Finding a niche making, serving frozen treats

From its factory in St. Augustine, Stephen DiMare’s company makes the ice cream and ice pops sold in his shops.


  • By Dan Macdonald
  • | 3:40 a.m. August 15, 2022
  • | 5 Free Articles Remaining!
Stephen DiMare started The Hyppo Gourmet Ice Pops in 2010 in St. Augustine, launched Cousteau’s Waffles & Milkshake Bar in 2013 and Mayday Handcrafted Ice Creams in 2018.
Stephen DiMare started The Hyppo Gourmet Ice Pops in 2010 in St. Augustine, launched Cousteau’s Waffles & Milkshake Bar in 2013 and Mayday Handcrafted Ice Creams in 2018.
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Stephen DiMare thought that he had a hot business idea but opted for one where he is making cold hard cash.

After leaving the University of Florida in 2009, DiMare, 36, wanted to open a coffee shop. 

With the economy in a recession he saw small local operators closing their doors. 

He wasn’t so confident to think he would make money where others were failing. 

Frozen dessert was a niche where DiMare saw an opening. He now owns three businesses in that cool space.

In 2010 he started The Hyppo Gourmet Ice Pops. In 2013, he opened Cousteau’s Waffles & Milkshake Bar. Mayday Handcrafted Ice Creams followed in 2018.

At any one time, the Mayday stores have about 24 flavors.
At any one time, the Mayday stores have about 24 flavors.

Expansion happened quickly. 

The Hyppo Gourmet Ice Pops has five locations in St. Augustine, Tampa, Gainesville and St. Petersburg. 

There is one Cousteau’s Waffles & Milkshake Bar in St. Augustine with a second opening on Anastasia Island in the coming weeks. 

Mayday can be found in nine locations in Jacksonville, Jacksonville Beach, St Augustine, Lakeland and Tampa.

At Mayday, DiMare established old-fashioned ice cream and confections shops. 

The pandemic forced him to adapt to modern sales methods and his cold desserts can be delivered locally by Uber Eats, DoorDash, Bite Squad and Grubhub or ordered by the box online.

DiMare acknowledges his product is expensive. Fresh fruit, rather than concentrates and powders, are used to create ice pop and ice cream flavors. He said the ice cream uses the richest butterfat allowed – 16%. 

Any higher and he’d be making flavored butter rather than ice cream, he said.

Customers recognize that they are paying above the price of grocery store brand ice pops or ice cream treats. 

He said Starbucks may have had a hand in convincing customers to pay higher prices for what was once a rather inexpensive product.

Special to the Daily Record The company uses fresh fruit, rather than concentrates and powders, to make The Hyppo Gourmet Ice Pops.
Special to the Daily Record The company uses fresh fruit, rather than concentrates and powders, to make The Hyppo Gourmet Ice Pops.

“Starbucks created a reason for people to care about their coffee and they would pay for it. They opened a huge food sector of people who will pay for quality,” DiMare said.

Shipping his product also is expensive. 

The frozen treats have to be packed in thermal boxes in about 10 pounds of dry ice. The companies also absorb the two-day shipping costs, which for such heavy boxes can be considerable.

Because Mayday is a private company, DiMare will not disclose sales or profit margins. However, he did say revenue has doubled over the past 18 months. 

He credits that to opening several new stores as the coronavirus threat dwindled.

“We have seen significant increases over 2019 and that has been surprising. We are very grateful,” he said.

The company has 160 employees, with 12 in the St. Augustine-based factory making ice pops and ice cream. It has expanded to employ two off-site packaging companies to meet demand. 

It’s a seasonal business with November through January being slow. However, Florida trends differ from those in the other states when ice cream sales fall in the winter, he said.

Also, as much as 75% of sales come after 6 p.m. with families out for a treat or couples on a date night.

The names of his brands aren’t happenstance.

Mayday Handcrafted Ice Creams at 725 Skymarks Drive near River City Marketplace. The chain has seven locations in Northeast Florida, one in Tampa and one in Lakeland.
Mayday Handcrafted Ice Creams at 725 Skymarks Drive near River City Marketplace. The chain has seven locations in Northeast Florida, one in Tampa and one in Lakeland.

The Hyppo Gourmet Ice Pops comes from the first store in St. Augustine, which was on Hypolita Street. 

It also turns out that St. Augustine did much of his writing in an area known as Hippo in Northern Africa.

Mayday Handcrafted Ice Creams recalls the days in World War II when the Flying Fortress bombers flew to such altitudes that the temperatures inside the airplane were below freezing.

Fliers took advantage of their plight and placed the ingredients in buckets to make ice cream while on missions.

Cousteau’s Waffles & Milkshake Bar pays tribute to oceanographer and explorer Jacques Cousteau.

At any one time the Mayday stores have about 24 flavors. Larger locations may have more because of bigger display cases.

Every quarter four to six specialty flavors cycle on and off the menu.

The stores inform customers of the changes ahead of time so they can stock up.

“We are not spending a long time getting the flavor right. It’s mostly just a bunch of people trying to figure out what tastes best. It’s fun being in those meetings,” DiMare said.

One of the most important ingredients is imagination, he said.

DiMare said his two top sellers are Cookies Crush, which is Mayday’s version of cookies and cream, and Parent Trap, which is peanut butter and ice cream. Both contain Oreo cookies.
DiMare said his two top sellers are Cookies Crush, which is Mayday’s version of cookies and cream, and Parent Trap, which is peanut butter and ice cream. Both contain Oreo cookies.

Members of the 12-person production team gather to share ideas. Customers want craft ice cream that not only is sweet but has texture. 

DiMare said his two top sellers are Cookies Crush, which is Mayday’s version of cookies and cream, and Parent Trap, which is peanut butter and ice cream. Both contain Oreo cookies. 

Eight of the top 10 favorites include Oreo cookies.

Liquor is a popular flavor. The Cold Fashioned is cherry sorbet made with orange peel and bourbon. 

All items containing more than 0.5% alcohol by volume are not sold to minors.

He said those do not make an immediate impact anyway.

“You’d be filled up and be dealing with intestinal issues before you’d feel anything,” he said.

Each store makes its own sprinkles and waffle cones. 

A former staff baker created the sprinkles as little candies from fresh meringue.

He said other stores use factory sprinkles that can be years old.

“It is what differentiates us. The ice cream underneath is just as special,” DiMare said.

The fresh waffle cones are part of his childhood.

Growing up in St. Augustine, after school DiMare would walk to Kilwins Chocolates and order a freshly made waffle cone.

No ice cream. Just the cone.

“We want to be a proper ice cream shop and we wouldn’t be one if we didn’t make our own cones,” DiMare said.

“The smell is fantastic.”

 

 

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