Thoughts On Money [TOM]

Hosted by Trevor Cummings

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275

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Jun 2026

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About the show

THOUGHTS ON MONEY [TOM] is a podcast looking at simple truths on money. Everything from budgeting to investing to decision making. A great place to come for answers to your personal financial questions or to spark thought on how to improve your financial life.

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June 12, 202641 min

Food for Thought - The Economics of Eating

This week's blogpost - https://bahnsen.co/3RTyKah Trevor Cummings hosts the Thoughts on Money (TOM) podcast with Brett Bonecutter and Blaine Carver to discuss Brett’s article on food and its economic and cultural implications. They explore how nearly any topic connects to money, then reflect on family dinners, modern home layouts, and how convenience and abundance may reduce intentional time together. Brett shares “food dollar collapse” data: food fell from nearly 50% of household budgets in the early 1900s to 9.7% in 2025, while spending has flipped from mostly groceries to mostly eating out/convenience, and time in the kitchen dropped from six hours per day to about 45 minutes. They discuss trade-offs like lowered appreciation, snacking, delivery markups, loss of cooking skills, and “options overload” in stores with 32,000 items, plus a brief MAHA-related comparison of past low medical spending versus today’s higher costs. 00:00 Welcome to TOM 00:14 Why Talk About Food 02:15 Dinner Table Culture 06:30 Food Memories and Nostalgia 09:46 Food Dollar Collapse 15:29 Abundance Trade Offs 20:12 Convenience and Eating Out 22:04 Convenience And Doomscrolling 23:50 Cooking As Joy And Budget 26:55 Learning Kitchen Skills 28:36 Generations And Eating Out 30:42 MAHA Food And Healthcare 33:09 Pop Tarts And Choice Overload 36:09 Tradeoffs Gratitude And Wrap Links mentioned in this episode: http://thoughtsonmoney.com http://thebahnsengroup.com

June 5, 202648 min

A Financial Planning Superpower

This week's blogpost - https://bahnsen.co/4voyr5t Trevor Cummings and Brett Bonecutter discuss superheroes as a metaphor for investing, contrasting “superhuman” finance promises that are often too good to be true with the practical “Batman” approach of using tactical discipline. Trevor argues that earmarking—assigning a clear purpose and time horizon to every dollar—is a personal finance superpower that guides account selection, tax strategy (e.g., using a 529 for college savings), liquidity needs, and asset allocation, and helps avoid being over-allocated to either stocks for near-term needs or cash for long-term goals. They explore why common allocations like 60/40 exist, how disconnected investors can be from the purpose of their portfolios, how estate planning naturally forces earmarking, and why some clients with projected surpluses may benefit from gifting during their lifetime, while warning that earmarking can be overdone in retail banking-style account proliferation. 00:00 Welcome 00:34 Superhero Fandom Stories 02:32 Favorite Powers and Old Movies 04:37 Batman vs Superman Finance 07:09 Earmarking Explained 10:45 Purpose Before Investing 14:12 Portfolio Theory vs Reality 15:22 Why 60 40 Exists 20:34 Popcorn Portfolio Metaphor 22:42 Big Expense Earmarks 25:34 Vacations Versus Budget 26:35 Legacy And Estate Goals 29:40 Gifting While Alive 32:14 4 Percent Rule Surplus 34:01 Overearmarking Cautionary Tale 36:47 Envelope Method Explained 41:31 All Money Has Purpose 43:29 Cash Heavy Portfolios 45:55 Conclusion Links mentioned in this episode: http://thoughtsonmoney.com http://thebahnsengroup.com

