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The Ramsey Show

The Ramsey Show Live From Chicago

Published October 17, 2025
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About This Episode

This live episode of The Ramsey Show is recorded in Chicago with hosts taking questions from the audience about money, relationships, and life transitions. Topics include setting financial boundaries with parents, resolving spender-saver conflicts in marriage, supporting low-income communities, navigating mid-journey Baby Steps, and finding meaningful work after a military career. The show ends with a collective debt-free scream and encouragement for attendees who are changing their family trees.

Topics Covered

Budgeting Debt payoff Relationships Marriage Poverty and inequality Career transitions Military veterans Live events Talk radio Personal Development

Disclaimer: We provide independent summaries of podcasts and are not affiliated with or endorsed in any way by any podcast or creator. All podcast names and content are the property of their respective owners. The views and opinions expressed within the podcasts belong solely to the original hosts and guests and do not reflect the views or positions of Summapod.

Quick Takeaways

  • You cannot force a family member to change their financial behavior; the only real control you have is over your own boundaries and whether you will lend or give money.
  • Lending money to relatives, even when they pay it back, can strain relationships and often turns you into a payday lender instead of a loved one.
  • In couples, spender-saver conflicts usually reflect deeper issues like fear, upbringing, and lack of trust or shared visibility into the budget, not just the dollar amounts.
  • There is a difference between enabling long-term financial misbehavior and providing short-term help to someone who is genuinely hurting.
  • People in economically depressed areas often face a long, difficult path that may include increasing skills, finding new work, and sometimes relocating to escape systemic poverty.
  • Boredom and slower progress are normal in the middle Baby Steps; shifting from pure intensity to intentionality and setting specific principal-reduction goals can keep motivation alive.
  • Veterans leaving the military can regain a sense of purpose by inventorying their skills and experiences and mapping them to civilian roles, then openly sharing what they're looking for with their network.
  • Tracking and celebrating wins-like group debt-free milestones-reinforces hope and shows how many ordinary people are changing their financial futures.

Podcast Notes

Live introduction and show setup in Chicago

Opening energy and context

Hosts welcome the live audience at the Den Theater in Chicago and frame the show as helping people transform their lives because "normal is broken" and "common sense is weird"[0:30]
They briefly joke about being in Chicago and eating deep-dish pizza on stage, setting a relaxed, fun tone before starting questions[1:45]

Transition to live audience questions

Hosts explain they will be answering live questions from audience members, including couples, which is something they enjoy but do not get to do as often on the regular show[2:12]

Question 1: Lending money to mom and setting boundaries

Couple describes mom repeatedly borrowing money despite higher income

Shay and Arnold from Portage, Indiana share that Shay's mom occasionally asks to borrow money, even though her household income is higher than theirs[2:31]
They ask for tips to help her budget, as she keeps asking for money instead of advice[2:39]

You cannot change someone who does not want to change

One host says a major life lesson, reinforced by extensive therapy, is realizing you cannot change people unless they genuinely want to change[2:53]
• Even if you desperately want a parent to budget, live on less than they make, and handle money responsibly, it will not stick without their own desire
Advice: either set a strong boundary that you will not give her money going forward, or gently offer help if she is curious about learning a new way to handle her money[3:30]
• Wording suggestion: "Mom, I love you, but we have a set plan for our income, and we're not going to be able to help you with money in the future"

Direct boundary setting from the child to the parent

Another host presses whose mom it is and tells Shay she needs to say "Mom, no more" and acknowledge her mom is a grown adult who needs to stop this pattern[4:02]
• He frames it as a life stage shift where the child becomes the parent and the parent becomes the child in terms of responsibility
He notes this repeated borrowing is causing strife for the couple, and that Shay must put up a boundary and be prepared for the conversation to be hard[4:33]

Preserving the relationship by not becoming a lender

Advice to tell her mom: "I love you. I'm your daughter. I don't want to become your lender. I care about our relationship too much for it to become a business transaction."[5:07]
• They warn that lending can lead to awkwardness where the parent avoids the child because they owe money, which damages holidays and family time
They suggest that if things go badly, she can share Ramsey content with her mom later, but the first step is saying no in love[5:25]

