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. Sep 3

    Mental Health in Construction: Breaking the Stigma with Mike Scalamogna (Ep. 113)

    Mental health struggles can be difficult to recognize and even harder to talk about, especially in environments where people feel pressure to stay tough and keep their emotions private. In this episode, Josh Leonard talks with Mike Scalamogna, Manager, SD Digital at Schneider Downs and CFMA Western Pennsylvania Chapter Champion for Mental Health and Suicide Prevention, about losing his father to suicide and turning that experience into support for others. They explore mental health in construction, therapy, parenting, empathy, and why simply listening can help someone feel less alone. Mike also shares how a benefit concert is raising awareness and funds for the American Foundation for Suicide Prevention. Key points: Why construction workers face serious mental health concerns alongside a culture that can discourage openness How Mike’s experience losing his father to suicide shaped his approach to mental health and helping others Why therapy, emotional awareness, and honest communication can become meaningful forms of personal care How parents can model emotional awareness and give children language for understanding what they’re feeling How volunteering and community involvement can create connection while supporting people experiencing loss And more! Resources: Contact us to schedule a meeting with the team American Foundation for Suicide Prevention Get your tickets for the benefit concert and help support the American Foundation for Suicide Prevention 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 Mike Scalamogna: LinkedIn: Mike Scalamogna Website: Schneider Downs Website: CFMA About our Guest:  Mike Scalamogna works in the digital practice at Schneider Downs, where he helps clients use technology across industries including construction, transportation and logistics, real estate, and dealerships. He is also involved with the Construction Financial Management Association (CFMA) Western Pennsylvania Chapter, where he serves as the Chapter Champion for Mental Health and Suicide Prevention. After losing his father to suicide as a teenager, Mike turned his personal experience into a commitment to raising awareness, reducing the stigma around mental health, and supporting others affected by suicide loss. His advocacy includes volunteering with the American Foundation for Suicide Prevention and organizing efforts that bring people together to support mental health and suicide prevention.

  2. Aug 25

    How Grandparents Can Support Family Without Hurting Their Retirement with Yana Leonard (Ep. 112)

    Helping your children and grandchildren can become one of the most meaningful parts of retirement, but how much time, money, and energy can you comfortably give? In this episode, Josh Leonard and Yana Leonard, Chief Risk and Operations Officer at Leonard Advisory Group, explore how grandparents are becoming a bigger part of childcare, family finances, and everyday life. They share their own experience relying on grandparents, examine the financial pressure that family support can create, and consider 529 plans, family trips, relocation, and other ways retirees may help.  Josh also explains why these choices belong in retirement planning, including the need to protect your own time, resources, and independence. Key points: How childcare and after-school help from grandparents can change a working family’s budget and daily routine Why financial help for adult children and grandchildren needs to be considered within a retirement plan How 529 plans, family vacations, and other gifts can turn retirement resources into shared family experiences Why grandparents need room for their own travel, interests, independence, and personal retirement priorities How retirement planning can account for family support without overlooking your own financial and personal needs And more! Resources: Contact us to 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 Yana Leonard: LinkedIn: Yana Leonard About our Guest:  Yana Leonard serves as Chief Risk and Operations Officer, where she helps ensure every client experience is delivered with clarity, care, and consistency. She oversees firm operations, internal controls, and compliance, supporting a strong foundation that allows advisors to focus on helping clients plan with confidence and live with intent. With 15 years of corporate finance experience, Yana brings a disciplined, thoughtful approach to decision-making, always focused on protecting clients’ best interests and the long-term strength of the firm. Yana holds her Life and Fixed Annuities and Accident & Health insurance licenses, reinforcing the firm’s comprehensive approach to retirement planning. She holds a Bachelor of Arts in Accounting with a minor in Economics and a Master of Business Administration (MBA) with a concentration in Accounting from Baldwin Wallace University. She is also a Certified Internal Auditor (CIA). Yana lives in Pittsburgh with her husband, Josh, their sons, Eli and Isaac, and Layla, their golden retriever. When she’s not working, she enjoys gardening, volunteering, traveling, and being on the sidelines for her boys’ sporting events.

  3. Jul 8

    5 Retirement Planning Questions to Ask Before Summer Spending (Ep. 111)

    Summer often brings vacations, family activities, and unexpected expenses, making it easy to lose sight of financial goals.  Taking a few proactive steps before spending ramps up can help you avoid unnecessary taxes, overlooked opportunities, and preventable financial headaches. In this episode, Josh Leonard and Pete Belcastro explore five financial questions to ask before summer gets into full swing. They explain why reviewing tax withholding, checking beneficiary designations, evaluating insurance coverage, maximizing tax-advantaged accounts, and planning seasonal expenses can help retirees and those approaching retirement make more informed financial decisions.  They also clarify the difference between tax preparation and tax planning while sharing practical ways to make retirement spending more intentional throughout the year. Key takeaways: Reviewing tax withholding before large withdrawals may help reduce unexpected tax surprises later Checking beneficiary designations after life changes helps retirement assets reflect current wishes Evaluating insurance coverage before traveling may help avoid duplicate policies and extra costs Using HSAs, Roth accounts, and employer matches can improve long-term tax efficiency over time Planning summer expenses ahead of time helps reduce financial stress during vacations and family activities 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 Pete Belcastro: LinkedIn: Pete Belcastro

