The Stacking Benjamins Show

Episode: Morgan Housel: Why You Spend Money (And How to Do It Better) SB1769
Date: December 3, 2025
Host: Joe Saul-Sehy ("Joe"), with OG
Guest: Morgan Housel

Episode Overview

This episode explores the "art" of spending money with renowned finance author Morgan Housel, delving deep into the psychological, cultural, and emotional factors that drive how and why we use money. With December’s holidays in full swing—“the spendiest month of the year”—the episode is dedicated to unraveling not just financial strategies, but the human motivations and philosophical questions behind our monetary decisions.

Key Discussion Points & Insights

1. Why It’s Called "The Art of Spending Money"

• Individual Approach: Morgan chose “art” instead of “science” or “strategy” because there is no universal formula (“There is no science to this. Whatever works for you is what's going to work for you.” – Morgan, 07:29).
• Money Is Personal: Factors like generation, culture, personal scars, and risk tolerance all affect financial habits. Spending, saving, and investing are shaped by unique internal forces, much like preferences in food.
• Guidelines, Not Rules: While concepts like compounding and debt risk apply broadly, psychological drivers are unique to each person.

2. Lessons from Morgan’s Valet Experience

• Wealth vs. Performance: As a college valet at a five-star LA hotel during the pre-2008 boom, Morgan saw firsthand the contrast between truly wealthy individuals and those performing wealth for others (“Most, if not nearly all…were not as happy or as successful as I thought they would be.” – Morgan, 09:57).
• Why People Buy Things: Flashy purchases often divide into those motivated by love of the thing itself vs. those wanting to impress others.
  • “Are you doing it because you truly love and enjoy this thing…or because you think…you are instilling some kind of admiration from strangers?” (Morgan, 12:15)

3. Admiration vs. Envy

• Seductive Attention: The thrill of attention brought by material goods is often misunderstood—people aren’t admiring you, but projecting their desires onto your possessions.
  • “They weren’t saying, wow, look at Joe. What they did is they said, if I was sitting in Joe's seat, people would be looking at me.” (Morgan, 14:02)
• Riches and Modesty: One of the richest hotel guests drove an old Toyota, demonstrating confidence and self-worth are disconnected from flashy displays.

4. Stop Judging Others’ Spending

• Spending Reflects Life Experience: Morgan encourages empathy, as spending/saving habits are rooted in life stories (“Never make fun of how someone spends money because they learned it from living.” – Joe summarizing Morgan, 16:55).

• Judgment and Self-Doubt: When we judge others' spending, we may be projecting our own doubts about our financial choices.

• Minimizing Regret, Not Maximizing Money: Avoiding future regret—balancing living for today with saving for tomorrow—should be central to all money decisions.

  “…if you are on your deathbed tomorrow, looking back at your life, what would you regret? And a good philosophy foundation for life is trying to minimize those numbers of regrets.” (Morgan, 17:18)

5. Rules of Thumb and Happiness (The 4%/5% Rule)

• Guardrails, Not Goals: Financial rules (e.g., the 4% rule for retirement) should serve as loose frameworks rather than strict constraints.
• True Contentment: Enduring happiness isn’t a function of how much you spend, but of contentment—wanting nothing more than what you already have.
  • “The happiest woman you will ever meet…had nothing and she wanted nothing else.” (Morgan, 22:10)

6. Does Money Bring Happiness?

• Research Insights: Earning more money amplifies your disposition; it makes happy people happier, but doesn’t “fix” despondency.

  • “If you are already a depressed…person, earning more money is not going to do very much for you…But if you are already a happy…person, then earning more money will give you a much better life.” (Morgan, 23:43)

• External Validation vs. Internal Value: Real fulfillment comes from impressing the people who truly matter, not strangers.

  “I desperately want and need the love and attention and admiration from about six people…Outside of those six people, it drops off very dramatically.” (Morgan, 26:05)

7. On Money Using You

• Be the Master, Not the Puppet: Too often, people let money (and others’ perceptions) dictate their desires and ambitions rather than using money as a tool to enable their authentic life.
  • “Money is not a tool that you are using. It is something that hijacked your personality… It’s like the puppet master controlling your life.” (Morgan, 29:05)

8. Being Mindful in a “Spendy” Month

• Contentment Trumps Obsession: The most content people use money for things they love but invest most thought into relationships, experiences, and well-being—not maximizing every dollar.