Assessing the current lending pattern and emotional impact

Shay explains she has already given her mom money, about twice a year, amounts ranging from a few hundred dollars to around $1,000-$2,000 (e.g., when the refrigerator broke)[6:13]
She notes her mom has always paid her back and sometimes very quickly, including one instance where the mom repaid the next day, which made Shay angry because it showed how tight the cash flow was[6:20]
• The quick repayment suggested the mom is living so close to the edge that she cannot float expenses even between paychecks and is using her daughter as a bridge
A host labels this dynamic as Shay essentially being her mom's "payday lender," loaning money to get her from one payday to the next[6:32]

Husband's stress and being stuck in the middle

Arnold shares that the situation puts him in the middle; he wants to be a lender and not a borrower (citing the Bible) but does not want to be the only solution every time the in-laws need money[7:01]
• He feels tension between wanting to help and feeling used, especially as it is his mother-in-law and they work together with her
The hosts point out that he is clearly stressed and urge Shay to hear how this is affecting him emotionally[7:41]

Recognizing enabling behavior and the need for mom to hit bottom

Shay explains she has already tried to help her mom, including buying a budgeting app and discussing every transaction, but her mom resists deeper help out of fear[8:19]
One host bluntly says the idiotic behavior is not the mom borrowing but the daughter continuing to help in a way that enables the problem, even though he clarifies he is not calling Shay an idiot[8:40]
• He suggests the mom is financially broken, while the couple is not, and that the mom will likely need to hit "rock bottom" financially before she's truly open to change
They prepare the couple for the likelihood that mom will come back repeatedly after the first boundary, and they must be ready to keep saying no[9:46]

Segment: Giving vs lending to family members

Distinguishing loans from gifts

Rachel clarifies there is a major difference between lending money (expecting repayment) and giving money (with no strings attached)[10:11]
• She states that lending to family and friends should be a firm no because it mixes relationships and business and almost always causes problems
She notes that in some situations, giving can be appropriate if the couple is financially stable, unified in the decision, and the gift is truly needed rather than enabling entitlement[10:35]
• Her recommendation in Shay's situation is to cut off all lending immediately and likely also cut off giving for now due to the pattern of misbehavior

Humorous aside about a past borrowing request

George jokes that years ago he once asked a cohost to front him money for an expensive blow dryer when he wasn't making much at Ramsey, and the cohost had to say no, illustrating how awkward lending can be even among colleagues[11:03]

Segment: "Settle the debate" - spender vs saver couple

Introduction of Jenny and Jake's money conflict

Jenny and Jake from Valparaiso, Indiana describe the "age-old" spender vs saver debate in their marriage; Jenny is the spender who wants to relax and spend, while Jake is the saver who wants to keep gazelle intensity[12:12]
They are in Baby Steps 4, 5, and 6, with Jake wanting to maintain intense focus on paying off their house, while Jenny wants more room for lifestyle spending like vacations, clothes, and Amazon purchases[12:12]

Details of income, family, and goals

They share that they make just under $160,000 per year on a single income; Jenny is a stay-at-home mom with four young children aged 7, 5, 3, and 6 months[13:49]
Jake has a Baby Step 6 plan to pay off their mortgage in five years, which would make them completely debt-free with a paid-for house by age 40[14:25]

Disagreement over spending amounts and budget visibility

Jenny says she wants to spend on modest lifestyle items (vacations, clothes, Amazon) and suggests a figure of about $400 more per month, which Jake says she "already gets" on average[15:09]
Jenny explains she does the budget herself; Jake doesn't want to look at it, and she identifies as both the spender and the nerd who loves budgeting[15:44]
• Because he's not looking at the budget, Jake often doesn't know the cost of things but still reacts negatively when multiple Amazon packages arrive or when she makes small upgrades like guacamole

