Josh Leonard

Relax, It’s Retirement Podcast

Business EN ↓ 112 episodes

Are you worried about the impact of taxes in retirement? Concerned you might run out of money in retirement? Are you looking to avoid making costly pitfalls transitioning into retirement? Welcome to the Relax, It’s Retirement Podcast with Josh Leonard from Leonard Advisory Group. In this podcast, we help those nearing retirement greet it with a well prepared smile. Join Josh and his guests to learn the retirement and tax planning tips you need so that you too, can live your golden years with the happiness and excitement you deserve. Hear stories from his years of experience to help you transit...

Author

Josh Leonard

Category

Business

Latest episode

Jul 8, 2026

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Episodes

Seven Steps to Successful Retirement (Ep. 36) 06.02.2024

Is your retirement plan set for a successful future? When was the last time you reviewed your plan and ensured it has been adapted for any life-changing events? Discover the seven key steps for achieving a fulfilling retirement with Josh Leonard. He touches on everything from crafting a budget and merging accounts to making savvy choices regarding health insurance and maximizing entitlements. Josh...

Building Memorable Culture Moments at Work with Eric Leathem (Ep. 35) 30.01.2024

How do you build a connection with your work colleagues? How has your work culture helped with personal and professional growth? Listen in as Josh Leonard and his guest Eric Leathem, director of operations at Leonard Advisory, explore Eric’s career journey with Leonard Advisor – his entry, his exit and his return. They reveal the workplace culture built in Leonard Advisory and how it contrib...

Managing the Unpredictability in Market Predictions for Investment Planning with Pete Belcastro, CFP® (Ep. 34) 23.01.2024

Can current market predictions be as off the mark? How do long-term investment strategies and emotional management play into market unpredictability? How do unexpected market outcomes challenge current forecasts? Listen in as Josh Leonard and Pete Belcastro, Financial Planner at Leonard Advisory Group, dive into what the market’s been up to and look back at some of the surprises from last ye...

Refine Your Financial Goals for Retirement with Lists (Ep. 33) 16.01.2024

Did you add financial goals to your New Year’s resolutions? What happens when those goals aren’t the best option for your financial plan but you don’t want to change them? Sticking to those goals could do more harm than good. Josh Leonard goes beyond the surface, addressing the intricacies of financial goal-setting and providing tangible examples of how lists can serve as a guiding force in...

Achieving and Setting Goals with Pete Belcastro, CFP® (Ep. 32) 09.01.2024

The New Year typically follows with New Year’s resolutions. What goals do you have for the New Year? And what strategies could help you to stay on track? Gear up for a power-packed New Year as Josh Leonard and Pete Belcastro from the Leonard Advisory team discuss their resolutions and success strategies! Dive into their reflections on the past year’s triumphs, including Pete’s ca...

How to Stay Safe and Have Fun Doing It with Angela Ferrante and Sam Rosenberg (Ep. 31) 26.12.2023

Do you take your personal safety seriously? What indicators could you be putting out, telling unsavory characters you are a vulnerable target? Discover with Josh Leonard, Angela Ferrante and their guest Sam Rosenberg, founder of Live Ready and the author of “Live Ready: A Guide to Protecting Yourself in an Uncertain World.” Sam debunks some common myths about helplessness and randomnes...

AI’s Impact on Information Retrieval and Career Futures with Michael Laughlin (Ep. 30) 12.12.2023

Are you worried that technology could take over your job? You aren’t the first to feel this way. Whenever technology booms, fear of replacement creeps up. But have you considered the new jobs that this type of evolution opens up? Join Josh Leonard with his guest Michael Laughlin, head of the portfolio specialist team at Morningstar. They explore the potential of AI in various sectors such as finan...

Is Your End-of-Year Financial Checklist Ready? (Ep. 29) 28.11.2023

The end of the year is the perfect time to take stock of your personal finances and make any adjustments that need to be made.  From catching up on retirement contributions to making charitable donations, you have a bit of time left to get everything in order before 2024.  In this episode, Josh Leonard explores end-of-year financial planning. He dives into assessing asset and debt issues, understa...

How Can You Protect Yourself from Identity Theft and Fraud in Retirement? with Pete Belcastro, CFP® (Ep. 28) 07.11.2023

In this episode, Josh Leonard and Pete Belcastro, Financial Planner at Leonard Advisory Group, shine a light on a concerning topic that affects many retirees – identity theft and fraud. Join them as they unveil practical advice that acts as your shield against these modern-day threats. Discover the power of freezing your credit, regularly monitoring your credit scores, and cultivating robust onlin...

Meet the Newest Member of Our Team: Pete Belcastro, CFP® (Ep. 27) 24.10.2023

Get to know another puzzle piece that intertwines perfectly in the Leonard Advisory Group’s growing team… In this episode, Josh Leonard is joined by Pete Belcastro, Financial Planning Consultant at Leonard Advisory Group. Pete shares his journey from cold calling to becoming an investment banker and then a Certified Financial Planner. Pete also discusses his passion for outdoor activities and his...

Can You Harvest the “Fruit” of Volatility? (Ep. 26) 10.10.2023

Discover the secrets of wealth mastery as we unveil strategies that will work for you no matter what your portfolio looks like.  In this episode, Josh unravels essential strategies for navigating uncertain financial landscapes, drawing insights from the practices of the ultra-wealthy and astute investors. Starting with the importance of diversifying a portfolio to mitigate market fluctuations, exp...

