Personal Finance for Long-Term Investors
Episodes
Target Date Funds: More Flawed Than Advertised (E137)
22 Apr 2026
Contributed by Lukas
Looking for a financial planner? → PlanWithJesse.com Jesse delivers a critical re-evaluation of target date funds—one of the most widely used "s...
He Retired Early - Here's What No One Warned Him About (E136)
08 Apr 2026
Contributed by Lukas
In today's replay of episode 62, Jesse is joined by Fritz Gilbert—retirement blogger behind The Retirement Manifesto and former corporate executive ...
Why Trump Accounts Fall Short (AMA, E135)
01 Apr 2026
Contributed by Lukas
On his 15th Ask Me Anything episode, Jesse tackles a fresh set of listener questions with a throughline that centers on how to evaluate financial deci...
Even Financial Advisors Misunderstand Monte Carlo Retirement Analysis
25 Mar 2026
Contributed by Lukas
In this technical deep dive, Jesse pulls back the curtain on one of the most commonly cited tools in retirement planning—Monte Carlo analysis—expl...
Good Investors Stay Seated (Especially When It's Scary) | Rubin Miller - E133
11 Mar 2026
Contributed by Lukas
Jesse is joined by Rubin Miller—former Dimensional Fund Advisors insider, founder and CIO of Paltoma Capital Partners, author of the Fortunes and Fr...
Controversial Retirement Money Topics | AMA #14 - E132
04 Mar 2026
Contributed by Lukas
On his 14th Ask Me Anything episode, Jesse tackles a set of listener questions that expose the messy, real-world edges of financial planning—where t...
"The Devil's Advocate Buys an Annuity…" - E131
25 Feb 2026
Contributed by Lukas
In this expansive and deliberately contrarian episode, Jesse takes on annuities—not with a sales pitch or a blanket dismissal, but by putting them u...
Giving "Defined Duration" to Stocks | Cullen Roche - E130
11 Feb 2026
Contributed by Lukas
Jesse is joined by Cullen Roche—financial writer, macro thinker, and founder of Discipline Funds—for a clear-eyed conversation about how money act...
The Financial Planning Process, Step-By-Step | AMA #13 - E129
04 Feb 2026
Contributed by Lukas
On Jesse's 13th AMA episode, he steps back from tactics and returns to first principles, answering listener questions that cut to the core of what fin...
Some Dumb Financial Moves (That I'm Fine With) - E128
28 Jan 2026
Contributed by Lukas
In this candid solo episode, Jesse walks through a series of financial decisions that look "wrong" on paper but make complete sense when viewed throug...
Longevity & Retirement | Jeremy Keil - E127
14 Jan 2026
Contributed by Lukas
Jesse is joined by Jeremy Keil—Certified Financial Planner, Chartered Financial Analyst, author of Retire Today, and host of the Retirement Revealed...
Is 2026 Your Year to Retire? | AMA #12 - E126
07 Jan 2026
Contributed by Lukas
On Jesse's 12th "Ask Me Anything" episode, he opens the year by tackling the questions that tend to surface when calendars turn and retirement feels c...
Jesse's Ghosts of Financial Past, Present, and Future | E125
24 Dec 2025
Contributed by Lukas
In this Christmas episode, Jesse steps back from year-end checklists and market noise to tell a more personal story—one shaped by the "ghosts" of hi...
Dying With an HSA, Mystery Mortgage Math, & Should DIY Investors Hire a Planner? | AMA #11 - E124
10 Dec 2025
Contributed by Lukas
On Jesse's 11th "Ask Me Anything" episode, he unpacks four questions that sit at the center of real-life financial decision-making. He starts with a g...
Feeling Time Poor? The Journey to Owning Your Time | Andy Hill - E123
03 Dec 2025
Contributed by Lukas
Jesse sits down with Andy Hill—personal finance educator, podcast host, and creator of Marriage, Kids, and Money—for a candid conversation about b...
