Ironically, it was the explosion of Instagram that inspired me to launch my own business.


Since college, I loved wearing my dad’s hand-me-down Hawaiian shirts, but there was one in particular that was my favorite. I wore it every weekend, to every party and on every vacation. Then smartphone cameras started appearing everywhere. People were constantly snapping photos and posting them on Instagram, and I was wearing the same shirt in every one. Friends were even calling me out for it, posting, “Dude, you’ve worn that shirt literally all summer.”


That’s when I realized that I needed more Hawaiian shirts, but I couldn’t find any I liked. I wanted fresher designs with a more modern fit. I also figured I wasn’t the only guy looking for more fun, higher-quality shirts. The old stereotype was that a guy only needed one Hawaiian shirt that he could wear a couple of times a year. With Instagram, though, no one wants to be seen in the same shirt for three pictures in a row. That’s when I decided to try my hand at designing and making my own shirts, and Kenny Flowers was born.


A natural fit

Instagram marketing has been a big part of our success from the get-go. I quit my consulting job in 2015 and sunk my life’s savings into starting Kenny Flowers. After making an initial order of 300 shirts with a factory, I posted my designs on our then-young Instagram page and presold the entire inventory before the shirts were even finished. Many of those initial buyers were family or friends—or friends of friends—but most of them already followed us on Instagram and saw the preorder announcement.


From the beginning, it just made sense to focus my marketing on Instagram. That’s where my target audience was, and still is. That’s the platform they use, and that’s where their attention is—posting whatever they happen to be rocking at the time. That laid-back, yet fun-seeking mindset goes hand-in-hand with my shirts.


Kenny Flowers grew primarily through a small group of really engaged followers. Instagram rewards pages with lots of activity by showing them to more people, and my followers would often post their own pictures of themselves in my shirts and share others’ posts. In fact, for my first two years, I didn’t spend any money on advertising. The demand for my shirts was already so strong that I was able to presell my first few manufacturing runs and reinvest those proceeds into expanding my product line.


Doubling down

Two years ago, I started buying ads on Instagram. Because we already had such a strong base, the ads felt like a natural extension of our brand and a perfect way to reach people who didn’t yet know about us. They were also a great reminder for potential customers who want to join the party but hadn’t bought a Kenny Flowers shirt yet.


To get the most out of those ads, though, it was critical to leverage tracking pixels on our website and Facebook’s retargeting technology so that we get our digital ads in front of people who have already shown interest in our company. That way, we’re hopefully top of mind when they’re ready to make a purchase.


We also use “look-alike” ads that are delivered to people with profiles similar to those of our customers. This is a great way to reach people that I can’t personally meet and have a beer with. The fact that I can be in Bali and reaching new customers in California, New York, Florida and Idaho in the same day is really exciting. Those are the people helping us spread the word organically.


Gaining influence

Many online retailers really focus on using Instagram influencers to help promote their products, but if you want to find success, you need to be smart and selective about choosing who to work with. You have to find the influencers that are best for you and your product—and best for their followers—or it won’t resonate or draw the right type of audience.


For us, choosing influencers is about finding an authentic voice—sometimes among the unexpected people. It might be the food blogger who loves to wear his Kenny Flowers shirt when he goes to brunch. That type of influencer can help you reach into a completely different market.


For example, my fiancé is a luxury travel blogger and a honeymoon influencer, so she can have an impact when she’s sharing relevant posts in which she’s wearing a Kenny Flowers design—or we’re wearing matching shirts—in honeymoon destinations. On the other side of the spectrum, certain business executives have also been influential for us. Suddenly, a whole company might be doing “Floral Fridays” in our shirts, instead of casual Fridays.


Grassroots growth

What’s really special about Kenny Flowers is that it was my friends and family that helped it take off. They were excited to be wearing these shirts, posting pictures of themselves and having people ask where they got their shirts. Eventually it became really fun and memorable to wear a Kenny Flowers shirt. In fact, a customer just sent me of photo of himself proposing to his girlfriend while wearing his Kenny Flowers shirt.


Today, our Instagram following is around 18,000, but these are our most engaged customers and fans. Some have been around from the beginning and some are just finding out about us today. These followers have helped Kenny Flowers go from that first shirt to a full line of shirts, kimonos, beach cover-ups and swimwear for men and women.


I would say that more than half of our sales today are generated through Instagram and Facebook, but there is no doubt in my mind that these social networks are touchpoints for a much more significant portion of our sales. You can never underestimate the power of social media. It’s essential to our business because it’s an essential part of our customers’ lives.

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