Darryl Shaw isn’t afraid to take risks. His biggest might be in Ybor City.

TAMPA — Darryl Shaw isn’t an open book. The 56-year-old is polite, but reserved. He pauses before he answers questions. Friendly, yes. A gregarious back-slapper? No.

When asked why he chose Ybor City to risk the bulk of a fortune made in veterinary surgery and specialty care, Shaw talks about Ybor’s diverse, tight-knit historical community of Italians, Cubans and Spaniards who walked to work in the cigar factories generations ago.

Shaw was born in suburban Johannesburg. He spent his first eight years in a South Africa under apartheid, a form of racist segregation used to oppress the majority nonwhite population.

“I had an opportunity to see it the other way,” Shaw said

Shaw’s public profile has been rising in Tampa Bay for the better part of a decade as his holdings in Ybor have grown. His portfolio has drawn the attention of the Tampa Bay Rays, who over the last five years have expressed often intense interest in two properties in which Shaw has an ownership stake.

But Shaw hasn’t courted the press. And he hasn’t developed the social and cultural clout of Tampa Bay Lightning owner Jeff Vinik. He goes about his business without fanfare, deliberately flying under the news media radar, associates say.

“I would say that the majority of developers that I’ve met are, you know, sort of gregarious, outgoing,” said Tampa Mayor Jane Castor. “And Darryl, I think, is a little more reserved and shy. Quiet, you know, very thoughtful about what he says and what he does. And so that probably sets him apart.”

Case in point? When asked how many of Ybor’s approximately 600 acres he has ownership interest in, Shaw demurs, saying he has never calculated it, but thinks it’s around 100.

Shaw may be on the modest side, but don’t mistake him for a play-it-safe type. He has a history of betting boldly and winning.

***

Shaw retired in March from BluePearl, a national veterinary emergency and specialty hospital chain he cofounded with his brother. He has a plan for Ybor City called Gas Worx, similar in many ways to Vinik’s $3 billion Water Street development next door, which covers more than 70 acres.

But he has a far more muted public persona than Vinik, whose ownership of the Lightning and high-profile charitable endeavors have made him a household name in Tampa Bay. Water Street, between downtown and Gas Worx’ 50 acres, has been written up in the New York Times, Politico and the Wall Street Journal.

Both embrace walk- and bike-friendly streetscapes designed to lure residents who want to ditch their cars — or at least the commute.

While Shaw has stepped up his profile, taking a larger role in Ybor civic organizations, for instance, he remains something of an enigma to many in Tampa’s business and real estate communities, not to mention the wider public.

Yet the numbers don’t lie. In 2014, Shaw and various partners have spent more than $110 million on properties in and around Ybor. Aside from the Gas Worx property, Shaw bought the former Kforce temporary staffing company site for $24 million last year. Gas Worx alone, an assemblage of separate parcels that include much of what used to be the Tampa Park Apartments, would include as many as 5,000 residences, 150,000 square feet of retail space and 500,000 square feet of office space.

When it’s complete in the next decade or so, Gas Worx could rival Water Street in the wow factor. And the Ybor development could be a final piece of the puzzle to create a mix of residential, entertainment and work options that would wrap around downtown, connecting Ybor to Armature Works to the west and the Channel District and Riverwalk, he said.

Vinik and Shaw know each other. They exchange ideas from time to time and have a “good relationship,” Shaw says.

“It just enhances the district, which benefits everyone,” Shaw said.

Vinik praised Shaw as being a “gentleman.”

“I trust him,” Vinik said, echoing Shaw’s assertion that the synergy between Water Street and Gas Worx helps each project.

Shaw “gets it about walkable neighborhoods,” Vinik said, saying that for Tampa to keep its young people and attract newcomers, it must provide alternatives to the car. Gas Worx, Vinik said, is the latest example of Tampa Bay’s push to become a national magnet for young professionals in search of an urban, green space to live near where they work — with plenty of entertainment options close at hand.

“I’m a fan of Darryl and what he’s doing,” Vinik said.

***

Just after graduating from Brown University in 1988, Shaw and a friend moved to Ybor City, renting an apartment above a stained-glass studio on the corner of N 15th Street and Eighth Avenue. Shaw had grown up in Carrollwood Village without visiting Ybor much. But, in college, the neighborhood’s flavor began to interest him.

