In this episode ofThe Manager’s Playbook, we sit down with Gavin Sheppard, co-founder ofThe Remix Project, a cultural incubator that has helped launch the careers of countless artists and creatives. Gavin shares his journey from growing up with artist and journalist parents to building a program that bridges the gap between raw talent and the mainstream industry. He reflects on how his own struggles in the education system shaped his vision for creating spaces that foster creativity, mentorship, and opportunity.We explore the impact ofThe Remix Project, its passion-based approach, and the success stories of alumni like Amanda Parris and Tyrone Edwards. Gavin breaks down the importance of storytelling, navigating relationships, and the power of believing in others. Whether you're an artist, mentor, or someone interested in culture and community, this episode is packed with valuable lessons and inspiration.

In this episode, we sit down with Grammy nominated producer T-Minus to dive into his incredible journey through the music industry. From crafting hits for Drake to shaping the sound of some of the biggest tracks in hip-hop and R&B, T-Minus shares the story behind his rise to success. He talks about how he first met Drake, the creative process behind their iconic collaborations, and what it takes to thrive in the competitive world of music production. Whether you're an aspiring artist, producer, or just a fan of great music, this conversation is packed with insights, inspiration, and behind-the-scenes stories you won’t want to miss.

In this engaging conversation, Natalie Prospere, a trailblazer in the music industry and co-founder of Good Company Records, shares her inspiring transition from social work to managing Grammy-winning artists. She candidly discusses the complexities of artist advocacy, the emotional toll of her past career, and the cultural influences that shaped her values. Explore the challenges of navigating relationships and trust in the music world while discovering how genuine connections can redefine success in an often chaotic industry.

Jessie Reyez’s voice is unmistakable, but her journey to global recognition is a masterclass in grit, resilience, and relentless ambition. In this electrifying episode of The Manager's Playbook, hosted by Mauricio Ruiz, Jessie and her longtime manager Byron Wilson pull back the curtain on what it really takes to build a legacy in the music industry. From Jessie’s early days at Toronto’s Remix Project to creating a global buzz with tracks like Figures, this episode is packed with stories that define her rise. Jessie opens up about overcoming trust issues in an often ruthless industry, her unwavering dedication to understanding the business, and the sacrifices that come with chasing her dreams. Byron complements her narrative, revealing how strategic moves, teamwork, and a shared vision propelled Jessie’s career forward. Listeners will hear behind-the-scenes accounts of label bidding wars, pivotal collaborations with icons like Calvin Harris and Eminem, and the hustle required to perform back-to-back shows without losing steam. The trio discusses the power of saying “no” to comfort zones, the art of negotiation, and the importance of surrounding yourself with people who share your values and vision. Jessie’s candid reflections on work ethic, trust, and her drive to achieve goals like Grammy recognition make this episode a must-listen for anyone aspiring to make a mark in the creative world. Byron’s perspective as a manager adds depth, offering invaluable advice for navigating the industry with authenticity and strategy. This isn’t just a conversation about music—it’s a deep dive into the mindset and hustle required to turn raw talent into a global movement. If you’re an artist, manager, or just someone who loves a good underdog story, Jessie Reyez’s journey will inspire you to keep pushing, no matter the odds. 🎧 Tune in now for an unforgettable episode that blends honesty, insight, and inspiration from one of music’s most dynamic voices.

Director X is the embodiment of innovation, authenticity, and masterful storytelling. With a legacy built alongside some of the biggest names in music—think Drake, Rihanna, and Usher—Director X has reshaped the visual language of the music video industry. But his path to success wasn’t a straight shot to stardom. In this can’t-miss episode of The Manager's Playbook, hosted by Mauricio Ruiz, Director X opens up about his early days hustling to make a name for himself, the defining moments that tested his craft, and the relentless passion that pushed him to the top. From pioneering visuals that captured the essence of hip-hop and R&B to leading high-stakes production teams, Director X shares the raw truth about his journey. He dives into the art of building genuine connections with artists, his approach to creating visuals that resonate in the digital age, and the importance of a strong, authentic visual identity. Throughout, he provides invaluable advice for emerging directors and creatives, revealing the dedication and depth of collaboration that go into making standout projects. This isn’t just an episode about directing—it’s a blueprint for resilience, leadership, and the pursuit of artistic excellence. If you’re looking to get inspired by one of the industry’s most influential figures, this episode delivers unmatched insights from the master himself.

