Dec 24, 2025
In this Christmas episode, Jesse steps back from year-end checklists and market noise to tell a more personal story—one shaped by the “ghosts” of his financial past, present, and future. He begins with the early experiences that formed his relationship with money: a summer concession stand that taught him pricing,...
Dec 10, 2025
On Jesse’s 11th “Ask Me Anything” episode, he unpacks four questions that sit at the center of real-life financial decision-making. He starts with a grounded look at the 15-year vs. 30-year mortgage debate, cutting through rules of thumb to show how interest rates, liquidity, cash-flow, and even your...
Dec 3, 2025
Jesse sits down with Andy Hill—personal finance educator, podcast host, and creator of Marriage, Kids, and Money—for a candid conversation about building wealth while building a life you actually enjoy. Andy shares how a mix of financial discipline, intentional goal-setting, and family-centered values helped him and...
Nov 26, 2025
Today, Jesse is joined by Dr. Phil Pearlman—psychologist, behavioral finance veteran, and founder of the Pearl Institute—for a conversation about how long-term health and long-term wealth are two sides of the same coin. Together, they explore why the holiday season, while full of joy and connection, is also the...
Nov 12, 2025
Jesse returns for the 10th “Ask Me Anything” episode to tackle three listener questions that cut to the core of modern wealth planning. He opens with a deep dive into direct indexing, separating substance from sales pitch. While advocates tout it as the next evolution of indexing—combining personalization...