In episode 4 of Won of One: A PLLRS Podcast, Steven “Steve-O” Carless takes listeners on a powerful journey through his evolution from a first-generation Jamaican-American music lover to one of the most influential executives in hip-hop. Reflecting on early experiences at Star Trak Entertainment, where he learned the value of opportunity and purpose, Carless shares how pivotal connections, from Pharrell Williams to Jay Z, Benny Pough, and Nipsey Hussle, shaped his approach to leadership and legacy. He opens up about the lessons behind setbacks, the art of relationship-building, and the cultural shifts he witnessed across Def Jam and Atlantic Records along the way. From helping launch Jay-Z’s comeback and earning an executive producer credit on "Brown Skin Girl" with Beyoncé to serving as a mentor and friend to Nipsey Hussle, Carless reveals the mindset behind staying grounded while shaping history, and why gratitude remains his greatest success.

About Today’s Guest

Steven “Steve-O” Carless is a visionary music executive and entrepreneur whose influence spans across A&R, artist development, and brand strategy. Carless has played a pivotal role in shaping the careers of some of today’s most impactful artists, from Nipsey Hussle to Polo G. With a career rooted in authenticity and cultural integrity, Steve-O brings a deep understanding of how art, business, and community intersect. On Episode 4 of Won of One: A PLLRS Podcast, he shares rare insight into leadership, legacy, and what it truly means to build something that lasts beyond the music.

Key Points from this Episode:

• 0:00 Welcome back to Won of One: A PLLRS Podcast with today’s guest, Steven “Steve-O” Carless

• 1:43 Carless on his upbringing as a first-generation Jamaican-American and music as a constant

• 3:00 From listening to music with his parents, to starting at Star Trak Entertainment

• 11:50 Why Star Trak over Sony Urban Music?

• 14:00 How learning about the music industry as a way to make opportunities for others led to finding purpose

• 18:09 Balancing a career in the music industry with the stress of external relationships

• 23:00 The Pharell experience and learning to network in the music business

• 24:52 Getting fired from Star Trak, working with Cipha Sounds, and moving to Def Jam

• 30:40 Connecting with Jay Z and meeting one of his first mentors, Benny Pough, at Def Jam

• 36:19 Connecting with Nipsey Hussle, becoming best friends, bonding over books, and lessons learned from Crenshaw, the $100 mixtape

• 56:15 Becoming an A&R at Atlantic Records, working with Nipsey Hussle

• 1:04:12 Reconnecting with Jeezy at Atlantic through A&R and becoming the president of his label

• 1:10:47 No I.D. recruits Steve-O to come back to Def Jam as an A&R after successful projects with Jeezy and YG, while finishing Nipsey’s album, Victory Lap

• 1:13:47 How knowing all of the roles inside the record label contributed to Steve’s success

• 1:14:06 Game-changing moments that Steve Carless was responsible for, and being part of Jay Z’s American Gangster video trailer going viral

• 1:17:54 Working with Beyonce and how Brown Skin Girl landed on The Lion King: The Gift, with Steve Carless named as an executive producer

• 1:29:00 On being a pillar to monumental moments and the power of gratitude

Mentioned on the Show

Join the Conversation: 

🏛️ Watch more on YouTube: https://www.youtube.com/@thePLLRS

🏛️ Follow us on Instagram: https://www.instagram.com/thepllrs/

🏛️ Follow us on TikTok: https://www.tiktok.com/@thepllrs

🏛️ PLLRS Press and more: https://linktr.ee/ThePLLRS

🔊 Listen on Spotify: https://creators.spotify.com/pod/profile/thepllrs/

🔊 Listen on Apple: https://podcasts.apple.com/us/podcast/won-of-one-a-pllrs-podcast/id1840643899

✉️ For Business Inquiries, email: [email protected]