86. “I make $450,000/year from YouTube. My husband is ashamed he can’t match my success”

86. “I make $450,000/year from YouTube. My hu...

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241. “We invested our wedding money…in psychedelics”

Two couples 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, ...  Show more

240. “We book $10K vacations, then panic about money”

Cheryl (67) and Michael (69) have built rich, full lives: multiple careers, reinventions, and nearly 12 years of marriage. Yet when it comes to money, they feel stuck. They earn about $120,000 a year, have roughly $600,000 saved, and regularly book $10,000–$15,000 vacations focus ...  Show more

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