Sep 23, 2026
Looking for a financial planner? → PlanWithJesse.com
Jesse answers a new round of early-retirement questions, beginning with how investors can build a portfolio designed to last through a potentially long retirement. He explains why focusing narrowly on dividends, interest, or other forms of “income generation”...
Sep 9, 2026
Sure, you own index funds. But 99% of portfolios have a “shade of gray” that’s more active than we realize. This episode dives into the “shades of gray” in passive investing and how they affect our portfolios and benchmarks.
Looking for a financial planner? → PlanWithJesse.com
Jesse explores an important...
Sep 2, 2026
Jesse shares an exciting new career update. And to celebrate 150 episodes, we're doing a unique AMA episode.
Looking for a financial planner? → PlanWithJesse.com
First, Jesse shares an exciting new career update. He has joined a new financial planning firm - as an advisor and an owner. The new firm, Rialto, is...
Aug 26, 2026
An "Ask Me Anything" episode including questions like:
- Effective tax rates or marginal tax rates…which one matters?
- I’m at my retirement number, but this stock market is too crazy…should I adjust my portfolio?
- What about flexible spending rules in retirement? Which are good, which aren’t, and how to use them...
Aug 12, 2026
We all know the importance of having a good financial plan in place. But…are we all talking about the same thing? What *is* a financial plan, and how do we know if ours is good or not?
Looking for a financial planner? → PlanWithJesse.com
Jesse explores what financial planning actually is, why it extends far beyond...