Ramit Sethi of I Will Teach You To Be Rich talks to two couples who 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 life 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 💡 RAMIT’S PODCAST NEWSLETTER * I share new ways to think about money every Saturday. Get the emails here: https://iwt.com/podcastnewsletter 🙌 GET HELP FROM RAMIT SETHI * Order my new book: Money for Couples: https://iwt.com/moneyforcouples * Take control of your money with the Conscious Spending Plan: https://iwt.com/csp * Optimize your credit cards with the 1st chapter of my book: https://iwt.com/chapter1-pod * Join my Money Coaching program for monthly help: https://iwt.com/moneycoaching * Listen to my book—now on Audible: https://amzn.to/48zko28 🤳 CONNECT WITH RAMIT SETHI * Instagram: https://www.instagram.com/ramit/ * X: https://twitter.com/ramit ✅ SUBSCRIBE SO YOU DON’T MISS ANY EPISODES https://youtube.com/user/ramitsethi/featured/ THIS EPISODE IS BROUGHT TO YOU BY Bilt | Join the loyalty program for renters at https://joinbilt.com/ramit Shopify | Sign up for a $1 per month trial period at https://shopify.com/ramit 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 Gelt | Book a tax consultation with Gelt at https://joingelt.com/ramit. As a member of my community, you can skip the waitlist 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 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