This City Is Crumbling

How cookies conquered New York.

Ooey, gooey, and extremely good for profits. Photo: Bobby Doherty
Ooey, gooey, and extremely good for profits. Photo: Bobby Doherty
Ooey, gooey, and extremely good for profits. Photo: Bobby Doherty

A decade ago, Kafi Dublin was considering her entrepreneurial options. She’d grown bored of a full-time, well-paying job with the city and was ready to venture out on her own — she just needed to figure out what she’d sell. “I was like, I need something that is recession-proof,” she says. “People eat when they’re happy, they like sweets, and they eat when they’re sad: That was literally my business plan right there.” She had no professional baking experience, but she still identified cookies as a product that met her criteria. At the time, fresh-baked cookies cost about $3 each. Dublin envisioned a bakery where they could cost $5. “I’m embarrassed to say, but I closed my eyes and just asked myself, ‘Who’s going to buy a $5 cookie in New York?,’” she recalls. “And then I literally said: ‘A rich white person.’”

In 2017, Dublin opened Gooey on the Inside on Christie Street. It became so successful that she was able to afford another dream: moving abroad, to London. The store itself doesn’t need her physical presence —all that’s required is to mix, scoop, bake, and sell a single, uncomplicated, universally recognized entity — though she was back in New York this fall, scouting locations for her second store.

Whenever that opens, it will join a New York bakery landscape that is much more crowded than it was just six years ago: Chip City, launched in 2017, plans to double its footprint from 20 stores to 40 in the next three months. Crumbl, the Utah import that has 800 stores across the U.S., made landfall in New York last year (a single store can turn a $350,000 profit in a year). Crumb, which is different from Crumbl, is a delivery operation. Insomnia Cookies and Milk Bar cater to the stoner set. Funny Face, Janie’s Life-Changing Baked Goods, Twins That Cook, Best Damn Cookies, Sofia & Grace Cookie Company, and Cookie Crumz are here too. So is Seven Grams Caffe, which originally launched as a coffee business; it found so much success with its “ooey-gooey cookies” that it will open its fourth store this winter in Soho as a cookie bakery that just happens to serve coffee too.

All told, cookies are pretty easy: “They are the least-regulated thing,” says Janie Deegan, the owner of Janie’s Life-Changing Baked Goods. “They have little to no risk of foodborne illness, and they are, for the most part, shelf stable.” They’re less labor-intensive than cakes or even cupcakes (which require an additional step of frosting and decorating), and they can be stored more easily: Many bakers stand by chilling dough overnight before baking, and once baked, cookies can be frozen without much hassle. It helps that they’re easy to photograph for Instagram, and that TikTok was practically invented to showcase gooey pulls of molten chocolate chips. But the real reason behind the boom is that an industrious baker can put a cookie shop just about anywhere.

Teddy Gailas remembers when he and a high-school buddy, Peter Phillips, were trying to launch Chip City: “Peter finds our first location and we go in there and it was tiny,” he says. “If the oven was an inch bigger, if the fridge was an inch bigger, Chip City might not have happened.” Last fall, Danny Meyer’s private-equity group, Enlightened Hospitality Investments, put $10 million into the company, which has expanded to Long Island and New Jersey.

“Any retail food business is all about the real estate — anybody who tells you otherwise doesn’t know what they’re talking about,” says David Liederman, who was a major player during the city’s last cookie boom, opening a prolific chain of stores selling warm cookies in the late ’70s and early ’80s. On the island of Manhattan alone, there were 20 David’s storefronts, but he sold the business in 1995 when, he says, the financial numbers stopped working in his favor. Rents were rising, and “I didn’t think people were going to pay, back then, $10 a pound for cookies.”

That was the same year Connie McDonald and Pam Weekes opened their bakery, Levain, on the Upper West Side. In 1997, Amanda Hesser wrote in the New York Times that the duo baked “what may possibly be the largest, most divine chocolate chip cookies in Manhattan. The fat round cookies, about an inch high and three inches in diameter, are packed with walnut halves and chunks of chocolate and weigh almost as much as a grapefruit.”

Those cookies — world famous about five minutes after that Times story was published — were six ounces and cost $1.75 at the time. Today, they cost $5, and they remain the gold standard for would-be cookie barons: “If anyone who starts a cookie business says that Levain is not the OG, and that they didn’t dip into their business plan or their environment — they’re lying,” says Dublin from Gooey on the Inside. “I have to give kudos to Levain.”

In 1999, before e-commerce, McDonald and Weekes established nationwide shipping for Levain’s then-famous cookies. They also expanded, slowly and deliberately, to Wainscott, New York; Harlem; and a new shop on Amsterdam Avenue. They waited another 23 years to seek out outside investors and embark on larger-scale growth: Since the beginning of March 2020, they’ve opened seven more locations (including those in Maryland, Boston, Los Angeles, and Chicago), with two more on the way, one of them in the Flatiron, bringing the total number of NYC outposts to eight.

Levain launched a grocery line in 2020 as well, but had to pause during the pandemic. The founders are planning to resume, but there’s no indication when. “Supermarkets are very much more complicated than opening an old neighborhood bakery,” says Weekes.

COVID also disrupted business at Sarah Silverman’s FunnyFace Bakery, which specialized in decorative cookies with recognizable designs (“Pizza Rat” and “Girl Dinner” designs are both accounted for). She was wondering whether she could stay in business and was entertaining any possible avenue for financial survival — “I was actually planning on going on Shark Tank,” she says — when good luck intervened: Some regulars who loved her cookies were also venture capitalists looking to invest. Together, they prioritized “building infrastructure around the increased demands of both the retail footprint and the growing online and commercial businesses,” says her silent partner (who wishes to remain anonymous). What that means in practical terms is they opened two new locations: One at the South Street Seaport and another in Noho — mere steps from a Levain.

Will our appetite for cookies ever be fully sated? Some bakers have discovered they don’t even need a physical shop to succeed: Maya Christian and her sister, Aria, are the co-founders of Twins That Cook. Together, they’ve parlayed the success of their online-only delivery business into appearances on Rachael Ray’s and Drew Barrymore’s daytime-TV shows. They’re still looking for a location for their first brick-and-mortar, but in the meantime, they’ve set up a West Coast headquarters in Los Angeles to help launch a lifestyle media brand. Cookies aren’t the end game, but they have so far been a useful tool to generate exposure: “It’s inexpensive compared to if you’re making cakes,” says Maya. “You can make a lot of batches of cookies with one bag of flour.”

How Cookies Conquered New York