In this live-recorded episode, we’re talking about money, power, and style with Michaela Jaé Rodriguez. She’s well-known for her roles in projects like Pose, Loot, and Tick, Tick… Boom! and made history in 2022 as the first transgender actress to win a Golden Globe. Though Rodriguez is widely lauded for her acting performances, her first love was music, and in 2024, she released her debut album, 33. Today, we chat about why she’ll always spend money on herself, the shoes that are worth the pain, and the impact she hopes her career will have on the next generation. Plus, Rodriguez shares the two music industry icons she looks to for fashion inspiration.

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