Relax, It’s Retirement Podcast

Most people don’t have a bad retirement plan; they just haven’t tested it yet. In this episode, Josh Leonard walks through what it really means to pressure-test your retirement plan before you step away from work. Using a real client story, he breaks down how a plan that looks solid on paper can still carry hidden risks if it hasn’t been coordinated across income, taxes, investments, healthcare, and legacy. Josh shares how small adjustments, like restructuring investments into purpose-driven “buckets,” planning for tax-efficient withdrawals, and reviewing beneficiary designations, can make a meaningful difference over time. He also highlights how overlooking factors like Medicare decisions or account structure can lead to unnecessary costs later. This conversation is a reminder that retirement isn’t just about how much you’ve saved; it’s about how everything works together when you need it most. Josh discusses:  Why retirement plans need to be stress tested, not just built The “bucket strategy” for income, cash, and growth How market downturns early in retirement can impact long-term outcomes Hidden tax risks and how to think about withdrawals more intentionally And more! Resources: Schedule a meeting with the team Connect with Josh Leonard:  [email protected] LinkedIn: Josh Leonard Leonard Advisory Group 412-998-PLAN YouTube: Leonard Advisory Group Facebook: Leonard Advisory Group

Markets move fast, headlines move faster, and emotions often follow. So how do you stay grounded when uncertainty feels constant and every decision seems urgent? In this episode, Josh Leonard speaks with Dominic Pappalardo, Chief Wealth Strategist at Morningstar Wealth, about maintaining discipline during volatile markets. They break down a bucket-based investment approach, the importance of long-term thinking, and why reacting to headlines can hurt outcomes. Dominic also shares insights on missing key market days, evaluating AI valuations, and how bonds and sector dispersion are shaping current opportunities. Key takeaways: Why structuring portfolios into cash, income, and growth buckets helps reduce emotional decisions Missing just a few key trading days can significantly impact long-term returns and outcomes AI growth remains strong, but long-term value depends on real returns from adoption by businesses Bonds now offer better income support compared to prior years due to higher starting yields Market opportunities often come from gaps between pricing and fundamentals across sectors And more! Resources: Schedule a meeting with the team Connect with Josh Leonard:  [email protected] LinkedIn: Josh Leonard Leonard Advisory Group 412-998-PLAN YouTube: Leonard Advisory Group Facebook: Leonard Advisory Group Connect with Dominic Pappalardo: LinkedIn: Dominic Pappalardo Website: Morningstar  About our Guest:  Dominic Pappalardo is chief multi-asset strategist for Morningstar Wealth. He plays a crucial role as a public-facing ambassador to a variety of media channels. His work ensures that complex asset class views, macroeconomic insights, and portfolio positioning are communicated effectively to a wide range of audiences. Dominic leads the production of insightful commentary and research intended to engage and inform a diverse client base. Acting as a vital link between the investment team and clients, he is instrumental in enhancing visibility and engagement around the firm’s highest conviction ideas. Internally, he collaborates closely with the portfolio management and research teams to maintain cohesion in macroeconomic perspectives and asset class views, delivering a unified narrative to stakeholders. Advisory services under Morningstar Wealth are offered by Morningstar Investment Management LLC, a registered investment adviser and subsidiary of Morningstar, Inc. Before joining Morningstar in 2020, Pappalardo cultivated nearly two decades of experience managing all facets of fixed income strategies at McDonnell Investment Management, an affiliate of Natixis Investment Managers. Pappalardo holds a B.B.A. in Finance from Benedictine University. He also holds an M.B.A from The University of Notre Dame’s Mendoza College of Business.

A tax return can reveal more than what happened last year; it can point to choices that may help reduce friction and improve retirement income over time. What hidden issues could be sitting in your paperwork, and what small moves today could help you avoid bigger tax headaches later? In this episode, Josh Leonard explains how a closer look at your tax return can uncover planning opportunities before they grow into larger retirement issues. He covers phantom gains in taxable accounts, why a 0% tax bill can still create future problems, and how tax bracket planning matters before required distributions begin. Josh also walks through charitable giving strategies, including new 2026 deduction rules and qualified charitable distributions for IRA owners. Key takeaways: Why phantom gains from mutual funds can create taxable income even when your account balance declines overall How a 0% tax return may hide a future jump into higher brackets once pensions and RMDs begin later on Why reviewing taxable income sources can reveal avoidable drag from dividends, rebalancing, and fund sales How Roth conversions can help spread taxes across retirement years instead of pushing income into later spikes Why charitable gifts may be more effective through new deductions or direct IRA transfers after age 70 and a half And more! Resources: Schedule a meeting with the team Connect with Josh Leonard:  [email protected] LinkedIn: Josh Leonard Leonard Advisory Group 412-998-PLAN YouTube: Leonard Advisory Group Facebook: Leonard Advisory Group

