Jordan Upchurch originally wanted to be a high school teacher. That plan changed when, after a less-than-perfect student teaching experience, he spent a pre-college summer managing the trading post at a Boy Scout camp. His success in revitalizing the post and adding programming — and his enjoyment of the process — led camp leaders to suggest he explore the field of marketing and business.
Today, Upchurch is one of Key West’s leaders in community-focused marketing.
A Missouri native, Upchurch was working in casino hospitality when he visited Key West and became captivated by the island. He quickly applied for local jobs and, after being offered one at Southernmost Beach Resort, relocated in 2019.
“I found my island life, and I was enamored by that and realized this was a place where I could live,” he said. “I wanted to stay, so I figured out a way.”
He later moved to Southernmost Beach Resort’s sister property, The Marker, where the general manager mentored him and encouraged him to start an independent social media and marketing business.
Upchurch subsequently honed his skills working with the Spottswood Companies, becoming their area marketing manager and overseeing multiple properties. He launched his own enterprise, dubbed It’s Social Time Somewhere, in January 2021.
“With all my brands, I build a strategy that we try and accomplish — what’s the messaging we want to get out, what are goals that we want to achieve with their social media,” Upchurch said.
Beyond his client work, Upchurch serves on the local advisory board for United Way of Collier and the Keys. He’s also passionate about supporting initiatives to bolster Key West’s LGBTQ+ community.
“I’ve always wanted to stand up for my community and be involved,” he said. “Visibility is very important for multiple reasons, but I think the biggest reason is for the people that aren’t able to be as visible as others can.”
He’s particularly involved in projects to help remember the island’s beloved rainbow crosswalks, which were removed after a state mandate, and strengthen Pride Key West and local LGBTQ+ organizations.
“I live a very privileged life because I live here in Key West,” said Upchurch. “I’m able to post on social media my true life, talk and share with my friends, have conversations with my parents about my fiancé — and not everybody is able to do that by any means, even in 2026.”
He and his fiancé, Colombian resident Diego Caicedo, got engaged in February and are currently navigating the process to relocate Caicedo to Key West. Meanwhile, the two visit each other as often as possible.
Upchurch also spends time in Missouri with his family, especially his one-year-old nephew Oliver.
“He’s adorable and he’s definitely got a personality of his own,” reported the doting uncle.
Two years before becoming an uncle, Upchurch took on another important role: co-founder of the event that would become the Just a Few Friends Key West festival honoring “favorite son” Jimmy Buffett’s life and music.
On the morning of Sept. 2, 2023, reading that the famed singer-songwriter had passed away, he knew Buffett should be memorialized on the island where he developed his signature sound. After reading a remembrance on social media by Paul Menta of Key West Legal Rum, he contacted Menta asking if anyone was planning a traditional Second Line March to celebrate Buffett’s life.
“Paul quickly responded, ‘You and me are going to do that Second Line — get the word out on social media.’” Upchurch recalled.
Startled but willing, he did. On Sept. 3, thousands of Florida Keys residents and visitors gathered on Duval Street for the march. It featured strolling musicians, people carrying large photos of Buffett, and the camaraderie found at his typically sold-out concerts.
“It provided a space for a lot of people to grieve and to be together, and it’s what we all needed,” said Upchurch.
The one-day procession evolved into the annual five-day Just a Few Friends festival, with the addition of organizational powerhouses Jill Snodgrass and Sean Krikorian. Events typically range from a margarita bar stroll and freewheeling storytelling sessions to the highlight Second Line March and concerts by Buffett’s Coral Reefer Band members. It draws participation from fans around the U.S., as well as enthusiastic support from the Key West community.
It’s that community that keeps Jordan Upchurch upbeat and excited about opportunities and his life on the island.
“I came to Key West because of the location, the warmth, the ‘tropicalness’, the water — but the people made me stay,” he said. “We find ways to bug each other sometimes, but at the end of the day, we have a very special bond between all of us.”
