Relax, It’s Retirement Podcast

Josh Leonard
  • 5.0 (12)
  • INVESTING
  • UPDATED SEMIMONTHLY

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.

  1. FEB 17

    Don’t Let “One More Year” Steal Your Retirement (Ep. 106)

    What if “just one more year” at work costs you more than it gives you? In this episode, Josh Leonard challenges one of the most common retirement assumptions, the idea that working one more year is always the safer choice. While extra income can feel reassuring, delaying retirement can quietly take time, health, energy, and meaningful experiences you may never get back. Josh walks through real client stories and practical planning scenarios that show why one more year is often an emotional decision, not a financial one. He introduces a simple trade-off filter to help listeners evaluate whether delaying retirement truly improves their plan or simply postpones living the life they’ve already earned. Josh discusses: Why being financially ready does not always make retiring emotionally easy How taxes, required distributions, and healthcare can change the math The hidden cost of delaying retirement when time and health are limited A three-question framework to evaluate if one more year actually helps How intentional income planning creates confidence to retire sooner And more! Resources: Schedule a meeting with the team Connect with Josh Leonard:  jleonard@leonardadvisorygroup.com LinkedIn: Josh Leonard Leonard Advisory Group 412-998-PLAN YouTube: Leonard Advisory Group Facebook: Leonard Advisory Group

    27 min

  2. FEB 3

    From Success to Strategy: Planning With Intent for High Earners (Ep. 105)

    If you have ever thought, “I make good money, so why does this still feel complicated?”, you are not alone. In this episode, Josh Leonard breaks down why higher income often brings more friction, not less, and why success can quietly add complexity to your financial life if it is not coordinated with intention. In this episode, Josh walks through what he commonly sees with high earners who are capable, driven, and successful, but short on time. As income grows, financial systems tend to layer on bonuses, equity compensation, multiple accounts, real estate, and tax exposure. None of these are mistakes, but without a clear framework, small inefficiencies can build up and slow progress toward retirement. Josh discusses: Why success rarely simplifies finances on its own How “financial friction” shows up through taxes, concentration risk, and misaligned accounts The role of coordination across investments, taxes, income, healthcare, and estate planning Why having money does not always mean having liquidity How planning with intent helps decisions reinforce each other instead of working against each other And more! Resources: Schedule a meeting with the team Connect with Josh Leonard:  jleonard@leonardadvisorygroup.com LinkedIn: Josh Leonard Leonard Advisory Group 412-998-PLAN YouTube: Leonard Advisory Group Facebook: Leonard Advisory Group

    25 min

  3. JAN 20

    Setting SMART Goals: From New Year’s Resolutions to Real Retirement Readiness (Ep. 104)

    Big goals often feel exciting at the start, but how many actually make it past February? What separates the intentions that fade from the habits that last? In this episode, Josh Leonard breaks down the SMART goal framework and shares his personal goals for the year, from conquering Pittsburgh’s Dirty Dozen bike race to building non-negotiable daily habits. He explains how this same intentional approach applies to retirement planning and why clarity creates confidence when preparing for your next chapter. Key points: How the SMART framework turns vague resolutions into achievable goals with clear benchmarks and timelines Josh’s three major goals for the year and the specific training, habits, and preparation each requires Why knowing your monthly expenses is the first step in any meaningful retirement plan How hobbies and projects in retirement create purpose beyond simply not working anymore The importance of aiming high and tracking progress, even when life gets in the way And more! Resources: Schedule a meeting with the team Connect with Josh Leonard:  jleonard@leonardadvisorygroup.com LinkedIn: Josh Leonard Leonard Advisory Group 412-998-PLAN YouTube: Leonard Advisory Group Facebook: Leonard Advisory Group

    26 min

  4. 12/26/2025

    How a 60-Mile Mountain Bike Race Reinforced the Power of Intentional Living (Ep. 103)

