A Smarter Way To Retire with Tony Leonardi, CFP®

Anthony Leonardi
  • 5.0 (7)
  • Investing
  • Updated Weekly

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. Whether you’re approaching retirement or already there, you’ll get expert insights on financial modeling, wealth preservation, and making informed decisions for your future. Tune in for practical advice, thoughtful discussions, and a smarter way to retire. See website for full disclosures: www.LeonardiFamilyWealthcare.com

  1. 3d ago

    Inherited IRA 10-Year Rule: What Adult Children Need to Know

    Most adult children who inherit a traditional IRA after 2019cannot stretch withdrawals over a lifetime. Tony Leonardi, CFP®, walks through the SECURE Act 10-year rule, eligible designated beneficiaries, annual inherited RMDs when the owner had already started distributions, estates andcharities as beneficiaries, and why waiting until year 10 can stack income, state tax, and IRMAA. Educational only — confirm your facts with a custodianand tax professional.   Fit Call: Leonardifamilywealthcare.com/fit-call  Guides: Leonardifamilywealthcare.com  Disclosures on the website.  Because there is A Smarter Way to Retire.

  2. Sep 25

    Medicare Enrollment and IRMAA: The Other October Deadline

    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 line. Crossing it by one dollar can apply the surcharge for the whole year.   Book a complimentary 15-minute Fit Call atLeonardiFamilyWealthcare.com/fit-call. Playbooks are under Books and Guides.Please see the website for full disclosures.

  3. Sep 18

    Social Security Optimization: Claiming Age, COLA Headlines, and Taxes

    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 “always wait until 70” is aslogan, not a plan• How much more you get from 67 to 70 (about 24%) and when you break even• Early claiming at 62: about a 30% permanent cut from full retirement age• The earnings test if you claim early and keep working• Is Social Security taxable? Provisional income lines of $25k / $32k and $34k/ $44k• Why one IRA withdrawal or Roth conversion can tax more of your benefit andraise IRMAA two years later• Four things to model before mid-October Chapters00:00 Welcome + Tony and Maddie’s wedding01:30 Does a COLA mean more spending money?03:45 When is the best age to claim Social Security?08:00 67 vs 70: 24% more and the breakeven11:00 Mark and Pat: health, cash, survivor benefits13:30 Earnings test if you keep working15:00 Is Social Security taxable?18:00 Roth conversions, IRMAA, and stacking income21:00 What to model before October24:00 DIY spreadsheets vs a real model Fit Call: https://calendly.com/anthony-leonardi-leonardifwc/retirementWebsite / Books and Guides: https://www.leonardifamilywealthcare.comPlease refer to the website for full disclosures and additional resources. #SocialSecurityOptimization #TaxEfficientRetirement#RetirementIncomeStreams #IRMAA #RothConversion #CFP #ASmarterWayToRetire Apple / SpotifytitleSocial

  4. Sep 11

    September Tax Planning 2026: Don’t Wait Until December for RMDs, Roths & IRMAA

    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 to build a year-to-date income picture before adding more taxable income• RMD timing, including first-year delays that can stack two withdrawals• QCDs for 2026 (limit $111,000 per person) and why paperwork should start now• Roth conversions as a full-year decision, not a December reflex• Tax-loss harvesting in taxable accounts before year-end• Why DIY spreadsheets often miss the combined tax, RMD, and IRMAA effect Book a complimentary 15-minute Fit Call:https://calendly.com/anthony-leonardi-leonardifwc/retirement Free Roth IRA Conversion Playbook (2026 Edition):https://www.fmgwebsites.com/d54859da-0e12-4038-be06-9bd78dad323b/roth-ira-conversion-playbook-2026-edition Smart Tax Shield Legacy Playbook:https://www.fmgwebsites.com/d54859da-0e12-4038-be06-9bd78dad323b/smart-tax-shield-legacy-playbook Website and disclosures:https://www.leonardifamilywealthcare.com Listen on Apple Podcasts:https://podcasts.apple.com/us/podcast/a-smarter-way-to-retire/id1793796703 Listen on Spotify:https://open.spotify.com/show/643N9lbuQYiXXc188Rb1z8 Subscribe for weekly retirement income planning, tax-efficient retirementstrategies, and Social Security / RMD education. #RetirementPlanning #TaxEfficientRetirement #RothConversion #RMD #IRMAA #QCD#RetirementIncomePlanning #CFP #ASmarterWayToRetire Please see LeonardiFamilyWealthcare.com for full disclosures. Educationalcontent only. Not tax, legal, or personalized investment advice.

