How this 27-year-old entrepreneur built his $8 million dessert empire after leaving Wall Street

• Neil Hershman worked as a Wall Street analyst in his early 20s.
• The entrepreneur left his job to pursue owning a 16 Handles shop.

Editor's note: This as-told-to essay is based on a conversation with Neil Hershman, 27. With the help of a business loan, the Wall Street analyst turned food entrepreneur bought a 16 Handles franchise in Manhattan in 2019. Taking advantage of a depressed real-estate market amid the pandemic, he negotiated favorable long-term leases and opened several 16 Handles locations. He bought the chain in August. He's also a Dippin' Dots and Captain Cookie franchisee/licensee. Here's how he created a dessert empire in less than three years.

This September conversation has been edited for clarity.

My name is Neil. I'm 27. I have dessert shops around Manhattan, including two Times Square flagships. Last month, I closed on the acquisition of 16 Handles, the frozen-yogurt and soft-serve franchise with over 30 units across five states.

I grew up entrepreneurial. I wanted to turn everyday activities into profitable businesses. There was one quote that I heard when I was younger about min-maxing your life, meaning solely focusing on the things you're good at, instead of trying to spread yourself too thin. That stuck with me and was the driving philosophy behind a lot of my achievements.

I became a master scuba diver at 14. I became a certified pilot at 17. At 26, I summited Everest.

I left finance and became the guy behind the froyo counter

I graduated from George Washington University in Washington, DC, with a degree in finance and astrophysics. I went to New York. I joined CIFC Asset Management as an analyst. I had the chance to get my feet wet with big money.

I loved the work. I was mainly in valuation, mergers and acquisitions, and strategic forecasting. But I couldn't stand the inefficiencies and lack of creativity. So I started to focus on my side projects. I was looking for a turnkey business to invest in.

I like selling physical things, and I thought, long term, the food business seemed like a great place to end up. I was living in the East Village neighborhood of Manhattan. 16 Handles was a froyo shop around the corner from my apartment that I frequented. It's a great product. The business had held its own for over a decade. I purchased my first 16 Handles in April 2019.

I left finance and became the guy behind the froyo counter.

I never introduced myself as the owner. I worked three straight months. It was all about learning the business inside and out — and a lot of that came from the employees who had worked at the store and never really had their voices heard.

Dessert — especially 16 Handles since it's a self-serve shop — is a high-margin, low-cost business. You have this broad customer base. I had a quick return, so I negotiated to buy two additional New York City downtown locations. That was April. The next two, I purchased in August 2019.

That's when the vision of this — a froyo and dessert empire — started brewing.

I saw this retail apocalypse as a great chance to sign leases

When the pandemic hit, New York City grinded to a halt.

Within months, we were able to get all my operating locations back open, with this big focus on delivery. Even though the streets of New York were empty, I saw this retail apocalypse as a great chance to sign leases with pessimistic landlords. I was able to get deals done — a young entrepreneur who's willing to bet on New York, taking prominent, convenient locations so that we had the best foot traffic.

I signed the 16 Handles Times Square store — 550 square feet on the ground floor — in the peak of the pandemic, maybe November or December 2020. Before that, all the 16 Handles were closer to 1,200 square feet. Building that store meant a new customer base because you're talking about the tourist market instead of a local neighborhood.

I never bought into the idea that New York City would never come back. The only thing that scared me was how long it could take.

Expanding the dessert delivery space with Captain Cookie and Dippin' Dots

During the early part of the pandemic, I was also thinking of ways to increase revenue and leverage the store-delivery solution for frozen dessert I had created to prevent froyo from melting en route to customers.

That was when I first thought about Dippin' Dots because I wanted to buy some myself. Googling how to get them, I learned that they were inaccessible and required special freezers for distribution — a problem I knew I could tackle. I reached out in August 2020 and worked with it to create the first stand-alone flagship retail shop in Manhattan's Flatiron District, which we opened to a two-hour line on April 9, 2021.

Captain Cookie is a brand that started as a food truck on my college campus and turned into a store. In a late-night email in November, I jotted to the Captain Cookie folks, "Hey, I build dessert shops in New York. This is right up my alley. I used to go to GW. I loved the product and the brand. Would you be interested in doing a partnership in New York City?"

That first Captain Cookie store opened in April.

After the success of the initial Dippin' Dots location, I built two more this spring, along with my first two Captain Cookie stores. By June, my nine dessert stores, including five 16 Handles shops, were all hitting their summer stride and on track to hit $8 million in annual sales.

Buying 16 Handles and growing it to a national brand

As the largest franchisee working with the franchisor, we were misaligned on what we saw as the vision for 16 Handles. So at that point, it made sense for me to put in an offer for the full acquisition of the brand.

I believed I could not only help my stores and help grow the brand but also help the other franchisees in the system. During the acquisition, there was an opportunity for me to take on two more 16 Handles locations, in uptown Manhattan, which brought my shop count to 11 (including Dippin' Dots and Captain Cookie stores).

The ultimate vision for the 16 Handles brand is to make it a large national player.

A key reason for my success with 16 Handles is that I found creative solutions to what otherwise seem like impossible obstacles. Instead of conceding or walking away when I heard "no" during a negotiation, I took some time to brainstorm.

When making deals, I consider what the other party's goals are and how I can sell them on an alternative solution and keep the deal alive. Sometimes all it takes is believing there's a solution and giving yourself the time to think of it.