Personal Finance for Long-Term Investors
A personal finance, retirement, and investing podcast hosted by Jesse Cramer, a former aerospace engineer turned fiduciary financial advisor in Rochester, New York. Each episode breaks down complex financial planning topics using relatable stories, in-depth research, and practical tips. The show focuses on long-term strategies rather than short-sighted advice, covering tax-efficient investing, family financial planning, optimal investment allocations, retirement planning, and generational wealth transfer. Formerly known as The Best Interest Podcast, it grew out of Jesse's award-nominated blog The Best Interest. The goal is to make personal finance approachable, enjoyable, and actionable for long-term investors.
Episodes
The "Billionaire Moves" People Want to Copy (But Can They?) - (AMA, E154)
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
The Three Demons of Overconfidence - E153
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
FIRE & Early Retirement Misconceptions (AMA, E152)
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
Your Passive Portfolio Is More Active Than You Think - E151
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
*BIG* Career Changes & A Personal AMA | Jesse Cramer - E150
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 Pe
Even Pros Make This Simple Tax Planning Error (AMA, E149)
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
Is My DIY Financial Plan Working? - E148
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
So, You're Retiring? Answering Common Questions from Soon-to-Be Retirees (AMA, E147)
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
What You're Missing on Your Investment Statements - E146
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
The Roth Conversion Checklist (AMA, E145)
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 t
Are You Hoarding, Hustling, or Harvesting in Retirement? - E144
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
The Three Things Money Can't Fix in Retirement (E143)
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
Stop Eating! It's Costing You BILLIONS! (AMA #17) - E142
"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
The 14 Retirement Risks - And How to Beat Them (Pt 2) - E141
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 financia
The 14 Retirement Risks - And How to Beat Them (Pt 1) - E140
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
Debate! ...Taking Sides On 10 Retirement Sub-Topics (E139)
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
Making Retirement As Simple as Possible, but No Simpler (AMA, E138)
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: More Flawed Than Advertised (E137)
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
He Retired Early - Here's What No One Warned Him About (E136)
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
Why Trump Accounts Fall Short (AMA, E135)
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
Even Financial Advisors Misunderstand Monte Carlo Retirement Analysis (E134)
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
Uncomfortable Truth: Great Investing Decisions Can Look Wrong For Years (E133)
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
Are You in a "Goldilocks" Retirement Range? (E132, AMA)
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
Less Wealth, More Certainty: Why Annuities Are Rarely Worth It (E131)
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
Don't Let a Scary Economy Cause Bad Retirement Decisions (E130)
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
"Isn't My Portfolio the Same as My Financial Plan??" (AMA, E129)
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,
11 "Bad" Financial Moves...That Are Actually Fine (E128)
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
"The Most Important Number" in Your Retirement?! (E127)
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
Will You Retire in 2026?? (AMA, E126)
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
My Ghosts of Financial Past, Present, and Future (E125)
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
The Scenario When HSA's Are a *BAD* Account (AMA, E124)
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
Should "Coast FI" Be the *Real* Goal? (E123)
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
Why Retirees Struggle with Health Over the Holidays (E122)
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
The Optimal Retirement Withdrawal Framework, Account by Account (AMA, E121)
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
A New Predator Coming For Our Retirement Dollars (E120)
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, and
Special Needs Children - Financial 101 for their Parents and Grandparents (E119)
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
"How Does a $1M Inheritance Help My Early Retirement Dream?" (AMA, E118)
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
Leaving the Workforce? Your Identity Will Shift in Uncomfortable Ways (E117)
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 Financia
Which of Your "Money Scripts" Are Helpful vs. Hurtful? (E116)
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
Where Investors Go Wrong: Tax Traps, Math Mistakes, and Behavioral Biases (E115)
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
The Risks of Quitting Your Career (E114)
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
