Personal Finance for Long-Term Investors

Today, Jesse is joined by Professor John Dinsmore—behavioral finance researcher, marketing scholar, and author of The Marketing of Debt: How They Get You —for a conversation about how persuasion, psychology, and modern advertising quietly shape our financial lives. Together, they explore how marketers exploit human biases like loss aversion, anchoring, and over-optimism to sell products, loans, an...

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 his daughter's illness—an experience that deepened his empathy for parents whose caregiving journeys never pause—and uses it to frame the emotional and financial realities families face when raising a child with disabilities. From there, he explores ho...

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 that age alone dictates portfolio strategy, emphasizing instead that time horizons, goals, and diversification determine the right balance between growth and preservation. From there, Jesse advises a listener who recently inherited $1 million on how to...

Today, Jesse is joined by Spencer Reese—Air Force veteran, financial educator, and creator of the Military Money Manual —for a conversation about the surprising overlap between military transitions and civilian retirement. Together, they explore why the only constant in retirement is change, how life evolves through "go-go, slow-go, and no-go" phases, and Jesse's framework for a "Retiree's Financi...

Today, Jesse is joined by Hanna Horvath—Certified Financial Planner, managing editor at Bankrate, and author of the Your Brain on Money newsletter—for a deep dive into the psychology behind our financial decisions and why money is never just about numbers. Together, they explore how unconscious "money scripts" formed in childhood shape lifelong habits, why emotional discipline matters more than wi...

Today, Jesse goes solo for a candid episode unpacking the most common mistakes and misconceptions he sees in personal finance, from the temptation to "rip off the bandaid" with Roth conversions to the behavioral traps of availability bias and flawed math around investment returns. He breaks down a real listener case study to show why paying millions in unnecessary taxes up front rarely makes sense...

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 building a successful online personal finance brand, emphasizing the importance of leveraging scalable income streams to achieve financial freedom. Kelan explains how entrepreneurship allows for more growth compared to a traditional nine-to-five by leveragi...

Jesse tackles six thoughtful listener questions spanning a range of personal finance topics. He begins with a question about using Social Security and pension payments as a means to replace bonds in a retirement portfolio. Why do we own bonds, anyway? Then Jesse dives into long-term care insurance, a common sticky topic for aging retirees. Do they need to earmark dollars for long-term care? Next,...

Jesse welcomes back Peter Lazaroff to discuss the psychology and strategy of investing during uncertain times. They explore how media narratives and recession fears can distort investor behavior, emphasizing the importance of focusing on business earnings rather than sensational headlines. Peter shares why he separates his portfolio thinking from his balance sheet management, especially during pot...

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-optimization in personal finance, concentrating on tax-loss harvesting, asset allocation, Roth conversions, and dividend investing. He explains how each strategy can offer value when used thoughtfully, but warns that many DIY investors misuse them—chasing tax s...

Jesse explores the timeless wisdom of Warren Buffett, highlighting both his disciplined investment philosophy and his unwavering emphasis on trust and character. Jesse breaks down Buffett's approach to buying great businesses at fair prices, holding them long-term, and focusing on intrinsic value, margin of safety, and staying within one's circle of competence. He also examines Buffett's early war...

Jesse explores the value of financial priorities and the balance between spending and saving with guests Diania Merriam, Justin Peters, Bill Yount, Jeremy Schneider, Doc G, and Joe Saul-Sehy. Diania highlights the "iceberg principle" of stealth wealth—how true wealth is often what you don't see, like deferred purchases and unspent money. Justin shares a personal story about the cost and memories o...

Jesse answers a range of listener questions on topics including estate planning, life insurance, financial benefits of marriage, tax strategies for high earners, healthcare in retirement, and investing during economic uncertainty. He explains that heirs to traditional IRAs must pay income tax on withdrawals, while taxable accounts benefit from a step-up in basis, and argues that whole life insuran...

Today, Jesse is joined by Don McDonald to offer a critical examination of the financial advising and annuity industries, warning retirees and near-retirees about misleading sales tactics that exploit fear - especially the fear of market losses. They emphasize the importance of working with fee-only, fiduciary advisors who are legally obligated to act in clients' best interests, in contrast to comm...

Jesse explores insights from the Retirements and Perspectives study, which captures the experiences and expectations of individuals transitioning into retirement, especially those aged 50 to 75. With half of the participants recently retired and the other half preparing to retire within two years, the study offers a timely look at the "final glide path" into retirement and the early years that fol...

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 "Stupidly Simple Secret Sauce" for personal finance: spend less than you earn, grow income without inflating lifestyle, invest consistently, and prioritize savings. He warns against flashy success stories, consumer culture, and speculation, instead a...

Today, Jesse critiques emotional, reactive investing during volatile market conditions—especially in response to tariffs and recession fears—while promoting disciplined, evidence-based strategies. Tariffs, though intended to protect domestic industries, often raise prices and stoke inflation, ultimately harming consumers, businesses, and investor sentiment, with economists warning they may slow gr...

Jesse answers listener questions on financial planning, investment management, and retirement. He discusses the challenges of rising homeowner's insurance costs in high-risk areas, the differences between Treasuries, CDs, and high-yield savings accounts, and the inefficiencies of using life insurance for tax-free retirement. He advises Casey, a future retiree, on tax-efficient withdrawal strategie...

Jesse Cramer speaks with Christine Benz, Director of Personal Finance at Morningstar, about insights from her book How to Retire. Before their discussion, Jesse contrasts gambling with long-term investing, emphasizing the risks of short-term market bets versus the reliability of patient investing. Christine highlights the shift in financial advice toward holistic retirement planning, including the...

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 traces the debt's history and explains its structure, funding through Treasury bonds, and refinancing process. The discussion covers Modern Monetary Theory (MMT), which suggests that as a currency issuer, the U.S. cannot default but must manage inflatio...

Jesse is joined by Chad Carson, who discusses residential real estate investing as a stable alternative to stocks and bonds. While real estate offers advantages like rental income, property appreciation, and tax benefits, Jesse also highlights challenges such as high costs, tenant issues, liquidity problems, and the time commitment required. Jesse thinks of his Rochester wealth management clients,...

Episode 100 of The Best Interest Podcast! This is a celebratory and reflective milestone featuring guest shout-outs, listener-favorite clips, and a discussion on the show's evolution. Jesse shares the podcast's origins, his journey from aerospace engineering to financial planning, and how the podcast nearly faded before finding renewed purpose in 2023. Throughout the episode, Joe Saul Sehy, Brian...

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 circumstances. Jesse explores relativity, "keeping up with the Joneses", and what it means to have "enough". Then, Bob asks about the potential tax burdens on beneficiaries and heirs, and Tom wonders whether some tax savings are worth the effort of logist...

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 seemingly less significant latter. Bringing together his experience in hospice care and finance, Jordan shines light on how we can create our purpose through personal growth and the pursuit of passions, rather than grandiose goals. Jordan calls these...

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 all. Emotional stability and disciplined decision making outweigh expertise and intelligence when investing. The Dunning-Kruger effect and the paradox of choice are also highlighted, emphasizing the need to prioritize action over perfection in person...