By Tony Adams
Most folks come to Key West to relax, kick back, and party, but Jeff Smead and James Braun came to work. They are the management “mechanics” behind the curtain at Island House, who make lifetime memories for their appreciative and loyal guests.
Viewing the trajectories of their earlier lives, their happy collision seems inevitable. Jeff came to the Keys between high school and college for a summer job with the Boy Scouts of America. After a second summer, it was clear to him that as soon as he finished college, he would move to the Keys full time. Jeff had gotten “Island Fever”, and in July of 2006, armed with a bachelor’s degree in hospitality management from Cal State University, he became a Key West local.
James came to the Keys in the Fall of 2012, with over 15 years of business management experience as well as a summer job bartending at the Pied Bar in Provincetown. He had never been to Key West before but had been convinced to join the Ptown – Key West snowbird migration. During his first week living in Key West, James met Jeff at Island House, at Table #3.
Jeff says, “James introduced himself and started asking me a million questions about my job at Island House. When I tried to beg him off, he asked me to dinner. I wasn’t used to being asked to dinner by someone after just minutes of meeting them, but he persisted for days after my ‘maybe’, and made it quite clear that he wasn’t going to stop until I gave him my number. It took about three days, and finally I caved.”
James says, “Jeff had worked in marketing for the producers of ‘Key West Fantasy Fest’ in 2008. Island House had recently come on board as an event host for the festival. I was a liquor sales rep for Breakthru Beverage, creating wine and spirits programming for about 100 local bar, restaurant, and hotel clients. In addition to designing cocktails, menus, and staff training, I also developed the website for Island House.”
In 2011, Jeff was recruited to join the Island House management team. James joined that team in 2021. When Bobi Lore assumed ownership of Island House, his decision to make these two “Fresh Water Conchs” its general managers had obvious wisdom. (“Saltwater Conch” describes those born in the Keys, while “Fresh Water Conch” indicates non-natives who have lived in the Keys for at least seven years.)
Their partnership at Island House is only half of the story. They also collaborate in the acquisition, renovation, and flipping of houses in historic Key West, providing sweat equity, doing the work themselves every evening, weekend, and holiday for five years. They are currently working on the “haunted mansion” Princess Ann style house next door to Island House. This is the third project the couple has attacked together, and, using proceeds from the first two, the first time they have contracted with locals to do much of the work. (Watch their amazing video journal of moving the house back to its original position on Fleming Street.)
For most couples, the idea of living and working together is at best daunting and at worst a recipe for discord. How do Jeff and James manage this? Jeff says, “It’s a lot… but at this point it’s what we’re both used to. I can’t imagine working without James by my side. We tend to operate better when we’re in the trenches of some sort of chaos, more than when projects are finished and require constant polishing and perfecting. Ours is a yin and yang type of partnership. James is so talented at the things I’m terrible at, and vice versa. We’re very lucky in that sense, that we each let the other one be who he is and be successful at what he’s good at doing. At the end of each day, we’ve both usually been through the wringer in our own worlds, and nighttime is when we download with each other and talk about what tomorrow has in store. It won’t always be like this for us, so we’re trying to openly embrace this time in our life. This is an opportunity to develop something bigger than ourselves, and shepherd Island House into its next chapter. The support we’ve received from Island House owner Bobi Lore, the community, and the thousands of Island House guests has been amazing. There’s just no option to fail. We’re in the thick of it right now, and knowing that all the players involved have the same end goal in mind is what gets us through the tough days.”
Living in Key West has been a challenge and a pleasure for Jeff and James. They finish each other’s sentences, saying, “We love island life. We love not having a commute to work, and having a small circle of really close local friends who live just a few blocks away from us. Everything we need to be successful is already here. Island life has a simplicity that is really appealing to us, because everyone knows each other, and we share a common sense of community. It’s definitely a unique place to live. When you’re meant to be here, it just works. This ain’t the mainland, and we love that.”
What does the future hold for Jeff and James? More of the same, as they continue their strong partnership with Island House owner Bobi Lore. Together, they are writing the next chapter of Island House, renovating rooms, improving the common areas, and adding to the café menu, so that younger guests will enjoy the same “rite of passage” cherished by older guests who keep coming back for more. Jeff and James are skilled custodians of a tradition going back to 1976 when Island House opened its doors to the gay community. The Key West gay community is healthier than ever, and together these men serve it beautifully.
