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

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

Episoder(271)

Inside the Playbook: Paris Cole on How to Build a Global Artist

Inside the Playbook: Paris Cole on How to Build a Global Artist

In this clip from The Manager’s Playbook, Paris Cole breaks down artist development through branding, styling, and creative direction and why audiences can instantly tell when an artist is “trying too...

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The Manager’s Playbook 055: Paris Cole - Artist Development, Brand Vision, Styling as Strategy, Fan Engagement & Building From Scratch

The Manager’s Playbook 055: Paris Cole - Artist Development, Brand Vision, Styling as Strategy, Fan Engagement & Building From Scratch

Paris Cole is a true music industry multi-hyphenate, artist manager, creative director, and stylist, and in this episode of The Manager’s Playbook, she breaks down what it actually takes to develop ar...

18 Feb 2h 9min

Inside the Playbook: SonReal on How to Tour Without Going Broke

Inside the Playbook: SonReal on How to Tour Without Going Broke

Touring isn’t just stage time. It’s a business model.In this clip, SonReal breaks down how live shows became one of the most important parts of his career, not only as performance craft, but as a real...

16 Feb 11min

Inside the Playbook: SonReal on How Independent Artists Can Make Real Money

Inside the Playbook: SonReal on How Independent Artists Can Make Real Money

The biggest advantage an independent artist has right now is simple: there are no rules.In this clip, SonReal breaks down what happens when you stop waiting on label timelines and start operating like...

15 Feb 13min

Inside the Playbook: SonReal on How Content Actually Grows Music

Inside the Playbook: SonReal on How Content Actually Grows Music

The “mysterious artist” era worked when the music business was built around blockbuster music videos and gatekeepers. Today it’s algorithmic, short-form, and driven by consistent distribution.In this ...

14 Feb 13min

 Inside the Playbook: SonReal on The Strategy Behind Viral Artists

Inside the Playbook: SonReal on The Strategy Behind Viral Artists

Most independent artists don’t struggle because they can’t make music fast.They struggle because they can’t make the pace financially sustainable.In this clip, SonReal breaks down a modern independent...

13 Feb 13min

The Manager’s Playbook 054: SonReal - Independent Artist Strategy, Owning Your Masters, 2-Week Release Schedule, Content Systems & Touring Profitably

The Manager’s Playbook 054: SonReal - Independent Artist Strategy, Owning Your Masters, 2-Week Release Schedule, Content Systems & Touring Profitably

There’s a whole middle class in the music industry.Artists who aren’t household names, aren’t living off viral moments, and aren’t waiting on label permission, yet they’re making real money, building ...

10 Feb 1h 50min

Inside the Playbook: Sickick on Reinventing His Sound to Build Longevity

Inside the Playbook: Sickick on Reinventing His Sound to Build Longevity

TikTok can give you momentum. The real question is whether you can turn that momentum into a career with identity.In this clip from The Manager’s Playbook, Sickick breaks down his evolution from dark ...

9 Feb 8min

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