Personal Finance for Long-Term Investors

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...

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 tax rules, behavioral tendencies, and long-term strategy collide. He begins by unpacking a nuanced withdrawal-order debate, explaining why the "optimal" sequence between taxable, tax-deferred, and Roth accounts depends less on rigid rules and more on ta...

In this expansive and deliberately contrarian episode, Jesse takes on annuities—not with a sales pitch or a blanket dismissal, but by putting them under a rigorous planning lens rooted in risk, probability, and real retirement outcomes. He begins by laying out what annuities actually are, clearly separating fixed annuities from their variable cousins, and explaining why high fees, capped upside, i...

Jesse is joined by Cullen Roche—financial writer, macro thinker, and founder of Discipline Funds—for a clear-eyed conversation about how money actually works, why so much financial commentary gets it wrong, and how investors can make better decisions by understanding the plumbing beneath markets. Together, they unpack the core mechanics of the modern monetary system, including how government spend...

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 financial planning actually is—and what it is not. He begins by dismantling the common assumption that a portfolio and a financial plan are interchangeable, explaining why investing is only one component of a much broader process that aligns cash flow,...

In this candid solo episode, Jesse walks through a series of financial decisions that look "wrong" on paper but make complete sense when viewed through the lens of real life, values, and tradeoffs. Using personal examples, he challenges the idea that optimal spreadsheets should always dictate behavior, arguing instead that financial planning exists to support a life well lived—not to win theoretic...

Jesse is joined by Jeremy Keil—Certified Financial Planner, Chartered Financial Analyst, author of Retire Today, and host of the Retirement Revealed podcast—for a wide-ranging conversation that reframes how people should think about retirement decisions long before and long after the final day of work. Together, they explore why most people retire earlier than planned, why longevity is so often mi...

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 closer than ever. He begins with a thoughtful exploration of whether "this is the year to retire," unpacking how sequence-of-returns risk, market valuations, spending accuracy, and portfolio construction matter far more than trying to guess the next m...

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 his financial past, present, and future. He begins with the early experiences that formed his relationship with money: a summer concession stand that taught him pricing, customer focus, and the power of simply telling people what you do; a first job clea...

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 grounded look at the 15-year vs. 30-year mortgage debate, cutting through rules of thumb to show how interest rates, liquidity, cash-flow, and even your personal comfort with debt shape the right choice far more than blanket advice ever could. From th...

Jesse sits down with Andy Hill—personal finance educator, podcast host, and creator of Marriage, Kids, and Money—for a candid conversation about building wealth while building a life you actually enjoy. Andy shares how a mix of financial discipline, intentional goal-setting, and family-centered values helped him and his wife pay off their mortgage by age 35 and achieve financial independence on th...

Today, Jesse is joined by Dr. Phil Pearlman—psychologist, behavioral finance veteran, and founder of the Pearl Institute—for a conversation about how long-term health and long-term wealth are two sides of the same coin. Together, they explore why the holiday season, while full of joy and connection, is also the unhealthiest stretch of the year for most Americans—and how small, deliberate choices c...

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 a deep dive into direct indexing, separating substance from sales pitch. While advocates tout it as the next evolution of indexing—combining personalization and tax-loss harvesting—Jesse explains why, for most investors, the extra complexity, cost, a...