"How Will Taxes Affect My Inheritance Planning?" (AMA, E113)
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,
Reset Your Portfolio Expectations, Before It's Too Late (E112)
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
The Risks of *Over*-Optimizing Your Retirement (E111)
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
8 Examples of Warren Buffett's Timeless Wisdom (E110)
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
6 Experts Share Their "Worst" Spending Stories (E109)
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
Go Roth Now Before It's Too Late? (AMA, E108)
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
19 Questions to Uncover Good, Bad, and Ugly Financial Advisors (E107)
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
The Big Disconnect: Pre-Retiree Expectations vs. Retirement Reality (E106)
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
Smart Money Moves After "Starting Late" (E105)
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
Tariffs, Turbulence, and Harsh Truths (E104)
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
"Tax-Free Retirement" - Smart Strategy or Overhyped Gimmick? (AMA, E104)
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
Will Caregiving Costs Derail Your Plan? (E103)
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
U.S. National Debt: Truths, Myths, and Its Impact On You (E102)
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
Do Long-Term Investors Need Real Estate Investments? (E101)
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,
Favorite Moments from the First 100 Episodes (E100)
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
How Do Ultra-Wealthy People "Buy, Borrow, and Die?" (AMA, E99)
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
Most People Don't Have a Good "Purpose Anchor" (E98)
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
How Great-Grandma Makes You a Worse Investor (E97)
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
Just Stop! On "Beating" and "Timing" the Market (E96)
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 market? The truth is, the timeless advice stands: diversify your portfolio, steer clear of speculation, and invest early and often. Diversifying is like buying the haystack, rather than looking for the needle, because, the truth is, you probably wo
Tax Loss Harvesting Debunked (AMA, E95)
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 when. Dan seeks clarity on bonds' role despite recent poor returns, learning they offer portfolio stability and mitigate market volatility, critical for risk-averse investors. Peter asks about Social Security timing, highlighting the trade-off betwee
100% Stocks for All Retirement?! (E94)
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 education. In this episode, you'll hear why side hustles might just be a waste of time, what makes detailed budgeting overrated, and how you're actually spoiled just by having a queen sized bed! This episode is great if you're looking for a few reminde
Instructive and Surprising Questions to Ask Before You Retire | Joe Saul-Sehy - E93
What are the long-term gains of educated investment decisions? The COVID pandemic triggered fear and uncertainty, with many wanting to sell everything amid the stock market's 30% drop. However, disciplined investors maintained their perspective and followed their investment policy. This approach, coupled with proper financial planning, often results in a stronger portfolio after market crashes, he
Why Teachers Need to Be Careful | Dan Otter - E92
Jesse opens the show by sharing a personal anecdote about a former teacher's challenging investment choices, which were burdened with high fees from their financial advisor. He emphasizes the predatory nature of the financial advice teachers receive, encouraging teachers to seek better investment options from reputable firms like Vanguard and Fidelity. Finally, Jesse underscores the importance of
What No One Tells You About Early Retirement | Steve Adcock - E91
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" speech, he highlights our self-centered bias and makes suggestions on how we can gain greater perspective through the support of those around us. In his monologue, Jesse also notes Charlie Munger's belief that the world isn't driven by greed, but rathe
No Diversification = Deep Trouble?! | AMA #3 with Jesse - E90
Back with another AMA, Jesse tackles your questions on employee stock incentives, diversification, how taxes affect investments, and more! Our first question comes from Lynn, who asks about when to take Social Security, which opens up a broader discussion on optimal timing for retirement benefits. While she and her husband initially planned to wait until age 70 to maximize benefits, based on famil
Societal Challenges and the "Money World" Don't Always Mix | Katie Gatti Tassin - E89
Jesse explores the intricacies of student loan forgiveness, highlighting the fallacy that loans can simply vanish without consequence. He argues that the financial burden ultimately falls on taxpayers and critiques the notion that the U.S. government can "magically" eliminate student debt. Jesse explains the Public Service Loan Forgiveness (PSLF) program and how student debt exacerbates mental hea
Practical Reasons Why "Retirement Success" Can Still Be Painful | Rob Berger - E88