Empowering Families in Need: The Story of Christopher’s Kitchen (Ep. 25) 26.09.2023

When you’re in the hospital, the last thing you want to worry about is where your next meal is coming from. That’s the philosophy Christopher’s Kitchen bloomed from.  In this episode, Josh Leonard is joined by Leonard Advisory Group’s very own client and good friend, Carol Hesz. As an ambassador for Christopher’s Kitchen, a nonprofit organization that provides food to families with chi...

How to Choose the Best Place to Retire (Ep. 24) 12.09.2023

Are you questioning whether you want to retire in your home state or venture into a different area during your golden years?  Josh Leonard explores the topic of the best places to retire, depending on an individual’s savings and personal preferences. He explains the important factors to consider when making the decision to relocate such as thinking about the taxes, the cost of living, the proximit...

How Can You Prepare for the Rising Cost of College? with Dan Cieniewicz (Ep. 23) 29.08.2023

As your children get closer and closer to graduation, that education cheque is slowly becoming your reality.  In this episode, Josh Leonard is joined by Dan Cieniewicz aka The College Dude, to discuss all things saving for college. They emphasize the need for parents to come up with a budget and consider sources of funding for college including the FAFSA process and recent changes to it.  Dan and...

Practical Tips for Traveling (Ep. 22) 15.08.2023

Dreaming of world travel but unsure how to do it safely? In this episode, Josh Leonard dives into how you can transition into a retirement life filled with safe, intentional travel. Learn how to embrace the excitement of exploring new places while also ensuring your safety, health, and financial well-being. We’ll cover: Blending in and maintaining a low profile while traveling The importance...

Are You Thinking About Un-Retiring? (Ep. 21) 01.08.2023

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 h...

Overcoming Challenges and Achieving Goals (Ep. 20) 18.07.2023

We’ve got our very own IRONMAN 70.3 Steelhead accomplisher in the studio!  In this episode, Josh Leonard shares his experience completing a half ironman race. Despite facing thunderstorms and a delayed start, Josh was able to swim comfortably and exceed his expectations on the bike leg. He emphasizes the importance of focusing on what you’re good at and enjoy, both in the race and in retirem...

5 Reasons to Ignore the Market When You Retire (Ep. 19) 06.07.2023

Are you worried about the market affecting your retirement plans? In this episode, Josh Leonard talks about five reasons to ignore the market when you retire. He explains each reason and emphasizes the importance of the corresponding retirement planning steps. But ultimately, it’s all about sticking to a long-term plan. Just like climbing a mountain, reaching the peak doesn’t mean you&...

Important Life Lessons Learned: Father’s Day Edition With Bill Leonard (Ep. 18) 13.06.2023

Father’s Day is a great time of the year to reflect on some of the most important life lessons and skills you have learned over the years. In this episode, Josh Leonard invites a VERY special guest on the show, his father, Bill Leonard! Together they discuss some of the unforgettable life lessons and mindset-altering moments that made them into the fathers, professionals, and family men they are t...

Transitioning into Retirement with Jerome Myers (Ep. 17) 06.06.2023

Getting stuck doing the things that you’ve always done just because you’ve always done them is one of the biggest atrocities of life. We have an opportunity each day to make something new and you should make the most of it. In this episode, Josh Leonard brings on Jerome Myers to talk about one of the biggest lifetime transitions, transitioning into retirement. Jerome goes over the key areas of fin...

Money Meets Machine: The Impact of AI in Financial Services (Ep. 16) 23.05.2023

In a world where AI is slowly taking over our everyday lives, it is important to understand what exactly this technology is and how it may be beneficial to a number of different aspects of your life.  In this episode, Josh discusses new AI ventures such as Chat GPT and how some of our everyday devices may not be so far from it. He shares the different ways this technology could be leveraged to ser...

Protecting Yourself from a Bank Collapse: Silicon Valley Case (Ep. 15) 09.05.2023

After the Silicon Valley Bank’s collapse, a lot of people panicked and started doubting the stability of their own banks where they hold accounts. What is the difference between investing in a bank and depositing in it? Are my deposits insured? What can I do if I fear that my bank will collapse? In this episode, Josh Leonard addresses the collapse of Silicon Valley Bank, what happened, and h...

Spring Cleaning! 10 Tips to Clean up your Finances (Ep. 14) 18.04.2023

As the flowers bloom, the grass gets greener and our worries feel lighter, we know that spring is around the corner. You’re probably cleaning out your closets this spring or your garden beds but we’re going to talk about financial spring cleaning as this is a great time to get organized. It is a process of organizing your finances and reviewing your financial position. It can help find...

Your Recession Survival Guide (Ep. 13) 14.03.2023

Have you been in a sticky situation where you needed to pay a large amount of money but did not have liquid assets on hand? With price increases on basic necessary items, it is time to start thinking smarter, not harder.  In this episode, Josh Leonard outlines a number of saving strategies you can start incorporating into your daily life now, to combat the stressors that come with surviving the cu...

Income Planning: When The Paychecks Stop (Ep. 12) 21.02.2023

What do YOU view as your most substantial asset that allows you to live the life you want to live on a daily basis? In this episode, Josh Leonard talks about the road you have to follow once your paychecks stop coming in. Is your life going to run the same? How do you feel confident in your bank account when that number stops increasing? Where is all your money going to come from? Josh alleviates...

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