The Ramsey Show – Episode Summary

Episode: “We’re in Way Over Our Heads With $1.5 Million in Debt”

Date: November 26, 2025
Host: Dave Ramsey
Co-Host: Jade Warshaw Ramsey

Overview

In this episode, Dave Ramsey and Jade Warshaw take on a range of intense, emotional, and practical financial calls from listeners. The central arc is a young couple with staggering business and personal debt, seeking a roadmap out of financial catastrophe. Along the way, the hosts address buying cars while in debt, coping with financial stress during the holidays, lending money to loved ones, dealing with payday loans, the emotional reality of financial setbacks, and the impact of massive wealth on spending decisions. The episode is rich with personal stories, teachable moments, and Dave’s signature tough love balanced with empathy.

Key Discussion Points

1. Caller Heather – $1.5 Million in Debt (00:43–10:02)

• Situation: Heather (age 28) and her husband are over $1.3M in debt due to a failed business purchase, back taxes, mortgages, car loans, and credit card debts.
• Breakdown of Debts:
  • House: Owe $48k (Home value: $250k)
  • Cars: Owe $17k
  • Credit Cards: $19k (business and personal)
  • Back Taxes: $30k
  • Business Loan (SBA): ~$1.2M
• Business Story: Started a summer camp, then bought an event rentals business (assets only) for $1.2M, funded via SBA loan. Discovered they significantly overpaid due to hidden issues.
• Income: Summer camp generates $200k/year but is seasonal, as is the rental business.
• Current State: Business is not bringing in enough to service the debt; they’re “overwhelmed,” unsure if they can sell assets to get out without a major loss.
• Notable Quote (Dave, 05:15):
  “When life looks like a country song, it just looks like a country song. Lots of people still renting kids stuff all over the place. The economy’s quite booming in some areas, but so. No, the economics at your house suck, and so. I’m so sorry, honey. It’s so scary.”

Dave’s Advice

• Consider selling the business for whatever they can get, even if it creates a large shortfall.

• Propose a short sale to the SBA, leveraging their unwillingness to repossess event equipment.

• Pay the IRS before anyone else ("Pay the KGB, I mean, the IRS").

• Emotionally prepare for possible bankruptcy.

• “...the worst case scenario is you lose the business, you lose the camp, and you start your lives fresh after a bankruptcy. And you hold on to each other, and you hold on to Jesus and you hold on to your marriage. And so what? Okay? Lots of people have gone broke.” (06:42)

• Jade and Dave on teachable moments:
  “There’s a proverb that says the simple see trouble and move forward, and the wise avoid it and take refuge, and the simple are punished for it.” (14:34)

2. Jay – Transitioning Veteran, Car Purchase Decision (16:58–19:55)

• Situation: Recently out of Army, moving for new job, limited cash, wants to buy a car but is in debt payoff mode.
• Ramsey Advice:
  • Don’t go backwards by taking out a car loan.
  • Use current savings to buy a car outright, even if less reliable or less new; wait until finances improve for upgrades.
• Dave’s Quote (19:42):
  “Can’t get out of a hole while digging out the bottom. So, yeah, you’re going to go buy it, though. I kind of think we can talk you out of it in 30 seconds. But no, there’s no chance I’ll ride a bicycle before I get a freaking car payment again.”

3. Holiday Stress, Debt, and Four Jobs – Bo in New York City (33:18–42:31)

• Situation: Struggling father with four kids, $123k of debt (SBA, student loans, credit cards, car loan), wife at home homeschooling, working multiple jobs, still stuck.
• Emotional Impact: He’s overwhelmed, exhausted, can’t form sentences.
• Advice: Drastic change is needed – possibly move, have wife find work, change career path, sell everything.
• Memorable Moment:
  “You are not stuck, but you are going to have to change something… You need to play this back and listen to it… you’re defeated is everything that comes up. I’m already defeated. I’ve already lost. …and you have not lost. You’re a hard working guy…” (39:18)

4. Helping a Broke Ex-Girlfriend Facing Eviction – Carl in Chicago (44:46–51:25)

• Situation: Recently broke up, ex is facing eviction, caller has only $7,000 and no debt, ex has patterns of poor money management.
• Advice:
  • Don’t sacrifice your own financial stability.
  • Setting boundaries is not cruelty; helping only if child is at-risk and no other options.
• Jade’s Point:
  “...it would be enabling. I think that it would be for her, somebody who’s just kind of softening the fall.” (51:25)
• Dave’s Classic Take:
  “You’re not Jesus; that’s his job. You can’t do his job for him.”

