Thoughts On Money [TOM]

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:

This week's blogpost - https://bahnsen.co/3PHCjiB

Host Trevor Cummings, with Brett Bonecutter and Blaine Carver, discusses whether Jesus’ teachings support socialism, prompted by Senator Raphael Warnock citing Matthew 25 in policy debates about poverty and healthcare. Brett argues socialism is often invoked as a moral claim and defines it as collective ownership and cooperative regulation to constrain private self-interest, then contends Jesus’ teachings and biblical law assume private and real property rights, voluntary exchange, merit-based reward, banking, and interest. They debate whether Jesus’ statements address individual heart posture versus prescribing systems, with Brett pointing to parables of landowners/tenants and the talents, and Jesus praising the widow’s offering, as incompatible with socialist ethics. The conversation emphasizes a “free and virtuous” society, personal responsibility and generosity as the Bible’s mechanism for caring for the poor, and invites listener feedback.

00:00 Welcome and premise

00:46 Holy Week motivation

01:32 Socialism in culture

02:36 Morality and Jesus

04:16 Why this matters

06:35 Warnock quote context

09:07 Defining socialism

11:00 Polls and capitalism label

13:19 Heart versus system

17:14 Parable property rights

20:04 Rich ruler nuance

22:29 Systemic assumptions

23:11 Systemic Lens Debate

24:16 Familiar Categories Not Endorsement

25:45 Parable of the Talents

29:50 Morality Envy and Greed

32:55 Acts Church and Coercion

35:54 Widows Mite and Charity

38:08 Was Jesus a Socialist

41:02 Too Big to Fail Tensions

43:41 Final Thoughts and Wrap

Links mentioned in this episode:

This week's blogpost - https://bahnsen.co/40YZ2Jj

Trevor Cummings hosts the Thoughts and Money Podcast with Brett and Blaine as they discuss Blaine’s article, “What Kind of Spending Makes Us Happy?” using stories about kids choosing purchases, trips to Disneyland and Chuck E. Cheese, and how adult spending often runs on autopilot amid frequent transactions and subscription costs. They contrast “happiness” with more lasting “joy,” describe how budgeting should start with the “why,” and note how recurring payments and social pressure can drive unexamined spending. Drawing on research and client observations, they highlight that giving (often producing a “warm glow”) and spending on experiences and relationships tend to bring more lasting satisfaction than material goods, while buying to impress others (the “man in the car” paradox) can disappoint. The episode ends with a call to reflect on what brings joy and align spending with personal values.

00:00 Podcast kickoff

00:28 Kids and money

01:38 Disney and Chuck E Cheese

02:51 Autopilot spending

03:58 Happiness versus joy

07:41 Budgeting with purpose

08:56 Subscription trap

12:21 Privilege and gratitude

14:16 Spending on experiences

18:11 What research shows

20:19 Joy of giving

22:34 Motives for Giving

23:02 Anonymous Giving Debate

24:42 Warm Glow Study

27:09 Giving as Money Habit

27:58 Spending on Experiences

30:33 Memory Dividends Mindset

32:19 Second Homes and Familiarity

35:22 Man in the Car Paradox

41:23 Hedonic Treadmill Trap

42:28 Align Spending with Values

44:24 Final Wrap and Call In

Links mentioned in this episode:

This week's blogpost - https://bahnsen.co/3PkPu91

Trevor Cummings hosts the Thoughts and Money podcast with Brett “Bone Cutter” and Blaine Carver to address recurring client fears about soaring U.S. national debt and whether “Debt-mageddon” is imminent. They clarify deficit vs. debt using a household analogy, explain how Treasury issuance funds deficits, and cite projected 2026 figures: ~$5.6T receipts vs. ~$7.4T spending, ~ $1.9T deficit, and over $1T of interest expense, with ~75% of spending mandatory. They note rates are historically low (mid-3% average vs. ~9.2% in 1986), meaning higher rates could bust the budget. Possible “solutions” (raise taxes, cut spending, grow out of it, lower rates) all have limits, so they expect a slow, Japanification-style grind rather than a sudden collapse. For investors, they caution against complacent indexing, long-duration bonds, crypto, and overreliance on gold, and emphasize durable, cash-flowing dividend-growth businesses and measuring opportunity cost.

