What began as an inside joke turned into a real side hustle, then a real business, then the kind of leap most people keep postponing. Joey Coffin, a former Yelp manager in Toronto, first put “Vacation Darts” on a hat in 2024 after friends kept laughing at the phrase. When strangers stopped him to ask about it and one bar-goer tried to buy the hat off his head for $50, he realized the joke had the legs for commercial success.
From Inside Joke To After-Hours Hustle
It started as an inside joke about how vacation cigarettes somehow “do not count.” The idea tapped into something bigger, which was that people take life too seriously and should sometimes relax, have the extra margarita, go back for more at the buffet or talk to someone they would usually avoid. When Coffin printed the phrase on a hat and wore it out in Toronto, strangers kept stopping him. That was the moment he realized the joke could become a real brand.
Coffin did not quit his job and “follow his passion” on day one. He did the messier thing instead. While working full-time at Yelp, he built Vacation Darts in the evenings, working on the website while friends watched football and life kept moving without him.
By February 2025, the brand was already selling apparel and generating revenue, proving an important side-hustle rule most people ignore, which is testing the market before making the dramatic LinkedIn post.
That early traction came from something simple but powerful. The product felt personal, but not so personal that nobody else could relate to it. Vacation Darts tapped into a recognizable fantasy version of adulthood, relaxed, reckless, unserious and probably wearing a trucker hat. Coffin later told Business Insider that authenticity mattered, especially when paired with organic Instagram marketing and AI tools for ideation and copy.
When The Side Hustle Outgrows The Safety Net
Success did not make life easier at first. It made it more crowded. Coffin said splitting his energy between Yelp and the brand left him feeling like he was giving 50 percent to each instead of 100 percent to one. In January 2026, he left Yelp, where he had worked since 2019, and went all-in. Over the past year, Vacation Darts has processed more than $125,000 in transactions.
The lesson, according to Coffin, is not to quit your job right away but to begin with an idea people understand, build it while your paycheck still covers your bills and then make the leap only when the side hustle starts to feel like a real business. Coffin says he does not plan to go back to big tech. After he started building something of his own, the old idea of stability felt a lot less convincing.
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