What if “just one more year” at work costs you more than it gives you? In this episode, Josh Leonard challenges one of the most common retirement assumptions, the idea that working one more year is always the safer choice. While extra income can feel reassuring, delaying retirement can quietly take time, health, energy, and meaningful experiences you may never get back. Josh walks through real client stories and practical planning scenarios that show why one more year is often an emotional decision, not a financial one. He introduces a simple trade-off filter to help listeners evaluate whether delaying retirement truly improves their plan or simply postpones living the life they’ve already earned. Josh discusses: Why being financially ready does not always make retiring emotionally easy How taxes, required distributions, and healthcare can change the math The hidden cost of delaying retirement when time and health are limited A three-question framework to evaluate if one more year actually helps How intentional income planning creates confidence to retire sooner And more! Resources: Schedule a meeting with the team Connect with Josh Leonard:  [email protected] LinkedIn: Josh Leonard Leonard Advisory Group 412-998-PLAN YouTube: Leonard Advisory Group Facebook: Leonard Advisory Group

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 exposure. None of these are mistakes, but without a clear framework, small inefficiencies can build up and slow progress toward retirement. Josh discusses: Why success rarely simplifies finances on its own How “financial friction” shows up through taxes, concentration risk, and misaligned accounts The role of coordination across investments, taxes, income, healthcare, and estate planning Why having money does not always mean having liquidity How planning with intent helps decisions reinforce each other instead of working against each other And more! Resources: Schedule a meeting with the team Connect with Josh Leonard:  [email protected] LinkedIn: Josh Leonard Leonard Advisory Group 412-998-PLAN YouTube: Leonard Advisory Group Facebook: Leonard Advisory Group

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 clear benchmarks and timelines Josh’s three major goals for the year and the specific training, habits, and preparation each requires Why knowing your monthly expenses is the first step in any meaningful retirement plan How hobbies and projects in retirement create purpose beyond simply not working anymore The importance of aiming high and tracking progress, even when life gets in the way And more! Resources: Schedule a meeting with the team Connect with Josh Leonard:  [email protected] LinkedIn: Josh Leonard Leonard Advisory Group 412-998-PLAN YouTube: Leonard Advisory Group Facebook: Leonard Advisory Group

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, mindset, and the importance of thinking ahead. He talks about the parallels between physical endurance and retirement planning, the value of support systems, and how steady habits create a more intentional life.  Key points: Planning missteps that made the Austin race tougher, and why preparation shapes outcomes How heat, hydration, and equipment choices influenced the long ride and its lessons Why support systems matter when facing difficult moments or big goals How intentional preparation mirrors the steps needed for retirement planning The value of seeking growth at every stage of life and staying engaged And more! Resources: Schedule a meeting with the team Connect with Josh Leonard:  [email protected] LinkedIn: Josh Leonard Leonard Advisory Group 412-998-PLAN YouTube: Leonard Advisory Group Facebook: Leonard Advisory Group

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 Insights: Why higher savings create more flexibility around Social Security timing How IRMAA can affect Medicare costs when income rises unexpectedly How delaying benefits can lower long-term risk and support lifetime income How portfolio restructuring reduces unnecessary taxes from mutual fund gains Why Social Security choices must connect with tax, investment, and legacy planning And more! Resources: Schedule a meeting with the team Connect with Josh Leonard:  [email protected] LinkedIn: Josh Leonard Leonard Advisory Group 412-998-PLAN YouTube: Leonard Advisory Group Facebook: Leonard Advisory Group

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 requirements while supporting meaningful causes What to do if you face the “good saver tax problem” and want to pass wealth efficiently to the next generation How Roth conversions and new senior deductions can help balance taxes in retirement Why managing IRMAA limits can prevent unexpected Medicare cost increases And more! Resources: Schedule a meeting with the team Attend One of Our Educational Events Connect with Josh Leonard:  [email protected] LinkedIn: Josh Leonard Leonard Advisory Group 412-998-PLAN YouTube: Leonard Advisory Group Facebook: Leonard Advisory Group

When you hit a milestone, you pause to reflect. In this special 100th episode, Josh Leonard is joined by his father, Bill Leonard, whose work laid the foundation of what is now the Leonard Advisory Group. Together, they revisit the firm’s humble beginnings, envelopes licked in a basement, meetings around kitchen tables, and the evolution into a practice that now helps hundreds of families retire with clarity and confidence. Key takeaways: How Bill transitioned from architecture to financial advising Family lessons that shaped Leonard Advisory Group’s mission Stories of clients whose planning ensured lasting comfort The importance of foresight over hindsight in retirement And more! Resources: Schedule a meeting with the team Connect with Josh Leonard:  [email protected] LinkedIn: Josh Leonard Leonard Advisory Group 412-998-PLAN YouTube: Leonard Advisory Group Facebook: Leonard Advisory Group Connect with Bill Leonard: LinkedIn: Bill Leonard About our Guest:  William Leonard laid the foundation for  the  Leonard Advisory Group to fill in the gaps he saw when helping his mother plan for retirement. Bill focused much of his career on the insurance and annuity industry. As an independent advisor, he helped thousands of retirees and pre-retirees face the financial challenges that lie ahead with confidence. Since 1996, Bill has worked in a variety of capacities, gaining valuable experience with insurance. In 2007, he became an independent consultant, focusing on income protection and retirement planning. Bill was an honorary host of the “Protecting Your Profits” radio show on 94.5 3WS Pittsburgh and a weekly guest on the national broadcast “Financial Safari” radio show heard locally on NewsTalk 104.7 FM. He has also been featured on WISR 680 AM and WORD FM. In his free time, Bill enjoys traveling, boating, skiing, hiking, biking, restoring antique vehicles, and spending quality time with family, friends, and clients. He has been married to his wife, Cindy, for almost 40 years. They have three children: Zach, Josh, and Zoey, as well as a crazy border collie named Sweep. After over 25 years assisting families transition into retirement Bill transitioned himself into retirement at the end of 2022.