00:00 Podcast Introductions

00:20 Debtmaggedon Setup

01:03 Apocalypse Pop Culture

03:41 Preppers And Planning

04:25 Five Key Questions

05:54 Deficit Versus Debt

07:47 How Government Borrows

11:42 Budget Math Reality

12:36 Interest Costs Squeeze

17:08 Debt Versus GDP Context

20:42 Is It Solvable

20:49 Raise Taxes Tradeoffs

23:18 Cut Spending Politics

23:51 Can We Grow Out

24:24 Can Government Cut Rates

25:51 Why Long Rates Are Market Set

26:44 No Magic Wand Fixes

27:34 Bell Curve Future Scenarios

29:23 Middle Path Japanification

30:23 Prepper Mindset And Paralysis

33:39 Markets Signal No Debt Bomb

34:55 Investor Playbook Starts Here

35:21 Beware Indexing And Bonds

39:33 Opportunity Cost Of Cash

43:05 Crypto And Gold Skepticism

45:30 Dividend Growth And Real Profits

47:58 Closing Jokes And Recap

Links mentioned in this episode:

This week's blogpost - https://bahnsen.co/4bFGcwT

Trevor Cummings hosts The Thoughts on Money Podcast with Brett Bonecutter and Blaine Carver to discuss “convictions over conformity,” arguing that shallow convictions lead investors to chase hot trends and abandon strategies when results turn. They contrast conformity/coercion with conviction by comparing Prohibition (a short-lived, legally forced attempt to curb alcoholism) with Alcoholics Anonymous (a long-lasting program rooted in personal responsibility and shared beliefs). The group emphasizes understanding the “why” behind an investment philosophy to avoid short-term decision-making, noting clients who engage intellectually are calmer during market stress. They discuss how strong convictions help filter product pitches and evaluate risk versus tax benefits. Trevor also shares uncertainty around legacy/estate planning, stressing communication, avoiding formulaic planning, and recognizing multi-generational impacts of wealth transfer.

00:00 Welcome and Setup

00:50 Why Conviction Matters

01:40 Conviction vs Conformity

03:54 Clients and Market Volatility

07:55 Prohibition as a Case Study

13:00 AA and Personal Responsibility

16:36 Start With Why

17:35 Staying True to Philosophy

20:24 Convictions Rooted in Truth

20:57 Grandma's Ham Parable

21:16 Ham Ends Parable

22:18 Why Beats What

23:34 AI Advice Pitfalls

24:28 Legacy Planning Uncertainty

27:05 Communication And Expectations

31:37 Advisor Role Boundaries

37:12 Gifting While Alive

38:44 Generational Ripple Effects

42:08 Fully Convinced Wrap Up

43:07 Ratings And Next Steps

Links mentioned in this episode:

This week's blogpost - https://bahnsen.co/47grFFj

Trevor Cummings hosts the Thoughts and Money Podcast with Brett Bonecutter and Blaine Carver, discussing his blog topic “Shortcuts, Head Starts and Changing Lanes.” After attending a conference job fair for aspiring financial advisors, they critique “fast track” career programs and argue against career and investing shortcuts, emphasizing foundation-building, patience, and willingness to do early “dirty work.” They compare shortcuts to chasing penny stocks, leverage, and persuasive pitches, noting investors’ susceptibility to FOMO, media narratives, and relative performance envy. They advocate “head starts” through early saving and compounding, citing a chart showing higher ending wealth from starting at 25 versus 35 despite lower total contributions. They warn against “changing lanes” in strategies, promote seeking “good returns, not best returns,” and stress having a durable investment philosophy, accountability, and discipline to avoid ruining long-built progress quickly.

