The Manager’s Playbook 039: Milana Lewis – Artist Ownership, Royalties, Distribution vs. Delivery, Concord Partnership & The Future of Music Business
In episode 39 of The Manager’s Playbook, Mauricio Ruiz sits down with Milana Lewis, co-founder and CEO of STEM, to unpack the realities of today’s music business.Milana explains why royalty accounting is still one of the industry’s biggest problems, why so many artists don’t know what they own or when they’ll get paid, and how that lack of clarity gets exploited in bad deals. She also breaks down the difference between independence and autonomy, the role of distribution vs. delivery, and what artists really need to cut through the noise.The conversation also dives into STEM’s new partnership with Concord, the evolution of Tone, and how technology, storytelling, and team-building are reshaping the future of music.If you’re an artist, manager, or anyone building a career in the music business, this episode is packed with insights to help you navigate the chaos.A conversation like this doesn't come cheap.Watch the full episode on YouTube: https://www.youtube.com/@managersplaybookNew episodes drop Tuesdays @ 10am ET
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Inside the Playbook: Rich Castillo on Why Artists Get Dropped Too Quickly
In this clip from The Manager’s Playbook, Rich Castillo pulls back the curtain on the realities of A&R and the inner workings of major labels. He explains how decisions actually get made inside the hierarchy, the role data plays in scouting talent, and why live shows still matter in discovering artists.We also explore how young A&R execs can grow within the system, the pressure IPOs put on creativity, and the constant balancing act between taking risks and chasing profitability.Packed with real stories and practical advice, this conversation is a must-listen for artists, managers, and aspiring executives who want to understand how today’s music industry really works.A conversation like this doesn't come cheap.Listen to the full episode here -Spotify:https://open.spotify.com/episode/2XcP1p1vnPO2a5DHDnJzVO?si=XnodX5FcQIWW59yzWRaWfgWatch the Episodes On Youtube: https://www.youtube.com/@managersplaybook
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Inside the Playbook: Rich Castillo on How Failure Builds Resilience in the Music Industry
In this clip from The Manager’s Playbook, Rich Castillo dives into the rise of UK rap culture and its global impact. He explains how London’s melting pot of influences creates a distinct sound, why regional identity is crucial for artists, and how UK rap compares to the U.S. scene.Rich also shares his personal journey, from early career setbacks and getting fired to thriving as an executive, working with emerging artists like Liverpool rapper Cast, and building successful teams. Along the way, he highlights lessons in resilience, financial realities, and the challenges of scaling in the music business.This conversation is about more than music. It’s about culture, survival, and building a career with real substance.A conversation like this doesn't come cheap.Listen to the full episode here -Spotify:https://open.spotify.com/episode/2XcP1p1vnPO2a5DHDnJzVO?si=XnodX5FcQIWW59yzWRaWfgWatch the Episodes On Youtube: https://www.youtube.com/@managersplaybook
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20:35
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Inside the Playbook: Rich Castillo on Why He Walked Away From the Major Label System
In this clip from The Manager’s Playbook, Rich Castillo reflects on his move from the major label system to launching his own independent label, Lion Bear. He shares why legacy and independence matter more than comfort, what inspired him to take control of his career, and how he’s thinking about the next chapter of the music business.Rich also introduces his new podcast, The Hot Seat, designed to share insight from high-level executives and inspire the next generation. His first guest: UK music veteran Trenton Harris Lewis.This is a conversation about ownership, perspective, and building something that lasts.A conversation like this doesn't come cheap.Listen to the full episode here -Spotify:https://open.spotify.com/episode/2XcP1p1vnPO2a5DHDnJzVO?si=XnodX5FcQIWW59yzWRaWfgWatch the Episodes On Youtube: https://www.youtube.com/@managersplaybook
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12:19
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Inside the Playbook: Rich Castillo on The Harsh Truth About A&R at Major Record Labels
In this clip from The Manager’s Playbook, Rich Castillo breaks down what the role of A&R really looks like in 2025. From identifying and developing talent to balancing data, instinct, and marketing, Rich shares how decisions actually get made inside labels.We also discuss the traits that separate great A&R executives from the rest, the misconceptions around the job, and the pitfalls artists face when signing to majors.Whether you’re an artist, manager, or aspiring exec, this conversation delivers real-world insight into the music industry today.A conversation like this doesn't come cheap.Listen to the full episode here -Spotify:https://open.spotify.com/episode/2XcP1p1vnPO2a5DHDnJzVO?si=XnodX5FcQIWW59yzWRaWfgWatch the Episodes On Youtube: https://www.youtube.com/@managersplaybook
Hosted by Mauricio Ruiz, a music industry executive of 15 years, The Manager's Playbook is your essential podcast for insights into the music industry. Whether you're an artist, aspiring manager, music industry professional, or just passionate about the behind-the-scenes of the music business, this podcast is for you. Mauricio brings you in-depth interviews with top artist managers, entertainment lawyers, and other industry execs. Each episode is packed with valuable tips, real-world experiences, and expert advice to help you navigate the complexities of the music business.
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