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Hey everyone, it’s Tony Leonardi, CFP® and founder of Leonardi Family Wealthcare. As a Certified Financial Planner® with over 25 years of experience helping high-net-worth families and retirees build confident financial futures, I’m passionate about simplifying complex topics like retirement planning, tax strategies, healthcare costs, and legacy building. I earned my CFP® marks on September 21, 1998, and have renewed them every two years since, staying at the forefront of fiduciary advice.

This blog is your go-to resource for practical insights drawn from real client stories and our comprehensive planning process. Whether you’re navigating Roth conversions, mitigating sequence of returns risk, or optimizing for a 100+ retirement, I’ll break it down in digestible chunks—no jargon, just actionable steps to help ensure your wealth works for you and your loved ones.

Expect weekly posts on everything from diversification to estate strategies, plus tips from my book, *A Smarter Way to Retire - 10 Steps Towards a Confident Financial Future*. If you’re ready to dive deeper, grab my no-cost e-book at My Book: A Smarter Way to Retire  or book a complimentary consultation at Select a Date & Time - Calendly . Let’s plan smart and retire happy—subscribe below for updates!

 
 

 

Friday, May 15, 2026

If you don’t need your IRA for living expenses, it can become one of the most tax-inefficient assets to leave your children. Discover why the IRS often takes two bites at the same dollars and four practical strategies to pay tax once.

Friday, May 8, 2026

Most retirees never separate their Live On assets (money they’ll spend) from their Leave On assets (money for heirs). Learn why this mistake leads to higher taxes, more risk, and a smaller legacy — and discover four practical strategies

Friday, May 1, 2026

Most retirees treat all their retirement accounts the same way. Discover the critical difference between Live On assets (money you’ll spend) and Leave On assets (money for your heirs). Learn how to calculate the split

Friday, April 24, 2026

Many retirees don’t need their RMD income, yet the IRS can take two bites at the same IRA dollars. Discover the Smart Retirement Tax Shield and Smart Legacy Tax Shield — two powerful strategies to pay tax once instead of twice!

Friday, April 17, 2026

How do you turn your savings into reliable retirement income that lasts? Tony Leonardi, CFP® breaks down the best retirement income solutions for 2026 — including buckets, protected income layers, guardrails, and blending sources.

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Monday, April 6, 2026

Q1 2026 Webinar recap: Tony Leonardi, CFP® shares 5 powerful tax strategies including asset location, tax-efficient withdrawals, QCDs, Roth conversions, and tax-loss harvesting. Learn how to lower your tax bill and preserve more.

Friday, March 27, 2026

Living past 95 is more common than ever, but healthcare costs can reach $315k+. Tony Leonardi, CFP® explains why old rules fail, how HSAs and annuities help, and how modeling boosts success rates. Free Roth Playbook inside.

Friday, March 20, 2026

Sequence of returns risk can cut your retirement success rate by 50% if markets dip early. Tony Leonardi, CFP® explains how to use AI modeling, income floors, and annuities for tax-efficient retirement and confident income planning.

Friday, March 13, 2026

RMDs in 2026 can quietly inflate taxes and erode your savings. Tony Leonardi, CFP® explains how to use QCDs, Roth conversions, and modeling to stay under IRMAA thresholds, reduce lifetime taxes by 20–30%, and preserve more for your family.

Friday, March 6, 2026

Considering Roth conversions in 2026? Tony Leonardi, CFP® explains how to pay taxes now at low rates to avoid higher brackets later. Learn timing, modeling, real examples, and why it's not one-size-fits-all.

Friday, February 27, 2026

Tony Leonardi, CFP® kicks off Year 2 with a deep dive on financial modeling—your tool for probability of success, Roth conversions, portfolio optimization & more. Avoid guessing; build confidence for any age.