00:00 Welcome and Banter

00:54 Conference Shortcut Pitch

02:24 Why the Long Cut Wins

05:44 Dirty Work and Foundations

08:08 Shortcuts in Life and Money

10:05 Smooth Is Fast Principle

12:01 Penny Stocks and Red Flags

13:56 Why We Chase Shortcuts

18:08 Head Starts Beat Catching Up

20:05 Compounding Chart Explained

21:26 Discipline and Real Life Costs

24:08 Don’t Disrupt Compounding

24:40 Can You Afford It

26:18 Credit Changes Everything

27:42 Changing Lanes Trap

29:36 Good Returns Mindset

31:30 Relative Returns FOMO

33:21 Shallow Convictions

34:31 Philosophy vs Institutions

39:49 Time Horizon Edge

42:34 Reputation and Shortcuts

43:54 Advisor as Accountability

45:13 Same as Ever Lessons

46:06 Overconfidence and Wrap Up

Links mentioned in this episode:

This week's blogpost - https://bahnsen.co/4rAtQvD

Trevor Cummings, hosting with a lost voice, interviews blog author Brett Bonecutter about his COVID-era entry into the options-trading subculture after being taught by a former bond trader. Brett describes early euphoric gains from a single strategy in a favorable market that led to confirmation bias, followed by significant losses when conditions changed and he wasn’t nimble enough to adapt, noting how traders often highlight winning trades while ignoring the full sample. They explain options as time-bound contracts to buy or sell an underlying asset (calls and puts), including how contracts themselves can be traded, and warn that complex combinations can create severe or even unlimited losses, citing a widely reported case of a confused young options trader who took his life and examples like meme-stock squeezes. They contrast investing vs speculating, critique overreliance on technical analysis, and conclude options are best for professional hedging, not retail “tinkering,” despite get-rich-quick allure.

00:00 Welcome and Setup

01:07 Subcultures and Finance

02:32 COVID Options Rabbit Hole

05:32 Highlight Reels and Bias

08:34 Big Wins Then Losses

10:25 Options Explained Simply

15:07 Derivatives and Real Danger

19:28 Casino vs Investing

21:42 Technical Analysis Debate

29:30 Selling Puts Insurance Analogy

35:56 Get Rich Quick Temptation

37:19 Final Warnings and Wrap

Links mentioned in this episode:

This week's blogpost - https://bahnsen.co/4tQ4xaA

Trevor Cummings hosts the Thoughts of Money Podcast with article author Blaine Carver and Brett Bonecutter, discussing Carver’s piece “Stock Market Expectations.” Using examples from relationships, premarital counseling, and sports fandom, they emphasize that expectations must be communicated early, clearly, and realistically to avoid disappointment, resentment, and poor decisions. They connect this to investing by explaining how stocks can fall even on good results when expectations are “priced to perfection,” why unrealistic return targets (e.g., 20–25% annually) break financial plans, and how compounding magnifies small percentage differences.

00:00 Welcome to the Thoughts on Money Podcast + Introducing Blaine & Brett

00:21 Under-Promise, Over-Deliver: Why Expectations Drive Everything

00:59 Vikings Season Story: Rock-Bottom Expectations → “Best” Year

02:05 From Football to Finance: Priced to Perfection & Pleasant Surprises

04:34 Expectations in Marriage (and Advisor-Client Relationships)

06:55 Unrealistic Return Targets: The 20% Conversation & Compounding Reality Check

10:39 Long-Run vs One-Year Thinking: Annual vs Annualized + Attribution

12:11 Strategy Whiplash: 2025 vs 2026 Reversal & Staying the Course

14:35 The Expectations Gap: Investors Want 12.6%, Advisors Model 7.1%

17:27 Why the Gap Exists: Valuations, History, and Risk Accountability (Bitcoin Example)

20:19 The “Road” Matters: Normal Drawdowns, Slow Recoveries, and the Bumpy Path

26:17 Coping Tools: Dividends, Business Fundamentals, and the 14% Intra-Year Drawdown

29:52 Optimists vs Pessimists: Experience, Confirmation Bias, and Fear of Running Out

37:37 Closing Reflections: Gratitude vs Grumbling + Final Thoughts & How to Reach Us

Links mentioned in this episode: