1. What’s the quick origin story of your brand, and what makes your product or positioning genuinely different from other options in your niche?

Joey Coffin: I love to travel, and I believe there is nothing that goes better with a view in a foreign country and a cold drink than Vacation Darts*. I knew that love was shared by many when, at a cliffside winery in Santorini, I lit a vacation dart.

My wife asked, “another!?”. When I said “They don’t count on vacation” I heard the man at the table next to me say “See honey, it’s a thing”.

He got up and joined me for a breathtaking vacation dart over looking the Mediterranean sea and we bonded over a shared love.

At that point I started to think there was a community of people like me that needed a way to connect. So I started posting fun memes about smoking darts on vacation on Instagram.

When I got home I created a logo that would get the message across in a cheeky and noticeable way and put it on a hat.

I must have been stopped 10 times that day by people asking me where I got it.

So to get the people what they want I started a small online store for them to buy a hat. Our first drop of 50 hats sold out in 14 days.

I was shocked at just how many people this joke resonates with. So I did another drop with an additional 50 black hats. That sold out too.

We have since done close to 2500 orders, over $200K in sales and have an IG with over 42k followers. We have lots of designs of hats, shirts, bags, stickers and are always thinking of new ways to help show the world that the people just want to have a little fun sometimes.

*p.s. Cigarettes you only smoke on vacation = vacation dart

2. Since launch, what have been the 1-2 real turning points for your brand-specific decisions, pivots, or experiments that noticeably changed your growth or profitability-and what did you learn from them?

Joey Coffin: The biggest levers I’ve been able to pull are – using AI to analyze the health of the business and suggest paths forward. and getting product in the hands of the right people.

With AI I’m able to ask it to act as a CFO, CEO, president of a high volume multimillion dollar ecom business with exit experience. With that prompt, I ask it what documents, reports or data it needs to make informed decisions to grow the business for a potential exit. I then upload the requeste documents into the model and it can accurately produce insight and information that would costs hundreds of thousands from a mentor. Some of the insights I was able to infer were a low returning customer rate, it helped me to recognize that and set up email campaigns to get buyers to return. The month I executed that strategy we took our returning rate from 8% to 15%. That is one example of a situation where AI has helped to materially improve business operations and has been a significant turning point in running the business on vibes to having a plan.

Being omnipresent and visible on the internet through promo to influencers has also been huge. We’ve been seen on Barstool Sports, Celebrity Podcasts, Bravo, in the NHL and NFL and OnlyFans. With that, people recognize the brand instantly and it adds more credibility to a new online business. The turning point where this grew was an organic post from a Barstool Sports employee where he specifically referenced our product. It helped us break into the US market and has helped to double revenue.

3. Which 2-3 channels drive most of your revenue right now (for example SEO, paid social, email, marketplaces, influencers), and what have you learned about making those channels work in your category?

Joey Coffin: Paid social, email, organic content.

I’ve learned that if you want to scale in paid media, you need to do it with intention and when the data tells you it’s ok. When I first started paying for ads, I tried to scale too quickly and ended up crashing a bunch of campaigns. It has taught me to be patient with paid socials.
I’ve also learned that 20%-30% of revenue can come from proper email marketing. As someone who hates getting spammed by companies, it was something I was hesitant to do. I’ve learned that not every email has to have a hard sell. One of our best producing emails was simply a story about Mondays and how a bad Monday makes those vacation days that much better. Connecting with people in an emotional way rather than always selling has worked well for us.

4. How are you thinking about search in 2026 – Google, AI assistants like ChatGPT, and other discovery platforms? What, if anything, have you changed in your content or site to stay visible as AI search grows?

Joey Coffin: Shopify has integrations that help you to rank high on AI search engines so natively I have that running. I also have learnt that AI wants to use useful information and searches for certain key words. I use AI to write blogs for the website with SEO and GEO in mind, it optimizes what I’ve already wrote to make sure that my information is included in AI search results.

5. What do you do to turn first‑time buyers into repeat customers and advocates? Are there specific experiences, content, or community touches that work especially well for you?

Joey Coffin: I make sure that our customers feel like they are part of a community. My brand brings people together, the amount of DMs and emails I get from customers who have had great experiences wearing our hats and apparel reminds me that I am doing this to connect people.

Having them buy into something thats “more than merch” its a lifetyle, its a club that anybody can join and once you’re in, the other members will have your back.

Also, we want to make the experience of getting your package memorable. Each order gets a handwritten note, free stickers, a custom box with our branding. All of this adds costs but people feel very good about supporting our business when the package they receive is objectively beautiful and had a ton of added value.

Mostly, I let the experience of wearing our apparel bring people back. People feel like celebrities when they wear our stuff because it gets recognized. People get approached randomly to be given compliments. It gets people into clubs in the VIP line, free drinks at the resort swim up bar and a handshake form someone who otherwise might’ve walked right past you.

6. If you had to write a short playbook for an ecommerce founder one stage behind you, what would you double down on over the next 12 months – and what would you stop doing entirely?

Joey Coffin: I would double down on finance and accounting and making sure that its all set up correctly from the beginning. Understanding your balance sheet and cash flow is so important for inventory purchases, and marketing. Understanding what a contribution margin is, understanding how much money you are actually making, understand what it costs to acquire a new customer. All of these financial aspects are very important. A newer entrepreneur will just see sales coming in and think “Ok we’re making money” but without nailing down your unit economics are you really making money or just generating revenue?

I would also stop caring what people think right off the bat. If you’re trying to please everybody, you please nobody. so just find your lane and enjoy being in it. Not every idea is going to work, not every post is going to go viral, and when you are building something big, there will be a lot of people trying to bring you down or be negative. Stay focused on the task and the mission and do whatever it takes to get there. Don’t listen to internet trolls and haters who’s biggest accomplishment will be miniscule compared to your daily achievements.