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Joseph Glesson, owner of Deeper Dive, an ice cream shop located Downtown.
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Inside of Deeper Dive ice cream shop
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Deeper Dive ice cream is located at 16 E. Main St.
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Mural inside of Deeper Dive completed by Ross Trimmer of Sure Hand Signs
Life has a way of jolting you into motion. For former chef Joseph Gleeson, the past five years have been an abrupt series of perspective-shifting events. He’s gotten sober, lost his father, underwent heart surgery and relocated to Richmond, all while finding his footing in an industry that he’s known but no longer felt attached to. The revelations have led him to his current less complicated foray, a route rooted in something simple and timeless with sprinkles on top: ice cream.
Last week, Gleeson opened Deeper Dive, a small-batch ice cream shop at 16 E. Main St. “I felt that ice cream was one of those things that I could have fun [with] as a cook,” Gleeson says, adding with a sarcastic smile, “I've had this or some form of this in my head since I was b****ing about doing dishes at my mom's house.”
With decades spent wearing an apron and working in kitchens, Gleeson’s culinary journey reads like a catalog of chapters that span from coast to coast. Bouncing between Montana and California as a kid, he recalls that as a teenager at home, he would take the reins in the kitchen to divert from dishes. His first real job was at a Hardee’s before he was drawn to the quirks of roadside diners. He's worked as a catering chef, attended culinary school in San Francisco, helmed a restaurant in the Puget Sound, spent years on Martha's Vineyard and staged with top-name chefs. In Chicago, he landed at One Off Hospitality Group’s The Publican and Big Star, along with Girl & The Goat. And his fine tuning came at a little gastropub called Hopfields in Austin where he worked for five years. He’s dabbled in Tex-Mex, fine dining, casual fare, and Moroccan and Middle Eastern food, and everything in-between.
For Gleeson, the appeal of debuting his shop is as much about freedom to play by his rules and philosophy as it is about ice cream, although the timeless treat is no doubt at its heart. Walking into Deeper Dive, a long hallway leads to the cold case and a marquee menu board. Along the way, shelves are stocked with children’s books like Shel Silverstein, cutesy chotchkies and Beach Boys memorabilia, and a jar near the cash register filled to the brim with Chick-O-Sticks.
Inside of Deeper Dive
While the shop's retail model is currently designed for Gleeson to be the main operator, he says that his wife, mother-in-law and daughter plan to be in the mix. His daughter, however, has one guise: "She told me, 'I'm only gonna do it if I can have a name tag,’" Gleeson says. Of course, she’s getting one.
Gleeson and his family relocated to Richmond after his wife took a job at the Virginia Museum of Fine Arts. After years spent helping open restaurants and bringing concepts to fruition, he felt ready to build something of his own — one that would let him set his own schedule, be present for milestones like his son's birthday, and away from the confines of a raucous kitchen. “Once I got sober, I was like, ‘I don't want to do this,’” he says.
In reference to opening his own business, he explains, “I'd rather have something that is coming to the direct benefit of my family and not somebody else's bottom line. ... Why do I have to worry about taking my son's birthday off."
The shop is inspired in part by places Gleeson encountered throughout his life, specifically Mariposa Ice Cream in San Diego, a multi-generational ice cream parlor he would visit with his wife and daughter when she was young. And Dixon Mercantile in Montana, a little restaurant only open on the weekends and always packed.
Gleeson says that Deeper Dive focuses on high-quality ice cream with minimal artificial ingredients, “Simple, clean flavors,” he says, “I like having fun.”
The lineup typically features nine to 10 flavors. While he doesn’t adhere to a standard base, the freedom to experiment has allowed him to dabble across styles. Opening flavors included a dairyfree brownie batter, an intensely rich chocolate lover’s dream that is essentially a chocolate sorbet; toasted sweet cream, which he describes as a perfect base for floats; mint chocolate chip, which churns fresh mint leaves with peppermint oil for a potent, herbaceous scoop; and horchata bursting with cinnamon. Peanut butter fudge is a chewy creation that comes closer to its namesake candy than traditional ice cream, and a flavor Gleeson suggests sandwiching between a housemade cookie.
A fruity “no-gum bubblegum” combines what Gleeson says is a “very specific ratio of banana, strawberry, orange, lemon and vanilla,” relying on fresh citrus and overripe bananas rather than heavy-handed extracts.
The wizardry comes to life in a back work station manned by a machine that makes tubs one at a time. Ice cream add-ons include housemade brownies and cookies, Virginia peanuts, sprinkles, caramel and hot fudge. Patrons can order scoops, sundaes, floats and sandwiches, and the drink menu features limeade, cold brew, iced tea, Mexican Coke and Cheerwine.
Not looking to reinvent the wheel, Gleeson says, “I just like clean good food, and I like to know where it comes from.”
“I think food should be accessible to everyone,” he continues. “I am trying my damnedest to either be the most inexpensive ice cream place in town or just offer a more personal experience.”
Of the name, he explains, “Deeper Dive was either a record store or an ice cream shop.” He points to art on the shop wall depicting a wild-haired child diving headfirst into a bowl of ice cream scoops with a cherry on top. “When I pictured Deeper Dive, I pictured that,” he says. His brother-in-law came up with a quick design and it was brought to life by Ross Trimmer of Sure Hand Signs.
Gleeson aims to have a personable shop, where people ask questions, maybe suggest a flavor, and get to know him by name. After decades spent opening restaurants for other people, he finally has a place that operates on his terms. And if customers leave with a scoop of ice cream and a brief escape from the day, that's exactly what he hoped to create.
“If I can be a little escape for people, that's what I want to do," Gleeson says. "I literally just want to be in here and let people chill and have fun."
Deeper Dive is open Wednesday through Sunday from 2 to 9 p.m.