Friday, February 20, 2026

Celebrate our 1st YouTube anniversary! Tony Leonardi, CFP® reflects on key strategies: Roth conversions, portfolio optimization, RMD planning. Discover why a financial model (with Monte Carlo) is essential for any age

Friday, February 13, 2026

Tony Leonardi, CFP® interviews audiologist Dr. Lori Aleks on how untreated hearing loss affects cognitive health, family dynamics, retirement quality, and costs. Learn prevention, baseline testing and hearing aid options.

Friday, February 6, 2026

Tony Leonardi, CFP® explains longevity risk – outliving your savings – and how to prevent it. Stress-test models, Monte Carlo simulations, 5 strategies like annuities & HSAs. Real story: Boosted success to 95% at age 100.

Friday, January 30, 2026

Tony Leonardi, CFP® covers 5 key tax updates for 2025 filing in 2026: bracket creep, Medicare hikes, RMDs, estate exemptions, crypto reporting. Save thousands with proactive moves like Roth conversions and QCDs.

Friday, January 23, 2026

Tony Leonardi, CFP® reveals hidden tax traps in generational wealth transfer: estate taxes, gift rules, capital gains, IRA income tax, and the 10-year rule. Proactive strategies: gifting, stepped-up basis, insurance.

Friday, January 16, 2026

Tony Leonardi, CFP® explains Modern Portfolio Theory, the Efficient Frontier, and Nobel Prize-winning ideas from Markowitz & Sharpe. Learn how to build an efficient portfolio that maximizes return for your risk level.

Friday, January 9, 2026

Tony Leonardi, CFP® explores how Monte Carlo simulations help find the optimal portfolio allocation for higher Probability of Success. Discover the trade-off between Probability of Success and Safety Margin

Friday, December 19, 2025

With 2025 ending soon, Tony Leonardi, CFP® shares 5 quick year-end moves: max retirement contributions (including backdoor Roth), harvest tax losses, make charitable gifts, check RMDs, and update beneficiaries. Save taxes, start 2026 strong

Tuesday, December 16, 2025

Sequence of returns risk can wipe out decades of retirement savings in just a few years. Learn why market timing matters more than average returns and discover 5 proven strategies to protect your portfolio from this silent killer.

Thursday, December 11, 2025

Your 401(k) & IRA are the best place to save while working — but the worst place to retire or die. Discover the hidden tax trap and the 5-move playbook that can save families six figures or more. Because there IS a Smarter Way to Retire.

Friday, November 28, 2025

If you’re taking Required Minimum Distributions (RMDs), you already know they can create a tax tsunami in retirement. The good news? There are six legal, IRS-approved strategies that can dramatically reduce — or even eliminate — the tax

Monday, November 24, 2025

Tony Leonardi, CFP®, breaks down RMDs: rules, calculations, and 7 costly mistakes. Learn when they start (73 or 75), penalties (25%), and fixes like aggregation. Avoid the double-dip and forgotten 401(k) traps!

Thursday, November 20, 2025

Tony Leonardi, CFP®, delivers a comprehensive Roth conversion guide: only convert if you'll be in higher tax brackets later. Learn who should (and shouldn't) convert, step-by-step implementation, and critical mistakes to avoid.

Monday, November 3, 2025

Tony Leonardi, CFP®, demystifies RMDs with Halloween fun. Learn the 2025 rules (age 73 start), avoid costly mistakes, and discover QCDs ($108K limit) that cut taxes. Visit LeonardiFamilyWealthcare.com/assessment for help!

Friday, October 17, 2025

Tony Leonardi, CFP®, shares legacy planning tips from Florence, Italy. Learn to pass wealth tax-efficiently with gifting, trusts, and more, avoiding probate. Book a free consultation at LeonardiFamilyWealthcare.com/assessment!