Coaching: gazelle intensity vs intentionality

George pushes back on Jake's phrase about keeping "gazelle intensity" in Baby Steps 4-6, explaining that gazelle intensity is primarily for Baby Steps 1-3 (debt payoff and building an emergency fund)[15:34]
He says that once you're out of debt and have an emergency fund, the goal is no longer raw intensity but intentionality, which includes increasing sinking funds and occasional lifestyle upgrades within a plan[17:15]

Exploring deeper roots of money conflict

Rachel asks Jenny about her upbringing with money; Jenny explains they "had what we needed, but nothing more," and that there was stress around money[19:07]
• Rachel uses a story of a friend upset over buying more expensive milk to illustrate that seemingly small money fights often reflect deeper issues of security, fear, and whether "things will be okay" financially
She notes that Jenny likely feels shame and guilt when spending within the agreed plan, because Jake's reactions make her feel she doesn't have permission to enjoy their income[20:12]
She emphasizes that Jake's habitual side-eye over every purchase is hurtful and signals a lack of trust, which needs to be addressed at a deeper emotional level[21:16]

Judges' rulings and action steps

Rachel rules in favor of Jenny, saying the spending level is reasonable given their income and that Jenny uses a budget and tracks everything; she affirms Jenny's freedom to spend within the plan[21:22]
George also sides with Jenny, with a caveat that Jake must begin looking at the budget, find a hobby, and force himself to create and actually use a personal spending line item; Jenny will hold him accountable[21:22]
Ken concurs but focuses on Jake's fear, telling him to spend the next 30 days talking with trusted people (including Jenny) about his real financial fears and to confess he hasn't fully trusted her handling of money[22:11]
• Ken warns that if Jake stays fearful about money through his children's entire upbringing, they may adopt the same anxious view, instead of learning a balanced approach that includes making memories and having fun

Segment: Poverty, church outreach, and helping struggling families

Lynette's question about helping people who can't make ends meet

Lynette, outreach director at a church in a small town called Odell, explains they are starting a financial class and she runs the church food pantry, seeing many people who are not making ends meet and live paycheck to paycheck[24:30]
She asks for the number one piece of advice she can bring back to people who are struggling financially in her community[24:34]

Context: local economy, poverty, and ALICE

She notes the area has roughly 15% of residents at or below the poverty level and references "ALICE" households: Asset Limited, Income Constrained, meaning they have no assets and constrained income opportunities[25:14]
The community has some government housing but is also losing government funding, including rural transit for low-income people, which makes work access harder[25:26]

Separating middle-class lifestyle issues from true poverty

Rachel distinguishes between two groups: those in genuine poverty and those in the middle class whose expectations for lifestyle (larger homes, nicer finishes) exceed their income and lead to debt[25:49]
• She notes that many typical Ramsey callers fall into the second category, where credit card and car debt drive their paycheck-to-paycheck stress
For true poverty, she says it's a "much harder, bigger conversation" where increasing income is the central answer, but that path is complex and multi-faceted[26:41]

Macro-level economic challenges and potential paths

Ken calls Lynette's local situation a macroeconomic problem that feels micro because it's local, noting people in limited-income areas will have low quality of life unless they can increase income[27:14]
He suggests that helping some people may require guiding them onto a path toward better jobs, which could mean leaving the community for opportunities 30 miles away or beyond[27:26]
Lynette adds that many do not have reliable transportation, which makes commuting to the larger city 30 miles away difficult[29:17]
Ken frames the realistic message as a long, difficult journey: people may need to hustle, save for a car, and adopt a "covered wagon" mentality of moving to create a better life[28:26]

Budgeting and personal agency as starting points

George emphasizes helping each person create a zero-based budget to gain clarity, identify whether their core issue is income or debt, and stop fixating on external factors they can't control[30:23]
He says the budget acts like a financial mirror, showing whether someone needs more income or needs to focus on a debt snowball by making more, selling items, or side hustling[30:14]
He concludes that the person in the mirror is the "secret sauce" and the real solution, and Lynette's role is to help them believe that through classes and one-on-one support[30:33]

