I’m Yours: Exclusive Interview with Christopher “The Mastermind” Massimine

May 1, 2021

We sat down for an exclusive interview with Christopher “The Mastermind” Massimine. Here’s how it went:

Chris, let’s dive right into this.

You’re known in the Industry as a go-to spin doctor for some of the biggest successes in recorded music. You’re on speed dial for major labels and you’ve worked on branding and promotion for well-known recording artists like Mary J. Blige, Sara Bareilles, Janis Ian, Josh Grobin, My Chemical Romance, Pigeon John, Kings of Leon, Bette Midler, Maroon 5, Usher, Jack White and the late greats Aretha Franklin, Tom Petty, and Amy Winehouse.

What’s your secret?

Most of that work is in relationship building. If there’s any secret, it’s just that: cultivating the right relationships, and cutting off the wrong relationships before they cause irreparable damage.

You’ve got to be doing your homework, constantly, and that homework never ends. That homework exists in knowing the product and audience, and those two things are constantly evolving. Madonna reinvented herself every decade. It worked. She’s stayed in touch with her audience as it’s evolved. While some of those changes might seem extreme, they’re really not. A lot can change over a decade, let alone a year.

Products need to serve their audiences in ways that don’t just reflect those changes, but are complementary to the upside within those changes. At the end of the day, recorded music artists need to say something that the core majority of their fans care about. That’s not so very hard to do.

Marketing is a science. Once you have the right data, it starts to tell a story, as all numbers and statistics do when viewed through the lens of socio-economics. From there you get a sense of what story you’re going to tell. You then test it out, and measure its success through engagement and transaction. If those two things are in step with each other and meeting sales projections, you’re in a great place.

Oftentimes, you interpret the data inaccurately and have a false start. You learn what went wrong, then try again. You do that until you get it right. You continue to learn from it. You track it. Then, you’re off to the races!

How did you get your start in music?

The Entertainment world is very small. Once you’re in it and become established, you can easily maneuver into different sectors. For me, I was able to get into recorded music through my work with professional video games.

I had been in the video game sector as an assistant producer on the game The Elder Scrolls IV: Oblivion. I quickly discovered that people in the gaming sector of entertainment cross into other sectors. Creatives from all other mediums seem to converge on the gaming world

As an assistant producer, my role was essentially that of a glorified executive assistant. So, in that role, I’m interacting with so many different parties on behalf of the producers. And because I was given the opportunity to take initiative and show/grow my capabilities, I was entrusted with building relationships across the different departments and coordinating day to day tasks in conjunction with the video game’s line producer.

Out of all of the facets of video gaming I was most attracted to the scoring department, because the music sets the tone of the video game. Scoring is probably the single most important complementary aspect of any video game’s storytelling. As a result, I made a lot of friends with composers and orchestrators. Those composers and orchestrators also worked in film, television, and, of course, recorded music.

At that time, I had also proven my acumen as a marketer, both as a budding professional theatre producer and within the gaming world. I was actually charged with the daily operational coordination of Oblivion’s marketing and advertising efforts. That job is generally overseen by a more senior producer, and I had demonstrated that I understood the gaming market and that I was able to draw a persuasive dotted line from product to customer.

Two things happened almost simultaneously. First, I started getting contractor work from the advertising giants in copywriting/story, and second, I got involved with brand development for recorded artists. Within less than a year, I proved that I had an understanding of how to translate brands into profitable enterprises, and that I was able to get the best out of teams through developing a safe collaborative space.

Before I knew it, I was a frequent marketing producer and independent development lead for major recorded music brands. And in advertising, concurrently, I was creating world-recognizable brands through my storytelling, such as “Scents for Gents” with Old Spice and “The Most Interesting Man in the World” with Dos Equis. I was able to bridge my work in advertising and recorded music, and the benefit of doing that turned out to be astronomical.

I was amongst the first to realize that there was a major benefit in contracting recorded artists directly with advertising firms, and in turn, creating partnership deals that benefitted the major labels in reducing their advertising costs. It was a very simple everyone-winning formula, at least to me. This practice has since become fairly standard practice.

For major labels, the biggest expense is advertising. And for advertising, what’s the biggest cost? Music royalties. I mean, it just makes sense the two would partner, right? When you’re really close to something, you often miss the obvious answer. And that answer was right in front of everyone all along.

What is your typical creative process when working with new music or new artists?

I’m less of a producer in the sense of engineering, although I will almost certainly speak up when I think there’s something missing, or “off”, or if a track just isn’t good enough. Where I thrive as a marketing producer and developmental lead for recorded music is in building up the artists by empowering them and their creativity. You’d be surprised with how little creative control many of these artists have. By backstepping contracts, the artists are given more room to express themselves. It needs to start with trust. The idea of that is something I got beat up over for suggesting as I was making a name for myself.

Many major labels are pretty misunderstood these days. I believe the days of record companies operating with the MO of mafia is pretty long past. Recorded music has become less profitable, and most of the money is made in the concert components. Today’s record executive is generally “in it” because they care about the music. The issue is that their predecessors, many of whom are now retired, created these ironclad agreements that their successors still have difficulty altering without opening themselves and the artists up to harm. When I started, it was actually what the Industry would call the major transition period of dinosaurs to pioneers. That’s brash, and it’s true.

