6 Experts Share Their "Worst" Spending Stories (E109)

6 Experts Share Their "Worst" Spending Stories (E109)

Author: Jesse Cramer June 18, 2025 Duration: 50:04

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 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.


Navigating the world of money can feel overwhelming, with a constant stream of conflicting tips and trendy, quick-fix schemes. Personal Finance for Long-Term Investors-The Best Interest cuts through that noise. Host Jesse Cramer brings a unique perspective to the conversation, transitioning from his background as an aerospace engineer to his work as a fiduciary financial advisor. This podcast is built on the principle that genuine wealth isn't built overnight through speculation, but through consistent, well-reasoned decisions made over decades. Each episode delves into the mechanics and mindset required for that journey, exploring topics like retirement planning, intelligent investing, and the behavioral aspects of managing money. You'll find discussions that go beyond surface-level advice, examining the "why" behind proven strategies and how to apply them to your own life. The tone is conversational and grounded, avoiding financial jargon in favor of clear explanations. It’s a resource for anyone tired of the hype and seeking a sustainable path forward. By focusing on evidence-based ideas and patient execution, this podcast aims to provide listeners with the tools and confidence to build a secure financial future on their own terms. Tune in for a thoughtful, long-term approach to personal finance that prioritizes your best interest.
Author: Language: English Episodes: 100

Personal Finance for Long-Term Investors
Podcast Episodes
Target Date Funds: More Flawed Than Advertised (E137) [not-audio_url] [/not-audio_url]

Duration: 44:05
Looking for a financial planner? → PlanWithJesse.com Jesse delivers a critical re-evaluation of target date funds—one of the most widely used "set-it-and-forget-it" retirement tools—arguing that while their simplicity is…
He Retired Early - Here's What No One Warned Him About (E136) [not-audio_url] [/not-audio_url]

Duration: 52:49
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 abo…
Why Trump Accounts Fall Short  (AMA, E135) [not-audio_url] [/not-audio_url]

Duration: 51:26
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 priori…
Are You in a "Goldilocks" Retirement Range? (E132, AMA) [not-audio_url] [/not-audio_url]

Duration: 54:51
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 begi…
Less Wealth, More Certainty: Why Annuities Are Rarely Worth It (E131) [not-audio_url] [/not-audio_url]

Duration: 53:03
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 reti…
Don't Let a Scary Economy Cause Bad Retirement Decisions (E130) [not-audio_url] [/not-audio_url]

Duration: 51:36
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 inves…
"Isn't My Portfolio the Same as My Financial Plan??"  (AMA, E129) [not-audio_url] [/not-audio_url]

Duration: 41:18
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 dismantli…
11 "Bad" Financial Moves...That Are Actually Fine (E128) [not-audio_url] [/not-audio_url]

Duration: 41:28
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 example…