Crazy Lucky: John Mason on Law, Life & the Music Industry No One Sees

Stacie Jowers
7 days ago
3 min read

When we talk about music, we usually focus on the voices we hear and the faces we recognize. But on The Other Side, the goal is to shine a light on the people working quietly behind the scenes — the makers — whose stories are just as important as the songs themselves.

John Mason is one of those people.

A former musician turned music industry attorney and author, John joined The Other Side for a conversation that pulled back the curtain on the realities of the music business — the parts most fans never see. From legal battles to deeply human moments, this episode wasn’t just about contracts or careers. It was about perspective, resilience, and the emotional weight that often comes with success.

John’s journey into law didn’t start in a courtroom — it started on stage. As a working musician, he experienced firsthand the frustrations many artists face: unpaid gigs, unclear agreements, and a system that often favors everyone but the artist. Those experiences became the foundation for his transition into advocacy. He didn’t walk away from music — he walked toward protecting the people who make it.

Throughout our conversation, John emphasized something that stuck with me: the makers matter. It takes an entire village to support an artist — band members, crew, managers, lawyers, family, and friends — all working together to keep the dream alive. Just like raising a family, raising an artist requires care, trust, and a strong support system.

One of the most powerful parts of this episode was hearing John describe his role not just as a lawyer, but as a trusted confidant. Over the years, he’s built close relationships with the artists he represents — relationships rooted in honesty and humanity. He shared stories from his time working with legendary artists, including Olivia Newton-John, offering a glimpse into the responsibility that comes with protecting both a career and a person.

That responsibility becomes even heavier when fame enters the picture.

John spoke candidly about the human cost of celebrity life — a recurring theme in his book, Crazy Lucky. While success may look glamorous from the outside, the reality is far more complicated. Fame can blur personal boundaries, strain relationships, and strip away anonymity in ways many people aren’t prepared for.

At one point, John offered a simple but sobering reminder: “Be careful what you wish for.”

Success often comes with trade-offs, and not every artist is ready for what fame demands. Long hours, constant pressure, and the inability to move through the world unnoticed can take a serious emotional toll.

The conversation also touched on crisis management — an often overlooked but critical part of the music industry. John shared difficult stories involving accidents, personal struggles, and tragedies that unfolded in the public eye. These moments reinforced just how important it is for artists to have advocates who see them as human beings, not just brands or revenue streams.

Another theme woven throughout the episode was legacy. John spoke about the responsibility of protecting an artist’s work — not just while they’re living, but long after. Legacy isn’t only about catalog numbers or accolades; it’s about honoring the person behind the music and ensuring their story is told with care.

What made this conversation especially meaningful was its honesty. John didn’t romanticize the grind or gloss over the hard parts of the industry. Instead, he offered clarity — reminding listeners that growth often comes from experience, reflection, and learning to define success on your own terms.

This episode of The Other Side wasn’t just an inside look at the music industry — it was a reminder that behind every song is a network of people carrying both the weight and the responsibility of someone else’s dream.

And those stories deserve to be heard.

🎙️ Listen to the full episode:

“Crazy Lucky: John Mason on Law, Life & the Music Industry No One Sees”

📍 Available now on Spotify and all major platforms.

📖 Learn more about John’s book, Crazy Lucky, at Barnes & Noble, Amazon, Books-A-Million, and independent retailers nationwide.