Enduring Conversations

Twenty years ago, Florida Trend’s then Executive Editor Mark Howard had an idea. What if, in every issue, we featured someone whose work, leadership, innovation or influence had left a mark on our state. Someone worth studying. Someone worth learning from.

As Mark recently told me, “I saw the Icon as a way to recognize and highlight Floridians with a significant record of achievement in the state who were in the latter stages of their careers — and whose experience had given them some claim to ‘wisdom’ or interesting perspectives; the idea, frankly, was a derivative of Esquire magazine’s ‘What I’ve Learned’ feature.”

The funny thing about magazine ideas is that you never know which ones will stick. Some arrive with great fanfare and quietly disappear. Others slip into the pages almost unnoticed and, before long, become traditions.

Icon became more than a tradition. It became one of our most enduring and beloved features.

I was there at the beginning. I had only been at the magazine a few months as an associate editor, but I had the privilege — and the pressure — of writing the first Icon profile. We chose Wayne Huizenga — the self-made billionaire behind Waste Management and Blockbuster and one of Florida’s most influential business figures.

I was green enough that I didn’t realize why my more senior colleagues passed on the assignment. They knew Huizenga’s reputation for rarely granting sit-down interviews. But Huizenga granted my request, and I drove to Fort Lauderdale before he could change his mind.

To this day, it remains one of the most memorable interviews I’ve ever done — not just because of Huizenga’s stature, but because of how approachable, kind and relaxed he was.

Many CEOs are understandably pressed for time. Huizenga was different. He was fully present, patiently answering my questions and never looking for an exit. And we found common ground almost immediately. I told him that growing up in Miami, my classmates and I sang the Dolphins’ fight song at school every morning after the Pledge of Allegiance. The next thing I knew, the owner of the Miami Dolphins and I were singing it together.

Over time, Icon grew beyond what was first envisioned. During Icon’s early days, some of us at the magazine wondered whether we might eventually run out of people with true statewide stature in a state as regionalized as Florida. Instead, the feature proved that compelling lives and hard-earned wisdom transcend geography. Moreover, not every Icon has been a household name, nor do they need to be. Readers connect not because of fame, but because the conversations feel authentic, candid and revealing.

That authenticity stems in large part from the format itself: The stories are told entirely in the subject’s own words. But there’s a distinct journalistic craft behind each installment. As Mark notes, “The challenge for the writer is to develop a set of questions that will draw out salient comments and anecdotes without having to construct a ‘story.’ The challenge is the preparation and editing, not the writing.”

I’d be remiss if I didn’t offer a hat tip to former Florida Trend Associate Editor Art Levy, who interviewed and penned more Icons than anyone else — 151, to be exact — during his time at the magazine. You’ll see Levy’s byline on many of the Icons in this special issue. He mastered the art of the Icon interview, asking just the right questions, listening closely and never rushing to fill the silence. That’s often when folks are reflecting and about to share some of their best thoughts. In many ways, Art helped define what the feature would become.

Today, Icon remains rooted in the idea Mark Howard had two decades ago: that there is something valuable about listening to people who have spent a lifetime building, leading, creating and enduring — and giving them the space to tell their stories in their own voices.

Now, occupying the role Mark once held, I appreciate even more what he created. In a business built around deadlines and fleeting moments, very few ideas last 20 years.

This one has. And judging by the stories that follow, it still has plenty left to teach us.