A Hurricane, a Virus, a Wedding, and Two Businesses that Almost Failed 1000 Times

I don’t remember the last time my fiancé Kenny and I were in the same place for over two weeks, let alone two months.

We’ve lived out of a suitcase for three years now – running both of our businesses (Kenny Flowers and Jetset Christina) on the road and around the world. 

We’ve been so go-go-go since the day I quit my full-time job. And don’t get me wrong, I have loved every second of it.

We’ve scaled temples, hung in overwater bungalows, chased waterfalls, tried new things, and explored the world together. I blazed a career path as a luxury travel blogger, without a business plan. I figured out how to live, and work, to my fullest potential, every day. In that first year of being a full-time blogger, I made more money than I did in the corporate world. But money also mattered less than it ever had before. It all felt like a dream. 

I know how lucky we are – but someone once told me that “luck is the residue of design” and I’ve never forgotten that.

Kenny and I are lucky – of course. We come from great families and great communities, and we are well-educated. But we did not fall into this life, we designed it for ourselves. And we work so damn hard every step of the way to keep building it together. 

One thing we both have in common is we just keep going, no matter what.

It’s an entrepreneurial spirit that any successful business owner will attest to – when times get tough, when you can’t even see 6 feet in front of you, or when you feel like you’re climbing a mountain that never ends, you just. keep. going. 

It took me four years into blogging to finally quit my 9-5 job. I was cautious. Probably too cautious. But, c’est la vie.

I loved my job in marketing, I was good at it. And I didn’t really believe that I was going to make it as a successful blogger in an already-overly-saturated travel space. I loved my apartment in San Francisco. I loved my friends. I loved living close to my family. I loved my nights out in the city. And, let’s be honest, I loved my paychecks.

But something was driving me forward whether I liked it or not, something I can’t quite explain. I knew I had to pursue Jetset Christina and give it my full energy, but I wanted to give myself enough time to comfortably do it. So I gave myself a runway – 6 months. I set the date. (Something I highly recommend anyone wanting to make a big leap in their life do in order to hold themselves accountable.)  

Labor Day Weekend. That would be when I would quit my full time job. 

We already had plans with my family to go to Chapel Hill (for a football game at my alma mater), followed by a trip to Charleston, and then a trade show for Kenny Flowers the following week that Kenny needed my help with in Florida. With all of that planned, and let’s face it, no PTO left, it made sense that Labor Day would be when I would kick-off my full-time travel career.

Quit my job, a gameday at UNC with my friends and family, a quick jaunt to one of my favorite cities, and then down to Florida. Sounds perfect, right? I organized two full weeks of AMAZING travel partnerships in Florida for after the trade show. Hotel stays and partnerships with brands like Ritz-Carlton, and various properties throughout Miami and the Florida Keys. I lined up a few brands I’d photoshoot while I was in Florida, too. I figured if I kicked off my full-time blogging career with some awesome travel and some paid campaigns, I’d be in a good spot and feeling a little better about, you know, NOT getting a paycheck for the first time.

Ah, the perfect plan.

PLANS. Remember those? HAH. People plan and God laughs, right?

If you know Florida, you probably know where this story is going.

It was 2017.

Hurricane Irma, in an eerily similar way to 2020’s COVID, snuck up on us all. Sure, experts were warning of it way before it hit, but nobody wanted to feel like it was actually going to screw up their picture-perfect plans. ESPECIALLY Kenny and I. 

Kenny had poured $15,000 Kenny Flowers barely had into that Surf Expo trade show. The first one he’d ever done.

Surf Expo, if you don’t know anything about it, is a way for stores to find your brand. Buyers from all over the US and Caribbean scour the aisles for products to put in their boutiques and stores. Behemoth brands like Billabong, Tommy Bahama, and YETI run the show with $100,000+ booths and nonstop meetings set up with buyers all day. Most people are so booked with meetings they don’t even have time to find a small, nobody brand like Kenny Flowers at the time. Most buyers, to be honest, can be pretty arrogant when it comes to a brand they’ve never heard of, so it was an uphill battle for a first-time exhibitor. But it was worth a shot, right? To get in the eyes of some buyers, to get in some of our first stores or resort boutiques.

It was a big investment for an e-commerce brand. With a big learning curve. Not only was it a monetary investment, it was a huge time investment, too – you have to build a booth, have all the right set-up, make line sheets, catalogs, and order forms, know what the buyers are looking for, and how to sell them on your little nobody brand. That is if you can even get buyers to notice you in a sea of other brands doing the exact same thing – but with a lot more capital. 

Kenny put everything he had into that weekend for KF. And I had put everything I had into the weeks that were to follow for JSC. So, when the news warned of a possible hurricane coming to Florida, we did everything we could to stay calm, and optimistic. Orlando, where the trade show was, was far enough North – surely it wouldn’t be a problem, right?


