Media pro Bobby Harris helps take Caribbean fashion into “uncharted waters”

In this series, WeWork’s director of digital community selects a WeWork member to get to know better, sharing her fun findings with the rest of the community. 

WeWork South of Fifth member Bobby Harris has the enviable role of being a jet-setter for a living. His business, Cabana One Media, which focuses on travel and lifestyle, takes him everywhere from Washington, D.C. to the Caribbean island of Curaçao. Read on to learn about his work combining travel and fashion, the best Caribbean island to visit year-round, and more.

Tell us a little bit about Cabana One Media.

Cabana One Media is an interactive company. We have different properties—magazines, TV, and events—and we are staying in the swimwear, resort wear, fashion, and lifestyle vertical right now. We are going to launch Cabana One TV this fall—it’s a show we will share that will do a lot of fashion and travel segments to be distributed through social media only. So just videos for Instagram, Facebook, YouTube, to really push the social media distribution of the show. Right now, everyone spends their entertainment time on their devices, so I’d rather be there with great quality content so they can see it where they are looking.

How did you start the company?

I’ve been in the media business for a good 10 years.  This new version, Cabana One, came by due to an event in Curaçao for International Swim Fashion Week. From that, we started to work with a lot of fashion clients. And from that, we started to work with more travel clients. And from that, it came together organically.

What have been some of your favorite projects across your clients, like luxury travel brands, fashion brands, and aspects of the food industry?

My favorite project right now is our International Swim Fashion Week in Curaçao. It’s so exciting to work with a country and to draw attention to a country with an event that we produce. The event we do with them is the first type of destination fashion event in the Caribbean—it’s uncharted waters, but it’s worked out very, very well. It’s been fun, and next year marks our third year doing it. We are very excited about it—the event is getting bigger and bigger, and next year we are adding a food and wine festival that’s going to be happening at the same time as fashion week, so attendees will have a lot more to do besides watch fashion shows.

Having your company be present in Washington, D.C., Miami, and Curaçao sounds like an exciting challenge. What’s your day-to-day routine like?

Pretty much the same! I drive to WeWork every day. And our office in Washington, D.C. is a sales office targeting new clients for us. Our office in Curaçao is our small one-person office for sponsorships for our event there. We need someone there on the island to work with local sponsors and keep things going, working with hotels, transportation—that sort of thing. We email back and forth constantly, have conference calls twice a week, but I’ve been doing this for years, and working with multiple offices around the world is business.

What are some of your best recommendations for places to see that you’ve found during your travels?

Curaçao is a great island—it’s very European and Dutch-influenced. I was telling someone the other day that this island has some of the smartest people on earth. Everyone speaks four languages there: English, Dutch, an island language that’s a mix of Portuguese and Spanish, and most of them speak Spanish. One thing that’s cool about Curaçao is that it’s not a tourist island. You feel like everyone is treating you as a friend, not as a wallet of money to be spent. I’ve traveled nearly the entire Caribbean, and that’s a very rare feeling. Curaçao treats you like family, which is why I keep going back to it. It’s a great place to visit all year long.

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