A Smarter Way To Retire with Tony Leonardi, CFP®

Anthony Leonardi
  • 5.0 (6)
  • 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. 2d ago

    How to Fund Your 3 Retirement Buckets Tax-Efficiently

    Once you’ve organized your retirement savings into three buckets, the next important step is learning how to fund them in a tax-efficient way. In this episode, Tony Leonardi, CFP® explains how to strategically fill each of the three buckets — the Early Retirement Income Bucket, the Longer-TermLive On Bucket, and the Leave On Bucket — while considering taxes, RMDs, IRMAA, and legacy planning. You’ll learn: -Why the best way to fund each bucket depends on your specific situation -When it makes sense to use taxable vs. tax-deferred accounts in Bucket 1 -How to use Roth conversions and strategic withdrawals in Bucket 2 -Why Bucket 3 is often ideal for Roth conversions and legacy strategies Free Resources: -Take the Smart Retirement Strategy Quiz:LeonardiFamilyWealthcare.com/quiz -Download the Roth IRA Conversion Playbook (Free) -Download the Smart Tax Shield Legacy Playbook (Free) Timestamps: 00:00 – Introduction & 3-Bucket Recap 02:17 – Refining TaxWithdrawal Strategies 04:47 – Bucket 1: Early Retirement Income Bucket Funding09:21 – Bucket 2: Longer-Term Live On Bucket Strategies 12:37 – Bucket 3: Leave On Bucket & Legacy Planning 14:18 – Key Principles for Tax-EfficientFunding 16:44 – Why Personalization Matters + CTAIf you’d like help building and funding your own 3-bucket retirement plan, book a complimentary 15-minute call at LeonardiFamilyWealthcare.com. #RetirementPlanning #TaxEfficientRetirement #3BucketStrategy#RothConversions #SmartRetirement

  2. Jul 17

    The 3-Bucket Retirement Strategy Most People Are Missing

    Most people only think about two buckets of retirement money— what they’ll spend and what they’ll leave to their kids. But there’s a critical third bucket that can make a significant difference, especially in the early years of retirement.   In this episode, Tony Leonardi, CFP® explains why adding an**Early Retirement Income Bucket** (designed to cover the first 3–5 years of retirement spending) can be helpful for **helping to protect** against Sequenceof Returns Risk.   You’ll learn: - Why the traditional two-bucket approach is often notenough - How Sequence of Returns Risk can impact early retirement - The purpose of the Early Retirement Income Bucket - How the 3-bucket system gives you better clarity andstructure   This episode builds on our conversation about Live On vsLeave On assets and introduces a practical framework for the early years of retirement.   Free Resources: - Take the Smart Retirement Strategy Quiz →LeonardiFamilyWealthcare.com/quiz - Book a complimentary Smart Retirement Model call   If you’re within 5 years of retirement or recently retired,this is an episode you won’t want to miss.   #RetirementPlanning #SequenceOfReturns #3BucketStrategy#EarlyRetirement

  3. Jul 10

    How to Handle Long-Term Care Without Paralyzing Your Retirement Plan

    Many people know long-term care is expensive and that theymight need it one day, but they haven’t actually addressed it in their retirement plan. As a result, the concern often lingers in the background like a dark cloud.   In this episode, Tony Leonardi, CFP® explains how to stopavoiding the issue and start dealing with it practically using the Live On vs Leave On framework.   You’ll learn: - Why leaving long-term care unaddressed creates unnecessarystress - How to quantify the potential cost of care - Three realistic ways to handle long-term care:Self-insuring with Leave On assets, Traditional long-term care insurance, andHybrid (asset-based) policies - The pros and cons of each approach and how they impactyour overall plan   If you’ve been putting off long-term care planning becauseit feels overwhelming, this episode will help you think about it more clearly and make a conscious decision.   **Free Resources:** - Take the Smart Retirement Strategy Quiz:LeonardiFamilyWealthcare.com/quiz - Download the Roth IRA Conversion Playbook and Smart TaxShield Legacy Playbook (free on our website)   **Timestamps:** 00:00 – Introduction  01:45 – Why Long-Term Care Planning Often Gets Ignored  04:20 – Step 1: Quantify the Potential Cost  06:10 – Option 1: Self-Insuring with Leave On Assets  08:45 – Option 2: Traditional Long-Term Care Insurance  11:20 – Option 3: Hybrid / Asset-Based Policies  14:30 – Final Thoughts & Smart Retirement Model Offer   If you have substantial retirement savings and want helprunning the numbers on long-term care, book a complimentary 15-minute call atLeonardiFamilyWealthcare.com.   #LongTermCare #RetirementPlanning #LiveOnVsLeaveOn#TaxStrategy #LegacyPlanning

