PODCAST · business
A Smarter Way To Retire with Tony Leonardi, CFP®
by Anthony Leonardi
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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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 mattersThe “two bites” problem with inherited IRAsHow your tax focus, charitable goals, and concern about running out of money shape your ideal planTailored 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/jKGvC0CSLeonardiFamilyWealthcare.comTimestamps: 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
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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 Accounts02:10 – Key Features & Eligibility04:30 – How to Open an Account07:45 – Growth Projections at 6% and 7%12:20 – Comparison with 529s, UGMA, and Roth IRAs17:00 – 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
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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 heirsA realistic example of a $42 million estate and how a CLT couldpotentially save $2M – $3.5M+ in estate taxesKey advantages, risks, and important considerations before moving forwardWhy 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 OfferIf 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.comFree Resources: • Smart Tax Shield Legacy Playbook → • Roth IRA ConversionPlaybook 2026 → LeonardiFamilyWealthcare.com#CharitableLeadTrust #EstateTaxPlanning #LegacyPlanning#RetirementPlanning #TaxStrategy #CFP
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Charitable Remainder Trusts: Tax-Efficient Strategy for Appreciated Assets
Tony Leonardi, CFP®, breaks down Charitable Remainder Trusts (CRTs) — an advanced planning strategy that may help individuals with appreciated assets potentially reduce capital gains taxes, generate lifetime income, and support charitable causes.In this episode, Tony walks through how CRTs work, shares a detailed example of a business owner comparing an outright sale versus using a CRT, and discusses important considerations including irrevocability and whether thisstrategy is a fit for your situation.This episode is designed for educational purposes. Any advanced planning strategy should be reviewed with your full advisory team.
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Why Leave On Assets (Especially IRAs) Are So Tax-Inefficient – And Four Smarter Ways to Fix It
If you don’t need your IRA for living expenses, it canbecome one of the most tax-inefficient assets to leave your children. The IRS often takes two bites at the same dollars — once during your lifetime and again when your heirs are forced to withdraw over 10 years. In this episode I show you the real cost with clear examplesand introduce four practical strategies under the Smart Legacy Tax Shield that let you pay tax once instead of twice. Download the free Smart Tax Shield Legacy PlaybookBook your no-cost Smart Retirement Model session →LeonardiFamilyWealthcare.com #LeaveOnAssets #SmartLegacyTaxShield #RMD #TaxPlanning#LegacyPlanning #SmartRetirement
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How to Minimize Taxes on Your Live On Assets in Retirement
Most retirees never separate their Live On assets (moneythey’ll spend) from their Leave On assets (money for heirs). This one mistake often leads to higher taxes, unnecessary risk, and a smaller legacy. In this episode I walk through the simple way to calculatethe split and share the four most effective strategies to minimize taxes on the money you actually need to live on — including Roth conversions, QCDs, smart withdrawal sequencing, and proper asset allocation. Download the free **Smart Tax Shield Legacy Playbook** →Book your no-cost Smart Retirement Model session →LeonardiFamilyWealthcare.com #LiveOnAssets #RetirementTaxPlanning #RMD #QCD#SmartRetirement
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Live On vs Leave On Assets: The Most Important Distinction in Retirement Planning
Last week we talked about paying tax once instead of twice.This week we go deeper: the critical difference between **Live On assets**(money you’ll spend) and **Leave On assets** (money for your heirs). Most people treat all their retirement accounts the same way— but once you separate them into these two buckets, everything changes:investment strategy, tax planning, and withdrawal approach. In this episode I show you:- How to calculate your Live On vs Leave On split- Why each bucket should be invested and taxed differently- A real client example where separating the bucketsimproved their probability of success from 78% to 94% If you have substantial retirement savings and some of thosedollars are intended for the next generation, this could be one of thehighest-leverage planning steps you can take. Download the new **Smart Tax Shield Legacy Playbook** (free)– link in description Book your free Smart Retirement Model session →LeonardiFamilyWealthcare.com #LiveOnVsLeaveOn #RetirementPlanning #AssetAllocation#TaxPlanning #LegacyPlanning #SmartRetirement
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Smart Retirement Tax Planning: Pay Tax Once, Not Twice (2026)
Many retirees don’t need their RMD income, yet face double taxation — once during their lifetime and again when heirs inherit the account. In this episode, Tony Leonardi introduces the Smart Retirement Tax Shield and Smart Legacy Tax Shield — two strategies to pay tax once instead of twice. Includes real client examples with significant projected lifetime tax savings.Download the free Smart Tax Shield Legacy Playbook and book your no-cost Smart Retirement Model at LeonardiFamilyWealthcare.com.
