The Manager's Playbook

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

Jared Cotter is the manager behind one of the biggest independent success stories of the decade.In this episode, we talk about how Shaboozey’s “A Bar Song (Tipsy)” made history, spending 19 weeks at #1 and tying the record set by Lil Nas X’s “Old Town Road”. But unlike most chart-toppers, this run happened completely independent, through Empire and his record label, American Dogwood.Jared shares what it’s really like to manage a superstar in real time: the chaos, the delegation, the importance of building the right team, and how to keep artists balanced when the pressure is nonstop. We also dive into the nuances of publishing deals, the unexpected opening in country music, and the launch of his 3AM Records label, a venture spotlighting global voices that deserve more recognition.This is more than a story about a hit song. It’s about leadership, trust, and what independence at scale really looks like in today’s music industry.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 episode of The Manager’s Playbook, publicist Loren Medina unpacks the evolving music industry and what independence really means for artists today. She challenges the myth that signing to a label guarantees success, pointing to examples like Bad Bunny to show how ownership and freedom have reshaped the game.Loren shares practical strategies for building PR from scratch, crafting effective pitches, and using storytelling as a tool to connect with audiences. She also highlights powerful redemption stories that prove adversity can become an artist’s greatest asset.Whether you’re an up-and-coming artist or a seasoned executive, this conversation is packed with insights on navigating the modern music business with purpose and strategy.Simply put, a conversation like this doesn't come cheap.Listen to the full episode here -Spotify:https://open.spotify.com/episode/4e0rjJHHyChVBTpuz4ahNh?si=2cXzGUGBSRu9fJy6b_7hhQWatch the Episodes On Youtube: https://www.youtube.com/@managersplaybook

In this clip of The Manager’s Playbook, publicist Loren Medina talks about what it’s really like to work with record labels from the outside. She explains why so many label teams lack long-term strategy, even for major artists, and how her structured approach sets her apart.Loren shares her experience promoting Jessie Reyez in both English and Latin markets, reflects on the importance of humility and authenticity in artists, and explains why values and alignment are non-negotiable in PR. She also opens up about refusing to work with entities that support harmful politics or social injustice, and why genuine human connection is still the foundation of great publicity.A conversation like this doesn't come cheap.Listen to the full episode here -Spotify:https://open.spotify.com/episode/4e0rjJHHyChVBTpuz4ahNh?si=2cXzGUGBSRu9fJy6b_7hhQWatch the Episodes On Youtube: https://www.youtube.com/@managersplaybook

In this clip of The Manager’s Playbook, publicist Loren Medina shares her journey from leaving Sony to launching Digital Girl in 2009, one of the first social media marketing companies in music. She reflects on navigating the early days of digital marketing, the importance of innovation and branding, and how those experiences shaped her move into PR.Loren also opens up about the realities of the industry, her work with major artists, and how her family heritage has influenced her path. The conversation closes with the story behind founding Guerrera PR and the values that continue to drive her work today.A conversation like this doesn't come cheap.Listen to the full episode here -Spotify:https://open.spotify.com/episode/4e0rjJHHyChVBTpuz4ahNh?si=2cXzGUGBSRu9fJy6b_7hhQWatch the Episodes On Youtube: https://www.youtube.com/@managersplaybook

In this clip of The Manager’s Playbook, publicist Loren Medina shares why passion is the foundation of every client relationship she takes on. From choosing artists based on authenticity, to navigating the evolving role of PR in the age of social media, Loren gives an unfiltered look at how storytelling drives careers forward.She breaks down her work with artists like Jessie Reyez, the strategy behind J Noa’s rise, and how moments like Tiny Desk can transform an artist’s path. Along the way, Loren discusses timing, dedication, and why the future of good PR is about much more than press releases; it’s about narrative, connection, and knowing when to strike.Simply put, a conversation like this doesn't come cheap.Listen to the full episode here -Spotify:https://open.spotify.com/episode/4e0rjJHHyChVBTpuz4ahNh?si=2cXzGUGBSRu9fJy6b_7hhQWatch the Episodes On Youtube: https://www.youtube.com/@managersplaybook