Investing, Optimism, AI, and Personality

#644: Why do we both crave money and resent it? Why do some people sabotage their financial futures in the name of short-term comfort? And why is your brain — not the stock market — the biggest threat to your wealth?

In this conversation, we explore the surprising ways that psychology and money intertwine. Our guest, Dr. Daniel Crosby, is a behavioral finance expert, psychologist, and bestselling author of The Soul of Wealth, The Behavioral Investor, and The Laws of Wealth. His research dives into how our emotions, childhood scripts, and personalities shape the financial decisions we make every day.

Dr. Crosby shares why investing is an act of optimism, why income matters more than coupon clipping, and how our spending reveals truths about who we really are — even when we don’t realize it..

Key Takeaways

• Money is a mirror. The way you earn and spend reflects your real values, not just your stated ones. Tracking your money reveals gaps between who you say you are and how you actually live.

• Income drives wealth. Frugality matters, but once the basics are handled, your long-term financial future is determined more by growing your income than by cutting costs.

• Short-term comfort is costly. The biggest threat to your wealth isn’t the market — it’s the temptation to prioritize momentary relief (panic-selling, stress spending) over your long-term goals.

Resources & Links

• Dr. Daniel Crosby on LinkedIn

• Standard Deviations Podcast

• Books by Dr. Crosby:

• The Soul of Wealth

• The Laws of Wealth

• The Behavioral Investor

• Personal Benchmark

Closing

This episode reminds us that building wealth isn’t just about math — it’s about mindset. The markets may fluctuate, but the greatest risks and rewards often lie within our own psychology.

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You can afford anything, but not everything. Choose wisely.

Timestamps:

Note: Timestamps will vary on individual listening devices based on dynamic advertising segments. The provided timestamps are approximate and may be several minutes off due to changing ad lengths.

(03:24) Does money really buy happiness? Rethinking the $75k income myth.

(08:48) Our conflicted relationship with money: Love, resentment, and the paradox of wealth.

(10:32) Childhood money scripts: How early beliefs still drive adult financial behavior.

(16:10) Personality traits & money outcomes: Why agreeableness and neuroticism matter.

(24:15) Investing as an act of optimism: Human progress, markets, and long-term growth.

(30:39) AI, work, and the future of wealth: Why EQ may outpace IQ in tomorrow’s economy.

(39:46) Habits vs. willpower: Why automation and environment beat discipline.

(44:28) Frictionless spending: How Apple Pay and subscriptions fuel overspending.

(47:32) Offense vs. defense in wealth: Why income matters more than extreme frugality.

(1:03:16) Chronic vs. episodic mistakes: Small leaks, lost compounding, and long-term damage.

(1:06:24) The pre-mortem exercise: A Stoic-inspired tool to prevent financial failure.

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