Relax, It’s Retirement Podcast
Business & Economics Podcasts
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.
Location:
United States
Description:
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.
Language:
English
Contact:
412.998.7526
Episodes
Episode 100 – A Legacy of Intent (Ep. 100)
10/7/2025
When you hit a milestone, you pause to reflect. In this special 100th episode, Josh Leonard is joined by his father, Bill Leonard, whose work laid the foundation of what is now the Leonard Advisory Group. Together, they revisit the firm’s humble beginnings, envelopes licked in a basement, meetings around kitchen tables, and the evolution … Read More Read More
Duration:00:28:45
Turning High Income Into Lasting Wealth (Ep. 99)
9/23/2025
Earning a high income doesn’t automatically translate to lasting wealth. The real challenge is how to transform those peak earning years into a retirement filled with stability and freedom. In this episode, Josh Leonard shares three practical strategies to reduce taxes now and build wealth for the long term. From maxing out tax-advantaged accounts to … Read More Read More
Duration:00:31:30
6 Tax-Smart Takeaways from the One Big Beautiful Bill Act (Ep. 98)
8/27/2025
Tax law changes are here, some good, some complicated. But one thing’s for sure: now is the time to adjust your plan. In this episode, Josh Leonard breaks down the One Big Beautiful Bill Act and what it means for those nearing or entering retirement. From enhanced deductions to planning around RMDs and Social Security, … Read More Read More
Duration:00:29:08
Bikes, Voices & Victories: Changing Lives with Variety’s Tom Baker (Ep. 97)
8/6/2025
What if your child said “I love you” for the first time thanks to an iPad? That’s just one of the many moments families experience with Variety’s life-changing programs. In this episode, Josh Leonard sits down with Tom Baker, CEO of Variety the Children’s Charity of Pittsburgh, to share powerful stories about helping children with … Read More Read More
Duration:00:32:48
Retire with Intent: The True Intent Planning System™ Explained (Ep. 96)
7/23/2025
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 … Read More Read More
Duration:00:29:39
How Recent Retirement Laws May Affect Your Future (Ep. 95)
7/2/2025
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 … Read More Read More
Duration:00:30:05
Pine Valley Camp: Building Futures, One Child at a Time (Ep. 94)
6/11/2025
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 … Read More Read More
Duration:00:49:42
Can I Retire This Year? (Ep. 93)
5/21/2025
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 … Read More Read More
Duration:00:26:56
Should You Buy, Lease, or Hold? Car Buying Decisions in Retirement (Ep. 92)
5/7/2025
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 … Read More Read More
Duration:00:35:45
Retirement Resilience: How to Protect Your Plan in a Volatile Market (Ep. 91)
4/15/2025
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 … Read More Read More
Duration:00:22:38
Spring Clean Your Finances: 5 Essential Tips for a Fresh Start (Ep. 90)
4/1/2025
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, … Read More Read More
Duration:00:27:34
Avoiding the Good Saver Tax Problem with Proactive Planning (Ep. 89)
3/11/2025
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 … Read More Read More
Duration:00:20:46
Unpacking Social Security Changes (Ep. 88)
2/18/2025
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 … Read More Read More
Duration:00:19:35
Planning Ahead for Retirement (Ep. 87)
2/4/2025
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 … Read More Read More
Duration:00:32:25
Conquering Retirement Fears with Confidence (Ep. 86)
1/21/2025
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 … Read More Read More
Duration:00:25:43
The Diversification Dilemma: Are Your Investments Really Safe? (Ep. 85)
1/14/2025
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 episode has … Read More Read More
Duration:00:30:50
Mastering the Tax Triangle (Ep. 84)
1/7/2025
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 … Read More Read More
Duration:00:23:43
The Five Worlds of Money in Retirement (Ep. 83)
12/31/2024
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 … Read More Read More
Duration:00:22:56
Setting Goals for a Purposeful Retirement (Ep. 82)
12/24/2024
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 … Read More Read More
Duration:00:27:17
Making the Most of Holiday Giving in Retirement (Ep. 81)
12/17/2024
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 … Read More Read More
Duration:00:27:13