Podcast Summary: The Stacking Benjamins Show

Episode: Does More Money Actually Make Life Easier? (Spoiler: Not Really) SB1773

Date: December 12, 2025
Host(s): Joe Saul-Sehy, OG, Doug (Joe's Mom's Neighbor Doug)
Guests: Paula Pant (Afford Anything), Jesse Kramer (Personal Finance for Long Term Investors)

Overview:

This episode dives into the question: Does more money actually make life easier, or does it just bring more chaos? Inspired by a Wall Street Journal article titled "The More Money I Have, the Worse I Am at Managing It," Joe, OG, Paula, and Jesse reflect on their own financial journeys, discuss research showing that people with less money often manage it more attentively, and debate whether good money habits deteriorate with rising income. The roundtable balances lively banter, personal anecdotes, and actionable insights, all with a tone that's light, self-deprecating, and honest about financial growth and stumbles.

Key Discussion Points & Insights

1. Reflecting on Early Money Management Habits

(Starts ~11:45)

• The Article’s Premise: The episode is spurred by Julia Carpenter's WSJ piece; she notes that when she had little money, she managed it perfectly; with more, she was sloppier.
• Panel Reactions:
  • Paula: Never overdrew her account in college. Was "obsessive about tracking my money... sweating over every carton of orange juice, every roll of toilet paper — it all mattered." (12:00)
  • Jesse: Had a similar experience. "I know I've done [overdraft] once...within the last couple of years, which maybe is to Julia's point about getting worse as time went on." (12:12)
  • OG: Not sure but believes he definitely bounced some payments in early adulthood. Notes, "When you don’t have a lot of income, everything counts." (13:06)
  • Joe: Admits he was skilled at overdrawing in college, reinforcing how limited means make you careful.

2. Early Wins, Confidence, and Overconfidence

(15:00)

• Gaining Confidence: The panel reflects on how early financial struggles or wins shape confidence.
  • OG: "There wasn’t a single thing that was going right...it was all self-inflicted struggle....When I finally took responsibility...I got a little bit more control." (15:31)
  • Joe: He was "very confident, maybe overly confident, in my ability to make money...I’ll just go make more money," which led him to neglect budgeting and discipline (17:00)
  • Paula: Contrasts with the others. "Where I was not confident was my ability to make more money...I was too scrappy, too frugal...not thinking about growing." (20:57)

Notable Quote

"Once I realized to your point, nobody's coming to save me...the only person that could save me is me. That was it."
— Joe Saul-Sehy (18:58)

3. Research: Is Scarcity a Teacher?

(24:08)

• The WSJ article references research from UChicago showing that those with less money often track it more obsessively.
  • Jesse: Thinks limited resources force valuation: "It's a supply and demand thing — if you don't have much of something, you value it a lot." (24:08)
  • Doug: "Success is the worst teacher…you learn nothing from success; it’s all the hardships and mistakes that you learn from." (25:16)
  • OG: Chimes in with humor about the disappearance of pennies: "From now on, we have to say nickels. Right? I gotta stop pinching my nickels." (25:57)

Notable Quote

"When you've made mistakes that have caused you to be in a situation to only have pennies, you're going to learn a lot from that."
— Doug (25:46)

4. Does Complexity Grow Along with Wealth?

(27:08 & 30:16)

• OG: Discusses Nick Maggiulli's wealth ladder and the "0.01% rule"—as net worth increases, the focus on minor decisions decreases.
  • Below ~$80,000: Every dollar counts (groceries, gas, etc.).
  • ~$150,000: Worry shifts away from the details (e.g., gas, groceries).
  • $300,000+: Dining and wine list choices become less consequential.
• Jesse: Agrees, “Nothing...frustrates me more than...When someone drives across town to save 11 cents on gas." (31:48)

Memorable Moment

• OG's Steak Brother story: His brother thought “special” meant discount at a steakhouse—turned out to be the most expensive dish; drove home how money assumptions change as income increases. (32:58)

5. Do Good Money Habits Atrophy When Money Is Plentiful?

(46:27)

• Paula: Argues habits should adapt rather than disappear. Recommends the "anti-budget" — focus on just a few big categories (save, spend; or needs, wants, savings). "You can get rid of...granularity...while still having some sense of where your money’s going." (46:27)
• Jesse: Cautions that slippage is almost inevitable as income rises — "You just cut yourself a little bit of slack...to spend more frivolously here or there." (48:17)
• OG: For their family, extra spending is on "freedom-related activities" that reclaim time (help at home, convenience, etc.).

