Ramit Sethi of I Will Teach You To Be Rich talks to Cre and April, a couple of five years, aged 46 and 48. Cre lives a debt-averse life and has been methodically building her wealth.

April, on the other hand, earns more than twice Cre's income but struggles with significant debt and zero savings. They are at a crossroads, contemplating moving in together, but their conflicting approaches to money present a major hurdle.

Cre fears that April’s spending habits will lead to constant arguments and financial strain, especially with the prospect of marriage and inheriting April's substantial debt. April, however, doesn't see her spending as a problem, insisting she lives a good life and can always work more to cover expenses.

Ramit helps them uncover the generational patterns influencing their financial behaviors and challenges them to reconsider their current dynamic.

In this episode we uncover:

• How Cre and April act as "granny and child" during money conversations

• Why April feels micromanaged and hides purchases

• The emotional pressure April uses to get what she wants

• The significant disparity in their net worth despite April's higher income

• Why April initially doesn't see a problem with her spending habits

• The uncomfortable truth about April treating money like she's still poor

• How April's family history of money management influences her

• The shocking revelation about generational money patterns

• Why April's daughter is following a similar financial dynamic

• Ramit's direct challenge to April's “innocent doe” persona

• Cre's struggle to set clear financial boundaries

• How April reacts to Cre's direct financial expectations

• Ramit's step-by-step plan for April to tackle debt and build savings

Chapters:

(00:00:00) Introduction

(00:04:14) April's persistent questions about Cree's spending

(00:07:49) The "granny and child" roles in their money talks

(00:12:47) Why April fears marrying into debt

(00:13:46) The core of their financial disagreement

(00:23:05) A stark comparison of their financial numbers

(00:26:08) April's disconnect from her serious financial situation

(00:36:00) Cree’s secret side income and resourcefulness

(00:40:00) April’s luxury basement renovation with zero savings

(00:44:40) Unpacking April's extensive debt and spending habits

(00:48:28) Generational money patterns in April's family

(01:05:32) Cree's struggle to set clear financial boundaries

(01:10:09) The pitfalls of "walking on eggshells" in a relationship

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Ramit Sethi of I Will Teach You To Be Rich talks to Stephanie and Chris, an early-40s couple with three young children, two of whom have special needs. Chris is a professor, and Stephanie, an RN, has recently cut back her hours due to burnout.

Despite Chris’s confidence that “it’ll all work out,” their current financial situation is dire: 92% fixed costs, $544K in debt, and virtually no savings. Stephanie handles the books but feels dismissed when she raises concerns, while Chris struggles to listen and often interrupts.

Ramit helps them uncover hidden money scripts, gender dynamics, and a profound lack of communication that has kept them stuck in an "avalanche of inaction" for years. Can they finally align on a concrete plan and connect meaningfully about money?

In this episode we uncover:

• The stark reality of 92% fixed costs and zero investments

• How Chris’s “it’ll all work out” dismisses Stephanie’s worries

• How their money conversations always end in gridlock

• Why a wobbly kitchen sink reveals their deeper financial issues

• The surprising cost of their kids’ swim lessons

• How their combined salary still leaves them broke

• The emotional toll of their financial situation on Stephanie

• Chris's self-awareness about his "ignorant reassurer" role

• How their money "inaction" has cost them hundreds of thousands

• Why Stephanie feels unheard and Chris struggles to listen

• The plan to drastically cut fixed costs and tackle debt

• Why it’s time to stop making excuses and start taking action

Chapters:

(00:00:00) Introduction

(00:04:47) Their repetitive money conversation

(00:08:24) Chris's "natural reaction is to shut down"

(00:10:40) "He's a buzzkill"

(00:16:35) Breaking down their assets, debt, and net worth

(00:22:04) Stephanie's emotional confession

(00:24:00) Chris's desire to comfort without listening

(00:48:47) The cost of their inaction on investments

(00:56:56) How Chris can better support Stephanie

(01:11:00) What true financial partnership looks like

(01:12:00) Transforming their conscious spending plan

(01:21:00) A path to a 60% fixed cost future

This episode is brought to you by:

