This week on ITMOJT, Jax is joined by pop-rock legend Ryan Cabrera. They reminisce about 2000s music, tour life, CD booklets, and Christmas trees that stay up all year. Ryan opens up about his time on reality TV, shares wild backstage stories (yes, even one involving Prince Harry), and talks fatherhood, social media pressure, and how a tabloid rumor led him to his now-wife.

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This week, Jax returns with his sister Jenny for Part 2 of their brutally honest sibling sit-down. Jenny doesn’t hold back as they explore the roots of Jax’s behavior, his struggles with self-worth, and whether real change is possible. Together, they revisit childhood memories, reflect on family dynamics, and open up about mental health—while Jenny shares what it’s really been like to watch Jax’s rise, fall, and everything in between.

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This week on ITMOJT, Jax invites his sister Jenny onto the podcast for a raw conversation about family, fame, and everything in between. From emotional stories about their Michigan roots and Jenny’s dream lake house, to brutally honest reflections on Jax’s impulsiveness, need for validation, and the toll of reality TV life — nothing is off-limits.

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