227. “We bought our dream house. Now we’re drowning”

Jason (38) and Katie (36) thought buying their dream home in Minnesota would be the start of a new chapter. Instead, they’re buried in debt, daycare bills, and the pressure of raising a new baby while working demanding creative jobs in an industry threatened by AI. Despite earning $246,000 a year, they’ve been trapped in a decade-long debt cycle, and every dollar is already spoken for. With $30,000 in debt left to go and no clear plan for what comes next, can they finally break free of survival mode and build the life they truly want together? In this episode we uncover: • How Jason and Katie’s “dream home” quickly became a financial trap • Why their money talks happen every single day—and why that constant communication leaves them exhausted • The pattern of paying off debt, only to fall right back into it • The hidden costs of homeownership • Jason’s obsession with “cashflow”—and why Ramit calls it a red flag that blinds them to the bigger picture • How Katie’s childhood les...