Life Expectancy, Caregiving Costs, & Retirement Planning | Christine Benz - E103
Personal Finance for Long-Term Investors - The Best Interest
Release Date: 03/26/2025
Jesse’s Ghosts of Financial Past, Present, and Future | E125
Personal Finance for Long-Term Investors - The Best Interest
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 cleaning bathrooms at a state park that clarified the difference between earning a paycheck and building a career; and the moment in his mid-20s when seeing real dollars in his 401(k) pulled him...
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Dying With an HSA, Mystery Mortgage Math, & Should DIY Investors Hire a Planner? | AMA #11 - E124
Personal Finance for Long-Term Investors - The Best Interest
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 there, he turns to the under-discussed strategy behind Health Savings Accounts—why the “invest and reimburse later” approach works, when it stops working, and how the tax bomb of leaving HSA...
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Feeling Time Poor? The Journey to Owning Your Time | Andy Hill - E123
Personal Finance for Long-Term Investors - The Best Interest
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 their own terms. Together, they unpack why traditional FIRE goals often miss the human side of money, how to define “enough,” and why generosity and purpose are essential parts of financial...
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Health and Wealth - The Power of a “Bigger Yes” | Phil Pearlman - E122
Personal Finance for Long-Term Investors - The Best Interest
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 can reverse that trend. Phil shares his “four pillars of health”—nutrition, exercise, sleep, and love/community—alongside his own powerful story of addiction, recovery, and rediscovering...
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Retire Confidently With A Proven Drawdown Framework | AMA #10 - E121
Personal Finance for Long-Term Investors - The Best Interest
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, and tracking error outweigh the modest tax advantages, making low-cost ETFs the better long-term choice. Next, he answers a question from a listener whose retirement timeline doesn’t align...
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Marketing Algorithms Are Coming For Your Retirement Dollars | John Dinsmore - E120
Personal Finance for Long-Term Investors - The Best Interest
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 debt, and why AI-driven “adaptive ads” are making it harder than ever to recognize when we’re being influenced. John shares real-world examples—from car dealerships to “buy now, pay...
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Special Needs Children: How to Protect Their Future and Yours - E119
Personal Finance for Long-Term Investors - The Best Interest
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 how special needs planning extends beyond traditional wealth management, requiring families to think in decades, not years, while balancing their own retirement goals with lifelong care needs....
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The Only Free Lunch in Investing (Maybe) | AMA #9 - E118
Personal Finance for Long-Term Investors - The Best Interest
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 integrate the windfall into an early retirement plan through detailed cash flow projections, withdrawal strategies, and careful consideration of pensions and Social Security. Next, he unpacks the...
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Military Money Lessons That Civilians Can’t Afford to Miss | Spencer Reese - E117
Personal Finance for Long-Term Investors - The Best Interest
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 Financial Decathlon,” covering everything from building a sustainable paycheck to tax efficiency, healthcare, estate planning, and even learning to spend with intention. Spencer shares lessons...
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Manage *Yourself* More Than Your Portfolio | Hanna Horvath - E116
Personal Finance for Long-Term Investors - The Best Interest
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 willpower, and how anxiety shows up even for people who have “won the game” financially. Hanna explains how retirement brings not just financial questions but also an identity shift, making...
info_outlineJesse 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 importance of low-cost, diversified portfolios and planning for life transitions. The episode also explores the financial impact of caregiving, particularly on women, and the necessity of proactive retirement savings and long-term care planning. John Guyton’s "guardrails approach" is discussed as a strategy for adjusting withdrawals based on market performance. Additionally, the conversation underscores the role of psychology in financial decision-making and the non-financial aspects of retirement, such as maintaining social connections and redefining work-life balance. The overarching message is that successful retirement planning requires a combination of careful financial preparation, behavioral awareness, and long-term strategic thinking.
Key Takeaways:
• Short-term stock market movements may seem random, but long-term investing historically trends upward, making it a safer and more strategic approach compared to gambling.
• Many people underestimate their lifespan, which can lead to financial shortfalls in retirement; actuarial data and family history should be factored into planning.
• Persuasive stories can shape financial decision-making, sometimes leading people to overlook critical advice in favor of compelling but misleading pitches.
• Taking on unpaid caregiving roles can impact financial security, and couples should consider financial agreements to ensure fair distribution of assets.
• Beyond finances, maintaining social connections and finding purpose are crucial for a satisfying retirement.
• A successful retirement is not just about financial security but also about ensuring a meaningful and well-balanced life in later years.
Key Timestamps:
(00:00) Casino vs. Investment
(11:09) Understanding Life Expectancy for Retirement
(15:29) The Man Who Never Looked Up
(20:41) Interview with Christine Benz
(23:06) The Shift to Holistic Planning
(23:47) Consumer Investment Preferences
(24:26) Christine's Book: How to Retire
(25:04) Personal Story: Christine's Parents
(27:16) The Role of Financial Planners
(30:24) Flexible Financial Planning Models
(39:46) Retirement Planning for Women
(45:28) Navigating Retirement as a Couple
(47:24) Insights from The Long View Podcast
(49:17) Conclusion and Contact Information
Key Topics Discussed:
The Best Interest, Jesse Cramer, Rochester New York, financial planner, financial advisor, wealth management, retirement planning, tax planning, personal finance
Mentions:
Website: https://www.morningstar.com/podcasts/the-long-view
LinkedIn: https://www.linkedin.com/in/christine-benz-b83b523/
Mentions:
https://bestinterest.blog/how-long-will-you-live/
https://bestinterest.blog/some-bets-im-willing-to-make/
https://bestinterest.blog/the-man-who-never-looked-up/
More of The Best Interest:
Check out the Best Interest Blog at bestinterest.blog
Contact me at jesse@bestinterest.blog
The Best Interest Podcast is a personal podcast meant for educational and entertainment. It should not be taken as financial advice, and is not prescriptive of your financial situation.