Podcast Feed
Favorite Moments, Shoutouts, and a Name Change?! …From Our First 100 Episodes - E100
Episode 100 of The Best Interest Podcast! This is a celebratory and reflective milestone featuring guest shout-outs, listener-favorite clips, and a d…
The Best Interest
02/12/2025
Will They Claw Back My Tax Breaks? Should I “Buy, Borrow, and Die?” And More - AMA #5 - E99
Time for another AMA with Jesse! First, Randy asks what it means to be rich, leading to an interesting evaluation of personal values, goals, and circ…
The Best Interest
01/29/2025
What Do You Mean By “little p purpose”?! | Jordan Grumet - E98
Jordan Grumet, AKA Doc G, returns to the podcast to share the difference between “Big P Purpose” and “little p purpose” and why you should pursue the…
The Best Interest
01/15/2025
The Bad “Money Scripts” Someone Else Wrote for You | Brad Klontz - E97
Jesse kicks today’s show off with a monologue on the importance of having the right temperament for investing - it’s not really about intelligence at…
The Best Interest
01/01/2025
But is NOW the Right Time to Invest in the Stock Market?! - E96
Talking solo, Jesse tackles two important, ever-present investing questions in today’s monologue. Should I try to time the market? How do I beat th…
The Best Interest
12/18/2024
Tax Loss Harvesting Myths Debunked: What You Need to Know Now | AMA #4 with Jesse - E95
Jesse is solo, answering your questions! Kate, a government worker with $650,000 in IRAs, is wondering how she can best rebalance her portfolio - and…
The Best Interest
12/04/2024
Silly Hacks, New Rules, & Unpopular Opinions - E94
Jesse’s running the show solo this week, bringing with him some interesting perspectives on tax tricks, whether you should rent or buy, and college e…
The Best Interest
11/20/2024
Instructive and Surprising Questions to Ask Before You Retire | Joe Saul-Sehy - E93
What are the long-term gains of educated investment decisions? The COVID pandemic triggered fear and uncertainty, with many wanting to sell everythin…
The Best Interest
11/06/2024
Why Teachers Need to Be Careful | Dan Otter - E92
Jesse opens the show by sharing a personal anecdote about a former teacher's challenging investment choices, which were burdened with high fees from …
The Best Interest
10/23/2024
What No One Tells You About Early Retirement | Steve Adcock - E91
Today, Jesse helps us step out of our financial frame and see the broader context of our lives. Quoting from David Foster Wallace’s “This is Water” s…
The Best Interest
10/09/2024
No Diversification = Deep Trouble?! | AMA #3 with Jesse - E90
Back with another AMA, Jesse tackles your questions on employee stock incentives, diversification, how taxes affect investments, and more! Our first …
The Best Interest
09/25/2024
Societal Challenges and the “Money World” Don't Always Mix | Katie Gatti Tassin - E89
Jesse explores the intricacies of student loan forgiveness, highlighting the fallacy that loans can simply vanish without consequence. He argues that…
The Best Interest
09/11/2024
Practical Reasons Why "Retirement Success" Can Still Be Painful | Rob Berger - E88
Referring back to his article, Fundamentals Of Retirement: Is the Summit “Good Enough?”, Jesse uses an experience hiking in the Adirondack Mountains …
The Best Interest
08/28/2024
How To Secure an Edge Against “Sequence of Returns” Risk | Tyler of Portfolio Charts - E87
In today’s opening monologue, Jesse explores the concept of Sequence of Returns Risk, a crucial and often misunderstood threat to retirees, by illust…
The Best Interest
08/14/2024
Should I Drain My 401k to Pay Off My Mortgage? | AMA #2 with Jesse - E86
In today’s AMA, Jesse delves into various financial dilemmas and strategies to maximize benefits and secure a stable retirement. The first question c…
The Best Interest
07/31/2024
Red Flag Finance Scams on the Big, Scary Internet | Rachael Camp - E85
Jesse starts by sharing two of his blog posts in today’s monologue. The first post, “The Answers are Here, But…”, expands on William Gibson’s quote,…
The Best Interest
07/17/2024
How New Parents Can Avoid Money Mistakes | Andy Hill - E84
Jesse begins today's episode with two reflections. First, he talks about the rarity and preciousness of gathering all your loved ones in one place. W…
The Best Interest
07/03/2024
Fight, Flight, and Friction: Being Smart in Your Volatile Portfolio | Carl Richards - E83
Jesse starts this episode with a confession: money still stresses him out. The four ways that Jesse reduces this stress are remembering what’s going …
The Best Interest
06/19/2024
“Truth: We Are Very Bad At Anticipating What We Want” | Jonathan Clements - E82
Jesse begins today’s episode with a short monologue on the highs and lows of money. Can money buy happiness? Or are they uncorrelated? Either way, mo…
The Best Interest
06/05/2024
"Is My 100% S&P 500 Portfolio Wrong?" | AMA #1 with Jesse - E81
On today’s episode, we bring you something a little different. Jesse’s collected a series of questions from newsletter subscribers and will answer th…
The Best Interest
05/22/2024