Personal Finance for Long-Term Investors
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Latest episodes
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The "Billionaire Moves" People Want to Copy (But Can They?) - (AMA, E154)
October 14, 2026 · 41 minLooking for a financial planner? → PlanWithJesse.com Jesse tackles a collection of "billionaire problems," examining financial strategies commonly associated with the ultra-wealthy and asking whether they are real, how they work, and…
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The Three Demons of Overconfidence - E153
October 7, 2026 · 28 minJesse explores the three "demons of overconfidence" that can quietly undermine investing and retirement decisions: overestimating our own skill, believing we are luckier than average, and assuming we are better at predicting the future…
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FIRE & Early Retirement Misconceptions (AMA, E152)
September 23, 2026 · 49 minLooking for a financial planner? → PlanWithJesse.com Jesse answers a new round of early-retirement questions, beginning with how investors can build a portfolio designed to last through a potentially long retirement. He explains why…
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Your Passive Portfolio Is More Active Than You Think - E151
September 9, 2026 · 42 minSure, you own index funds. But 99% of portfolios have a "shade of gray" that's more active than we realize. This episode dives into the "shades of gray" in passive investing and how they affect our portfolios and benchmarks. Looking for…
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*BIG* Career Changes & A Personal AMA | Jesse Cramer - E150
September 2, 2026 · 1 hr 4 minJesse shares an exciting new career update. And to celebrate 150 episodes, we're doing a unique AMA episode. Looking for a financial planner? → PlanWithJesse.com First, Jesse shares an exciting new career update. He has joined a new…
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Even Pros Make This Simple Tax Planning Error (AMA, E149)
August 26, 2026 · 37 minAn "Ask Me Anything" episode including questions like: Effective tax rates or marginal tax rates…which one matters? I'm at my retirement number, but this stock market is too crazy…should I adjust my portfolio? What about flexible…
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Is My DIY Financial Plan Working? - E148
August 12, 2026 · 38 minWe all know the importance of having a good financial plan in place. But…are we all talking about the same thing? What *is* a financial plan, and how do we know if ours is good or not? Looking for a financial planner? →…
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So, You're Retiring? Answering Common Questions from Soon-to-Be Retirees (AMA, E147)
August 5, 2026 · 45 minGliding into retirement raises dozens of questions - some about numbers, many about feelings. And listeners like you have many questions about that transition. Today's "Ask Me Anything" episode is dedicated to your retirement transition…
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What You're Missing on Your Investment Statements - E146
July 22, 2026 · 47 minYour monthly investment statements show what you own, how you've done, and some basic info. But there's so much info NOT included on your statement, and that's what we're diving into today! Looking for a financial planner? →…
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The Roth Conversion Checklist (AMA, E145)
July 8, 2026 · 54 minAre Roth conversions good for YOU? Why - or why not? Today's AMA episode is all about that topic. Looking for a financial planner? → PlanWithJesse.com In this Ask Me Anything episode, Jesse answers a wide range of listener questions…
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Are You Hoarding, Hustling, or Harvesting in Retirement? - E144
July 1, 2026 · 48 minRetirees struggle to transition from "hustling" and "hoarding" to "harvesting." It's costing them time. It's limiting their experiences and relationships. This isn't good. We need to understand why. Looking for a financial planner? →…
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The Three Things Money Can't Fix in Retirement (E143)
June 24, 2026 · 35 minYou've got the retirement numbers all figured out. You're set. But - how will you fill your time on random Tuesday in Year 4 of retirement? Do you have that kind of "soft stuff" figured out? If not, this episode is for you. Looking for a…

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