The fear of the hurricane was just as impactful as the actual hurricane. Maybe 10% of buyers showed up to the show. We stood there, smiling and handing out koozies to anyone we possibly could, trying to entice them to look at our sunny, colorful products. But the convention center was a dark, dreary ghost town. What was normally a three-day show was cancelled halfway into day two. Any buyers that were brave enough to be there on the first two days were rushed, distracted and scared that they wouldn’t be able to get home in time before the big hurricane hit.

Similar to coronavirus, there was such fear and unknown in the air, like at any minute the electricity would go out, gas stations would close, grocery stores would run out of toilet paper, and the water would be turned off. It felt like the end of the world. 

And it especially felt like the end of our world. 

We didn’t have time to think about the repercussions of everything this hurricane was taking from both of our infant businesses. We had to pack up the booth and get out of Florida. Quickly. The hurricane had turned and it was coming straight up the state.

Worst. Case. Scenario.

It was going to hit everyone. It had already caused destruction and devastation in the vulnerable Caribbean. All flights were cancelled. So what were we going to do? 

South Florida was already feeling the start of the storm. Which meant our rental car, that we had rented in Miami and were planning on returning after the big Jetset jaunt in the Keys, couldn’t be returned. There was an automated message at the car rental company,

“We are closed due to Hurricane Irma. If you need to return a vehicle you rented, you may return it to any of our other locations.”

ANY of their other locations?

Alrightey then.

We drove a burgundy rental minivan full of Kenny Flowers shirts, mannequins, racks, hangers, and everything else from our booth, across the country to California.

We stopped in Alabama and stayed with a friend, one of Kenny’s groomsmen, for a night, and had dinner with one of my bridesmaids in Birmingham. We wished we could have stayed longer – it felt so good to be surrounded by people we loved in such a scary time, but the storm was chasing us. It was about 12 hours behind us, and it was coming FAST to Alabama.

So, we packed up again, and got back on the road. We had lunch in Nashville at Hattie B’s. We spent the night in Kansas. We drove endlessly.

We both cried, a lot.

We worried we were crazy for quitting our corporate jobs.

Would Kenny Flowers survive? Would Jetset Christina? 

Our perfect vision for that year, and for our entire future, like the window-shield driving away from the storm, was completely fogged. We couldn’t see 6 feet in front of us. But we kept driving.

In-between the tears, we laughed. We smiled. We had a hell-of-a road trip. Kenny played a rap playlist the entire way he made of artists from each place we drove through (from Nelly in St. Louis, all the way to Snoop in Long Beach). We played car games. We kept ourselves entertained, stopped in Colorado, hung out with friends in Los Angeles, and even hustled our way into getting a few stores on the California coast to carry Kenny Flowers (had to make use of all that product in our car somehow right?!), and finally ended up at Kenny’s parents’ vacation home in San Diego.

Where, ironically, we are quarantined today. 

Quarantine for Kenny and I has been interesting, to say the least. We’ve had to postpone a wedding, and transition an entire Kenny Flowers factory to creating masks for COVID-19. The swim factory that manufactures my swim line, Watercolors, and Kenny Flowers’ swim trunks, had to completely shut down. We had to make sure the 30 factory workers could eat for that month or more of shutdown (the culture of Colombia often lives very paycheck to paycheck), so we decided to pay them a large advance, that, let’s face it, we didn’t have. We were banking on a summer of resortwear and swimsuit sales. We were banking on a summer of helping people travel and plan honeymoons.

The blog traffic on Jetset Christina dropped to 10% of what it was pre-COVID. Nobody wanted to even think about travel. And, if you don’t know how a blogger makes their money, it’s largely readership on the blog (those lovely ads you see in my posts – thank you for reading and helping me keep bloggin!!!) combined with affiliate sales (when you book a hotel that I recommend, or buy a product that I write about, I earn a small commission from the brand for driving the sale – at zero cost to you). Obviously, both of those revenue streams took a drastic hit with the onset of COVID-19.

And then there was Kenny.

In that first week, Kenny Flowers had something like 50 bachelor and bachelorette parties ask for refunds on group orders they had made – for trips that could no longer happen. Kenny, of course, being the kind and generous human he is, gave them all their money back, even though we usually have a no returns on group orders policy. When quarantine hit everyone hard, the orders slowed, and all but stopped.

Despite having the most successful month of Kenny Flowers business history in FEBRUARY 2020 (February normally should have been one of the worst months for a summer brand, which meant things were gearing up for a bigger and bigger spring and summer), March took a drastic turn. So many of Kenny Flowers orders are tied in with life events and vacations. And, let’s face it, when all of those get cancelled for the foreseeable future, people start buying loungewear instead of resortwear

Kenny wondered out loud, once again, what the future would hold for Kenny Flowers. I could tell he couldn’t see how to get out of this. The steadfast guy, that I always felt like had all the answers, looked like he just fell off of a mountain right before he got to the peak.

