6 Experts Share Their "Worst" Spending Stories (E109)
Personal Finance for Long-Term Investors
Release Date: 06/18/2025
He Retired Early - Here’s What No One Warned Him About (E136)
Personal Finance for Long-Term Investors
In today’s replay of episode 62, Jesse is joined by Fritz Gilbert—retirement blogger behind The Retirement Manifesto and former corporate executive turned early retiree—for a candid and experience-driven conversation about what retirement actually feels like after the spreadsheets are closed and the plan becomes real life. Fritz shares the story behind his early retirement decision, including the financial discipline, intentional lifestyle design, and tradeoffs that made it possible, but quickly moves beyond the numbers to focus on the psychological transition that catches many retirees...
info_outline
Why Trump Accounts Fall Short (AMA, E135)
Personal Finance for Long-Term Investors
On his 15th Ask Me Anything episode, Jesse tackles a fresh set of listener questions with a throughline that centers on how to evaluate financial decisions in a world full of new ideas, policy noise, and competing priorities—starting with a breakdown of “Trump accounts” and what they actually mean for real planning. Rather than reacting to the headline, he walks through how to analyze any new or proposed account type: understanding its tax treatment, limitations, and—most importantly—where it fits (or doesn’t) within an already well-structured plan built around flexibility and...
info_outline
Even Financial Advisors Misunderstand Monte Carlo Retirement Analysis (E134)
Personal Finance for Long-Term Investors
In this technical deep dive, Jesse pulls back the curtain on one of the most commonly cited tools in retirement planning—Monte Carlo analysis—explaining what it actually does, how it works under the hood, and why its outputs are often misunderstood. He begins by contrasting Monte Carlo simulations with simpler “static” retirement calculators and deterministic cash-flow projections, showing why modeling thousands of randomized market paths provides a more realistic stress test of retirement outcomes. From there, Jesse walks through the mechanics of Monte Carlo itself—from the concept...
info_outline
Uncomfortable Truth: Great Investing Decisions Can Look Wrong For Years (E133)
Personal Finance for Long-Term Investors
Jesse is joined by Rubin Miller—former Dimensional Fund Advisors insider, founder and CIO of Peltoma Capital Partners, author of the Fortunes and Frictions blog, and national chess master—for a wide-ranging conversation about how investment philosophy, behavioral discipline, and real-world client psychology intersect. Rubin pulls back the curtain on how factor tilts like small-cap, value, and profitability work. The discussion moves beyond theory into practice, tackling commoditization in passive investing, the tradeoffs between index funds and structured tilts, and the uncomfortable truth...
info_outline
Are You in a "Goldilocks" Retirement Range? (E132, AMA)
Personal Finance for Long-Term Investors
On his 14th Ask Me Anything episode, Jesse tackles a set of listener questions that expose the messy, real-world edges of financial planning—where tax rules, behavioral tendencies, and long-term strategy collide. He begins by unpacking a nuanced withdrawal-order debate, explaining why the “optimal” sequence between taxable, tax-deferred, and Roth accounts depends less on rigid rules and more on tax brackets, future income expectations, and optionality over time. From there, he walks through a detailed case involving concentrated stock risk and diversification timing, illustrating how...
info_outline
Less Wealth, More Certainty: Why Annuities Are Rarely Worth It (E131)
Personal Finance for Long-Term Investors
In this expansive and deliberately contrarian episode, Jesse takes on annuities—not with a sales pitch or a blanket dismissal, but by putting them under a rigorous planning lens rooted in risk, probability, and real retirement outcomes. He begins by laying out what annuities actually are, clearly separating fixed annuities from their variable cousins, and explaining why high fees, capped upside, illiquidity, and poor expected returns make most annuity products deeply unattractive. From there, Jesse zeroes in on the one annuity type he considers intellectually defensible in narrow...
info_outline
Don't Let a Scary Economy Cause Bad Retirement Decisions (E130)
Personal Finance for Long-Term Investors
Jesse is joined by Cullen Roche—financial writer, macro thinker, and founder of Discipline Funds—for a clear-eyed conversation about how money actually works, why so much financial commentary gets it wrong, and how investors can make better decisions by understanding the plumbing beneath markets. Together, they unpack the core mechanics of the modern monetary system, including how government spending, deficits, and interest rates function in practice rather than theory, and why fears around debt and inflation are often oversimplified or misapplied. Cullen explains the crucial distinction...
