Jonathan Porter on How Chicago Pizza Tours Kicks its Own Pizza Butt


In 2010, back when I was at The Onion, I did a piece on what it was like to go on the then-brand new Chicago Pizza Tours. This was when food tours were still something of a novelty -- or at least pizza ones were. The business, started by owner Jonathan Porter, takes locals and tourists alike on an informative and also tasty trip to different hidden pizza gems scattered throughout the city. (It's also where I discovered my new favorite place still to this day, Pizano's.)

Roughly two years later, Porter is running Chicago Pizza Tours full-time (he didn't when we first met), and I thought it would be a good a time as any to check back in and see how his business is faring.

So, how's the pizza biz?

Jonathan Porter: I guess it's been a couple years, but I tell you, if I stop and think about it, it does seem like it was a long time ago. There were so many tours between when I ran that test one to now. It still feels like a startup to me everyday. And that's just because of the nature of the business, what I'm doing. It just seems to be evolving and changing nonstop. It's more like an adaptation to what's going on. The tourism industry in Chicago was already a fairly big market but these culinary tours that have started -- I think when I first started there was one or two other food tours out there and it seems to be now that there are multiple, lots more popping up, and even tours that were like a bike tour of Chicago, they've decided, "Well, why don't we stop by a pizza place and a hot-dog joint and throw a little culinary stuff into our bike tours?" I feel like everybody's dipping into it. I think it's great. I think it just promotes -- as long as there's good tours around showing good times, it promotes the consumer to go out there and explore more. Say that had a good time on the pizza tour, they're like, "You know what? I saw this other tour that features totally different foods in Bucktown and I had a good time with pizza, let me do this one now." And vice versa. There's competition out there, but if you can somehow create an environment that complements your competition it doesn't seem to hurt as much more.

It's just more potential customers?

Jonathan Porter: Exactly. It starts like a snowball effect, it gets them going. And now people are spending less time walking up and down Michigan Avenue, looking up at the sky walking two miles an hour and they're spending more time looking at really significant things in Chicago and eating really good food.

I don't know that, as a customer, it's made me more adventurous. I think I just go to Pizano's more often.

Jonathan Porter: [Laughs.] No, I remember, you really liked that one. 

But since I went on that tour to today, there's been a real rise of stuff like Groupon. It wasn't really as prevalent today as it was then. Has that impacted you guys at all? Have you done any group deals?

Jonathan Porter: That's a really good point, too. That really kicked off a whole bunch of things. I'm noticing more and more tours feature themselves on Groupon or LivingSocial or one of the local ones here, YouSwoop, that's one that I worked with as well. There's a good balance. It's hard to even believe that two years ago in 2010 you could call up Groupon and be like, "Okay, I've got this pizza tour and I sell it for $60 a ticket. Can we do a Groupon special for $30?" They'll get $15 and I'll get $15 and they'll go out and they were only sending one email out a day with one deal and they would sell like 3,000 in one afternoon. [Laughs.] I mean, you would have more customers than you even knew what to do with. Back then it was like the shiny-thing syndrome. Everyone was doing a daily deal and it was creating tremendous buzz about their business. I was fortunate enough that I decided I didn't want to go with a group as big as Groupon and I wanted to work with another startup, basically.

It was one of those things where if we weren't running it didn't cost us anything. We're not renting office space, I didn't have an expensive computer system and phone lines, all that. 

So you own the bus?

Jonathan Porter: Yes. That was actually one of the first purchases we made. I worked that in as one of my startup costs. And then I worked the insurance into the monthly costs because I figured I pay my car insurance, I can break it out every month or so. That one took me a little offguard. The insurance was almost as much as the bus was that first year. [Laughs.] And that was all due at the beginning of the year. So, basically, I had no month-to-month costs in the first year other than when I was running, but then I was behind the 8-ball because I owed myself a significant amount of money. By October of 2010 things really started to pick up. Enough people had taken it, enough people were finding it on Google or Yelp.