Health and Wealth - The Power of a "Bigger Yes" | Phil Pearlman - E122
26 Nov 2025
Contributed by Lukas
Today, Jesse is joined by Dr. Phil Pearlman—psychologist, behavioral finance veteran, and founder of the Pearl Institute—for a conversation about ...
Retire Confidently With A Proven Drawdown Framework | AMA #10 - E121
12 Nov 2025
Contributed by Lukas
Jesse returns for the 10th "Ask Me Anything" episode to tackle three listener questions that cut to the core of modern wealth planning. He opens with ...
Marketing Algorithms Are Coming For Your Retirement Dollars | John Dinsmore - E120
05 Nov 2025
Contributed by Lukas
Today, Jesse is joined by Professor John Dinsmore—behavioral finance researcher, marketing scholar, and author of The Marketing of Debt: How They Ge...
Special Needs Children: How to Protect Their Future and Yours - E119
22 Oct 2025
Contributed by Lukas
Jesse goes solo for a deep dive into the vital yet often overlooked world of special needs financial planning. He opens with a personal story about hi...
The Only Free Lunch in Investing (Maybe) | AMA #9 - E118
08 Oct 2025
Contributed by Lukas
Jesse fields six wide-ranging listener questions that dig into the heart of financial planning and investing. He opens with a challenge to the idea th...
Military Money Lessons That Civilians Can't Afford to Miss | Spencer Reese - E117
01 Oct 2025
Contributed by Lukas
Today, Jesse is joined by Spencer Reese—Air Force veteran, financial educator, and creator of the Military Money Manual—for a conversation about t...
Manage *Yourself* More Than Your Portfolio | Hanna Horvath - E116
17 Sep 2025
Contributed by Lukas
Today, Jesse is joined by Hanna Horvath—Certified Financial Planner, managing editor at Bankrate, and author of the Your Brain on Money newsletter—...
Where Investors Go Wrong: Tax Traps, Math Mistakes, and Behavioral Biases - E115
03 Sep 2025
Contributed by Lukas
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 Risks and Rewards of Quitting Your Career | Kelan Kline - E114
20 Aug 2025
Contributed by Lukas
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 buildin...
How to Be Smart About Inheritance Planning | AMA #8 - E113
06 Aug 2025
Contributed by Lukas
Jesse tackles six thoughtful listener questions spanning a range of personal finance topics. He begins with a question about using Social Security and...
Reset Your Portfolio Expectations, Before It's Too Late | Peter Lazaroff - E112
23 Jul 2025
Contributed by Lukas
Jesse welcomes back Peter Lazaroff to discuss the psychology and strategy of investing during uncertain times. They explore how media narratives and r...
When Smart Financial Planning Backfires - ChooseFI Companion Episode - E111
14 Jul 2025
Contributed by Lukas
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-optimizatio...
Buffett's Blueprint - 8 Examples of Warren's Timeless Wisdom - E110
02 Jul 2025
Contributed by Lukas
Jesse explores the timeless wisdom of Warren Buffett, highlighting both his disciplined investment philosophy and his unwavering emphasis on trust and...
Scrimping, Splurging, and Other Crazy Spending Stories - E109
18 Jun 2025
Contributed by Lukas
Jesse explores the value of financial priorities and the balance between spending and saving with guests Diania Merriam, Justin Peters, Bill Yount, Je...
Go Roth Now Before It's Too Late? And Other Listener Questions | AMA #7 - E108
04 Jun 2025
Contributed by Lukas
Jesse answers a range of listener questions on topics including estate planning, life insurance, financial benefits of marriage, tax strategies for hi...
19 Questions to Uncover Good, Bad, and Ugly Financial Advisors | Don McDonald - E107
21 May 2025
Contributed by Lukas
Today, Jesse is joined by Don McDonald to offer a critical examination of the financial advising and annuity industries, warning retirees and near-ret...
Retirees' Mistakes and Wake-Up Calls: Expectations vs. Reality - E106
07 May 2025
Contributed by Lukas
Jesse explores insights from the Retirements and Perspectives study, which captures the experiences and expectations of individuals transitioning into...
