No Diversification = Deep Trouble?! | AMA #3 with Jesse - E90
Personal Finance for Long-Term Investors - The Best Interest
Release Date: 09/25/2024
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...
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Do Long-Term Investors *Need* to Invest in Real Estate? | Chad “Coach” Carson - E101
Personal Finance for Long-Term Investors - The Best Interest
Jesse is joined by Chad Carson, who discusses residential real estate investing as a stable alternative to stocks and bonds. While real estate offers advantages like rental income, property appreciation, and tax benefits, Jesse also highlights challenges such as high costs, tenant issues, liquidity problems, and the time commitment required. Jesse thinks of his Rochester wealth management clients, and what some of them do. Chad emphasizes choosing the right location, focusing on properties with minimal renovation needs, and securing financing that ensures a healthy cash flow. He advises...
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Favorite Moments, Shoutouts, and a Name Change?! …From Our First 100 Episodes - E100
Personal Finance for Long-Term Investors - The Best Interest
Episode 100 of The Best Interest Podcast! This is a celebratory and reflective milestone featuring guest shout-outs, listener-favorite clips, and a discussion on the show's evolution. Jesse shares the podcast's origins, his journey from aerospace engineering to financial planning, and how the podcast nearly faded before finding renewed purpose in 2023. Throughout the episode, Joe Saul Sehy, Brian Feroldi, Paula Pant and other past guests are featured, shouting out The Best Interest and their own work, you’ll certainly want to check out. To celebrate, listeners wrote in with some of...
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Will They Claw Back My Tax Breaks? Should I “Buy, Borrow, and Die?” And More - AMA #5 - E99
Personal Finance for Long-Term Investors - The Best Interest
Time for another AMA with Jesse! First, Randy asks what it means to be rich, leading to an interesting evaluation of personal values, goals, and circumstances. Jesse explores relativity, “keeping up with the Joneses”, and what it means to have “enough”. Then, Bob asks about the potential tax burdens on beneficiaries and heirs, and Tom wonders whether some tax savings are worth the effort of logistical complexity. The fourth question comes from regular listener, Yogi, asking about the role of bonds in diversifying a portfolio. Jesse gets into the details of which bonds are which, which...
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What Do You Mean By “little p purpose”?! | Jordan Grumet - E98
Personal Finance for Long-Term Investors - The Best Interest
Jordan Grumet, AKA Doc G, returns to the podcast to share the difference between “Big P Purpose” and “little p purpose” and why you should pursue the seemingly less significant latter. Bringing together his experience in hospice care and finance, Jordan shines light on how we can create our purpose through personal growth and the pursuit of passions, rather than grandiose goals. Jordan calls these activities that bring joy "purpose anchors," which can be discovered through reflection and exploration. By engaging in these meaningful pursuits, individuals create positive ripple effects,...
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The Bad “Money Scripts” Someone Else Wrote for You | Brad Klontz - E97
Personal Finance for Long-Term Investors - The Best Interest
Jesse kicks today’s show off with a monologue on the importance of having the right temperament for investing - it’s not really about intelligence at all. Emotional stability and disciplined decision making outweigh expertise and intelligence when investing. The Dunning-Kruger effect and the paradox of choice are also highlighted, emphasizing the need to prioritize action over perfection in personal finance. For the second half of the show, Dr. Brad Klontz, Co-Founder of the Financial Psychology Institute and author of Start Thinking Rich, joins to discuss “money scripts”, which are...
info_outlineBack 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 family longevity, Lynn’s making some reconsiderations. Key considerations for anyone approaching Social Security include health, family history, need for benefits, ongoing work plans, spousal benefits, and how Social Security fits into their broader financial plan.
Yogi is considering his company's Employee Stock Purchase Plan (ESPP), which offers a 5% discount but no look-back provision. While it may seem like "free money," he's concerned about missing other investment opportunities. Key factors include market risk, taxes, and the risk of holding too much company stock.
Jacob and his wife, both 32, have diversified investments across various accounts, including sector-specific funds and broader options like S&P 500 and international funds. Jesse dives into ideas on how to diversify investments into a variety of asset classes, sectors, and geographies.
Maple Leaf is turning 65 and plans to apply for Medicare, asking whether the income lookback period for IRMAA (Income-Related Monthly Adjustment Amount) is a one-time event or reviewed annually. The lookback period is annual, with a two-year delay, meaning income from two years prior determines the surcharge.
Jimbo from Alabama asks whether the fiduciary standard is a sufficient filter when choosing financial advisors. While being a fiduciary is important, as it requires advisors to act in their clients' best interests, it’s a "coarse filter," and clients should dig deeper by asking about advisors' payment structures, investment philosophies, and potential conflicts of interest.
Our last question comes from Eric. Eric, 38, plans to retire at 55 while his wife intends to work until 65, raising the challenge of coordinating their financial and lifestyle transitions. Jesse emphasizes the importance of clear communication about how their daily routines and relationship dynamics might change as one partner retires while the other continues working
If you’d like a question in a future AMA, send Jesse a message!
Key Takeaways:
• When you want to take out Social Security depends greatly on your health (current and anticipated), personal needs, work plans, spousal benefits, and more.
• How do ESPPs work? And how can you make the most of these employee offers?
• How to diversify your investments into a variety of asset classes, sectors, and geographies.
• What is IRMAA? And how can you make the most of it?
• Just like when you look for a doctor, a therapist, or any other professional help, you’ll want to ask a series of questions to find out how they work and if it’s a good fit.
• How to balance your retirement plans with your spouse’s.
Key Timestamps:
(00:00) - Introduction and Featured Review
(01:47) - Family History and Social Security
(12:54) - ESPPs and Taxes
(21:21) - Investment Diversification
(29:06) - IRMAA and Lookback Periods
(37:41) - Questions to Ask Potential Advisors
(45:57) - Lifestyle Transitions to Retirement
Key Topics Discussed:
The Best Interest, Jesse Cramer, Rochester New York, financial planner, financial advisor, wealth management, retirement planning, tax planning, personal finance, IRMAA, ESPP, Income-Related Monthly Adjustment Amount, Employee Stock Purchase Plan, ask me anything, early retirement, capital gains tax
More of The Best Interest:
Check out the Best Interest Blog at bestinterest.blog
When Should I Take Social Security?: https://bestinterest.blog/when-should-i-take-social-security/
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.