Friday, October 10, 2025

Tony Leonardi, CFP® shares 5 healthcare planning strategies: HSAs, Medigap, more. Plan for $315K+ costs with our planning process. Get no cost e-book or complimentary consult at LeonardiFamilyWealthcare.com! #RetirementPlanning

Friday, October 3, 2025

Tony Leonardi, CFP® shares tax-efficient retirement strategies: Roth conversions, tax-loss harvesting, gifting. Save more with smart planning. Get no cost e-book or complimentary consultation at LeonardiFamilyWealthcare.com

Friday, September 26, 2025

Tony Leonardi, CFP® explores alternative investments for retirees. Learn how real estate, private equity, and gold can help reduce volatility with low correlation. Book a complimentary assessment or get a no cost e-book.

Tuesday, September 23, 2025

Tony Leonardi, CFP® on longevity planning for 100+ retirement. Learn healthcare costs ($315K+), HSAs, long-term care, Medicare. Boost success to 90%+ with smart modeling. Get no cost e-book or complimentary consultation.

Monday, September 15, 2025

Join Tony Leonardi, CFP® to explore AI in financial planning. Learn how MoneyGuidePro boosts retirement success with real-time analysis. Get a no cost e-book or Complimentary Assessment at LeonardiFamilyWealthcare.com.

Saturday, September 6, 2025

Tony Leonardi, CFP®, explores the $84T wealth transfer. Plan your legacy with trusts, $19K gifting, GRATs, QCDs, & FLPs using MoneyGuidePro. Book a complimentary assessment at LeonardiFamilyWealthcare.com to secure your retirement & legacy!

Friday, August 29, 2025

Save on taxes in retirement! Anthony Leonardi, CFP®, shares Roth conversion strategies and the OBBBA deduction. Markets mixed after Dow’s 850-point surge. Book a free assessment!

Monday, August 25, 2025

New podcast schedule! Learn Social Security strategies to boost retirement income and avoid tax pitfalls. Markets dipped, but bonds shine. Book a free assessment with Anthony Leonardi, CFP®.

Friday, August 22, 2025

Markets are buzzing with optimism—stocks hit record highs last week, with the S&P 500 and Nasdaq climbing on hopes of Federal Reserve rate cuts, per Investopedia. But with core inflation at 3.1% and tariff tensions looming, per the...

Monday, August 18, 2025

July 2025 CPI: 2.7% headline, 3.1% core. Apple’s $500B AI push and tariffs shake markets. Anthony Leonardi, CFP®, shares tips to protect your retirement. Book a consult and get the 2025 Tax Checklist! #RetirementPlanning

Friday, August 8, 2025

U.S. birth rate drops to 1.6, AI cuts jobs but boosts GDP, trade deals spark manufacturing. Tony Leonardi, CFP®, shows how to plan retirement amid these shifts. Free plan for 10 CT residents! Book Calendly.com/anthony-leonardi-leonardifwc

Friday, July 18, 2025

Are you planning for a secure retirement? The economy is buzzing, and the One Big Beautiful Bill Act (signed July 4, 2025) is shaking things up with permanent tax cuts that could boost your financial future. In this week’s A Smarter...

Friday, July 4, 2025

Celebrate financial independence this 4th of July! Tony Leonardi, CFP® from Newtown, CT, shares how a plan navigates Fed rate hints, oil at $68.9-$70, and S&P 500 highs amid TCJA sunset. Visit LeonardiFamilyWealthcare.com!

Monday, June 30, 2025

Retiring without a plan risks overspending, underspending, risky investments, or tax losses. Tony Leonardi, CFP® from Newtown, CT, explains how a financial model safeguards your retirement amid Fed rate holds and oil volatility.

Monday, June 2, 2025

From Memorial Day reflections to the S&P 500’s 23% trough-to-peak gain (now 5,921.54), your progress matters. Yesterday’s 2.05% rally shows resilience, but volatility persists. Stay focused on long-term goals, not short-term headlines.

Wednesday, May 28, 2025

Retirement planning isn’t just about saving and investing; it’s about ensuring your money lasts as long as you do. Many assume they’re set for retirement, but without measuring your probability of success, you might miss critical risks.

