Once-powerful Sarasota developer Henry Rodriguez reshapes, refocuses life

Henry Rodriguez grew up poor in Washington Heights, a tough New York City neighborhood in Manhattan bordering the Bronx. His parents — a seamstress and a building superintendent — were Cuban immigrants. 

That should have made his top-of-the-world success story even more satisfying. 

This is when, in his 30s and 40s, he developed dozens of commercial and residential real estate projects in Sarasota; donated and raised millions of dollars for politicians, including both Charlie Crist and Rick Scott for their gubernatorial runs; sat on and chaired multiple boards; and acquired many of the trappings of wealth, down to a Gulf-front mansion on Casey Key so fancy it had a nickname, Casa Salamanca. Prior to real estate, Rodriguez had success in technology sales and in investing in telecommunications firms, saying he was a multimillionaire by the time he was 30.

But Rodriguez was far from satisfied with his rich successes — though he didn’t realize it at the time. He recalls the day, in 2001, when he was handed a check in an attorney’s office for more than $10 million from Walmart. He had just closed on a deal to sell a large parcel in Osprey, south Sarasota County, to the retail giant. “I was ecstatic and full of dopamine and when I got in the elevator alone I jumped higher than Michael Jordan,” Rodriguez told me during a virtual interview in July while in Ibiza, Spain. “That lasted about three days. Then I was back looking for the next deal.”

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Rodriguez has since learned, he says, that his addiction to the next deal, to winning, really masked insecurities derived from a childhood of always needing to prove himself. That period in his life also taught him a valuable leadership lesson in what not to do, in allowing his ego — and comparing yourself to others — to dictate business and life decisions. 

“I was making basketball-player money, influential and powerful in politics,” Rodriguez says. “I was at the apex of what I thought was success as a poor six-year-old kid, of what I really wanted in life. Then I realized I was miserable. I was miserable because I didn’t value the right things in life. I let my ego get ahead of my soul.“

Rodriguez, 62, didn’t discover this, he says, until his 50s, when a divorce, combined with the pandemic, led to a significant shift in priorities — and geography. He moved, at first, to Tulum, Mexico, where he spent most of the past four years in “self-reflection.” He more recently added Ibiza to the list of places he lives, and is now looking for a home, again, in the Sarasota area, to complete the trifecta.

The end of his marriage turned out to be the starting point for this next act. “I went on a spiritual journey,” he says. “I wanted to figure out what I was doing with my life.”

Triple win

A main path he discovered is now a mission to help others find their way out of what he failed at, he says, in putting profits before passion. He’s doing that in a few ways. He has an Instagram page — his handle is henryisfulfilled — with some 600 posts, where he has walk-and-talk videos about gratitude, joy, personal alignment and more. The page description reads "showing others how to be be wealthy and fulfilled through balancing the spiritual, mental, physical and financial."

His Instagram page has more than 100,000 followers and videos sometimes get up to 20,000 likes. While he hasn’t dropped a new video since 2023, one video, on Jan. 23, 2023 about gratitude, has 2.3 million views. Another one, on Nov. 23, 2002 on plateauing in making life changes, has 1.8 million views.

He’s also not totally out of the development game. He owns the Siesta Key Palms Resort in Sarasota, just east of the Stickney Point Bridge. He also owns a 20-acre site in Lakewood Ranch he’d like to turn into a high-end rejuvenative medicine resort and spa, akin to Canyon Ranch in Arizona but with alternative medicines and IV drips. “I want to redefine what a health care resort is,” he says, adding that in planning, the project would have 100 units. 

But don’t call him a developer. He’ll work on projects again, he says, but it has to be “a win for me, a win for the community and win for God.” 

In addition to the book and Instagram posts, Rodriguez, through his website, HenryRodriguezAuthor.com, offers a free meditation, where he reads a passage over background of soothing music. He’s also been approached about being part of a documentary series filmed in Thailand about spreading and sharing happiness and diverse cultures. 

Pillars with purpose 

Rodriguez also has a book coming out, likely by the end of the year, titled “The Four Pillars of Prosperity: Breaking Free of the Matrix.” Those pillars, he says, are physical, spiritual, mental and financial. Some details on the pillars include: 

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• Spiritual: Rodriguez says this pillar isn’t about religion or God, necessarily, but it’s essential, he says to have a connection to a “source,” which could be “family or community.”
• Physical: Rodriguez adheres to what’s called biohacking, which is basically a new term for changing habits and behaviors to eat and live better. Rodriguez goes to biohacking conferences and he lifts weights and walks 10,000 steps a day. He also fasts intermittently. His changes are working: he says he's in the best shape of his life, down to 11% body fat. He weighed over 250 pounds in his developer heyday, he says, when he would grab a Big Mac from the McDonald’s drive-thru, one hand on the burger, one on his phone. (He washed it down, he adds, with “10 Diet Cokes a day.”
• Mental: Rodriguez works on his mental side, he says, much like his spiritual side, by expressing gratitude. He used to get up at 4 a.m., and the first thing he would do is pick up his phone to check and send emails. Now the first thing he does when he wakes up, he says, is text his friend and gratitude accountability partner, Marc Pelletz, who works in real estate in Sarasota. The messages of gratitude range from having five senses to financial freedom to a connection to God. 
• Financial: Rodriguez says he has learned many, if not every, wealthy person “has an unhealthy inner child in them driven by the pain of not being good enough and the pain of comparison.” While he maintains making a profit is a good and noble goal, the message he seeks to deliver to other high-achievers is “when you follow your passion and purpose, money will follow. Before I was just doing it to make a profit.” His favorite phrase in this pillar comes from Chinese philosopher and writer Lao Tzu: “He who knows he has enough is rich.”