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/quiz

Because there IS a Smarter Way to Retire. 

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.

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.

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

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!

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 Die

Most 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 nationwide

Timestamps

00:00 – The shocking truth about your retirement accounts

02:10 – 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 years

Take the free 2-minute quiz + get Tony’s book: https://www.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.

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

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 window

I'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.com
• IRS Uniform Lifetime Table
• Book: A Smarter Way to Retire: 10 Steps Towards a Confident Financial Future

COMING 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.com
• Instagram: @TonyLeonardiCFP
• Book: A Smarter Way to Retire (available on Amazon)
• Schedule a consultation: LeonardiFamilyWealthcare.com

DISCLAIMER: 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 strategy

Business > Investing

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 years

Who 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 situations

Step-by-Step Implementation (8 Steps): Financial modeling, conversion budget calculation, CPAcoordination, execution before Dec 31, tax payment strategy, estimated payments, five-year tracking, annual reviews

Critical 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 taxes

Current Context: Tax Cuts and Jobs Act made permanent by July 2025 bill, 7 weeks left toexecute 2025 conversions, Medicare IRMAA thresholds, ACA subsidy impacts

Listen 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.

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 limits
• 0% capital gains up to $96,700 (married)/$48,350 (single)
• QCD limit: $108,000
• 401(k) contribution: $23,500 ($34,750 for ages 60-63)

Key Strategies

• Tax loss harvesting with real $40K gain offset example
• Roth conversion bracket management (22% vs 32% example)
• Donor-advised fund strategy that saved $90,000
• 0% capital gains harvesting to reset cost basis

Listen 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.