It's Not Too Late: Smart Money Moves After 50 | Bill Yount - E105
23 Apr 2025
Contributed by Lukas
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 ...
Tariffs, Turbulence, and the Harsh Truths We Must Now Face - Bonus Episode
14 Apr 2025
Contributed by Lukas
Today, Jesse critiques emotional, reactive investing during volatile market conditions—especially in response to tariffs and recession fears—while...
"Tax-Free Retirement" - Smart Strategy or Overhyped Gimmick? And Other Listener Questions | AMA #6 - E104
09 Apr 2025
Contributed by Lukas
Jesse answers listener questions on financial planning, investment management, and retirement. He discusses the challenges of rising homeowner's insur...
Life Expectancy, Caregiving Costs, & Retirement Planning | Christine Benz - E103
26 Mar 2025
Contributed by Lukas
Jesse Cramer speaks with Christine Benz, Director of Personal Finance at Morningstar, about insights from her book How to Retire. Before their discuss...
The Truth About the U.S. National Debt (And How It Impacts You Personally) - E102
12 Mar 2025
Contributed by Lukas
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 tra...
Do Long-Term Investors *Need* to Invest in Real Estate? | Chad "Coach" Carson - E101
26 Feb 2025
Contributed by Lukas
Jesse is joined by Chad Carson, who discusses residential real estate investing as a stable alternative to stocks and bonds. While real estate offers ...
Favorite Moments, Shoutouts, and a Name Change?! …From Our First 100 Episodes - E100
12 Feb 2025
Contributed by Lukas
Episode 100 of The Best Interest Podcast! This is a celebratory and reflective milestone featuring guest shout-outs, listener-favorite clips, and a di...
Will They Claw Back My Tax Breaks? Should I "Buy, Borrow, and Die?" And More - AMA #5 - E99
29 Jan 2025
Contributed by Lukas
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 circu...
What Do You Mean By "little p purpose"?! | Jordan Grumet - E98
15 Jan 2025
Contributed by Lukas
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 Bad "Money Scripts" Someone Else Wrote for You | Brad Klontz - E97
01 Jan 2025
Contributed by Lukas
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 ...
But is NOW the Right Time to Invest in the Stock Market?! - E96
18 Dec 2024
Contributed by Lukas
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 the...
Tax Loss Harvesting Myths Debunked: What You Need to Know Now | AMA #4 with Jesse - E95
04 Dec 2024
Contributed by Lukas
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 ...
Silly Hacks, New Rules, & Unpopular Opinions - E94
20 Nov 2024
Contributed by Lukas
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 ed...
Instructive and Surprising Questions to Ask Before You Retire | Joe Saul-Sehy - E93
06 Nov 2024
Contributed by Lukas
What are the long-term gains of educated investment decisions? The COVID pandemic triggered fear and uncertainty, with many wanting to sell everything...
Why Teachers Need to Be Careful | Dan Otter - E92
23 Oct 2024
Contributed by Lukas
Jesse opens the show by sharing a personal anecdote about a former teacher's challenging investment choices, which were burdened with high fees from t...
What No One Tells You About Early Retirement | Steve Adcock - E91
09 Oct 2024
Contributed by Lukas
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" sp...
No Diversification = Deep Trouble?! | AMA #3 with Jesse - E90
25 Sep 2024
Contributed by Lukas
Back with another AMA, Jesse tackles your questions on employee stock incentives, diversification, how taxes affect investments, and more! Our first q...
Societal Challenges and the "Money World" Don't Always Mix | Katie Gatti Tassin - E89
11 Sep 2024
Contributed by Lukas
Jesse explores the intricacies of student loan forgiveness, highlighting the fallacy that loans can simply vanish without consequence. He argues that ...
