Shows
Relax, It’s Retirement PodcastFrom Success to Strategy: Planning With Intent for High Earners (Ep. 105)If you have ever thought, “I make good money, so why does this still feel complicated?”, you are not alone.
In this episode, Josh Leonard breaks down why higher income often brings more friction, not less, and why success can quietly add complexity to your financial life if it is not coordinated with intention.
In this episode, Josh walks through what he commonly sees with high earners who are capable, driven, and successful, but short on time. As income grows, financial systems tend to layer on bonuses, equity compensation, multiple accounts, real estate, and tax expo...
2026-02-0325 minRelax, It’s Retirement PodcastSetting SMART Goals: From New Year’s Resolutions to Real Retirement Readiness (Ep. 104)Big goals often feel exciting at the start, but how many actually make it past February? What separates the intentions that fade from the habits that last?
In this episode, Josh Leonard breaks down the SMART goal framework and shares his personal goals for the year, from conquering Pittsburgh’s Dirty Dozen bike race to building non-negotiable daily habits. He explains how this same intentional approach applies to retirement planning and why clarity creates confidence when preparing for your next chapter.
Key points:
How the SMART framework turns vague resolutions into achievable goals with cl...
2026-01-2026 minRelax, It’s Retirement PodcastWhen Should High-Net-Worth Retirees Take Social Security? (Ep. 102)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...
2025-12-0225 minRelax, It’s Retirement PodcastTaxes, Timing, and the End of the Year: What You Can Still Control (Ep. 101)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 Medicare costs, Josh highlights how intentional planning today can lead to more confidence tomorrow.
Josh shares:
Why year-end tax planning matters and how deadlines impact your financial picture
How to use Qualified Charitable Distributions (QCDs) to meet RMD...
2025-11-1826 minRelax, It’s Retirement PodcastEpisode 100 – A Legacy of Intent (Ep. 100)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 ensu...
2025-10-0728 minRelax, It’s Retirement PodcastTurning High Income Into Lasting Wealth (Ep. 99)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 using charitable giving vehicles and understanding capital gains planning, Josh explains how intentional decisions today can lead to a more tax-efficient retirement tomorrow.
Key takeaways:
The importance of converting “rich” (high income) into true wealth
Maxing out 401(k), IRA, Ro...
2025-09-2331 minRelax, It’s Retirement Podcast6 Tax-Smart Takeaways from the One Big Beautiful Bill Act (Ep. 98)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, he outlines six crucial areas that deserve your attention now.
Josh covers:
How slightly wider tax brackets may still trigger more taxable income due to Social Security inclusion
A new $1,000 charitable deduction for non-itemizers starting in 2026, and...
2025-08-2729 minRelax, It’s Retirement PodcastBikes, Voices & Victories: Changing Lives with Variety’s Tom Baker (Ep. 97)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 disabilities participate in everyday joys like riding a bike, going to the grocery store, or simply being heard.
From adaptive strollers to communication tools, this episode is full of remarkable victories that make a difference close to ho...
2025-08-0632 minRelax, It’s Retirement PodcastRetire with Intent: The True Intent Planning System™ Explained (Ep. 96)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 planning for income, investments, taxes, healthcare, and estate matters, and discusses real-life stories and practical tips for retirees.
Josh discusses:
Optimizing income streams in retirement, including Social Security, pensions, annuities, and bridging any income gaps
Str...
2025-07-2329 minRelax, It’s Retirement PodcastHow Recent Retirement Laws May Affect Your Future (Ep. 95)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 surcharges can affect retirees, especially those who have saved diligently.
Josh also shares practical strategies to prepare for the evolving legal environment without overreacting to proposals.
Josh discusses:
Changes from Secure Acts 1.0 and 2.0, including increased RMD ages and IRA c...
2025-07-0230 minRelax, It’s Retirement PodcastPine Valley Camp: Building Futures, One Child at a Time (Ep. 94)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 of Pine Valley Camp, and Julie Saenz about how retirees can embrace their next chapter by giving back. They explore the transformative power of service, the joys of community involvement, and the lasting impact of shaping young lives through Pine...
2025-06-1149 minRelax, It’s Retirement PodcastCan I Retire This Year? (Ep. 93)Market swings, inflation, and shifting headlines can make retiring this year feel uncertain.
But with the right plan, you don’t need to delay your goals — even in a tough market. Are you prepared financially and mentally for what comes next?
In this episode, Josh Leonard shares how to build a flexible retirement strategy that can weather short-term challenges while aligning with your values and lifestyle. He covers tax-efficient tactics, managing income, and finding purpose beyond work.
Josh discusses:
How the three-bucket system helps reduce stress about timing your retirement
Why proper plan...
2025-05-2126 minRelax, It’s Retirement PodcastShould You Buy, Lease, or Hold? Car Buying Decisions in Retirement (Ep. 92)Buying a car can be exciting, but it can also be financially confusing, especially as you enter retirement.
How do you decide between leasing, buying new, or buying used? What financial factors should retirees consider before making a vehicle purchase?
In this episode, Josh Leonard guides listeners through the key financial and personal considerations when choosing a new vehicle in retirement. He compares leasing with buying, discusses the impact of interest rates, and shares tips to make smarter purchasing choices without breaking the budget.
Josh discusses:
The pros and cons of buying...
2025-05-0735 minRelax, It’s Retirement PodcastRetirement Resilience: How to Protect Your Plan in a Volatile Market (Ep. 91)Worried about market volatility and what it means for your retirement?
You’re not alone. Many people get anxious when their retirement accounts seem to shrink after years of growth.
In this episode, Josh Leonard discusses market volatility and strategies to remain patient. Josh explains what market corrections are, why they happen, and how to prepare for them. He also details the bucket strategy, a method to help individuals handle financial uncertainties without making rash decisions.