  4. Jun 29

    How to Structure Your Retirement Savings for Both You and Your Heirs

    Most retirees make one costly mistake — they treat all their retirement savings the same way. But not all retirement dollars have the same purpose. In this webinar, Tony Leonardi, CFP®, explains the critical distinction between Live On Assets (money you’ll spend during retirement) and Leave On Assets (money intended for your children and grandchildren). You’ll learn: -Roth IRA Conversion Playbook (2026 Edition) -Smart Tax Shield Legacy Playbook -Smart Retirement Strategy Quiz (18 unique retireeprofiles) Free Resources Mentioned: -Roth IRA Conversion Playbook (2026 Edition) -Smart Tax Shield Legacy Playbook -Smart Retirement Strategy Quiz (18 unique retireeprofiles) All available for free at LeonardiFamilyWealthcare.comTimestamps: 00:00 – Introduction & Agenda 02:30 – The Costly Mistake Most Retirees Make 05:45 – Live On vs Leave On Assets Explained 09:20 – How We Calculate Your Two Buckets 14:10 – Why This Distinction Matters (Taxes, Risk& Legacy) 20:40 – Real Client Examples ($1.5M and $4M Portfolios) 28:15 – Smart Strategies for Each Bucket 35:00 – The Smart Retirement Strategy Quiz38:20 – Complimentary Smart Retirement Model Offer If you have substantial retirement savings and want a more personalized plan, book a quick 15-minute call with Tony at LeonardiFamilyWealthcare.com. #RetirementPlanning #LiveOnVsLeaveOn #TaxStrategy #LegacyPlanning#RetirementLegacy #SmartRetirement

  5. Jun 19

    The $1.5 Million Retirement Trap Most Successful Savers Fall Into

    If you have $1.5 million or more in retirement accounts — and you don’t actually need all of it to live on comfortably — this episode is for you. In this video, Tony Leonardi, CFP®, reveals the hidden problem that affects many successful savers: Without proper planning, the IRS can end up as one of your largest “heirs” — taking two bites at the same retirement savings. You’ll learn: -Why RMDs and the 10-year inherited IRA rule can cost your family hundreds of thousands (or more) in taxes -The critical distinction between Live On assets (for you) and Leave On assets (for your heirs) -How to structure your plan more intelligently for both your lifestyle and your legacy Whether you have strong pension income, substantial non-retirement savings, or simply more in IRAs and 401(k)s than you need, this episode will show you how to avoid the common traps most successful savers fall into. Take the Free Smart Retirement Strategy Quiz Discover which of the 18 retiree profiles best matches your situation: → LeonardiFamilyWealthcare.com/quiz Free Guides Mentioned: -Roth IRA Conversion Playbook (2026 Edition) -Smart Tax Shield Legacy Playbook Both available for free on my website.Timestamps: 00:00 – Introduction: The $1.5M+ Retirement Trap 02:10 – Why the IRS Takes Two Bites at Your Savings 05:30 – Live On vs Leave On Assets Explained09:15 – Real Impact on You and Your Heirs 12:40 – The Smart Retirement StrategyQuiz 14:20 – Next Steps & Complimentary Smart Retirement Model Offer If you have substantial retirement savings and want a smarter, more personalized plan, book a quick 15-minute call with me:LeonardiFamilyWealthcare.com #RetirementPlanning #TaxStrategy #LegacyPlanning #SmartRetirement#HighNetWorth #RetirementTrap

  6. Jun 12

    The Smart Retirement Strategy Quiz – Which of the 18 Profiles Are You?