Segment: Producer James and fun personality questions

Introduction of longtime producer

The hosts introduce producer James, who has produced The Ramsey Show for 14 years, and note that in the control room they have the same emotional reactions to callers that the audience is now having live[31:59]
They joke that James and the crew will take Jake (from the earlier segment) out for drinks after the show because he was such a good sport[32:09]

Fishbowl of rapid-fire personal questions

James explains they have a fishbowl of fun questions for the hosts to answer rapidly, offering insight into their personalities[32:35]
Question: Are you the free spirit or the nerd in your marriage, and give an example[33:14]
• One host identifies as a free spirit who loves buying clothes and is very spontaneous, even needing a small purchase after budgeting just to "regulate" their nervous system
• Another host calls himself the nerd who uses a budgeting app, extra spreadsheets, and even gets bank transaction alerts by text and checks with his wife about each charge, joking that fraudsters might spend less than she does
Question: Best gift you've given or received[34:54]
• One host cites a large outdoor griddle as a favorite gift because he loves cooking for family and his kids' friends
• Another mentions a special ring received when a middle daughter was born and a creative sign for parents' lake house as a meaningful given gift
• George describes giving his wife tickets to see Backstreet Boys at the Sphere in Las Vegas as a "push present" after their second child, and jokes about the cost and his sensory issues about attending

Nostalgia and music discussion

Rachel shares that music from ages 10-16 triggers a unique kind of nostalgia because of how it's stored in the brain, explaining why concerts by childhood favorites can feel overwhelming and emotional[37:46]
• They trade examples of songs that spark nostalgia for them personally, noting that this phenomenon is backed by research about brain development and memory

Question: Wedding gift expectations on a budget

Laura's situation as a bridesmaid at a black-tie wedding

Laura from Logan Square, age 29 and in Baby Step 2 with only student loans left, is a bridesmaid in a friend's black-tie Chicago wedding[39:55]
She has attended the bachelorette party and bridal shower (without giving a gift yet), will attend a fancy rehearsal dinner and wedding with her boyfriend, and is unsure what an appropriate gift amount should be[40:03]

Debate over who should give what and how much

Laura's boyfriend thinks they should each give something since they are both attending all events; Laura initially imagines giving around $150 per person in cash but questions affordability and expectations[40:18]
Hosts question whether boyfriends are obligated to give gifts separately and whether bridesmaids should also be expected to give gifts after already spending a lot on participation[41:33]

Suggestions to balance etiquette, cost, and friendship

Rachel suggests a low-cost but sentimental gift-possibly something personalized and meaningful rather than an expensive registry item-especially since Laura has already spent over $1,000 on wedding-related costs[43:00]
Hosts debate etiquette notions like covering the plate cost with the cash gift and question whether such expectations are realistic or fair given the financial strain on friends[43:58]
They mention that being a single or younger friend today can be very expensive due to endless trips and events, and normalize pushing back against escalating expectations[44:57]

Game: Two Truths and a Lie - wild caller stories and "Kenuendos"

Explaining the game and recalling unusual calls

Ken introduces a game where he reads three statements supposedly from callers, and the audience guesses which one is the lie; two are real calls from the show, one is made up[46:58]
Real call examples include: a husband who thinks the government isn't real and stops paying debts; someone scammed out of $100,000 via online catfishing; a person wanting to put a payphone booth in their home for free phone service[47:03]
• One real caller's husband believed in conspiracy theories so deeply that he stopped paying taxes and debts, prompting the hosts to warn the wife she could go to jail if she doesn't comply with tax law

Other memorable real calls

They reference a caller whose wife maxed out a credit card at McDonald's (prompting math on how that is even possible), a house supposedly haunted by ghosts, and a parent asking about selling Taylor Swift tickets to pay off debt[49:42]
Another infamous real call involved a man who financed his wife's breast implants and then she cheated on him with his boss, making him, in Ken's words, a "double loser" on the deal[51:34]
They mention a real caller asking whether to prioritize a reverse vasectomy and another 14-year-old who had accumulated $21,000 in debt[51:45]