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Facet | As of the date of this recording, Facet is waiving the enrollment fee for new annual members, and for my audience, Facet is offering $300 into your brokerage account if you invest and maintain $5,000 within your first 90 days. Head to facet.com/ramit to learn more about which membership option is best for you. Offer expires March 31, 2026. #FacetAd  

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Connect with Ramit

• Get my new book, Money For Couples

• Get Money Coaching with Ramit 

• Download the Conscious Spending Plan

• Listen to my book—now on Audible

• Get my New York Times best-selling book

• Get my no-numbers journal

• Other episodes

• Instagram

• Twitter

• YouTube
If you and your partner have a money issue and you want my help, I occasionally select a couple to work with, free of charge. Apply for my help here: https://iwt.com/apply

Ramit Sethi of I Will Teach You To Be Rich talks to Melissa and Tony, a couple who immigrated from Mexico with big dreams and an even bigger work ethic. In less than a decade, they've built a net worth of nearly $900,000. But beneath the surface of their impressive paper wealth, they’re carrying almost $1 million in debt and are completely misaligned on their financial goals. With their second child due any day, Ramit helps them uncover the root of their money woes, from differing money styles to the profound impact of their upbringing. Can they finally get on the same page, create a financial system that works, and build a sustainable rich life?

In this episode we uncover:

• How Melissa and Tony built a nearly $900K net worth in 8 years

• The "rollercoaster" of their financial decision-making

• Why their credit card debt is actually due to real estate

• Tony’s “paycheck to paycheck” feeling with a $189k household income

• Melissa’s childhood money lessons from her dad, Mr. No

• How they navigate financial planning with a baby due this month

• Why they avoid combining their high incomes

• The cultural influences shaping their financial narratives

• What happens when Tony is “comfortable” and avoids change

• The deeper reasons behind their ongoing money disagreements

• Ramit’s advice on how to communicate about money effectively

• A surprising agreement that might change their future

Chapters:

(00:00:00) Introduction

(00:02:28) Their chaotic financial situation

(00:07:07) Melissa and Tony’s real estate struggles

(00:13:07) Melissa's real estate ambitions vs. Tony’s pessimism

(00:20:58) The cycles of making and losing money

(00:26:59) The ineffective communication about debt

(00:33:57) The danger of making emotional money decisions

(00:37:35) Diving deep into their income and debt

(00:46:01) Their unspoken rules about money and spending

(00:51:56) The painful truth behind being "house poor"

(01:00:43) Impact of childhood money lessons on their current finances

(01:10:29) The parent-child dynamic in their financial relationship

This episode is brought to you by:

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Gelt | Book a tax consultation with Gelt at https://joingelt.com/ramit. As a member of my community, you can skip the waitlist

Connect with Ramit

• Get my new book, Money For Couples

• Get Money Coaching with Ramit 

• Download the Conscious Spending Plan

• Listen to my book—now on Audible

• Get my New York Times best-selling book

• Get my no-numbers journal

• Other episodes

• Instagram

• Twitter

• YouTube

If you and your partner have a money issue and you want my help, I occasionally select a couple to work with, free of charge. Apply for my help here: https://iwt.com/apply

Ramit Sethi of I Will Teach You To Be Rich talks to Grace and James, a couple from Ireland, aged 38 and 37, who have been navigating immense challenges. James was diagnosed with cancer and underwent a year of treatment, while Grace managed a difficult pregnancy and maternity leave with their second child, an infant. Amidst the fear and grief, their household income took a significant hit, causing financial strain. Grace felt the burden of managing their finances, leading to guilt about James continuing to work during his illness. Despite these hardships, they’ve built a strong financial foundation with high savings and have managed to stay afloat. Ramit helps them explore their individual money psychologies, the impact of their upbringings, and how their shared experiences have shaped their financial outlook, revealing a story of resilience, unwavering teamwork, and an inspiring pursuit of a rich life.

