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10 Lessons for Better Decisions About Money and Life
21 October 2026

10 Lessons for Better Decisions About Money and Life

All the Hacks: Money, Points & Life

About
#299: My top 10 takeaways from a retreat for high-net-worth investors, which covered money, health, AI, parenting, relationships, and more. We explore why what you measure shapes your behavior, how to start using AI agents, why simple rules beat perfect plans, how to teach kids about money, and why “later” may be the most expensive word in your vocabulary.



Tad Fallows is the co-founder of Long Angle, a private community for investors with $3 million or more in investable assets. He previously co-founded iLab Solutions, a research software company acquired by Agilent Technologies.



Link to Full Show Notes: https://www.chrishutchins.com/10-lessons-money-parenting-ai-long-angle/



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Resources Mentioned


Long Angle




People & Books


Sahil Bloom



The 5 Types of Wealth by Sahil Bloom



Sahil Bloom's post on the 3 Levels of Listening



Andrew Taylor




Health


Oura Ring




ATH Podcast


#253: 10 Lessons That Challenged My Thinking on Money and Life



#297: Have Better Conversations and Build Deeper Connections with Vanessa Van Edwards



Hotel Upgrade Program



Best Cards Page



Gift Cards Page



Newsletter



AMA: Submit Questions



Leave a review: Apple Podcasts | Spotify



Email for questions, hacks, deals, and feedback: podcast@chrishutchins.com






Full Show Notes

(00:00) Introduction

(02:04) What You Measure Dictates What You Do

(05:57) Don't Let the Optimal Get in the Way of the Beneficial

(15:13) How to Get Started with AI Agents

(26:28) Why Established Managers Outperform Emerging Ones

(35:07) Good Plans Die in the Paperwork

(39:48) Simple Rules You'll Follow Beat Perfect Rules You Won't

(46:54) T.U.N.E. Parenting: Balancing Connection with Boundaries

(58:23) Your Environment Beats Your Willpower

(01:04:11) Talk Less and Ask Better Questions

(01:11:17) "Later" Is the Most Expensive Word

(01:18:55) The Meta Takeaway: Pick One Thing and Start Today



Connect with Chris

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