Shaw and his friend decided to buy a building at 1632 Seventh Ave. — his first foray into real estate. They paid $110,000, a mixture of cash equity and a bank loan.

Shortly after, Shaw invited his family to watch Guavaween — the raucous former Ybor City Halloween parade and party — from the building’s balcony.

“And we stood up on the balcony of the building. And we had nine of us, my parents, my grandparents. We watched the parade … thousands of people underneath (the balcony).

“Exactly two weeks later, about 5 a.m. on a Sunday morning, I got a call from the police that said, ‘Do you own this building?’ And, I’m happy, I said, ‘Yeah.’ He said, ‘Well, you better get down there because it’s lying in the middle of the street,’” Shaw said.

His father, Brian, remembers the crash of his son’s first business venture well.

“I still shake in my boots when I think about that,” Brian Shaw said.

The collapsed building put Shaw out of Ybor real estate for a quarter century. He went back to school at the University of South Florida for enough accounting credits to take the CPA exam and then spent a few years working at Deloitte before heading to business school at Northwestern University.

***

That might have been it for Shaw, the common story of youthful ambition and risk-taking abandoned for a safe career crunching numbers.

Instead, he started to work for his father’s two local veterinary hospitals. He tried to convince his father to take the vet business national, but Brian Shaw and a partner weren’t interested. Darryl’s brother, Neil, who had followed Brian Shaw into veterinary life, was more receptive.

It was another gamble, one that didn’t particularly worry his father, who said Darryl had always shown entrepreneurial instincts.

“They were young and didn’t have a hell of a lot to lose,” Brian Shaw said.

As the business that became BluePearl Veterinary Services grew, Neil concentrated on the medicine. Darryl Shaw ran the business side. And he put into play an idea he’d written papers about in business school: to nationalize veterinary specialty services. (Another paper involved revitalizing historic districts.)

A crucial moment came in November 2006 as BluePearl was opening a gleaming new Manhattan office staffed with nearly 80 employees. At the last minute, an investor had pulled out and the Shaw brothers decided to secure their own financing.

“It was a huge risk,” Shaw said, adding that looking back he sometimes thinks, “What the hell did we do?”

It looked as if that risk might turn into another flop.

“On Day 1, it was dead. Eighty people there. No patients. Day 2, we had like two or three patients come in, and I was beginning to freak out,” Shaw said.

With 20,000 square feet in Manhattan to pay off, the Shaw brothers drew up maps of all the vets in Manhattan, Brooklyn and Queens. They got to work making their pitch personally to as many as they could.

“We let them know that we’re open. Let them know that we partner with them to see their cases on referral, and then send the case back to them. In 90 days, we were breaking even. So it worked out,” Shaw said.

The lesson learned? Personal relationships can make or break a deal.

In 2015, Shaw and his brother sold BluePearl to Mars Veterinary Health, an international company with thousands of clinics in nearly two dozen countries. Shaw now had plenty of cash and started spending it.

This time in Ybor, as he did with veterinarians in New York, Shaw worked to forge relationships with key players. That included other property owners, such as the Capitano family and Jacob “Booky” Buchman: influential people whose families had generations of history in the historic neighborhood in commerce, real estate and industry.

Buchman, 77, was present at the aborted beginning of Shaw’s Ybor push, having sold him the building that collapsed in 1988.

“I never got a phone call. No one ever said anything to me about it. You have to admire someone like that,” said Buchman, who is now Shaw’s partner, of the collapsed building.

When Shaw looked him up again in 2014, Buchman took him around. He introduced Shaw to the Capitanos, who own Radiant Oil and are major landowners in Ybor, at the now-shuttered La Tropicana Cafe. Shaw listened. He wanted to learn, Buchman said.

Buchman could tell Shaw wanted to incorporate their stories, their memories. To capture what was best about a lost time. Buchman, whose family had owned a department store in Ybor since the early 1900s, said that what interested Shaw, aside from the distinctive red brick and wrought-iron balconies featured in the architecture, was the culture. The way Cubans, Spaniards and Italians had all mixed easily.

“Only way you get that feeling is talking to the old people who have lived there,” Buchman said.

Ybor’s charms are well known. Historic social clubs still dot the district, monuments to ethnic pride for the people who once lived and worked there. Its wide sidewalks, now lined with bar patrons, once thronged with people heading to and from tobacco-rolling jobs at one of the nearby cigar factories.

People still speak with passion for the neighborhood decades after that world vanished.

