“I've been homeless before… I'm terrified to spend money”

Ramit Sethi of I Will Teach You To Be Rich talks to Jennifer (37) and Steve (41). They’ve been dating for over five years, but they’ve never spent more than $100 on a shared purchase. Jennifer is a self-made business owner with a clear vision for the future, while Steve is cautious, financially conservative, and still haunted by a turbulent past that included losing both parents and living out of his car. Despite a solid income and nearly $200,000 in savings, Steve can’t shake the fear of financial collapse. Jennifer, meanwhile, is growing resentful. She wants a partner who dreams big and makes bold moves with her—not someone who second-guesses a $10 purchase. Can they confront the past, align on a shared vision for their future, and finally start acting like teammates? 💡 RAMIT’S PODCAST NEWSLETTER * I share new ways to think about money every Saturday. Get the emails here: https://iwt.com/podcastnewsletter-yt 🙌 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-youtube * Optimize your credit cards with the 1st chapter of my book: https://iwt.com/chapter1-youtube * Join my Money Coaching program for monthly help: https://iwt.com/moneycoaching-youtube * 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/ 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