Jill chats with renowned hairstylist Orlando Pita to discuss his remarkable journey from self-taught Cuban immigrant to influential hair designer whose work has graced iconic Vogue covers and earned a place in the Smithsonian Design Triennial. Orlando opens up about his creative process and how his unconventional training freed him to innovate in hair styling, starting with cutting his family's hair and eventually working on high-profile shoots with Madonna, Beyoncé, and Lady Gaga.

They explore his pioneering approach to hair as visual art and examine the dynamics of collaborating with photographers and editors while navigating the shift from working with models to celebrity clients. Orlando shares stories from memorable shoots, including Madonna's 'Evita' Vogue cover and a unique collaboration with Irving Penn, while emphasizing how enthusiasm, gratitude, and continuous learning have driven his success. Orlando ends with some practical advice for aspiring hairstylists.

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Going Rogue is produced by Jill Demling and Maddie Kelly, who also serves as our social media director. Matty Rosenberg is the executive producer Be sure to follow Going Rogue on your favorite podcast platform.

Going Rogue is part of the Radio Free Rhinecliff media network.