Now, Shaw’s dream may be coming to fruition. Construction could begin as early as this summer.

When Shaw describes Ybor, he talks of a walkable, tight-knit community. He’ll tell you how Ybor has more acreage than the downtown core. How connecting pathways will allow someone to bike from Hyde Park to Ybor without a near-death experience. The CSX rail line that runs through his development? Parts of it make Shaw think of how Manhattan’s High Line transformed old elevated tracks into a stunning pedestrian corridor. And he’s already announced plans for an artist’s enclave.

Ask Shaw what other cities have provided inspiration, and he’ll mention the redevelopment of Chicago’s Fulton Street Market, another historic neighborhood reinvented for the 21st century.

And he’ll talk math.

“Every block is 200 feet deep and 350 feet wide, so it creates a rhythm, a walkability, that you can’t replicate elsewhere,” he begins. A trolley already connects to downtown, and a planned high-speed rail station could one day welcome visitors from Orlando. And a network of bike and pedestrian paths would eventually enable people to pedal to South Tampa without risking death.

“If we just do it right, and are thoughtful about how to do that, we’re going to end up with one of the most amazing neighborhoods in the United States,” Shaw said.

***

But will building an amazing neighborhood destroy the history of the place? Some have raised that question over the last several years.

City Council member Orlando Gudes is somewhat skeptical of Shaw’s vision. Gudes, who has pushed for the city to be more proactive in addressing soaring rents, including calling for rent stabilization, says Shaw’s initial plans that the City Council approved earlier this year focused on “luxury” residential units.

“He’s starting all luxury.” Gudes said of the initial master plan. “But if you redevelop Ybor, don’t leave out marginalized people, poor people. Be inclusionary with everybody.”

Shaw was receptive to his concerns when they spoke, Gudes said.

“I’ll take him at his word, but the proof is in the pudding,” said Gudes, whose district covers Ybor City.

Charlie Miranda, who grew up in public housing in Ybor in the 1940s, is more supportive. He remembers an Ybor where people walked to work at the cigar factories or rode the street cars. Few people owned cars. That world is gone, Miranda said.

“The Ybor of yesterday was the Ybor of yesterday,” Miranda said. “Ybor City will change again. You got to live with change.”

The 5,000 residential units that Shaw hopes to draw to a mix of residential towers and smaller apartment buildings might recreate a nearly century-old ritual: walking to work, Miranda said.

“Instead of going to the cigar factory, they go to some tech business,” he said.

Another big wildcard: whether the Rays will build a ballpark in Ybor on property owned by Shaw and his partners.

In July 2018, the Rays unveiled plans for a $892 million translucent-roofed stadium topped by a distinctive winglike canopy with huge windows that could open to the breeze. The proposed stadium on a site near Adamo Drive on the southern fringe of Ybor, now part of Gas Worx, drew great fanfare at an Italian Club unveiling.

Five months later that plan was dead, killed by Rays owner Stu Sternberg, who said the financial elements presented by Hillsborough County, the city of Tampa and the Tampa Sports Authority hinged too much on federal tax incentives and lacked details.

The Rays weren’t done with Ybor. Team officials soon had their eyes on another Shaw property, the former Kforce headquarters site on E Palm Avenue and Nuccio Parkway. The viability of that site, on the small side for a full-time stadium, remains up in the air.

Would the Adamo site still be available if the Kforce site doesn’t work? For now, Shaw says, it’s doable. But it wouldn’t be his preference. He has plans for high-rise residential towers in that part of Gas Worx.

Shaw is, by his own account, a casual baseball fan. Growing up in Carrollwood Village, where he still lives in a suburban golf course home down the street from where he grew up, he was a good soccer player for Berkeley Prep. His childhood sports memories are going to Tampa Bay Rowdies games with his father at the old Tampa Stadium, watching Brazilian legend Pelé play.

If the Rays do end up in Tampa, the Rowdies likely will play in Ybor as well. But baseball, Shaw says, has a communal aspect that appeals to him.

“It‘s just an amazing pastime. It brings people into a community that connects them. It energizes the community,” Shaw said.

For Shaw, who plans to move with his wife to Gas Worx, community is an important part of his vision.

That is appealing to Buchman, the man who sold Shaw his first building 34 years ago.

“I joined his journey,” said Buchman. “If you don’t get people behind you it’s not going to be successful. Everyone who joined the journey is very, very pleased.”