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, Roth, and HSA contributions to take advantage of tax benefits  How donor-advised funds can amplify charitable giving while reducing taxes Using deferred compensation and capital gains strategies for long-term efficiency Why proactive retirement planning makes the transition smoother and more intentional And more! Resources: Schedule a meeting with the team Connect with Josh Leonard:  [email protected] LinkedIn: Josh Leonard Leonard Advisory Group 412-998-PLAN YouTube: Leonard Advisory Group Facebook: Leonard Advisory Group

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 how to strategize around it The $6,000 senior deduction and how to layer it with other tactics like Roth conversions SALT cap increases and strategies for households earning $500–600K to reduce taxable income The time-sensitive nature of these changes and how intentional planning can help offset future burdens And more! Resources: How Recent Retirement Laws May Affect Your Future (Ep. 95) Schedule a meeting with the team Connect with Josh Leonard:  [email protected] LinkedIn: Josh Leonard Leonard Advisory Group 412-998-PLAN YouTube: Leonard Advisory Group Facebook: Leonard Advisory Group

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 home. Tom discusses: The impact of Variety’s My Bike®, My Voice®, and My Stroller® programs on kids with disabilities and their families How a bike becomes more than just equipment, it becomes a bridge to friendship, inclusion, and physical health Why the My Voice iPad program is giving nonverbal children a way to say “I love you” to their parents Stories from families who experience daily wins thanks to adaptive tools, from grocery trips to school events How retirees and local communities can get involved to give back through volunteering, donations, and mentorship And more! Resources: Schedule a meeting with the team Help create life-changing moments for local kids! Donate to Variety today. Connect with Josh Leonard:  [email protected] LinkedIn: Josh Leonard Leonard Advisory Group 412-998-PLAN YouTube: Leonard Advisory Group Facebook: Leonard Advisory Group Connect with Tom Baker: [email protected]  LinkedIn: Tom Baker  Variety Children’s Charity Pittsburgh About Our Guest:  Tom proudly serves as the Chief Executive Officer of Variety- The Children’s Charity of Pittsburgh. With a mission to empower children with disabilities to live life to the fullest, Variety provides life-changing adaptive mobility and communication equipment. Variety focuses on three core programs: My Bike®, My Stroller®, and My Voice® throughout 59 counties in PA. Previously, he was Executive Director of North Hills Community Outreach. For 12 years, Tom served as the Chief Community Affairs Officer/Vice President of Programs for Big Brothers Big Sisters of Greater Pittsburgh and as President of the BBBS Pennsylvania State Association. He has volunteered as a Big Brother to his little brothers Preston (since 2002), Eric (since 2010), E.J. (since 2015), Eddie (since 2018), and Brian (since 2024) and as a Tutor at Anchorpoint with Ethan (since 2021). He is the Founder/Chief Program Officer of Get Involved!, Inc., and since 2008 has spoken with over 500,000 students, young professionals, and lifelong learners at over 1.000 colleges, corporations, and civic groups across the country. Tom served as President of the Pittsburgh East Rotary Club (2010-12)and President of the Hampton Rotary Club (2023-25). He is President of the Job Corps Community Relations Council, Chair-Elect of the Pittsburgh North Regional Chamber, Past President of NSA Pittsburgh, and Past President of the PUMP Board. Tom received the 2023 Pittsburgh Business Times C-Suite Award, the 2025 Heart of Hampton Award, the 2022 Ross Township Citizen of the Year Award, the 2022 North Hills School District Community Service Award, and was named to the City & State PA 2022 Nonprofit Power 100 List. In 2009, he received the Distinguished Civic Leadership Award from Millersville, and in 2014, he was honored with the MU Young Alumni Achievement Award. Junior Achievement recognized Tom with the 2018 Mayor Caliguiri Good Samaritan Award, and the PNRC honored him with the 2018 Young Professional Award. The Monroeville Area Chamber selected him as the 2011 Young Business Leader of the Year, and Pittsburgh Magazine named him a “40 Under 40” honoree in 2014 and Three Rivers Champion winner in 2017. In Community Magazine, Tom was named 2014 Volunteer of the Year for Ross Township, and he received the 2015 Indiana University of PA Young Alumni Achievement Award. In 2017, he received the Dick Spahr Compassion in Action Award from NHCO. Tom was a 2010 Jefferson Award for Public Service honoree, received the 2014 Distinguished Alumni Leadership Award from Coro, and was a 2013 Pittsburgh Business Times Fast Track honoree.

