Podcast Feed
Military Money Lessons That Civilians Can’t Afford to Miss | Spencer Reese - E117
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
Manage *Yourself* More Than Your Portfolio | Hanna Horvath - E116
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
Where Investors Go Wrong: Tax Traps, Math Mistakes, and Behavioral Biases
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
Where Investors Go Wrong: Tax Traps, Math Mistakes, and Behavioral Biases - E115
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
The Risks and Rewards of Quitting Your Career | Kelan Kline - E114
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
How to Be Smart About Inheritance Planning | AMA #8 - E113
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
Reset Your Portfolio Expectations, Before It's Too Late | Peter Lazaroff - E112
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
When Smart Financial Planning Backfires - ChooseFI Companion Episode - E111
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
Buffett’s Blueprint - 8 Examples of Warren’s Timeless Wisdom - E110
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
Scrimping, Splurging, and Other Crazy Spending Stories - E109
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
Go Roth Now Before It’s Too Late? And Other Listener Questions | AMA #7 - E108
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
19 Questions to Uncover Good, Bad, and Ugly Financial Advisors | Don McDonald - E107
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
Retirees’ Mistakes and Wake-Up Calls: Expectations vs. Reality - E106
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
It’s Not Too Late: Smart Money Moves After 50 | Bill Yount - E105
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
Tariffs, Turbulence, and the Harsh Truths We Must Now Face - Bonus Episode
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
"Tax-Free Retirement" - Smart Strategy or Overhyped Gimmick? And Other Listener Questions | AMA #6 …
Jesse answers listener questions on financial planning, investment management, and retirement. He discusses the challenges of rising homeowner’s insu…
The Best Interest
04/09/2025
Life Expectancy, Caregiving Costs, & Retirement Planning | Christine Benz - E103
Jesse Cramer speaks with Christine Benz, Director of Personal Finance at Morningstar, about insights from her book How to Retire. Before their discus…
The Best Interest
03/26/2025
Life-Expectancy, Caregiving Costs, & Retirement Planning | Christine Benz - E103
Jesse Cramer speaks with Christine Benz, Director of Personal Finance at Morningstar, about insights from her book How to Retire. Before their discus…
The Best Interest
03/26/2025
The Truth About the U.S. National Debt (And How It Impacts You Personally) - E102
Today we take a look at the U.S. national debt, distinguishing it from household debt and analyzing its impact on individuals and investors. Jesse tr…
The Best Interest
03/12/2025
Do Long-Term Investors *Need* to Invest in Real Estate? | Chad “Coach” Carson - E101
Jesse is joined by Chad Carson, who discusses residential real estate investing as a stable alternative to stocks and bonds. While real estate offers…
The Best Interest
02/26/2025