Practical Reasons Why "Retirement Success" Can Still Be Painful | Rob Berger - E88
28 Aug 2024
Contributed by Lukas
Referring back to his article, Fundamentals Of Retirement: Is the Summit "Good Enough?", Jesse uses an experience hiking in the Adirondack Mountains ...
How To Secure an Edge Against "Sequence of Returns" Risk | Tyler of Portfolio Charts - E87
14 Aug 2024
Contributed by Lukas
In today's opening monologue, Jesse explores the concept of Sequence of Returns Risk, a crucial and often misunderstood threat to retirees, by illustr...
Should I Drain My 401k to Pay Off My Mortgage? | AMA #2 with Jesse - E86
31 Jul 2024
Contributed by Lukas
In today's AMA, Jesse delves into various financial dilemmas and strategies to maximize benefits and secure a stable retirement. The first question co...
Red Flag Finance Scams on the Big, Scary Internet | Rachael Camp - E85
17 Jul 2024
Contributed by Lukas
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 quot...
How New Parents Can Avoid Money Mistakes | Andy Hill - E84
03 Jul 2024
Contributed by Lukas
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. Wh...
Fight, Flight, and Friction: Being Smart in Your Volatile Portfolio | Carl Richards - E83
19 Jun 2024
Contributed by Lukas
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 r...
"Truth: We Are Very Bad At Anticipating What We Want" | Jonathan Clements - E82
05 Jun 2024
Contributed by Lukas
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, mon...
"Is My 100% S&P 500 Portfolio Wrong?" | AMA #1 with Jesse - E81
22 May 2024
Contributed by Lukas
On today's episode, we bring you something a little different. Jesse's collected a series of questions from newsletter subscribers and will answer the...
Beware! Don't Fall Into "The College Money Pit Trap!" | Evan Giokas - E80
08 May 2024
Contributed by Lukas
Jesse starts this episode discussing his "50/50 rule" of college savings. Jesse also talks about 529-to-Roth conversions (why they're overrated!), the...
Health = Money = Time | Phil Pearlman - E79
24 Apr 2024
Contributed by Lukas
In episode 79 of The Best Interest Podcast, host Jesse Cramer discusses the intricate relationships between health, wealth, and time with guest Phil P...
An Informative Debate: The Most Important Rules of Personal Finance | Justin Peters - E78
10 Apr 2024
Contributed by Lukas
Jesse starts this episode with an engaging monologue: how exactly does The Best Interest generate revenue? Jesse answers this question and asks YOU fo...
A Market Crash is Coming! (…Eventually) | Peter Lazaroff - E77
27 Mar 2024
Contributed by Lukas
Peter Lazaroff is the host of The Long Term Investor podcast and serves as the Chief Investment Officer at PlanCorp, a registered investment advisory ...
Don't Make Your Own Pizza?! | Jared Dillian - E76
13 Mar 2024
Contributed by Lukas
Jared Dillian is a former Wall Street trader at Lehman Brothers, an author of 4 books, and daily writer a newsletter for financial professionals calle...
Growth Mindsets to Afford Anything | Paula Pant - E75
28 Feb 2024
Contributed by Lukas
Paula Pant writes, podcasts, and speaks on financial independence, money management, and financial literacy. As the host of the Afford Anything Podcas...
Picking Stocks - Does It Ever Work?! | Brian Feroldi - E74
14 Feb 2024
Contributed by Lukas
Brian Feroldi is a prolific creator in the financial education space, having written over 3000 articles for the Motley Fool, published a book, "Why Do...
People Need Informative Straight-Talk About Money (And Jokes, Too) | Joe Saul-Sehy - E73
31 Jan 2024
Contributed by Lukas
Joe Saul-Sehy is one of the hosts of Stacking Benjamins, which is one of the most listened-to podcasts in the personal finance space. In this episode,...
When Scary Career Risks Get Remarkable Results | Doug Cunnington - E72
17 Jan 2024
Contributed by Lukas
Today's show features Doug Cunnington, one of the hosts of the financial independence podcast Mile High FI. Doug highlights how he took conservative r...