Byron Wilson’s journey from a small-town dreamer to managing global superstars like Jessie Reyez and SonReal is nothing short of inspiring. In this episode of The Manager’s Playbook, Byron opens up about the grind behind the glitz—sharing the challenges, hustle, and key relationships that helped him build a creative empire from the ground up. From booking DIY shows to navigating record labels, Byron’s deep insights into artist management and viral success, like with SonReal’s hit “Everywhere We Go,” will captivate anyone with aspirations in the music industry. Tune in to hear Byron’s strategies on artist development, the power of teamwork, and how smart decisions can turn indie dreams into global recognition. This episode is packed with gems for hustlers, creatives, and future managers alike. Byron Wilson on building global success, one hit at a time.

Cory Litwin is the MASTER of Getting into a Room! You cannot question his ability to help build and cultivate global superstars like Murda Beatz and Busta Rhymes. And that’s what you need and want from your manager. Especially in the beginning. In the world of artist management, connecting the dots and building relationships is key, and few do it as naturally as Cory Litwin. Known for his mastery of networking, Cory has cultivated an impressive career, from managing top-tier talent like Murda Beatz, Da Baby, and Busta Rhymes to organizing some of Toronto’s most iconic events. Starting at the University of Western Ontario, Cory’s journey has been defined by relentless hustle, deep connections, and a vision that always looks beyond the present moment. Today, we sit down with Cory to explore the art of making lasting impressions and how strategic partnerships have helped him excel at the highest levels of the music industry. He reflects on key moments that shaped his career, such as his ability to spot talent early and build it into global recognition. Beyond business, Cory speaks passionately about fostering creativity and supporting the next generation of artists, offering a rare glimpse into the world of a true industry connector. To all the hustlers and dreamers out there, this one's for you. A conversation like this doesn’t come cheap. The unstoppable Cory Litwin for ‘The Manager’s Playbook’ Podcast.

In this episode of The Manager's Playbook, host Mauricio Ruiz interviews the legendary Kardinal Offishall about his extensive career spanning 30 years as an artist and music executive. The discussion explores Kardinal's transition from artist to A&R executive, emphasizing the importance of human connections, authenticity, and global perspectives in the music industry. Kardinal shares behind-the-scenes stories, including early interactions with artists like Drake and Rihanna, and offers insights on identifying and nurturing raw talent. The episode sheds light on the complexities of music business contracts, the solitary nature of being a visionary, and the challenges faced when striving to make an artist a priority in a major label. Kardinal's enduring success is attributed to his genuine care for others and his commitment to staying true to himself. Ladies and gentleman, a conversation like this doesn't come cheap. Without further ado, Kardinal Offishall. 

Gordan Dillard, the powerhouse manager behind artists like Doja Cat, shares his remarkable journey in the music industry. He delves into his rise from an intern at Motown to becoming a vice president. Gordan discusses the importance of teamwork, work ethic, and authenticity, revealing how intuition fuels decision-making amidst challenges. With insights on pioneering management practices and the sacrifices required for success, he highlights the pivotal role of mentorship and support in navigating the ever-evolving music landscape.

In this episode of The Manager’s Playbook, host Mauricio Ruiz sits down with Shara Senderoff, a visionary at the crossroads of entertainment, technology, and innovation. From selling a script to Steven Spielberg at just 20 years old to co-founding a fund Raised In Space with Zach Katz and Scooter Braun, Shara's journey is nothing short of extraordinary. Join us as Shara shares her transition from film and TV to the music industry, her groundbreaking work in blockchain and AI, and her unique approach to the Blue Ocean Strategy. She also dives into the power of meditation, the importance of curiosity, and the entrepreneurial spirit that fuels her success. This episode is packed with insights on technology, music, personal growth, and running multiple businesses while seemingly bending time. Ladies and gentlemen, a conversation like this doesn’t come cheap. Without further ado, Shara Senderoff.