Welcome to The Manager’s Playbook, my personal newsletter where I share insights from Music Executives and Artists for aspiring and emerging music managers, executives and artists on how to navigate the music industry. This newsletter is brought to you by Mauricio Ruiz.

Ruiz’s Note:

This note comes a day later than I was hoping.

The catalyst? Shooting 8 episodes of The Manager’s Playbook podcast in 7 days.

That’s not my regular cadence. But right now it’s necessary to lay down the foundation on what’s to come next.

Wait on it.


-Ruiz

THE MANAGER’S PLAYBOOK PODCAST

(FEAT. Shawn Desman, Steve Zsirai & Chad Walsh)

Comebacks aren’t accidents. Although, luck plays it’s part, when the opportunity presents itself, the plans need to be orchestrated and executed.

In the modern day music business, the difference between fading away and rising again lies in equal parts resilience, thoughtful strategy, and the right people around you.

Few stories illustrate this better than Shawn Desman’s recent return to the spotlight.

A journey we unpacked in depth on Episode 40 of The Manager’s Playbook with Shawn and his managers, Steve Zsirai and Chad Walsh.

This episode of The Manager’s Playbook Podcast is about this one thing:

How to orchestrate a true comeback to a business that quite frankly tried to write off one of it’s biggest Canadian stars almost a decade ago.

This is Shawn’s Desman’s path back to success.

Accepting the Fall Before Rising Again

Shawn Desman was once at the peak of Canadian pop.

But as the industry shifted, he found himself chewed up by the major label system, battling depression.

What makes his comeback so powerful isn’t just the return. It’s his honesty about hitting rock bottom.

The lesson? You can’t orchestrate a comeback until you confront what broke you in the first place.

Takeaway: Transparency fuels resilience. The most impactful comebacks start with self-awareness and the willingness to acknowledge failure.

The Catalyst Matters

For Shawn, the turning point came when Drake pulled him aside at OVO Fest and said:

“You’re different, eh.”

Sometimes the spark for a comeback comes from an external voice. A co-sign, a mentor, or a fan reminding you of your value. On this night, that one fan who sparked that light in the once forgotten pop star, was one of the biggest artist on the planet, Drake.

Takeaway: External validation isn’t everything, but the right catalyst can reignite belief when self-doubt clouds the vision.

Building the Right Team

Shawn’s story is as much about Steve Zsirai and Chad Walsh as it is about him.

Their approach to management, balancing honesty, empathy, data-driven strategy, and a genuine personal connection, created the foundation for a sustainable comeback.

Unlike past missteps, this time the focus was on long-term trust, transparency, and alignment of values.

Takeaway: A comeback isn’t a solo act. Surround yourself with partners who not only believe in the vision but also have the discipline to execute it with integrity.

Data Meets Creativity

One of the biggest shifts since Shawn’s early career?

The rise of social media and streaming data.

From TikTok clips that went viral to analyzing Spotify and Chartmetric data to pinpoint where the fans are, Shawn’s comeback has been engineered with precision.

The emotional side fuelled the story, but the numbers guided the strategy.

Takeaway: In today’s industry, comebacks are part heart, part algorithm. Success lies in marrying authentic storytelling with smart data use.

Reinvention Through Gratitude

This comeback isn’t about proving critics wrong. It’s about doing it on Shawn’s terms.

Sobriety, family balance, and a deep gratitude for a second chance define this new chapter. That energy translates on stage and online, and fans feel it.

Takeaway: Reinvention works when it’s authentic. Gratitude and purpose aren’t marketing strategies. They’re the foundation of lasting connection.

Watch Episode 40 with Shawn Desman, Steve Zsirai & Chad Walsh LIVE NOW

1:1 CONSULTATIONS WITH RUIZ

I’m now offering 1-on-1 strategy sessions for artists, managers, and execs serious about building beyond music.

Fully tailored to you.

We’ll break down the traditional drivers, masters, publishing, touring, merch, and then map out how to leverage them into real equity: consumer brands, media, real estate, tech, even catalog plays that turn creative work into capital.

With 16+ years across management, development, brand, content, and marketing, I’ll bring honest insight and practical frameworks that move your career forward.

If you’re ready to invest in the long game and build a career that prospers, much like the above concepts discussed above with Rich Castillo, let’s get to work.

PODCAST WRAP UP

Shawn Desman’s comeback reminds us that success in music is rarely linear. 

It’s fragile, messy, and deeply human. 

But with honesty, the right catalyst, a trustworthy team, data-driven strategy, and an enormous amount of gratitude, an artist can not only return, but thrive in ways they never imagined.

For managers and artists alike, the blueprint is clear: Comebacks aren’t luck. They’re built.

Full episode is out now on YouTube and your preferred streaming platforms.

Check out the full conversation with Shawn Desman, Steve Zsirai, Chad Walsh and myself for all the insights.

Share your thoughts with me on IG @mauroisruiz, not only on the podcast but on this Oscar worthy trailer for the episode with my brother Shawn.

Watch the episode with Shawn, Steve & Chad NOW

DON’T FORGET to Subscribe to our YouTube Channel HERE

You can also listen to ‘The Manager’s Playbook’ Podcast on Spotify, Apple, Amazon and several other platforms HERE

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

-Ruiz

THE MANAGER’S PLAYBOOK DISCORD IS LIVE!

We’re Hosting Real Conversations, LIVE.

We’re building a space for real conversations about the music business, no fluff, no gatekeeping. Just artists, managers, and creatives sharing what actually works.

The server is live.

Get in early. You never know who might drop in to talk shop.

Bio

I’m Mauricio Ruiz, the host and creator of The Manager’s Playbook podcast, dedicated to demystifying the world of music management, and Founder/CEO of 8 Til Faint, an Artist Management company with over 5 billion audio streams worldwide. Our past and current clients include Grammy nominated, Juno Award winning multi-instrumentalist and singer/songwriter Jessie Reyez, Skratch Bastid and more.

I am also the Co-Founder of Mad Ruk Entertainment, a content agency with over 3 billion long form video streams worldwide. Our client list includes The Weeknd, Eminem, and Celine Dion, along with renowned brands like Nike, Pernod Ricard and the NBA.

Follow me on IG @mauroisruiz

Follow me on LinkedIn