The Unspoken Strain of F.I. | Diania Merriam - E71
03 Jan 2024
Contributed by Lukas
Diania Merriam is the founder of the EconoMe Conference, an exclusive gathering for the FIRE community (financial independence, retire early). Inspire...
The 7 Sins of Investing | Jeremy Schneider aka Personal Finance Club - E70
20 Dec 2023
Contributed by Lukas
Jeremy is the voice behind Personal Finance Club, a community of champions of the individual investor dedicated to bringing accessible financial educa...
529 Plans Aren't Worth It?! (And Other Important Tax Thoughts) | Sean Mullaney aka The FI Tax Guy - E69
06 Dec 2023
Contributed by Lukas
Sean Mullaney is the FI Tax Guy (FI = Financial Independence). He's a financial planner and the president of Mullaney Financial and Tax Incorporated w...
Minimalism: How Much is Enough? | Rose Lounsbury - E68
22 Nov 2023
Contributed by Lukas
Rose Lounsbury is a keynote speaker, an Amazon bestselling author, simplicity coach and the still-sane mom of triplets. She helps overwhelmed people c...
The Mindset of a Millionaire Next Door | Andrew Giancola - E67
08 Nov 2023
Contributed by Lukas
Today, Jesse shares some financial lessons from humble beginnings. There's much to learn from his first entrepreneurial endeavor: a baseball concessio...
Marriage, Kids and Money | Andy Hill - E66
25 Oct 2023
Contributed by Lukas
In the day-to-day hustle of parenting, thinking long-term, especially regarding finances, is often challenging. With studies showing an estimated cost...
Credit Card and Parenting Hacks | All the Hacks - E65
11 Oct 2023
Contributed by Lukas
Do you see yourself dying on top of a pile of gold like Scrooge McDuck? Today's guest, Chris Hutchins, shares his story of how he balances hacking his...
A Guide for the DIY Investor | Measure Twice Money - E64
27 Sep 2023
Contributed by Lukas
Nonillion… That's a number so big, I hadn't heard it before recording this episode. Should you budget and track every single dollar you spend? Shoul...
Saving Less to Live More. Should You Do the Same? | Carl Jensen aka Mr. 1500 - E63
13 Sep 2023
Contributed by Lukas
How do you know when you are taking the right financial road? Should you prioritize saving money to be better off in the future? Or is it more benefic...
The Reality of Retirement Beyond the Numbers | The Retirement Manifesto - E62
30 Aug 2023
Contributed by Lukas
Today on the podcast, we have a fascinating guest. He's a gentleman by the name of Fritz Gilbert. He runs a blog called The Retirement Manifesto. As y...
Are You Living a Regret Free Life? | Jordan Grumet aka Doc G - E61
17 Aug 2023
Contributed by Lukas
What exactly does it mean to live a regret free life? Our guest today, Jordan Grumet aka Doc G, shares the observations he's made as a hospice doctor....
Are You Saving Too Much? | with Nick Maggiulli - E60
02 Aug 2023
Contributed by Lukas
Today, I'm going to share the five false proxies leading people astray in their financial goals. In fact, what if I told you a recent study revealed y...
Think and Grow Rich…Really?! | How to Money and 5AM Joel - E59
19 Jul 2023
Contributed by Lukas
What kind of mood would you find yourself in if a tree fell onto your house? Would it ruin your day? Our guests might have something to say about that...
Why Inaction is an Investor's Best Friend - E58
05 Jul 2023
Contributed by Lukas
Today's episode starts in Minnesota, during an experiment where young men were intentionally starved. They knew starvation would affect their body, bu...
Does the Debt Ceiling Affect Your Finances? - E57
21 Jun 2023
Contributed by Lukas
You might've seen it on the nightly news or read it in the morning paper, but things got a little tense on Capitol Hill leading into Memorial Day week...
7 Facts That'll Change How You Invest in the Stock Market - E56
07 Jun 2023
Contributed by Lukas
Investing can be stressful. We worry when our accounts are going down and grow overconfident when our accounts are going up. So how do we find a good ...
