Best age to claim Social Security — and why “
September Tax Planning 2026: Don’t Wait Until December for RMDs, Roths & IRMAA (opens the original)
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December 31 is the deadline. September is when the work should get done. In this episode of A Smarter Way to Retire, Tony Leonardi, CFP®, walks through why last-minute IRA withdrawals and Roth conversions can create April tax surprises — and Medicare IRMAA surcharges two years later. We use ahypothetical couple, Tom and Diane, to show what a napkin calculation misses: gains already taken, RMDs still due, and IRMAA cliffs. What we cover: • Why 2026 income can affect 2028 Medicare premiums • How t
End-of-Summer Money Check-In: Are You Still On Track for 2026? (opens the original)
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Labor Day weekend is the unofficial end of summer — and a useful moment to check whether 2026 is still on track. Tony Leonardi, CFP®, covers summer spending, cash reserves, and a simple four-part review of income, spending,investments, and taxes. Enjoy the barbecue, then make one adjustment for fall if you need it. Next week: year-end tax planning.
Don’t Leave Your IRA to Your Kids… Do This Instead | Tax-Efficient Retirement Legacy Planning (opens the original)
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Leaving a large traditional IRA to your kids can be one ofthe most expensive retirement mistakes a family makes. In this episode of *A Smarter Way to Retire*, Tony Leonardi, CFP®, explains the difference betweenthe tax you pay on withdrawals during your lifetime and the tax your heirs may pay on the remaining pre-tax balance under the 10-year rule. A traditional IRA is tax-deferred, not tax-free. You pay taxon what you take out. What is still in the account at death is still pre-tax —and most no
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