Josh discusses:
Navigating market volatility with long-term plans
Understanding market corrections and identifying opportunities
The importance of...
2025-04-1522 minRelax, It’s Retirement PodcastSpring Clean Your Finances: 5 Essential Tips for a Fresh Start (Ep. 90)Are your finances due for a little spring cleaning? Just like airing out your home after winter, it’s time to dust off your financial strategy!
Join Josh Leonard as he dives into five key tips for a fresh start this spring. He explores ways to tidy up old retirement accounts, refresh your financial planning outlook, and manage risk in a market full of surprises.
Josh covers:
Consolidating outdated retirement accounts to cut down on fees and overlap
Reviewing and updating your financial strategy to ensure income sufficiency
Assessing investment risks and considering portfolio ad...
2025-04-0127 minRelax, It’s Retirement PodcastAvoiding the Good Saver Tax Problem with Proactive Planning (Ep. 89)Could saving smart lead to a tax nightmare?
Join Josh Leonard as he unravels the unexpected “Good Saver Tax Problem” that even the most prepared might face.
Josh explores strategies to sidestep surprise tax burdens during retirement. Dive into proactive approaches like phase-based tax stacking and unravel the complexities of Roth conversions, Required Minimum Distributions (RMDs), and the interplay between social security and taxes.
Through real-life scenarios, gain clarity on navigating these financial challenges.
Josh discusses:
The phases of the “Good Saver Tax Problem”
How tax stacking can unexpectedly raise brackets
...
2025-03-1120 minRelax, It’s Retirement PodcastUnpacking Social Security Changes (Ep. 88)Social Security remains a critical foundation for retirement, but recent changes bring new opportunities and challenges for retirees.
What strategies can maximize your Social Security benefits? How do recent legislative changes impact your retirement income plan?
In this episode, Josh Leonard explains the updates to Social Security regulations, including the removal of provisions like WEP and GPO, and their potential impact on retirees. He also shares actionable strategies to optimize benefits and maintain a stable financial future.
Josh discusses:
How Social Security benefits are calculated and ways to maximize them based on r...
2025-02-1819 minRelax, It’s Retirement PodcastPlanning Ahead for Retirement (Ep. 87)Retirement should be a time of fulfillment, not financial stress, yet many retirees face unexpected challenges.
How can you make decisions today that your future self will thank you for? What steps can you take to avoid common retirement regrets and financial pitfalls?
In this episode, Josh Leonard and Pete Belcastro discuss essential retirement planning strategies, from managing healthcare costs to optimizing tax efficiency. They emphasize the importance of flexibility, debt management, and long-term financial preparedness to ensure a comfortable and intentional retirement.
Josh and Pete discuss:
The top financial concerns of...
2025-02-0432 minRelax, It’s Retirement PodcastConquering Retirement Fears with Confidence (Ep. 86)Retirement is a time for celebration, but it often brings up important concerns about money, health, and purpose.
How can you prepare to enjoy this new chapter with peace of mind?
In this episode, Josh Leonard and Pete Belcastro discuss actionable steps to overcome common retirement fears, from financial security to finding joy and meaning beyond work. Whether it’s optimizing Social Security, managing healthcare costs, or staying socially connected, this episode provides key strategies for a rewarding retirement.
Josh and Pete discuss:
How to overcome the fear of running out of sav...
2025-01-2125 minRelax, It’s Retirement PodcastThe Diversification Dilemma: Are Your Investments Really Safe? (Ep. 85)Diversification isn’t just a buzzword—it’s a critical tool for protecting your retirement savings and future security.
This week, Josh Leonard and Pete Belcastro tackle common misconceptions about diversification and share actionable insights on creating a retirement plan that minimizes risk and maximizes opportunities. From portfolio strategies to tax diversification and financial tools, this episode has everything you need to feel confident about your golden years.
Josh and Pete discuss:
Why holding accounts at different firms doesn’t guarantee diversification and how to avoid overlapping investments
How to spread investments across sectors, regions...
2025-01-1430 minRelax, It’s Retirement PodcastMastering the Tax Triangle (Ep. 84)What do taxes and retirement have in common with your happiest Saturday?
In this episode of Relax, It’s Retirement, Josh Leonard invites you to unravel the often confusing world of taxes as you approach your golden years. He dives into the “tax triangle” strategy, offering a simplified perspective on how to categorize your assets for better tax efficiency.
Josh shares tips on navigating taxed always, taxed later, and the coveted taxed never categories, as well as how these can impact your retirement strategy.
Josh discusses:
The Tax Triangle and how it can guide...
2025-01-0723 minRelax, It’s Retirement PodcastThe Five Worlds of Money in Retirement (Ep. 83)Are you prepared for the five worlds of money in retirement?
In this episode of “Relax, It’s Retirement,” Josh Leonard explores the distinct but interconnected areas crucial to a successful retirement plan. He dives into income planning, investment strategies, the importance of health and legacy planning, and of course, those pesky taxes. With real-life examples and practical tips, Josh provides insights on making the most of your social security, planning for long-term care, and optimizing your tax scenarios. He debunks myths about social security and explores ways to ensure your financial future is secure and well-planned.
J...
2024-12-3122 minRelax, It’s Retirement PodcastSetting Goals for a Purposeful Retirement (Ep. 82)Goal setting isn’t just for your career—it’s essential for creating an intentional and fulfilling retirement.
What goals will keep you engaged, active, and satisfied as you transition to this next chapter? How do you plan for a successful financial and personal journey during retirement?
In this episode, Josh Leonard recaps his personal and professional goals while emphasizing the importance of intentional goal-setting.
He explores strategies to maintain motivation, improve well-being, and align your finances with your desired lifestyle. By applying the SMART framework, Josh outlines how retirees can structure their aspirat...
