Taylor (29) is a high-earning dentist with a strict savings plan and deep-rooted fears about financial instability. Hayden (25) earns $24K a year, has a history of gambling and financial dishonesty, and struggles with budgeting. They live together, but their vastly different money philosophies leave Taylor questioning whether marriage is possible. With trust ... Show More
Oct 7
229. “I’m almost 50 and have nothing to show for my life”
Christine (47) and Thad (57) have been together for more than six years, but instead of building wealth, they’re buried under nearly $340,000 of debt. Christine, the self-appointed “CFO,” is exhausted from tracking every bill, while Thad avoids the details and spends freely. Thei ... Show More
1h 44m
Sep 30
228. “I’m 30, broke, and tired of budgeting”
Kristen (30) and Josh (36) married just last year, but their honeymoon phase is buried under $40,000 of debt and a sense of being “trapped.” Kristen is meticulous, tracking every dollar and carrying deep guilt around spending—even on herself. Josh, meanwhile, shrugs off the stres ... Show More
1h 38m
Sep 23
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 earnin ... Show More
1h 20m
Sep 11
Money Is Emotional: Values-Based Spending, Social Pressure, and Financial Confidence with Jack Howard (of Ally Bank)
Financial wellness isn’t just math—it’s mindset. Today, Jack Howard, strategic program and communications lead at Ally and secretary of the Ally Charitable Foundation, joins me to unpack money psychology, values-based spending, and why “financial confidence” has very little to do ... Show More
50m 7s
Oct 6
Financial Expert: Passive Income Is A Scam! Post-Traumatic Broke Syndrome Is Controlling Millions!
Morgan Housel, global expert on personal finance, shares powerful lessons on Warren Buffett’s hidden struggles, Elon Musk’s sacrifices, money trauma and financial habits, how to invest wisely, and the psychology behind saving, spending, and success. Morgan Housel is a partner at ... Show More
2h 8m