  4. May 26

    5 Problems With Mutual Funds in Retirement (Ep. 110)

    Owning multiple mutual funds doesn’t mean you have a diversified retirement plan, and for many retirees, it can create surprises they never saw coming. In this episode, Josh Leonard sits down with Leonard Advisory Group CFP® Peter Belcastro to unpack the five common problems they see with mutual funds, especially for people nearing or living in retirement. While mutual funds can be a great starting point for investing, Josh and Pete explain why they may not always fit a complete retirement strategy. Josh and Pete discuss: Why diversification inside mutual funds can sometimes be an illusion How overlapping investments may increase risk without people realizing it The hidden tax consequences of mutual funds, including “phantom gains.” Why investment tools should support a retirement plan, not replace one 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 Pete Belcastro: LinkedIn: Pete Belcastro Leonard Advisory Group  About our Guest: Pete Belcastro is a CERTIFIED FINANCIAL PLANNER professional at Leonard Advisory Group. In addition to helping clients build intentional retirement plans, Pete brings deep experience in the mutual fund and investment management space. In this episode, he joins Josh Leonard to break down common misconceptions around diversification, taxes, and investment strategy, helping listeners better understand how their investments fit into a broader retirement plan.

  5. May 5

    The Retirement Stress Test: What Breaks First in Your Plan? (Ep. 109)

    Most people don’t have a bad retirement plan; they just haven’t tested it yet. In this episode, Josh Leonard walks through what it really means to pressure-test your retirement plan before you step away from work. Using a real client story, he breaks down how a plan that looks solid on paper can still carry hidden risks if it hasn’t been coordinated across income, taxes, investments, healthcare, and legacy. Josh shares how small adjustments, like restructuring investments into purpose-driven “buckets,” planning for tax-efficient withdrawals, and reviewing beneficiary designations, can make a meaningful difference over time. He also highlights how overlooking factors like Medicare decisions or account structure can lead to unnecessary costs later. This conversation is a reminder that retirement isn’t just about how much you’ve saved; it’s about how everything works together when you need it most. Josh discusses:  Why retirement plans need to be stress tested, not just built The “bucket strategy” for income, cash, and growth How market downturns early in retirement can impact long-term outcomes Hidden tax risks and how to think about withdrawals more intentionally 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

  6. Apr 7

    Staying Invested Through Market Noise with Dominic Pappalardo (Ep. 108)

    Markets move fast, headlines move faster, and emotions often follow. So how do you stay grounded when uncertainty feels constant and every decision seems urgent? In this episode, Josh Leonard speaks with Dominic Pappalardo, Chief Wealth Strategist at Morningstar Wealth, about maintaining discipline during volatile markets. They break down a bucket-based investment approach, the importance of long-term thinking, and why reacting to headlines can hurt outcomes. Dominic also shares insights on missing key market days, evaluating AI valuations, and how bonds and sector dispersion are shaping current opportunities. Key takeaways: Why structuring portfolios into cash, income, and growth buckets helps reduce emotional decisions Missing just a few key trading days can significantly impact long-term returns and outcomes AI growth remains strong, but long-term value depends on real returns from adoption by businesses Bonds now offer better income support compared to prior years due to higher starting yields Market opportunities often come from gaps between pricing and fundamentals across sectors 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 Dominic Pappalardo: LinkedIn: Dominic Pappalardo Website: Morningstar  About our Guest:  Dominic Pappalardo is chief multi-asset strategist for Morningstar Wealth. He plays a crucial role as a public-facing ambassador to a variety of media channels. His work ensures that complex asset class views, macroeconomic insights, and portfolio positioning are communicated effectively to a wide range of audiences. Dominic leads the production of insightful commentary and research intended to engage and inform a diverse client base. Acting as a vital link between the investment team and clients, he is instrumental in enhancing visibility and engagement around the firm’s highest conviction ideas. Internally, he collaborates closely with the portfolio management and research teams to maintain cohesion in macroeconomic perspectives and asset class views, delivering a unified narrative to stakeholders. Advisory services under Morningstar Wealth are offered by Morningstar Investment Management LLC, a registered investment adviser and subsidiary of Morningstar, Inc. Before joining Morningstar in 2020, Pappalardo cultivated nearly two decades of experience managing all facets of fixed income strategies at McDonnell Investment Management, an affiliate of Natixis Investment Managers. Pappalardo holds a B.B.A. in Finance from Benedictine University. He also holds an M.B.A from The University of Notre Dame’s Mendoza College of Business.

  7. Mar 24

    Spring Tax Cleaning: 3 Hidden Opportunities in Last Year’s Return (Ep. 107)

    A tax return can reveal more than what happened last year; it can point to choices that may help reduce friction and improve retirement income over time. What hidden issues could be sitting in your paperwork, and what small moves today could help you avoid bigger tax headaches later? In this episode, Josh Leonard explains how a closer look at your tax return can uncover planning opportunities before they grow into larger retirement issues. He covers phantom gains in taxable accounts, why a 0% tax bill can still create future problems, and how tax bracket planning matters before required distributions begin. Josh also walks through charitable giving strategies, including new 2026 deduction rules and qualified charitable distributions for IRA owners. Key takeaways: Why phantom gains from mutual funds can create taxable income even when your account balance declines overall How a 0% tax return may hide a future jump into higher brackets once pensions and RMDs begin later on Why reviewing taxable income sources can reveal avoidable drag from dividends, rebalancing, and fund sales How Roth conversions can help spread taxes across retirement years instead of pushing income into later spikes Why charitable gifts may be more effective through new deductions or direct IRA transfers after age 70 and a half 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

  8. 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

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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.

Information

  • Creator
    Josh Leonard
  • Years Active
    2022 - 2026
  • Episodes
    113
  • Rating
    Clean
  • Copyright
    Copyright © 2022 Relax, It’s Retirement Podcast
  • Show Website
    Relax, It’s Retirement Podcast

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