  “Just shut up and breathe. You can do it…That exists for money as well.” (Morgan, 29:55)

9. What to Want from Money

• Independence Above All: Morgan values money for the independence it brings, not for chasing systems or external validation.
  • “What I want out of money more than anything else is…independence. I just want to live life on my terms, my way, not under anyone else's system…” (Morgan, 31:24)
• A Window into Human Nature: Money is also a “clear window into people’s psyches”—fascinating for understanding human behavior and ourselves (32:16).

Notable Quotes & Memorable Moments

• On individuality in money:

  “There is no science of spending money…Whatever works for you is what's going to work for you.”
  — Morgan Housel, 07:29

• On performative wealth:

  “…they were not as happy or as successful as I thought they would be.”
  — Morgan Housel, 09:57

• On the illusion of attention:

  “They weren’t saying, wow, look at Joe...They were imagining themselves having that thing and dreaming about the attention that others would therefore give to them.”
  — Morgan Housel, 14:02

• On regaining perspective:

  “If you are on your deathbed tomorrow...what would you regret?...Trying to minimize those numbers of regrets.”
  — Morgan Housel, 17:18

• On contentment:

  “Wealth is what you have minus what you want...and she had nothing and wanted nothing else.”
  — Morgan Housel, 22:10

• On the true source of happiness:

  “It's absolutely possible to live an amazing life on very little money. It is within your control.”
  — Morgan Housel, 22:10

• On matters of comparison and envy:

  “Anybody driving faster than you is a maniac. Anybody driving slower...and we're always comparing ourselves to what other people are doing.”
  — Joe referencing George Carlin, 28:24

• On independence:

  “What I want out of money more than anything else is...independence.”
  — Morgan Housel, 31:24

Timestamps for Important Segments

• [07:02] – Why Morgan called his book "The Art of Spending Money"
• [09:57] – Lessons learned from working as a valet for the rich & performative spending
• [12:15] – Who buys flashily, and why
• [14:02] – The seductive power of being seen and the difference between admiration and envy
• [17:18] – Why we should stop judging others’ spending, and a poignant story on regrets and living fully
• [21:45] – Reframing retirement spending "rules" in pursuit of happiness, not just withdrawal rates
• [22:10] – On enduring happiness and contentment, highlighting the story of his grandmother-in-law
• [23:43] – Research on money and happiness: money leverages what you already are
• [26:05] – Impressing those who matter, not strangers
• [29:05] – “Money will use you if you let it”
• [31:24] – What Morgan himself wants out of money: independence and self-understanding
• [32:41] – The personal need to write “The Art of Spending Money”

Warren Buffett Retirement Headline ([37:42]-[47:08])

• After Charlie Munger’s passing, Warren Buffett is retiring at 95 as CEO of Berkshire Hathaway.
• Lessons from Buffett: mastery of fundamentals, commitment to simple but powerful principles, and maintaining composure in market chaos.
• Both Joe & OG discuss that change in leadership matters in active management, but not for passive investing.
• Buffett’s approach: value, not hype or technical “voodoo.”
• Light-hearted banter about how even the best investors made mistakes but succeeded more than they failed.

Tone and Style

True to Stacking Benjamins' reputation, the episode maintains a light, conversational, and at times humorous tone—even while discussing deep philosophical points on money. Joe and OG keep things approachable, peppering thoughtful insights with relatable stories and laugh-out-loud asides.

Conclusion: Actionable Wisdom

• There’s no universal script for spending; the art is in knowing yourself, your triggers, and your regrets.
• Build systems so you worry less about money and enjoy life more.
• Judge less—others’ money decisions are built from their lives, not yours.
• Happiness flows from contentment and independence, not endlessly increasing spending.
• Reflect regularly: If you were looking back from the end of your life, what would you regret not doing? Aim to minimize those regrets as your guide for spending.

For those new to Morgan Housel or curious about money psychology, this episode delivers the warmth, humor, and insight that make financial literacy engaging—and even a little philosophical.

Recommended: Morgan Housel’s book The Art of Spending Money is available wherever books are sold, and you can find links in the Stacking Benjamins show notes.