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Retirement Income Solutions 2026: How to Turn Your Savings Into Income You Can’t Outlive
How do you turn your savings into reliable retirement incomethat lasts as long as you do? Tony Leonardi, CFP® breaks down the best retirement income solutions for 2026 — including the bucket approach, protected income layers, guardrails, and blending sources. Plus why a good financialmodel is essential. Free Roth IRA Conversion Playbook 2026 Edition: https://www.leonardifamilywealthcare.com/roth-ira-conversion-playbook Because there IS a Smarter Way to Retire. #RetirementIncomeSolutions #RetirementIncomePlanning#TaxEfficientRetirement #BucketApproach #ProtectedIncomeLayer#ConfidentRetirement #WealthPreservation
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The 401(k) Tax Trap: Why Maxing Your 401k Can Backfire in Retirement
Maxing your 401(k) sounds smart — until the tax torpedo hitsin retirement.Tony Leonardi, CFP® explains the three tax buckets, how Social Security taxation creates hidden spikes, and why balanced retirement income planning is essential for tax-efficient retirement and legacy protection. Timestamps: 00:00 – The Trap Most Savers Fall Into 03:00 – The Three Tax Buckets 07:00 – The Most Valuable Planning Window 11:00 – Actionable Takeaways Download my free Roth IRA Conversion Playbook 2026Edition: https://www.leonardifamilywealthcare.com/roth-ira-conversion-playbook Because there IS a Smarter Way to Retire. #401kTaxTrap #TaxEfficientRetirement#RetirementIncomePlanning #TaxTorpedo #RothConversions #WealthPreservation#ConfidentRetirement
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Taxes and Roth Conversions 2026: 5 Strategies to Minimize Taxes in Retirement
Early April 2026 webinar recap: Tony Leonardi, CFP® shares 5powerful tax strategies — asset location, tax-efficient withdrawals, QCDs, Roth conversions, and tax-loss harvesting — to help you lower your tax bill and protect your legacy. Free Roth IRA Conversion Playbook 2026 Edition:leonardifamilywealthcare.com/roth-ira-conversion-playbook Free model build:calendly.com/anthony-leonardi-leonardifwc/15-minute-check-in-quick-questions-quick-answers Because there IS a Smarter Way to Retire. #TaxEfficientRetirement #RothConversions#RetirementIncomePlanning #QCDs #WealthPreservation #ConfidentRetirement
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Longevity 2.0: – Don’t Outlive Your Money
Living to 95 or 100 is more common than ever, but healthcarecosts can reach $315k+.Tony Leonardi, CFP® explains why old rules fail, howHSAs and annuities help, and how modeling boosts success rates. Timestamps: 00:00 – Intro & Longevity Reality 01:00 – Why Old Rules No Longer Work 04:00 – Real Client Story 07:00 – Action Plan 11:00 – Free Resources & Webinar Free Roth IRA Conversion Playbook 2026 Edition:leonardifamilywealthcare.com/roth-ira-conversion-playbook Free model build:calendly.com/anthony-leonardi-leonardifwc/15-minute-check-in-quick-questions-quick-answers Because there IS a Smarter Way to Retire. #LongevityRisk #TaxEfficientRetirement#RetirementIncomePlanning #HSAs #Annuities #ConfidentRetirement#WealthPreservation
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Sequence of Returns Risk: Protect Your Retirement from Early Market Dips
Sequence of returns risk can cut your retirement successrate by 50% if markets dip early.Tony Leonardi, CFP® explains how to use AI modeling, income floors, and annuities for tax-efficient retirement andconfident income planning. Timestamps: 00:00 – Intro & Why Sequence Risk Matters 01:00 – What Sequence Risk Really Is 04:00 – Real Client Stories 08:00 – Action Plan 12:00 – Free Resources Free Roth IRA Conversion Playbook 2026 Edition:leonardifamilywealthcare.com/roth-ira-conversion-playbook Free model build:calendly.com/anthony-leonardi-leonardifwc/15-minute-check-in-quick-questions-quick-answers Because there IS a Smarter Way to Retire. #SequenceOfReturnsRisk #TaxEfficientRetirement#RetirementIncomePlanning #ConfidentRetirement #WealthPreservation#RetirementFinancialAdvice
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RMD Traps in 2026: Proactive Planning to Slash Taxes & Preserve Your Legacy
RMDs in 2026 can quietly inflate taxes and erode yoursavings. Tony Leonardi, CFP® explains how to use QCDs, Roth conversions, and modeling to stay under IRMAA thresholds, reduce lifetime taxes by 20–30%, andpreserve more for your family. Timestamps: 00:00 – Intro & Why RMDs Matter Now 01:00 – RMD Basics & Traps 04:00 – Real Client Stories 08:00 – Actionable Steps 12:00 – Free Resources & Offer Free Comprehensive Guide: Roth IRA Conversion Playbook 2026Edition: leonardifamilywealthcare.com/roth-ira-conversion-playbook Free model build:calendly.com/anthony-leonardi-leonardifwc/15-minute-check-in-quick-questions-quick-answers Because there IS a Smarter Way to Retire. #RMDTraps #TaxEfficientRetirement #RetirementIncomePlanning#WealthPreservation #QCDs #LegacyPlanning #ConfidentRetirement
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Ep 58 | Roth Conversions 2026: Strategic Tax Savings Deep Dive
Tony Leonardi on Roth conversions: Pay low now vs. highlater. Timing, modeling, examples for 20s–retirees. Personal— not for everyone!Free quiz + book: LeonardiFamilyWealthcare.com/quiz. Because there IS a Smarter Way to Retire.
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The Power of Financial Modeling for Smarter Retirement
Tony Leonardi kicks off Year 2 with a deep dive on financialmodeling—calculate success, optimize portfolios, Roths, Social Security & more. Avoid sub-optimal guesses; free model offer! Quiz + book:LeonardiFamilyWealthcare.com/quiz. Because there IS a Smarter Way to Retire.Past performance is no guarantee of future results. Diversification does not ensure against loss
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1st Anniversary: Why Financial Models Are Essential for Retirement Strategies
Tony Leonardi, Certified Financial Planner professional celebrates 1 year on YouTube! Recap strategies(Roth conversions, portfolios, longevity) & why financial models areessential—success rates, tax savings, legacy. Updated for lower 2026 rates.Free quiz + book: LeonardiFamilyWealthcare.com/quizBecause there IS a Smarter Way to Retire.
