Helping your children and grandchildren can become one of the most meaningful parts of retirement, but how much time, money, and energy can you comfortably give? 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, …
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 …
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 …
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 …
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 …
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 …
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 …
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 …
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 …
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, …