May 28, 202638 min

35,000 Feet & The Things That Matter

This week's blogpost - https://bahnsen.co/4eayQTh Today, Matthew Gregory writes the Thoughts on Money article, and discusses with Trevor about how to reframe estate planning from something morbid into an act of love that protects the people you care about by reducing logistical and legal burdens during grief. Using The Princess Bride’s “prepare to die” line and analogies like board games and omakase, they emphasize starting with basics (wills, trusts, medical directives, powers of attorney, guardianship) before complex strategies, and ensuring plans are stored and understood (even via one-page flowcharts). They note estate planning applies at all ages, including young adults facing HIPAA limits, and can be revisited as life and laws change. Trevor argues estate planning often ranks ahead of investment strategy, and they close by suggesting viewers consider whether planned end-of-life gifts (to family or charity) might be better made during life for qualitative and potential tax benefits. 00:00 Intro 00:49 Estate Planning as Love 03:50 "Prepare to Die" Moment 05:41 Executor Lessons and Family First 08:34 Start Simple, Not Complex 11:38 Settler's of Catan Strategy 16:39 Guided Advice, Omakase Style 19:59 Estate Planning Before Investing 25:47 All Ages and Family Transparency 27:52 Avoid Overengineering the Plan 32:45 Lean Into Discomfort 33:48 Give While Living 35:57 Wrap Up and Conclusions Links mentioned in this episode: http://thoughtsonmoney.com http://thebahnsengroup.com

May 22, 202649 min

The Jetsons vs. The Terminator - The Two Visions of Artificial Intelligence

This week's blogpost - https://bahnsen.co/3PFBC9R With Trevor Cummings out, host Blaine Carver talks with author Brett Bonecutter about artificial intelligence through the competing visions of a utopian “Jetsons” future versus a dystopian “Terminator” outcome. They discuss how AI may be overhyped in the short run but underestimated over the long run, define AI as pattern-recognition systems that amplify human creativity and error, and address concerns about sentience, hacking, and misuse. Brett contrasts materialist and spiritual views of what it means to be human, arguing AI will mirror human nature and produce both major benefits (like medical breakthroughs) and serious harms. They cover job disruption, emphasizing roles involving “emotional friction,” and investing implications, noting most diversified investors already have significant AI exposure and that picking winners may include losers. 00:00 Trevor Is Out Today 00:52 AI Hype And FOMO 03:35 Dotcom Lessons For AI 07:18 Disruption And Destruction 10:28 Utopia Vs Dystopia 13:07 Defining Artificial Intelligence 18:25 Singularity And AI Risks 22:40 What It Means To Be Human 24:54 Materialism Meets AI 26:49 AI as New Species 27:27 Imago Dei Framework 31:39 Purpose to Transform 32:28 AI Mirrors Humanity 34:08 Jetsons vs Terminator 34:55 Jobs and Emotional Friction 39:17 Kitchen Table Work 41:49 Investing Without FOMO 44:35 Culture Shapes AI 46:59 Wrap Up and Disclosures Links mentioned in this episode: http://thoughtsonmoney.com http://thebahnsengroup.com

May 15, 202658 min

Financial Framework for Graduates

This week's blogpost - https://bahnsen.co/4nx56TO Trevor Cummings hosts the Thoughts on Money podcast with Blaine Carver and Brett Bonecutter to discuss Blaine’s blog “Financial Framework for Graduates”) and the challenges of “launching” into adulthood amid high costs of living and shifting cultural expectations. They debate when and how young adults should become independent, including the “boomerang” move back home, and stress building responsibility through paying bills, doing taxes, and maintaining an emergency fund, while balancing parental support without “handicapping” kids. Blaine outlines key principles: learn to say no to social-pressure spending, focus on fundamentals (spending tracking, pay stubs, credit scores, benefits, time value of money), prioritize liquidity in your 20s, avoid social-media financial advice, begin giving at any level, and seek wise counsel. They invite TBG clients’ children to meet with their advisors. 00:00 Podcast Introductions 00:41 Graduation Season Vibes 02:25 Maycember And Milestones 04:21 Credit Card Cutoff Story 08:43 Launch And Responsibility 11:17 Boomerang Kids Debate 14:17 Subsidies And Tough Love 20:27 Affordability Vs Expectations 23:44 Parenting Adult Children 26:04 Culture Marriage And Money 28:04 Delayed Adulthood Trends 29:10 Water Bottle Lesson 30:48 Say No Pressure 32:29 Credit Cards Trap 34:01 Master Money Basics 37:35 Cash And Liquidity 41:24 Ignore Social Media Gurus 47:41 Start Giving Today 50:07 Seek Wise Mentors 54:46 Wrap Up And Next Steps Links mentioned in this episode: http://thoughtsonmoney.com http://thebahnsengroup.com

