Personal Finance for Long-Term Investors

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 won't...

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...

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...

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...

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...

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...

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...

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...

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...

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...

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...

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...

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...

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...

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...

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...

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...

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...

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...

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-...

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...

Paula Pant writes, podcasts, and speaks on financial independence, money management, and financial literacy. As the host of the Afford Anything Podcast, Paula has racked up more than 30 million downloads, ranking the show among the Top 50 Business Podcasts on Apple Podcasts. In this episode we learn how Paula realized she could travel the world on a limited income and eventually go on to financial...

Brian Feroldi is a prolific creator in the financial education space, having written over 3000 articles for the Motley Fool, published a book, "Why Does The Stock Market Go Up?", and actively posting to his YouTube Channel. In this episode, Brian breaks down his checklist for what makes a company worth investing in and provides some insight into what we should do before we jump into investing. If...

Joe Saul-Sehy is one of the hosts of Stacking Benjamins, which is one of the most listened-to podcasts in the personal finance space. In this episode, we discuss how to find a good financial advisor, how to chase time (not money), and even how to decide what your top priority is in life. If you're looking for an educational listen with plenty of laughs along the way, then this is the episode for y...

Today's show features Doug Cunnington, one of the hosts of the financial independence podcast Mile High FI. Doug highlights how he took conservative risks along the way to FI, and walks us through his career journey to financial independence. We discuss misconceptions about the FIRE movement, how to prepare for financial emergencies, and why it's never too late to start your own journey to financi...