Business Tips

Mikey Mike and his unique entrepreneurial spirit

Anyone who’s explored the music scenes from New York to L.A. knows this country is teeming with talented artists. But for every success, there are countless underground performers still trying to break into the industry. Not long ago, Mikey Mike was one of them, but he ultimately broke in on his own terms.

Getting to the spotlight: An impassioned entrepreneurial spirit

The story of how Mikey got his start really begins with who Mikey is. Between his red hair, humble persona, and laissez-faire attitude toward shirts, he breaks just about every stereotype of a hip-hop artist. In a way, he’s a bag of contradictions. He’s relatable, yet difficult to figure out. He’s an open book, yet a bit mysterious. His lyrics can range from philosophical outlooks to his fondness for curry chicken. He’s an unconventional guy, so it’s no surprise his big break happened in a rather unconventional way due to a fiery entrepreneurial spirit.

Like every promising artist, Mikey’s biggest hurdle was getting his foot in the door (to gloss over the decades of practice it takes to be one of the best in the business). A few years ago, Mikey was producing music in Maryland trying to make the move to California. Every day he would email his music to record labels, producers, and agents in L.A., but all he ever heard back was radio silence. He would even go to concerts to pass out demo CDs with the hope it would end up in the right hands. It’s an all-too-common story any budding musician can relate to. After years of keeping his fingers crossed, he decided to roll the dice with an experimental tactic.

He began emailing record labels pretending to be a popular adult film actress. He knew these producers would be familiar with her and this alias might be enough to get their attention. His angle? The “adult film star” said she was managing her little brother’s friend, who happened to be a talented up-and-coming producer (Mikey). “She” would send some samples of Mikey’s beats, and suddenly people started listening. The same tracks he sent to the same producers from his real email address were finally getting heard. Each time he got a response, he’d explain who he really was, which left many of these producers as impressed with his effort as they were with his music. Just like that, this bold plan jumpstarted Mikey’s career, but more importantly, he had the talent and passion to back it up.

Give a laugh, gain a fan

After getting his work in front of the right people, Mikey went on to produce a song, Jump, on Rihanna’s album, Unapologetic. He then branched out to work on a solo record with the hit, Doin’ Me, with the legendary producer, Rick Rubin. And when it came time to promote his solo album, he again looked for unique ways to reach people and start building his fan base.

While most musicians jockey for likes and followers, Mikey craves more authentic interactions with people. From the beginning Mikey skipped social media as his primary tool and looked to use technology in a different and smarter way. Which is where Sideline comes in. Just as vinyl records still thrive today, social media can never replace the personal touch of calls, texts, and human-to-human interaction. It just sounds better, you know?

Mikey genuinely wants to connect with his audience.

He isn’t the type of artist who releases music for the sake of releasing it. Mikey genuinely wants to connect with his audience. To push his solo album, he did a marketing campaign with a questionable photo of himself, a funny headline, and his Sideline number. You could see it on billboards, park benches, and fliers pasted around L.A. In the end, he received over 25,000 calls. His phone pretty much rang every 5 seconds (which is when Sideline’s Forward Calls to Voicemail feature comes in handy). The story got picked up, exploded on Reddit, and went viral to the point where practically everyone in L.A. knows him, even if they’re not into hip-hop.

Mikey Mike's face on a bench

As you can imagine, it’s impossible for anyone to respond to—let alone connect with—25,000 people in a short period of time. For this campaign to work, Sideline’s Auto-Reply feature was critical. Depending on the day, his reply would send a download link to his new single, the whereabouts of his next gig, or a lighthearted joke—all without Mikey needing to lift a finger. But, the campaign wasn’t fully autonomous. Mikey would frequently take over the conversation, chat with strangers, and actually meet up with people for pizza or drinks.

Mikey Mike's Life On Earth album art

Given the success of his billboards, Mikey is using Sideline to boost awareness for his upcoming tour and new album, Life on Earth. This time, the whole premise is about Mikey being single and being his best self. As he travels the country, he’ll be offering free drinks to anyone that can find him. And to find him, fans can call or text his Sideline number and set up time to hang out.

Ultimately, Mikey wants to get a reaction from people, whether it’s a laugh, or just getting people to say, “What the hell is that?” No one else in the industry is approaching marketing and brand building this way, which makes him a true disruptor in how he approaches his music and his broader business strategy. Uniquely, whenever people reach out, Mikey will be on the other end ready to connect with them in an authentic way—which is really what he and his music are all about. Seriously, see for yourself. His Sideline number is (323) 457-8794.



Even though most of us aren’t rising music stars, Mikey is an entrepreneur in many ways. Between his powerful lyrics and unconventional marketing tactics, Mikey’s advice to other entrepreneurs is clear:

  • Don’t ask, offer.
    Generally speaking, promoting music isn’t all that different from promoting any other product or service. Don’t ask someone to buy what you’re selling; first offer them something, knowing that it could turn into greater value for you later on. For Mikey, the value of his marketing stunts was a laugh or free music download. Down the line, that person may buy the whole album or tickets to a show. If you own a pizza shop, for example, give out free samples once a month. Make an event out of it. Or maybe come up with clever menu item or flavor combination. Even subtle in-store experiences that grab attention or make people laugh can be impactful. But above all, try not to do what everyone else is doing. Today, standing out is half the battle.
  • Believe in what you’re doing.
    It takes hard work to succeed in any industry. However, it’s a lot easier to work hard for something you’re passionate about. Think of success as a series of doors you need to get through. Some doors might be a little jammed while others are bolted shut. Without passion, people quit before the locked doors ever open. If your knocks go unanswered, sometimes the only option is to do what Mikey did and kick a hole through the wall. But, you have to believe in what you’re doing to take it that far. So, find your calling and follow it. That’s the key to making hard work feel a little bit easier.

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