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 Structuring investments to match retirement goals, manage risk, and address potential tax issues from withdrawals Tax planning strategies, including the benefits of tax diversification, Roth conversions, and minimizing tax burdens for future generations Health care planning, from managing costs pre- and post-Medicare to long-term care considerations and annual prescription reviews The importance of estate planning, updating wills, powers of attorney, and using vehicles like 529 plans for generational wealth and education funding And more! Resources: Schedule a meeting with the team Connect with Josh Leonard:  [email protected] LinkedIn: Josh Leonard Leonard Advisory Group 412-998-PLAN YouTube: Leonard Advisory Group Facebook: Leonard Advisory Group

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 contribution rules How automatic 401(k) enrollment and escalation can benefit retirement savings The “Good Saver” tax issue and why early tax planning is essential Medicare IRMAA surcharges and how to minimize them with intentional withdrawals Why regularly reviewing and adjusting your financial plan matters more than ever And more! Resources: Schedule a meeting with the team Connect with Josh Leonard:  [email protected] LinkedIn: Josh Leonard Leonard Advisory Group 412-998-PLAN YouTube: Leonard Advisory Group Facebook: Leonard Advisory Group

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 Valley Camp. Key Discussion Points: The unique mission of Pine Valley Camp in serving underprivileged children and providing a nurturing environment for growth and learning The emotional and spiritual rewards of volunteering, particularly for retirees seeking meaningful engagement The challenges and opportunities in mentoring youth, instilling core values, and breaking cycles of adversity How retirees can use their skills and experiences to contribute to community-driven programs, such as Retired Tuesdays at Pine Valley Camp The long-term vision for Pine Valley Camp, focusing on expanding its reach and sustaining its impact through strategic planning and donor support And more! Resources: Schedule a meeting with the team Connect with Josh Leonard:  [email protected] LinkedIn: Josh Leonard Leonard Advisory Group 412-998-PLAN YouTube: Leonard Advisory Group Facebook: Leonard Advisory Group Connect with Matthew Reichart: LinkedIn: Matthew Reichart Website: Pine Valley Camp About Matt Reichart:  Mr. Matt and his wife Miss Susan began this ministry at Pine Valley 30 years ago with a desire to create a loving family atmosphere, in a place set apart, where kids could encounter the life-changing gospel message. Matt and Susan have been married 43 years, have 5 adult married children, and 31 grandchildren to date. Mr. Matt is incredibly passionate about the gospel, relationships, and play! He often says kids spell love P.L.A.Y. He loves adventure, so if you stop by camp, you can still find him making time to throw campers in the pool or give jeep rides. Miss Susan is compassionate and is known as the “camp mom”. Because of her desire to create an atmosphere of warmth and kindness, she has a ministry of availability. You will often find her poolside or fireside or about anywhere that someone is in need of a chat. Connect with Julie Saenz: LinkedIn: Julie Saenz Website: Pine Valley Camp

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 planning should account for market downturns before they happen The benefits of tax strategies like Roth conversions during lower market years How to prepare mentally and emotionally for the shift from saving to spending Why retirement should be built around purpose, not just portfolios And more! Resources: Schedule a meeting with the team Check out our latest Visual Insights Newsletter, “Ready for the Future?” with 5 Key Retirement Questions Connect with Josh Leonard:  [email protected] LinkedIn: Josh Leonard Leonard Advisory Group 412-998-PLAN YouTube: Leonard Advisory Group Facebook: Leonard Advisory Group

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 new vs. used vehicles Leasing versus purchasing options, highlighting factors like mileage, monthly payments, and long-term costs Financing strategies, including interest rate comparisons, pre-approvals, and the tax implications for retirees The importance of budgeting for car expenses in retirement Personal stories and anecdotes around car buying experiences And more! Resources: Schedule a meeting with the team Connect with Josh Leonard:  [email protected] LinkedIn: Josh Leonard Leonard Advisory Group 412-998-PLAN YouTube: Leonard Advisory Group Facebook: Leonard Advisory Group

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 cash and retirement buckets for stability Evaluating risks and rebalancing your portfolio And more! Resources: Schedule a meeting with the team Connect with Josh Leonard:  [email protected] LinkedIn: Josh Leonard Leonard Advisory Group 412-998-PLAN YouTube: Leonard Advisory Group Facebook: Leonard Advisory Group

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 adjustments Conducting a tax review to avoid unexpected surprises Strategies for more tax-efficient charitable giving  And more! Resources: Schedule a meeting with the team Connect with Josh Leonard:  [email protected] LinkedIn: Josh Leonard Leonard Advisory Group 412-998-PLAN YouTube: Leonard Advisory Group Facebook: Leonard Advisory Group

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 The importance of incremental tax strategies Options for those in the required distribution stage Future tax landscape insights And more! Resources: Schedule a meeting with the team Join one of our upcoming tax and Social Security classes with AFEA! Connect with Josh Leonard:  [email protected] LinkedIn: Josh Leonard Leonard Advisory Group 412-998-PLAN YouTube: Leonard Advisory Group Facebook: Leonard Advisory Group

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 retirement age and income The removal of WEP (Windfall Elimination Provision) and GPO (Government Pension Offset) under the Social Security Fairness Act of 2025 The potential implications of retroactive payments and strategies to manage tax liabilities from lump sums The importance of evaluating spousal and survivor benefits to enhance financial security for couples Balancing Social Security with other income sources, such as 401(k)s and pensions, to create a comprehensive retirement plan And more! Resources: Schedule a meeting with the team Connect with Josh Leonard:  [email protected] LinkedIn: Josh Leonard Leonard Advisory Group 412-998-PLAN YouTube: Leonard Advisory Group Facebook: Leonard Advisory Group

