by Jamie Rich | April 26, 2021

Five Fabulous Years

Editor in Chief Jamie Rich shares the highs and lows of Flamingo's first five years and what it takes to become Florida's magazine


I looked down at my watch as the minute hand rolled over the 12—it read 6 a.m. The sun wasn’t up yet, and the night had flown by. “I’ve got to go,” I blurted out to my bleary-eyed colleague Holly, who was staring at a glowing screen. Our eyes were bloodshot, our minds delirious from days of sleep deprivation. 

“I’m still cranking,” she said. “You go. Just make sure you come back,” she joked. I grabbed my purse and ran out of the Flamingo office, which was wallpapered from floor to ceiling with draft page layouts and potential cover options.

Fifth anniversary edition of the magazine.
Flamingo’s Fifth Anniversary Issue, Spring/Summer 2021

“I’ll bring Starbucks!” I tossed back. 

It was spring of 2016, and our small team was hurtling toward the deadline to upload 108 pages of Flamingo’s premier issue to the printer. 

My husband was traveling for work, and I was juggling the childcare for our two daughters, then 9 and 4. Holly, Flamingo’s creative director, and I had planned on leaving the office at midnight, along with the others on our team. But by then, we were in the groove.

Around 8 a.m., my then-executive editor Christina arrived, refreshed (sort of). 

“You guys never left?” she said, shocked to see Holly and I sipping our grande Starbucks drinks and in the same clothes as the day before. We all burst out laughing. (No, I hadn’t changed clothes when I left to drop my kids off at school. That would have taken too much time.) Those early days were as fun as they were grueling. We worked a ton, but I think we laughed even more as we poured our hearts into those first issues. 

Through the years, our small crew grew, adding team members who became friends and friends who became team members (you know who you are). Our approach to making the magazine improved with every edition. At some point, we went from a scrappy startup to an award-winning magazine recognized around the Sunshine State for superior storytelling, photography and design.  

Of course, there have been challenges. Take hurricanes, for example—a unique problem for a Florida publisher. For three years straight, storms tore through the state’s beloved landscape, devastating our staff, contributors and advertising partners. One of our team members even lost her home.

At some point, we went from a scrappy startup to an award-winning magazine recognized around the Sunshine State for superior storytelling, photography and design.

Yet the biggest storm that we’ve had to weather has been COVID-19. You can read about how the pandemic impacted Flamingo in last summer’s editor’s note, “My Coronavirus Story,” but in short: We paused printing and hunkered down.  

A few months into our hiatus, a good friend said to me, “Your magazine is a piece of art. It’s just not the same reading it online.” I missed the magazine too, but our online traffic was up 200 percent, and I was happy about that.

Around the same time, a call came into the office from an older gentleman asking if we were ever going to go back to print. I told him we weren’t sure, but that our website had grown tremendously. After all, we were producing more content than ever, and he should be receiving our newsletter and just … stick with us. I paused, waiting for him to politely request a refund or say that he didn’t like reading magazines on a computer.

“Whoever thought of this magazine is brilliant,” he said, not knowing he was speaking to the founder. “It’s so thoughtful, smart, well-designed and really shows the true culture of Florida. I’ll keep subscribing, but I hope it comes back to print.”

“Thank you so much,” I said, smiling through the phone. “I’ll let them know.”

Behind the scenes with my dream team for our cover shoot at Little Palm Island Resort & Spa. From left, Michael Katz, Jamie Rich, Jesus Bravo and Laura Castillo. Photography by Mary Beth Koeth.

That call was the crack of sunlight that allowed me to start considering producing the printed magazine again. Around the same time, we launched our “Flamingo Friends” campaign, which called on readers to support the work we do. Our readers showed up and truly saved Flamingo during the height of the pandemic. Then the Florida Magazine Association named Flamingo 2020 Magazine of the Year. To be sure, it was bittersweet attending the awards gala via Zoom from my kitchen, but the recognition for years of work couldn’t have come at a more welcome time. 

Today, you’re holding our team’s tribute to the highlights of the past five years, with a wink to the future of what has become Florida’s magazine. I’m proud to present our fifth anniversary issue, the Best of Flamingo Collector’s Edition. It’s different from all the issues that came before it—bigger, glossier, but no less authentic Florida. Longtime readers will recognize some of our most popular stories from the archive, presented here in their original form. There are also new, never-before-seen stories, trips, recipes, music, art and Floridians to inspire you. And for those of you just picking up Flamingo for the first time, welcome to the flock. I hope this is the beginning of a beautiful friendship.

Read our Fifth Anniversary Issue cover story and take a journey to Little Palm Island. Photography by Mary Beth Koeth