Jessica Oloroso

Way beyond plain vanilla

Black Dog Gelato owner was inspired by exotic flavors of Rome

By Alexis Castanos


Black Dog Gelato is crawling with kids—big and little, eagerly awaiting a scoop of one of the eight frozen treats on display. The Ukrainian Village shop looks a lot like a typical ice cream parlor, with pink and white striped walls and wood tables. But the flavors are not the typical “ice cream” selections.

Although Blueberry French Toast and Goat Cheese Cashew Caramel are the flavors of the day, children leave the gelato shop with faces smeared with vanilla and chocolate.

Jessica Oloroso, the woman behind the magic, is the chef and owner of Black Dog Gelato. Oloroso founded the first brick and mortar shop in the Ukrainian Village neighborhood in 2010. Since then, Oloroso has expanded to another location in Roscoe Village, and now expanding her catering business.


Oloroso has an entrepreneurial streak a mile wide. In December 2014, Black Dog Gelato premiered a Gelato of the Month Club along with a date night series of gelato workshops. The workshops include snacks and refreshments while guests work with their significant other to create a new gelato flavor. When customers sign up for a Gelato of the Month membership, they receive two pints of a surprise gelato flavor delivered to their doors beginning in January and ending in May.

“We wanted to provide something sweet and perfect for the holidays,” Oloroso says. “This is a time when people are looking for holidays gifts and for sweet things to do if you’re a couple. This is one of the ways we are trying to keep our customers interested in us.”

But with Black Dog Gelato’s successes have come roadblocks. Four years into running the shop, Oloroso concedes it is often difficult to keep profits stable, especially during winter months. Months after opening in September 2010, Black Dog Gelato’s business dropped approximately 90 percent, something Oloroso hadn’t anticipated.

“When we first opened, I had no idea what to expect,” Oloroso says, sitting in the dimly lit, Ukrainian Village location before opening time. “Over these four years, we have learned to adapt. We’ve learned how to market the product in different ways so we can stay competitive throughout the year.”

Since 2010, Oloroso has added gelato classes, expanded the company’s catering business and continued wholesaling to restaurants. Black Dog Gelato supplies decadent dessert options to such places as the Hilton Chicago located in the South Loop to Girl & the Goat in the West Loop.

Because the food industry is constantly changing, Oloroso has learned to adapt.

“Everyone is waiting for the next big trend, and everyone is waiting for the next big food,” she says. “They say 90 percent of restaurants fail within the first five years, so just because I’m almost hitting our five years doesn’t mean that I’ll make it to six.”

It’s her passion for food that has kept Oloroso focused and motivated. At age 8, she started baking birthday cakes and other treats for her parents and brother. Her love for baking led her to attend Johnson and Wales Culinary School in Rhode Island, where she received a bachelor’s degree in applied IMG_2694science in baking and pastry.

Following graduation, Oloroso worked as a pastry chef at the World’s United Center in Chicago and moved on to be a pastry chef for Stephanie Izard’s restaurant Scylla.

“When she’d closed the restaurant, I was trying to figure out what my next step was,” Oloroso says. “I wanted to focus on carving out a niche for myself in the industry. I was making our ice creams in-house at Scylla. It was my favorite part of production day. I figured that if I was going to be working for no money, that it should be something that I’m building for myself.”

After graduating from high school, Oloroso had taken a month off and toured Europe. While roaming the cobblestone streets of Rome, she was struck by the gelato culture there. She discovered that for Italians, gelato wasn’t a treat, it was a part of life. She was inspired by not only what she saw in Rome, but also the flavors that she was introduced to, and she kept the idea of a gelato shop buried in the recesses of her mind. Gelato, she decided, could give her room to experiment and not stick with just classic flavors like vanilla or strawberry. When Scylla closed, it was a natural choice for her to create her own gelato business.

“When I was a kid making a cake, my thoughts were what can I use and what would mother let me buy,” she says. “As you get more comfortable with your craft, you start going outside your boundaries to create things. I too want to create, not to follow.”

Oloroso borrowed money from her grandmother, rented a shared kitchen space and set out to develop her own recipes. She created Black Dog Gelato as a wholesale company and had built up 12 accounts after two-and-a-half years in business. However, to make it a viable business option, she knew she needed a retail location.

She took over the former shop space of a Black Dog Gelato client who wanted out of the industry. The owners helped her with the rent and sold her the equipment.

Oloroso has learned from the mistakes she’s made since she began. For instance, she has opted to keep her second location in Roscoe Village closed during the slow winter season.

“When I went to open the second location, nothing went the way I thought it would, so it was a reality check,” Oloroso says. “Now, I’m focusing more so on expanding our catering portion of Black Dog.”

Black Dog Gelato catered 160 events in 2014, including weddings, private parties and bar mitzvahs.


When Oloroso first opened Black Dog Gelato, she spent 18- to 22-hour days making fresh batches of gelato while balancing a family life. Now, she has transitioned to a more administrative role, reining in her typical 80-hour-plus weeks to 40 to make time for her newborn daughter.

“The past year was the starting point for me transitioning into less kitchen and more recipe development, marketing, management and bookkeeping,” Oloroso says. “It’s difficult to try to maintain the balance of family and business. I waited until I was 37 to have my first child because I wanted to work on my career, and that was just the right time for me.”

Mike Schindlbeck, Oloroso’s husband, admires her dedication to both her business and her family.

“I have no idea how she balances family and work,” Schindlbeck says. “It must be pretty hard on her, to be honest. She’s a very busy individual trying to make a business work, but she does an amazing job. Family comes first for her, but there’s a lot of sacrifice that’s involved.”

Oloroso hired a head of catering and an administrative assistant this year to help manage her schedule and lighten her workload.

“Every day, I think about what business model is best for us,” Oloroso says. “I think that multiple locations are what we are trying to accomplish. We wholesale and cater. These are both directions that I want to expand on. I think that’s a huge market we could really have a large impact on, but we can’t just jump in. It’ll take time.”

Edited by Katherine Davis

Photos by Erica Garber

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