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, …
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 …
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 …
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 …
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 …
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, …
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 …
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 …
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 …
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 …