If politics is the art of the possible, then Casey Key businessman Henry Rodriguez has mastered the art of the impossible.

Rodriguez, 45, found a way to transcend politics as usual this spring when he helped bring big-league developers and slow-growth advocates together to hammer out a compromise on how growth should proceed east of the Urban Service Boundary.

That revolutionary compromise—a requirement that new development east of I-75 be approved by a 5-0 vote of the county commission, rather than by the direct voter approval once championed by groups like Citizens for Sensible Growth—was overwhelmingly approved by voters May 6.

A prominent figure in Florida Republican politics, Rodriguez was recently appointed to the board of EnterpriseFlorida by Gov. Charlie Crist, whom he describes as “a friend and an inspiration.” He’s one of the primary players behind the candidacy of Bill Furst, who is running to unseat longtime Sarasota County Property Appraiser Jim Todora.

But Rodriguez insists he has no aspirations to run for office himself. Instead, he says he is content to work behind the scenes.

“Politics for me is like a hobby,” he says. “I enjoy it, and it’s something that I’m passionate about because of the change you can create. When I see Crist put in his renewable energies bill, knowing that I was the first one to talk with him about it three years ago, that’s exciting. I love that.”

Rodriguez is used to defying political gravity, as evidenced by his victory a few years ago in rallying SouthCounty residents to back his Wal-Mart development project off U.S. 41 in Osprey.

“I had no idea that I would encounter that degree of opposition to the project,” Rodriguez explains about the Wal-Mart deal—his first commercial real estate project after selling two businesses that made him a very wealthy man. “I went into it thinking, ‘Hey, this is great. People will love it.’ I didn’t realize the institutional opposition to big boxes. Here I was going to the Osprey Revitalization Committee all excited that I was going to bring Wal-Mart to town. Boy, I could have sworn that some people had daggers in their eyes. That was my first real entry into the politics of development.”

Rodriguez managed to win the hearts of neighborhood associations and anti-growth activists by rewriting the playbook. Instead of steamrolling his opponents, he sat down and listened to them. 

“I like to have consensus. I was willing to invest money and resources into making our community a better place, and I wanted to know what people thought, what they wanted, how they saw their community,” he says. “So that started a two-year process of going back and forth with the community. I went to every homeowner’s association, every neighborhood association, every civic association and I asked for their concerns, their ideas, their thoughts. ”

While not every adversary became an ally, most, it would seem, developed at least a sincere respect for Rodriguez.

“Henry charmed people. He came riding in at sunrise telling us all that the solution to Osprey’s problems was an anchor store,” says James Gromko, an Osprey-based artist and founder of the Save Osprey Society (SOS), a grassroots organization formed to thwart Rodriguez’s attempts to put a Wal-Mart on South U.S. 41.

Although SOS’s mission failed (the Wal-Mart Superstore opened in Osprey in 2005), Gromko doesn’t accuse his chief opponent of sinister motives. “Henry is a person who thinks what he is doing is right,” he says.

“Henry is very collaborative,” explains Nokomis real estate broker and president of the South County Assembly of Neighborhoods (SCAN) John Ask. “He reaches out to all

parties. He likes to sit down in living rooms with people. Henry has got the three Ps down—he’s personable, he’s persuasive and he’s a perfectionist.”

Rodriguez’s person-to-person outreach paid off. The Wal-Mart project received a unanimous endorsement from the Sarasota Planning Commission, and scores of residents wrote letters to the county supporting the development plan.   

From Rags to Riches

Rodriguez was born on Long Island in 1963, the son of Cuban immigrants who made their way to the U.S. in 1957,

seeking economic opportunity. His mother worked as a seamstress. His father was a dishwasher.

“My parents came here before the revolution. They came from poor families that weren’t involved in politics. They were seeking a better quality of life,” Rodriguez explains.

The senior Rodriguez became a diamond cutter, but gave up the profession because it was too stressful. “He ended up becoming the maintenance man at a building on Long Island,” Rodriguez says. “So I was the son of the super living in a beautiful place we never could have afforded. We were the only Hispanic family in the area.”

The family relocated to Fort Lauderdale in 1974 when Henry was 11 and when “Fort Lauderdale” and “rural” could still be used in the same sentence. “Back then BrowardCounty was such a beautiful place,” he remembers. “There were cow pastures everywhere. When people talk about growth, they need to see what I saw living there. You just can’t imagine the rampant growth. What’s happening here is nothing like what the east coast went through.”

As a young boy, Rodriguez earned cash shoveling snow. After the family moved to Florida, he took a job at the age of 13 as a busboy at a Chinese restaurant, but quit the first day after seeing servers reusing the uneaten white rice from patrons’ dinners. He then became a bag boy at Publix.

Rodriguez dropped out of PlantationHigh School in 1979 at 16, eager to start earning his own way in the world. He earned his GED that same year, and at 17 was enrolled as a freshman at BrowardCommunity College. A straight-A student, he completed his associate’s degree and set out to seek his fortune, working at various sales jobs until an opportunity to run the Caribbean operations of a growing anti-theft device company presented itself.

“Sensormatic Electronics was looking for someone to service businesses in Puerto Rico and the Caribbean,” Rodriguez explains. “I didn’t have any money but I knew this was a great opportunity, so I borrowed $500 and became the exclusive Sensormatic distributor for the Caribbean and parts of Latin America. It was 1989. I was single, and there were eight women to every man in Puerto Rico. It’s incredible what can happen to a man on an island with those odds.”

What happened to Henry was a chance encounter with a beautiful young German tourist on a San Juan beach. After a rocky start—Susanne took umbrage at Rodriguez’s assumption that she was Swiss—the two hit it off. They were married in 1991 and now have two sons, Alex, 14, and Brian, 8. 