In this episode we uncover:

• How Grace feels immense pressure to manage finances

• The emotional toll of James's cancer diagnosis

• Grace's hidden "mindless" spending under stress

• The Irish perspective on "mustn't grumble" about money

• James's childhood money messages and aversion to debt

• The surprising freedom found in small financial wins

• Grace's proactive approach to long-term financial planning

• The power of internal versus external locus of control

• How a shared money philosophy can emerge from conflict

• The importance of planning for the worst when at your best

• Their inspiring journey of overcoming adversity as a team

Chapters:

(00:00:00) Introduction

(00:05:13) Grace's guilt over James working during cancer

(00:12:32) Grace's "mindless purchases" and coping mechanisms

(00:15:55) The surprising reality of their financial stability

(00:30:03) Contrasting money philosophies: big spend vs. small treats

(00:33:45) Reviewing their Conscious Spending Plan and uncovering hidden wealth

(00:46:12) The impact of fluctuating income on their financial outlook

(00:55:00) Planning for the worst when they are at their best

(01:00:16) James's upbringing and the origins of his money anxiety

(01:11:10) Their "ice cream cone" fight and early money revelations

This episode is brought to you by:

Notion | Try Notion, now with Notion Agent, at https://notion.com/ramit

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Facet | As of the date of this recording, Facet is waiving their $250 enrollment fee for new annual members, and for my audience, Facet is offering $300 into your brokerage account if you invest and maintain $5,000 within your first 90 days. Head to facet.com/ramit to learn more about which membership option is best for you. Offer expires March 31, 2026. #FacetAd 

Shopify | Sign up for a $1 per month trial period at https://shopify.com/ramit

Connect with Ramit

• Get my new book, Money For Couples

• Get Money Coaching with Ramit 

• Download the Conscious Spending Plan

• Listen to my book—now on Audible

• Get my New York Times best-selling book

• Get my no-numbers journal

• Other episodes

• Instagram

• Twitter

• YouTube

If you and your partner have a money issue and you want my help, I occasionally select a couple to work with, free of charge. Apply for my help here: https://iwt.com/apply 

Ramit Sethi of I Will Teach You To Be Rich continues his discussion with Mike and Noel in part two of their financial deep dive. The couple, married for just 6 months, faces a daunting $244K in debt with zero savings, fueled by previous "guilt-free" spending and a shocking $170K windfall that disappeared. Despite their dire situation, major cuts to their fixed costs haven't happened yet. Ramit encourages Noel to reconsider her church tithing and find proactive ways to increase income, like driving for Uber. Can they shift their mindset from feeling deprived to purposeful sacrifice, anchor their spending to zero, and collaboratively create a sustainable financial future?

In this episode we uncover:

• Noel’s decision regarding her church tithing

• The power of incremental income, like Noel’s potential earnings from Uber

• Ramit’s "anchor to zero" framework for mindful spending

• How comparing current spending to past mistakes sabotages financial progress

• The importance of distinguishing between sacrifice and suffering

• Why making big changes with money is meant to be hard

• The potential for selling household items to boost savings and signal a "rebuilding phase"

• How a short-term financial plan can set them up for long-term success

• The opportunity to define their own timeline for debt repayment and savings

Chapters:

(00:00:00) Previously on money for couples

(00:02:09) How Noel's decided to approach tithing

(00:03:33) Why cutting subscriptions won't solve their problems

(00:03:49) Noel's plan to earn more money with Uber

(00:04:21) Ramit introduces the "anchor to zero" spending framework

(00:05:46) Mike and Noel reflect on the conversation

(00:07:11) Sacrifice vs. suffering: Reframing financial changes

(00:08:43) Why comparing to the past holds them back

(00:09:50) Noel's internal struggle with tithing

(00:10:34) Ramit presents a vision for their future

(00:11:15) The idea of selling household items to fund savings

(00:12:18) Ramit's proposal for their next steps and a follow-up

This episode is brought to you by:

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Connect with Ramit

• Get my new book, Money For Couples

• Get Money Coaching with Ramit 

• Download the Conscious Spending Plan

• Listen to my book—now on Audible

• Get my New York Times best-selling book

• Get my no-numbers journal

• Other episodes

• Instagram

• Twitter

• YouTube

If you and your partner have a money issue and you want my help, I occasionally select a couple to work with, free of charge. Apply for my help here: https://iwt.com/apply 

