This Guy Turned a Stranger’s Sweet Suggestion into a Popsicle Empire

Stephen DiMare, founder of Hyppo Popsicles, got the idea from a stranger who suggested he start a gourmet popsicle business. They churn up to 30,000 popsicles a week. Christie Post and Hector Velez/The Penny Hoarder

Three months.

That’s how long it took Stephen DiMare to transform a stranger’s suggestion into a business.

Armed with a history degree from the University of Florida, DiMare knew he wanted to start a business — perhaps open a coffee shop. He was 24 at the time.

However, he met a woman on a plane who changed his mind. And the rest? Well, it’s his favorite subject: history.

Now DiMare is 30 and the founder/president/mascot of The Hyppo, a gourmet popsicle store.

He oversees eight Hyppo flagship stores in Florida, with two more under construction. The sweet treats are also sold in more than 40 grocery stores.

How the Idea of the Hyppo Popsicles Popped Up

Stephen DiMare, founder of Hyppo Popsicles. Heather Comparetto / The Penny Hoarder
Stephen DiMare, founder of Hyppo Popsicles, got the idea for his business from a stranger who suggested he open a gourmet popsicle shop. Heather Comparetto / The Penny Hoarder

Back in 2010, DiMare lived in Montana and worked a seasonal gig at Big Sky Resort.

One weekend, he boarded a flight back to his hometown of St. Augustine, Florida, for a wedding.

On that flight, he found himself talking to the stranger next to him. Her name was Leslie. They’re connected on LinkedIn now, but he’s not sure she knows exactly how much of an influence she was to him.

DiMare shared his dream of opening a coffee shop with Leslie, who told him about some women in Nashville who make gourmet, Mexican-style popsicles. She suggested he sell something similar in his coffee shop.

His first thought?

“That’s not really my theme,” DiMare remembers.

But as he started thinking about the closure of small coffeeshops due to the recession, he knew it was risky. Instead, the idea of popsicles seemed new and fun — and the marketplace for that product was not saturated.

Really, it only took DiMare a few short hours to nix his year-long dream of a coffeeshop and replace it with something completely unknown: popsicles.

“It’s true,” DiMare says. “I think a lot of times people are like, ‘Oh, I just kind of got this idea.’ For me, it was very discrete.”

Building a Business in Three Months

Just a small selection of popsicle flavors. Heather Comparetto / The Penny Hoarder
A selection of popsicle flavors are displayed inside Hyppo Popsicles in St. Petersburg, Fla. Heather Comparetto / The Penny Hoarder

The simplest way to describe the process is “very fast.”

At this point, DiMare had a month left before his seasonal gig was up. When he returned to St. Augustine, he already knew the popsicle shop would be his next adventure.

His first task was to find a storefront. Note this was in 2010 — and the middle of the recession. However, DiMare used this to his advantage.

“You have landlords with prime real estate who are willing to rent to someone with no credit history,” he says.

He found a space in downtown St. Augustine — a high-traffic area with kitchen equipment already included. The 650-square-foot space cost $2,600 a month.

His parents chipped in to help out.

“They were very supportive, but were like, ‘If you fail, this will be a great failure for you. You’ll learn from this, and it won’t cost that much, so here you go,’” DiMare says.

He faced all the growing pains of a first business: How do I form a corporation? How do I get a sales tax filing number? How do I open a bank account?

Many nights, DiMare slept in his shop — sometimes simply curling up on the wood floors for a few hours. He ate about 8-10 popsicles a day.

How Does One Become a Popsicle Expert?

DiMare, right, talks with Penny Hoarder writer, Carson Kohler, at his shop. Heather Comparetto / The Penny Hoarder

Another challenge? DiMare had never made a popsicle.

He looked to the internet as a primer. Then, it was total experimentation.

DiMare describes some of the popsicles from the early days as “not awesome.”

“I was really bent on being authentic, so, for a key lime popsicle, for example, I got back there with a spoon and scraped out the insides of a ton of limes,” DiMare says. “It came out crazy bitter. We didn’t have many popsicles to sell then, so we sold them as ‘The Key Lime Experience.’”

Don’t worry — he says he’d never do that today. But back then, he relied on a whole lot of feedback. He’d log each recipe in a book and work from there.

Today, he has a team of seven pop makers and master pop makers (none have food backgrounds) who experiment to create the frozen treats from fresh, Florida-grown fruits. Currently, the team churns out 20,000 to 30,000 pops a week.

The store’s featured more than 500 flavors, including avocado coconut (smooth and creamy goodness), pineapple cilantro (a flavor DiMare admits he never thought would work) and jackfruit (a pesky fruit that has actually paralyzed DiMare’s hands).

Looking Back on the Early Years

Carson eats one of Hyppo Popsicles’ tasty pops. Heather Comparetto / The Penny Hoarder

For the past six years, DiMare has been a single guy living with his parents. He’s put every spare dollar he doesn’t need for food back into his company.

And it’s worked. The business’s revenue has been growing at an average rate of 76% per year in the past six years.

But it wasn’t always like this. DiMare still remembers when the first Hyppo location opened (on Hypolita Street, by the way) in St. Augustine.

“I remember just sitting behind the counter being like, ‘I’m stuck here; I’ve spent the last three months building this beautiful prison for myself, and now I can’t leave,’” he says.

Luckily, his first customer came in 10 minutes later, and the feeling left — never to return again.

For DiMare, his initial goal was to not fail too quickly.

“You can’t spreadsheet the risk out of the equation,” he says. “You just have to get your hands dirty and roll with the risk.”

Luckily, he overcame the risk. However, he’s had some other businesses fail, like a macaron shop. But he’s OK with that.

“You’ll figure it out,” he says. “Or you won’t, but a year from now you can move on to the next thing. You won’t be in limbo.”

But DiMare is happy he hasn’t had to move on or stumble in limbo. His empire continues to grow in Florida — where popsicle demand is strong year round.

So if you live in this steamy state — or the next time you take a beach trip — stop by one of the The Hyppo locations. The gourmet pops go for $3.75.

DiMare’s favorite flavor is — well, he doesn’t have just one. Mine? I enjoy the watermelon hibiscus. The dark chocolate-dipped key lime pop also comes with high praises.

Warning: A brain freeze is inevitable.

Your Turn: What’s the wackiest yet tastiest popsicle flavor you can think of?

Carson Kohler (@CarsonKohler) is a staff writer at The Penny Hoarder. After recently completing graduate school, she focuses on saving money — and surviving the move back in with her parents.