    Most retirement advice is too generic. That’s why I created the Smart Retirement Strategy Quiz — it identifies which of the 18 unique retiree profiles best matches your situation. In this episode, Tony Leonardi, CFP® explains the four key questions behind the quiz and shares three common profiles so you can start thinking about where you fit. You’ll learn: Live On vs Leave On assets and why it matters The “two bites” problem with inherited IRAs How your tax focus, charitable goals, and concern about running out of money shape your ideal plan Tailored resources based on your profile (including the Smart Tax Shield Legacy Playbook and Roth Conversion Playbook) Take the free quiz here: https://form.typeform.com/to/jKGvC0CS LeonardiFamilyWealthcare.com Timestamps: 00:00 – Introduction to the Smart Retirement Strategy Quiz 01:30 – The Four Key Questions 04:20 – The Two Bites Problem 06:10 – Three Sample Profiles09:30 – What You’ll Get + Tailored Resources 11:45 – Next Steps & Smart Retirement Model Offer #SmartRetirement #RetirementQuiz #RetirementPlanning #LiveOnVsLeaveOn#TaxStrategy

  7. Jun 5

    Trump Accounts for Kids: Everything Parents & Grandparents Need to Know in 2026

    New in 2026 — Trump Accounts (Section 530A) give families apowerful way to save for children and grandchildren with tax-deferred growth and a $1,000 government seed contribution.   In this episode, Tony Leonardi, CFP® breaks down: - Who qualifies and how to open an account - Contribution limits and growth potential (including realnumbers at 6% and 7%) - How Trump Accounts compare to 529 plans, UGMA/UTMA,brokerage accounts, and Roth IRAs - Why grandparents should strongly consider this tool forgenerational wealth   Whether you’re a parent or grandparent, this is one of thebest new opportunities to give kids a financial head start.   **Timestamps:** 00:00 – Introduction to Trump Accounts 02:10 – Key Features & Eligibility 04:30 – How to Open an Account 07:45 – Growth Projections at 6% and 7% 12:20 – Comparison with 529s, UGMA, and Roth IRAs 17:00 – Action Steps & Modeling Offer   Ready to see how this fits into your family plan? Book afree 15-minute call and I’ll run your Smart Retirement Model.   Link: LeonardiFamilyWealthcare.com   #TrumpAccounts #Section530A #SavingForKids#GrandparentWealth #RetirementPlanning #FinancialPlanning

  8. May 29

    Charitable Lead Trusts: Reduce Estate Taxes While Supporting Charity

    If you have a large estate and want to support causes you care about while potentially reducing taxes for your children, a Charitable Lead Trust (CLT) may be worth exploring. In this episode, Tony Leonardi, CFP®, breaks down how Charitable Lead Trusts work, who they’re best suited for, and how they can help reduce the taxable value of assets passed to the next generation. You’ll learn: How a CLT flips the traditional trust structure — paying charity first, then passing remaining assets to your heirs A realistic example of a $42 million estate and how a CLT couldpotentially save $2M – $3.5M+ in estate taxes Key advantages, risks, and important considerations before moving forward Why this strategy is mainly an estate tax tool (not an income tax tool) This is an advanced planning strategy — not for everyone — but it can bevery powerful for the right family. Timestamps: 00:00 – Introduction to Charitable Lead Trusts 01:45 – How a CLT Works03:20 – Real Example: $42 Million Estate 06:10 – Potential Tax SavingsBreakdown 09:30 – Important Risks & Considerations 12:15 – Who ThisStrategy May Be Right For 14:00 – Next Steps & Smart Retirement Model Offer If you're concerned about estate taxes and want to explore smarter ways to support charity while protecting your legacy, this episode is for you. 👉 Ready to see how strategies like thiscould impact your plan? Book a complimentary 15-minute call and I’ll build yourSmart Retirement Model at no cost or obligation: →LeonardiFamilyWealthcare.com Free Resources: • Smart Tax Shield Legacy Playbook → • Roth IRA ConversionPlaybook 2026 → LeonardiFamilyWealthcare.com #CharitableLeadTrust #EstateTaxPlanning #LegacyPlanning#RetirementPlanning #TaxStrategy #CFP

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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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