Josh Leonard

Relax, It’s Retirement Podcast

Business EN ↓ 112 episodes

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 transit...

Author

Josh Leonard

Category

Business

Latest episode

Jul 8, 2026

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Episodes

Conquering Retirement Fears with Confidence (Ep. 86) 21.01.2025

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 beyond work. Whether it’s optimizing Social Security, man...

The Diversification Dilemma: Are Your Investments Really Safe? (Ep. 85) 14.01.2025

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 epi...

Mastering the Tax Triangle (Ep. 84) 07.01.2025

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 better tax efficiency.  Josh shares tips on n...

The Five Worlds of Money in Retirement (Ep. 83) 31.12.2024

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 and practical ti...

Setting Goals for a Purposeful Retirement (Ep. 82) 24.12.2024

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 while emphasizing the importance of in...

Making the Most of Holiday Giving in Retirement (Ep. 81) 17.12.2024

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 for embracing the joy of gi...

What Kills a Bull Market? Factors that Could Trigger the Next Recession (Ep. 80) 10.12.2024

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 indicators that can predict a market...

The Best Moments: Top Retirement Insights from The Relax, It’s Retirement Podcast! (Ep. 79) 03.12.2024

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.  From managing taxes to healthcare planning, th...

Know What You Owe: Essentials for a Secure Retirement (Ep. 78) 26.11.2024

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 secure retirement? They explore the significance of knowing your financial l...

5 Key Tax Opportunities to Capture Before Year-End! (Ep. 77) 19.11.2024

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 flips to a new year. Josh co...

How to Safeguard Your Identity in Retirement (Ep. 76) 12.11.2024

Are you protecting yourself from the growing threat of identity theft, especially as you near retirement? This week on Relax, It’s Retirement, Josh Leonard sits down with Angela Ferrante, Leonard Advisory Group’s in-house expert on identity theft, to shed light on this pressing issue. They delve into the methods used by scammers to target older Americans and discuss practical steps you...

Managing Job Loss on the Path to Retirement (Ep. 75) 05.11.2024

What happens when an unexpected job loss disrupts your retirement plans?  In this episode of Relax, It’s Retirement, Josh Leonard and Pete Belcastro delve into strategies for navigating the economic and emotional turbulence of being laid off near retirement.  They offer essential tips on managing finances, addressing healthcare needs, and maintaining a positive outlook during this challenging tran...

Financial Planning Strategies to Avoid Costly Mistakes (Ep. 74) 29.10.2024

Feeling empowered in retirement requires careful planning to avoid unnecessary costs and maximize enjoyment.  Are you prepared to handle debt, taxes, and big life changes in retirement?  Learn how financial strategies can help you manage taxes, pay down debt, and even enjoy your golden years worry-free. In this episode of Relax, It’s Retirement Josh Leonard and Pete Belcastro dive into the w...

Maximizing Charitable Giving in Retirement (Ep. 73) 22.10.2024

Charitable giving can be a powerful part of your retirement, and it’s about more than just donations—it’s about making a lasting impact with your finances. How do you ensure your giving is intentional and efficient? What strategies can help you make the most of your contributions without incurring unnecessary taxes? Join Josh Leonard and Pete Belcastro as they dive into the fulfilling...

Key Strategies to Maximize Your Medicare Benefits (Ep. 72) 15.10.2024

When was the last time your reviewed your Medicare plans? In this episode of *Relax It’s Retirement*, host Josh Leonard sits down to discuss the ins and outs of Medicare open enrollment. As the leaves turn and the air gets crisper, it’s the perfect time to cozy up and ensure you’re prepared for the year ahead. With open enrollment running from October 15th to December 7th, this discussion is...

Market Shifts: How to Stay Informed and Prepared (Ep. 71) 08.10.2024

As inflation cools, new questions arise about the market’s direction and future economic trends. How will the Fed’s decisions on interest rates affect your investments? Can the economy withstand reduced inflation without entering a recession? This week, Josh Leonard and Pete Belcastro dive into the significant shift of investor concerns from inflation to other economic factors, highlig...