Ramit Sethi of I Will Teach You To Be Rich talks to Mike and Noel, a young couple who are both 34. They married just 6 months ago, but financial fights have become a daily occurrence, even after receiving a $170K windfall. Mike blames Noel for overspending, but admits they both struggle with money, while Noel views the windfall as "guilt-free" spending. With $244K in debt, zero savings, and 82% of their income going to fixed costs, Ramit helps them uncover the root of their money woes. Will they finally get on the same page, create a financial system that works, and learn to trust each other with money?

In this episode we uncover:

• How Mike’s money anxiety leads him to check his bank account 20 times a day

• The shocking truth about their $170K windfall

• Why Mike’s anxiety worsens when he makes more money

• The one money rule Mike and Noel both broke

• How Mike’s upbringing shaped his money habits

• Why Noel feels like she's "drowning" and has no control over their finances

• The spending categories that reveal their money psychology

• Why Mike's "money is mine" mentality is holding them back

• Noel’s struggle to “hand over her paycheck”

• The credit card debt that keeps piling up

• Ramit’s radical approach to cutting fixed costs

• The “Glade Plug-in” budget that explains everything

• Noel’s difficult decision about tithing and faith

• Why benchmarking against past mistakes is a recipe for disaster

• The truth about their approach to money

Chapters:

(00:00:00) “We just kinda like get whatever we want whenever we want it”

(00:07:02) “I was stressing more than ever before”

(00:14:04) The one money rule they both broke

(00:24:29) “You treat me like a child”

(00:32:39) Ramit identifies their “money leaks”

(00:39:34) “I don’t want to hand over my paycheck”

(00:47:30) “My goals are not being met”

(00:55:38) The “Glade Plug-in” budget

(01:00:03) “I do wanna have a Glade budget”

(01:06:50) How Mike’s upbringing shaped his money habits

(01:15:10) Ramit shares his radical advice

(01:21:10) Preview for part two

This episode is brought to you by:

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Connect with Ramit

• Get my new book, Money For Couples

• Get Money Coaching with Ramit 

• Download the Conscious Spending Plan

• Listen to my book—now on Audible

• Get my New York Times best-selling book

• Get my no-numbers journal

• Other episodes

• Instagram

• Twitter

• YouTube

If you and your partner have a money issue and you want my help, I occasionally select a couple to work with, free of charge. Apply for my help here: https://iwt.com/apply

Ramit Sethi of I Will Teach You To Be Rich talks to Natalie and Chris, married with two young kids and a net worth of $1.3 million. Despite their significant assets, money remains a constant source of conflict, especially when unexpected expenses arise. Chris tends to "freak out," emotionally withdrawing and becoming zombie-like, leaving Natalie feeling alone. This pattern, which Chris describes as "catastrophizing," has intensified since their kids' expenses piled up. 

Their therapist recommended they talk to Ramit, hoping to establish a financial game plan to prevent Chris's emotional collapses. Currently, 81% of their income goes to fixed costs, with 0% to savings, leading to a feeling of constant stress and no margin for error. Can Ramit help them create a financial system that provides peace of mind and allows Chris to process financial challenges with less distress?

In this episode we uncover:

• The unexpected source of Chris and Natalie’s referral to Ramit

• How large, unexpected expenses trigger Chris’s emotional “shutdown”

• Natalie’s experience of feeling isolated when Chris is financially stressed

• Why having a $1.3 million net worth doesn’t alleviate their financial anxiety

• The surprising reason for their elevated fixed costs and lack of savings 

• The emotional impact of feeling like there’s “nothing left over” at the end of the month 

• Chris’s pattern of “catastrophizing” and the fear of successive financial blows 

• The core question their therapist hopes Ramit can answer 

• How Chris’s upbringing influences his current financial anxieties 

• The challenges of discussing money when past traumas intertwine with current stresses

Chapters:

(00:00:00) “Your therapist...recommended that you speak to me”

(00:10:55) “Natalie, what’s your role in money?”

