Owning multiple mutual funds doesn’t mean you have a diversified retirement plan, and for many retirees, it can create surprises they never saw coming.

In this episode, Josh Leonard sits down with Leonard Advisory Group CFP® Peter Belcastro to unpack the five common problems they see with mutual funds, especially for people nearing or living in retirement. While mutual funds can be a great starting point for investing, Josh and Pete explain why they may not always fit a complete retirement strategy.

Josh and Pete discuss:

• Why diversification inside mutual funds can sometimes be an illusion
• How overlapping investments may increase risk without people realizing it
• The hidden tax consequences of mutual funds, including “phantom gains.”
• Why investment tools should support a retirement plan, not replace one
• And more!

Resources:

• Schedule a meeting with the team

Connect with Josh Leonard:

• jleonard@leonardadvisorygroup.com
• LinkedIn: Josh Leonard
• Leonard Advisory Group
• 412-998-PLAN
• YouTube: Leonard Advisory Group
• Facebook: Leonard Advisory Group

Connect with Pete Belcastro:

• LinkedIn: Pete Belcastro
• Leonard Advisory Group

About our Guest: Pete Belcastro is a CERTIFIED FINANCIAL PLANNER professional at Leonard Advisory Group. In addition to helping clients build intentional retirement plans, Pete brings deep experience in the mutual fund and investment management space. In this episode, he joins Josh Leonard to break down common misconceptions around diversification, taxes, and investment strategy, helping listeners better understand how their investments fit into a broader retirement plan.

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:

• jleonard@leonardadvisorygroup.com
• 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:

• jleonard@leonardadvisorygroup.com
• 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:

• jleonard@leonardadvisorygroup.com
• 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:

• jleonard@leonardadvisorygroup.com
• 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:

• jleonard@leonardadvisorygroup.com
• 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:

• jleonard@leonardadvisorygroup.com
• 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:

• jleonard@leonardadvisorygroup.com
• LinkedIn: Josh Leonard
• Leonard Advisory Group
• 412-998-PLAN
• YouTube: Leonard Advisory Group
• Facebook: Leonard Advisory Group