Internal "Kenuendos" and unintentional double meanings

Producer James explains they keep a private list of "Kenuendos"-unintentional innuendos Ken says on air-because he often doesn't realize how they sound until later[53:54]
They share an example where Ken told a caller's husband to take his wife down to the hardwood dealer and "make mama happy," not realizing the innuendo until the crew replayed it during a break[54:15]

Question: Book recommendations for people in Baby Steps 4-7

Ricky and Ruthie's request for reading ideas

Ricky from Skokie, with her daughter Ruthie (a big fan who read one host's book), asks for non-Ramsey book recommendations on lifestyle, relationships, or finance for people in Baby Steps 4-7[56:37]

Recommended financial and life-planning books

Rachel recommends "The Psychology of Money" for understanding money behavior and "Die With Zero" for its argument about using money during life for experiences, family help, and generosity instead of hoarding for a late inheritance[57:28]
• She notes she does not agree with everything in "Die With Zero" but appreciates its case for giving money to children earlier when they actually need it (e.g., down payments) and enjoying experiences while alive
Ken recommends "The Pursuit of Happiness" by Jeffrey Rosen, which traces how the Stoics and America's Founders understood happiness as growing in virtue, not acquiring more stuff-especially relevant for people now in "live like no one else" mode[58:56]
George suggests "The Five Types of Wealth" by Sahil Bloom, which expands focus from financial wealth to areas like relationships and health, and helped him realize his own life was "flat" outside finances[59:23]

Question: Feeling stagnant in Baby Steps 4-6

Ashley and Jim's sense of stalled progress

Ashley, recently moved to Milwaukee, and Jim share that they are in Baby Steps 4, 5, and 6 but feel stagnant and bored because every time they save extra money, an expense like plumbing or a car issue appears[1:00:21]
They quickly paid off debt and built their emergency fund, but now feel stuck and unable to consistently put extra toward their mortgage[1:01:06]

Normalizing the "boring middle" and offering perspective

Rachel explains that people often imagine Baby Step progress as a straight upward climb, but in reality life happens in waves: cars break, refrigerators fail, and unexpected travel arises[1:02:37]
She notes that from the millionaire study, Baby Steppers on average take about seven years to pay off their home, and other millionaires around 10 years, so Ashley and Jim should give themselves more runway and patience[1:02:04]

Practical tactics: goals, sinking funds, and audits

George compares the phase to being at cruising altitude on a flight: the initial takeoff is exciting, but the long middle can feel uneventful even though you're making progress[1:03:23]
He suggests making the mortgage payoff visual (e.g., rings or trackers) and setting a specific extra-principal goal each month (such as $500) before other chaos hits[1:04:58]
Ashley wonders if they have too many sinking funds; the hosts encourage a budget audit to see whether they're over-allocating to sinking funds in ways that delay mortgage progress[1:05:01]
They reveal Ashley and Jim have about $155,000 left on the mortgage, and note that crossing below the six-figure mark usually gives people a second wind of motivation[1:05:31]

Question: Life after the military - finding meaningful work

Amanda's identity shift after retirement from the Air Force

Amanda, recently retired after a 22-year career in the U.S. Air Force, shares that like many veterans, her identity was wrapped up in the uniform[1:06:27]
She asks how to find meaningful work on her own terms while differentiating herself from her military career[1:06:31]

Ken's exercise: inventorying talent and experience

Ken suggests a concrete exercise: on one side of a paper, list all talents and skills acquired in the Air Force; on the other, list the types of experience (e.g., crisis management, logistics) that used those skills[1:07:19]
• He says this helps Amanda see who she is apart from the Air Force and realize that her abilities and experiences are transferable to civilian roles
He notes employers highly respect veterans and that her narrative can highlight how her training and experience make her valuable outside the military[1:08:16]