2024-12-2427 minRelax, It’s Retirement PodcastMaking the Most of Holiday Giving in Retirement (Ep. 81)Giving is a joyful part of the holiday season, and retirement offers unique opportunities to make it meaningful.
How can retirees balance financial, personal, and charitable giving during the holidays? How can creative and intentional choices enhance the spirit of giving?
In this episode of Relax, It’s Retirement, Josh Leonard and Pete Belcastro discuss strategies for embracing the joy of giving in retirement, including financial tips, creative gift ideas, and charitable contributions. From smart tax planning to handmade gifts, this episode is packed with practical advice for a thoughtful and budget-friendly holiday season.
...
2024-12-1727 minRelax, It’s Retirement PodcastWhat Kills a Bull Market? Factors that Could Trigger the Next Recession (Ep. 80)What happens when market emotions take over your retirement planning?
Josh Leonard and Pete Belcastro tackle the rollercoaster ride of market trends and how you can prepare for those inevitable twists and turns. They explore the intricacies of bull and bear markets and how these fluctuations impact your financial strategies for retirement. They discuss critical indicators that can predict a market downturn and reason why, despite multiple alarms, a recession hasn’t hit.
Josh and Pete discuss:
(00:50) The current bull market scenario and what it means for your investments
(04:53) Recession indicators – what they are and w...
2024-12-1031 minRelax, It’s Retirement PodcastKnow What You Owe: Essentials for a Secure Retirement (Ep. 78)Are you aware of what you truly owe, and more importantly, own in your financial portfolio?
Join us in this episode of Relax, It’s Retirement, where Josh Leonard and Pete Belcastro dive into the nitty-gritty of financial awareness and planning.
Do you really understand how balancing debts and assets can pave a way for a secure retirement?
They explore the significance of knowing your financial landscape, including debts like car loans and mortgages, and how they weigh against your assets.
They discuss:
The importance of financial awareness: Recognize your curre...
2024-11-2631 minRelax, It’s Retirement Podcast5 Key Tax Opportunities to Capture Before Year-End! (Ep. 77)Are you making the most of your year-end tax planning?
In this episode, Josh Leonard dives into effective year-end tax planning strategies to maximize your savings. Prepare for an insightful discussion on Roth conversions, tax loss harvesting, and charitable giving.
Learn how to navigate potential tax pitfalls and make informed financial decisions before the calendar flips to a new year.
Josh covers:
Roth conversions and their tax advantages
Tax loss harvesting to offset gains
Charitable giving strategies, including QCDs and donor-advised funds
Maximizing deductions for medical expenses
Adjusting withholding for accurate tax pl...
2024-11-1924 minRelax, It’s Retirement PodcastHow to Safeguard Your Identity in Retirement (Ep. 76)Are you protecting yourself from the growing threat of identity theft, especially as you near retirement?
This week on Relax, It’s Retirement, Josh Leonard sits down with Angela Ferrante, Leonard Advisory Group’s in-house expert on identity theft, to shed light on this pressing issue. They delve into the methods used by scammers to target older Americans and discuss practical steps you can take to safeguard your personal information.
Josh and Angela explore:
How identity theft commonly occurs
Red flags that might suggest your identity has been compromised
The importance of credit monitoring and...
2024-11-1229 minRelax, It’s Retirement PodcastManaging Job Loss on the Path to Retirement (Ep. 75)What happens when an unexpected job loss disrupts your retirement plans?
In this episode of Relax, It’s Retirement, Josh Leonard and Pete Belcastro delve into strategies for navigating the economic and emotional turbulence of being laid off near retirement.
They offer essential tips on managing finances, addressing healthcare needs, and maintaining a positive outlook during this challenging transition. Additionally, they bring insightful stories from their experience.
They discuss:
Recognizing and managing emotions post-layoff
Filing for unemployment and understanding severance packages
Healthcare options post-employment
Evaluating financial standing and the sustainability of retirement plans
...
2024-11-0528 minRelax, It’s Retirement PodcastFinancial Planning Strategies to Avoid Costly Mistakes (Ep. 74)Feeling empowered in retirement requires careful planning to avoid unnecessary costs and maximize enjoyment.
Are you prepared to handle debt, taxes, and big life changes in retirement?
Learn how financial strategies can help you manage taxes, pay down debt, and even enjoy your golden years worry-free.
In this episode of Relax, It’s Retirement Josh Leonard and Pete Belcastro dive into the world of financial empowerment through careful planning and smart tax strategies. They explore real-world scenarios, including helping clients navigate unexpected credit card debt and embrace the freedom of spending wisely in retir...
2024-10-2925 minRelax, It’s Retirement PodcastMaximizing Charitable Giving in Retirement (Ep. 73)Charitable giving can be a powerful part of your retirement, and it’s about more than just donations—it’s about making a lasting impact with your finances.
How do you ensure your giving is intentional and efficient? What strategies can help you make the most of your contributions without incurring unnecessary taxes?
Join Josh Leonard and Pete Belcastro as they dive into the fulfilling world of charitable giving and how it can play a critical role in your financial planning.
Learn about the impact of charitable contributions, the importance of a personalized giving...
2024-10-2228 minRelax, It’s Retirement PodcastKey Strategies to Maximize Your Medicare Benefits (Ep. 72)When was the last time your reviewed your Medicare plans?
In this episode of *Relax It’s Retirement*, host Josh Leonard sits down to discuss the ins and outs of Medicare open enrollment. As the leaves turn and the air gets crisper, it’s the perfect time to cozy up and ensure you’re prepared for the year ahead. With open enrollment running from October 15th to December 7th, this discussion is essential listening for anyone looking to navigate Medicare.
Josh discusses:
Understanding Medicare Parts A, B, C, and D and their benefits.
Key dates...
2024-10-1524 minRelax, It’s Retirement PodcastMarket Shifts: How to Stay Informed and Prepared (Ep. 71)As inflation cools, new questions arise about the market’s direction and future economic trends.