5. Caller Alex – Payday Loan Trap (54:55–58:58)

• Situation: Unemployed, sunk into payday loan cycle at exorbitant (500%) APRs, new job starts soon.
• Advice:
  • Cover basic needs first: food, electricity, rent.
  • Avoid payday loans at all cost in the future.
  • Consider changing bank account to stop auto-drafts.
• Notable Quotes:
  • “Don’t you ever walk in those places again and borrow money the rest of your freaking life. Remember the pain of this and remember the stupidity of this and the ridiculous trap that you voluntarily stepped into so you never do it again.” (57:36)
  • “You stepped in a bear trap and guess what? It ripped your leg off. Oh, my gosh.” (59:01)

6. Prenups and Financial Transparency – Brian in Minneapolis (61:39–71:18)

• Situation: Engaged, worth nearly $20M, fiancée doesn’t know full amount, lawyer pushing prenup.
• Advice:
  • Full financial disclosure should happen before engagement.
  • Apologize for lack of transparency and unpack wealth details in person.
  • Prenup is reasonable with such a large financial disparity, but should not substitute for trust.
• Key Advice (Dave, 68:44):
  • “You shouldn’t ask someone to marry you that you can’t be honest with and transparent with that you don’t trust.”
  • Jade: “If Sam Warshaw came to me with this conversation, I’d be like...the door is that way. We’d be done, bud.”

7. Massive Wealth and “Outrageous” Purchases – Robin in Orlando (96:47–103:36)

• Situation: Retired, $20M net worth, husband wants to buy a $300k Shelby. She’s uncomfortable with such a large expense.
• Discussion:
  • Dave helps her contextualize: this is like buying a biscuit for someone with $20k; with $20M, $300k is negligible.
  • Emotional memories of being broke can clash with the realities of wealth.
  • Dave encourages honesty (“I think it’s dumb, but he’s earned it.”) and reminds her of the leverage their net worth provides.
• Notable Quote:
  “The stock market will move on your $20 million worth of investments. More than $300k in the next 60 days, up or down, and you won’t even look at it.” (100:02)

8. Emotional Cost of Child Support – Caller Jennifer (76:35–85:02)

• Situation: Remarried, dealing with resentment over husband’s ongoing child support obligations, ex-wife drama, husband recently laid off.
• Advice/Insight:
  • Separate financial support for the child from emotions about the ex.
  • Focus on the children as the beneficiaries—not the ex.
  • Jade: “I’d be picturing the child. Because the fact is, if you make a human being, you got to pay for them, period.” (79:22)
  • Dave and Jade validate her feelings, but urge shifting the focus to the next generation and practical acceptance as the path forward.

9. Other Notable Segments

• Compound Interest Teaching:
  Dave walks listeners through the concept of compound interest, the long-term costs of 30- and 50-year mortgages, and criticizes political stunts proposing “solutionary” loan products.
  “A 50-year mortgage has no mathematical substantiality...if it cut your payment in half, we could talk about it, but it cuts it 16%. Don’t be stupid.” (94:12)

• Financial Triage Calls:

  • Advice on using savings for car purchases versus fearing money drain.
  • Prioritizing emergency fund savings, budgeting, and not using debt as a problem solver.
  • Using “teachable moments” from financial regret as motivation for change.

Memorable Moments & Quotes

• Dave Ramsey (Addressing Huge Debt, 07:28):

  “I would sell it for whatever you can get for it. If you can get 800,000 for it, take it, okay? And go to the SBA and do a short sale. ... And honey, if you don’t take this 800, because I’m walking and you’re going to own a blow up inflatable, and the SBA is not in the inflatable business.”

