The end of the year can bring financial stress, but it’s also a valuable time to take control of your retirement strategy.

In this episode of Relax, It’s Retirement, Josh Leonard walks through year-end tax planning steps that can make a real difference for retirees. From RMDs and charitable giving to Roth conversions and managing Medicare costs, Josh highlights how intentional planning today can lead to more confidence tomorrow.

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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 into a practice that now helps hundreds of families retire with clarity and confidence.

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About our Guest: 

William Leonard laid the foundation for  the  Leonard Advisory Group to fill in the gaps he saw when helping his mother plan for retirement. Bill focused much of his career on the insurance and annuity industry. As an independent advisor, he helped thousands of retirees and pre-retirees face the financial challenges that lie ahead with confidence. Since 1996, Bill has worked in a variety of capacities, gaining valuable experience with insurance. In 2007, he became an independent consultant, focusing on income protection and retirement planning. Bill was an honorary host of the “Protecting Your Profits” radio show on 94.5 3WS Pittsburgh and a weekly guest on the national broadcast “Financial Safari” radio show heard locally on NewsTalk 104.7 FM. He has also been featured on WISR 680 AM and WORD FM. In his free time, Bill enjoys traveling, boating, skiing, hiking, biking, restoring antique vehicles, and spending quality time with family, friends, and clients. He has been married to his wife, Cindy, for almost 40 years. They have three children: Zach, Josh, and Zoey, as well as a crazy border collie named Sweep. After over 25 years assisting families transition into retirement Bill transitioned himself into retirement at the end of 2022.

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 using charitable giving vehicles and understanding capital gains planning, Josh explains how intentional decisions today can lead to a more tax-efficient retirement tomorrow.

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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, he outlines six crucial areas that deserve your attention now.

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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 disabilities participate in everyday joys like riding a bike, going to the grocery store, or simply being heard. 

From adaptive strollers to communication tools, this episode is full of remarkable victories that make a difference close to home.

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About Our Guest: 

Tom proudly serves as the Chief Executive Officer of Variety- The Children’s Charity of Pittsburgh. With a mission to empower children with disabilities to live life to the fullest, Variety provides life-changing adaptive mobility and communication equipment. Variety focuses on three core programs: My Bike®, My Stroller®, and My Voice® throughout 59 counties in PA. Previously, he was Executive Director of North Hills Community Outreach. For 12 years, Tom served as the Chief Community Affairs Officer/Vice President of Programs for Big Brothers Big Sisters of Greater Pittsburgh and as President of the BBBS Pennsylvania State Association. He has volunteered as a Big Brother to his little brothers Preston (since 2002), Eric (since 2010), E.J. (since 2015), Eddie (since 2018), and Brian (since 2024) and as a Tutor at Anchorpoint with Ethan (since 2021). He is the Founder/Chief Program Officer of Get Involved!, Inc., and since 2008 has spoken with over 500,000 students, young professionals, and lifelong learners at over 1.000 colleges, corporations, and civic groups across the country.

Tom served as President of the Pittsburgh East Rotary Club (2010-12)and President of the Hampton Rotary Club (2023-25). He is President of the Job Corps Community Relations Council, Chair-Elect of the Pittsburgh North Regional Chamber, Past President of NSA Pittsburgh, and Past President of the PUMP Board. Tom received the 2023 Pittsburgh Business Times C-Suite Award, the 2025 Heart of Hampton Award, the 2022 Ross Township Citizen of the Year Award, the 2022 North Hills School District Community Service Award, and was named to the City & State PA 2022 Nonprofit Power 100 List. In 2009, he received the Distinguished Civic Leadership Award from Millersville, and in 2014, he was honored with the MU Young Alumni Achievement Award. Junior Achievement recognized Tom with the 2018 Mayor Caliguiri Good Samaritan Award, and the PNRC honored him with the 2018 Young Professional Award. The Monroeville Area Chamber selected him as the 2011 Young Business Leader of the Year, and Pittsburgh Magazine named him a “40 Under 40” honoree in 2014 and Three Rivers Champion winner in 2017. In Community Magazine, Tom was named 2014 Volunteer of the Year for Ross Township, and he received the 2015 Indiana University of PA Young Alumni Achievement Award. In 2017, he received the Dick Spahr Compassion in Action Award from NHCO. Tom was a 2010 Jefferson Award for Public Service honoree, received the 2014 Distinguished Alumni Leadership Award from Coro, and was a 2013 Pittsburgh Business Times Fast Track honoree.

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 planning for income, investments, taxes, healthcare, and estate matters, and discusses real-life stories and practical tips for retirees.

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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 surcharges can affect retirees, especially those who have saved diligently. 

Josh also shares practical strategies to prepare for the evolving legal environment without overreacting to proposals.

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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 of Pine Valley Camp, and Julie Saenz about how retirees can embrace their next chapter by giving back. They explore the transformative power of service, the joys of community involvement, and the lasting impact of shaping young lives through Pine Valley Camp.

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About Matt Reichart: 

Mr. Matt and his wife Miss Susan began this ministry at Pine Valley 30 years ago with a desire to create a loving family atmosphere, in a place set apart, where kids could encounter the life-changing gospel message. Matt and Susan have been married 43 years, have 5 adult married children, and 31 grandchildren to date.

Mr. Matt is incredibly passionate about the gospel, relationships, and play! He often says kids spell love P.L.A.Y. He loves adventure, so if you stop by camp, you can still find him making time to throw campers in the pool or give jeep rides.

Miss Susan is compassionate and is known as the “camp mom”. Because of her desire to create an atmosphere of warmth and kindness, she has a ministry of availability. You will often find her poolside or fireside or about anywhere that someone is in need of a chat.

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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 can weather short-term challenges while aligning with your values and lifestyle. He covers tax-efficient tactics, managing income, and finding purpose beyond work.

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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 choosing a new vehicle in retirement. He compares leasing with buying, discusses the impact of interest rates, and shares tips to make smarter purchasing choices without breaking the budget.

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