Christopher “The Mastermind” Massimine is one of recorded music’s best-kept secrets, that is, until now. For years the staff here at Billboard, and our affiliates, have taken Massimine’s calls as he’s pitched and landed coverage for both newcomers and stars alike. His magnetism and can-do attitude have lit up the room each time. When he sells a story, he is able to take the best of artists and translate what they aspire to do with their talent into among the best 2-minute elevator pitches we’ve heard. Perhaps most important, when he’s onsite—when there’s not a pandemic—Massimine always brings donuts, bagels, and coffee, and he delivers them with the same kind of smile you see on a child at Christmas morning.

We’ve wanted to do a feature on Massimine for years and he had always declined. In fact, we were actually surprised when this time he called us to take up the offer. When asked why now, he simply responded “Why not? I’ve never been busier, and we might as well do this thing while some of my work still stands relevant.” Of course, once you’re done reading this article, it’ll become glaringly apparent why that statement is an immense underestimation of Massimine’s accomplishments.

The 34-year-old boy wonder started an epic career in his early 20s, right out of college, after earning his Bachelor’s and Master’s from New York University in just three years. He graduated as the deputy class marshal and as the recipient of NYU’s creative writing grant, awarded to Massimine on the day of commencement. At NYU he was a dorm president, a student senator, a college president, and the president of the University student body. And during Massimine’s freshman year, he was a standby for Drew Lachey in the then longstanding Broadway musical Rent. He later interned with Bethesda, which would kick off his career in the world of video games. And throughout this time, Massimine was learning the ropes of theatrical producing under none other than Harold Prince. Does he sound like an ambitious fellow yet? Well, this is all before his career really started.

Massimine has done more in his short time on the Earth than most people accomplish in a lifetime, or let’s be honest here, several lifetimes. He’s not only an all-star in recorded music, he’s rocked the world of professional theater, television, film, and is undisputedly among the top 10 leaders in video gaming of our time. And then, there’s his imprint in Advertising. Massimine’s been the man behind some of the most-successful brand turnarounds of the past decade and a half, including Old Spice (“Scents for Gents,” “Muscle Man,” “The Man Your Man Could Smell Like”), Dos Equis (he penned the character and for years helped with the scripting for “The Most Interesting Man in the World”), Coca-Cola (notably “Share a Coke”), and even KFC when they ran out of chicken in the UK, Massimine’s quick-witted humor rearranged the letters to “FCK.” The idea proved to be a lesson in class and humility, and helped the fast food giant both save face, and perhaps the future of its market-hold against its competitors. In short, Massimine is a titan. But, we’re here to focus on his role in recorded music. And as generous as the setup reads, it barely scrapes the tip of the iceberg of this larger than life impresario.

The literal Mastermind behind so many success stories of the Industry’s top artists, Massimine has worked with leadership at just about every Major Record Label you can imagine. He was the marketing visionary behind Jason Mraz’s single release “I’m Yours,” as part of the promotion of the album We Sing. We Dance. We Steal Things. Due to Massimine’s efforts “I’m Yours” famously sat atop Billboard’s chart for a then all-time record of 76 weeks. 

As a marketing producer, Massimine built the creative teams and oversaw the promotion for several, now iconic, music videos including “If I Never See You Face Again” (Maroon 5, featuring Rihanna), “The Black Parade Is Dead” (My Chemical Romance), “Back to Black” (Amy Winehouse), “Scream” (Usher), “Another Way to Die” (Jack White and Alicia Keys), “Stronger” (Mary J. Blige), “Emotional” (Rilo Kiley). “F*ck You” (Lily Allen).

In the world of live concerts, Massimine has been brought in as an image compliance representative to the Labels to ensure production reflects the interests agreed to between the Labels and their artists. And for those of our readers who don’t know what that means, Massimine’s job is reviewing everything said at every production meeting (recorded) and ensuring what was said, along with any design work, costuming, choreography, and technical components of each of the concerts represent the artist brand. How does one go about this? Well, when asking Massimine, his response was “there’s a dossier on each artist. In many cases, I’m the person who assembles the parties who create the dossiers. They’re huge: hundreds of pages sometimes. What’s inside? Everything you can imagine on the artist, from their personal mission to their style guide to buzz words that resonate with certain audiences, and things to stay clear of with others. It’s all extremely complicated at first with data that needs to be deciphered, and then tested, and then deciphered again, and then tested, again, until it resonates with a positive consistency. This dossier is the result of the interpretation of all of the data. In short, it’s the science of the artist. In the theater world you’d call such a thing “the production bible.” In recorded music we just refer to it as the “brand book,” which is a little more straight forward, but lacks a certain charm.”