  5. Sep 7

    End-of-Summer Money Check-In: Are You Still On Track for 2026?

    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.

  6. Aug 28

    Don’t Leave Your IRA to Your Kids… Do This Instead | Tax-Efficient Retirement Legacy Planning

    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 non-spouse heirs generally must empty that remaining balance within 10 years.   If you have a sizable IRA or 401(k) you don’t need to spend,this episode will change how you think about Leave-On assets, inherited IRAs, and tax-efficient legacy planning.   You’ll learn:  • Why inherited traditional IRAs do not get a step-up inbasis  • How the 10-year rule can push your kids into higher taxbrackets  • The difference between Live-On assets and Leave-Onassets  • Why you usually cannot maximize tax savings for yourselfand your heirs at the same time  • 4 strategies that may help: spend the IRA first, Rothconversions, distribute and reinvest, and the Smart Legacy Tax Shield    Example discussed: a $1.5 million IRA that grows to about$2.1 million — with a potential tax bill of $700,000 to $850,000 for the next generation.   Free resources:  📘 Book: *A Smarter Way toRetire* — https://www.leonardifamilywealthcare.com  📘 Smart Tax Shield LegacyPlaybook — https://www.leonardifamilywealthcare.com  📘 Roth IRA ConversionPlaybook, 2026 Edition —https://www.leonardifamilywealthcare.com/roth-ira-conversion-playbook    Want to see how much of your portfolio is Live-On vsLeave-On? Book a complimentary 15-minute call and Smart Retirement Model (while calendar openings last):  https://www.leonardifamilywealthcare.com    Listen on Apple Podcasts:  https://podcasts.apple.com/us/podcast/a-smarter-way-to-retire/id1793796703    Listen on Spotify:  https://open.spotify.com/show/643N9lbuQYiXXc188Rb1z8    Subscribe for weekly retirement income planning,tax-efficient retirement strategies, and legacy planning.  Please refer to the website for full disclosures andadditional resources.   #RetirementPlanning #TaxEfficientRetirement #InheritedIRA#RothConversion #EstatePlanning #CFP #ASmarterWayToRetire #LegacyPlanning #RMD#WealthPreservation   This content is for educational purposes only and should notbe considered tax, legal, or investment advice. Life insurance and annuitiesare long-term products subject to underwriting and the claims-paying ability ofthe issuing company. Results vary based on individual circumstances.

  7. Aug 21

    Reverse Dollar Cost Averaging & The 50/100 Rule

    Once you retire, investing becomes a differentgame. Market drops no longer help you buy more shares — they force you to sell more shares. Combined with the 50/100 Rule, early volatility can permanently damage a retirement plan. In this episode, Tony Leonardi explains the twoforces working against retirees and what you can do about them.

  8. Aug 14

    Stress-Testing Your 3-Bucket Retirement Plan

    Most retirement plans look fine when everything goes smoothly. Real life rarely does. In this episode of A Smarter Way to Retire, Tony Leonardi walks through how to stress-test a three-bucket retirement income plan against the challenges that actually show up: • Sequence of returns risk in the early years • Higher inflation •Longevity (living into your 90s or beyond) • Elevated spending periods • Asset allocation inside each bucket • Combined stresses You’ll also get a quick review of the three buckets and see why this structure is built with difficult conditions in mind. Timestamps: 0:00 – Introduction & garden update 1:45 – Quick review of the 3-bucket approach 4:30 – Why stress-testing matters 6:15 – Key scenarios we test 11:40 – How the three buckets respond under stress 14:20 – Practical example 16:30 – What to do with the results 18:00 – Next steps & Smart Retirement Model Want to see how your own plan holds up? Book a complimentary 15-minutecall: LeonardiFamilyWealthcare.com #RetirementPlanning #ThreeBucketStrategy #SequenceOfReturns#RetirementIncome #TonyLeonardiCFP

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About

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. Whether you’re approaching retirement or already there, you’ll get expert insights on financial modeling, wealth preservation, and making informed decisions for your future. Tune in for practical advice, thoughtful discussions, and a smarter way to retire. See website for full disclosures: www.LeonardiFamilyWealthcare.com

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