Summer often brings vacations, family activities, and unexpected expenses, making it easy to lose sight of financial goals.

Taking a few proactive steps before spending ramps up can help you avoid unnecessary taxes, overlooked opportunities, and preventable financial headaches.

In this episode, Josh Leonard and Pete Belcastro explore five financial questions to ask before summer gets into full swing. They explain why reviewing tax withholding, checking beneficiary designations, evaluating insurance coverage, maximizing tax-advantaged accounts, and planning seasonal expenses can help retirees and those approaching retirement make more informed financial decisions.

They also clarify the difference between tax preparation and tax planning while sharing practical ways to make retirement spending more intentional throughout the year.

Key takeaways:

• Reviewing tax withholding before large withdrawals may help reduce unexpected tax surprises later
• Checking beneficiary designations after life changes helps retirement assets reflect current wishes
• Evaluating insurance coverage before traveling may help avoid duplicate policies and extra costs
• Using HSAs, Roth accounts, and employer matches can improve long-term tax efficiency over time
• Planning summer expenses ahead of time helps reduce financial stress during vacations and family activities
• 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

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