The Manager's Playbook - TopPodcast.com

Latest Episodes:

The Manager’s Playbook 040: Shawn Desman, Steve Zsirai & Chad Walsh - Drake’s Co-Sign, Fame, Sobriety, Social Media Strategy & Building a Comeback Team Sep 23, 2025

Show notes

Shawn Desman’s story is one of highs, lows, and a powerful comeback. From topping the charts to stepping away from music, Shawn opens up about the pressure of fame, battling depression, and finding sobriety. With Drake’s encouragement at an OVO event, he rediscovered his love for music and returned on his own terms.

Alongside managers Steve Zsirai and Chad Walsh, the conversation dives into the strategy behind rebuilding a career in today’s industry; from leveraging social media and data, to understanding touring, to balancing family life with success.

Packed with honesty, lessons, and laughs, this episode is for anyone who believes in resilience, reinvention, and the power of the right team.

Simply put, a conversation like this doesn't come cheap.

Watch the full episode on YouTube: ⁠⁠⁠⁠⁠⁠⁠⁠⁠https://www.youtube.com/@managersplaybook⁠⁠⁠⁠⁠⁠⁠⁠⁠

New episodes drop Tuesdays @ 10am ET

Inside the Playbook: Milana Lewis on What Artists Can Learn From Entrepreneurs Sep 22, 2025

Show notes

In this clip from The Manager’s Playbook, Mauricio Ruiz speaks with Milana Lewis (CEO of Stem) about her journey from having no background in music to becoming a leading entrepreneur in the industry.

Milana explains how building around clear vision and values, and using frameworks like EOS (Entrepreneurial Operating System), helped her align her company. She shares why the right team matters more than anything, how creating a culture that learns from failure drives growth, and why investing in employees is non-negotiable.

We also talk about the company retreat that immediately boosted performance, why naivety can be an advantage in innovation, and how borrowing ideas from other industries can break through the limits of traditional music business thinking.

This episode is a playbook for leadership, culture, and building companies that last.

A conversation like this doesn't come cheap.

Listen to the full episode here -

Spotify:

https://open.spotify.com/episode/7qj5aAUZJEh9bVIWWq596j?si=kORo9PheQ4G3mqg_t5X1PA

Watch the Episodes On Youtube: https://www.youtube.com/@managersplaybook

Inside the Playbook: Milana Lewis on What Makes an Artist Stand Out Sep 21, 2025

Show notes

In this clip from The Manager’s Playbook, Mauricio Ruiz sits down with Milana Lewis (CEO of Stem) to unpack the realities of artist development and partnerships in today’s music business.

Milana shares how artists can get noticed without relying solely on social media, why consistent storytelling is key, and the tough decisions behind who gets signed and when. She also dives into the challenges of timing, capacity, and staying true to your vision while finding the right partners.

We explore real-world examples, from artists like Frank Ocean and Chappell Roan, and draw parallels between the entrepreneurial journey of startups and the path of an artist testing and refining their craft.

This conversation is packed with insights for artists and managers navigating growth, making strategic decisions, and building long-term careers in music.

A conversation like this doesn't come cheap.

Listen to the full episode here -

Spotify:

https://open.spotify.com/episode/7qj5aAUZJEh9bVIWWq596j?si=kORo9PheQ4G3mqg_t5X1PA

Watch the Episodes On Youtube: https://www.youtube.com/@managersplaybook

Inside the Playbook: Milana Lewis on The Reality of Music Advances & Shelving Sep 19, 2025

Show notes

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 unpacks the new Concord partnership, designed to expand reach while keeping fairness and flexibility at the core.

The conversation doesn’t shy away from hard truths, including why major labels sometimes sign artists just to shelve them and control market share.

If you’re an artist, manager, or anyone navigating the music industry, this is a must-listen for understanding how to build smarter, more autonomous careers.

A conversation like this doesn't come cheap.

Listen to the full episode here -

Spotify:

https://open.spotify.com/episode/7qj5aAUZJEh9bVIWWq596j?si=kORo9PheQ4G3mqg_t5X1PA

Watch the Episodes On Youtube: https://www.youtube.com/@managersplaybook

Inside the Playbook: Milana Lewis on Why Music Contracts Are Broken Sep 18, 2025

Show notes

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 YouTube stars faced, and the legal roadblocks that eventually led to the creation of Tone.

This is a look at how smarter contracts and transparent royalty systems can reshape an artist’s career, and why fixing the “boring stuff” might be the most powerful move in music.

A conversation like this doesn't come cheap.

Listen to the full episode here -

Spotify:

https://open.spotify.com/episode/7qj5aAUZJEh9bVIWWq596j?si=kORo9PheQ4G3mqg_t5X1PA

Watch the Episodes On Youtube: https://www.youtube.com/@managersplaybook

The Manager’s Playbook 039: Milana Lewis – Artist Ownership, Royalties, Distribution vs. Delivery, Concord Partnership & The Future of Music Business Sep 16, 2025

Show notes

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/@managersplaybook⁠⁠⁠⁠⁠⁠⁠⁠

New episodes drop Tuesdays @ 10am ET

Inside the Playbook: Rich Castillo on Why Artists Get Dropped Too Quickly Sep 15, 2025

Show notes

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=XnodX5FcQIWW59yzWRaWfg

Watch the Episodes On Youtube: https://www.youtube.com/@managersplaybook

Inside the Playbook: Rich Castillo on How Failure Builds Resilience in the Music Industry Sep 14, 2025

Show notes

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=XnodX5FcQIWW59yzWRaWfg

Watch the Episodes On Youtube: https://www.youtube.com/@managersplaybook

Inside the Playbook: Rich Castillo on Why He Walked Away From the Major Label System Sep 12, 2025

Show notes

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=XnodX5FcQIWW59yzWRaWfg

Watch the Episodes On Youtube: https://www.youtube.com/@managersplaybook

Inside the Playbook: Rich Castillo on The Harsh Truth About A&R at Major Record Labels Sep 11, 2025

Show notes

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=XnodX5FcQIWW59yzWRaWfg

Watch the Episodes On Youtube: https://www.youtube.com/@managersplaybook