There are dozens of Social Security "strategies." Should the higher-earning spouse delay Social Security as long as possible?
Not only is the stock market at an all-time high, but valuations are also creeping higher. Should we be *selling* some stocks?
How do healthcare costs change - and how do we plan for that? - during the different stages and phases of your retirement?
Some of us retire at 70. Others at 40. But no matter your retirement age, your retirement will change over time.
401(k) accounts are ubiquitous. It's common to see large 401k balances. But is there such a thing as "too big" a pre-tax bucket?
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.
Today, Jesse is joined by Spencer Reese—Air Force veteran, financial educator, and creator of the Military Money Manual—for a conversation about the …
The Best Interest
10/01/2025
Today, Jesse is joined by Hanna Horvath—Certified Financial Planner, managing editor at Bankrate, and author of the Your Brain on Money newsletter—fo…
The Best Interest
09/17/2025
Today, Jesse goes solo for a candid episode unpacking the most common mistakes and misconceptions he sees in personal finance, from the temptation to…
The Best Interest
09/03/2025
Today, Jesse goes solo for a candid episode unpacking the most common mistakes and misconceptions he sees in personal finance, from the temptation to…
The Best Interest
09/03/2025
Today, Jesse is joined by Kelan Kline, co-founder of The Savvy Couple, who shares his entrepreneurial journey from working as a jail deputy to buildi…
The Best Interest
08/20/2025
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
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