May 8, 202629 min

Not an Exact Science

This week's blogpost - https://bahnsen.co/48QRb50 Trevor Cummings and Brett Bonecutter discuss Trevor’s “Not an Exact Science” blog post, prompted by a prospective client who achieved strong decade-long returns largely because nearly half his portfolio was concentrated in two top-performing stocks, leading to a conversation about diversification and how investors often blur skill and luck. They explore overconfidence, FOMO, and the “exception not the rule” mindset that causes people to discount risk, emphasizing that risk cannot be eliminated and must be respected. Trevor explains Monte Carlo simulations, their usefulness for testing plan viability, and their limitations given unforeseeable life events. They reference Long-Term Capital Management and “When Genius Failed” as a caution about arrogance in modeling. The episode highlights managing mitigatable risks (insurance, emergency funds), avoiding unnecessary concentration, and building flexibility—“the power of the pivot”—through planning, liquidity, and long-term compounding. 00:00 Welcome to TOM 00:26 Client Concentration Shock 02:17 Skill Versus Luck 04:59 Risk Always Exists 06:44 Exception Not Rule 09:00 Monte Carlo Reality Check 11:28 When Genius Failed 15:45 Mitigate What You Can 20:14 Power of the Pivot 23:11 Advice for Catching Up 26:52 Back to the Basics 27:29 Wrap Up and Contact Links mentioned in this episode: http://thoughtsonmoney.com http://thebahnsengroup.com

May 1, 202645 min

Ten-Dollar Finance Words

This week's blogpost - https://bahnsen.co/4tJyhFD Trevor Cummings hosts a “Thoughts on Money” podcast episode with Blaine Carver and Brett Bonecutter, discussing Brett’s lighthearted blog post “$10 Finance Words” and how financial jargon can confuse or impress audiences. They contrast unavoidable shorthand with performative buzzwords, share pet peeves (like “curated,” “circle back,” and “HBD”), and emphasize knowing your audience and translating terms for clients. Brett explains meanings and pitfalls of terms such as EBITDA (including WeWork’s “community adjusted EBITDA”), fungible vs. non-fungible, and deal jargon like cap stack, mezzanine financing, and waterfalls, plus corporate euphemisms like “right-sizing” and the sometimes-deceptive use of “leverage.” They close with jokes about pop-culture references, slang, and invite listener emails and podcast ratings. 00:00 Welcome And Setup 01:26 Why Finance Jargon 06:39 Words And Pet Peeves 10:25 EBITDA Explained 17:30 Snooty Language Signals 18:34 Gray Poupon Reference 20:16 Fungible And NFTs 23:22 Capital Stack Basics 26:05 Euphemisms That Stick 26:26 Right Sizing Explained 27:17 Idioms Across Cultures 28:43 Leverage Versus Debt 31:29 Leverage In Real Markets 33:01 BDCs And Private Credit 35:15 Optionality Word Nerds 36:32 Cosplay And Meme Slang 38:49 Pop Culture Blind Spots 41:47 Closing Thoughts And Feedback Links mentioned in this episode: http://thoughtsonmoney.com http://thebahnsengroup.com

April 24, 202648 min

The Next Bear Market

This week's blogpost - https://bahnsen.co/42ccBWB In this week's Thoughts on Money, Trevor, Blaine, and Brett discuss Blaine's article, “The Next Bear Market,” which argues that a 20% market decline will happen at some point and that recent, fast recoveries (COVID, 2022, 2023 bank failures, and a short-lived 2025 ~19% drawdown) may be breeding investor complacency. They distinguish corrections (10%) from bear markets (20%), highlight how intra-year drawdowns often fade in annual returns, and emphasize the market’s interconnected participants, leverage-driven selling, and the expectation that the Fed will intervene. The group focuses on preparing through adequate liquidity and safety nets to avoid selling at the wrong time, understanding why you own assets, and emphasizing dividends and income as part of total return. They note risk surveys can misstate real behavior, advisors act as guides to help clients endure volatility, and premium returns require accepting volatility as the price of admission. 00:00 Podcast Intro 00:30 Why Bear Markets Happen 03:05 Drawdowns vs Annual Returns 05:02 Statement Pain Explained 07:19 Too Big to Fail Mindset 10:17 Complacency After Long Runs 18:40 Corrections vs Bear Markets 20:37 Risk Tolerance Reality Check 23:04 Long Horizon Portfolio Buckets 24:15 Focus on Dividends Not Price 25:47 Dividends And Total Return 26:22 Safety Nets And Inflation 27:31 Bear Markets And Labels 28:57 Recession Versus Bear 29:37 Markets Versus Economy 30:40 Why Cash Reserves Matter 32:51 Leverage And Forced Selling 34:24 Liquidity And Buyer Shortages 35:24 Life Transitions And Risk 37:00 Advisor Psychology And Coaching 40:38 Guides Expand Risk Tolerance 41:42 Portfolio Rules Of Thumb 43:38 Volatility Price Of Returns 45:32 Time Horizon Is The Edge 46:35 Wrap Up And Disclosures Links mentioned in this episode: http://thoughtsonmoney.com http://thebahnsengroup.com

