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Freeway Ricky on His Worst Purchase Ever, Getting Ripped Off for $10M (Part 9)

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December 2, 2024

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Freeway Ricky Ross recounted his financial misstep, pouring $600,000 into the production of an Anita Baker album. Despite his significant investment, Ross never saw a return. He shared the backstory, revealing a deep connection to his childhood tennis mentor, Coach Larry Smith, and his son, Otis Smith, which paved the way for the deal. While Ross was immersing himself in the burgeoning hip-hop scene, an encounter with Smith led him to consider investing in the music industry. Influenced by industry veterans who assured him that hip-hop was just a fad, Ross pivoted towards the deal with Otis Smith instead of pursuing a career in hip-hop. Despite investing a considerable sum — particularly for the 1980s — there was no contract involved, highlighting Ross's naivety in the music business. Reflecting on his decision, Ross lamented that had he chosen differently, he might have become a pivotal figure in hip-hop.

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Full Interview PartFreeway Ricky RossAnita BakerCoach Larry SmithOtis SmithWhile Ross

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Freeway Ricky on His Worst Purchase Ever, Getting Ripped Off for $10M (Part 9) · Djvlad · Sentinel