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Hearing Health & Retirement: The Health-Wealth Connection with Audiologist Dr. Lori Aleks
Tony Leonardi, CFP® interviews audiologist Dr. Lori Aleks onhow untreated hearing loss affects cognitive health, family communication, retirement quality, and costs.Learn prevention, testing, modern hearing aidtechnology, and why early action is a smart financial move for longevity.Contact Dr. Aleks: www.bestlifehearingcenter.com or (203) 735-4327. Free 2-min quiz + book:https://www.leonardifamilywealthcare.com/quiz 15-min review:https://calendly.com/anthony-leonardi-leonardifwc/15-minute-check-in-quick-questions-quick-answers Because there IS a Smarter Way to Retire. #HearingHealth #RetirementPlanning #HealthWealthConnection#HearingLoss #CognitiveDecline #HSAs
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Ep 53 | 5 Biggest Tax Updates for 2025 Filing in 2026
Tony Leonardi, CFP® covers 5 key tax updates for 2025 (filed2026): inflation-driven bracket creep, Medicare IRMAA increases, RMD & 10-year rule, $15M estate exemption, crypto reporting. Proactive moves like Roth conversions & QCDs to save thousands. Real stories. Free quiz + book:LeonardiFamilyWealthcare.com/quiz. Because there IS a Smarter Way to Retire.
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Generational Wealth Transfer: Protect Your Legacy From Tax Traps
Tony Leonardi, CFP® on the $7 trillion wealth transfer:estate tax shockers, gift headaches, capital gains, IRA income tax, and the 10-year rule. Proactive strategies: gifting, stepped-up basis, insurance. Real mistakes & triumphs. Free quiz + book: LeonardiFamilyWealthcare.com/quiz.Because there IS a Smarter Way to Retire.
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Build a Smarter Portfolio in 5 Steps: Modern Portfolio Theory & The Efficient Frontier
Diversification isn’t just “don’t put all your eggs in onebasket” — it’s Nobel Prize-winning math that can make your money work harder with less risk. In this week’s episode of A Smarter Way to Retire, we breakdown Modern Portfolio Theory, the Efficient Frontier, and how to build a portfolio that maximizes return for your risk level. Real client story: Dropped risk 33 % with the same expectedreturn. Listen now and see if your portfolio is efficient ↓ Take the free 2-min retirement quiz + get my book:https://www.leonardifamilywealthcare.com/quiz #ModernPortfolioTheory #EfficientFrontier#RetirementPlanning #ASmarterWayToRetire
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Optimal Portfolio Allocation: How Monte Carlo Finds Your Retirement Sweet Spot
Tony Leonardi, CFP® explores how Monte Carlo simulationshelp find the optimal portfolio allocation for higher Probability of Success.Discover the trade-off between Probability of Success and Safety Margin, why average returns aren't the whole story, and how to fix inefficient investments.Free quiz + book at LeonardiFamilyWealthcare.com/quizBecause there IS a Smarter Way to Retire.
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Ep 49 | Monte Carlo Simulations: Your Retirement’s Most Important Number
Tony Leonardi, CFP® dives deep into Monte Carlo simulations — the key metric that shows the % chance your money lasts as long as you do. Discover why volatility timing matters more than average returns, and the strategies to improve your Probability of Success. Free quiz + book: LeonardiFamilyWealthcare.com/quiz.Because there IS a Smarter Way to Retire.
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2025 Year in Review – Wins, Surprises, and What's Next in 2026
Tony Leonardi reviews 2025’s biggest wins (permanent TCJA rates, age-75 RMDs, market patience) and surprises (AI explosion, IRMAA hits, semi-retirementtrend).Listener favorites: RMD strategies, 3 buckets, Roth conversions. Peek at 2026: inflation, Medicare rises, estate tweaks. Free retirement readiness quiz + book:LeonardiFamilyWealthcare.com/quiz.
