Category: Investing
Episode 100 – A Legacy of Intent (Ep. 100)

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

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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.

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:

Connect with Josh Leonard: 

Connect with 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.

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Turning High Income Into Lasting Wealth (Ep. 99)

Turning High Income Into Lasting Wealth (Ep. 99)

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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:

Connect with Josh Leonard: 

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6 Tax-Smart Takeaways from the One Big Beautiful Bill Act (Ep. 98)

6 Tax-Smart Takeaways from the One Big Beautiful Bill Act (Ep. 98)

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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.

Josh covers:

  • How slightly wider tax brackets may still trigger more taxable income due to Social Security inclusion
  • A new $1,000 charitable deduction for non-itemizers starting in 2026, and how to strategize around it
  • The $6,000 senior deduction and how to layer it with other tactics like Roth conversions
  • SALT cap increases and strategies for households earning $500–600K to reduce taxable income
  • The time-sensitive nature of these changes and how intentional planning can help offset future burdens
  • And more!

Resources:

Connect with Josh Leonard: 

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Bikes, Voices & Victories: Changing Lives with Variety’s Tom Baker (Ep. 97)

Bikes, Voices & Victories: Changing Lives with Variety’s Tom Baker (Ep. 97)

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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.

Tom discusses:

  • The impact of Variety’s My Bike®, My Voice®, and My Stroller® programs on kids with disabilities and their families
  • How a bike becomes more than just equipment, it becomes a bridge to friendship, inclusion, and physical health
  • Why the My Voice iPad program is giving nonverbal children a way to say “I love you” to their parents
  • Stories from families who experience daily wins thanks to adaptive tools, from grocery trips to school events
  • How retirees and local communities can get involved to give back through volunteering, donations, and mentorship
  • And more!

Resources:

Connect with Josh Leonard: 

Connect with Tom Baker:

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.

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Retire with Intent: The True Intent Planning System™ Explained (Ep. 96)

Retire with Intent: The True Intent Planning System™ Explained (Ep. 96)

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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.

Josh discusses:

  • Optimizing income streams in retirement, including Social Security, pensions, annuities, and bridging any income gaps
  • Structuring investments to match retirement goals, manage risk, and address potential tax issues from withdrawals
  • Tax planning strategies, including the benefits of tax diversification, Roth conversions, and minimizing tax burdens for future generations
  • Health care planning, from managing costs pre- and post-Medicare to long-term care considerations and annual prescription reviews
  • The importance of estate planning, updating wills, powers of attorney, and using vehicles like 529 plans for generational wealth and education funding
  • And more!

Resources:

Connect with Josh Leonard: 

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How Recent Retirement Laws May Affect Your Future (Ep. 95)

How Recent Retirement Laws May Affect Your Future (Ep. 95)

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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.

Josh discusses:

  • Changes from Secure Acts 1.0 and 2.0, including increased RMD ages and IRA contribution rules
  • How automatic 401(k) enrollment and escalation can benefit retirement savings
  • The “Good Saver” tax issue and why early tax planning is essential
  • Medicare IRMAA surcharges and how to minimize them with intentional withdrawals
  • Why regularly reviewing and adjusting your financial plan matters more than ever
  • And more!

Resources:

Connect with Josh Leonard: 

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Pine Valley Camp: Building Futures, One Child at a Time (Ep. 94)

Pine Valley Camp: Building Futures, One Child at a Time (Ep. 94)

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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.

Key Discussion Points:

  • The unique mission of Pine Valley Camp in serving underprivileged children and providing a nurturing environment for growth and learning
  • The emotional and spiritual rewards of volunteering, particularly for retirees seeking meaningful engagement
  • The challenges and opportunities in mentoring youth, instilling core values, and breaking cycles of adversity
  • How retirees can use their skills and experiences to contribute to community-driven programs, such as Retired Tuesdays at Pine Valley Camp
  • The long-term vision for Pine Valley Camp, focusing on expanding its reach and sustaining its impact through strategic planning and donor support
  • And more!

Resources:

Connect with Josh Leonard: 

Connect with Matthew Reichart:

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.

Connect with Julie Saenz:

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Can I Retire This Year? (Ep. 93)

Can I Retire This Year? (Ep. 93)

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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.

Josh discusses:

  • How the three-bucket system helps reduce stress about timing your retirement
  • Why proper planning should account for market downturns before they happen
  • The benefits of tax strategies like Roth conversions during lower market years
  • How to prepare mentally and emotionally for the shift from saving to spending
  • Why retirement should be built around purpose, not just portfolios
  • And more!

Resources:

Connect with Josh Leonard: 

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Should You Buy, Lease, or Hold? Car Buying Decisions in Retirement (Ep. 92)

Should You Buy, Lease, or Hold? Car Buying Decisions in Retirement (Ep. 92)

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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.

Josh discusses:

  • The pros and cons of buying new vs. used vehicles
  • Leasing versus purchasing options, highlighting factors like mileage, monthly payments, and long-term costs
  • Financing strategies, including interest rate comparisons, pre-approvals, and the tax implications for retirees
  • The importance of budgeting for car expenses in retirement
  • Personal stories and anecdotes around car buying experiences
  • And more!

Resources:

Connect with Josh Leonard: 

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Retirement Resilience: How to Protect Your Plan in a Volatile Market (Ep. 91)

Retirement Resilience: How to Protect Your Plan in a Volatile Market (Ep. 91)

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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 for them. He also details the bucket strategy, a method to help individuals handle financial uncertainties without making rash decisions.

Josh discusses:

  • Navigating market volatility with long-term plans
  • Understanding market corrections and identifying opportunities
  • The importance of cash and retirement buckets for stability
  • Evaluating risks and rebalancing your portfolio
  • And more!

Resources:

Connect with Josh Leonard: 

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