Podcast Summary: "Why You Feel Broke Even When You're Doing Everything Right" (SB1761)

The Stacking Benjamins Show | November 14, 2025

Overview

In this lively, roundtable episode of The Stacking Benjamins Show, host Joe Saul-Sehy and OG revisit an eight-year-old discussion featuring rising personal finance star Erin Lowry (“Broke Millennial”), Afford Anything’s Paula Pant, and author/radio pro Greg McFarlane. The episode seeks to answer the perennial question: “Why does it still feel like you’re spinning your wheels financially, even if you’re making all the smart moves?” Through candid anecdotes, spirited debate, and plenty of humor, the panel explores the feeling of financial stagnation, the true levers behind getting ahead, and how unexpected or unconventional strategies (and jobs) can make a difference.

Key Discussion Points & Insights

1. Why Do You Feel Broke Even When You’re Doing Everything Right?

• Main prompt: Many people, even diligent savers, feel stuck. Why is that?
• Greg McFarlane opens by challenging the premise, suggesting many folks struggling financially make “self-inflicted mistakes” or avoid hard choices (22:10).

  “At least for me, every poor and underachieving person in my life is there largely because of self-inflicted mistakes.” — Greg McFarlane (22:44)

• Erin Lowry highlights dependence “expenses” like kids and pets, and questions the decision to stay in economically depressed areas out of comfort:

  “I see some people ... still not in a stable job because they won’t leave where they’re from. I have minimal sympathy for that. Strike out and go where the jobs are.” — Erin Lowry (24:09)

Key Takeaway:

• The panel stresses the importance of changing circumstances to improve one’s finances, whether that means side hustling or moving for opportunity.

2. Income Instability & Side Hustles

• Topic: How to handle uneven income when you’re self-employed/freelancing.

• Paula Pant and Erin Lowry share their personal journeys of transitioning from steady jobs to freelancing. Both used side hustles to create a financial cushion and developed frugal habits to weather lean months (28:07–29:48).

  “You can only frugal down so much. For many people, the emphasis really needs to be on earn, earn, earn.” — Paula Pant (24:51)

• Greg emphasizes starting with a dual-income household, but also “forcing yourself to float” by moving away from safety nets (27:08).

Key Takeaway:

• Building multiple income streams and maintaining a low-overhead lifestyle provide flexibility and resilience, particularly for those with uneven cash flow.

3. Barriers Built by the Financial System

• Erin Lowry passionately addresses structural obstacles like bank fees that disproportionately hurt people with less buffer.

  “I always ask college students if they’re at the same bank as their parents... Big banks got $5.1 billion in overdraft fees [in 2015]. They’re using your overdraft fees to pay for things like naming rights to stadiums.” — Erin Lowry (30:42)

• The sense of “the system is rigged for the rich” is an undercurrent, but the panel agrees that knowledge (and sometimes moving to a better bank) is empowering.

Key Takeaway:

• Bank with intention, and don’t be afraid to switch for better terms or avoid predatory fees.

4. Stop Worrying and Start Saving: Article Analysis

• The group reviews a retirement advice article and mostly finds it lacking in actionable depth or nuance (32:33–35:22).

  “Being weighed down by student debt makes you a whole lot dumber about money than your parents were.” — Greg McFarlane (32:41)

• Paula and Erin discuss the importance of understanding contribution rules (for things like 401(k)s and IRAs) and calculating how much you can actually sock away (34:14–36:50).

• Automated contributions and “boiling the frog” by slowly increasing savings over time is advocated.

5. Getting Creative: Odd Ways to Make Money

• The panel shares and laughs about unexpected or weird money-making ideas, from cuddling services (46:44), being a mascot (51:44), to pet-sitting empires (49:26).

  “When I first moved to New York, I was a barista at Starbucks... and would take home all the ‘expired’ foods. I lived off those paninis and bistro boxes for a very, very long time.” — Erin Lowry (49:26) “Art classes, University of Toronto. Modeling. It’s just like the radio voiceover thing, except nothing moves, including the mouth.” — Greg McFarlane, revealing he did nude modeling for art classes (51:00)

• Paula’s stint as “The Salty Dog” mascot (51:44) underscores how unusual gigs can help cover bills or serve as creative networking opportunities.

Key Takeaway:

• Don’t be afraid of unconventional work—often, small odd jobs or side hustles can meaningfully boost your savings and create fun stories along the way.

6. Memorable Quotes & Moments (with Timestamps)

• “It’s the paying attention to spending and the automation of saving and ... putting it out of your mind, but doing it wisely.” — Steve Stewart (05:48)
• “You can only frugal down so much. For many people the emphasis really needs to be on ‘earn, earn, earn.’” — Paula Pant (24:51)
• “Going where the jobs are, where the opportunities are ... it’ll force you to stay afloat.” — Greg McFarlane (27:31)
• “I do monthly net worth updates and track all side hustle income ... If I went all in, I could out-earn what I was when I was working for the man.” — Erin Lowry (25:32)
• “Getting rid of clutter actually has a positive effect on your net worth.” — Paula Pant (48:31)

Important Segments & Timestamps

| Segment | Timestamps | |------------------------------------|--------------| | Intro/Background & Announcements | 00:00–15:14 | | Roundtable Introduction | 17:43 | | Feeling Stuck Despite Doing “Right”| 22:10–24:32 | | Side Hustles & Income Instability | 24:51–29:48 | | Bank Fees and Banking Structure | 30:15–31:30 | | Retirement Saving Article Critique | 32:15–41:33 | | 7 Strange Ways to Make Money | 45:51–55:10 | | Fun Anecdotes (Mascots/Nude Modeling)| 51:00–55:10| | Wrap-Up & Plugs | 55:11–58:57 |

Original Tone & Energy

• The Stacking Benjamins signature is light, irreverent, and welcoming, often poking fun at themselves, listeners, and the financial advice industry.
• The guests joke, make pop culture references (like “Anchorman” and The Simpsons), and keep the conversation fast-paced.
• Despite the fun atmosphere, the advice centers on practical, everyday steps and real-life stories that make the lessons relatable.

Conclusion & Action Items

• Feeling “broke” doesn’t always reflect your actual net worth—it can stem from income instability, lifestyle choices, location inertia, or simply unfair systems.

• Key actions for listeners:

  • Review your automatic savings and gradually increase contributions.
  • Consider creative or odd jobs for side income.
  • Don’t be afraid to move for better opportunity.
  • Regularly reevaluate your banking relationships to avoid unnecessary fees.
  • Remember, boosting your income can be as important as budgeting frugally.

• Final word from Erin Lowry:

  “You can actually get the book [Broke Millennial] and a bonus chapter if you preorder and send proof to infookemillennial.com.” (58:35)

For more information:

• Find Erin Lowry at brokemillennial.com
• Paula Pant at affordanything.com
• Greg McFarlane’s book “Control Your Cash” on Amazon