The Manager's Playbook

In this clip from The Manager’s Playbook , Mauricio Ruiz sits down with Milana Lewis, CEO of Stem , to break down how Stem approaches artist partnerships and deal-making differently. Milana explains why Stem works on a project-by-project basis , how they manage capacity to protect quality, and how their simulator tool helps artists actually understand the financial reality of a deal. She also unpa...

In this clip from The Manager’s Playbook , Mauricio Ruiz sits down with Milana Lewis, CEO & Co-Founder of Stem , to break down one of the music industry’s biggest flaws: royalty accounting. Milana shares how Stem set out to simplify payments, give artists clarity on what they own, and make sure money flows where it should. She also explains the early challenges of distribution, the struggles Y...

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 do...

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...

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, wo...

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 , desig...

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 art...

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...

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. I...

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 an...

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...

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 r...

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 share...

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 effectiv...

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 humilit...

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...

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...

In episode 36 of The Manager’s Playbook , Mauricio Ruiz sits down with publicist and strategist Loren Medina , founder of Guerrera PR. From her start at Sony to building her own agency, Loren shares the unfiltered truth about navigating the music business, the importance of authenticity, and why values and strategy matter more than hype. She opens up about working with artists like J Noa and Jessi...

Music catalogs have become one of the hottest asset classes in the world. In this clip of The Manager’s Playbook , Dan Gonzalez and I unpack how catalogs are valued, why multiples matter, and what makes music such an attractive investment for hedge funds and capital allocators. From liquidity to long-term earnings, we explore why music is considered an uncorrelated asset, and what that means for a...

From Canadian grant writing to closing music business deals. In this clip of The Manager’s Playbook , I sit down with Dan Gonzalez who has navigated both worlds, and now helps artists protect their rights and grow sustainable careers. We discuss why some artists land grants while others don’t, how to simplify overly complex contracts, and the biggest pitfalls hiding in traditional label agreements...

Royalties are the lifeblood of an artist’s career but too often, they go uncollected. In this clip of The Manager’s Playbook , Dan Gonzalez breaks down how business managers protect artists and producers by auditing portfolios, identifying missing income, and navigating the complex world of rights and royalties. From masters and publishing to public performance, mechanicals, neighboring rights, an...

The role of a business manager has never been more important for artists. In this clip of The Manager’s Playbook , Dan Gonzalez breaks down how the job has evolved from simple bill payments and taxes to becoming the backbone of an artist’s entire financial structure. With music distribution decentralized and artists taking on more responsibilities than ever, the right business manager can mean the...

In this episode of The Manager’s Playbook , Mauricio Ruiz sits down with his own business manager, Dan Gonzalez , to uncover the financial backbone of an artist’s career. Dan explains why business managers are really the CFOs of the music industry and how the right systems around taxes, royalties, and catalog sales can be the difference between wealth and bankruptcy. From the hidden costs of advan...

Hit-Boy has leveled up, not just as a producer, but as a person. In this conversation, he talks about upgrading his lifestyle and workspace to unlock peak creativity, balancing fatherhood with a relentless creative output, and quietly building an empire that spans music, film scores, video games, and major brand partnerships. We dive into the freedom and challenges of independence, the role of mom...

Ownership isn’t just a buzzword. It’s the difference between building a career you control and one that controls you. In this clip, Hit-Boy, his manager Nima Nasseri, and I break down the mechanics of the modern music business through the lens of artists like Russ, who’ve built massive success independently. From the shift in revenue models and the evolving role of labels, to the rise of distribut...