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Last-Chance 2025 Moves: 5 Things to Do Before December 31
We’re one week from Christmas and two weeks from New Year’s— the perfect time for a few quiet financial wins. Tony Leonardi, CFP® shares 5 last-chance 2025 moves you canstill make before the calendar flips: 1. Max out retirement contributions (401(k), IRA, backdoorRoth) 2. Harvest tax losses in taxable accounts 3. Make charitable gifts (and set up QCDs for 2026) 4. Double-check RMDs and inherited IRA deadlines 5. Review beneficiary designations These quick actions can save thousands in taxes and give youa stronger start to 2026. Take the free 2-minute retirement readiness quiz + getTony’s book instantly: https://LeonardiFamilyWealthcare.com/quiz Book a complimentary 15-minute review: https://calendly.com/anthony-leonardi-leonardifwc/15-minute-check-in-quick-questions-quick-answers Because there IS a Smarter Way to Retire. Subscribe for weekly insights that help families acrossConnecticut and nationwide keep more of what they’ve earned. #RetirementPlanning #YearEndMoves #TaxStrategy#RothConversion #FinancialFreedom
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The Silent Retirement Killer That Can Wipe Out $1.8 Million (Sequence of Returns Risk Explained)
You've saved diligently for decades. Built up $1.8 million or more. Done everything right. But there's ONE risk that can destroy your retirement in justa few years—and almost nobody talks about it.In this episode of A Smarter Way to Retire, I break down sequence of returns risk using a real client story that will change how you think about retirement planning forever.📊 What You'll Learn: • Why volatility flips from friend to foe the day you retire • How the same $1.8M portfolio can last until 95 OR run out at 82 (same returns, different sequence)• The exact math behind why one bad year early can cut 12+ years off your retirement • 5 proven strategies to protect your portfolio from sequence risk •Real results: How to reduce your failure rate from 22% to just 4%⏱️ TIMESTAMPS: 0:00 - Introduction: The retirementrisk nobody discusses 1:15 - The $1.8 million nightmare (real client story)4:30 - Why volatility becomes your enemy in retirement 7:45 - The math thatshould keep you up at night 10:20 - Solution #1: Build a safe cash bucket 11:45- Solution #2: Flexible spending rules 13:10 - Solution #3: Dynamic withdrawalstrategies 14:30 - Solution #4: Strategic allocation shifts 15:50 - Solution#5: Income annuities for essentials 17:25 - Real results with guardrails inplace 19:00 - Action steps you can take today🎁 FREE RESOURCES: 📋 Take my 2-Minute Retirement ReadinessQuiz + Get My Book Free: 👉 LeonardiFamilyWealthcare.com/quiz📅 Schedule a Free 15-MinuteConsultation: 👉 LeonardiFamilyWealthcare.com📚 RELATED VIDEOS: • Why Your IRAis the Worst Place to Die With Money: • How RMDs Can Destroy YourRetirement: • Building a Bear Market-Proof Portfolio: 💼 About Anthony Leonardi, CFP®:I'm a Certified Financial Planner™ professional based in Newtown, Connecticut,specializing in comprehensive retirement planning with a focus on tax efficiency, risk management, and sustainable income strategies.📍 Leonardi Family Wealthcare Newtown,Connecticut 📧 Contact: LeonardiFamilyWealthcare.com⚠️ IMPORTANT DISCLOSURE: This content is foreducational purposes only and should not be considered personalized investmentadvice. Every individual's financial situation is unique. Please consult with aqualified financial professional before making investment decisions.#RetirementPlanning #SequenceOfReturnsRisk #FinancialPlanning#RetirementIncome #CFP #WealthManagement #RetirementStrategy #401k #IRA#BearMarket #MarketVolatility #RetirementTips #FinancialFreedom #NewtownCT#Connecticut👍 If you found this valuable, pleaseLIKE and SUBSCRIBE for weekly retirement planning insights! 🔔 Hit the notification bell so younever miss an episode of A Smarter Way to Retire!
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Your 401(k)/IRA = BEST place to save, WORST place to retire or die
Your 401(k)/IRA = BEST place to save, WORST place to retire or die.Discover why half your lifetime withdrawals could go to taxes + Medicare surcharges, and the exact 5-move playbook we use to cut that bill dramatically.Real client stories + the 3-bucket framework that changes everything. Because there IS a Smarter Way to Retire.Why Your 401(k) and IRA Are the BEST Place to Save… and the WORST Place to Retire or DieMost retirees are shocked to learn that roughly 50¢ of every dollar that leaves their retirement accounts over the next 30+ years could go to federal taxes and Medicare surcharges — unless they act.In this episode Tony Leonardi, CFP® reveals: • The $2.4 million client story that exposes the hidden tax trap • Why the IRS becomes your silent partner in retirement • The simple 3-bucket framework that can save hundreds ofthousands (or more) • The exact 5-move playbook being used right now withfamilies nationwideTimestamps 00:00 – The shocking truth about your retirement accounts02:10 – Mike & Linda’s $2.4M wake-up call 07:40 – The 3-Bucket Framework explained 12:20 – The 5-Move Playbook in action 17:30 – John & Susan’s real results after 5 yearsTake the free 2-minute quiz + get Tony’s book: https://www.leonardifamilywealthcare.com/quizBook a complimentary 15-minute review: https://calendly.com/anthony-leonardi-leonardifwc/15-minute-check-in-quick-questions-quick-answersBecause there IS a Smarter Way to Retire.