6. Balancing Time, Money, and Attention as Resources

(53:43)

• Paula: Stresses that attention and time become more precious as money grows: "We’ve got time, we've got money, we've got focus...attention is an increasingly scarce resource." (53:43)
• Doug/OG/Jesse: Allude to reframing time as a resource. The goal isn’t just money, but what money can buy in terms of reclaiming freedom, comfort, or joy.

7. The Dangers of Overcomplication

(55:11)

• OG: "As I got more money, I began to overcomplicate it...overabundance of systems...made it a mess." He references investing: "How many different ETFs do you need that say S&P 500? The juice is not worth the squeeze." (56:24)
• Jesse: Jokes about diversification fallacies (“If I have the S&P 500 at Schwab and at Fidelity and at Vanguard, I’m diversified, right?”).
• Multipliers vs. Simplifiers: Joe and OG play these roles in business: Joe tries everything, OG tries to keep it efficient.

8. Joyful, Free Experiences Don't Require Wealth

(58:28)

• Paula: "Just going on a long walk...anywhere outdoors. Long walk, totally free." (58:28)
• Jesse: "Hanging out with people can be really cheap...just socializing."
• OG: "Just being outside is a great use of time and energy...it doesn't cost hardly anything."

Notable Quotes & Moments

• OG on Personal Responsibility:
  “Once I said, okay, now I can undo some of these things. I think that's where I got a little bit more... control.” (16:58)

• Paula on Income and Mindset:
  “My mistake, really, in my 20s was that I was too scrappy, I was too frugal...I wasn't thinking about growing. I was thinking much, much more about shrinking.” (20:57)

• Joe on Complication:
  “It also strikes me as I got more money, I then began to overcomplicate it...created this overabundance of systems...that just jumbled me up and made it a mess.” (55:11)

• OG on Spending Philosophy:
  “If I’m spending money and it’s not producing a result...in terms of a freedom result...that’s where I find a lot of frustration.” (49:27)

• Doug on Success and Learning:
  “Success is the worst teacher in the world. You learn nothing or very little from success. It's all of the hardships and the mistakes that you learn from.” (25:16)

Timestamps for Key Segments

• 11:45 — Panel reflects on college/beginning-of-career money management
• 15:00 — Early confidence (over- and underconfidence) about money
• 24:08 — Are people with less money better at managing it?
• 27:08 — Do problems get more complex with wealth, or do we get lazy?
• 30:16 — When does obsessing over little expenses stop making sense?
• 32:58 — OG’s Steak Brother “special” story (hilarious, teaches about money context)
• 46:27 — Is it ever OK to graduate from budgeting?
• 48:17 — Does “only spend on joy” really work?
• 53:43 — Managing limited time, attention, and money
• 55:11 — Do we overcomplicate finances as we get wealthier?
• 58:28 — Favorite absolutely free or low-cost joys

Tone & Language

True to "Stacking Benjamins" style, the hosts balance actionable finance wisdom with banter, self-deprecation, and generous sharing of past mistakes. They’re unafraid to poke fun at each other, and themselves, keeping the tone encouraging and relatable: “Nobody’s coming to save me...the only person that could save me is me.” (Joe, 18:58) and “I have no idea how much gas costs...I don’t want to be a jackass.” (OG, 31:48).

Conclusion

Main Takeaways:

• More money doesn’t always mean less chaos—sometimes it brings the temptation to cut corners or overcomplicate.
• Early scarcity trains you to value each dollar—and those skills (budgeting, awareness) should be adapted but not discarded as income increases.
• True wealth might mean spending money where it matters (buying back time, convenience, or joy) and letting go of minutiae that no longer move the needle.
• Simplicity, attention, and joy can get lost in abundance—keeping habits and priorities aligned matters most.

“It strikes me…we start off tracking every penny because money is precious, and over time, time becomes the precious resource, and that changes your spending.”
— Joe Saul-Sehy (53:43)

[Segment Guide with Timestamps]

| Topic | Speaker(s) | Timestamp | |-----------------------------------------|-----------------|--------------| | College budgeting recollections | Paula, Jesse, OG, Joe | 11:45–13:06 | | Early “confidence” & missteps | OG, Joe, Paula | 15:00–21:58 | | Research: Poor = better with money? | Jesse, Doug, OG | 24:08–27:08 | | Income thresholds for spending concern | OG, Jesse | 27:08–32:19 | | Losing the budgeting habit? | Paula, Jesse | 46:27–48:17 | | Shifting focus to time, attention | Paula | 53:43 | | The dangers of complexity | OG, Jesse | 55:11–58:10 | | Free joys and contentment | Paula, Jesse, OG| 58:28–59:53 |

This summary preserves the hosts’ friendly, accessible style and major insights, making it valuable for those who missed the episode but want the full story and actionable takeaways.