How Kenny Haisfield Turned a One-Way Ticket to Bali into a Global Resort Wear Brand: The Kenny Flowers Story
Meet Kenny Haisfield, Founder and CEO of Kenny Flowers — the lifestyle brand redefining resort wear with bold prints, good vibes, and a whole lot of heart.
After trading spreadsheets for sunsets, Kenny left the corporate grind of New York City in 2015 with nothing but a passion for travel, a vintage Hawaiian shirt from his dad, and a vision to create something different. What started as a one-way ticket to Bali and a few hand-sewn shirts has grown into a globally loved brand known for its upscale, tropical apparel—and an attitude that says, “Paradise is a mindset.”
Now celebrating a decade of laid-back luxury, Kenny Flowers is more than just clothing—it’s a celebration of fun, freedom, and the entrepreneurial spirit. With ethically-made pieces inspired by destinations from St. Lucia to Dubai and bold collaborations with icons like McLaren and Margaritaville, Kenny is proving that when you follow your passion and stay true to your style, you really can build a business that feels like vacation.
What does “entrepreneurship” mean to you? How has your understanding of it evolved over time?
Kenny Haisfield: To me, entrepreneurship is as much about hard work as it is about freedom. It’s opportunity—an opportunity to create change, to make something happen that may not otherwise exist. It’s seeing a gap, a need, or a vision that can positively impact your world and the world around you. Entrepreneurship is about taking matters into your own hands and building something for yourself and others. Over time, I’ve realized that while I knew it wouldn’t be easy, I’ve learned that it’s usually harder and more demanding than the alternative. But when you care about what you’re building and enjoy the process, those extra hours and obstacles are just part of the adventure.
Tell us about your first experience with entrepreneurship. What sparked your interest in building something of your own?
KH: My first experience with entrepreneurship was back in high school when I started CEO4Teens — Creating Educational Opportunities for Teenagers. It was a nonprofit focused on helping financially disadvantaged teens access educational resources and opportunities in Bali. Over time, we helped send over 150 students to college and every one is a success story. I didn’t set out to “be an entrepreneur” — I just saw a need, felt I could make a difference, and led with my heart to take action. Looking back, that experience taught me that entrepreneurship isn’t always about a big plan — sometimes it’s just about stepping up and figuring things out along the way.
What is the origin story of your company? What motivated you to start, and how did those early days shape your journey?
KH: Kenny Flowers began to bloom in 2015, after I quit my corporate consulting job, booked a one-way ticket to Bali, and went all in on creating the next wave of aloha-inspired shirts. But the idea actually sparked a few months earlier — during a sunset cruise with friends, a few beers, and a hand-me-down Hawaiian shirt from my dad. That shirt wasn’t just fabric — it symbolized good times, vacations, and memories… and yeah, I wore it way too often.
In those early days, I worked closely with local artisans in Bali to bring the first few hundred shirts to life and shipped orders from my childhood home (thanks, Mom!). It was scrappy, but that hands-on experience shaped my approach — focusing on quality, creativity, and building a brand that inspires people to embrace the good times, wherever they are.
What do you wish you had known when you started? If you could go back, what would you do differently?
KH: When I started Kenny Flowers in 2015, there was no business plan — or even a return ticket from Bali. Just 110% passion and this feeling that it was my calling to create that next wave of feel-good, aloha-inspired shirts.
Honestly, I’m pretty glad I didn’t know much else going in. If I’d known everything that went into it — I might’ve hesitated. But not knowing forced me to take things day by day, to figure it out as I went, and to stay focused on creating something I believed could bloom. Sometimes blind ambition is exactly what you need to take the leap halfway around the world.
Has there been a pivotal moment or a game-changing decision that defined your growth as an entrepreneur?
KH: The biggest game-changing decision I made was booking that one-way ticket to Bali back in 2015 — and committing to building Kenny Flowers full-time from day one. I knew this couldn’t just be a side hustle if I wanted to create a product I was truly proud of and build a brand that could go the distance. Quitting my corporate job without a clear roadmap was a leap of faith, but it forced me to go all in — to pour my energy into getting the product right, building the brand, and connecting with people who believed in what I was creating. Looking back, that decision wasn’t just about starting Kenny Flowers — it was about giving myself the full space, time, and focus to dream bigger and go chase it.
What is the biggest milestone you hope to achieve in the next three months, and why is it important to you and your business? How are you planning to tackle it?
KH: In the next three months, my mission is simple: get our Margaritaville by Kenny Flowers collection out where the margaritas are flowing. Whether it’s in Key West, Montauk, or somewhere that just feels like 5 o’clock, I want people to experience the collection firsthand. To make that happen, we’re focused on building retail partnerships, collaborating with fun-loving influencers, and generating a buzz that keeps the party going.
What does “success” mean to you, both personally and professionally?
KH: For me, success is about balance — building a thriving business that allows me to live the life I want, while also teeing up our customers to live their best lives too. Personally, it’s about spending quality time with my family, traveling the world, and feeling proud of what I’ve built. Professionally, success means seeing Kenny Flowers continue to grow and create a genuine, positive impact on the world, staying true to the values that got us here — good times, great style, and a laid-back attitude that makes people feel like paradise is a mindset not just a destination.