Friday, May 23, 2025

As we embrace spring here in Fairfield County, Connecticut, I’m Tony Leonardi, a CFP® professional serving clients across multiple states. This week, with Memorial Day approaching on May 26, I’ve been reflecting on family and...

Wednesday, May 21, 2025

Does your portfolio align with your financial model? Is it diversified, cost-efficient, and tax-efficient? Does it deliver the return you need without excessive risk? If you’re unsure, a professional portfolio review can uncover hidden risk

Friday, May 16, 2025

Navigate market volatility with 3 positive updates for May 2025. Tony Leonardi, CFP® from Fairfield County, CT, covers the US-UK trade deal, US-China agreement, & bipartisan drug pricing cuts. Learn why data beats headlines for retirees.

Thursday, May 15, 2025

When it comes to investing, you’ve likely heard the phrase “no risk, no reward.” While there’s truth to that, taking on too much risk can lead to sleepless nights and emotional decisions that derail your financial future.

Monday, May 12, 2025

Discover 2025 retirement income sources with Tony Leonardi, CFP® professional. Learn about Social Security, pensions, investments, and more. Sign up for our free 2025 Retirement Reset Checklist at https://www.leonardifamilywealthcare.com

Friday, May 9, 2025

Save thousands with 2025 tax-smart retirement moves from Tony Leonardi, CFP® professional. Learn Roth conversions, QCDs, and more. Sign up for our free 2025 Retirement Reset Checklist at https://www.leonardifamilywealthcare.com

Monday, May 5, 2025

Retirement isn’t just about leaving your job—it’s about building the life you’ve worked hard to create. That’s why setting clear “retirement goals” is a cornerstone of smart retirement planning. Without a roadmap, it’s easy to feel lost

Wednesday, April 30, 2025

Build a confident 2025 retirement plan with Tony Leonardi, CFP® professional’s 10-step process. From organizing finances to adjusting risk, this recap connects it all. Sign up for your free 2025 Retirement Reset Checklist

Monday, April 21, 2025

When do you want to retire? It’s one of the biggest questions in retirement planning, but it’s not just about picking a date. In step four of my book, *A Smarter Way to Retire: 10 Steps Toward a Confident Financial Future*, we explore...

Thursday, April 17, 2025

April 15th—Tax Day—is here, and whether you’re celebrating a refund or wincing at a bill, taxes are on everyone’s mind. But have you ever wondered how the federal income tax started, how...

Tuesday, April 15, 2025

Retirement is more than just a financial milestone—it’s a deeply personal transition filled with hopes, dreams, and, yes, a few worries. In step three of my book, A Smarter Way to Retire: 10 Steps Toward a Confident Financial Future,...

Thursday, April 10, 2025

Retirement planning isn’t just about saving and investing—it’s about ensuring your money lasts as long as you do. Many people assume they’re financially set for retirement, but without measuring their probability of success, they could...

Wednesday, April 9, 2025

In recent discussions on economic policy, tariffs have taken center stage, particularly with President Trump’s proposed "Liberation Day" plan aimed at restructuring global trade. To understand the implications of such policies, we must...

Tuesday, April 8, 2025

Creating a solid financial plan is like planning a road trip—you need a map to get to your destination. That map is your financial model, a tool that gives you a clear picture of where you are today and helps you navigate toward your...

Wednesday, April 2, 2025

Planning for retirement can feel overwhelming, but the first and most crucial step is getting organized. Before you can build a solid financial plan, you need to understand exactly where you stand today.

Monday, March 31, 2025

A Smarter Way to Retire: Episode 1 Recap Welcome to the first episode of the A Smarter Way to Retire podcast! I’m Tony Leonardi, Certified Financial Planner, Chartered Retirement Planning Counselor, founder of Leonardi Family Wealthcare

Friday, March 28, 2025

At Leonardi Family Wealthcare, we believe retirement planning isn’t just about numbers—it’s about people, families, and the sense of security that comes from knowing you’re on the right path. Our mission is to help you navigate...