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

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

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

Jaksot(261)

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 Helmi 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 Helmi 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 Helmi 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 Helmi 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 Helmi 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 Helmi 8min

Inside the Playbook: Sickick on What Good Management Actually Feels Like

Inside the Playbook: Sickick on What Good Management Actually Feels Like

In the music business, careers don’t usually break because of bad songs. They break because team dynamics fail.In this clip from The Manager’s Playbook, Sickick breaks down what healthy artist managem...

8 Helmi 5min

Inside the Playbook: Sickick on The Truth About Reinventing Yourself as an Artist

Inside the Playbook: Sickick on The Truth About Reinventing Yourself as an Artist

TikTok can give you attention fast. It can also box you in even faster.In this clip from The Manager’s Playbook, Sickick breaks down the real arc behind the “TikTok DJ” label, how remix momentum and a...

7 Helmi 15min

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