How will the Fed’s decisions on interest rates affect your investments? Can the economy withstand reduced inflation without entering a recession?
This week, Josh Leonard and Pete Belcastro dive into the significant shift of investor concerns from inflation to other economic factors, highlighting vital strategies to navigate these changes.
Join them as they discuss how these trends influence your retirement planning, the potential for future rate adjustments, and strategies to protect your investments during market volatility.
Josh...
2024-10-0820 minRelax, It’s Retirement PodcastOvercoming Retirement Fears During Election Season (Ep. 70)Election seasons often bring a wave of anxiety, especially for those nearing retirement.
How do you prepare for potential economic shifts without succumbing to fear? How can you ensure your retirement plan remains robust regardless of political outcomes?
In this episode of Relax, It’s Retirement, Josh Leonard explores how the election results could potentially affect your financial future, and why most fears may be overblown.
Discover practical strategies for setting yourself up to navigate market uncertainties, just in time for the upcoming elections.
Josh discusses:
The real impact of elec...
2024-10-0138 minRelax, It’s Retirement PodcastCapital Loss Harvesting vs. Capital Gain Harvesting: What’s Right for Your Retirement? (Ep. 69)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...
2024-09-2426 minRelax, It’s Retirement PodcastPutting Time on Your Side in Retirement (Ep. 68)Time can still be on your side even in retirement!
In this episode, Josh dives into the fascinating dynamics of time and retirement planning. You’ll learn how to maximize your retirement years by leveraging the power of compounding interest, making strategic investment decisions, and using financial tools like annuities and HSAs to ensure your money lasts. Join us as we explore practical strategies to make the most of this new chapter in your life.
Josh discusses:
03:28) The importance and impact of time and compounding interest in retirement
(06:07) How to manage finances effectively with Cas...
2024-09-1728 minRelax, It’s Retirement Podcast6 Ways to Travel on a Budget in Retirement (Ep. 67)Ready to make your dream retirement travel a reality without breaking the bank?
In this episode, Josh Leonard guides you through six effective strategies for budget-friendly travel during retirement. Learn why flexibility is crucial, how to use points and miles effectively, and the surprising alternatives to traditional accommodations. This is your roadmap to financially savvy and fulfilling travel adventures, specially crafted for retirees.
Josh discusses:
Flexibility around travel dates to find cheap flights
Using credit card points and loyalty programs
Considering alternative accommodations such as Airbnbs or house swaps
Planning your travel budget, tracking e...
2024-09-1032 minRelax, It’s Retirement PodcastOvercoming Obstacles With Grit, Endurance & Family Support (Ep. 66)Are you ready to hear a story about grit, teamwork, and the unexpected turns that can define your journey, whether it’s a race or your retirement plan?
In this episode, Josh recounts his recent journey of conquering the Leadville MTB 100 in the Colorado Rockies, with the invaluable support of his wife Yana Leonard, CIA, MBA, Director of Finance. Alongside tales of determination and grit, Josh and Yana emphasize the remarkable role family support played in achieving this monumental feat. Packed with real-world lessons, hear how Josh navigated unexpected hurdles and triumphed with one crucial lesson – preparation and...
2024-09-0347 minRelax, It’s Retirement PodcastPlanning for an Early and Intentional Retirement (Ep. 65)What if you could retire earlier than you think?
In this episode, Josh Leonard and Pete Belcastro dive into the concept of early retirement with the FIRE (Financially Independent, Retire Early) movement, a lifestyle choice emphasizing extreme savings and smart investments. They provide information about how adopting frugality and strategic financial planning can help set you on a path to early retirement. Josh and Pete cover practical tips on extreme savings, smart investing, and the importance of a frugal yet fulfilling lifestyle.
Josh and Pete discuss:
Overview of the FIRE movement and its focus o...
2024-08-2724 minRelax, It’s Retirement PodcastEstate Planning Essentials (Ep. 64)You can protect your loved ones and legacy as you transition into retirement by estate planning.
Today on Relax, It’s Retirement, host Josh Leonard, and Pete Belcastro dive into the often overlooked but crucial aspect of retirement planning: estate planning. They talk about how to effectively prepare your essential estate documents, avoid the drawbacks of probate, leverage trusts for tax planning, and ensure your loved ones are protected. Tune in for some practical tips and advice around estate planning that can give you peace of mind as you plan for your golden years.
Josh an...
2024-08-2027 minRelax, It’s Retirement PodcastHow to Choose the Best State for Your Retirement (Ep. 63)Where should you retire? Your perfect place could be closer than you think.
Let’s take a look at some factors that could make or break your retirement decision.
Today on Relax, It’s Retirement, Josh Leonard and Pete Belcastro talk about what truly makes a state great for retirement. They dissect a recent study listing the top states for retirement, unpacking factors such as the cost of living, weather, healthcare, and why personal preferences can completely change the ideal location for retirement.
Tune in to learn how to weigh these factors with your...
2024-08-1327 minRelax, It’s Retirement PodcastNavigating RMD Changes for Your Retirement Plan (Ep. 62)Why does the government force you to take money out of your retirement accounts, even if you don’t need it?
In this episode or Relax, It’s Retirement, Josh Leonard and Pete Belcastro dive into the intricacies of Required Minimum Distributions (RMDs) and explain why they are a crucial aspect of retirement planning. Together, they cover recent changes in RMD rules, including the impact of the Secure Act and the importance of understanding how these changes affect your retirement and tax planning.
You’ll learn about the different types of beneficiaries and the rules surround...
2024-08-0627 minRelax, It’s Retirement PodcastHealthcare Costs in Retirement: Strategies to Manage Your Expenses (Ep. 61)Are you struggling to navigate the maze of Medicare and healthcare costs in retirement?
