This edition of Side Hustle Spotlight features Ross Friedman, a sprightly 26-year-old from Boston, Massachusetts, who allegedly traded in his high school textbooks for DJ decks. As the founder of Slacker Media Group, he’s managed to curate live events at the confusing intersection of music, lifestyle, and, if we’re lucky, entertainment. Let’s unravel the mystery of how he transformed a teenage hobby into a full-time escapade. Responses have been edited, but not for comedic effect because that would take too long.
Image Credit: Courtesy of Slacker Media Group. Ross Friedman, doubtlessly pondering the meaning of life or snacks.
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So, darling readers, what was young Ross up to before he set the world ablaze with his side hustle? He was a full-time student, slumming it in the academic trenches of high school while moonlighting as a DJ. Picture it: a 16-year-old spinning beats and trying to convince nightclubs that he wasn’t just looking for a place to throw a teenage rave. He finally found Cambridge’s Middle East Downstairs willing to host his first teenage soirée on a Monday night (because what screams “party” more than the beginning of the week?).
With a whopping $3,000—mostly hoarded from DJ-ing Bar Mitzvahs and proms—Friedman nabbed the venue. The inaugural event attracted over 400 people (probably wondering how they ended up there) and netted him $3,000 in profit. Boom! Proof that life can indeed hand you lemons, and with enough beats, you can make a lemon meringue pie of profit.
Now let’s talk resources. Friedman’s got his finger on the pulse of the entrepreneurial world, advocating for YouTube and Google as the ultimate entrepreneurial survival guide. Thanks to these platforms, you too can learn how to juggle flaming torches while blindfolded! But let’s not forget the pivotal influence of his college professor. The ultimate “ah-ha” epiphany came through a book named “The E-Myth,” which, to summarise, basically suggests that overworking equals underachieving—who knew? With this newfound wisdom, Friedman began to delegate, trade chaos for systems, and manage to hire his first employee without any existential crises (at least, we hope so).
If only Ross could turn back time, he’d hire a team sooner. Imagine the joy of not single-handedly shouldering every task while in the throes of growing pains! Sure, he had a great team, but until recently, he was the lone wolf in charge. Let’s be real: a one-man band only works until someone steps on the wrong pedal, and then it’s just a cacophony of chaos.
The live events industry, as Ross points out with all the enthusiasm of someone describing a dental procedure, is fraught with stress. Who knew that managing countless variables—most of which you can’t control—could ignite a complete meltdown? But Friedman learned to harness stress like a pro. You’d think he was training for the Stress Olympics.
And then came the pandemic: a glorious plot twist if ever there was one. With in-person events suddenly as rare as unicorns, did he throw in the towel and binge-watch Netflix? Not quite. He pivoted faster than you can say “social media influencer” and launched Slacker University, a network of Instagram pages targeting eager attendees starved for events. When the dust settled, boom! A national tour sold out, proving that while the world may shut down, Ross’s entrepreneurial spirit was just getting warmed up.
Now, with an impressive projected revenue of $2.5 million across 150 events, Friedman’s lifetime sales have officially broken the $4 million mark. Life goals: achieved! No longer trapped in the start-up grind, he’s now enjoying a refreshing 40-hour work week, thanks to a not-so-small team. Talk about leveling up!
What makes it all worthwhile for Friedman? The satisfaction in crafting unforgettable experiences for hundreds of thousands—and knowing that he’s made people smile, or at least budge from their resting frown. So next time you need a burst of happiness and a little escape from reality, just remember: Ross Friedman started from DJ booths and now creates smiles and memories, all while sipping on a latte in Cambridge. Take notes and grab your to-do list, because if there’s one takeaway from this wild ride, it’s that a to-do list can keep your sanity close by, while reminding you of all the chaos that comes with entrepreneurial life.