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 retirees, including the fear of outliving savings and rising healthcare expenses How to strategically plan for major purchases and avoid tax pitfalls in retirement The impact of debt in retirement, including the pros and cons of using 401(k) loans and different debt repayment methods The importance of financial flexibility, including maintaining an emergency fund and planning for unexpected family support needs Common retirement regrets, such as not diversifying investments early enough or failing to plan for long-term financial security And more! Resources: Schedule a meeting with the team Join our free workshops in Pittsburgh through AFEA! Sign up here Subscribe to our monthly newsletter Connect with Josh Leonard:  [email protected] LinkedIn: Josh Leonard Leonard Advisory Group 412-998-PLAN YouTube: Leonard Advisory Group Facebook: Leonard Advisory Group Connect with Pete Belcastro:  LinkedIn: Pete Belcastro, CFP® [email protected]

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 savings with practical financial planning Strategic approaches to maximize Social Security benefits for long-term security The importance of maintaining purpose and emotional fulfillment after retirement Tips for managing healthcare costs and understanding Medicare options Lifestyle considerations like downsizing or relocating to meet personal and financial goals And more! Resources: Schedule a meeting with the team Connect with Josh Leonard:  [email protected] LinkedIn: Josh Leonard Leonard Advisory Group 412-998-PLAN YouTube: Leonard Advisory Group Facebook: Leonard Advisory Group Connect with Pete Belcastro:  LinkedIn: Pete Belcastro, CFP® [email protected]

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, and company sizes to minimize risks The importance of tax diversification through tools like Roth IRAs and taxable accounts for greater financial flexibility How annuities, life insurance, and other financial tools can secure income and simplify legacy planning Strategies to avoid over-concentration in employer-linked investments and protect both your career and portfolio And more! Resources: Schedule a meeting with the team Connect with Josh Leonard:  [email protected] LinkedIn: Josh Leonard Leonard Advisory Group 412-998-PLAN YouTube: Leonard Advisory Group Facebook: Leonard Advisory Group Connect with Pete Belcastro:  LinkedIn: Pete Belcastro, CFP® [email protected]

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 your financial decisions The benefits of tax-advantaged accounts like Roth IRAs Tips for balancing your tax strategy in retirement  Avoiding common tax pitfalls and optimizing for future changes And more! Resources: Schedule a meeting with the team Download our “7 Big Retirement Mistakes Checklist” to help avoid costly retirement mistakes! Connect with Josh Leonard:  [email protected] LinkedIn: Josh Leonard Leonard Advisory Group 412-998-PLAN YouTube: Leonard Advisory Group Facebook: Leonard Advisory Group

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. Josh discusses:  Income planning essentials and pension options Navigating social security concerns and strategies Investment planning for a long, confident retirement Crafting an efficient legacy plan Health planning and managing long-term care costs Tax planning and the benefits of Roth conversions And more Resources: Schedule a meeting with the team Connect with Josh Leonard:  [email protected] LinkedIn: Josh Leonard Leonard Advisory Group 412-998-PLAN YouTube: Leonard Advisory Group Facebook: Leonard Advisory Group

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 aspirations to make retirement a rewarding experience. Josh discusses: How achieving his goal of completing the Leadville MTB 100 taught him the value of preparation and persistence The importance of using the SMART framework (Specific, Measurable, Achievable, Relevant, Time-Bound) when setting personal and financial goals Examples of how retirees can create income plans, like targeting $6,000 monthly from various sources, to ensure financial stability Strategies for maintaining healthy habits, such as balancing exercise, diet, and reducing phone time with family The psychological and emotional benefits of setting goals, including enhanced focus, time management, and overall happiness in retirement And more! Resources: Schedule a meeting with the team Overcoming Obstacles With Grit, Endurance & Family Support (Ep. 66) Connect with Josh Leonard:  [email protected] LinkedIn: Josh Leonard Leonard Advisory Group 412-998-PLAN YouTube: Leonard Advisory Group Facebook: Leonard Advisory Group

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. They Discuss: The emotional and personal rewards of giving during retirement, including the value of sharing time and handmade gifts Creative and budget-conscious gift ideas, such as shared experiences and handmade items, to add meaning without overspending Charitable strategies like Qualified Charitable Distributions (QCDs) and donor-advised funds to maximize the impact of financial giving The importance of holiday traditions and how simple, shared activities can create lasting memories Year-end financial planning tips, including Roth conversions and tax-efficient And more! Resources: Schedule a meeting with the team December to Remember Car Commercial – SNL Christopher’s Kitchen Download our “7 Big Retirement Mistakes Checklist” to help avoid costly retirement mistakes! Connect with Josh Leonard:  [email protected] LinkedIn: Josh Leonard Leonard Advisory Group 412-998-PLAN YouTube: Leonard Advisory Group Facebook: Leonard Advisory Group Connect with Pete Belcastro:  LinkedIn: Pete Belcastro, CFP® [email protected]

