Personal Finance for Long-Term Investors

Jesse explores one of the most important questions in retirement planning: What problem are you actually trying to solve? Maximize success? Or minimize failure? Looking for a financial planner?  → PlanWithJesse.com Drawing on his background in aerospace engineering, Jesse explains how competing goals require trade-offs and why optimizing one part of a financial plan can create problems elsewhere....

Jesse explores the fascinating history of retirement in America, tracing its evolution from a time when most people worked until they physically couldn't to today's complex system of Social Security, Medicare, employer-sponsored retirement plans, and personal savings. Looking for a financial planner?  → PlanWithJesse.com Jesse explains how the Industrial Revolution introduced corporate pensions, h...

13 of Charlie Munger's best quotes guide today's episode, covering investing, thinking, and how to live a smarter life.   Looking for a financial planner?  → PlanWithJesse.com   Jesse turns to the wisdom of Charlie Munger, drawing primarily from Poor Charlie's Almanack to explore 13 ideas that can improve how we approach investing, retirement planning, and life more broadly. From compounding knowl...

Looking 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 whether ordinary retirees should consider using them. He begins by exploring why wealthy Americans can face very different effective tax burdens than wage earners, i...

Jesse 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 than we really are.  Looking for a financial planner?  → PlanWithJesse.com Drawing on ideas from psychologist Daniel Crosby and behavioural research, he explains ho...

Looking 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 focusing narrowly on dividends, interest, or other forms of "income generation" can lead retirees toward mathematically suboptimal decisions, and why total return, ri...

Sure, 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 a financial planner?  → PlanWithJesse.com Jesse explores an important distinction that many investors overlook: owning passive funds does not necessarily mean you...

Jesse 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 financial planning firm - as an advisor and an owner. The new firm, Rialto, is focused on serving people JUST like those who read *The Best Interest* and listen to  P...

An "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 spending rules in retirement? Which are good, which aren't, and how to use them in practice.  Looking for a financial planner?  → PlanWithJesse.com Jesse answers three l...

We 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?  → PlanWithJesse.com Jesse explores what financial planning actually is, why it extends far beyond investing, and how to know whether your financial plan is truly working. He begins...

Gliding 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 questions.  Looking for a financial planner?  → PlanWithJesse.com In this Ask Me Anything episode, Jesse answers listener questions about the financial and emotion...

Your 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?  → PlanWithJesse.com Jesse explains why your quarterly investment statement tells only a fraction of your portfolio's true story, and why investors who stop at account balances...

Are 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 about Roth conversions, moving beyond the basic mechanics to explore the nuanced trade-offs that determine whether a conversion creates value or simply accelerates...

Retirees 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?  → PlanWithJesse.com Jesse is joined by Frank Vasquez—retired attorney, creator of Risk Parity Radio, and one of the most distinctive voices in the retirement planning...

You'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 financial planner?  → PlanWithJesse.com In this episode, Jesse challenges the traditional, finance-centric view of retirement by arguing that long-term financial...

"Opportunity cost" analysis could make you think that every dollar you spend is ruining your future retirement finances. We address this way of thinking in today's "Ask Me Anything" episode.  Looking for a financial planner?  → PlanWithJesse.com Jesse explores three listener questions spanning core retirement planning tradeoffs. First, he unpacks the concept of opportunity cost, arguing that while...

We all want retirement success. But how do we achieve it? What if the best method is to identify possible *failures* first, and then simply work backward to avoid those failures?  Looking for a financial planner?  → PlanWithJesse.com In this follow-up episode, Jesse completes his inversion-based framework for retirement planning by outlining the remaining risks that can derail long-term financial...

We all want retirement success. But how do we achieve it? What if the best method is to identify possible *failures* first, and then simply work backward to avoid those failures?  Looking for a financial planner?  → PlanWithJesse.com In this episode, Jesse applies Charlie Munger's principle of inversion to retirement planning, arguing that instead of only defining success, investors should first i...

We dive into 10 common retirement topics and debate two sides of the argument. You'll walk away with a better understanding of how to make decisions in your retirement plan.  Looking for a financial planner?  → PlanWithJesse.com Jesse is joined by Andrew Giancola—host of The Personal Finance Podcast—for a fast-paced, opinionated conversation tackling some of the most debated ideas in investing and...

Retirement planning doesn't need to be rocket science. But it's also not ABCs and 123s. There's a middle ground of simplicity, but not over-simplicity. That's the topic on today's Ask Me Anything episode.  Looking for a financial planner?  → PlanWithJesse.com In this Ask Me Anything episode, Jesse explores the delicate balance between overcomplicating and oversimplifying financial decisions in ret...

Target date funds can be good. But most are not. That's the uncomfortable fact we'll dive into in today's episode.  Looking for a financial planner?  → PlanWithJesse.com Jesse delivers a critical re-evaluation of target date funds—one of the most widely used "set-it-and-forget-it" retirement tools—arguing that while their simplicity is appealing, their real-world performance often falls short in m...

In today's replay of episode 62, Jesse is joined by Fritz Gilbert—retirement blogger behind The Retirement Manifesto and former corporate executive turned early retiree—for a candid and experience-driven conversation about what retirement actually feels like after the spreadsheets are closed and the plan becomes real life. Fritz shares the story behind his early retirement decision, including the...

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 decisions in a world full of new ideas, policy noise, and competing priorities—starting with a breakdown of "Trump accounts" and what they actually mean for real planning. Rather than reacting to the headline, he walks through how to analyze any new or p...

In this technical deep dive, Jesse pulls back the curtain on one of the most commonly cited tools in retirement planning—Monte Carlo analysis—explaining what it actually does, how it works under the hood, and why its outputs are often misunderstood. He begins by contrasting Monte Carlo simulations with simpler "static" retirement calculators and deterministic cash-flow projections, showing why mod...

Jesse is joined by Rubin Miller—former Dimensional Fund Advisors insider, founder and CIO of Peltoma Capital Partners, author of the Fortunes and Frictions blog, and national chess master—for a wide-ranging conversation about how investment philosophy, behavioral discipline, and real-world client psychology intersect. Rubin pulls back the curtain on how factor tilts like small-cap, value, and prof...