Executives now generally listen to me when I say a contract needs to be renegotiated, because in many cases with established music artists, the reason the artist and their brand isn’t as impactful as it was in its yesteryears is that the contract they’re under has had a traumatic stifle to their creative growth. Imagine being told “your music can change the world”, and then being told “you can’t sing/play that”.

The most important thing I start with is trust. If you don’t have that, you’re not going to go anywhere. After that, I’m looking at the test data to find out what resonates and what is “in trend” and aligned with who the artist is, what the music speaks to, and how that can capitalize on certain global conditions. Finally, I bridge the communication between the artists and labels to have a talk. Not a negotiation, but a conversation.

The point of this conversation is establishing respect for what each party brings to the table. If there’s a disagreement, you work towards compromise. To avoid getting off track, you lead the dialogue with facts, explore assumptions, and seal the deal with emotion. That emotion comes from the story the brand wants to tell about the artist and what the artist wants to say to the world.

Sometimes, that conversation can last for weeks, or months, but when that shared agreement comes about between label and artist, it’s a magical moment. You can see the realization in both parties’ eyes that “this is going to work out”. For me, it’s that moment that makes it all worth it.

I enjoy people truly seeing each other, and going, “Oh yeah, for all of the differences we’ve hashed out, we’re really aligned, and in sync, we’re in this together.”

It’s a moment of unblinded presence.

What’s up next for you? Any new projects?

Always. And like always, my involvement will be credited with how the Labels choose to show it and where the labels have to show it through agreements. That’s the fun in this kind of work.

Since I’m independent, when my name does pop up, it’s like a surprise treat for friends, family, and colleagues. I always get a kick out of it when someone calls or texts me about seeing my name attached to something, whether it’s in a physical sleeve, a concert program, or somewhere on the web.

You oversaw the radio campaign for Jason Mraz’s “I’m Yours” single release. At the time, it played the most consecutive weeks of any single on the charts. Did you ever think that would happen?

Actually, I did. Jason has such a unique sound. I call it “soulful alternative”.

There have since been a number of artists who’ve come onto the scene borrowing from his playbook, but they’re just not the same. Jason is also an artist who is deeply connected to integrity, which we both share. Even more than that, he’s an artist who wants to see the best in humanity.

This was at a time when the recorded music Industry was rethinking its business model, and new leadership was paving the way for better working conditions with their artists. Before that, being a recorded music artist was almost like being an indentured servant. There was flowing money, yet the artist was bound to such scheduling and contractual appearances that there was next to no down time. In some extreme cases, this still exists. Amy Winehouse wasn’t just an artist I worked with. She was a friend. I kept telling her to hang on. In the end, she couldn’t. The money she received as a star paid for the drugs, the drugs were fast, and her free time was short. It’s an easy trend to spot why drug addiction in artists is so common. It was the only way to separate and make space.

At the time, the world was ready to listen to a message about connectivity. It was a time of widespread personal growth. That song reaffirmed that. That song’s message of togetherness, connectivity, and sharing and spreading love… if it didn’t succeed, I would’ve been making some foolish choices.

Opportunities are missed every day because people are more comfortable doing what they know rather than branching out and learning what will have a lasting impact. I didn’t know at first where to go with the single, but I knew the product. I understood where the artist was coming from, and I understood that amplifying that message would best make sense. How that message got amplified is a whole other story.

That’s a tale of knocking on doors, getting knocked down, and frankly, knocking doors down. Jason had made a name for himself in many niche circles, but at that point in his career, he was far from a household name. Radio stations make their money from the advertising space they sell. They sell better with a “sure thing”. Jason wasn’t a sure thing yet.

I got a lot of ducking from radio executives. So, I did things like find out where they would eat lunch and send them a bottle of wine, and worked my way to sitting with them at the table. Or, I waited by their car when I noticed it was double parked to keep them from getting a ticket. I traveled nationally and internationally a lot during this time and I was relentless. I learned to be convincing when I needed to be.

I also speak from a place of authenticity, and most people can see that. I hit the pavement hard for Jason and his team. It resulted with a very positive outcome. Seizing opportunity is all about planning, timing, and luck, right? We had all of those things on our side. It was very cool to see how far we could go. And we went, and went, and went. I thought we would get there, but, you never know until you arrive.

Who’s your ideal musician to collaborate with and why?

Now you just want to get me in trouble! Let’s put it this way: I really haven’t worked with a musician I haven’t enjoyed or gotten along with. I think part of that is because I’m a musician myself. I sing. I play piano, drums, violin, guitar, and bass. I’m not particularly great at any one of them. I do, however, understand theory. And more important, I value music as one of my primary creative outlets. Therefore, I can easily relate to musicians, and I think because of that, they more easily relate to me as well.

What’s one thing you’d like our audience to know about you?

I’m more than one thing, and anyone can be more than one thing. For my entire professional career I’ve been the subject of criticism because I’ve spanned so many professional arenas. From theatre, to gaming, to music, to advertising, to television, to film, to social justice, to social media influencer, to venture capitalism, and mostly recently, contributor and arts journalist to the docket.

I’m also a husband, a father, a son, a friend, and somewhat of an artist in my own right. I encourage anyone reading this to not let others define you. You choose what path you’ll chart. Nobody else can define that, and only you can make it happen.

You can learn more about Christopher “The Mastermind” Massimine or find him on social media via the links below:

Instagram

Imagine Tomorrow LLC

Pioneer Theatre Company

Christopher on Entrepreneur

Christopher on Theatre Art Life

Christopher on News Break