Overcoming Retirement Fears During Election Season (Ep. 70) 01.10.2024

Election seasons often bring a wave of anxiety, especially for those nearing retirement. How do you prepare for potential economic shifts without succumbing to fear? How can you ensure your retirement plan remains robust regardless of political outcomes? In this episode of Relax, It’s Retirement, Josh Leonard explores how the election results could potentially affect your financial future, a...

Capital Loss Harvesting vs. Capital Gain Harvesting: What’s Right for Your Retirement? (Ep. 69) 24.09.2024

Are you maximizing the potential of capital gains and losses in your retirement planning? This week, Josh Leonard and Pete Belcastro dive into the often-overlooked strategies of capital gain and loss harvesting. You’ll learn the essential differences between capital loss and capital gain harvesting, why timing and tax brackets play a crucial role in your financial planning, and how these str...

Putting Time on Your Side in Retirement (Ep. 68) 17.09.2024

Time can still be on your side even in retirement! In this episode, Josh dives into the fascinating dynamics of time and retirement planning. You’ll learn how to maximize your retirement years by leveraging the power of compounding interest, making strategic investment decisions, and using financial tools like annuities and HSAs to ensure your money lasts. Join us as we explore practical str...

6 Ways to Travel on a Budget in Retirement (Ep. 67) 10.09.2024

Ready to make your dream retirement travel a reality without breaking the bank? In this episode, Josh Leonard guides you through six effective strategies for budget-friendly travel during retirement. Learn why flexibility is crucial, how to use points and miles effectively, and the surprising alternatives to traditional accommodations. This is your roadmap to financially savvy and fulfilling trave...

Overcoming Obstacles With Grit, Endurance & Family Support (Ep. 66) 03.09.2024

Are you ready to hear a story about grit, teamwork, and the unexpected turns that can define your journey, whether it’s a race or your retirement plan? In this episode, Josh recounts his recent journey of conquering the Leadville MTB 100 in the Colorado Rockies, with the invaluable support of his wife Yana Leonard, CIA, MBA, Director of Finance. Alongside tales of determination and grit, Jos...

Planning for an Early and Intentional Retirement (Ep. 65) 27.08.2024

What if you could retire earlier than you think? In this episode, Josh Leonard and Pete Belcastro dive into the concept of early retirement with the FIRE (Financially Independent, Retire Early) movement, a lifestyle choice emphasizing extreme savings and smart investments. They provide information about how adopting frugality and strategic financial planning can help set you on a path to early ret...

Estate Planning Essentials (Ep. 64) 20.08.2024

You can protect your loved ones and legacy as you transition into retirement by estate planning. Today on Relax, It’s Retirement, host Josh Leonard, and Pete Belcastro dive into the often overlooked but crucial aspect of retirement planning: estate planning. They talk about how to effectively prepare your essential estate documents, avoid the drawbacks of probate, leverage trusts for tax pla...

How to Choose the Best State for Your Retirement (Ep. 63) 13.08.2024

Where should you retire? Your perfect place could be closer than you think. Let’s take a look at some factors that could make or break your retirement decision. Today on Relax, It’s Retirement, Josh Leonard and Pete Belcastro talk about what truly makes a state great for retirement. They dissect a recent study listing the top states for retirement, unpacking factors such as the cost of livin...

Navigating RMD Changes for Your Retirement Plan (Ep. 62) 06.08.2024

Why does the government force you to take money out of your retirement accounts, even if you don’t need it? In this episode or Relax, It’s Retirement, Josh Leonard and Pete Belcastro dive  into the intricacies of Required Minimum Distributions (RMDs) and explain why they are a crucial aspect of retirement planning. Together, they cover recent changes in RMD rules, including the impact...

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