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

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

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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:

Connect with Josh Leonard: 

Connect with 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.

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

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

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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:

Connect with Josh Leonard: 

Connect with Pete Belcastro:

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.

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

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

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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:

Connect with Josh Leonard: 

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

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

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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:

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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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Capital Loss Harvesting vs. Capital Gain Harvesting: What’s Right for Your Retirement? (Ep. 69)

Capital Loss Harvesting vs. Capital Gain Harvesting: What’s Right for Your Retirement? (Ep. 69)

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Are you maximizing the potential of capital gains and losses in your retirement planning?

This week, Josh Leonard and Pete Belcastro dive into the often-overlooked strategies of capital gain and loss harvesting. You’ll learn the essential differences between capital loss and capital gain harvesting, why timing and tax brackets play a crucial role in your financial planning, and how these strategies can help minimize your tax liability, particularly in retirement. 

Join us for an informative discussion that could significantly influence how you manage your investments for a more secure financial future.

Josh and Pete discuss: 

  • Exploring Capital Loss vs. Capital Gain Harvesting: Understanding the fundamental principles and their implications for your tax strategy
  • Timing is Everything: Why the fourth quarter is critical for reviewing and adjusting your tax planning strategies
  • Tax Brackets: How these affect your decision-making on selling assets and realizing gains or losses
  • Retirement Focus: Tailoring these strategies to optimize tax savings and maintain financial health in your golden years
  • And more!

Resources:

Connect with Josh Leonard: 

Connect with Pete Belcastro: 

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The Three-Bucket Strategy for Retirement Planning with Pete Belcastro
The Three-Bucket Strategy for Retirement Planning with Pete Belcastro (Ep. 37)

The Three-Bucket Strategy for Retirement Planning with Pete Belcastro (Ep. 37)

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Is your financial plan secure enough to last until retirement? How could dividing your income into separate groups help ensure your retirement income will last?

Check out this episode as Josh Leonard and Pete Belcastro from the Leonard Advisory team explore the essential elements of retirement preparation. They delve into the “three baskets” strategy, which includes the cash, income, and growth categories. Emphasizing the necessity of an emergency reserve, they discuss allocating funds for predictable costs through secure investments and the importance of long-term growth strategies to manage significant future expenses such as healthcare.

Josh and Pete discuss: 

  • Why is comprehensive retirement planning important
  • What are the three baskets in retirement planning
  • How do stable investments ensure a steady income stream during retirement
  • What role do different financial buckets play in providing insulation and protection for retirement savings
  • And more

Resources:

Connect with Josh Leonard: 

Connect with Pete Belcastro: 

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Are You Thinking About Un-Retiring? (Ep. 21)

Are You Thinking About Un-Retiring? (Ep. 21)

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Retirement just isn’t what it used to be.  

In this episode, Josh Leonard discusses the concept of “unretirement” and finding a mission in the next phase of life. They challenge the conventional understanding of retirement, discussing the potential pitfalls, tax implications, and the emotional aspects of stepping away from a lifelong career.

Josh unpacks:

  • The future of retirement and how individuals are seeking purpose beyond the paycheck
  • Caution against claiming social security too early due to potential repayments
  • Reasons why individuals return to the workforce post-retirement
  • The emotional aspects of work: finding a mission, purpose, and social connection
  • How work can serve as a gateway to community involvement
  • Tax implications of relocating during retirement
  • And more!

Resources:

Connect with Josh Leonard: 

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