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6 RMD Strategies That Save My Clients $100k+ (You’ll Wish You Knew #5 Sooner)
If RMDs are coming (or already here), these 6 moves can save you tens or even hundreds of thousands. Tony covers QCDs, the new age-75 Roth window,fill-the-bracket conversions, smart market timing, turning RMDs into tax-free legacy with life insurance, and NUA for company stock.#RMD #RothConversion #RetirementPlanning #TaxStrategy#ConnecticutFinancialPlanner
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Required Minimum Distributions: The Fundamentals Every Retiree Must Know
Turning 73 this year? Then Required Minimum Distributions are about to become a major part of your financial life—whether you're ready or not.I'm Tony Leonardi, CFP®, and in this episode of A Smarter Way to Retire, I'm breaking down everything you need to know about RMDs: what they are, when they start, how to calculate them, and the seven most common mistakes that can trigger a 25% penalty.IN THIS EPISODE:What RMDs are and why the IRS requires them (1:00)When RMDs start—and the December 31st birthday rule (5:00)The April 1st trap that creates a double RMD year (5:00)How to calculate your RMD step-by-step (9:00)The brutal 25% penalty for missing your deadline (12:00)Seven critical mistakes people make with RMDs (14:00)Real stories: John's $50K mistake, Sarah's forgotten 401(k), Mike's inherited IRA surprise (20:00)Your action plan based on your age (23:00)KEY TAKEAWAYS:✓ RMDs start at age 73 for most people✓ Your first RMD can be delayed until April 1—but this usually backfires✓ You CAN aggregate IRAs but CANNOT aggregate 401(k)s✓ Missing an RMD triggers a 25% penalty (reduced to 10% if corrected within 2 years)✓ If you're age 60-72, this is your golden planning windowI've been helping families with retirement planning for over 30 years, and I've seen people lose thousands from simple RMD mistakes. The good news? They're all 100% avoidable.RESOURCES MENTIONED:Free RMD Checklist: LeonardiFamilyWealthcare.comIRS Uniform Lifetime TableBook: A Smarter Way to Retire: 10 Steps Towards a Confident Financial FutureCOMING NEXT WEEK: Episode 2 - Advanced RMD Strategies: QCDs, tax planning, and how RMDs interact with Social Security and Medicare.If you found this helpful, please rate and review the show. It helps other people find this information when they need it most.Plan smart. Retire happy.CONNECT WITH TONY:Website: LeonardiFamilyWealthcare.comInstagram: @TonyLeonardiCFPBook: A Smarter Way to Retire (available on Amazon)Schedule a consultation: LeonardiFamilyWealthcare.comDISCLAIMER: This podcast is for educational and informational purposes only and should not be considered financial, tax, or legal advice. Every individual's situation is unique. Please consult with a qualified financial advisor, CPA, and attorney before making any financial decisions. Tony Leonardi is a registered investment advisor. Full disclosures available at LeonardiFamilyWealthcare.com.retirement planning, RMD, required minimum distributions, IRA, 401k, tax planning, financial planning, retirement mistakes, age 73, CFP, Tony Leonardi, Connecticut, retirement income, tax strategyBusiness > Investing
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Roth Conversions Deep Dive: The Complete Guide
Join Tony Leonardi, CFP® from Newtown, Connecticut, for a comprehensive Roth conversion masterclass recorded November 14, 2025. After celebrating his birthday with fresh pasta and steaks over the firepit, Tony delivers the deep dive you've been requesting.The Core Principle: Roth conversions only make sense if you anticipate being in a higher tax bracket in the future. Without a comprehensive financial model—your"crystal ball"—you're just guessing with six-figure decisions.Who Should Convert: Early retirees with low-income years before RMDs, people expecting tax rate increases, large IRA balances facing massive future RMDs, those leavingmoney to heirs in peak earning yearsWho Should Avoid Converting: Lower brackets in retirement, no cash for taxes, ACA subsidy recipients,near Medicare IRMAA thresholds ($103K single/$206K married), complex after-tax IRA basis situationsStep-by-Step Implementation (8 Steps): Financial modeling, conversion budget calculation, CPAcoordination, execution before Dec 31, tax payment strategy, estimated payments, five-year tracking, annual reviewsCritical Mistakes to Avoid: Converting without a plan, ignoring pro-rata rule, forgetting statetaxes, triggering IRMAA, thinking you can reverse, converting too much too fast, not having cash for taxesCurrent Context: Tax Cuts and Jobs Act made permanent by July 2025 bill, 7 weeks left toexecute 2025 conversions, Medicare IRMAA thresholds, ACA subsidy impactsListen on Spotify, Apple Podcasts, or YouTube.Visit LeonardiFamilyWealthcare.com for financial modeling and conversionanalysis, or download the 2025 Retirement Reset Checklist with Probability of Success Meter.
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Year-End Tax Planning: 5 Strategies Before December 31st
Join Tony Leonardi, CFP® from Newtown, Connecticut, for a birthday special recorded November 7, 2025. With eight weeks left in 2025, discover actionable year-end tax strategies that could save you thousands.What You'll Learn:-How the One Big Beautiful Bill changed 2025 taxes ($31,500 standard deduction, senior bonus deductions) -Tax loss harvesting to offset gains (including wash sale rule workarounds) -Roth conversion sweet spots in November (with critical compliance notes on aggregation and pro-rata rules) -Charitable giving optimization (QCDs up to $108K, bunching, donor-advised funds) -Capital gains bracket management to harvest gains at 0% rate -Quick year-end moves (401k, HSA, withholding, FSA)Current 2025 Tax Context:Standard deduction: $31,500 (married)/$15,750 (single)Senior bonus deduction available for 65+ with income limits0% capital gains up to $96,700 (married)/$48,350 (single)QCD limit: $108,000401(k) contribution: $23,500 ($34,750 for ages 60-63)Key StrategiesTax loss harvesting with real $40K gain offset exampleRoth conversion bracket management (22% vs 32% example)Donor-advised fund strategy that saved $90,0000% capital gains harvesting to reset cost basisListen on Spotify, Apple Podcasts, or YouTube.Visit LeonardiFamilyWealthcare.com for year-end tax planning sessions, ordownload the 2025 Retirement Reset Checklist with Probability of Success Meter.
