Stephen DiMare’s story of his incredible success in business is as inspiring as it is fascinating
One of the coolest things about being the editor of ExploreOldCity.com is that I can just call up any person or company I care to, speak to their representative, and say I would like to interview so-and-so for our website, and viola! In this case, I very much wanted to meet the “mad genius” behind what is arguably the best popsicle you will ever eat in your life – the Hyppo Pop.
We have lived in Saint Augustine for the past 6 years after moving here from New Jersey by way of Colorado. Long before starting this website, I had been a Hyppo Pop fan fromthe first day my kids dragged me there to but them a popsicle. The first article I ever wrote about the Hyppo was entitled Grooving On Gourmet Popsicles At The Hyppo Can Be Quite Addicting and the “research” I had to do for that article was quite delicious, as you can imagine. Having always been fascinated by biographies of successful people, I very much wanted to meet the Hyppo Pop creator, and hear his story for myself.
It all began with a random muse on a late-night flight from Montana
On the official Hyppo Pop website, we first hear of how it all began:
“In the early months of 2010 Stephen DiMare was working in Montana for a winter at the Lodge at Big Sky and flew home to St. Augustine for a friend’s wedding. On the flight he pitched his idea for a coffee shop to the (random) nice woman sitting next to him. She told him that what he needed in his coffee shop were ice pops, gourmet ice pops in the Mexican style. Stephen listened as she explained that paletas (Spanish for ice pops) could contain anything from cucumbers to fresh pineapple to jalapeños.
With his interest piqued, Stephen returned to Montana to finish the winter ski season. He bought a set of cheap plastic ice pop molds and spent his evenings trying different combinations of flavors (as there is nothing to do in Montana after dark) and let the guests at the hotel try them and give feedback. When he came back to St. Augustine in April he had enough money saved to buy some semi-industrial ice pop molds and pay first and last months’ rent on a little retail space in downtown St. Augustine.”
A novel-worthy beginning for the official story of the Hyppo’s beginnings, to say the least. Small town Florida boy moves to Montana to work at celebrity ski lodge out West, meets his random muse on an airplane who gives him the inspiration of a lifetime, then gambles his life savings to start selling gourmet popsicles back home on the oldest streets in America. At the height of the Obama Recession, no less. But it is exactly the slow economy that provides the catalyst for his early success. There were not many brave souls starting from-the-ground-up businesses during that bleak time period. But Stephen DiMare was a brave soul, and he rolled the dice and bet the house on popsicles.
The slow economy had made available several spots in the busy tourist area that otherwise would have been out of the league of someone starting with so little. The shop opened for business on June 5 after lots of support from friends and family volunteering to paint and hauling freezers (up stairs, no less!). Despite a hilarious string of experiments and missteps trying to figure out larger-scale popsicle production, Stephen eventually succeeded in meeting demand (although many nights were spent sleeping on the floor at the shop).
As I sat there at Hyppo HQ, speaking with Stephen and hearing this story first hand, I was struck by how quiet and unassuming he was. I had figured that someone who was as successful as he is would be a highly-wound, highly-caffeinated, 24 hour a day on-the-go person who couldn’t sit still long enough to be interviewed. But he was low-key, quite humble, and very easy to talk with.
Here’s a funny story: We were talking about various things having to do with downtown Saint Augustine, and the subject of Cousteau’s Waffle and Milkshake Bar came up. That’s another place my kids and I love to go. So I said to him, “I love that place, amazingly good waffles with lots of cinnamon!”. To which Stephen replied “thank you”. Huh? Why is he saying “thank you” for what I said about the waffle place? As it turned out, Stephen owns Cousteau’s Waffles. And not only that, Cousteau’s Waffles storefront is the very place that Hyppo Pop first began selling its gourmet fruit-infused popsicle! We had a good laugh over that revelation, and my admiration for his business style deeped.
The more we talked, the more his passion for popsicles came through. He didn’t seemed to be as focused on the business end as much as he was on the customer experience end of things. Stephen truly loves operating the Hyppo, and spares no expense to produce the finest popsicle possible. His employees are very loyal, happy people who enjoy coming to work each day. That’s something I saw not just in the interview but as a customer for the past 6 years. Stop in to any one of his stores and talk with the people behind the counter, you will see that they are truly shiny, happy people.
Six years and millions of popsicles later, Stephen DiMare is not resting on past success, but looking forward. He told me of the aggressive expansion the Hyppo is doing within the state of Florida, as well as the plans for possible branching out to a few neighboring states as well. I have brought a lot of people when they come visit me in Florida to the Hyppo for a pop, and the reaction is always the same. They don’t just enjoy, the love it and love the experience that comes with purchasing the pop.
As a businessman, Stephen is absolutely one of those people whose friends will say “I knew him when” after the day comes when Hyppo Pops are sold in every supermarket in America. And as a person, he is just a lovely, caring human being completely deserving of all the success he is having. He’s one of the “good guys”. His “secret for success” is doing something he’s absolutely passionate about, and doing it to the utmost of his ability.
As the interview concluded, I pitched him my idea for a new pop flavor – Root Beer and Cream! Immediately he got a twinkle in his eye and starting running through the various roots and natural flavorings he could use to make it. He promised me he would consider it.
So the next time you’re in a Hyppo shop, ask the person behind the counter for the Root Beer and Cream pop…and see what they say.
One of these days it will be there, I just have a feeling. Stephen is just that kind of guy.
The Hyppo Cafe
1765 Tree Blvd. #5
St. Augustine, FL 32084
Visit the Hyppo Pop website.