In this episode, Josh Leonard and Pete Belcastro delve into the complexities of healthcare planning for retirees. They discuss understanding Medicare, evaluating different health plans, and the critical steps to prevent unexpected medical expenses. Josh and Pete share valuable insights into Medicare’s parts, long-term care options, and the magical benefits of a Health Savings Account (HSA).
Josh and Pete discuss:
Understanding the intricacies of Medicare parts A, B, C, and D
Evaluating long-term care options and associated costs
Strategies for...
2024-07-3031 minRelax, It’s Retirement PodcastBreaking Financial Rules (Ep. 60)Are you ready to break some financial rules to optimize your retirement planning?
Today, we’re challenging the rules of retirement planning to see when breaking them might actually be in your best interest.
In this episode, Josh Leonard and his partner in crime, Pete Belcastro dive into five conventional financial rules that many believe are set in stone but might be worth reconsidering to better fit individual needs. They discuss why paying off your mortgage before retirement, avoiding credit cards, and rigidly maintaining a budget might not always be the best advice. Instead, they of...
2024-07-2329 minRelax, It’s Retirement PodcastLongevity in Retirement: Planning for the Long Haul (Ep. 59)Are you ready to make your retirement last for the long haul?
In this episode of Relax, It’s Retirement, Josh Leonard and Pete Belcastro discuss the importance of longevity in retirement. They cover strategies for structuring your assets to ensure they last, the importance of tax planning, and tips for maintaining an active and fulfilling lifestyle throughout your retirement years. Learn about the three-bucket strategy for managing your funds, the importance of tax-efficient planning, and how staying active and socially engaged can enhance your quality of life.
This episode is packed with valuable tips and...
2024-07-1626 minRelax, It’s Retirement PodcastConnecting Community and Retirement Through Art with Tami Fauver (Ep. 57)Art isn’t just for galleries – it’s a powerful tool for enriching your retirement experience. Have you ever thought about how art could transform your retirement?
Today on Relax, It’s Retirement, Josh introduces Tami Fauver, the Executive Chief and Curator at Krasl Art Center. They explore the dynamic intersection of the arts and retirement and discuss how Krasl Arts Center has become a cornerstone for both aspiring artists and retirees looking to give back and stay engaged. Learn how art fairs, community engagement, and creative expressions can shape a fulfilling retirement. Tami and Josh converse about the...
2024-07-0235 minRelax, It’s Retirement PodcastFOMO in Retirement Planning, Explained (Ep. 56)Are your financial decisions driven by a fear of missing out (FOMO)?
Get ready to conquer your retirement planning with confidence and ease.
Today on Relax, It’s Retirement, Josh Leonard and Pete Belcastro discuss retirement planning with a focus on overcoming the fear of missing out (FOMO) and making informed decisions for a secure financial future. They explain why staying true to your disciplined investment strategy is crucial, especially in the face of trending financial fads like meme stocks and cryptocurrency.
Josh and Pete talk about:
FOMO’s impact on retirement plann...
2024-06-2531 minRelax, It’s Retirement PodcastRetirement Planning: Preparation, Adaptability & Doing Hard Things (Ep. 55)What does it take to truly conquer life’s toughest challenges and apply those lessons to your retirement?
This week on Relax It’s Retirement, Josh Leonard and Pete Belcastro dive into the topic of “doing hard things” and how taking on challenges can prepare you mentally and emotionally for retirement. Josh shares an inspiring anecdote about a grueling bike ride up Maui’s Haleakala volcano, and they explore parallels between physical endurance and financial preparedness. They discuss why staying active and engaged matters even after retirement, offering insights on setting goals, planning effectively, and remaining adaptable.
Josh...
2024-06-1731 minRelax, It’s Retirement PodcastHow to Save for Retirement 101 (Ep. 54)Ever wondered how to effectively save for retirement without missing out on the joys of life today?
Today on Relax, It’s Retirement, Josh Leonard shares invaluable tips about optimizing your savings strategy during the accumulation phase of your finances. Whether you’re just starting or looking to refine your approach, this episode demystifies the order of saving money, and ensuring a balanced lifestyle while preparing for a secure future. He navigates through practical advice on emergency funds, the power of employer matches in retirement accounts, and the strategic use of HSAs and IRAs for long-term benefits.
2024-06-1126 minRelax, It’s Retirement PodcastIs Social Media Misleading You on Finance? (Ep. 53)Are you being hoodwinked by financial advice on social media?
In today’s episode of Relax, It’s Retirement, Josh Leonard delves into the murky waters of financial advice on social media platforms. With special attention on the credibility of so-called financial influencers, or ‘finfluencers,’ Josh unpacks the allure of simplicity in managing finances that social media tends to promise. He explores how the ease and accessibility of social media content can often misguide individuals when making crucial financial decisions.
Josh discusses:
The impact of social media on financial decisions
Distinguishing credible financial advice from sensa...
2024-06-0422 minRelax, It’s Retirement PodcastAre You Ready to Retire? (Ep. 52)Are you ready for retirement? How much money do you need to ensure your golden years are truly golden?
Today on Relax It’s Retirement, Josh Leonard and Pete Belcastro address essential considerations for anyone nearing retirement. From understanding the right time to retire to strategically managing retirement income, this conversation aims to equip you with the knowledge to navigate financial decisions with confidence. Whether it’s determining if your savings are sufficient, dealing with market fluctuations, or making smart investment choices, this episode covers the groundwork for a fulfilling retirement journey.
Josh and Pete disc...
2024-05-2833 minRelax, It’s Retirement PodcastDecoding Life Insurance for Retirees: Is It Essential? (Ep. 51)How does life insurance fit into your retirement plan? Is life insurance still relevant in retirement?