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Required Minimum Distributions: The Halloween Special
Join Tony Leonardi, CFP® from Newtown, Connecticut, for aHalloween-themed deep dive into Required Minimum Distributions (RMDs). Recorded October 31, 2025, this episode unmasks common RMD mistakes, explains current rules, and reveals sweet strategies like Qualified Charitable Distributions.What You'll Learn:-2025 RMD rules: Age 73 for those born 1951-1959, age 75 for 1960+-Common mistakes that cost thousands (the double distribution trap, forgotten IRAs, inherited IRA changes)-How to calculate your RMD and why it increases each year-QCDs: Donate up to $108,000 tax-free to charity and satisfy your RMD-Roth conversion strategies to reduce future RMDs-The "first dollars out" rule and December 31st deadlinesCurrent Context:-25% penalty for missed RMDs (10% if corrected within 2 years)-Roth 401(k)s no longer require lifetime RMDs (as of 2024)-New inherited IRA rules take effect in 2025-QCD limit increased to $108,000 (indexed for inflation)Key Strategies:-Take first RMD by Dec 31 (not April 1) to avoid double distributions-Use QCDs before other withdrawals to maximize tax benefits-Convert to Roth between ages 59½-73 for tax savings-Aggregate IRA RMDs (but not 401(k) RMDs)Visit LeonardiFamilyWealthcare.com for the 2025 Retirement Reset Checklist with Probability of Success Meter, or book a complimentary consultation at LeonardiFamilyWealthcare.com/assessment.
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The Art of Diversification: Why Your S&P 500 Fund Might Not Be Enough
Join Tony Leonardi, CFP® from Newtown, Connecticut, fresh from his family vacation in Florence, Italy, as he explores why traditional diversification strategies may no longer work. Recorded October 22, 2025, this episode revealshow the S&P 500's concentration in just five tech giants creates hidden risks for retirement portfolios.Learn about sequence of returns risk—why the timing of market returns matters as much as average returns when you're taking withdrawals. Discover practical strategies including asset class diversification, internationalexposure, alternative income sources, and rebalancing techniques.Key Takeaways:-Why the S&P 500 now effectively represents only 50 stocks-How sequence of returns risk can derail retirement plans-Practical diversification strategies for today's market-Action steps to reduce portfolio concentrationCurrent Market Context:-S&P 500 at record 6,736 with 30% in five companies-Fed expected to cut rates to 3.50-3.75% by year-end-10-year Treasury yield at 4.27%Listen on Spotify, Apple Podcasts, or YouTube.Visit LeonardiFamilyWealthcare.com for resources including the 2025Retirement Reset Checklist with Probability of Success Meter, or book a complimentary consultation at LeonardiFamilyWealthcare.com/assessment.
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38
Legacy Planning: Pass Wealth Tax-Efficiently
Join Tony Leonardi, CFP® and author of A Smarter Way to Retire, as he explores legacy and estate planning strategies to pass wealth smoothly. Recorded in October 2025, this episode dives into how annual gifting ($19,000 exclusion), trusts, and other tools may help reduce taxes and probate costs. Learn why planning can support control over your assets and align with your goals, from business succession to philanthropy.Key Takeaways:Discover how gifting and trusts may support tax efficiency.Understand non-tax benefits like asset protection.Get started with a complimentary consultation.Listen on:SpotifyApple PodcastsYouTubeVisit LeonardiFamilyWealthcare.com or download the 2025 Retirement Reset Checklist for a Probability of Retirement Success meter. Subscribe and leave a review to join this journey!
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37
Healthcare Planning for a Long Retirement | Tony Leonardi, CFP®
Hey everyone, it’s Tony Leonardi, CFP®! Plan for healthcare costs with HSAs, Medigap, and our smart planning process. Get a no cost e-book or complimentary consultation at LeonardiFamilyWealthcare.com.#RetirementPlanning Goditi il podcast di questa settimana!
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36
Tax-Efficient Retirement: Save More with Roth & Gifting | Tony Leonardi, CFP®
Hey everyone, it’s Tony Leonardi, CFP®!Discover tax-efficient retirement strategies to keep more of your wealth. Learn Roth conversions, tax-loss harvesting, gifting ($19,000/person in 2025), and more with our smart planning software. Book a complimentary consultation or get a nocost e-book at LeonardiFamilyWealthcare.com! #RetirementPlanning #TaxStrategies
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35
Alternative Investments: Diversify Smart for a Confident Retirement
Hey, it’s Tony Leonardi, CFP®! Learn how alternative investments like real estate & gold may help reduce portfolio volatility. Get my no cost e-book at LeonardiFamilyWealthcare.com/ebookor book a complimentary assessment!#RetirementPlanning
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34
Longevity Planning: Retire to 100+ with Confidence | Tony Leonardi, CFP®
Hey everyone, it’s Tony Leonardi, CFP®! Plan for a 100+ retirement with healthcare ($315K+), HSAs, and long-term care strategies. Boost success to 90%+ with MoneyGuidePro. Get a no cost e-book or book a complimentary consultation at LeonardiFamilyWealthcare.com! #RetirementPlanning
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33
AI in Financial Planning: Boost Your Retirement Success
Join Tony Leonardi, CFP® and author of A Smarter Way to Retire, to explore how AI revolutionizes financial planning.From real-time scenario analysis to personalized insights, learn how AI-powered tools like MoneyGuidePro help you achieve your retirement goals. Visit LeonardiFamilyWealthcare.comfor a no cost e-book or to book a Complimentary Consultation.#RetirementPlanning #AI #CFP
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The Great Wealth Transfer: Plan Your Legacy | A Smarter Way to Retire Ep. 32
Join Tony Leonardi, CFP®, author of A Smarter Way to Retire,as he dives into the great wealth transfer—$84 trillion moving to younger generations by 2045. Learn how to plan your legacy with trusts, gifting, GRATs,QCDs, and more, using MoneyGuidePro to help ensure your retirement stays secure. Book a complimentary assessment at[LeonardiFamilyWealthcare.com](https://LeonardiFamilyWealthcare.com/?utm_source=podcast&utm_medium=youtube)and grab our 2025 Wealth Transfer Checklist. Subscribe for weekly retirementtips! #WealthTransfer #RetirementPlanning #CFP Tags: wealth transfer, legacy planning, retirement planning,MoneyGuidePro, trusts, gifting strategies, GRAT, QCD, donor-advised funds,family limited partnerships, CFP professional, high-net-worth retirement
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31
Tax Planning for Retirees
Anthony Leonardi, CFP®, reveals tax planning for retirees:Roth conversions, OBBBA’s $6,000 deduction, and MoneyGuidePro’s dynamic approach. Dow surged 850 points; markets mixed. Book a free assessment atLeonardiFamilyWealthcare.com/?utm_source=podcast&utm_medium=applepodcasts.Subscribe for weekly retirement insights! Next: great wealth transfer, September 5.
