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

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

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