(00:25:43) The unexpected (and huge) financial blindspot

(00:36:18) Ramit discovers a massive amount of hidden money

(00:45:01) “You are financially set up for life”

(00:54:02) How "Red Bull wingsuit" leads to a Rich Life

(01:19:20) Finding an extra $1,360/month

(01:44:23) Natalie and Chris’s follow-up: “He’s at ease now”

This episode is brought to you by:

ZocDoc | Download the ZocDoc app for FREE at https://zocdoc.com/ramit then find and book a top-rated doctor today #sponsored 

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Facet | Facet is waiving their $250 enrollment fee for new annual members, and for my audience, Facet is offering $300 into your brokerage account if you invest and maintain $5,000 within your first 90 days. Head to facet.com/ramit to learn more about which membership option is best for you. Offer expires March 31, 2026. #FacetAd 

Connect with Ramit

• ⁠Get my new book, Money For Couples⁠

• ⁠Get Money Coaching with Ramit⁠

• ⁠Download the Conscious Spending Plan⁠

• ⁠Listen to my book—now on Audible⁠

• ⁠Get my New York Times best-selling book⁠

• ⁠Get my no-numbers journal⁠

• ⁠Other episodes⁠

• ⁠Instagram⁠

• ⁠Twitter⁠

• ⁠YouTube

If you and your partner have a money issue and you want my help, I occasionally select a couple to work with, free of charge. Apply for my help here: https://iwt.com/apply 

Two couples take the stage with a shared question—but very different financial realities: When is “enough” actually enough to move forward?

Finn and Luna built a successful pet-sitting business and now sit on hundreds of thousands of dollars—but with no clear plan for investing, homeownership, or the future. Meanwhile, Monica and Antonio earn a strong income, are completely debt-free, and yet feel paralyzed by fear as they juggle parenting, aging parents, and the possibility of purchasing a larger home.

In this live episode, Ramit digs into the tension between optimism and realism, abundance and anxiety. Together, they confront inherited money stories, decision paralysis, and what it really takes to turn income into confidence—so money stops being the thing that holds them back.

In this episode we uncover:

• Why having “hundreds of thousands of dollars” can still feel like total financial chaos without a system

• The emotional whiplash of going from paycheck-to-paycheck to sudden abundance

• How Finn and Luna’s optimism vs. realism split shows up in every conversation about housing, investing, and location

• Why crypto success without understanding risk creates false confidence

• The real reason Luna pulled money out of investments and parked it in cash

• How not knowing basic investing terms keeps progress stalled

• Finn’s fear that California homeownership is a ticking time bomb

• Monica and Antonio’s decision paralysis despite high income and zero debt

• How generational trauma, bankruptcies, and lost homes shaped Monica’s daily money anxiety

• Why Antonio believes earning more is the solution

• The financial and emotional toll of supporting aging parents while raising young children

• The hidden cost of being “responsible for everyone” and never prioritizing your own future

• The shift from reacting emotionally to money toward making deliberate, shared financial decisions

• What changes when money stops being mysterious

Chapters:

(00:00:00) “I’m a dreamer”—and he just wants a real plan

(00:25:32) What happens when the optimizer stops optimizing at home?

(00:33:01) “They gave up everything for us”

(00:46:33) “We make great money—but it doesn’t feel like enough”

(00:57:52) “I set the bar so high I can never win”

(01:04:37) Where are they now? Both couples’ follow-ups

This episode is brought to you by:

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LMNT | Get a free 8-count Sample Pack with any LMNT order at https://drinklmnt.com/RAMIT

Masterclass | Get up to 50% off Masterclass during the holiday season at https://masterclass.com/ramit

Links mentioned in this episode

• If you want help with your finances, join my Money Coaching program at https://iwt.com/moneycoaching

Connect with Ramit

• Get my new book, Money For Couples

• Get Money Coaching with Ramit

• Download the Conscious Spending Plan

• Listen to my book—now on Audible

• Get my New York Times best-selling book

• Get my no-numbers journal

• Other episodes

• Instagram

• Twitter

• YouTube

If you and your partner have a money issue and you want my help, I occasionally select a couple to work with, free of charge. Apply for my help here.

