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
Release Date: 01/29/2025
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...
info_outline
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...
info_outline
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...
info_outline
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...
info_outline
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...
info_outline
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...
info_outline
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....
info_outline
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...
info_outline
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...
info_outline
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_outlineTime 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 financial goals they’re good for, and when you should consider other options. To wrap up the show, Hector asks about the “buy, borrow, die” strategy employed by the ultra-wealthy: buy appreciating assets, borrow against them for liquidity without selling, and pass them to heirs with a stepped-up cost basis, avoiding capital gains taxes.
If you’d like a question in a future AMA, send Jesse a message!
Tune in next week for the 100th episode celebration!
Key Takeaways:
• Wealth varies based on individual values and circumstances. It’s less about achieving a specific number and more about feeling secure and content with your resources.
• The tax burden of inherited IRAs is based on the beneficiary's income and tax bracket, which can differ significantly from the original contributor's tax savings.
• Decisions like Roth conversions depend on whether the potential tax savings justify the added effort and complexity for an individual.
• Bonds provide stability and dependability for short-term goals. Short-duration, high-quality bonds like U.S. Treasuries are less sensitive to interest rate changes and offer more reliability.
• While effective for minimizing taxes, the “buy, borrow, die” strategy involves risks such as margin calls, regulatory changes, and the cumulative cost of loan interest potentially outweighing benefits.
• Wealth strategies should focus on understanding and minimizing tax liabilities without excessive risk, avoiding overly aggressive tax avoidance tactics.
Key Timestamps:
(02:17) Question 1: What Does It Mean to Be Rich?
(09:11) Question 2: Concerns About 529 College Savings Plans
(16:57) Question 3: Roth Conversions and Tax Savings
(23:50) Question 4: Evaluating Bond Performance and Diversification
(31:23) Question 5: The Buy, Borrow, Die Strategy
Key Topics Discussed:
The Best Interest, Jesse Cramer, Rochester New York, financial planner, financial advisor, wealth management, retirement planning, tax planning, personal finance, buy borrow die, Roth conversions, tax avoidance, inheritance, bonds, diversification, rich, five year rules
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.