April 17, 202641 min

If You Could Ask Just One Question

This week's blogpost - https://bahnsen.co/4mUGiFb Trevor Cummings hosts the Thoughts On Money podcast with Brett Bonecutter to discuss a due diligence hypothetical: if you could ask an advisor or investment manager only one question, it should be “How do you invest your money?” Drawing on Nassim Taleb’s “skin in the game” idea, Trevor argues behavior and portfolio holdings reveal true beliefs more than polished pitches. He recounts meeting a Twitter-famous fund manager whose personal investments didn’t match his fund strategy, reinforcing the “eat your own cooking” rule while noting it isn’t a complete substitute for full due diligence or diversification. The conversation explores aligned incentives versus fiduciary labels, Buffett’s Goldman Sachs deal requiring executives to retain shares (“buying the jockey”), 1929-era disclosure rules on insider trading, and Trevor’s real example of a near-retiree concentrated in two stocks despite claiming high confidence. 00:00 One Question Diligence 01:40 Skin In The Game 02:48 Quitting Social Media 05:31 Fund Manager Test 09:22 Eat Your Cooking 14:34 Buffett Deal Lesson 18:35 Limits Of Skin 19:56 Peace Child Setup 20:26 Judas and the Gospel 21:24 Peace Child Incentives 22:21 Advisor Skin in Game 23:42 Fiduciary vs Incentives 25:09 Taleb Fund Cycle 28:35 Do You Follow Advice 31:41 1929 Insider Reporting 35:06 Eating Own Cooking 35:39 Diversification Wake Up 38:04 Due Diligence Wrap Links mentioned in this episode: http://thoughtsonmoney.com http://thebahnsengroup.com

April 10, 202646 min

Room for Life

This week's blogpost - https://bahnsen.co/4sIiJ3H On the Thoughts On Money Podcast, hosts Blaine Carver and Brett Bone Cutter talk with Director of Financial Planning Matt Gregory about his article “Room for Life,” inspired by running in New York City and Morgan Housel’s The Psychology of Money. Gregory explains the need to balance detailed modeling with the reality of uncertainty, using conservative assumptions (often planning to age 100) to create flexibility so plans can absorb pivots without falling apart. He shares his personal pivots from musical theater at NYU into finance, emphasizing that planning is both technical and relational storytelling. The discussion covers helping both technical and narrative-minded clients, avoiding “Armageddon” planning while building margin, using scenario ranges to provide clarity, and viewing the financial plan as a launchpad for tax, savings, and other decisions. They also stress estate planning as completing the picture—aligning assets with family and charitable goals and updating plans as life changes. 00:00 Podcast Welcome 00:37 Room for Life Origins 03:12 Matt’s Career Pivot 06:06 Storytelling in Planning 08:40 Different Client Mindsets 10:01 Room for Life Reframed 11:42 Expect the Unexpected 13:36 Optimism vs Pessimism 15:36 Three Scenario Planning 17:14 Clarity and Client Questions 19:29 Puzzle Framework for Plans 21:23 When Clients Resist Planning 22:32 Plans Spark Motivation 23:01 Planning Launchpad Topics 24:24 Fixing Fragile Plans 26:39 Budgeting Styles That Fit 28:05 False Precision Reality 30:30 Golf Shot Planning Analogy 31:47 Estate Planning Completes Plan 35:34 Evolving Estate Plans 39:05 Mortgage Planning Perspective 40:48 Advice Over Transactions 42:46 Final Takeaways Wrap Links mentioned in this episode: http://thoughtsonmoney.com http://thebahnsengroup.com