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 why we haven’t hit one yet despite all the signs (07:29) The role of consumer spending in sustaining market confidence (09:13) How inflation and interest rates have shaped current market conditions (12:42) The impact of credit ratings and monetary policies on global economies (21:16) Behavioral responses in market bubbles – understanding FOMO and the fallout And more Don’t miss out on understanding these significant market behaviors that could affect your retirement planning.  Resources: Schedule a meeting with the team FOMO in Retirement Planning, Explained (Ep. 56) In Retirement, Put Your Eggs in These Three Baskets by Pete Belcastro Connect with Josh Leonard:  [email protected] LinkedIn: Josh Leonard Leonard Advisory Group 412-998-PLAN YouTube: Leonard Advisory Group Facebook: Leonard Advisory Group Connect with Pete Belcastro:  LinkedIn: Pete Belcastro, CFP® [email protected]

Retirement planning can feel overwhelming, but the right strategies can make it smooth and intentional. How do you structure finances to ensure your money lasts while enjoying the lifestyle you want?  This episode compiles the best retirement advice moments from Josh Leonard and his team, covering vital tips to plan your golden years with confidence.  From managing taxes to healthcare planning, they explore practical solutions for long-term stability. Key Highlights: How to prepare for longer retirements by factoring in family history and careful planning The “three-bucket system” for managing cash, steady income, and long-term growth Proactive ways to minimize healthcare expenses through HSAs and yearly drug plan reviews Tax-saving approaches, such as Roth IRA conversions and efficient withdrawal strategies Creative retirement paths, including passion projects, part-time work, and minimalist lifestyles And more! Resources: Schedule a meeting with the team Download our “7 Big Retirement Mistakes Checklist” to help avoid costly retirement mistakes! Episode 59: Longevity in Retirement: Planning for the Long Haul Episode 61: Healthcare Costs in Retirement: Strategies to Manage Your Expenses Episode 65: Planning for an Early and Intentional Retirement Episode 69: Capital Loss Harvesting vs. Capital Gain Harvesting: What’s Right for Your Retirement? Episode 77: 5 Key Tax Opportunities to Capture Before Year-End! Connect with Josh Leonard:  [email protected] LinkedIn: Josh Leonard Leonard Advisory Group 412-998-PLAN YouTube: Leonard Advisory Group Facebook: Leonard Advisory Group

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 current financial position and plan accordingly Differentiating debts: Understanding car loans versus mortgages and their impact on your credit Strategies for debt repayment: Prioritizing high-interest debts like credit cards Asset knowledge: Understanding different investment types—stocks, bonds, life insurance, and annuities—to make informed decisions And more! Resources: Schedule a meeting with the team Download our “7 Big Retirement Mistakes Checklist” to help avoid costly retirement mistakes! Connect with Josh Leonard:  [email protected] LinkedIn: Josh Leonard Leonard Advisory Group 412-998-PLAN YouTube: Leonard Advisory Group Facebook: Leonard Advisory Group Connect with Pete Belcastro:  LinkedIn: Pete Belcastro, CFP® [email protected]

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 planning And more! Resources: Schedule a meeting with the team Download our “7 Big Retirement Mistakes Checklist” to help avoid costly retirement mistakes! Connect with Josh Leonard:  [email protected] LinkedIn: Josh Leonard Leonard Advisory Group 412-998-PLAN YouTube: Leonard Advisory Group Facebook: Leonard Advisory Group

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 how to set it up  Steps to take if your identity has been stolen  Best practices for password and device security And more! Resources: Schedule a meeting with the team Download our “7 Big Retirement Mistakes Checklist” to help avoid costly retirement mistakes! Think you’ve been targeted by a scam? Report it to the FTC and get resources to protect yourself Set up your IRS PIN to protect your tax information from fraud Connect with Josh Leonard:  [email protected] LinkedIn: Josh Leonard Leonard Advisory Group 412-998-PLAN YouTube: Leonard Advisory Group Facebook: Leonard Advisory Group About our Guest: Angela Ferrante is a 1987 graduate of Allegheny College with a degree in Economics and Finance. She started with Equitable Life as an insurance representative 2 weeks after graduation selling life and disability insurance to the medical community. By 2005 she was supervising 165 representatives in 4 states and running the brokerage side of the office which included the opening of accounts, research, trade placement, cashiering of upwards of $2 million per month, as well as her own client base. Angela became an Accredited Investment Fiduciary in 2015. Angela and Mark live in Somerset County where she enjoys skiing, hiking, biking and gardening.