This week on Relax It’s Retirement, Josh Leonard and Pete Belcastro discuss whether or not life insurance is necessary in retirement. They cover four main reasons to own life insurance in retirement: covering debts, preserving family assets, covering long-term care expenses, and leaving a tax-free legacy. They also mention the importance of planning and working with a financial advisor to determine the best approach for individual needs. From protecting your loved ones to planning for unforeseen medical expenses, this conversation is...
2024-05-2122 minRelax, It’s Retirement PodcastMastering Financial Literacy in Your Golden Years: Part 2 (Ep. 50)Transitioning into retirement could feel just as sunny and relaxed as a perfect summer day, but like spending a day in the sun, you’ve got to plan for all weather factors when it comes to retirement or risk feeling a little burned.
Today on Relax, It’s Retirement, Josh Leonard and Pete Belcastro delve into part two of financial literacy for your golden years with a focus on government benefits and tax planning. In addition to managing required minimum distributions and the timing of Social Security benefits, the conversation also navigates through estate planning and the cons...
2024-05-1431 minRelax, It’s Retirement PodcastBuilding a Legacy Through Smart Retirement and Giving Strategies with Jack Miller (Ep. 49)Many believe that impactful philanthropy is exclusive to the ultra-rich. However, strategic charitable giving is accessible to a wide range of donors.
In this episode, Josh Leonard is joined by philanthropy expert Jack Miller, principal of Miller Consulting, for a conversation about how strategic charitable giving can be a cornerstone of your financial planning and legacy. Jack shares his personal journey, blending faith, philanthropy, and financial strategy, to provide listeners with a roadmap to creating a legacy that resonates through generations. Discover the synergy between tax-efficient philanthropy and fulfilling retirement goals, reinforced by Jack’s rich experiences an...
2024-05-0737 minRelax, It’s Retirement PodcastMastering Financial Literacy in Your Golden Years (Ep. 48)Are you ready to greet retirement with a well-prepared smile?
Welcome to the Relax, It’s Retirement podcast, where we dive into mastering financial literacy in your golden years. This episode, featuring Josh Leonard and Pete Belcastro, zooms in on transitioning into retirement with intent. They explore practical tips for income and budget planning in April’s Financial Literacy Month, highlighting ways to navigate the shift from a steady paycheck to managing retirement funds. Through engaging discussions and real-life examples, you will glean insights into making informed decisions for a fulfilling retirement.
Josh and Pete disc...
2024-04-3029 minRelax, It’s Retirement PodcastMaking an Impact with Donor-Advised Funds ft. Daffy.org CEO Adam Nash (Ep. 47)Are you struggling to navigate the complexities of charitable giving and tax planning for retirement?
Let us introduce you to Daffy!
Josh Leonard and his guest, Adam Nash, co-founder and CEO of Daffy.org dive into the world of donor-advised funds, money decisions, and much more on this engaging episode of Relax It’s Retirement. They address how Daffy can help simplify your giving and give you more control over your charitable donations. Take the stress and guesswork out of charitable giving, allowing you to support causes you care about with ease while maximizing your ta...
2024-04-2342 minRelax, It’s Retirement PodcastMaximize Your Retirement: 3 Reasons to Consider Roth Conversions (Ep. 46)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 fu...
2024-04-1623 minRelax, It’s Retirement PodcastJuggling Retirement & College Debt with Dan Cieniewicz (Ep. 45)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 Parent PLUS loans...
2024-04-0933 minRelax, It’s Retirement PodcastNavigating Financial Storms: Lessons from Market Meltdowns (Ep. 44)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...
2024-04-0233 minRelax, It’s Retirement PodcastEmpowering Women in Retirement: The Legacy of Barbara Hillary (Ep. 43)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, inspiring others along the way...
2024-03-2627 minRelax, It’s Retirement PodcastAre Behavioral Biases Affecting Your Retirement Planning & Investment Decisions? (Ep. 42)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:
Loss aversion and its impact on investment decisions
Confirmation bias and its influence on perceptions and decision-making
Herd me...
2024-03-1925 minRelax, It’s Retirement PodcastDon’t Let Taxes Crash Your Party – How to Maximize Your Tax Savings with Pete Belcastro, CFP® (Ep. 40)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 str...
2024-03-0531 minRelax, It’s Retirement PodcastNavigating Life’s Twists and Turns: A Candid Conversation with Yana Leonard | Family, Finance, and More (Ep. 39)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 pand...
2024-02-2741 minRelax, It’s Retirement PodcastNavigating Post-Employment 401(k) Options (Ep. 38)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 the optio...
2024-02-2027 minRelax, It’s Retirement PodcastThe Three-Bucket Strategy for Retirement Planning with Pete Belcastro (Ep. 37)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...
2024-02-1327 minRelax, It’s Retirement PodcastSeven Steps to Successful Retirement (Ep. 36)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 discusses:
What is the first step in building a successful retirement plan
When should you start tax planning for retirement
Why is understanding Social Security important for retirement
How do you a...
2024-02-0623 minRelax, It’s Retirement PodcastBuilding Memorable Culture Moments at Work with Eric Leathem (Ep. 35)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 contributed to the personal growth and well-being of the employees.
Josh and Eric discuss:
What is Eric’s background and history of work with the firm
Personal anecdotes and experiences within...
2024-01-3029 minRelax, It’s Retirement PodcastManaging the Unpredictability in Market Predictions for Investment Planning with Pete Belcastro, CFP® (Ep. 34)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 year. They tackle the whole issue of bank failures and what that means for our wallets.
Josh and Pete discuss:
Why are market predictions not always the most reliable
Where has the imp...
2024-01-2333 minRelax, It’s Retirement PodcastRefine Your Financial Goals for Retirement with Lists (Ep. 33)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 a secure and fulfilling retirement. Don’t miss out on this insightful discussion that can reshape your approach to financial planning in the New Year.
Josh dis...