Four years later, the couple began looking for a way back to the U.S. mainland. “Susanne was pregnant with Alex,” he says. “The crime rate in Puerto Rico was high, and we didn’t feel that it would be a good place to raise a child.”

They found a place in Tarpon Springs, but it didn’t take long for Rodriguez to tire of his Caribbean commute.

“I found myself traveling to places like Antigua and Barbados; it was a great life, but it was time to move on,” he says.  “Sensormatic never expected that I would be so successful. I was penniless when I started this thing. I had built up the business to 70 employees. So they were happy to buy me out. I sold the business back to them for over $10 million.”

By anyone’s account, Rodriguez should have been on top of the world.  He was a self-made millionaire 10 times over and was happily married with a new baby. But something was missing. He felt lost.

“My father died the year I sold the business and that was hard. And I guess I got into a post-success funk. I was 30 years old. I had a beautiful wife, a beautiful child, and I was successful beyond my imagination. I kept thinking, ‘Oh my God! What am I going to do for the rest of my life?’ I had this anxiety building up in me. I needed to find something to do.”

Hard Work and Timing

That something was LDC Communications, which Rodriguez started in 1995. A long-distance carrier based in Oldsmar, the company went from a fledgling operation with just one customer to a mega-enterprise that within three years had 900 employees and 50,000 customers from New York to Hawaii.

Rodriguez credits his work ethic and a large dose of luck for his serial business success, but makes no bones about the fact that timing is key. “I’ve been at the right place at the right time a lot. I think I have this sixth sense about things,” Rodriguez says. “People get tons of opportunities that come their way during their lives. I think a successful entrepreneur has some way of knowing which opportunities are relevant and good. And then once you find the right opportunity it takes a lot of focus. When I’m in the middle of a big project, I become like a laser tag missile ready to go after my target. I am focused and somewhat obsessed, working 20-hour days. And timing is everything; you can’t underestimate good timing.”

Rodriguez’s timing has been good. He sold his interest in Sensormatic in 1993, the same year it was named Florida company of the year by the Miami Herald. He got into telecommunications with LDC during the height of the technology bubble, and sold the company in 1998 before that bubble burst. Even the timing of his foray into real estate development was spot on. He moved into it by chance during the height of the building boom, and managed to time his projects right so he would avoid much of the fallout of the infamous downturn.

An Accidental Developer

Rodriguez got into real estate development quite by accident. He had purchased a five-acre, Gulf-to-bay tract on Casey Key for $3.3 million in 1998, intending to build a dream home for his family. “We had fallen in love with the beauty of the area,” he says. “That’s all I was thinking, what a nice place this would be to settle down.”

A year later Rodriguez discovered that he had, in fact, bought four distinct lots, which he could subdivide. He kept two-and-a-half acres and sold the remaining property to a friend at cost. A year or so later he sold his house at a huge profit—an amount reportedly triple what he originally paid—and set his sights on commercial development.

“One day I was driving home and I was saying to myself, ‘Oh my God, Osprey is pretty blighted,’” he says. “There were all these old establishments up and down 41. This was the front door to getting onto Casey Key. I began to wonder if I bought the abandoned Chinese restaurant and all these other businesses that were not well capitalized and if I could somehow create revitalization in this neighborhood, it would be a real benefit for the community.” Rodriguez sees this as a perfect example of thinking like an entrepreneur. “There are 50,000 cars a day going up and down 41 in this area. I saw opportunity where others saw blight.”

Rodriguez starting buying property but had no idea what he would do with it. “I started by just thinking I would buy a four-and-a-half acre piece of property and put up a self-storage. Then the Hoosier Bar was for sale and I bought up nine more acres, then another 25 acres, and before I knew it I had bought 70 acres in Osprey, 34 different parcels ranging from 10,000 square feet to 10 acres.

“Having all this property, I began to realize that the reason that Osprey never took off is because of low density. Retailers like high density. In Osprey, half the radius is in the ocean. Not only do fish not buy, but there aren’t enough people to buy, either, because there aren’t enough rooftops. I started thinking that what Osprey needed was a store that would draw from further away. So I picked up the phone and called Wal-Mart. I got a woman named Judy Smith at Wal-Mart headquarters. She said to me, ‘Remember this phone call because it might turn out that you have a Wal-Mart there in a couple of years.’ So my first entry into commercial real estate was dealing with Wal-Mart. I didn’t use a broker. I just picked up the phone.”

Energy and Balance

While Rodriguez is now refocusing his energies on high-tech, looking for opportunities in renewable energies technology, he still has his hands in SouthCounty real estate development. He sold the property surrounding the Wal-Mart but retained the architectural rights to the $250-million BayStreetVillage and TownCenter development that will cover 45 acres next door and will include high-end retail and office space, multifamily housing, and pedestrian connectivity. He is also developing what he calls Sarasota’s first New Urbanist mixed-use community on 250 acres south of S.R. 681 in north Venice. Although the current housing market has put the project on hold

for a year to two, he’s passionate about his vision.

“We are committed to building an environmentally sensitive self-contained community that meets the highest green standards,” he says.

Rodriguez says he often thinks of slowing down to spend more time with his family, take some time to relax and enjoy his success, and bring more balance into his life.  But after a minute or two of waxing poetic about the benefits of a kinder, gentler lifestyle, he says, “You know, necessity is the mother of invention, and I guess my necessity is to keep busy. If it’s all about money, I don’t want anything to do with it. There has to be a general passion and creativity that  goes beyond money. That’s what keeps me going.”