The Manager's Playbook

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

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

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

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

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

Rich Castillo has spent nearly two decades inside the music industry, from Polydor, Sony, and EMI to Warner and now his own company, Lion Bear. In this episode of The Manager’s Playbook, Rich breaks down what A&R really means in 2025, why most artists lose urgency after signing, and how to navigate label politics without losing your vision.We also dive into artist development, the tug-of-war between data and instinct, and what separates a good executive from a great one. Packed with real stories and practical lessons, this is a must-listen for artists, managers, and executives who want to build lasting careers, not just moments.A conversation like this doesn't come cheap.Watch the full episode on YouTube: ⁠⁠⁠⁠⁠⁠⁠https://www.youtube.com/@managersplaybook⁠⁠⁠⁠⁠⁠⁠New episodes drop Tuesdays @ 10am ET

In this conversation, Jared Cotter and I dig into what it really takes to build a modern superstar.We talk about the rise of Shaboozey, how undeniable talent meets the right strategy, and the pivotal role management plays in turning momentum into long-term success. From building strong teams to navigating industry shifts, Jared shares the lessons that matter most for artists and managers alike.It’s a grounded look at resilience, teamwork, and the realities behind the spotlight.A conversation like this doesn't come cheap.Listen to the full episode here -Spotify:https://open.spotify.com/episode/7pUchYo0R1PoXmtKjZFud6?si=kods3ONJR0OPCDa3swoFVQWatch the Episodes On Youtube: https://www.youtube.com/@managersplaybook

In this conversation, Jared Cotter and I dig into the journey of breaking into country music and why authenticity always wins.We talk about how Shaboozey carved out his space in Nashville, the importance of diversity and representation, and how the genre is slowly opening its doors to new voices. Jared shares stories of resilience, community, and the impact of artists who are breaking barriers and creating opportunities for others.It’s a grounded look at what it takes to succeed, and stand out, in today’s country music landscape.A conversation like this doesn't come cheap.Listen to the full episode here -Spotify:https://open.spotify.com/episode/7pUchYo0R1PoXmtKjZFud6?si=kods3ONJR0OPCDa3swoFVQWatch the Episodes On Youtube: https://www.youtube.com/@managersplaybook

In this conversation, Jared Cotter and I dig into the world of music publishing and what it really takes to build a sustainable career.Jared shares his perspective as both a songwriter and a manager — from the smartest types of publishing deals to the importance of choosing the right partners. We talk about long-term strategy versus short-term checks, how to balance business with creativity, and the lessons that can make or break a career behind the scenes.If you’re an artist, songwriter, or manager in the making, this is essential listening.A conversation like this doesn't come cheap.Listen to the full episode here -Spotify:https://open.spotify.com/episode/7pUchYo0R1PoXmtKjZFud6?si=kods3ONJR0OPCDa3swoFVQWatch the Episodes On Youtube: https://www.youtube.com/@managersplaybook

In this conversation, Jared Cotter and I break down the making of Shaboozey’s “A Bar Song (Tipsy).”We talk about the creative spark, the key moments that shaped the record, and what it takes to recognize when you’ve got a hit on your hands. From the late-night studio energy to the strategy behind pushing it forward, this is a candid look at how an idea turned into one of the biggest independent records in recent history.If you care about songwriting, collaboration, or the craft of building timeless music, you’ll want to hear this one.Simply put, a conversation like this doesn't come cheap.Listen to the full episode here -Spotify:https://open.spotify.com/episode/7pUchYo0R1PoXmtKjZFud6?si=kods3ONJR0OPCDa3swoFVQWatch the Episodes On Youtube: https://www.youtube.com/@managersplaybook