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“I come from rough beginnings,” Gallagher said, starting our interview with one heck of an understatement.
His family was homeless during several parts of his childhood, a long chapter of his youth that played out on a backdrop of trailer parks, motels, and every form of government assistance imaginable. Though substance abuse disorders and medical conditions plagued his parents, Gallagher never once let his roots dictate his growth potential.
“The Salvation Army brought cans of food to our house when we were kids,” he said. “For me, these experiences only fueled my goal of becoming a successful entrepreneur and having enough money so that my kids wouldn’t have these struggles.”
As Gallagher bounced around from place to place, his entrepreneurial spirit grew. He caught the business bug at only five years old, walking around his Florida trailer park with a milk crate full of “pretty rocks” that he sold door to door for a dime. In North Carolina, the elementary student made money mowing lawns and selling origami claws on the school bus.
“I made a dollar selling rocks, which was awesome because I had never had a dollar before,” Gallagher said. “I remember making ten dollars selling origami claws, which was crazy. I was on the free lunch program at school but, that day, I was able to buy an ice cream cone which really fueled my desire to keep making money.”
Over the years, Gallagher’s industrial nature would net him a few extra dollars here and there — by mowing lawns, running a paper route, and the like — but it was his introduction to computers that amplified his ambitions.
“I was hooked on computers from the minute I sat down in my mom’s office and played with one,” he recalled. “I started coding and making websites like a Weird Al fan page through Geocities. I thought it was wild that I could play games online with strangers around the world. I knew that computers were my way out of this life; it felt like a no brainer.”
Now living in a small-town neighboring Cincinnati, Ohio, Gallagher discovered that his computer skills were valuable. He made websites for business owners around town before his uncle hooked him up with a customer service job at an insurance company. His pay was $8/hour, a decent chunk of change for a high schooler at the turn of the millennium.
"I saw money as a way to get away from everything I knew my entire life. My uncle was an inspirational figure to me: he had a house, a career, and was decently important at his company. Though my father and uncle both loved me in different ways, my uncle was the one who opened my eyes up to the possibility that I could make it out. He was my guiding light.”
Gallagher wasted no time in making his dreams a reality.
He attended the University of Cincinnati briefly, but dropped out at 22 to code full-time at a design agency. The self-taught programmer split his days between coding and acting, nabbing representation and a one-way ticket to Hollywood.
“Acting was my real passion at the time,” he said. “I focused on that and paid the bills doing freelance programming work for brands like Nike and Johnson and Johnson. About a year after I moved to Los Angeles, I got my girlfriend at the time pregnant. My father was sick and I wanted to make him a grandfather so we moved back to Ohio.”
Gallagher’s story could have ended here. As a software engineer making $90k/year, Gallagher could have easily settled down with pride now that he’d climbed out of poverty. But California called to him once more, first with a $120k software engineering job in San Francisco then again to Los Angeles where he started his own advertising agency.
Back in LA, Gallagher began acting again, heading out to Normandy, France, to shoot a film. He hardly stepped onto the set when his brother called with tragic news: their father had passed away. It would be years until Matthew found out that it was an overdose that cut his dad’s life short at only 63.
“It was such a mindfuck for him to go out like that,” Matthew confessed. “He had a rough upbringing and never escaped that lifestyle. It sucks that his story ended like that.”
There is no consolation for losing a loved one, but these sobering times tend to birth an opportunity for vital reflection and introspection — and it just so happened that one of these moments was enough to change Gallagher’s life forever.
“When a parent passes, it changes the way you think about what fulfills you. I was murdering myself at work and not seeing my kids. I wished that I had a company that I was prouder of; something that had actual value. I had bought my dad a 1953 Rolex for Christmas years before. I actually had to get it back from a pawn shop after he died because he needed drug money. I remember sitting behind the computer in 2016 trying to come up with ideas for a new company when I saw my dad’s watch.”
His million-dollar idea was strapped to his wrist.
Gallagher chose the name Watch Gang because the domain name was available and affordable. The day after he created a website and Instagram profile, he already had his first membership. Then he created ads; a few days later, he had hundreds of new memberships…
…and no inventory.
“I didn’t have a watch to sell these people,” Gallagher said, shocked that his idea gained so much traction in so little time. “I did everything myself, from buying the watches to sourcing the packaging to shipping the memberships. I was working 20+ hours a day by myself, taking customer service calls, flying out to meet with boutique watch brands. Failure was not an option for me.”
Watch Gang shipped 1300 watches in its second month, 5000 in its third month, and earned hundreds of thousands in revenue by December 2016. In 2017, Watch Gang’s first full-year, Gallagher generated 11-million-dollars in sales. They’re on track for 50-million-dollars by the end of 2021.
And, ironically, it’s his watch giveaway videos — not his history in Hollywood — that’s getting him recognized in public.
Having literally made it from a trailer park to Tinsel Town to the top of a hundred million dollar company, what advice do you have for entrepreneurs who may be starting their journey from a place of less than modest means?
“I hope that my story can provide the same sort of inspiration that my uncle gave me. If I didn’t have my uncle, I might have become a drug addict living in a trailer for the rest of my life. Who knows? Maybe my story would have ended like my dad’s. I encourage aspiring entrepreneurs to look for those who will inspire you and know that there’s always a way out through hard work and the right opportunities. I’m told I’m lucky a lot and it used to rub me the wrong way. Yes, I am lucky — I’m lucky I had my uncle, I’m lucky I live in a country where I could climb out of poverty. But when you work hard and live your life like a decent human being, it’s not “luck” that helps you climb out of bad situations. I would love for someone to tell me my story was their driving force to achieve what they thought they were capable of.”
“My dad passing away changed what I wanted out of life and I would highly caution a father getting into an entrepreneurial career. I’m always combatting my drive to achieve more, to build more, while still being a good dad. I think that those two roles conflict with one another. I prioritize my kids over myself and over that ambition, but it’s not easy. You need to be cognizant of the time you devote to your business and the years that go by. It’s easy to get lost and work crazy hours for 15 years — only to look back and realize you missed so much of what you’ll never get back. I definitely overworked myself for seven years straight and wasn’t as present as I should have been to my kids. Thankfully, they’re still young and I’m taking advantage of that time now.”
“We’re expanding outside of watches in the immediate future. I don’t want to be limited to watches my whole life. Watch Gang will be part of a larger company that I’m creating right now.”
Will Matthew’s next venture be as successful as Watch Gang? Time will tell, but the outcome won’t matter. His story is about the intangible; not about a timepiece, but rather, about time itself.
Matthew Gallagher didn’t waste a second feeling sorry for himself or curbing his ambition to fit the reality of his impecunious situation. He did more than dream, filling each passing hour with the determination to defy the odds however he could. One might say selling rocks door to door is a waste of time, but if there’s one person you can count on to make the most out of every minute, it’s Matthew Gallagher.
And that is something you can set your watch by.
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