The Real Estate Empire Launched with a Cookie

Peter Phillips remembers walking into his father’s office with an announcement that would change his life. He was 28, had saved up some money from his real estate company, and was ready to reveal his next move: opening a cookie shop in a tiny Astoria storefront – with $70,000 and a high school friend. His father laughed at him.

“Now he is obviously very proud of everything that the company has become,” Phillips says. What started as that laughable idea in 2017 has grown into Chip City, now with over 50 locations across ten states, $17.5 million in investment from Danny Meyer’s Enlightened Hospitality, and hundreds of thousands of cookies served weekly. Add Somedays Bakery (launched 2024) and Massi’s Sandwich Shop (2025) to the roster, and Phillips has quietly built a multi-brand bakery.

With Tyra Banks, doing cookie-forward Hot Ice Cream flavor collaboration with her brand SMiZE & DREAM.

But this isn’t a typical tech-bro-scales-fast story. This is about a guy who knew how to negotiate a lease and build out a space, who understood that gas pizza ovens and fryers would kill any hope of scaling, and who figured out that electric convection ovens and cookies were his ticket to something bigger.

Phillips’ background in construction and real estate shaped everything about how Chip City was built. “Over the years working in real estate, from the landlord side and the broker side, I knew that it was very difficult to scale concepts that required vented spaces,” he explains. “Anything with gas—pizza ovens, fryers—you need a full ANSUL [fire suppression] system in the store. It can become a very costly and difficult endeavor.”

So he chose cookies. Cookies could run on electricity alone. No ventilation requirements meant more locations could open faster and cheaper. It’s the kind of practical thinking that separates businesses that scale from those that usually stay stuck at three locations.

His friend Teddy from the diner business joined him, and they landed on cookies partly because their first location was only 250 square feet. “It was also like a matter of what we fit into this space,” Phillips said. “You had to be really targeted and very specific to one item.”

The growth sounds clean on paper. One store to 50 plus. But Phillips doesn’t sugarcoat it. “At one point, we opened 34 locations in like a span of two years. It was almost every other week that we were opening a store. Not an easy thing to do.”

Another Chip City Cookies opening.

How do you pull that off without imploding? Phillips points to two things: building a team of people he had relationships with throughout his life, and sharing equity. “I created a lot of equity opportunities for a lot of people. That way we were all kind of aligned; we had the same goal because the upside was in it for everybody.” The corporate team now sits at 20-25 people. Total employees across all brands are around 500.

But scale without soul is just logistics. What’s kept Phillips sane through opening 34 stores in two years comes down to something he learned the hard way: you can’t fake authenticity.

With his team that means radical transparency, especially when you’re building businesses with friends. “When you have personal friendships tied into running a business, it can get really messy. You have your emotions as a friend, but then you have to put on your hat as a leader.” His solution? Explain every decision, take emotions out, do what’s best for the company. It’s not always comfortable, but it’s honest.

With his product it’s the same philosophy. At Somedays Bakery, everything’s made from scratch. At Massi’s, they fry in beef tallow. Chip City’s core cookies use high-fat butter and minimal ingredients. “It’s very low on the amount of ingredients. Customers can taste when you’re cutting corners, and they remember when you don’t.”

That honesty paid off in ways Phillips never expected. When Ryan Seacrest posted about Chip City cookies unprompted on Instagram, Phillips was floored. “We couldn’t even afford a collaboration like that,” he said. It was completely organic—the kind of moment you can’t manufacture, no matter how much you spend on marketing.

Phillips keeps expanding, Somedays Bakery is heading to Philadelphia next, but the motivation has shifted. He’s not chasing scale for scale’s sake anymore. He’s not building a dynasty for his kids to inherit, either. His father didn’t hand him a business. He won’t either. “I’m a big believer that people should go out and do their own thing in life,” Phillips says.

What he is building is simpler: a company that provides satisfaction. “It’s great to be part of a business that makes people happy and brings a smile to somebody’s face,” he says. “What a great way to make a living.”

Nine years ago Phillips started with some money he had on the side and a dream. Now, with 500 employees and three growing brands, Phillips has proven something his 28-year-old self probably knew all along: making people smile isn’t just good for the soul. It’s a sustainable business.