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 Finding purpose and connection through hobbies and community involvement And more! Resources: Schedule a meeting with the team Download our “7 Big Retirement Mistakes Checklist” to help avoid costly retirement mistakes! Connect with Josh Leonard:  [email protected] LinkedIn: Josh Leonard Leonard Advisory Group 412-998-PLAN YouTube: Leonard Advisory Group Facebook: Leonard Advisory Group Connect with Pete Belcastro:  LinkedIn: Pete Belcastro, CFP® [email protected]

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 retirement. Learn how tailored planning can lead to a worry-free retirement, allowing you to focus on living your life to the fullest. They discuss:  How comprehensive tax planning can significantly reduce unnecessary expenses The benefits of using a structured, three-bucket strategy for financial security Real-life success stories demonstrating financial empowerment through planning Strategies for maximizing income in retirement while minimizing potential financial stressors And more! Resources: Schedule a meeting with the team Download our “7 Big Retirement Mistakes Checklist” to help avoid costly retirement mistakes! Connect with Josh Leonard:  [email protected] LinkedIn: Josh Leonard Leonard Advisory Group 412-998-PLAN YouTube: Leonard Advisory Group Facebook: Leonard Advisory Group Connect with Pete Belcastro:  LinkedIn: Pete Belcastro, CFP® [email protected]

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 strategy, and efficient ways to manage generosity through Qualified Charitable Distributions (QCDs), donor-advised funds, and stock gifting.  They discuss:  How Qualified Charitable Distributions (QCDs) can benefit your taxes and your favorite charities How donor-advised funds offer a strategic approach to managing philanthropic efforts and tax planning The benefits of gifting appreciated stock to family or charities to reduce potential capital gains tax Inspiring stories about the impact of efficient giving on individual lives and overall financial health And more! Resources: Schedule a meeting with the team Making an Impact with Donor-Advised Funds ft. Adam Nash (Ep. 47) Connect with Josh Leonard:  [email protected] LinkedIn: Josh Leonard Leonard Advisory Group 412-998-PLAN YouTube: Leonard Advisory Group Facebook: Leonard Advisory Group Connect with Pete Belcastro:  LinkedIn: Pete Belcastro, CFP® [email protected]

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 for enrollment and why they matter. The importance of reviewing and possibly switching your drug plan to save costs. The differences between traditional Medicare and Medicare Advantage, and why it matters for your health coverage. And More! Join us as we dive into these topics and more on ensuring your healthcare needs are met without unexpected costs in retirement. Don’t miss out on these valuable insights that will help you make informed decisions for your health and wallet. Subscribe and get ready to retire with intent! Resources: Schedule a meeting with the team Connect with Josh Leonard:  [email protected] LinkedIn: Josh Leonard Leonard Advisory Group 412-998-PLAN YouTube: Leonard Advisory Group Facebook: Leonard Advisory Group

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 and Pete discuss:  Understanding the shift from inflation to broader economic concerns  Strategies to manage potential market volatility and protect your investments The impact of interest rate changes on savings and investments The importance of staying informed and focused on long-term trends in financial planning And more! Resources: Schedule a meeting with the team Connect with Josh Leonard:  [email protected] LinkedIn: Josh Leonard Leonard Advisory Group 412-998-PLAN YouTube: Leonard Advisory Group Facebook: Leonard Advisory Group Connect with Pete Belcastro:  LinkedIn: Pete Belcastro, CFP® [email protected]  

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 election outcomes on the stock market and your retirement How to manage fears related to market unpredictability by maintaining a diversified portfolio Practical advice on keeping an appropriate emergency fund and navigating the three-bucket strategy Insights on long-term financial planning despite the political climate And more! Resources: Schedule a meeting with the team Connect with Josh Leonard:  [email protected] LinkedIn: Josh Leonard Leonard Advisory Group 412-998-PLAN YouTube: Leonard Advisory Group Facebook: Leonard Advisory Group

Are you maximizing the potential of capital gains and losses in your retirement planning? This week, Josh Leonard and Pete Belcastro dive into the often-overlooked strategies of capital gain and loss harvesting. You’ll learn the essential differences between capital loss and capital gain harvesting, why timing and tax brackets play a crucial role in your financial planning, and how these strategies can help minimize your tax liability, particularly in retirement.  Join us for an informative discussion that could significantly influence how you manage your investments for a more secure financial future. Josh and Pete discuss:  Exploring Capital Loss vs. Capital Gain Harvesting: Understanding the fundamental principles and their implications for your tax strategy Timing is Everything: Why the fourth quarter is critical for reviewing and adjusting your tax planning strategies Tax Brackets: How these affect your decision-making on selling assets and realizing gains or losses Retirement Focus: Tailoring these strategies to optimize tax savings and maintain financial health in your golden years And more! Resources: Schedule a meeting with the team Connect with Josh Leonard:  [email protected] LinkedIn: Josh Leonard Leonard Advisory Group 412-998-PLAN YouTube: Leonard Advisory Group Facebook: Leonard Advisory Group Connect with Pete Belcastro:  LinkedIn: Pete Belcastro, CFP® [email protected]

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 Cash, Income, and Growth Buckets (09:18) Utilizing financial tools like HSAs and annuities to maximize benefits (16:57) Adapting to market volatility without making hasty decisions (21:18) Making the most of your newfound time, hobbies, family time, and volunteering And more Resources: Schedule a meeting with the team 6 Ways to Travel on a Budget in Retirement (Ep. 67) Connect with Josh Leonard:  [email protected] LinkedIn: Josh Leonard Leonard Advisory Group 412-998-PLAN YouTube: Leonard Advisory Group Facebook: Leonard Advisory Group