2024-01-1623 minRelax, It’s Retirement PodcastAchieving and Setting Goals with Pete Belcastro, CFP® (Ep. 32)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 career eureka moment and Josh conquering a half ironman. Uncover the secrets behind their goal-setting choices and the winning strategies that propelled them to achievement.
Get ready to be inspire...
2024-01-0934 minRelax, It’s Retirement PodcastHow to Stay Safe and Have Fun Doing It with Angela Ferrante and Sam Rosenberg (Ep. 31)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 randomness in violence, sharing valuable advice on personal security and self-defense techniques.
Sam discusses:
When does learned helplessness have an impact on society
Where can danger be recognized and managed
Why is it important to ha...
2023-12-2635 minRelax, It’s Retirement PodcastAI’s Impact on Information Retrieval and Career Futures with Michael Laughlin (Ep. 30)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 finance, marketing, software development, and healthcare, emphasizing that AI will never fully replace the human element, which is crucial to decision-making and building relationships.
Michael discusses:
Wha...
2023-12-1232 minRelax, It’s Retirement PodcastIs Your End-of-Year Financial Checklist Ready? (Ep. 29)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, understanding tax implications, maximizing contributions to tax-advantaged accounts, and more. Josh also explains the benefits of gifting money to avoid estate taxes and the importance of financial aid planning for ch...
2023-11-2822 minRelax, It’s Retirement PodcastHow Can You Protect Yourself from Identity Theft and Fraud in Retirement? with Pete Belcastro, CFP® (Ep. 28)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 online security habits. Our experts leave no stone unturned to ensure you’re well-prepared for the challenges that may arise.
But it’s not just about digital defense. Josh and Pete emphasize the significance of mainta...
2023-11-0727 minRelax, It’s Retirement PodcastMeet the Newest Member of Our Team: Pete Belcastro, CFP® (Ep. 27)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 dedication to community service.
Josh and Pete chat about:
Pete’s personal background, including being a Pittsburgh native and a sports fan
Pete’s career journey into the world of financial planning and invest...
2023-10-2423 minRelax, It’s Retirement PodcastCan You Harvest the “Fruit” of Volatility? (Ep. 26)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, exploring options like fixed income and advanced strategies. We then delve into the concept of “dry powder” and how it empowers investors to seize opportunities without unnecessary trading. Advanced tax planning steps are also unveiled, offering potential avenues to maximize tax a...
2023-10-1024 minRelax, It’s Retirement PodcastEmpowering Families in Need: The Story of Christopher’s Kitchen (Ep. 25)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 children in the hospital, Carol shares how she got involved with the organization and her role in organizing food drives and fundraising events. She offers her experience with the need for access...
2023-09-2624 minRelax, It’s Retirement PodcastHow to Choose the Best Place to Retire (Ep. 24)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 proximity to family and friends and more.
In this episode, Josh covers:
How to research the cost of living for the place you desire to relocate to
Getting to k...
2023-09-1225 minRelax, It’s Retirement PodcastHow Can You Prepare for the Rising Cost of College? with Dan Cieniewicz (Ep. 23)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 Josh discuss:
Retirement benefits grandparents can receive through paying for their grandchildren’s education
The challenge of integrating grandparents into the conversation about college funding
The import...
2023-08-2933 minRelax, It’s Retirement PodcastPractical Tips for Traveling (Ep. 22)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 of having an emergency plan and what it should include
The essentials of a travel first aid kit
The need for short-term travel insurance and its implications
Why digital copies of...
2023-08-1525 minRelax, It’s Retirement PodcastAre You Thinking About Un-Retiring? (Ep. 21)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...
2023-08-0120 minRelax, It’s Retirement PodcastOvercoming Challenges and Achieving Goals (Ep. 20)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 retirement. Despite setbacks, including a shelter-in-place order, Josh remained determined to complete the race.
Josh discusses:
The key takeaways from his training
Reflections on the value of accepting unexpe...
2023-07-1823 minRelax, It’s Retirement Podcast5 Reasons to Ignore the Market When You Retire (Ep. 19)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’re done. Your investments need time to grow. So, relax and tune in to learn more about creating a solid financial plan so you can ignore the market.
The 5 reasons Josh discusses:
You...
2023-07-0626 minRelax, It’s Retirement PodcastImportant Life Lessons Learned: Father’s Day Edition With Bill Leonard (Ep. 18)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 today.
Josh and Bill discuss:
The mindset each of them was taught about work early in life and how it influenced their work ethic
How the...
2023-06-1328 minRelax, It’s Retirement PodcastTransitioning into Retirement with Jerome Myers (Ep. 17)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 finding your next chapter in life and explains the significance of an “and” instead of an “or” lifestyle, the importance of prioritizing authenticity, how you can find your ne...
2023-06-0632 minRelax, It’s Retirement PodcastMoney Meets Machine: The Impact of AI in Financial Services (Ep. 16)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 serve our clients better.
Josh discusses:
Some benefits AI might bring to your job and everyday life
The number of di...
2023-05-2326 minRelax, It’s Retirement PodcastProtecting Yourself from a Bank Collapse: Silicon Valley Case (Ep. 15)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 how it affected their clients and investors. He talks about how FDIC insurance works for our deposits, and what we can do to protect ourselves if ou...
2023-05-0922 minRelax, It’s Retirement PodcastSpring Cleaning! 10 Tips to Clean up your Finances (Ep. 14)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 areas to save money, reduce expenses and improve your retirement.
In this episode, Josh Leonard discusses 10 different ways you can clean up your finances to get ready for...
2023-04-1834 minRelax, It’s Retirement PodcastYour Recession Survival Guide (Ep. 13)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 current recession.
Josh discusses:
Some key tips for saving your money while prices hike up
Rising along with interest rates – locking in higher retirement rates...
2023-03-1423 minRelax, It’s Retirement PodcastIncome Planning: When The Paychecks Stop (Ep. 12)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 all of these stressors in detail.