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30
New Schedule! Social Security Optimization & Market Update
Join Anthony Leonardi, CFP®, author of A Smarter Way to Retire, for the launch of our new weekly schedule, startingwith Social Security optimization. Learn how to maximize benefits, avoid tax pitfalls, and leverage spousal strategies, with insights from MoneyGuidePro.Plus, a market update: Dow, S&P, and NASDAQ dipped, but bonds shine. Bookyour free retirement assessment at LeonardiFamilyWealthcare.com to boost yourplan’s success. Next up: tax planning on August 29! Subscribe now.(?utm_source=podcast&utm_medium=audio)
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29
CPI Report, Apple’s AI, Tariffs, and Retirement Planning
Join Anthony Leonardi, CFP®, author of A Smarter Way to Retire, as he unpacks the July 2025 CPI report (headline CPI at 2.7%, core CPI at 3.1%), market swings, Apple’s AI push with Live Translation and a smarter Siri, and tariff tensions impacting stocks. Headline CPI tracks daily costs like gas, while core CPI signals long-term pressures like healthcare. Apple’s $500 billion AI investment drove a Nasdaq rally, but tariffs on India and the EU sparked volatility.Learn how to combat inflation with tax strategies,diversify investments, and stress-test your retirement with MoneyGuidePro.Book a consultation with Anthony Leonardi, CFP® professional, atCalendly.com/anthony-leonardi-leonardifwc and download the free 2025 Tax Planning Checklist at LeonardiFamilyWealthcare.com. Follow onInstagram/@TonyLeonardiCFP and Facebook/LeonardiFamilyWealthcare for tips.Subscribe for more retirement insights and plan smart to retire happy! Keywords: Retirement planning, CPI 2025, headline CPI, core CPI, Apple AI, tariffs, CFP professional
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28
Birth Rates, AI, Trade Deals, and Your Retirement Plan
Join Anthony Leonardi, CFP®, author of A Smarter Way to Retire, as he explores how declining U.S. birth rates, medical factors like infertility, AI-driven job changes, new trade deals boosting U.S. manufacturing, and China’s one-child policy shift could impact your retirement. The U.S. birth rate hit1.6 kids per woman in 2024, below the 2.1 replacement rate, partly due to health issues like obesity and environmental chemicals. AI’s cutting jobs but also creating new roles and boosting productivity. Trade deals are driving investments like $100 billion for U.S. chip factories, promising250,000–500,000 jobs. Learn how to plan for a shrinking workforce, economicuncertainty, and growth opportunities with MoneyGuidePro. First 10 Connecticutresidents booking in August 2025 get a free retirement plan with Anthony Leonardi, CFP® professional. Book at Calendly.com/anthony-leonardi-leonardifwc and download our free 2025 Tax Planning Checklist at LeonardiFamilyWealthcare.com.Follow us on Instagram/@TonyLeonardiCFP and Facebook/LeonardiFamilyWealthcarefor weekly tips.Subscribe for more insights and plan smart to retire happy! Keywords: Retirement planning, declining birth rate, medical factors, AI job losses, AI productivity, trade deals, China one-child policy, manufacturing uptick, CFP professional, Connecticut retirement
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27
U.S.-EU Trade Deal: Boost Your Retirement in 2025
The U.S.-EU trade deal, signed July 27, 2025, is a game-changer for your retirement! With 15% tariffs, $750B in energy sales, and $600B in business investments, it’s a blockbuster for energy and small-cap stocks. In this week’s A Smarter Way to Retire, CFP Anthony Leonardi unpacks how to leverage this deal for your portfolio. From ExxonMobil’s 3% jump to inflation risks,learn how to:-Ride energy and small-cap ETFs for growth.-Save $2,000–$4,000 with 2025 tax rates.-Hedge inflation with bonds or real estate.-Diversify globally with caution.Ignore noise and plan smart with MoneyGuidePro.Download our free 2025 Tax Planning Checklist to help secure your future. Follow us onInstagram/@TonyLeonardiCFP or Facebook/LeonardiFamilyWealthcare for weeklytips. Ready to retire smarter? Schedule a consultation today!Sources: Reuters, Dow Jones, MarketScreener, Bloomberg, DW News, The Guardian,White House, Tax FoundationKeywords: U.S.-EU trade deal, retirement planning, tariffs 2025, energystocks, small-cap ETFs, inflation 2025Length: ~12 minutes
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26
2025 Markets: Tax Cuts, Tech, and Tariffs Shape Your Retirement
Markets hit record highs, and a U.S.-Japan trade deal sparked auto stocks, but tariffs and 2.7% inflation demand a plan.In this week’s A Smarter Way to Retire, CFP Anthony Leonardi breaks down this weeks economic moves, and the One Big Beautiful Bill Act’s impact on your retirement. From Nvidia’s AI surge to tariff revenue and consumer strength, learn how to:-Save $2,000–$4,000 with 24% and 32% tax rates.-Diversify to dodge tariff-driven tech dips (like Texas Instruments).-Protect against 2.7% inflation with real estate or bonds.-Leverage small caps boosted by the Japan deal and tariff revenue.-Ignore noise like Powell firing rumors and focus on real strategies. Download our free 2025 Tax Planning Checklist to secure your future. Follow us onInstagram/@TonyLeonardiCFP or Facebook/LeonardiFamilyWealthcare for weeklytips. Ready to retire smarter? Schedule a consultation today!Keywords: One Big Beautiful Bill Act, tax cuts 2025, retirementplanning, tariffs 2025, inflation 2025, AI stocksLength: ~5 minutes
