Instructive and Surprising Questions to Ask Before You Retire | Joe Saul-Sehy - E93
Personal Finance for Long-Term Investors - The Best Interest
Release Date: 11/06/2024
Buffett’s Blueprint - 8 Examples of Warren’s Timeless Wisdom - E110
Personal Finance for Long-Term Investors - The Best Interest
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 warnings about derivatives as speculative tools that undermine market integrity, and how Buffett built Berkshire Hathaway not just through smart investing, but through a foundation of honesty,...
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Scrimping, Splurging, and Other Crazy Spending Stories - E109
Personal Finance for Long-Term Investors - The Best Interest
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 of boat ownership, emphasizing the lesson to buy utility and rent luxury. Bill discusses the different seasons of life in relation to frugality and spending, while Jeremy reflects on ingrained...
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Go Roth Now Before It’s Too Late? And Other Listener Questions | AMA #7 - E108
Personal Finance for Long-Term Investors - The Best Interest
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 insurance is generally a poor investment choice for most people. He outlines how married couples enjoy more financial advantages due to shared costs, tax benefits, and retirement perks, though singles...
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19 Questions to Uncover Good, Bad, and Ugly Financial Advisors | Don McDonald - E107
Personal Finance for Long-Term Investors - The Best Interest
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 commission-based salespeople who often obscure fees, misrepresent guarantees, and use charm to build trust. Drawing from Jason Zweig’s “19 Questions to Ask Your Financial Advisor,” Jesse highlights...
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Retirees’ Mistakes and Wake-Up Calls: Expectations vs. Reality - E106
Personal Finance for Long-Term Investors - The Best Interest
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 follow. Authored by retirement experts Fritz Gilbert and Eric Weigel, the report dives into preparedness, lifestyle satisfaction, and evolving concerns. It reveals a common disconnect between what...
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It’s Not Too Late: Smart Money Moves After 50 | Bill Yount - E105
Personal Finance for Long-Term Investors - The Best Interest
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 advocating for steady, index-fund investing and disciplined budgeting. The episode also addresses market volatility and debunks the “buy the dip” strategy, showing that long-term consistency...
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Tariffs, Turbulence, and the Harsh Truths We Must Now Face - Bonus Episode
Personal Finance for Long-Term Investors - The Best Interest
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 growth or trigger stagflation. Market reactions, such as those seen during the Trump-era tariffs, highlight investor uncertainty and the self-inflicted nature of such economic disruptions. Jesse...
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"Tax-Free Retirement" - Smart Strategy or Overhyped Gimmick? And Other Listener Questions | AMA #6 - E104
Personal Finance for Long-Term Investors - The Best Interest
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 strategies and investment choices, and guides Chris, a federal worker, on pension decisions, TSP management, and career changes. Jesse also addresses Rachel’s concerns about bond funds versus individual...
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Life Expectancy, Caregiving Costs, & Retirement Planning | Christine Benz - E103
Personal Finance for Long-Term Investors - The Best Interest
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 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...
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The Truth About the U.S. National Debt (And How It Impacts You Personally) - E102
Personal Finance for Long-Term Investors - The Best Interest
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 inflation through taxation—though critics question the feasibility of this approach. While deficit spending can drive economic growth, excessive money printing may erode investor confidence. Interest...
info_outlineWhat 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, helping investors avoid costly mistakes. In contrast, a friend who sold his business for $10 million was initially hesitant to invest in the stock market due to a lack of education, but with advice to seek higher yields and follow a well-planned asset allocation strategy, he increased his earnings from 0.05% to 4.5% annually. Throughout Jesse’s monologue, he highlights examples where educated, deliberate, and disciplined decisions helped grow people’s portfolios and prepare them for their long-term goals.
Joe Saul-Sehy of Stacking Benjamins, returns to the podcast for the second half of the show. Jesse and Joe each brought 5 questions to ask before retirement - ideally long before retirement. Alternating, back and forth, they discover how few of these questions are about money. Sound investment and retirement planning isn’t just about the number going up, but also about what you’re going to do with the money you accumulate. Many of us plan to enjoy plenty of golfing during retirement, but, who among us can say we’d like to golf every day for 20 years? Join Jesse and Joe on an exploration of the questions you need to ask when planning your retirement.
Key Takeaways:
• Have you taken your mental and physical health into consideration when planning your retirement years?
• How long do you expect to be retired? And what do you plan to do with your time?
• Find something you can passionately be involved in during your retirement years.
• Why “chasing kids” isn’t a great retirement plan.
• How to simplify your savings plan and make the most of it.
• What engineers can teach us about planning for the unknown unknowns.
Key Timestamps:
(02:14) - Jesse’s Monologue: Putting a Dollar Sign on Financial Planning
(07:23) - Car Loan Decision Making
(08:24) - Backdoor IRA Contributions
(10:11) - Choosing the Right Home Location
(14:01) - Understanding Cash Balance Plans
(20:48) - Interview: Joe Saul-Sehy
(22:08) - Top Questions for Retirement Planning
(37:40) - Creative Solutions for Health Insurance in Retirement
(39:20) - Behavioral Aspects of Investing
(41:26) - The Fee Wars and Financial Planning
(45:36) - Asset Allocation and Investment Choices
(48:45) - Health and Healthcare in Retirement
(53:05) - Maintaining Relationships in Retirement
(57:46) - Protecting Yourself in Retirement
(01:01:06) - Giving Back to the Community
(01:07:58) - Conclusion and Podcast Information
Key Topics Discussed:
The Best Interest, Jesse Cramer, Rochester New York, financial planner, financial advisor, wealth management, retirement planning, tax planning, personal finance, retirement lifestyle, FIRE lifestyle, mental health, physical health
Mentions:
Website: https://www.stackingbenjamins.com/
LinkedIn: https://www.linkedin.com/in/joe-saul-sehy-b3426b31/
What Retirees Want: A Holistic View of Life's Third Age by Ken Dychtwald and Robert Morison
Keys to a Successful Retirement: Staying Happy, Active, and Productive in Your Retired Years by Fritz Gilbert
More of The Best Interest:
Check out the Best Interest Blog at bestinterest.blog
Contact me at [email protected]
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.