Slide into DMs for a slice of @FiveSquaredPizza, and this is one message that won’t reject you. Quitting the corporate life to start a pizza making business is a big risk for most, but for Chicago-based Steve and Jenn Kaplan, it’s paying off in a big way with headline making pies. Customers can order Five Squared Pizza based off a weekly rotating menu by a simple Instagram direct message (don’t worry, you can still call the traditional way), and it’s a model that’s selling out like hot cakes — or in this case pizza.
LloydPans spoke with Steve Kaplan, one half of the Five Squared Pizza family business.
It was both scary and exciting at the same time. It was something I knew I wanted to do but always assumed it would come later in life, post retirement. An opportunity came my way much earlier than expected, and I decided to jump on it.
I had a couple of months off work and started with making a business plan, starting an LLC, and getting all necessary accounts set up. We then found a commercial kitchen and a food truck very quickly. We made pizza for as many people as we possibly could, to get their opinion. Everyone loved it, and we knew we had something special. It took us three months to go from concept to our first event.
Detroit-style pizza is fairly new to Chicago, and people love trying new things. People love the variety that we offer and the ability to get multiple flavors per pizza box. People also appreciate the fact that we use organic ingredients and make all pizza/toppings from scratch.
We use organic flour, cheese and tomatoes for our pizzas. Our crust is very crispy, fluffy and chewy, all at the same time. Our business model also sets us apart by having people heat up the pizza at home. This allows them the flexibility to eat it when they want and to have hot pizza straight out of their oven.
I was searching for a 10-inch square pan, and LloydPans was the only company that carried them. I started researching the brand and came to learn that it was a highly reputable manufacturer used by all the top pizzerias.
At the time, logistics with the food truck were getting tough, so we pivoted and took advantage of the pandemic when everyone was at home and ordering out. We don’t attempt to deliver hot pizza, and we never wanted to. So many factors are out of our control. We want our customers to have the best experience when eating our pizza, and we found that the best way to do that is to have them heat up the pizzas at home.
Lots of taste testing! I keep a running list of ideas, and every month we introduce two new items. If they are successful throughout the month then we keep them on the menu and rotate other ones out. We like to keep a fairly even mix of vegetarian and non-vegetarian options.
That’s right! As a small operation we have a limit on how much the two of us can produce in a week. We open up the ordering window on Monday to allow people to pre-order. We typically are selling out by Friday night for the entire weekend.
Our top vegetarian sellers are Tie Dye and Burrata Caprese. And for our meat lovers, the top sellers are Cheeseburger and Big Red.
They are just incredible! They are easy to clean, super non-stick. They are extremely durable and have been through MANY bakes without any wear and tear.