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25
Tax Cuts & Market Moves: Boost Your Retirement in 2025
New tax cuts save you thousands! Learn how markets & the One Big Beautiful Bill Act impact your retirement. Get our free 2025 Tax Planning Checklist! #TaxCuts2025The One Big Beautiful Bill Act (signed July 4, 2025) locks in tax cuts that could save you thousands a year, but markets are volatile. In this week’s A Smarter Way to Retire, CFP Anthony Leonardi unpacks the latesteconomic news (July 7–14, 2025) and its impact on your retirement. From 35% tariffs on Canada (and new 30% threats on Mexico/EU) to a 2.7% inflation spike, we cover the risks—like higher costs squeezing your budget—and opportunities,like tariff revenue and tax-driven economic growth boosting your portfolio.Learn how to:-Save thousands with permanent 24% and 32% tax rates.-Stress-test your portfolio for tariffs and inflation with MoneyGuidePro.-Leverage the 23% Section 199A deduction for businesses or rentals.-Ride GDP growth from tax cuts for stronger stock returns.-Ignore rumors like Operation Chrysalis and focus on real strategies.Download our free 2025 Tax Planning Checklist to maximize savings and protectyour retirement. Follow us on Instagram/@TonyLeonardiCFP or Facebook/LeonardiFamilyWealthcare for more tips.Ready to retire smarter?Schedule a consultation with Leonardi Family Wealthcare today!
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24
One Big Beautiful Bill Act Episode
New tax law alert! The One Big Beautiful Bill Act could save you thousands in 2025. Join CFP Anthony Leonardi to learn how lower rates, a $6,000 senior deduction, and a 23% business break impact your retirement. Download our free 2025 Tax Planning Checklist at LeonardiFamilyWealthcare.com!#RetirementPlanning #TaxTipsThe One Big Beautiful Bill Act, signed July 4, 2025, is shaking up taxes for retirees and business owners. In this episode of A Smarter Way to Retire, CFP Anthony Leonardi breaks down how this law’s permanent 24% and 32% tax rates, $40,000 SALT cap, 23% Section 199A deduction, and $6,000 senior deduction can save you $2,000–$11,000 a year. But withphase-outs and a $3.5T deficit, you need to act fast! Learn actionable strategies to maximize savings, protect your portfolio, and plan your legacy.Download our free 2025 Tax Planning Checklist at LeonardiFamilyWealthcare.comand follow @TonyLeonardiCFP on Instagram/X for more tips. Subscribe to retire smarter!Sources: Ways and Means Committee, Congress.gov, Tax Foundation
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23
Financial Independence: Your 4th of July Retirement Goal
Join Tony Leonardi, CFP® from Newtown, Connecticut, on A Smarter Way to Retire for an episode recorded July 04, 2025. Celebrate America’s 249th with insights on financial independence amidst a Fed rate cut hint (20% Julychance), oil dropping to $68.9-$70, and S&P 500 highs. Learn how a plan counters PCE (0.1% rise), jobless claims, and the 2025 TCJA sunset, while boosting health.Key Takeaways:-Plan for independence amid market shifts.-Optimize taxes before the 2026 rate hike.-Stay active to enhance financial freedom.Listen on:SpotifyApplePodcastsYouTubeVisit LeonardiFamilyWealthcare.com or download the 2025Retirement Reset Checklist for a Probability of Retirement Success meter. Subscribe and review to join this journey.
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22
The Critical Need for a Retirement Financial Plan
The Critical Need for a Retirement Financial PlanJoin Tony Leonardi, CFP® from Newtown, Connecticut, on A Smarter Way to Retire for an episode recorded June 25, 2025. As summer heats up, discover why the number one retirement mistake—retiring without a plan—can lead tooverspending, underspending, risky investments, or missed tax savings. With the Fed holding rates steady despite 2.7% inflation and oil prices swinging ($85-$90) due to Iran-Israel tensions, Tony explains how a financial model safeguards your future.Learn to stress-test your plan and reduce financialstress linked to faster aging.Key Takeaways: Avoid overspending or underspending with a roadmap.Balance risk and seize tax savings with planning.Review annually amid economic shifts.Listen on:SpotifyApple PodcastsYouTubeVisit LeonardiFamilyWealthcare.com or download the 2025Retirement Reset Checklist for a Probability of Retirement Success meter. Subscribe and review tosupport this journey!
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ABOUT THIS SHOW
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
HOSTED BY
Anthony Leonardi
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