In this episode, Josh Leonard and Yana Leonard, Chief Risk and Operations Officer at Leonard Advisory Group, explore how grandparents are becoming a bigger part of childcare, family finances, and everyday life. They share their own experience relying on grandparents, examine the financial pressure that family support can create, and consider 529 plans, family trips, relocation, and other ways retirees may help.

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.

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.

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.

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.

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.