A Smarter Way To Retire with Tony Leonardi, CFP®

Anthony Leonardi
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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. 11h ago

    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.

  2. 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

  3. Aug 7

    Withdrawal Strategies from the 3 Retirement Buckets | How to Take Income the Smart Way

    How should you actually withdraw money from your retirement savings once you stop working?   In this episode, I walk through practical withdrawalstrategies using the three-bucket retirement income approach. You’ll learn:   - Why you should generally spend from Bucket 1 first  - How to refill Bucket 1 without increasing risk  - The “slow drip” method using dividends and interest  - Why Bucket 3 should usually be protected  - How tax location fits into the three-bucket framework  - Common withdrawal mistakes that can quietly damage aplan    This is the natural follow-up to last week’s episode on howto invest each of the three buckets.   If you’d like to see how this strategy could work with yourown numbers, I’m offering to build your Smart Retirement Model at no cost or obligation while openings remain.    Book a quick call here:https://www.leonardifamilywealthcare.com   Subscribe for weekly retirement planning insights.  There really is a smarter way to retire.   #RetirementIncome #RetirementPlanning #ThreeBucketStrategy#SequenceOfReturns #TonyLeonardiCFP

  4. Aug 1

    Why You Shouldn’t Invest All Your Retirement Money the Same Way

    Once you’ve organized your retirement savings into threebuckets, the next important question is how to invest the money *inside* each one.   In this episode, Tony Leonardi, CFP® explains why a singleallocation (like 60/40 or 70/30) applied to your entire portfolio often fallsshort — and how matching investment strategy to the job of each bucket cancreate a more intentional approach.   You’ll learn: - Why investing *in* retirement is different from investing*for* retirement - How the Early Retirement Income Bucket is generallyinvested more conservatively for stability and availability - Why the Longer-Term Live On Bucket often uses a balancedor moderately growth-oriented mix - How the Leave On Bucket can support a higher growthallocation due to its longer time horizon - Key principles and common mistakes when applying amulti-bucket investment approach   This discussion is high-level and educational. The rightinvestment mix depends on individual circumstances, risk tolerance, time horizon, and overall plan. Actual investment decisions should be made as part of a coordinated strategy with your advisor.   **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 & Series Recap  01:41 – Keeping the Discussion High-Level  03:05 – The Common Mistake of One-Size-Fits-AllAllocations  04:18 – Why the 3-Bucket Framework Helps  04:47 – Bucket 1: Early Retirement Income Bucket  06:48 – Bucket 2: Longer-Term Live On Bucket  08:55 – Bucket 3: Leave On Bucket  10:35 – Key Principles for Investing Across the Buckets  12:22 – Common Mistakes to Avoid  13:43 – The Role of Financial Modeling  14:23 – Quiz, Playbooks & Next Steps   If you’d like to explore how a three-bucket investmentapproach might apply to your situation, you can book a complimentary 15-minutecall at LeonardiFamilyWealthcare.com.   Please refer to the website for full disclosures andadditional resources.   #RetirementPlanning #3BucketStrategy #AssetAllocation#RetirementInvesting #SmartRetirement

  5. Jul 24

    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

  6. 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

  7. 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

  8. 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

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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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