Cheryl (67) and Michael (69) have built rich, full lives: multiple careers, reinventions, and nearly 12 years of marriage. Yet when it comes to money, they feel stuck. They earn about $120,000 a year, have roughly $600,000 saved, and regularly book $10,000–$15,000 vacations focused on travel, family, and experiences. Then, almost immediately, panic sets in. With mostly separate finances, lingering trust issues from past decisions, and no clear retirement plan, they’re embarrassed to admit that they don’t actually know when (or if) they can retire. Cheryl wants clarity and confidence about the future, while Michael wrestles with fear, guilt, and uncertainty around spending and security. Can Ramit help them stop oscillating between YOLO travel and financial anxiety, and finally create a plan that lets them enjoy life without fear?

In this episode we uncover:

• Why Cheryl and Michael can easily book $10K–$15K vacations, then immediately panic

• How a “dream trip” exposes deeper confusion about what money they actually have access to

• How Michael losing $12,000 from an inheritance investment triggered feelings of betrayal

• Cheryl’s cancer survival and how living with mortality reshaped her urgency to travel, spend, and fully live now

• Michael’s discomfort with seeing money as “real” unless it’s physically accessible

• Why keeping finances mostly separate makes it nearly impossible to feel confident about retirement

• The emotional weight of being the higher earner

• How early family money stories still shape Michael’s decisions today

• Cheryl’s journey from Wall Street wealth to purpose-driven work

• Why spending in retirement feels scarier than earning ever did

• How “YOLO travel” and hyper-frugality coexist

• What their Conscious Spending Plan reveals about low fixed costs, high freedom, and misplaced fear

• Why having a financial advisor still didn’t give them clarity or peace of mind

Chapters:

(00:00:00) “I’m just doing this for Cheryl”

(00:23:13) Ramit breaks down their numbers

(00:45:23) “If we’re not on the same page, it’ll be an ugly retirement”

(01:08:29) “Am I worth it now—or am I still that kid asking permission?”

(01:10:01) “We never talked about money when we met”

(01:23:10) “If we retire now… will it feel like freedom—or fear?”

(01:36:38) Where are they now? Cheryl and Michael’s follow-ups

This episode is brought to you by:

ZocDoc | Download the ZocDoc app for FREE at https://zocdoc.com/ramit then find and book a top-rated doctor today #sponsored

Leesa | Go to https://leesa.com for 20% off mattresses PLUS get an extra $50 off with promo code RAMIT, exclusive for my listeners

Factor | Get 50% off plus free shipping on your first box at https://factormeals.com/ramit50OFF with code RAMIT50OFF

Facet | Facet is waiving their $250 enrollment fee for new annual members, and for my audience, Facet is offering $300 into your brokerage account if you invest and maintain $5,000 within your first 90 days. Head to https://facet.com/ramit to learn more about which membership option is best for you. Offer expires December 31, 2025.

Fabric by Gerber Life | Join the thousands of parents who trust Fabric to protect their family. Apply today in just minutes at https://meetfabric.com/ramit

Links mentioned in this episode

• If you want help with your finances, join my Money Coaching program at https://iwt.com/moneycoaching

Connect with Ramit

• Get my new book, Money For Couples

• Get Money Coaching with Ramit

• Download the Conscious Spending Plan

• Listen to my book—now on Audible

• Get my New York Times best-selling book

• Get my no-numbers journal

• Other episodes

• Instagram

• Twitter

• YouTube

If you and your partner have a money issue and you want my help, I occasionally select a couple to work with, free of charge. Apply for my help here.

Today, we’re revisiting one of our favorite Money For Couples episodes of the year.

Update: Romy and Travis recently shared an update on YouTube about where they are now. You can watch it here. 

Romy and Travis’s story struck a chord with listeners because it shows what really happens when a couple is earning good money…but operating with completely different expectations, habits, and fears around money.

This episode is a perfect example of how old patterns can quietly shape a relationship—and what it takes to break them. If you missed it the first time, or want a refresher, this is one of the most revealing conversations of the year.