Josh discusses:
How life expectancy can determine the plan you create for y...
2023-02-2125 minRelax, It’s Retirement PodcastSecure Act 2.0: What does it mean for you? (Ep. 11)The Secure Act 2.0 was signed into place on December 23, 2022. This opens several new strategies you can dip into, in order to save for your retirement and/or fund important goals such as education.
In this episode, Josh Leonard discusses the number of changes this act has brought forward to us so that we can save more money more efficiently. Whether you are in the planning stage of your retirement or are looking into the future to understand how to further your savings, this episode will help you move forward.
Josh discusses:
What this act mean...
2023-02-0720 minRelax, It’s Retirement PodcastLet’s Talk About Risk (Ep. 10)What is your biggest fear? Many times our fears don’t align with our biggest risks. Market risk has been on the top of everyone’s mind but that is not the only risk we need to worry about in retirement.
In this episode, Josh Leonard discusses what risks you should be wary of when preparing and in retirement. Due to the recent market activity, everyone’s been worried about the stock market, but that might not be the biggest risk you might be facing in your financial life.
Josh discusses:
Common risks we might no...
2023-01-1731 minRelax, It’s Retirement PodcastGoal Setting for the New Year (And How to Stay Accountable) (Ep. 9)New year, new you… At least until around March.
Isn’t that always how it goes? Most of us set some goals but fall off the wagon not too long after. We get it.
In this episode, Josh Leonard talks about the challenges of staying accountable and on track with your New Year’s resolutions. He shares some tips and tricks for how to overcome these VERY common challenges.
Josh discusses:
His New Year resolutions and how he plans to stay on track for achieving them
The SMART goals framework, how it works a...
2023-01-0327 minRelax, It’s Retirement PodcastGifts of Financial Wisdom for Your Grandkids (Ep. 8)Looking for last-minute gift ideas for your Grandkids? Look no further! Although they might be looking for fun toys, it might be time to offer them the gift that keeps on giving; a solid financial foundation.
In this episode, Josh Leonard is joined by Bill Leonard, father and founder of the Leonard Advisory Group. As the holiday season is sneaking up on us, it might be time to start thinking about some non-traditional gifts you can offer your children. These gifts can aid in the stability of their financial future, whether that is opening a savings account f...
2022-12-2024 minRelax, It’s Retirement Podcast5 Hidden Year-End Tax Saving Strategies (Ep. 7)2022 has been a challenging year, to say the least. From the war in Ukraine, inflation and elections to the downward shift in the market, there are a number of factors coming together, causing us to stress about our finances. Thankfully, the year is not over yet and we have a few effective strategies that might save you tax-free money.
In this episode, Josh Leonard discusses five hidden tax-saving opportunities you may want to take advantage of before year-end.
Josh dives into:
How to get more tax-free money
Making savvy retirement planning moves
Being charitable, skip...
2022-12-0622 minRelax, It’s Retirement PodcastClient Retirement Story: Cycling Across the USA with Al Miller (Ep. 5)Are you unsure what your retirement will look like? Finding new passions at an old age can be challenging but finding an activity that releases your serotonin like never before can jumpstart you into a fulfilling retirement, living out your days to the fullest.
In this episode, Josh Leonard is joined by Al Miller, an avid cyclist who completed his ride across the US last year that he blogged live, where he averaged 350 viewers per day with a grand total of 18,000 viewers in 16 different countries. He dives into where his passion for cycling started and how he...
2022-11-0829 minRelax, It’s Retirement PodcastTricks and Treats for Retirement This Halloween Season (Ep. 4)As we get our front porches wrapped with spider webs and observe the leaves changing colors, it might be a good time to take one step forward in your retirement planning.
In this episode, Josh Leonard discusses some tricks and treats for retirement along with all the planning that goes into it as we head into the final quarter of the year. Additionally, he explains some ways to develop an efficient plan to take advantage of current market conditions, prepare for recessions before they come, and make smart health and tax decisions.
Josh discusses:
Ho...
2022-10-2525 minRelax, It’s Retirement PodcastMeet the Dream Team at Leonard Advisory Group with Bill Leonard, Angela Ferrante and Desiree Hoosac (Ep. 3)With the large number of clients under our belt, we pride ourselves in adapting and catering to any of our client’s needs, in any circumstances. This is why we work with trusted professionals, as well as other partnered firms such as AE Wealth Management and Morningstar Investment Management.
In this episode, Josh Leonard is joined by some of the key players from his team: Angela Ferrante, Desiree Hoosac and the founder of Leonard Advisory Group, Bill Leonard. They explain what you can expect while working with them as you plan your retirement. Additionally, they talk about som...
2022-10-1128 minRelax, It’s Retirement PodcastRetiring With Intent (Ep. 2)Retirement looks different for many people. For some, it might be slowing down, taking your foot off the gas, and leaning back into a more relaxed lifestyle. For others, it may be continuing to work part-time but focusing on passions rather than a career. An intentional retirement can kickstart this process for you through planning ahead early and identifying your goals.
In this episode, Josh Leonard details the retirement planning process at Leonard Advisory Group. He explains how they mentor and guide their clients by the breakdown of INTENT – I (yourself), Needs, Taxes, Endowment, Navigating Financial Tools, and...
2022-10-1123 minRelax, It’s Retirement PodcastA Father & Son Legacy: Meet the Leonards (Ep. 1)Retirement may pose many questions, but you can make the most of this next chapter of your life by preparing for it intentionally.
And you’re in the right place if you’re wondering how.
Introducing the Hello Retirement podcast with Josh Leonard.
In this inaugural episode, Josh Leonard is joined by the father of the Leonard Advisory Group, Bill Leonard who also happens to be his father and real-life mentor during his shift to the financial services industry.
Bill and Josh share:
Stories of how each of them started in the f...
2022-10-1129 min