The Ramsey Show
The Ramsey Show

Debt Doesn’t Have to Run Your Life

September 24, 2026

AI Summary

5 min read

“I’m a licensed plumber, and within this past year I’ve proved to myself that this side business income can outdo my normal full-time income.” That’s Andrew in Providence, Rhode Island, calling into The Ramsey Show with a problem many people would love to have: his side business is making more money than his day job, and he’s terrified to quit. The hosts, Rachel Cruz and Jade Warshaw, spend the hour walking callers through a series of financial dilemmas that all point to the same underlying truth: your behavior with money matters more than any single number in your bank account.

The Leap of Faith: When a Side Hustle Becomes a Career

Andrew’s situation is the episode’s opening case study in how to think about risk. He’s a plumber with a full-time job paying $180,000 a year, but his side business with a partner is now generating over $300,000 in profit for him alone, with $70,000 in retained earnings. He’s been operating as an LLC for five years, growing organically from $25,000 in profit the first year to this point. His fear: leaving a secure, high-paying job for the unknown of running his own company full-time.

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What you'll learn

  • 1 Timestamped Outline
  • 2 (00:47) **Side Hustle Founder's Leap of Faith** - Andrew, a licensed plumber, asks when to quit his full-time job for a side business that's already outpacing his main income
  • 3 (10:35) **Retirement vs. Debt Dilemma** - Joseph, with $53K in credit card debt, wants to drain his Roth IRA to pay it off
  • 4 (22:22) **20-Year-Old's Rush to Homeownership** - Matthew wants to use a $40K forgivable down-payment grant to buy a $110K condo despite having $33K in consumer debt
  • 5 (29:43) **Micro Payments Strategy** - Angela from Facebook asks whether to make small extra payments on debt at the end of each pay cycle
  • 6 (33:37) **Baby Steps Quick Teaching** - Rachel and Jade walk through the seven Baby Steps and address why people feel they can't start
  • 7 (35:55) **When Values Don't Align** - Sophie, 25 with $220K invested and no debt, is dating a 29-year-old who hates working, thinks rich people are evil, and has no savings

+ Full timestamped outline available in the app

Show Notes

📈 ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Are you on track with the Baby Steps? Get a Free Personalized Plan.⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠

❓ ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Have a money question? Ask Ramsey is here to help.⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠


Rachel Cruze and Jade Warshaw answer your questions and discuss:

  • “My girlfriend wants to wait 20 years to get married so she doesn't lose survivor benefits”
  • “I am being sent to court by collections, should I reprioritize that debt and pay it off first?”
  • “My boyfriend and I have different views on money, should I break up with him?”
  • “How do we save to hire a caretaker for our son with special needs?”
  • “Our adjustable-rate mortgage matures in four years, should we cut back on our retirement investing in order to pay it off?”


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