How Jon Built Chicago’s First Pizza-Focused Food Tour

In this interview, we sit down with Jonathan Porter, the visionary founder of Chicago Pizza Tours, the city’s first food tour company dedicated entirely to pizza. Launched in 2009, Chicago Pizza Tours aims to offer both locals and visitors an unparalleled pizza experience by delving into the history, ingredients, and unique flavors that make Chicago’s pizza scene legendary.

With a rich background in small business and a passion for pizza, Jonathan shares his journey and insights, reflecting on the importance of pursuing one’s true calling.

Inspiration Behind Chicago Pizza Tours

SBS – What inspired you to start Chicago Pizza Tours?

Jon – There’s never really one thing that leads you to quit your job, buy a bus, and start taking strangers out for pizza. Admittedly, you have to be a little crazy, but I was in a sales job, and my clients were tied to construction. In ’08, the housing market crashed, and by ’09, just after the birth of my first child, I had lost all of my customers and was investing in real estate.

Pizza was always a huge part of my life, and the pizza landscape in Chicago was booming and evolving. I talked with my wife about it and told her that the URL ChicagoPizzaTours.com was available. She practically threw the credit card across the room at me and told me to buy it!

Selecting Pizzerias for the Tours

SBS – How did you select the pizzerias featured in your tours?

Jon – I wanted to showcase what Chicago was all about, which meant it had to touch on historic slices that had something to do with the deep-dish origin. I also needed a dynamite thin-crust tavern-style place, which was the bulk of pizza in Chicago. From there, I wanted to have another deep dish that could contrast the first one and an “off-the-wall” place that did coal-fired artisanal pizza to showcase what it was like to eat and live in the neighborhoods.

It was always about getting guests off the beaten path so they could see Chicago one slice at a time. I had an idea of which places I wanted to feature but also pooled many suggestions from lifelong Chicagoan friends and put them into a color-coded Excel sheet according to styles and neighborhoods, which only reinforced what I had in mind.

Initial Challenges in Launching

SBS – What were some of the initial challenges you faced when launching the business?

Jon – Where to begin? Well, for starters, hardly anyone knew what food tours were in 2010, and those who did weren’t exactly looking for pizza-centric versions. I spent most of my savings building a website, buying a bus, and all the other things that come with incorporating a small business, only to find out that the insurance for the bus I bought was as expensive as the bus itself yearly. That yearly fee was due upfront.

When we launched, I had nothing in the tank and legitimately needed to operate based on sales and not pay myself, all while having a one-year-old and two properties in my name that were both underwater. Between that and the bus I bought having problems like belts breaking, AC going out, and little things like that, I am surprised we made it through the first year.

Ensuring High-Quality Guest Experience

SBS – How do you ensure a high-quality experience for your guests?

Jon – I always figure anyone could steal this idea and do a version of the tour. In fact, in the first year I was in business, two other companies doing “pizza tours” also launched shortly after me. My goal was to become an absolute expert in pizza, with a focus on Chicago pizza, and give the guests the most complete information they could imagine. The guests were expecting tasty pizza, and I relied on the restaurants to provide that, but what I would provide was where the tomatoes were grown, who provided the cheese and what blend it was, what type of oven it was cooked in, and how different ovens were used for different styles. I provided answers to questions that guests never even thought to ask.

Organizing a Typical Pizza Tour

SBS – Can you describe the logistics involved in organizing a typical tour?

Jon – It depends on the type of tour we run. Some are walking pizza tours, and others are bus-driven pizza tours. We work closely with the bus company to know who our driver is, what time they will be there to pick us up, and if there is any delay. We work with pizzerias well in advance to let them know how many guests there are and what the approximate time is, and we place orders ahead of time so that everything seems seamless to the guests. It involves reaching out to vendors in the way they want to be reached out to, which could mean using a group text, calling a landline, or sending email days in advance. It is up to us to make sure that we communicate with our vendors and partners in the way they prefer.

Marketing to Locals and Tourists

SBS – How do you market your tours to attract both locals and tourists?

Jon – We primarily market to locals, knowing full well that the tourists are going to find us anyway. This tour was designed for people from Chicago to explore and see their own city through the eyes of pizza and its pizza culture and history. Social media is really more of an extension of our brand, but we use platforms like Instagram and LinkedIn to talk to pizza fans and communicate with the local pizza scene. As far as marketing to tourists, we have been members of Choose Chicago since we first started, and they are a good resource in addition to the usual Google and Trip Advisor for marketing to visitors.

Maintaining Relationships with Pizzerias

SBS – What measures do you take to maintain relationships with the pizzerias you feature?

Jon – These are the most important relationships we have. It took some time to win some pizzerias over, but we have always been their customer, not their partner. We pay for the pizzas, and we are friends with the staff and owners. When I walk into a pizzeria, not only do I know the owner well, but I give fist bumps to the managers, the servers, and the bussers, and I know them all by name. Often, when I am in a pizzeria, their regular customers will ask me questions, thinking that I work there, and I always give them an answer or find someone to answer their question if it is complicated. It may sound cheesy, but I feel like family with the employees of the restaurants we work with, and I mean it.

Managing Peak Season Operations

SBS – How do you manage the operational challenges during peak seasons?

Jon – To be 100% honest, it can get a bit hectic. We try not to turn away business while at the same time not overschedule ourselves. It’s a challenge that is at the top of my mind when booking and adding tours and dealing with giving employees time off. Most of our employees are very money-motivated and know that business ebbs and flows, so if you miss out during the busy season, it’s tough to get it back.

Advice for Starting a Similar Business

SBS – What advice would you give to someone looking to start a similar business in another city?

Jon – The one piece of advice I always default to is to be flexible. It really is something I have found can get you out of a jam. When you are so set in your ways, you might not stumble onto the obvious answer that may be a better process for you than what you were so sure of. I’ve had numerous problems surface with a route or order or something that could throw a wrench into the way we want to run something and the solution we come up with leads to improvement not just in that situation but in other parts of the company as well.

Staying Updated with Industry Trends

SBS – How do you stay updated with the latest trends in the food and tourism industries?

Jon – I worry less about the trends in tourism and more about the trends in pizza. Probably to a fault, but that makes me authentic, and the guests can tell. I work with UpLevel Tourism to host my website and do some CRM. They let me know when I need to do something to keep pace with the tourism industry.

Crucial Technological Tools

SBS – What technological tools or platforms have been crucial for your business operations?

Jon – Our reservation system and entire backend software owe credit to FareHarbor. This is now the third system that we have worked with after our initial partners went out of business in 2015, and then the second system went out of business during the pandemic. FareHarbor has all the tools we need to run the tours day-to-day, and then we implement other things like Slack or Discord for communication in addition to native apps on phones.

Future Plans for Chicago Pizza Tours

SBS – What future plans do you have for Chicago Pizza Tours?

Jon – Currently, I have the usual goals: offer more tours, offer types of pizza tours, hire more people, and grow responsibly. Honestly, though, the pandemic gave me a real opportunity to reevaluate what I want out of this company. I was on the path to becoming the largest food tour company in Chicago and had more than a dozen employees working for me, and I thought that we would just keep going. However, 2020–2021 really did a hard reset, and it was almost like starting up again when we came out of the pandemic. Honestly, I’m not entirely sure where I want to go with it, but wherever it ends up, my plan is to get there slowly.