Using tools and relationships to explore options

Ken recommends using an AI tool to input her skills and experiences and ask for potential roles outside the military, as well as taking his career assessment for further clarity[1:08:16]
He acknowledges that the unknown is paralyzing and compares it to driving in heavy rain: you naturally slow down or pull over until you can see; gaining clarity on options will reduce that fear[1:09:27]
His final advice is that once she sees possible roles, she should tell everyone she trusts what she's looking for, because many "great Americans" will want to help a veteran find her next step[1:09:48]

Group debt-free celebration and closing encouragement

Tallying recent debt freedom in the room

The hosts ask anyone who became debt-free in the last 12 months to stand and then go around the room collecting their total amounts of debt paid off[1:11:22]
Individual amounts range from a few thousand dollars to well over $200,000, including several six-figure payoffs[1:10:41]
After adding the numbers, George announces that in the last 12 months, people in the room have collectively paid off approximately $1,172,000 in debt[1:12:46]

Group debt-free scream

They then ask everyone in the room who is debt-free (consumer debt or fully Baby Step 7) to stand for a group debt-free scream[1:13:02]
Rachel sets up the traditional countdown, and the audience yells "We're debt-free!" together, recreating the classic Ramsey Show moment with a live crowd[1:14:32]

Surprise giveaway and final words

The hosts mention that on the show they usually give debt-free callers a year of their budgeting app, and then they surprise everyone in the audience by gifting access to the app for a year, in a tongue-in-cheek "Oprah moment"[1:14:53]
They close by thanking Chicago, affirming that the audience are the ones who did the hard work to gain financial peace, and reminding them they have changed their family trees[1:16:47]

Lessons Learned

Actionable insights and wisdom you can apply to your business, career, and personal life.

1

You cannot force family members to change their financial behavior; your power lies in setting clear, loving boundaries about whether you will lend or give them money.

Reflection Questions:

  • • Where in my life am I trying to change someone instead of clearly stating what I will and won't do?
  • • How could I communicate a firm but caring financial boundary to a family member who keeps asking for money?
  • • What specific support (information, tools, or one-time help) could I offer instead of becoming their ongoing lender?
2

There is a critical difference between enabling misbehavior and helping someone who is truly hurting, and your decisions about money should reflect that distinction.

Reflection Questions:

  • • Which current financial 'help' I'm giving might actually be enabling someone to avoid facing their own decisions?
  • • How can I better discern when a request for money is about chronic mismanagement versus a genuine emergency?
  • • What criteria could I set for myself so I know in advance when I will give, when I will loan, and when I will say no?
3

Money conflicts in relationships are often symptoms of deeper beliefs, fears, and past experiences, so resolving them requires understanding each other's money stories, not just adjusting the numbers.

Reflection Questions:

  • • What did I learn about money growing up that still shapes how I react to spending and saving today?
  • • How might my partner interpret my reactions to their spending or saving, and what fears might be underneath both of our behaviors?
  • • What regular conversation or budget ritual could we start that would build trust and shared visibility instead of side-eye and resentment?
4

In seasons that feel financially stagnant-like the middle Baby Steps or living in an economically depressed area-progress requires patience, intentional planning, and sometimes the courage to pursue new opportunities elsewhere.

Reflection Questions:

  • • Which part of my financial journey currently feels 'boring' or stuck, and what small measurable goal could reignite my motivation?
  • • If income is my main constraint, what realistic paths (skills, roles, or locations) could I explore to expand my earning potential over the next few years?
  • • Where can I tighten my plan (budgets, sinking funds, priorities) so that inevitable surprises don't completely derail my long-term goals?
5

When you go through a big identity shift, like leaving the military or changing careers, you can regain direction by clearly inventorying your skills and experiences and mapping them to roles that align with how you want to contribute now.

Reflection Questions:

  • • If I list out my top skills and the experiences where I've used them, what patterns emerge about the kind of work I'm built for?
  • • How could I reframe my past roles-in any field-as assets that make me valuable in new environments instead of anchors keeping me stuck?
  • • Who in my network could I share my ideal role description with so they can help connect me to opportunities I might not see on my own?

Episode Summary - Notes by Alex

The Ramsey Show Live From Chicago
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