Conversations with Aging Parents - E55
24 May 2023
Contributed by Lukas
Time is coming for us all, and according to one survey, 73% of adult children haven't had detailed conversations with their parents about their parent...
Choosing FI, with Brad Barrett - E54
10 May 2023
Contributed by Lukas
Today, we explore the concept of FIRE, a community of individuals dedicated to the principles of achieving financial independence and early retirement...
Roth vs. Traditional, and Other Vital Tax Topics - E53
26 Apr 2023
Contributed by Lukas
Three things are certain in life: death, taxes, and a couple weekly articles from The Best Interest. Today we explore the intersection of two of the m...
The Big Risk Staring You in the Face - E52
12 Apr 2023
Contributed by Lukas
Uncle Jim is certain Tesla stock is about to go up. He's been right before. I mean he's also been wrong, but only when something unpredictable happene...
Why is Personal Finance so Complicated?
06 Apr 2023
Contributed by Lukas
Why is personal finance so complicated? Even worse, the Internet is full of personal finance "experts" providing short-sighted, error-prone, and outri...
Insurance 101 - E51
29 Mar 2023
Contributed by Lukas
If a guy from Facebook messages you about whole life insurance more than your mom texts you, it's time to be suspicious. He may have more interest in ...
The Banking Collapse in Simple Terms - E50
15 Mar 2023
Contributed by Lukas
Bank runs, collapses, and bailouts. Anyone else getting GFC PTSD? The Silicon Valley Bank collapse is the largest bank collapse since the 2008 Great F...
Reviewing Warren Buffett's Latest Shareholder Letter - E49
01 Mar 2023
Contributed by Lukas
So what did Warren Buffett mean by silver tongued demagogues and slaying dragons? Jesse sits down with Rob Bradley, a fellow Berkshire Hathaway shareh...
Money is Simple...But Not Easy - E48
15 Feb 2023
Contributed by Lukas
Truth be told, personal finance is simple. There's only a small number of foundational rules and a sprinkle of middle school math involved. But o...
Is There a "War on Merit?" featuring The Financial Samurai - E47
01 Feb 2023
Contributed by Lukas
While the idea of living in a meritocracy is desirable, as it rewards those who do better, is it prevalent in today's society? With 25% of Americ...
9 Science-Backed Tips For Your 2023 Finances - E46
18 Jan 2023
Contributed by Lukas
2022 was a unique year for investors. Let's compare last year's bond and stock performances with historical trends to paint a bigger picture. Looking ...
A Terrific Interview - Jesse Cramer on "The Struggle is Real" - E45
04 Jan 2023
Contributed by Lukas
Big thanks to Justin Peters, from The Struggle is Real podcast, for allowing me to share this episode. A few months ago, Justin and I sat down to disc...
FTX Collapse, Lessons From My Honeymoon, and Why I Quit Social Media - E44
21 Dec 2022
Contributed by Lukas
FTX has been dominating the news. But what's a simple explanation of what happened? Jesse explains the sudden rise and fall of the FTX and its founder...
Omission and Paralysis - E43
13 Oct 2022
Contributed by Lukas
On this episode of the podcast, we discuss the hidden dangers of "analysis paralysis" in personal finance. And we discuss the "omission vs. commission...
Lollapaloozas - E42
28 Sep 2022
Contributed by Lukas
On this episode, we talk about rogue waves, rogue markets, and paying off debt. We also answer 4 cool listener questions, covering: - credit cards -...
Kanye West and Reader Questions - E41
21 Sep 2022
Contributed by Lukas
This episode features thoughts on Kanye West, and detailed answers to two terrific reader/listener questions. A few links: Original Kanye artic...
Did I Make an Investing Mistake? - E40
11 Sep 2022
Contributed by Lukas
In this episode, we talk about: - the college loan forgiveness program - "gardening" vs. "dining out," and how it applies to financial planning - a bl...