What is your entrepreneurial superpower? How has it helped you overcome challenges or seize opportunities?
KH: Finding a way. It’s one of our core values at Kenny Flowers, and it’s what’s kept us growing and adapting since day one. Whether it was figuring out how to ship shirts from my childhood room in the early days, how to get into our first few stores or how to navigate supply chain challenges during the pandemic, I’ve always believed that when there’s a will, there’s a way. That mindset has helped me push through roadblocks, turn setbacks and restricted resources into opportunities, and build a brand that thrives on creativity, perseverance and a little chaos.
Can you share one of your proudest moments and one of your darkest days as an entrepreneur? What lessons did those experiences teach you?
KH: One of my proudest moments just happened this week when we launched our Margaritaville by Kenny Flowers partnership and collection, inspired by Jimmy Buffett’s favorite shirt of ours he work on tour all summer 2018. He’s always been a role model of mine, both in the lifestyle he created for himself and inspired in others, as well as a businessman. It honestly still hasn’t fully settled in that a dream partnership I’ve been working on the past year, and dreaming of for many more, is live but we’re headed to the Caribbean for a family vacation this weekend which feels like the perfect way to celebrate it.
To your last question about overcoming challenges and finding a way – one of my darkest days – happened at Surf Expo in Orlando back in 2017 – we invested heavily into our first-ever tradeshow – only for Hurricane Irma to get on the map. It took us days to set up our booth, and it was an absolute ghost town for a half day until they canceled the show. There were no flights available, rental car places weren’t even accepting cars. So we drove a rented minivan full of samples and booth set up across the country to California and started walking right into stores and landed our first few wholesale accounts.
There is a lesson in everything – and in this scenario – it was if you set a goal, in this case, to get in our first few retail doors, you can find a way to get there no matter what.
What personal values drive you as an entrepreneur?
KH: I believe life — and business — should be fun. At Kenny Flowers, we’re serious about quality, but we never take ourselves too seriously. I want our brand to inspire people to loosen up, enjoy life, and embrace that vacation mindset — whether they’re on an island or bringing that essence to them. That belief keeps us bold, keeps us creative, and keeps us grounded in what really matters — creating good times and great memories for others.
How have those values influenced your company’s culture and mission?
KH: I believe in going for it. From quitting my corporate job and booking a one-way ticket to Bali to start the brand, to jumping on big opportunities like the Margaritaville partnership — I’ve always believed that you can’t wait for the perfect moment, you just have to show up and create it. That ‘leap first, figure it out later’ mindset has been key to building Kenny Flowers and keeps me pushing boundaries as we grow.
What’s it like working alone or with a team? How do you approach building strong partnerships?
KH: Working with a team — especially one that’s remote — has been an incredible part of building Kenny Flowers and getting the right people onboard. Long before remote work became the norm, my wife and I were actually already running the business from places like Bali, Colombia, and other paradises around the world. That lifestyle shaped our company culture — we’re flexible, adaptable, and thrive on trust and getting the job done.
We’ve built a team of people we genuinely love working with, and I believe that’s because we focus on finding people who share our values and understand it’s a great opportunity to work for Kenny Flowers and that we genuinely want you to have a job, and a life, you’re happy with.
When it comes to partnerships, it’s the same mindset — we look for people and brands that align with what we stand for. That creates the best, and most fun, work. Whether it’s collaborating with Margaritaville or partnering with influencers who know how to showcase bold prints in paradise, we’re always drawn to those who can naturally bring good energy to the table and make things fun. Building strong partnerships is all about creating real connections — just like we’ve done with our team.
What role has mentorship played in your journey—whether as a mentor or a mentee?
KH: I’ve always believed that mentorship isn’t just about scheduled coffee chats or formal advice — it’s about learning from those who’ve paved their way. Jimmy Buffett, for example, felt like a mentor to me long before I had the chance to collaborate with Margaritaville. The way he built an entire lifestyle and empire around his passion showed me that you can create a brand that’s not just about selling a product — but about celebrating a way of life and building an awesome community.
A goal of mine is to mentor others someday, but until then, I hope my evolving story inspires people to trust their instincts and make the jump to pursue what lights them up.
What excites you most about the market or industry you operate in? How are you navigating its challenges and changes?
KH: No matter how saturated a market, there are always going to be ways to stand out. It’s no secret that clothes are getting easier and faster to make, and easier to bring to market. Most of the clothes people wear these days are made by machines in China, where you can find cheap, lower quality alternative Hawaiian shirts. A challenge of ours is to distinguish Kenny Flowers from that noise, and showcase the benefit of making our shirts in Bali, out of better, higher-quality fabrics, in more limited quantities, and handmade with love and good vibes in a beautiful island factory surrounded by rice fields. Through unique features, tight stitching and pattern-matching detail, we strive to teach our customers quality they can’t find elsewhere.
What’s one daily ritual or practice that keeps you grounded and focused?
