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10 Questions With the Dude Who Designs Hawaiian Shirts Worn by Jimmy Buffett

The founder of Bali-based Kenny Flowers talks about leaving IBM to start his own brand.

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Upon graduating from UNC-Chapel Hill with a double major in Economics and International Relations, Robertson Scholar Kenny Haisfield went to work at IBM as a digital strategy consultant.

After three, fulfilling years there, perhaps after a late night of searching for a lost shaker of salt in Margaritaville, Haisfield made a fateful decision. He booked a one-way ticket to Bali with designs on starting his own fashion brand despite having no background in the field.

The inspiration for the plan, besides some empty margarita glasses, was a faded-pink Hawaiian shirt Haisfield had gotten from his father as a hand-me-down and that he wore constantly.

Haisfield wanted to go to Bali and find a way to remix his dad’s classic shirt into a new line of clothing that would inspire smiles from those wearing the duds as well as those peeping ’em.

Now 28, Haisfield is the creator of Kenny Flowers, a clothing brand that works with international production teams in Bali and Colombia to manufacture high-quality tropical shirts and other items.

To showcase his story and his shirts, Haisfield sat down with RealClearLife for the latest installment of RCL’s “10 Questions With” series.

Check out what he had to say below.

1. RCL: How did you get into the business?
KH: I always loved wearing my Dad’s hand-me-down Hawaiian and eventually realized I was wearing it to every party, every weekend and every vacation I went on. My buddies started to call me out for always wearing the same faded pink floral, so I started looking for similar styles and when I couldn’t find anything that felt the same, I realized the growing need for fresher, more modern-fitting men’s tropical shirts. So I did what made the most sense—quit my well-paying corporate job, moved to Bali and dove headfirst into creating a brand that would bring new life to a vintage look and make all of our Dads proud.

2. What is the biggest misconception about your industry?
That Kenny Flowers is a summer-only business. It’s year-round. We make go-to shirts that are right for all kinds of different occasions. People are traveling more, and as a result, want vacation shirts that set the tone at all times. On top of that, we play to the seasons and have some exciting fall-toned shirts to keep the fiesta going even as the weather cools off, and awesome long sleeve shirts that are fresh alternatives to flannels—whether you’re wearing them around in New York City or San Francisco, and everywhere in between.

3. What is something that the public wouldn’t know about your job?
That I work harder than they imagine and I wouldn’t want it any other way. Even some of my best friends think I spend most of the day on the beach in Bali, sippin’ coconuts when the reality is I’m happily working around the clock in order to grow Kenny Flowers into the established brand it’s becoming.  While I definitely find plenty of ways to rock my KF shirts in exotic locations all over the world, I firmly believe in a work-hard, play-hard lifestyle, and can often be spotted taking business calls from the beach.

A Kenny Flowers “Waka Flockers” shirt with flamingos on it. (Kenny Flowers)

4. What is the most ridiculous thing or person your job has led you to encounter?
I was traveling around selling shirts out of my duffle bag our first summer in business. When I reached NYC, I hopped off the bus in Times Square and saw the infamous Naked Cowboy, who’s been playing his guitar and singing songs in his underwear and boots daily for 20 years. I felt like the guy needed some more clothes so I gifted him a floral shirt to add to his look and honor his braveness. Little did I know, he was so honored to receive clothing as a gift that he would later go on to wear the shirt and sing memorable lines like “I’m the Naked Cowboy and I’m here with Kenny Flowers, I wear this bad-ass shirt, all 24 hours.”

5. What’s the most important lesson you’ve learned along the way?
The most important lesson I’ve learned is to teach your customers quality. And to do so in a way where they can’t imagine it any other way moving forward. For example, our shirts aren’t cookie-cutter from a big factory in China. They are made fresh in Bali, so you have a bit of paradise with you wherever you go. The shirts are hand cut individually so that the patterns match up on the pocket and down the front. They’re double stitched, with coconut buttons, not plastic. Our original sunglass loop in the front pocket keeps your shades from falling off your shirt. All these details ensure that our customers are looking good and feeling great out there. It’s hard to go back to Amazon printed shirts that are made in China, don’t match up and use plastic buttons after wearing your first KF shirt.

6. Do you have any tips or advice for people looking at your industry?
Starting your own business isn’t easy and it can be intimidating. I recommend thinking through the worst-case scenario of making the jump and making sure you’re 100-percent comfortable with what you’re risking if things don’t go right. Then, you know that if worse comes to worse, it will still have been a solid chapter and experience of your life. Once you’ve done this, don’t think about it again. Get out there and make the best case happen.

7. What was the coolest moment of your career so far and what was the scariest?
The coolest moment of my career so far was definitely discovering that Jimmy Buffett, a lifestyle hero of mine, bought Kenny Flowers shirts in a store in Palm Beach and was wearing them every night on tour this summer. The scariest phase of my career so far was turning a young, fun Kenny Flowers, where I was basically making shirts for friends and family, into a legitimate lifestyle brand where I am now making clothes for good people I’ve never met and being a part of their good times all over the world.

A Kenny Flowers cactus print shirt. (Kenny Flowers)

8. What was your fail-safe job, your Plan B, if this job hadn’t worked out?
When I told my former boss I was going to quit my job and start a Hawaiian shirt company, she applauded my ambition and said I could have my old job back if it didn’t work out. That’s as safe of a Plan B as you can get, but I knew when I quit that I was ready for a new adventure. If things didn’t work out with Kenny Flowers, I still would have picked up incredibly valuable experiences that could have led to jobs with small/medium size startups and e-commerce brands.

9. What’s the key to success in your field?
The key to success with KF is being able to run two businesses at once: the day-to-day operation and then the one I’m working to build. Time flies when you’re busy and running a business you love, so if you’re planned out with a vision you’re working towards, then you can take care of tasks in front of you and be ready for what’s next at the same time.

10. What did you want to be when you were 10 years old?
When I was 10 years old, I wanted to be a professional ice hockey player. At five, I wanted to be Batman. If you look at it that way, being a Hawaiian shirt designer is a pretty normal career choice.