This as-told-to essay is based on a conversation with Joey Coffin, a 36-year-old former Yelp employee and founder of e-commerce lifestyle brand Vacation Darts, who lives in Vancouver. Business Insider has verified Coffin’s past employment and business revenue with documentation. The following has been edited for length and clarity.
I never really thought I was going to start a global brand — I just followed the dominoes falling.
It started with an inside joke I thought was funny — the joke was that “vacation darts don’t count,” meaning that while on vacation, I think it’s OK to smoke a cigarette without repercussions.
The underlying sentiment behind the joke is that people take life too seriously and should do something for themselves that goes against the grain every now and then. It means being able to enjoy having an extra margarita at the swim-up bar, going for thirds at the resort buffet, or talking to that cute person they might not approach at home.
I put a logo on a hat that I made at a print store in downtown Toronto, and wore it out. I was stopped a bunch of times. Then, later that same week, a buddy of mine at the bar offered me $50 for it right off my head. Right away, I believed this thing had legs. Whoever saw the brand instantly got the joke.
At the time, I was working full-time at Yelp as a manager on the restaurants team, a role I’d held since joining the company in 2019.
I started Vacation Darts as a side hustle. After coming up with the idea, branding, socials, handles, and website purchase in June 2024, we started selling merchandise and generating revenue in February 2025.
I spent my evenings after my 9-to-5 working on my Vacation Darts
Around 6:30 p.m. I’d be creating the product website while my friends were going to watch football, and I’d be up till 2 or 3 a.m. working on product pages.
It took a toll on my mental health because I felt like I was only giving 50% to my brand and 50% to my full-time job, instead of 100% to one of them. My business evolved from pure joy and excitement into something that felt draining.
I knew the brand was going to be popular, but I didn’t expect the level of growth we had.
The business hit over $125,000 in total transactions in the past 12 months, with over $112,5000 in gross revenue. Once I saw that the more focus I could put into this adventure, the bigger it would get, that made it a no-brainer to pursue this full time.
At the beginning of 2026, I parted ways with Yelp and turned Vacation Darts into a full-time gig to keep up with the growth of the brand. I still appreciate everything that job taught me. The excitement is back now that it’s my full-time work and I can give it the fuel it needs.
I’m putting all my chips in to try to transition from a 9-to-5 to 24/7
I think every entrepreneur who tries something new would be lying if they said they weren’t nervous about where they’re going to get money from. To have a consistent income and then suddenly remove that for something you’re building for yourself is nerve-racking.
When I made the transition, I was nervous, but it was like a butterfly-in-the-stomach feeling that I was on the precipice of something great, and it was mine to mess up.
Here are two strategies that helped me find success with my side hustle that anyone can follow if they’re trying to start their own business and leave their 9-to-5:
1. Create a product that’s authentic to you and others
One thing I realized was super important was to find something authentic to me — and to a lot of other people — and just continue to deliver that authenticity. Do something you actually love and believe in, and that will translate well.
I think my brand is relatable because of the memories that going on vacation and doing something outside the norm will create for you. Everyone wants to be that vacation version of themselves all the time.
I’ve stayed authentic to those details of the brand — it’s about community, humor, and relatability.
2. Leverage social and AI to benefit you, not drain you
When we started launching products in the first two months, I wasn’t advertising — I was just doing original organic content through my Instagram following; word of mouth, people sharing memes online, and people reaching out to me.
I also took shots in DMs. If a celebrity or an Instagram influencer liked or commented on one of my posts, or liked a comment that I left on their post, I’d DM them. I’d say something like, “Thanks for liking this post. Check out our website — we have some really cool stuff that might be of interest to you.” That’s how I started talking with influencers and actors.
Another tool I used quite a bit is AI. I’d use it to redraft my DM intro, or ask it to give me a summary of what happened over the last few days based on my Meta dashboard. I bounced ideas off of it and created prompts to bring about more accurate information.
I don’t have any intentions of going back to Big Tech
I’d never have left Big Tech if I didn’t have the evidence in my business that it was possible for me to do this. I’m fully committed to pursuing my venture. Once I got a taste for paving my own way and creating a product that people want, I became addicted to it.
That feeling of fulfillment — of bringing something to the world and building a community — is more important to me than the safety of a regular job. Tomorrow’s not promised in a Big Tech company, either.
Starting a business and seeing it’s taking off, there’s no feeling like it. That’s what the security of the 9-to-5 steals from you: that exhilaration of building something that people are digging. Now that I have this, this is all I want.
Do you have a story to share about your side hustle? Contact this editor, Jane Zhang, at [email protected].
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