In this episode:

• Why Travis believes he can always “go fishing” to make money

• How their childhoods shaped their attitudes toward money

• The emotional weight Romy carries as the only planner

• The story behind Romy’s secret UK savings

• Their unclear approach to buying property

• How disorganized thinking affects everything from taxes to tipping

• The risks of having no real emergency fund

• Why Travis’s role as the “reassurer” holds them back

• How Ramit helps them redefine generosity

• The first steps toward rebuilding trust

Chapters:

00:00 — “I tapped my card and it said insufficient funds”

09:23 — “I’m living the same financial life as my parents”

18:13 — Breaking down their numbers

38:14 — The weight of taking on the “man’s” role

52:48 — “I’ve been poor before—I’ll be poor again”

1:02:08 — Living on hope, not numbers

1:12:05 — “We’re doing this together”

1:28:56 — Where are they now? Romy & Travis

Connect with Ramit • Get my new book, Money For Couples • Get Money Coaching with Ramit  • Download the Conscious Spending Plan • Listen to my book—now on Audible • Get my New York Times best-selling book • Get my no-numbers journal • Other episodes • Instagram • Twitter • YouTube

If you and your partner have a money issue and you want my help, I occasionally select a couple to work with, free of charge. Apply for my help here.

Jamie (45) and Ryan (36) have been married for nearly a decade and share three kids, but their financial foundation was shaken when Ryan quit his high-paying finance job and cashed out his 401(k) without telling Jamie. Now earning far less, they’re still spending like nothing changed, running up credit card debt and ending each month wondering where the money went. Jamie, the higher earner, is anxious about retirement and trust after years of financial surprises, while Ryan avoids money conversations and struggles with insecurity. Layered on top are a 10-year age gap, deep past trauma, and very different visions of a Rich Life. Can Ramit help them rebuild trust, create a real plan, and finally start acting like partners instead of adversaries?

In this episode we uncover:

• The moment Jamie learned Ryan quit his high-paying job and cashed out his 401(k)

• How Ryan’s breaking point at work led to a “nuclear option” decision that shifted stress from the office straight into their marriage

Why earning nearly $300K still leaves them feeling broke

• The trust fallout from repeated unilateral decisions, including quitting jobs, cashing out retirement accounts, and impulsive purchases

• How Ryan’s spending on shoes, clothes, and even a classic car mirrors patterns he watched growing up

• Jamie’s role as the default financial manager

• The vacation-vs-things blame cycle that keeps them stuck spending instead of saving

• Why hiding money in a separate savings account felt like the only way Jamie could protect their future

• The uncomfortable truth behind their $13K emergency fund

• How calling their own spending “stupid” and “dumb” keeps them trapped in shame instead of change

• The emotional toll of living in constant financial vigilance while still spending freely on convenience and comfort

• How a failed $500 spending rule exposed their lack of shared systems

• The powerful influence of Midwestern money guilt, family secrecy, and conflicting childhood money messages

• Jamie’s past divorce and financial trauma

• The shift from adversaries to collaborators

Chapters:

(00:00:00) “We’ll just go our separate ways”

(00:18:56) Ramit breaks down their numbers

(00:40:49) “Smart people can make stupid choices”

(00:52:26) “Can we become a team again?”

(01:02:09) “Is this a Rich Life—or just a really long to-do list?”

(01:14:36) “You’ve turned dysfunction into permission”

(01:28:57) “I’m bitter that I have to pay it off”

(01:39:21) Where are they now? Jamie and Ryan’s follow-ups

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Links mentioned in this episode

• If you want help with your finances, join my Money Coaching program at https://iwt.com/moneycoaching

Connect with Ramit

• Get my new book, Money For Couples

• Get Money Coaching with Ramit

• Download the Conscious Spending Plan

• Listen to my book—now on Audible

• Get my New York Times best-selling book

• Get my no-numbers journal

• Other episodes

• Instagram

• Twitter

• YouTube

If you and your partner have a money issue and you want my help, I occasionally select a couple to work with, free of charge. Apply for my help here.