info_outline
"Isn't My Portfolio the Same as My Financial Plan??" (AMA, E129)
Personal Finance for Long-Term Investors
On Jesse’s 13th AMA episode, he steps back from tactics and returns to first principles, answering listener questions that cut to the core of what financial planning actually is—and what it is not. He begins by dismantling the common assumption that a portfolio and a financial plan are interchangeable, explaining why investing is only one component of a much broader process that aligns cash flow, risk, taxes, goals, and life transitions across decades. From there, Jesse walks listeners through his end-to-end financial planning framework, starting with values and goal clarification, moving...
info_outline
11 "Bad" Financial Moves...That Are Actually Fine (E128)
Personal Finance for Long-Term Investors
In this candid solo episode, Jesse walks through a series of financial decisions that look “wrong” on paper but make complete sense when viewed through the lens of real life, values, and tradeoffs. Using personal examples, he challenges the idea that optimal spreadsheets should always dictate behavior, arguing instead that financial planning exists to support a life well lived—not to win theoretical efficiency contests. Jesse explains why holding excess cash even when expected returns favor investing, and prioritizing flexibility and simplicity over marginal tax optimization. Throughout...
info_outline
"The Most Important Number" in Your Retirement?! (E127)
Personal Finance for Long-Term Investors
Jesse is joined by Jeremy Keil—Certified Financial Planner, Chartered Financial Analyst, author of Retire Today, and host of the Retirement Revealed podcast—for a wide-ranging conversation that reframes how people should think about retirement decisions long before and long after the final day of work. Together, they explore why most people retire earlier than planned, why longevity is so often misunderstood, and how flawed assumptions about life expectancy, Social Security, and taxes can quietly undermine otherwise solid plans. Jeremy introduces the concept of “retirement longevity”...
info_outlineJesse 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 money habits persisting despite sudden wealth. Doc G and Joe Saul-Sehy add their unique perspectives on personal finance and the emotional relationship with money. Together, they unpack how financial decisions shape our lives, the importance of aligning spending with values, and the lessons learned from both scrimping and splurging.
Key Takeaways:
• Financial freedom doesn’t always come with a clear sense of how to enjoy money meaningfully.
• Renting luxury experiences can be more satisfying and economical than owning them.
• Time, health, and family often become more valuable than money as people grow older.
• Community and shared experiences often bring more satisfaction than expensive possessions. Lifestyle upgrades need to be aligned with personal values to feel meaningful.
• Former spendthrifts can struggle just as much with letting go of financial vigilance.
• Understanding your money story is key to shifting your habits and mindset with intention. Even the financially savvy can be blindsided by lifestyle creep and emotional spending.
Key Timestamps:
(00:00) – Scar Tissue: Financial Lessons from the Past
(13:59) – The Mini Bar Mishap
(20:11) – The $500 Parking Ticket
(23:56) – Balancing Financial Optimization and Enjoying Life
(24:29) – Time vs. Money: Changing Priorities
(25:50) – Keeping Up with the Joneses: A Personal Story
(30:59) – The Perils of Consumerism and Stealth Wealth
(44:12) – Rent Your Luxury and Buy Utility
(45:20) – Frugality Habits: From Broke to Millionaire
Key Topics Discussed:
The Best Interest, Jesse Cramer, Wealth Management Rochester NY, Financial Planning for Families, Fiduciary Financial Advisor, Comprehensive Financial Planning, Retirement Planning Advice, Tax-Efficient Investing, Risk Management for Investors, Generational Wealth Transfer Planning, Financial Strategies for High Earners, Personal Finance for Entrepreneurs, Behavioral Finance Insights, Asset Allocation Strategies, Advanced Estate Planning Techniques
Bill Yount:
Website: https://catchinguptofi.com/
LinkedIn: https://www.linkedin.com/in/bill-yount-a8033036/
Diania Merriam:
Website: https://economeconference.com/about/
LinkedIn: https://www.linkedin.com/in/dianiamerriam/
Justin Peters:
Website: https://podcasts.apple.com/us/podcast/fi-minded-achieve-financial-independence-have-fun-doing-it/id1496701179
LinkedIn: https://www.linkedin.com/in/justinleepeters/
Jordan (Doc G) Grumet:
Website: https://jordangrumet.com/
LinkedIn: https://www.linkedin.com/in/jordan-grumet-38a506179/
Joe Saul-Sehy:
Website: https://www.stackingbenjamins.com/
LinkedIn: https://www.linkedin.com/in/joe-saul-sehy-b3426b31/
Jeremy Schneider:
Website: https://www.personalfinanceclub.com/
LinkedIn: https://www.linkedin.com/in/jerschneid/
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 education and entertainment. It should not be taken as financial advice, and is not prescriptive of your financial situation.