Jesse opens the show by sharing a personal anecdote about a former teacher's challenging investment choices, which were burdened with... more

Today, Jesse helps us step out of our financial frame and see the broader context of our lives. Quoting from... more

Back with another AMA, Jesse tackles your questions on employee stock incentives, diversification, how taxes affect investments, and more! Our... more

Jesse explores the intricacies of student loan forgiveness, highlighting the fallacy that loans can simply vanish without consequence. He argues... more

Referring back to his article, Fundamentals Of Retirement: Is the Summit “Good Enough?”, Jesse uses an experience hiking in the Adirondack... more

In today’s opening monologue, Jesse explores the concept of Sequence of Returns Risk, a crucial and often misunderstood threat to... more

In today’s AMA, Jesse delves into various financial dilemmas and strategies to maximize benefits and secure a stable retirement. The... more

Jesse starts by sharing two of his blog posts in today’s monologue.  The first post, “The Answers are Here, But…”,... more

Jesse begins today's episode with two reflections. First, he talks about the rarity and preciousness of gathering all your loved... more

Jesse starts this episode with a confession: money still stresses him out. The four ways that Jesse reduces this stress... more