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:

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:

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:

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:

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:

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:

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:

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:

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:

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: