How Emmy Squared Went From One Brooklyn Spot to the World

The few lucky enough to score a seat came to Emmy’s for a host of reasons: a family dinner, a birthday party, a date or maybe a night away from the kids. But, without fail, these patrons chow down on Emmy’s famous Detroit-style slices: a thick, focaccia-like crust topped with fresh sauce. Pizza haters can dig into the Le Big Matt burger — a meal so juicy it would rival the lifesaving cheeseburger in “The Menu.” (Plus, it’s got the right amount of kick for Park Slopers.) 

What brought these diners out on a weekend so cold the city issued an emergency travel advisory? It’s the same thing that’s helped propel Emmy Squared from one location in 2014 to 21 across seven states in 2023: good pizza, and even better ambience. 

“Emmy Squared got their quality right and their hospitality right,” said Phil Colicchio, the executive managing director of Cushman & Wakefield’s specialty food and beverage unit. “Sometimes going into a pizzeria can be as intimidating as going into a high-end cocktail bar [but] everybody feels comfortable [at Emmy Squared].”

Under the now recognizable blue awning of Emmy Squared’s Park Slope location, candles light dark wooden tables as friendly wait staff circulate throughout the cozy eatery. That homey atmosphere is something Howard Greenstone, the CEO of Emmy Squared’s parent company Pizza Loves Emily, has tried to replicate nationwide. 

“No two of our restaurants look alike,” Greenstone said. “While we have a lot of restaurants, we pride ourselves on taking a page out of Brooklyn in that each one has its own individual entity. From a design, look and feel, we want to be part of the neighborhood no matter how large or small we want to be.”

After getting involved in 2016, Greenstone raised money to open roughly five locations each year from the profits of Emmy’s existing outposts, he said. Each location cost between $500,000 and $750,000 a pop. Last year, two private equity firms bought shares from Emmy’s existing investors — Greenstone, founders Emily and Matthew Hyland, and partner and entertainment manager Ken Levitan — to grow faster. Greenstone declined to disclose the price of that investment. 

Greenstone plans to open between six and eight restaurants in 2023 in Athens, Ga., Birmingham, Ala., a new ghost kitchen in Philadelphia, and is considering Miami, Chicago and Washington, D.C., he said. 

But Emmy Squared started small, with just one location in Clinton Hill, Brooklyn, in 2014. Emily Hyland, the chain’s namesake, and her then-husband Matt Hyland served up thin-crust, drier New Haven-style pizza before stumbling on square-shaped, deep-dish Detroit pies only after opening their second outpost in Williamsburg in 2016.

The duo had some restaurant experience. Matt Hyland had attended culinary school at the Institute of Culinary Education and worked at the restaurant Sottocasa in Boerum Hill, Brooklyn, where he fell in love with pizza, Emily Hyland said. But the duo weren’t businesspeople, and running the eatery proved to be a 24/7 job, Hyland said. 

“It was amazing and the most challenging thing I’ve ever done,” Hyland said. “There were moments in the middle of a two-hour waitlist where I would look down the span of the dining room and see Matt in the copper glow of the oven, cooking the pizzas and making this beautiful food, and know all of the regulars coming into the dining room and their kids and their families, and it was a really sweet, special slice of our lives.”

When Greenstone approached the duo in 2016 to grow the business, Hyland wasn’t sure about an expansion. Greenstone wasn’t the first investor to approach her, but the two uncovered a surprising connection: Hyland had babysat Greenstone’s nephews growing up in New Jersey. The moment felt like fate, she said. 

“When we made that connection, he remembered who I was as a little kid, and that really reaffirmed that this was the person I wanted and felt like I could trust, because our restaurant is so rooted in family and in our history together,” Hyland said. 

Greenstone, who managed the upscale Scandinavian joint Aquavit in Midtown East and served as CEO of the Gotham eatery Rosa Mexicano, saw a high-quality, unique pie he could reproduce across the U.S., he said. And after his first bite of a triple pepperoni slice, he was hooked. 

“It’s sort of like Sicilian pizza to me but a little more dynamic with the frico crust,” Greenstone said. “I grew up in Teaneck, N.J., and there was a place that served Sicillian pizza, but it might as well have been a lead weight. And this was light and airy and delicious.”

Greenstone now runs the business with the Hylands as equity partners, and he helped it weather the pandemic without permanently closing any of its locations. Since he came on board, Emmy Squared has grown from two to 21 locations, scored a deal to serve its hamburgers and sandwiches at the golf club Swingers in NoMad, and licensed the restaurant to an independent operator in Abu Dhabi and to hospitality group Cool Inc. for two locations in Saudi Arabia. 

When Greenstone first started expanding the business, he focused on markets New Yorkers often traveled to, so news of the new eatery could spread. Today, he says he’s considering growing the business broadly in more residential neighborhoods near cities large and small, such as Chicago, Asheville, N.C., and Greenville, S.C.

Greenstone said he looks for second-generation restaurant spaces of around 2,500 square feet so he can get restaurants up and running quickly. And residential enclaves near populous cities tend to have local traffic as well as some tourism, keeping Emmy a neighborhood spot while also letting visitors chow down on Emmy’s chicken sandwiches, slices and burgers, he added. 

Those meals have drawn guests and stellar reviews. Emmy Squared’s second outpost in Williamsburg scored a write-up in Condé Nast Traveler, Eater lauded the location’s Detroit style in 2016, and Bon Appétit praised its sandwich offerings. While its pizza is doughy and delicious, the unexpected showstopper at Emmy Squared is its burger — a juicy, meaty medley of flavor that will leave plenty of grease on your plate and joy in your heart. 

But its grub doesn’t come cheap. The delectable Le Big Matt burger costs $26, and its cheesy square pizzas range from $18 to $28. Not everyone wants to cough up that kind of money for a dish they can get on the cheap, which is one of the reasons Emmy has likely been very intentional with its real estate expansion, said James Cook, JLL’s North American director of retail research, who is not involved in Emmy Squared’s business.

“That’s New York pizza prices, so there’s not that many neighborhoods across America that can support that,” Cook said. “It looks like they’re choosing locations that are not just your typical corner fast-food location, but a high-trafficked area that’s going to have both folks that are already there plus other folks that are coming to the destination.” 

New Yorkers can get pizza for as low as $1 a slice, though thanks to inflation a $1.50 floor has become the norm at a handful of pizza spots of late. Even the more upscale options are overwhelming, from Rubirosa’s famed tri-color slice in Nolita, to the nearly impossible to get into Una Pizza Napoletana on the Lower East Side, to Williamsburg Pizza in both Manhattan and Brooklyn. 

By making a name for themselves in Gotham, Emmy Squared proved the power of its Detroit-style ’za, Colicchio said. (Colicchio is not currently involved in Emmy Squared’s business, though he did previously advise a client, Nashville W Hotel Investor Mark Bloom, on bringing an Emmy Squared to the city.) 

“I often wonder, as I think most New Yorkers do when they see a commercial during a football game from a pizza football chain, ‘Who would eat that?’ We’ve been blessed with such great pizza on every corner.” Colicchio said. “Emmy’s, I think, has earned its credibility, earned its bona fides in a town where if you don’t put good pizza out, you’re dismissed.”

Emmy Squared is not alone. Roberta’s Pizza, a Neapolitan joint started in Bushwick in 2008, expanded nationally to L.A. in 2018. But, unlike Roberta’s, which The Infatuation reports lost some of its original flair, Emmy’s stayed true to its roots. 

“The idea that this is a cheerful place to be creates a bit of an addictive ingredient,” Colicchio said. “Gosh, if I can get good pizza and the people are nice and welcoming? I feel like I’ve hit a home run.”

For any restaurant, there’s always a risk that expanding will come at the cost of the eatery’s original flavor, Cook said. But so far, Emmy Squared has opened enough outposts in markets with an affluent customer base to support its business, without opening so many that the restaurant feels like a chain, Cook said. And Greenstone hopes to keep expanding, without sacrificing quality.

“As we grow, a lot of companies dumb down what they’re doing, and we’re taking the opposite approach,” Greenstone said. “We’re leaning in and working to improve the quality of what we do. … We’re taking 2023 and 2024 to reinforce the core values and the culture of the company so we can come out stronger on the other side.”

Celia Young can be reached at cyoung@commercialobserver.com.