Practical Reasons Why "Retirement Success" Can Still Be Painful | Rob Berger - E88
Personal Finance for Long-Term Investors - The Best Interest
Release Date: 08/28/2024
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_outlineReferring 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 not be as enjoyable. Sharing the example of a couple, John and Eva, who are on the brink of retirement with substantial assets and a solid financial plan, Jesse raises critical questions about their investment strategy, withdrawal plans, and tax considerations, suggesting that while they are well-positioned, their retirement journey could be smoother with additional preparation.
For today’s interview, Jesse is joined by Rob Berger. Rob is a contributing editor for Forbes Advisor, host of the Financial Freedom Show, and author of “Retire Before Mom and Dad: The Simple Numbers Behind A Lifetime of Financial Freedom”. He founded Doughroller.net in 2007, a popular personal finance blog that attracted millions of visitors. With a background as a litigation attorney, Rob is now a prominent voice in retirement planning, providing valuable education through his YouTube channel and other platforms.
If you’re looking for quality retirement finance tips, no matter where you are on your journey, this is a great episode for you!
Key Takeaways:
• Preparing for retirement allows you to enjoy the journey and the destination (just like hiking!).
• Learn about key aspects of retirement planning, such as investment strategy, withdrawal plans, and tax considerations, and the need for comprehensive preparation.
• What is the “Retirement Income Death Spiral”? And how can we avoid it?
• How does inflation and stock market conditions really affect your retirement savings?
• How to take a conservative approach to Social Security and still have cautious optimism about the future.
• Why you should not focus on individual stocks when planning for retirement!
Key Timestamps:
(02:10) Jesse’s Monologue: Retirement Planning Fundamentals
(05:47) John and Eva's Retirement Scenario
(13:09) Interview with Rob Berger
(14:00) Understanding the Retirement Income Death Spiral
(15:55) Inflation and Retirement Planning
(23:40) Social Security Concerns and Assumptions
(25:48) The Future of Social Security and Political Solutions
(27:24) The Importance of Diversified Income in Retirement
(29:26) The Role of Cash and Bonds in Retirement Portfolios
(34:21) The Emotional Side of Market Volatility
(39:26) Common Financial Mistakes and How to Avoid Them
Key Topics Discussed:
The Best Interest, Jesse Cramer, Rochester New York, financial planner, financial advisor, wealth management, retirement planning, tax planning, personal finance, Rob Berger, Retire Before Mom and Dad, Social Security, retirement account mistakes
Mentions:
Website: https://robberger.com/
YouTube: https://www.youtube.com/@rob_berger
LinkedIn: https://www.linkedin.com/in/bergerra/
Mentions:
https://bestinterest.blog/reaching-the-summit-retirement/
Retire Before Mom and Dad: The Simple Numbers Behind A Lifetime of Financial Freedom
How Much Cash Should You Hold In Retirement?
Should Cash Replace Bonds in a Portfolio?
How to Avoid the Retirement Income Death Spiral?
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.