• Jade Warshaw (On Emotions in Money, 25:49):

  “If you can’t be specific, you can’t solve it. Now, this guy could say, well, here. Here’s what I’m afraid of, Jade. I’m afraid if I drain my savings down to 10,000 and get a $10,000 car, I’m afraid my AC is going to break and it’s going to cost 12,000. Right. Tell me exactly what you’re afraid of. Then we can go back and we can go, well, let’s play out the worst possible scenario.”

• Dave Ramsey (Addressing Grieving Sister, 120:04):

  “If you and your husband sit down and say, we’re going to take X number of time off and just, we’re not going into debt, we’re not going to grief spend, but we’re just going to take some time off at the intensity and cry a little, that would be perfectly fine.”

• On “Throwing Dynamite at a Logjam” (Bo in NYC, 39:18):

  “You’re the plate spinningest dude I’ve talked to in I don’t know when, and these plates are crashing all around you, and you’re scared to death. ... There’s an old thing… that’s how you bust up a log jam. You bust up some stuff. Now, I don’t know exactly what it is in your life, but I’m going to start selling everything in sight… You cannot be saying the same exact sentences you’re saying to me right now [next year].”

Timestamps for Notable Segments

• 00:43–10:02: Heather’s catastrophic business debt – tough love advice and emotional support.
• 16:58–19:55: Military vet transitioning to civilian life – buying a car while paying off debt.
• 33:18–42:31: Bo in NYC, overwhelmed by four jobs and family obligations – theme of being “stuck.”
• 44:46–51:25: Carl in Chicago, boundaries in helping an ex-girlfriend financially.
• 54:55–58:58: Payday loan cycle – how to get out and never return.
• 61:39–71:18: Brian and the prenup – transparency, pre-engagement conversations, and handling massive net worth.
• 76:35–85:02: Jennifer’s resentment about child support – refocusing on children, not ex-spouses.
• 96:47–103:36: Robin struggling with her husband’s $300k car purchase – emotional vs. mathematical perspectives.
• 120:04–126:18: Megan dealing with the grief of losing her brother and pausing her debt snowball.

Takeaways & Tone

The entire episode is laced with Dave’s signature mix of stern, practical financial counsel and deeply empathetic acknowledgment of callers’ pain and fears. Jade Warshaw contributes both practical strategies and an understanding of the emotional complexities in financial decisions. The hosts repeatedly return to themes of personal responsibility, learning from mistakes, seeking financial and emotional support, and focusing on relationships over riches. They don’t shy away from the reality that sometimes bankruptcy or starting over isn’t the end of life, but can become the beginning of a new, wiser chapter.

Overall, this episode highlights that anyone – regardless of past mistakes or current crisis – can find hope, but only if they’re ready to change, face reality, and above all, put people before possessions.

Episode Highlights & Quotes

• On overwhelming debt:
  “So what? Okay? Lots of people have gone broke. That’s the worst case scenario. So I want you two to sit down tonight and accept that emotionally and look at each other and hold hands and say, we got this together no matter what.” — Dave Ramsey (06:42)

• On buying cars while broke:
  “Can’t get out of a hole while digging out the bottom.” — Dave Ramsey (19:42)

• On enabling others:
  “You’re not Jesus; that’s his job. You can’t do his job for him.” — Dave Ramsey (50:28)

• On payday loans:
  “Don’t you ever walk in those places again and borrow money the rest of your freaking life. Remember the pain of this...” — Dave Ramsey (57:36)

• On resentment over child support:
  “I’d be picturing the child. …Because if you make a human being, you got to pay for them, period.” — Jade Warshaw (79:22)

• On emotional spending during grief:
  “It’s easy to medicate grief with spending. A lot of people do it, and so be careful with that.” — Dave Ramsey (119:50)

For Listeners Who Missed This Episode

This episode is a masterclass in financial triage, emotional resilience, and learning from the worst mistakes. Whether you’re wrestling with giant debt, struggling to help a loved one without hurting yourself, or wondering whether you “deserve” a big purchase after years of sacrifice, Ramsey and Warshaw’s no-nonsense yet compassionate advice offers a way forward—and plenty of tough love and laughter along the way.

If you want to build wealth, first you must take a hard look at your own behavior, face up to your past, and decide—never again. Hope is real, but only if you act on it.