Tag: Retirement Income
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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