What are the six components of "behavioral loss tolerance," and where do you stand as an investor?
I suppose a lot of this comes down to how much "wonderful" you want, and where you’re willing to sacrifice for your "wonderful."
If I have limited space in my financial plan, am I better off paying 0% capital gains or doing low-tax Roth conversions?
Do required minimum distributions (RMDs) have a destructive synergy with the sequence of returns risk? Can this combo "sink your boat?"
This is why we own both stocks and bonds. They serve simple, important, and drastically different purposes.
"I'd gladly pay you $150 or $200 per hour for a few hours of your time. I'm curious why you don't work hourly?"
"I'd gladly pay you $150 or $200 per hour for a few hours of your time. I'm curious why you don't work hourly?"
What are the 10 most important aspects of a financially sound retirement, and how do we start preparing for that future today?
A deep (and I mean *DEEP*) dive into optimizing your retirement withdrawal order of operations to make your money last.
Want a successful retirement? Let's use the principal of inversion. We'll identify the common mistakes, and then NOT do those things!
Jesse tackles six thoughtful listener questions spanning a range of personal finance topics. He begins with a question about using Social Security an…
The Best Interest
08/06/2025
Jesse welcomes back Peter Lazaroff to discuss the psychology and strategy of investing during uncertain times. They explore how media narratives and …
The Best Interest
07/23/2025
Today’s episode is a special bonus episode, a companion to Jesse’s discussion on episode 555 of ChooseFI! Jesse examines the risks of over-optimizati…
The Best Interest
07/14/2025
Jesse explores the timeless wisdom of Warren Buffett, highlighting both his disciplined investment philosophy and his unwavering emphasis on trust an…
The Best Interest
07/02/2025
Jesse explores the value of financial priorities and the balance between spending and saving with guests Diania Merriam, Justin Peters, Bill Yount, J…
The Best Interest
06/18/2025
Jesse answers a range of listener questions on topics including estate planning, life insurance, financial benefits of marriage, tax strategies for h…
The Best Interest
06/04/2025
Today, Jesse is joined by Don McDonald to offer a critical examination of the financial advising and annuity industries, warning retirees and near-re…
The Best Interest
05/21/2025
Jesse explores insights from the Retirements and Perspectives study, which captures the experiences and expectations of individuals transitioning int…
The Best Interest
05/07/2025
Jesse explores the financial journey of late starters with guest Bill Yount, co-host of Catching Up to FI. In the opening monologue, Jesse shares his…
The Best Interest
04/23/2025
Today, Jesse critiques emotional, reactive investing during volatile market conditions—especially in response to tariffs and recession fears—while pr…
The Best Interest
04/14/2025
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