Is it Hip to Be Square? [When it comes to pizza, yes.]

5 Questions to Ask Before Buying Pizza Pans
February 2, 2022
3 Pizza Trends Coming in Hot
February 18, 2022

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. 

Photo by Five Squared Pizza

LloydPans spoke with Steve Kaplan, one half of the Five Squared Pizza family business. 

Talk us through the emotions of quitting your day job for pizza life.

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.

How did the initial process go?

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.

Your awards and accolades are very impressive. What do you think is clicking with the Chicagoland area, which is a huge pizza town?

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.

What sets your Detroit-style pizza apart?

Photo by Five Squared Pizza

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.

Where did you first hear about LloydPans?

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.

You got rid of the food truck and turned the business into a pickup and delivery model.

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.

How do you decide what’s going to make the ‘slide into the DM to order’ weekly menu?

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.

Delivery and pickup are each week until you run out? 

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. 

What other pizzas are doing well right now on the weekly rotation? 

Our top vegetarian sellers are Tie Dye and Burrata Caprese. And for our meat lovers, the top sellers are Cheeseburger and Big Red.

Photo by Five Squared Pizza

How do LloydPans help you achieve your weekly pizza making goals? 

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.

1 Comment

  1. […] we recently spoke to Steve Kaplan from Five Squared Pizza, he said that when making his ideal Detroit-style pizza, it has to be about […]