Referring back to his article, Fundamentals Of Retirement: Is the Summit "Good Enough?", Jesse uses an experience hiking in the Adirondack Mountains as a metaphor to explore retirement preparedness. He recounts how being poorly equipped for a challenging hike can mirror the pitfalls of entering retirement without thorough planning - you might reach the summit, but the journey and destination may n
How To Secure an Edge Against "Sequence of Returns" Risk | Tyler of Portfolio Charts - E87
In today's opening monologue, Jesse explores the concept of Sequence of Returns Risk, a crucial and often misunderstood threat to retirees, by illustrating how poor returns early in a retirement can severely impact long-term stability. He emphasizes the importance of diversification. Jesse then introduces the idea of path dependence, drawing parallels to the life of author Philip K. Dick, whose po
Should I Drain My 401k to Pay Off My Mortgage? | AMA #2 with Jesse - E86
In today's AMA, Jesse delves into various financial dilemmas and strategies to maximize benefits and secure a stable retirement. The first question comes from Mindy, a 50-year-old widow, weighing the pros and cons of remarrying due to its potential impact on her survivor benefits. Jesse explains the complexities of Social Security spousal and survivor benefits, urging listeners to consult with a C
Red Flag Finance Scams on the Big, Scary Internet | Rachael Camp - E85
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 quote, "The future is already here. It's just not evenly distributed, yet." Jesse draws a connection between Gibson's quote and the distribution of financial literacy, explaining that The Best Interest is part of the distribution effort. Of course, there ar
How New Parents Can Avoid Money Mistakes | Andy Hill - E84
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. While money is important, it is ultimately a means to gain the freedom to spend time with those you care about. In his second reflection, Jesse recounts the story of his parents' neighbors' house catching fire, highlighting the importance of risk manag
Fight, Flight, and Friction: Being Smart in Your Volatile Portfolio | Carl Richards - E83
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 right financially, prioritizing spending, working hard, and remembering that others have walked this path. Then, with another call back to his blog, Jesse invokes Marshall McLuhan's quote "the medium is the message" when sharing from his post, "The
"Truth: We Are Very Bad At Anticipating What We Want" | Jonathan Clements - E82
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, money can certainly buy flexibility and optionality. Jesse collects insights from Thom Yorke, Matthew Killingsworth, Danny Kahneman, and Angus Deaton. Today's guest is Jonathan Clements, the founder and editor of Humble Dollar, the author of My Money
"Is My 100% S&P 500 Portfolio Wrong?" | AMA #1 with Jesse - E81
On today's episode, we bring you something a little different. Jesse's collected a series of questions from newsletter subscribers and will answer them in today's AMA (Ask Me Anything). Jesse answers into which accounts young people should be putting their money. Other questions answered are: Is getting to your "Coast FI" a good idea? How to balance which accounts you're putting money into and how
Beware! Don't Fall Into "The College Money Pit Trap!" | Evan Giokas - E80
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 FAFSA, and other financial tools at our disposal for college planning. Evan Giokas then joins the show to dive deeper into a college admissions conversation. Evan is the founder of The College Confidence Coach, which helps students through their
Health = Money = Time | Phil Pearlman - E79
In episode 79 of The Best Interest Podcast, host Jesse Cramer discusses the intricate relationships between health, wealth, and time with guest Phil Pearlman. Jesse starts with his usual monologue, explaining and establishing that health, money, and time are all interchangeable resources that many people trade-off throughout their lives. Jesse and Phil then delve into how health decisions signific
How *YOU* Help This Podcast Keep Going (E78)
Jesse starts this episode with an engaging monologue: how exactly does The Best Interest generate revenue? Jesse answers this question and asks YOU for your help in ensuring The Best Interest continues as a terrific free financial resource. And then Justin Peters joins for the second half of the episode. Justin hosts The Struggle is Real, a podcast about adulting through your twenties. He's als
A Market Crash is Coming! (…Eventually) | Peter Lazaroff - E77
Peter Lazaroff is the host of The Long Term Investor podcast and serves as the Chief Investment Officer at PlanCorp, a registered investment advisory in St. Louis. On today's show, Jesse and Peter talk about the cognitive challenge of investing at all-time highs. It's normal to feel like a crash might be coming; but it always feels that way, and you shouldn't be worried about it. If you're a long-
Don't Make Your Own Pizza?! | Jared Dillian - E76
Jared Dillian is a former Wall Street trader at Lehman Brothers, an author of 4 books, and daily writer a newsletter for financial professionals called The Daily Dirtnap. He's sharp, witty, and brings great energy to today's conversation. In this episode of The Best Interest Podcast, we learn about "The Allegory of the Sandwich" and how you can pay for the small stuff by thinking carefully about t
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