While Massimine was not the first to use the “brand book,” he was among the first to insist that it be reevaluated each year, and within a year, if there have been any significant and visible social or world changes that may impact the artist’s reputation and sales performance.

“Brand books were around years before me,” explains Massimine. “What I just couldn’t grapple with is once they were completed so many Labels looked at them like they were the end product. And I’m like: ‘No. That’s why you’re losing money. Things change. You don’t come up with a business plan and use the same one forever. Why would this be any different? Like we have a chance to look at circumstances and see how they’re impacting the brand.’ To me, it was bedlam that we had all of that data, and we were content just staying the course with that. Well, if you’re hemorrhaging in business, if you do that you’re sunk. This is no different. And I championed this for a few years before people started realize it was a big benefit. You know, people are so conflicted when it comes to change. They want it because they know they need to embrace it to succeed. The other side of that is they don’t want it because it’s new, and being new, it requires new work, and new work can be tenfold as hard compared to the work of the status quo. It’s easy to give up, and justify it when things don’t go right immediately. The best of change takes considerable time and experimentation to manage correctly. Once the executives started to see the long game as unsustainable without the change is when they finally started to implement the change. In some cases it took millions of dollars in losses for me to say, ‘I’ve been telling you what do, and you chose not to listen to me because I’m half your age and nowhere as experienced.’ And really that is what it came down to: ‘who’s this nobody kid telling me what to do?’ Well, now that nobody kid is someone everyone listens to. It’s funny how things like that work out. I was graceful about it then. Now, that I can look back and laugh, I can tell the story as it actually was and people can laugh along with me.”

A musician himself, Massimine has long respected the Industry. “It’s in my blood,” Massimine expounds. “I play five instruments. I sing. I compose. I understand theory to the point where I can jam with others. I think that’s, in part, what allows for me to build a rather quick camaraderie with the artists I work with. In a sense, I’m also an artist. They respect that. It’s different when you’re a hired gun and you have no practical working knowledge of the field. I also understand, not entirely well, the practical technology that supports the Industry. Production loves that. And it makes me feel good because they can see that I care. And of course the Labels can’t understand how I do it. Really it’s pretty simple: I’m just living it. It’s easy when you immerse yourself into what’s actually going on. Nobody ever learned anything worth learning alone in an office.”

When it comes to current projects, Massimine is being a little tight-lipped, only saying: “people are worried I’m spread too thin. It’s not the impression I want to give. Sometimes, it’s important to be quiet about things until they’re closer to surfacing. Then it’s like, ‘oh wow, I had no idea you were doing that, too. That’s amazing that you were able to pull that off while doing x, y, z.’ I’m learning that particularly hard now. Everyone needs extra attention in the pandemic. I’m a big boy and I know my priorities and commitments. I’m loyal to a T. And if anyone’s ever not gotten that reference, loyal-t: loyalty. In my career, and frankly life, I’ve never left anyone behind or in a bind when I’m committed. I think a lot of people just don’t understand the level of capable I actually am. Part of that is still age. Another part of that is in that many people walk through life at way less than 50% of their potential. And that’s where they want to be. They’re comfortable. And that’s okay. That’s choice. And it’s their choice to have. At any given time I’m operating at 80% of my potential. I’ve gotten close to 100% and it’s truly unmanageable while having and sort of an existence worth having. Right now I’m probably at 90%. It’s rough, but I’m hanging in, and I’m having more wins than losses. Plus, I’m now a father, and knowing I have another life to care for fuels me to stay steady at that 90%. It’s now about what kind of example do I want to impart to my son. I want him to grow up knowing the only limiter on anyone’s potential is self. You can choose to go the distance, or chat at the sidelines. Either way is fine. I want to show my son what it can look like if you do choose the marathon. Hopefully, he’ll learn from watching me some things not to do, as well. And in turn, one day, I can learn from him.”

To check out the things Massimine is publicly up to, visit pioneertheatre.org (Massimine is the managing director) and imaginetomorrowllc.com (Massimine is the founder and CEO).

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