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

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:

• http://thoughtsonmoney.com
• http://thebahnsengroup.com