- December 4, 2025
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Henry Rodriguez was once one of the most prominent, and powerful, developers and political rainmakers in Sarasota, living a fast-paced and high-end life. He attended black-tie dinners regularly, fielded calls from two Florida governors — occasionally with a Big Mac in one hand fresh off the McDonald's drive-thru — and lived with his family in a glorious, 5,500-square-foot, two-story gulf-front mansion on Casey Key.
Rodriguez now seeks to wield his experience in a different way, and on a larger, global scale. He’s become something of an Instagram influencer, having refocused and repriotized his life. His focus, he says, is on living life with four pillars — spiritual, physical, mental and financial — and putting passion and purpose before profit. He also has remapped his personal geography: He now spends one-third of the year in Mexico, one-third in Spain and one-third in Sarasota. (He sold the Casey Key house in 2012 for $4.9 million, lived closer to downtown for a time and is now looking for a new home in the area.)
The social media stats prove his reach in his new life: His Instagram account — henryisfulfilled — has more than 100,000 followers and videos sometimes get up to 20,000 likes. He has some 600 posts, mostly videos where he walks-and-talks about gratitude, joy, personal alignment and more. 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.
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.” In addition to the book and Instagram posts, Rodriguez, through his website, henryrodriguezauthor.com, offers a free mediation, 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.
“I was making basketball-player money, influential and powerful in politics,” Rodriguez said. “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. He moved, at first, to Tulum, Mexico, where he spent most of the past four years in “self-reflection.” He more recently added Ibiza, Spain, to the list of places he lives.
Rodriguez isn’t totally removed from real estate or development. He owns the Siesta Key Palms Resort in Sarasota, just off the Stickney Point Bridge. He bought the property, which for decades was the Tides Inn Motel and Sunset Lodge, in 2016 for $1.9 million. He renovated it and even recently added a Tiki bar.
Rodriguez 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 said, adding that in planning, the project would have 100 units.
This is a far cry from his developer heyday. One notable project he was behind is Bay Street Village & Towncenter, a 41-acre urbanist village in Osprey that opened in 2006 and has residences, shops, offices and restaurants. It’s down the street from what could be Rodriguez’ most notable project: the Osprey Walmart Supercenter, which, when it opened in late 2005, delivered retail to a part of south Sarasota County many believed was neglected for years.
Outside development, Rodriguez played large in both local and state politics. Boards he chaired and served on include Enterprise Florida, the Sarasota Film Festival, the Sarasota-Manatee Airport Authority and Space Florida. Nonprofits he supported include the United Way, the Gulf Coast Community Foundation and Habitat for Humanity.
Speaking recently on a virtual call from his Ibiza home, Rodriguez talked about his four pillars.
On the spiritual, he said it isn’t necessarily about religion or God, but it’s essential, he said, to have a connection to a “source,” which could be “family or community.” On physical, Rodriguez lifts weights, walks 10,000 steps a day and fasts intermittently. His changes are working: he said he's in the best shape of his life, down to 11% bodyfat. He once weighed over 250 pounds, he says, in his McDonald’s drive-thru days.
The mental side, he said, is fueled by the spiritual side in 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. Messages of gratitude range from having five senses to financial freedom to a connection to God.
Rodriguez finally has the financial pillar. The son of Cuban immigrants — mom was a seamstress, dad was a building superintendent — Rodriguez grew up poor in Washington Heights, a tough New York City neighborhood in Manhattan bordering the Bronx. Poverty motivated him well enough that through some technology companies and other investments, he was a multimillionaire by age 30.
But has since learned, he says, 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.” He maintains making a profit is a good and noble goal, but the message he seeks to deliver to other high-achievers now 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.”
This article originally appeared on sister site BusinessObserverFL.com.