But, luckily, Kenny doesn’t really ever fall down for long. He bounces to his feet, looks up at the mountain, and starts climbing a different way.

I had flashbacks to our road trip. We didn’t give up then, and we couldn’t give up now.

For Jetset Christina, my quarantine mountain was pivoting what used to be a travel blog into an everything blog – if people weren’t interested in reading about travel, I needed to figure out what they ARE interested in reading about right now. 

I knew people would get back to traveling, eventually, but having the need to expand Jetset Christina beyond travel was a blessing in disguise. Before coronavirus, I had no need to grow in other areas besides travel. I was comfortable and content in being the go-to for everything honeymoon and luxury travel related. But now, I had the hunger I had at the beginning of Jetset Christina again. I needed to connect with my audience in a completely new way. Change or die, right?

Now, my audience knows my love for cooking, and tags me on instagram trying the recipes from my blog. People who once trusted my judgment in luxury hotels are now buying the wines I recommend, and sipping out of my favorite wine glasses. They’re asking me for advice on everything from wedding planning, to virtual bachelorette parties, and gifts for loved ones. And I’m writing about it all, every day. 

My blog traffic is back up, and by the way, it is at its highest it’s ever been. The success in lifestyle areas of the blog is invigorating, and exciting. And people are starting to read about travel, again, too. I’ve seen about 30% growth week over week in travel content ever since April 1. It seems like we’re all a little fatigued of not being able to go everywhere we want to right now, so we’re at least going to start planning – for whenever we are able to travel again. 

Kenny, in his true genius form, climbed his quarantine mountain with a blindfold on. He turned to me the week of April 1st and told me he thinks Kenny Flowers should make nonmedical masks. He didn’t know how we were going to do it, but he knew we needed to. I kind-of thought he was crazy, but I’m an entrepreneur’s fiance – I know never to question the crazy.

No other brands were really making masks yet, and Kenny saw an opportunity to do some good for the world while keeping his factory busy and working, and using up excess fabric scraps. We decided to donate proceeds of the masks, and committed to donating a mask for every mask sold as well, leading to more than $10,000 donated to the frontline and over 10,000 masks donated in the FIRST FEW WEEKS.

We also had the biggest Kenny Flowers sales month of all time – despite COVID-19. 

Kenny was so beautifully driven by this non-profit project. He told me that the Kenny Flowers Mask Mission gave him purpose in quarantine, and helped him feel like he was working toward something valuable each day. 

One of my favorite things about him is this constant drive from helping others. At 16, Kenny started a non-profit in Bali raising money to start a college for high-achieving, underprivileged Indonesians to get educated on English, leadership and computer skills. Today, he’s sent 150+ students to college and counting. It’s one of my favorite places to visit in Bali, and I love seeing the impact his foundation has had on the island we love so much.

He told me that his focus in the last few years has been so fully on Kenny Flowers and growing the business, that he’d lost a little sight of the non-profit drive within him. Having this opportunity now to use his platform to make a difference – in both Bali (where we have donated masks) and here in the US (where we’ve donated to Direct Relief), was so exciting to him. It helped him keep climbing.


The demand for the masks, as you can imagine, has been insaneThe first thousand sold out in 30 minutes. We’ve sold close to 20,000 now, and making more every day. And, even though it’s a charitable part of the business, people are also picking up other products with their purchases, and Kenny Flowers is gaining tons of customer emails for future marketing, as well. 

It’s also led to a lot of press for Kenny Flowers – from Vogue to GQ, Men’s Health, Zoe Report, PopSugar, The Today Show, and CBS. It’s brought a ton of new eyes to our small business, and we are forever grateful for that. 

Kenny Flowers is making good on his brand mission – to bring good vacation energy to his customers anywhere, anytime. 

And I’m making good on my mission – to be a trusted, honest resource for you. I have always wanted Jetset Christina to feel like a friend, even if we’ve never met – whether it’s sharing travel recommendations, a cocktail recipe, outfit inspiration, a life story, dinner idea, business advice, or anything else — I always want to connect with you on a deeper level than any other blog out there.

Today, I’m feeling grateful and optimistic. There are sunny days ahead – and even if we’re celebrating summer with margaritas in the backyard, we’ll be wearing our Watercolors and Kenny Flowers, and thinking about all the trips we want to take in 2021 (we came up with a VERY ambitious list last night, lol), and sharing the adventure with you guys every step of the way. If I can leave you with one thing, it’s this:

Be grateful for the challenges. See the sunshine in the storms. And whatever you do, always keep going. 

Check out these other blog posts

All about Watercolors Swim

Our proposal story in Bali

The best gifts to send someone in quarantine

The ultimate beach vacation packing guide

The best wine glasses


The Best Tie Dye Bikinis - all my favorite tie-dye swimsuits for 2021


The BEST Flourless Avocado Brownies Recipe!!


Christina is a leading luxury lifestyle and travel blogger with over 2 million readers. Follow her on instagram @jetsetchristina.