TAMPA — Tom DeGeorge sat outside Ybor City Coffee and Tea Co. on a balmy January morning drinking a cold brew while chickens pecked around 19th Street.

As people passed on their way to grab coffee, he greeted them with a “what’s up, buddy?” or offers to book them at Crowbar, the music venue he owns just down the street. He yelled “get back to work” to a guy driving a City of Tampa pickup truck, who laughed and waved.

DeGeorge has run the Ybor City venue where local and national bands play since 2006. The bar is a staple in the local music scene for events like Ol’ Dirty Sundays, which hosts hip-hop heavyweights and break dancers for a weekly party. Not only does DeGeorge own a business in the historic district, he also owns a home there, too.

He’s felt the pain as Ybor City businesses struggled through the pandemic. He’s watched other music venues like the Orpheum and New World Brewery move to other locations. He’s felt the sting of increased parking rates and parking tickets affecting himself and his customers.

He pushed through an October shooting in Ybor and the city’s reaction of increased police presence. And amid rising rents in the district, he secured his Crowbar lease through 2026. But he’s not sure what the future holds.

Ybor City, once a haven of nightclubs, cigar bars and tattoo shops, is undergoing a visible transformation, due in part to plans by developer Darryl Shaw to bring 5,000 residences to the area. Shaw has said that the district needs more of a balance of residences, restaurants and other businesses.

DeGeorge worries that his indie music venue won’t factor into this equation.

“I just don’t fit with what’s happening out here,” he said. “I mean, we’ll see what happens. It might be great. It’s just not going to be what it was.”

In the past few months, a spate of bars including Florida Cane Distillery and White Lie have closed. Zydeco Brew Werks closed its Ybor location in January, and now have a new location at the Museum of Science and Industry near the University of South Florida.

After the recent shooting, Tampa Mayor Jane Castor told the Tampa Bay Times that the area is in a “transitional phase and has been for years,” from a nighttime-focused economy to a greater mix of residential properties and daytime businesses.

She also theorized that the shooting would speed up the transformation.

On a recent walk through the district, changes were evident. Zydeco Brew Werks looked frozen in time, with bar stools turned upside down over tables. A whole block of storefronts near 20th Street and Seventh Avenue sat empty but freshly painted, seemingly waiting to be occupied.

When White Lie owner Mo Pickering tried to renew the nightclub’s lease, she said she was not given the option by her landlord.

Pickering had worked in Ybor for 16 years —her first job was in the same building back when it was Green Iguana. The spot has been home to a few businesses over the years, including Kelly Days Firehouse Tavern and Red Star Rock Bar.

“What’s next?” Pickering said. “Build-a-Bear?”

With the addition of newer businesses like Cheeseology — a spot that offers cheesemaking classes and wine and opened in a former tattoo shop — the district is taking on a more upscale feel that some consider gentrification.

Shaw’s vision for Ybor is a “thriving” residential, workspace and entertainment area that can be enjoyed during the day.

“It’s hard to put Ybor in one category and I don’t think we want to,” Shaw said in a phone interview. “We definitely want a multicultural, diverse district. That includes people from different backgrounds, different levels of income and different ages.”

Shaw is concerned about the district being “heavily weighted toward late-night alcohol,” which he said can cause bad behavior that has “ramifications to the reputation of the district.”

Another component, Shaw said, is that establishments that only open at night create the feeling of a dead zone during the day. Retail options can’t thrive right now because of a lack of foot traffic.

Steven Peterman, who opened Pete’s Bagels in St. Petersburg in 2019, was approached by Shaw’s team about opening a second location in Ybor. The building’s spot next to a dog park felt on brand for the coffee shop, Peterman said in an interview with the Times, and fit with Shaw’s desire to bring small and local businesses to the area.

“During that time, so many people in St. Pete were like, ‘hey, have you been to Ybor lately?’ It seemed like everyone was talking about it. So it felt like there was a really big buzz and we felt excited to be a part of that change,” Peterman said.

Pete’s opened in Ybor in March 2023 and experienced a surprisingly busy summer. But business slowed after the October shooting, although Peterman said it’s evened out now.

A big part of Shaw’s plan is to bring a concentration of artists back to Ybor. It began with plans for a space to house 50 artist studios called The Citrus Factory, which is still in the construction phase. Shaw also owns the Historic Kress building, which has become a hotbed of artistic businesses, anchored by the Florida Museum of Photographic Arts, galleries including Tempus Projects and the Department of Contemporary Art, Tampa City Ballet, Screen Door Microcinema and literary art collectives.

Ybor’s current artistic revitalization is part of a long history of creativity in the area. In the 1980s and ‘90s, artists here worked out of abandoned cigar factories. Gallery director Amanda Poss points to the existing artistic presence at Hillsborough Community College, which has robust visual art and performing arts programs.

Poss is on the board of Tempus Projects and is privy to the concerns artists have about gentrification. The worry is that, as has happened before in the district, artists will make the area desirable and then get priced out from working there.

“People are trying to weigh that passion and enthusiasm and wanting to really dig in and lay down roots with the uncertainty of the future,” she said. “But I would argue there’s always uncertainty. You have to take a leap of faith and commit, and I think that’s what’s happening now.”

DeGeorge said he thinks the activity in the Kress building is phenomenal. But he is still leery about the changes.

“My concern is that this transformative period … what happens if it doesn’t work? What have we done to this entire district?”