Inside the Playbook: Chris Taylor on His Biggest Mistake with Last Gang Records

Chris Taylor’s path has been anything but linear: lawyer, label founder, and music executive with a global footprint.

In this clip of The Manager’s Playbook, he shares how he scaled a thriving legal practice while launching Last Gang Records, balancing the demands of both worlds, and navigating the breakthrough moments that shaped his career. From the strategies he used to build and fund his firm, to the lessons learned from working with diverse legal talent, to the ripple effect of representing Drake on the Canadian music scene, Chris pulls back the curtain on the business moves that matter.

We also dive into his leap to Entertainment One (eOne), the negotiations that brought him there, and the leadership lessons he absorbed from founder Darren Troop; insights on patience, discipline, and vision that apply far beyond music.

It’s a candid look at the intersection of law, music, and business growth, told by someone who’s mastered all three.

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

Listen to the full episode here -

Spotify:

https://open.spotify.com/episode/2m8tNzMZHx1LpZtC0i9eNh?si=5XO54H5nQmiRzPOCW06jZw

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