Are you looking to maximize your tax bracket and secure a stress-free retirement? You might want to consider adding Roth conversions to your retirement plan. Josh Leonard and Pete Belcastro dive into the world of Roth conversions, discussing three key scenarios when converting to a Roth IRA might benefit your retirement plan with a focus on reducing taxes, maximizing income, and securing a tax-efficient legacy for your family.  Josh and Pete discuss:  Maximizing your tax bracket by strategically converting to a Roth IRA to save on taxes in the future Using Roth funds for emergency o ..read more

Are you nearing retirement but still burdened with your kid’s college debt payments? Discover how you can potentially cut those payments in half with The College Dude. Today on Relax, It’s Retirement, Josh Leonard and Dan Cieniewicz, CFP®, CCFC, CSLP®, a.k.a. The College Dude, delve into the world of managing Parent PLUS loans to balance funding education and retirement savings effectively. They discuss the nuances of student debt repayment strategies, income-driven repayment plans, the double consolidation loophole, and the impact on retirement planning. Josh and Dan discuss: Understanding P ..read more

Have you ever wondered how quickly the stock market can plunge into a bear market and the impact it has on your investments? Join Josh Leonard and our Pete Belcastro, as they delve into three significant market crashes in history, including the 1929 stock market crash, Black Monday in 1987, and the recent COVID market meltdown. Discover how fear drives investors, the role of margin accounts, and the importance of long-term investing, even in times of extreme volatility. Josh and Pete discuss: Historical market crashes: 1929, Black Monday 1987, and the COVID crash in 2020 Examining the impact ..read more

What’s your retirement adventure? Meet Barbara Hillary, the trailblazer who set foot on the North Pole at 76. Let’s explore her remarkable story! In this special Women’s History Month episode, Josh Leonard and Yana Leonard, CIA, MBA, Director of Finance, share the incredible life story of Barbara Hillary, an inspiring woman who challenged herself to achieve the impossible. From battling cancer to conquering the North Pole at 76, Barbara’s journey is a testament to resilience and determination. Discover how she raised funds, trained rigorously, and embodied the spirit of adventure in retirement ..read more

What’s your retirement adventure? Meet Barbara Hillary, the trailblazer who set foot on the North Pole at 76. Let’s explore her remarkable story! In this special Women’s History Month episode, Josh Leonard and Yana Leonard, CIA, MBA, Director of Finance, share the incredible life story of Barbara Hillary, an inspiring woman who challenged herself to achieve the impossible. From battling cancer to conquering the North Pole at 76, Barbara’s journey is a testament to resilience and determination. Discover how she raised funds, trained rigorously, and embodied the spirit of adventure in retirement ..read more

Have you ever found yourself making financial decisions based on instinct rather than informed choices?  In this episode, Josh Leonard talks about five common behavioral biases that can influence financial decision-making. He addresses loss aversion, confirmation bias, herd mentality, overconfidence, and anchoring bias, illustrating each with real-world examples. He also discusses the influence of laziness and habit on decision-making and suggests a four-step approach to counteract biases: recognition, education, professional advice, and informed decision-making. Josh discusses:  Lo ..read more

In a world filled with distractions and temptations, discipline stands as a beacon of consistency and success, guiding us toward our goals and aspirations. Whether in financial planning, health routines, or personal growth, discipline forms the foundation for long-term achievement and fulfillment. Today on Relax, It’s Retirement, Josh and Pete Belcastro, CFP®, talk about discipline in various aspects of life, drawing parallels between maintaining financial discipline and personal habits. Using personal anecdotes, they emphasize the importance of setting realistic goals, committing to long-term ..read more

Tax time is near. Nobody wants to pay taxes, but we have to, so let’s talk about how we can maximize our tax savings. In this episode, Josh Leonard and Pete Belcastro, Financial Planner at Leonard Advisory Group, talk about tax planning. They share tips for filing taxes this year and some ways to help reduce taxation in the future and be more tax-efficient. Josh and Pete cover the importance of reporting interest from savings accounts, accurately reporting capital gains from stock sales, and the benefits of qualified charitable distributions.  Their conversation also includes strategies f ..read more

Have you ever wondered how successful couples navigate the challenges of marriage, parenthood, and career? Meet Yana Leonard, CIA, MBA, a key member of the team at Josh Leonard Advisory Group, as she steps into the spotlight in this episode of Relax, It’s Retirement. Today, Josh introduces his wife, Yana Leonard, CIA, MBA, Director of Finance, to listeners. They dive into the evolution of their relationship from their college days to marriage. Josh and Yana candidly discuss the hurdles they’ve overcome, including the birth of their children and the strain of the COVID-19 pandemic on their fami ..read more

What are the long-term impacts of keeping your 401(k) with a former employer versus rolling it over to an IRA or a new employer’s plan? How can the benefits of IRA rollovers and Roth conversions influence your decision for penalty-free withdrawals? Josh Leonard explores the advantages and disadvantages of maintaining the 401(k) with a past employer, transitioning it into an IRA, or moving it to the retirement plan of a new employer.  He highlights the importance of comprehending the regulations, costs, and tax consequences associated with each plan.  Josh discusses:  What are t ..read more