KH: With two young kids running around, and waking up early, it’s hard to establish that perfect ritual or practice, but we go on a morning family walk every day and I love it. It keeps me grounded before diving into the day. Talking through travels, business, life with my wife, showing my son the turtles and ducks in the lake, always gives perspective going into a day as an entrepreneur!
Share a moment when your resilience as an entrepreneur was tested. How did you push through, and what did you learn?
KH: One of the biggest tests of my resilience happened at our flagship store in Charleston — and on the busiest day of the year, no less. It was the Saturday before the 4th of July, and our store manager didn’t show up. With no backup plan in place, I jumped in and ran the store myself for the rest of the weekend and week.
It was tough — nonstop customer questions, handling the register, restocking, and making sure everything flowed smoothly — but it turned out to be an incredible learning experience. By stepping in, I gained valuable insight into the store’s flow, our customers’ needs, and the pain points we needed to improve.
That weekend taught me two things: First, resilience isn’t just about powering through — it’s about staying calm, adapting, and finding opportunities in the chaos. Second, there’s no better way to improve your business than rolling up your sleeves and working on the frontlines. The experience gave me the insights I needed to build a stronger, more efficient team — and ultimately create a better in-store experience for our customers. We now have a better team than ever, amazing management and are excited to rock it this season on King Street. And I’m excited to have a few days off over the 4th this year!
How do you manage the demands of entrepreneurship while maintaining your well-being? What strategies work best for you?
KH: This may be my favorite question of the day. When I quit my consulting job and moved to Bali to start Kenny Flowers, my friends assumed I was basically on vacation. The truth? Sure, I’d enjoy a coconut at sunset, but I was also working longer hours than I ever did in my corporate days.
Entrepreneurship is nonstop — it’s a marathon, not a sprint. There’s always something that can be done. But I’ve learned that to be at your best, you have to create moments to turn it off — even if it’s just for a little while. Whether that means hitting airplane mode for an hour at dinner, or stepping away to reset, those intentional breaks make all the difference. When you give yourself time to unplug, you come back sharper, more creative, and ready to tackle whatever comes next.
Where do you find inspiration to fuel your vision? Do you have any creative habits that help you stay innovative?
KH: My biggest source of inspiration comes from travel — exploring new places, soaking in different cultures, and embracing that carefree feeling you get when you’re on vacation. Whether it’s walking through a local market in Bali, discovering a bold new print in Colombia, or sharing a sunset cocktail with friends somewhere warm, those moments fuel my creativity. I also put myself in the shoes of my customers to take what’s inspiring to me and channel it to them.
When it comes to staying innovative, I make a point to keep things light — creativity flows best when you’re having fun and have the space to do so. Whether it’s brainstorming shirt names over a cold beer or finding design inspiration during a casual beach walk, the best ideas often happen when you’re relaxed and open to whatever comes your way.
What kind of entrepreneur do you aspire to be? How do you want to be remembered in your industry or community?
KH: I aim to be a genuine entrepreneur — someone who wasn’t afraid to take risks, make bold moves, and go all in on what I believed in. I want to be remembered as someone who trusted their instincts, kept things fun, and built a brand that brought people together. I’ve always loved connecting people I think would get along and that’s something that I can be remembered for through Kenny Flowers and in general.
How does your work contribute to solving larger societal challenges or helping others?
KH: Let’s be honest. The world needs more positivity, and that’s exactly what we aim to deliver — in every thread, every print, and every product we create. At Kenny Flowers, we know that a great shirt won’t change the world, but feeling good in what you’re wearing can change your day — and that energy is contagious. By encouraging people to embrace a vacation mindset, we’re helping spread good vibes, confidence, and connection — one bold print at a time!
Have you faced a major crisis in your business? How did you navigate it, and what advice would you give others in similar situations?
KH: During COVID-19, we faced a major challenge — as a brand built around travel and good times, our core audience wasn’t exactly booking trips or planning pool parties. We knew we had to adapt quickly.
We pivoted fast, turning our signature fabrics into face masks and donating one for every mask sold to communities in Bali, where our products are made. We embraced ecommerce and leaned into our brand’s ability to help “bring vacation to you.” This allowed us to stay connected with our customers, get them excited for upcoming trips and adventure, while giving back in a meaningful way.
My advice for others? Stay agile, lead with empathy, and find creative ways to support your community when times are hard. Sometimes the best path forward isn’t the one you originally planned — but the one that helps people most.
What’s a problem that keeps you up at night, and how are you working to solve it?
KH: One thing that keeps me up at night is the growing trend of Gen Z gravitating toward fast fashion and celebrating dupes — choosing disposable, unethically made pieces over original artwork and thoughtfully designed, quality clothing like what we create. At Kenny Flowers, we put so much care into creating unique prints and durable products that are made to last — not just for one trip, but for years of good times and memories. We’ve also taken pride in teaching our customers quality, because once they know quality, it’s hard to go back.
Do you have a favorite quote or mantra that keeps you motivated on tough days?
KH: “Success isn’t about comparing yourself to others, it’s about comparing your past self to your current self, and seeing improvement.”
If someone wrote a book about your entrepreneurial journey, what would the title be?
KH: Busy in Paradise
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