But is NOW the Right Time to Invest in the Stock Market?! - E96
Personal Finance for Long-Term Investors - The Best Interest
Release Date: 12/18/2024
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_outlineTalking 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 find the needle. Speculative stock-picking is like picking out some straw and hoping it’ll turn out to be the needle. To illustrate the benefits of consistent investing - rather than attempted market timing - Jesse tells the tale of Bad Timing Bill, Normal Nick, and Good Timing Gary. Bill and Gary both tried to time the market. This episode is packed with insight you’ll want to return to again and again.
Key Takeaways:
• Don’t look for the needle in the haystack. Buy the haystack. Most stock pickers stumble into success.
• There’s no such thing as skilled stock picking because we can never know the entire market.
• Just because a business is massive and visible, doesn’t mean it will forever make good decisions.
• How to sort out a fair price for something. A good burger isn’t worth 100 dollars!
• What are CAPE and PE ratios?
• The story of Bill, Nick, and Gary: Why you shouldn’t try to time the market.
Key Timestamps:
(00:00) The Best Interest Year in Review
(08:02) The Evergreen Question: Is Now the Right Time to Invest?
(11:58) The Case for Index Investing
(25:16) Understanding Market Efficiency
(29:13) The Starbucks Dilemma: Diversification vs. Concentration
(32:01) The Importance of Price
(32:39) Warren Buffett's Wisdom on Fair Prices
(33:37) The Risks of Overconcentration in a Single Stock
(34:14) Diversification and Risk Management
(35:36) The Concept of Timing the Market
(36:08) The CAPE Ratio Explained
(46:39) Dollar Cost Averaging vs. Lump Sum Investing
(51:27) The Complexity of Market Movements
Key Topics Discussed:
The Best Interest, Jesse Cramer, Rochester New York, financial planner, financial advisor, wealth management, retirement planning, tax planning, personal finance, stock picking, speculation, index funds, mutual funds, stock market, DIY investing
Mentions:
Wealth Creation in the U.S. Public Stock Markets 1926 to 2019 by Hendrik Bessembinder https://papers.ssrn.com/sol3/papers.cfm?abstract_id=3537838
The Needle in the Haystack: https://bestinterest.blog/the-needle-in-the-haystack/
Yes, You Can Beat the Market, But...: https://bestinterest.blog/yes-you-can-beat-the-market/
Good Company, Bad Stock: https://bestinterest.blog/good-company-bad-stock/
The CAPE Ratio vs. Future Returns: https://bestinterest.blog/cape-vs-future-returns/
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.