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 expenses, and taking advantage of discounts And more   Resources: Schedule a meeting with the team National Parks & Federal Recreational Lands Senior Pass Million Mile Secrets The Points Guy Expedia Kayak Southwest Airlines Low Fare Calendar Connect with Josh Leonard:  [email protected] LinkedIn: Josh Leonard Leonard Advisory Group 412-998-PLAN YouTube: Leonard Advisory Group Facebook: Leonard Advisory Group

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 a reliable support system can make all the difference. From unexpected flat tires to quick solutions, learn how this endurance race teaches vital lessons for retirement planning and navigating life’s unpredictability.  Josh and Yana talk about: How Josh overcame unexpected challenges during the race with the help of his wife and community The quick, practical solutions that helped Josh complete the race – a lesson in planning for the unpredictable The crucial role of support systems in achieving big goals, both in sports and financial planning How disciplined training and strategic planning in sports can translate to successful retirement strategies And more   Resources: Schedule a meeting with the team Variety My Bike Donation Variety My Bike Program Overview Leadville Race Info Leadville Race Recap Leadville Trail 100 Legacy Foundation Connect with Josh Leonard:  [email protected] LinkedIn: Josh Leonard Leonard Advisory Group 412-998-PLAN YouTube: Leonard Advisory Group Facebook: Leonard Advisory Group Connect with Yana Leonard: LinkedIn: Yana Leonard Leonard Advisory Group

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 on extreme savings and lifestyle choices Challenges and strategies for those aiming to retire in their 30s or 40s versus traditional retirement age Tips for managing finances, including healthcare and penalty-free withdrawals, for those considering early retirement And more Resources: Schedule a meeting with the team Your Money Your Life by Vicki Robin and Joe Dominguez Connect with Josh Leonard:  [email protected] LinkedIn: Josh Leonard Leonard Advisory Group 412-998-PLAN YouTube: Leonard Advisory Group Facebook: Leonard Advisory Group Connect with Pete Belcastro:  LinkedIn: Pete Belcastro, CFP® [email protected]

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 and Pete discuss:  Why regularly updating your will and legal documents is important The role of Power of Attorney in managing assets during incapacitation How to use trusts to protect assets and control distributions How you can minimize the impact of estate taxes And more Resources: Schedule a meeting with the team Navigating RMD Changes for Your Retirement Plan (Ep. 62)  Connect with Josh Leonard:  [email protected] LinkedIn: Josh Leonard Leonard Advisory Group 412-998-PLAN YouTube: Leonard Advisory Group Facebook: Leonard Advisory Group Connect with Pete Belcastro:  LinkedIn: Pete Belcastro, CFP® [email protected]

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 personal priorities and hear insightful anecdotes from Josh’s years of experience. Josh and Pete discuss:  The top factors that determine the best states to retire in How different states compare The impact of state and local taxes on retirement planning The importance of balancing the cost of living with lifestyle and proximity to family And more Resources: Schedule a meeting with the team Connect with Josh Leonard:  [email protected] LinkedIn: Josh Leonard Leonard Advisory Group 412-998-PLAN YouTube: Leonard Advisory Group Facebook: Leonard Advisory Group Connect with Pete Belcastro:  LinkedIn: Pete Belcastro, CFP® [email protected]

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 surrounding inherited IRAs, making this a must-listen for anyone approaching or navigating retirement. Josh and Pete discuss:  Understanding Required Minimum Distributions (RMDs) and their recent rule changes The implications of inheriting an IRA and the different types of beneficiaries How the Secure Act has changed the way RMDs are calculated and distributed How to navigate these complex rules and avoid potential penalties And more Resources: Schedule a meeting with the team Understanding RMDs: 6 Strategies to Reduce Your Tax Burden Connect with Josh Leonard:  [email protected] LinkedIn: Josh Leonard Leonard Advisory Group 412-998-PLAN YouTube: Leonard Advisory Group Facebook: Leonard Advisory Group Connect with Pete Belcastro:  LinkedIn: Pete Belcastro, CFP® [email protected]

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 shopping around for prescription drug plans annually The advantages of contributing to and using a Health Savings Account (HSA) And more   Resources: Schedule a meeting with the team Medicare Genworth Long-Term Care Cost Survey GoodRx   Connect with Josh Leonard:  [email protected] LinkedIn: Josh Leonard Leonard Advisory Group 412-998-PLAN YouTube: Leonard Advisory Group Facebook: Leonard Advisory Group   Connect with Pete Belcastro:  LinkedIn: Pete Belcastro, CFP® [email protected]

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 offer nuanced views and actionable insights on when to break these rules to suit individual financial needs and goals better. Join their discussion as they talk about how to achieve a more nuanced and personalized approach to financial planning, ensuring a more robust and flexible retirement strategy for listeners. Josh and Pete discuss: The true impact of paying off your mortgage before retirement The benefits and drawbacks of using credit cards in retirement How to maintain a realistic budget without sacrificing quality of life The importance of re-evaluating the “100 minus your age” rule in investment strategies And more   Resources: Schedule a meeting with the team Pete’s Credit Score Video   Connect with Josh Leonard:  [email protected] LinkedIn: Josh Leonard Leonard Advisory Group 412-998-PLAN YouTube: Leonard Advisory Group Facebook: Leonard Advisory Group   Connect with Pete Belcastro:  LinkedIn: Pete Belcastro, CFP® [email protected]