Relax, It’s Retirement Podcast

Are you worried about the impact of taxes in retirement? Concerned you might run out of money in retirement? Are you looking to avoid making costly pitfalls transitioning into retirement? Welcome to the Relax, It’s Retirement Podcast with Josh Leonard from Leonard Advisory Group. In this podcast, we help those nearing retirement greet it with a well prepared smile. Join Josh and his guests to learn the retirement and tax planning tips you need so that you too, can live your golden years with the happiness and excitement you deserve. Hear stories from his years of experience to help you transition into a fun and intentional retirement.

Episodes

Retire with Intent: The True Intent Planning System™ Explained (Ep. 96)

July 23, 2025 • 29 mins

Retirement isn’t just an end, it’s the beginning of everything you’ve always wanted to do. What if you could approach this next chapter with purpose and confidence, not just hope? In this episode, Josh Leonard breaks down the True Intent Planning System™ and its five pillars for a purposeful retirement. He emphasizes the importance of …

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How Recent Retirement Laws May Affect Your Future (Ep. 95)

July 2, 2025 • 30 mins

New laws have reshaped retirement planning, and staying informed could mean the difference between saving money and paying avoidable taxes. In this episode, Josh Leonard explains the impact of Secure Act 1.0 and 2.0 on retirement planning and why constant plan updates are necessary. He highlights how changes to RMD ages, IRA rules, and Medicare …

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Pine Valley Camp: Building Futures, One Child at a Time (Ep. 94)

June 11, 2025 • 49 mins

Retirement can be a time of reflection and purpose, where intentionality meets impact. What if your golden years were not just for relaxation but a journey to uplift others while enriching your own life? This episode reveals how retirement and service can harmoniously coexist. In this episode, Josh Leonard speaks with Matthew Reichart, Executive Director …

Can I Retire This Year? (Ep. 93)

May 21, 2025 • 26 mins

Market swings, inflation, and shifting headlines can make retiring this year feel uncertain. But with the right plan, you don’t need to delay your goals — even in a tough market. Are you prepared financially and mentally for what comes next? In this episode, Josh Leonard shares how to build a flexible retirement strategy that …

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Should You Buy, Lease, or Hold? Car Buying Decisions in Retirement (Ep. 92)

May 7, 2025 • 35 mins

Buying a car can be exciting, but it can also be financially confusing, especially as you enter retirement. How do you decide between leasing, buying new, or buying used? What financial factors should retirees consider before making a vehicle purchase? In this episode, Josh Leonard guides listeners through the key financial and personal considerations when …

Retirement Resilience: How to Protect Your Plan in a Volatile Market (Ep. 91)

April 15, 2025 • 22 mins

Worried about market volatility and what it means for your retirement? You’re not alone. Many people get anxious when their retirement accounts seem to shrink after years of growth. In this episode, Josh Leonard discusses market volatility and strategies to remain patient. Josh explains what market corrections are, why they happen, and how to prepare …

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Spring Clean Your Finances: 5 Essential Tips for a Fresh Start (Ep. 90)

April 1, 2025 • 27 mins

Are your finances due for a little spring cleaning? Just like airing out your home after winter, it’s time to dust off your financial strategy! Join Josh Leonard as he dives into five key tips for a fresh start this spring. He explores ways to tidy up old retirement accounts, refresh your financial planning outlook, …

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Avoiding the Good Saver Tax Problem with Proactive Planning (Ep. 89)

March 11, 2025 • 20 mins

Could saving smart lead to a tax nightmare? Join Josh Leonard as he unravels the unexpected “Good Saver Tax Problem” that even the most prepared might face. Josh explores strategies to sidestep surprise tax burdens during retirement. Dive into proactive approaches like phase-based tax stacking and unravel the complexities of Roth conversions, Required Minimum Distributions …

Unpacking Social Security Changes (Ep. 88)

February 18, 2025 • 19 mins

Social Security remains a critical foundation for retirement, but recent changes bring new opportunities and challenges for retirees. What strategies can maximize your Social Security benefits? How do recent legislative changes impact your retirement income plan? In this episode, Josh Leonard explains the updates to Social Security regulations, including the removal of provisions like WEP …

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Planning Ahead for Retirement (Ep. 87)

February 4, 2025 • 32 mins

Retirement should be a time of fulfillment, not financial stress, yet many retirees face unexpected challenges. How can you make decisions today that your future self will thank you for? What steps can you take to avoid common retirement regrets and financial pitfalls? In this episode, Josh Leonard and Pete Belcastro discuss essential retirement planning …

Conquering Retirement Fears with Confidence (Ep. 86)

January 21, 2025 • 25 mins

Retirement is a time for celebration, but it often brings up important concerns about money, health, and purpose. How can you prepare to enjoy this new chapter with peace of mind? In this episode, Josh Leonard and Pete Belcastro discuss actionable steps to overcome common retirement fears, from financial security to finding joy and meaning …

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The Diversification Dilemma: Are Your Investments Really Safe? (Ep. 85)

January 14, 2025 • 30 mins

Diversification isn’t just a buzzword—it’s a critical tool for protecting your retirement savings and future security. This week, Josh Leonard and Pete Belcastro tackle common misconceptions about diversification and share actionable insights on creating a retirement plan that minimizes risk and maximizes opportunities. From portfolio strategies to tax diversification and financial tools, this episode has …