    Big goals often look simple until you are in the middle of them, tired, uncertain, and second-guessing everything. How do you stay steady when the plan shifts? How do you prepare for the parts you cannot predict? In this episode, Josh Leonard shares how a grueling 60-mile mountain bike race deepened his view on preparation, mindset, and the importance of thinking ahead. He talks about the parallels between physical endurance and retirement planning, the value of support systems, and how steady habits create a more intentional life.  Key points: Planning missteps that made the Austin race tougher, and why preparation shapes outcomes How heat, hydration, and equipment choices influenced the long ride and its lessons Why support systems matter when facing difficult moments or big goals How intentional preparation mirrors the steps needed for retirement planning The value of seeking growth at every stage of life and staying engaged And more! Resources: Schedule a meeting with the team Connect with Josh Leonard:  jleonard@leonardadvisorygroup.com LinkedIn: Josh Leonard Leonard Advisory Group 412-998-PLAN YouTube: Leonard Advisory Group Facebook: Leonard Advisory Group

    28 min

  5. 12/02/2025

    When Should High-Net-Worth Retirees Take Social Security? (Ep. 102)

    Planning for retirement comes with many choices that can shape long-term comfort and confidence. Small shifts in timing, taxes, and income strategy can influence how well your resources support the life you want to enjoy. In this episode, Josh Leonard breaks down how Social Security fits into a broader retirement plan for high-net-worth individuals, explaining how timing, tax brackets, portfolio design, and future goals work together. He highlights why delaying benefits can reduce risk, how tax planning affects income decisions, and why Social Security should be coordinated with the full financial picture. Key Insights: Why higher savings create more flexibility around Social Security timing How IRMAA can affect Medicare costs when income rises unexpectedly How delaying benefits can lower long-term risk and support lifetime income How portfolio restructuring reduces unnecessary taxes from mutual fund gains Why Social Security choices must connect with tax, investment, and legacy planning And more! Resources: Schedule a meeting with the team Connect with Josh Leonard:  jleonard@leonardadvisorygroup.com LinkedIn: Josh Leonard Leonard Advisory Group 412-998-PLAN YouTube: Leonard Advisory Group Facebook: Leonard Advisory Group

    26 min

  6. 11/18/2025

    Taxes, Timing, and the End of the Year: What You Can Still Control (Ep. 101)

    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. Josh shares: Why year-end tax planning matters and how deadlines impact your financial picture How to use Qualified Charitable Distributions (QCDs) to meet RMD requirements while supporting meaningful causes What to do if you face the “good saver tax problem” and want to pass wealth efficiently to the next generation How Roth conversions and new senior deductions can help balance taxes in retirement Why managing IRMAA limits can prevent unexpected Medicare cost increases And more! Resources: Schedule a meeting with the team Attend One of Our Educational Events Connect with Josh Leonard:  jleonard@leonardadvisorygroup.com LinkedIn: Josh Leonard Leonard Advisory Group 412-998-PLAN YouTube: Leonard Advisory Group Facebook: Leonard Advisory Group

    27 min

  7. 10/07/2025

    Episode 100 – A Legacy of Intent (Ep. 100)

    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. Key takeaways: How Bill transitioned from architecture to financial advising Family lessons that shaped Leonard Advisory Group’s mission Stories of clients whose planning ensured lasting comfort The importance of foresight over hindsight in retirement And more! Resources: Schedule a meeting with the team Connect with Josh Leonard:  jleonard@leonardadvisorygroup.com LinkedIn: Josh Leonard Leonard Advisory Group 412-998-PLAN YouTube: Leonard Advisory Group Facebook: Leonard Advisory Group Connect with Bill Leonard: LinkedIn: Bill Leonard 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.

    29 min

  8. 09/23/2025

    Turning High Income Into Lasting Wealth (Ep. 99)

    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. Key takeaways: The importance of converting “rich” (high income) into true wealth  Maxing out 401(k), IRA, Roth, and HSA contributions to take advantage of tax benefits  How donor-advised funds can amplify charitable giving while reducing taxes Using deferred compensation and capital gains strategies for long-term efficiency Why proactive retirement planning makes the transition smoother and more intentional And more! Resources: Schedule a meeting with the team Connect with Josh Leonard:  jleonard@leonardadvisorygroup.com LinkedIn: Josh Leonard Leonard Advisory Group 412-998-PLAN YouTube: Leonard Advisory Group Facebook: Leonard Advisory Group

    32 min
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Ratings & Reviews

5
out of 5
12 Ratings

About

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.

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