This captivating piece is a delightful retelling based on a tête-à-tête with Joey Coffin, a 36-year-old ex-Yelp employee-turned-entrepreneur, currently basking in his e-commerce adventure with Vacation Darts from the vibrant streets of Vancouver. Business Insider has confirmed Joey’s past life, complete with all the receipts to prove it. We’ve trimmed the dialogue for your reading pleasure.
Follow the Dominoes… Or Trip Over Them
Joey never had dreams of launching a global brand—who would? It all started with a whimsical joke about “vacation darts.” Yes, you heard that right. He figured that indulging in behaviors typically frowned upon—like lighting up a cigarette—should come with a holiday pass. After all, what’s a little existential crisis between cocktails and limitless buffet food?
His grand insight? Life is far too serious, and sometimes you need to channel your inner sloth while chatting up that attractive stranger at the resort. A hat featuring this brilliant quip was born in a downtown Toronto print shop, and to Joey’s surprise, more than just his reflection found it hilarious. A bar buddy offered him fifty bucks for it—yes, money for a hat that you casually made at a print shop. Apparently, there’s a booming market for half-baked ideas!
Juggling The Mundane and The Whimsical
Diving headfirst into the role of a side hustler, Joey continued to manage Yelp’s restaurants team, where he spent his days convincing people to pick takeout over a home-cooked disaster. Simultaneously, he was pouring his life into Vacation Darts—a true superhero, only with fewer capes and more margaritas.
By the time February 2025 rolled around, he had transformed his side gig into a not-so-humble endeavor racking up over $125,000 in transactions. Yep, you read that correctly—people were throwing their hard-earned dough at the “vacation darts” brand. Who knew that essential life philosophy could lead to a mini fortune?
The Perils of Entrepreneurial Life
But wait—before you think that Joey just hit the jackpot and sauntered into early retirement, he was, in fact, burning the midnight oil. While most were enjoying Netflix and chill, he was powering through website design until the sun came up. You might think that sounds exhilarating, but let’s give a nod to mental health; there’s only so much midnight creativity one can sustain!
Eventually, he realized that juggling a full-time job and a budding brand was like trying to dance with a cactus: prickly and painful at best. So, he bid adieu to Yelp in early 2026 and threw himself into Vacation Darts with the enthusiasm one reserves for free pizza at a work meeting.
Going All In… and Holding Your Breath
Leaving behind a consistent paycheck is terrifying. Joey admits it felt like jumping off a cliff while Googling, “How to safely land without a parachute.” Spoiler alert: there’s no tutorial for that. Yet, the excitement of being solely responsible for his fate kept him from running back to Big Tech.
Authenticity is Key (and Memes)
So, what’s the magic sauce? Joey gives us two words of wisdom: authenticity and social media. He created a product that resonated with him—and apparently a whole lot of other vacation enthusiasts. Then, leveraging his Instagram following and some cheeky DMs to influencers, he transformed his fledgling brand into a viral sensation. Who says you can’t hustle while being a total meme lord?
The Unbearable Lightness of Not Going Back
Now, you’d think that with success comes complacency, but for Joey, leaving Big Tech was akin to removing a straightjacket. The thrill of creating, the joy of building something that isn’t just a cog in the machine—this is what keeps him awake at night now.
In a world where stability in a tech job seems as real as unicorns, it’s admirable that he’s chosen this chaotic, unpredictable path. Joey Coffin isn’t just a businessman; he’s a man on a quest to spark joy in vacationers everywhere—one dart at a time.
Have a side hustle story that’s more chaotic than enlightening? Reach out to our editor, Jane Zhang, at janezhang@businessinsider.com. She loves chaos!