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Mastering the Tax Triangle (Ep. 84)

January 7, 2025 • 23 mins

What do taxes and retirement have in common with your happiest Saturday? In this episode of Relax, It’s Retirement, Josh Leonard invites you to unravel the often confusing world of taxes as you approach your golden years. He dives into the “tax triangle” strategy, offering a simplified perspective on how to categorize your assets for …

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The Five Worlds of Money in Retirement (Ep. 83)

December 31, 2024 • 22 mins

Are you prepared for the five worlds of money in retirement? In this episode of “Relax, It’s Retirement,” Josh Leonard explores the distinct but interconnected areas crucial to a successful retirement plan. He dives into income planning, investment strategies, the importance of health and legacy planning, and of course, those pesky taxes. With real-life examples …

Setting Goals for a Purposeful Retirement (Ep. 82)

December 24, 2024 • 27 mins

Goal setting isn’t just for your career—it’s essential for creating an intentional and fulfilling retirement. What goals will keep you engaged, active, and satisfied as you transition to this next chapter? How do you plan for a successful financial and personal journey during retirement? In this episode, Josh Leonard recaps his personal and professional goals …

Making the Most of Holiday Giving in Retirement (Ep. 81)

December 17, 2024 • 27 mins

Giving is a joyful part of the holiday season, and retirement offers unique opportunities to make it meaningful. How can retirees balance financial, personal, and charitable giving during the holidays? How can creative and intentional choices enhance the spirit of giving? In this episode of Relax, It’s Retirement, Josh Leonard and Pete Belcastro discuss strategies …

What Kills a Bull Market? Factors that Could Trigger the Next Recession (Ep. 80)

December 10, 2024 • 31 mins

What happens when market emotions take over your retirement planning? Josh Leonard and Pete Belcastro tackle the rollercoaster ride of market trends and how you can prepare for those inevitable twists and turns. They explore the intricacies of bull and bear markets and how these fluctuations impact your financial strategies for retirement. They discuss critical …

The Best Moments: Top Retirement Insights from The Relax, It’s Retirement Podcast! (Ep. 79)

December 3, 2024 • 29 mins

Retirement planning can feel overwhelming, but the right strategies can make it smooth and intentional. How do you structure finances to ensure your money lasts while enjoying the lifestyle you want? This episode compiles the best retirement advice moments from Josh Leonard and his team, covering vital tips to plan your golden years with confidence. …

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Know What You Owe: Essentials for a Secure Retirement (Ep. 78)

November 26, 2024 • 31 mins

Are you aware of what you truly owe, and more importantly, own in your financial portfolio? Join us in this episode of Relax, It’s Retirement, where Josh Leonard and Pete Belcastro dive into the nitty-gritty of financial awareness and planning. Do you really understand how balancing debts and assets can pave a way for a …

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5 Key Tax Opportunities to Capture Before Year-End! (Ep. 77)

November 19, 2024 • 24 mins

Are you making the most of your year-end tax planning? In this episode, Josh Leonard dives into effective year-end tax planning strategies to maximize your savings. Prepare for an insightful discussion on Roth conversions, tax loss harvesting, and charitable giving. Learn how to navigate potential tax pitfalls and make informed financial decisions before the calendar …

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Relax, It’s Retirement Podcast

Episodes

.css-14f5ked{margin:0;word-break:break-word;display:-webkit-box;-webkit-box-orient:vertical;box-orient:vertical;-webkit-line-clamp:2;overflow:hidden;}Retire with Intent: The True Intent Planning System™ Explained (Ep. 96)

.css-r6mb8g{margin:0;word-break:break-word;display:-webkit-box;-webkit-box-orient:vertical;box-orient:vertical;-webkit-line-clamp:1;overflow:hidden;}How Recent Retirement Laws May Affect Your Future (Ep. 95)

Pine Valley Camp: Building Futures, One Child at a Time (Ep. 94)

Can I Retire This Year? (Ep. 93)

Should You Buy, Lease, or Hold? Car Buying Decisions in Retirement (Ep. 92)

Retirement Resilience: How to Protect Your Plan in a Volatile Market (Ep. 91)

Spring Clean Your Finances: 5 Essential Tips for a Fresh Start (Ep. 90)

Avoiding the Good Saver Tax Problem with Proactive Planning (Ep. 89)

Unpacking Social Security Changes (Ep. 88)

Planning Ahead for Retirement (Ep. 87)

Conquering Retirement Fears with Confidence (Ep. 86)

The Diversification Dilemma: Are Your Investments Really Safe? (Ep. 85)

Mastering the Tax Triangle (Ep. 84)

The Five Worlds of Money in Retirement (Ep. 83)

Setting Goals for a Purposeful Retirement (Ep. 82)

Making the Most of Holiday Giving in Retirement (Ep. 81)

What Kills a Bull Market? Factors that Could Trigger the Next Recession (Ep. 80)

The Best Moments: Top Retirement Insights from The Relax, It’s Retirement Podcast! (Ep. 79)

Know What You Owe: Essentials for a Secure Retirement (Ep. 78)

5 Key Tax Opportunities to Capture Before Year-End! (Ep. 77)

Popular Podcasts

Retire with Intent: The True Intent Planning System™ Explained (Ep. 96)

How Recent Retirement Laws May Affect Your Future (Ep. 95)