87. “We’re in $400,000 of debt, but we can’t say no to our kids”
Kenna and Ryan are 36 and 45. Up until recently, Ryan worked and Kenna stayed home with their kids. Now, with that earning dynamic flipped, they’re facing new challenges with how they spend and save—e...
21 Mar 20231h 26min
86. “I make $450,000/year from YouTube. My husband is ashamed he can’t match my success”
Darby and Kirsty, 27 and 25, are professional YouTubers. While Kirsty’s art tutorial channel explodes in profitability, Darby’s efforts lag behind in viewership and earnings, creating a stark contrast...
14 Mar 20231h 26min
85. “I thought she was going to die, so we spent all our money. Now we’re broke”
Asha and Matt are in their mid 30s. They bring a totally unique situation to the show today. A few years ago, Asha needed a second open-heart surgery—and an emergency appendectomy. She was told she mi...
7 Mar 20231h 30min
84. “We spend 98% of what we make—but we refuse to change our lifestyle”
Kristine is 32 and Thomas is 35. They’re raising three children in the Midwest. They love their jobs, are happy with their incomes, and just upgraded to a third, much larger, home. Everything is good–...
28 Feb 20231h 28min
83. “I grew up on food stamps. At 24, I’m about to get paid $215,000 per year”
Megan and Nyles are in their twenties and on a great trajectory with their money. She graduates from law school this year—sending her income from $0 to $215,000 overnight. But they’re both haunted by ...
21 Feb 20231h 23min
82. “I’m in $20,000 of debt and she pays for everything. What’s the problem?”
Melody and David are 39 and 45. They manage a picturesque multi-unit property which creates a unique money dynamic. David works as the property manager and has his own side business, but doesn’t pay a...
14 Feb 20231h 24min
81. “We’re broke—but $55,000 private school tuition is a non-negotiable” (Part 2)
In part two of our revealing conversation with Sarah and Kevin, we offer solutions for their serious debt accumulation problem and grapple with the hard truth about their biggest non-negotiable expens...
7 Feb 20231h 10min
80. “If I add any more to our $50,000 credit card debt, he will ask for a divorce” (Part 1)
Sarah and Kevin are 38 and 42. They sold their home to pay off $130k in debt, only to dig themselves another $55k hole, six months later. Sarah is worried that if she doesn’t stop her credit card spen...
31 Jan 20231h 1min