And then the second year, in the business plan stages I figured January through maybe mid-March I was going to just not do anything with the company. Just sit there and wait for the weather to get better and all that, but I decided to put my schedule up for Saturdays and Sundays and see what happens. What I found was I was getting more locals during the winter. People were just getting sick of the cold weather, sitting inside for months and months. But by May of 2011 we really turned a corner. I don't even know what happened, if it was just all the buzz about everything. This was before we were on 190 North, that ABC show. That was in June. But back then a good month would be taking out close to 60 to 70 people in limited runs. That'd be a good month there. The month of May, it was like 500 people in just that month alone. That kind of spilled over into June and July and August, 400, 600. Somewhere like that. Some tours were 40 people. It was just insane. I literally stopped counting after that.

You may need to get another bus or something.

Jonathan Porter: Yeah, I ended up putting a few more seats in our original bus here, which is nice. We went from having 15 seats to now 19, which doesn't sound like a huge difference but if you add four, those four more tickets to every single run, it really does start to add up.

How did the pizza and cocktails tour come about?

Jonathan Porter: I noticed I had been taking out so many groups on Saturday and we'd get to the first stop and everybody would come to the table and they'd already have a 312 or a glass of wine in their hand. Then we'd get to the second stop and they'd be trying something else. I thought, "Okay, this really makes sense to me. Why don't we just go ahead and plan an evening one that basically pairs up wine and beer and different types of pizza?"

That's pretty brilliant. Especially since you're already driving them.

Jonathan Porter: Yeah, exactly. [Laughs.] The one thing I always think is that we're going to four restaurants, you're getting four drinks, you're getting four or five slices of pizza. But what I didn't take into account was that people -- say they have lunch around 12:30 and they're not eating again until 7:30 at night because we have to sort of wait for that first wave to go through. They would get to the place at 6 and start drinking. By the time we started at 7:30, I'd get them their first drink and slice of pizza and be like, "This guy is already kinda in the bag. We haven't even started yet!" My original thought I was only providing four drinks, I'm not going to get people who were too hammered. Well, that went right out the window. They just like to have a good time and figured they hadn't eaten in seven hours or so and they've been drinking, getting ready for this. But there's been no crazy things on it. It's been a lot of fun.

What do you think entrepreneurs can learn from all that? To where you are today?

Jonathan Porter: I'm the type of guy where I visualize everything and I say, "Okay, this is exactly how it's going to go. We're going to do this and this point and it's going to be great. It's going to be perfect."

Sorry, I didn't mean to laugh. I just know exactly where this is going.

Jonathan Porter: Right, exactly. The reality is it's all about adaptation and being open-minded and completely loose with your plans and being able to go on the fly. I think on that first one I was just like, "Okay, we're gonna proceed to LaSalle, we're going to turn right and I'm going to show them the Batman stuff. And then we'll turn right on Washington…" But it's like, "You know what? The Memorial Day parade is on Saturday because of course Chicago celebrates it on Saturday, not Memorial Day and you can't cross that way." I got really stuck in my ways of how I wanted to run it and not every tour has to be the exact same experience to everyone overtime. It took me a while to really loosen up. That's true for everything in life, I guess.

Any other pointers?

Jonathan Porter: I don't want to just say social media, but with the way everything is going today, if you're not keeping up with everything that's going on out there your competitors are and you're missing something. I keep an eye on sales but I don't watch that stuff too closely. That's all gonna take care of itself. I'm not literally out on the street hawking tickets. It's all about online or over the phone.

Maybe once a week I think, "If I was starting up a pizza tour right now, how would I be able to put Chicago Pizza Tours out of business and what would I do first to make my new one better?" I'm basically asking myself, "How would I kick my own ass?" Everything's done online now, too, is the other thing. So I just spend tons of times combing the Internet to see how I can market myself better, I guess, and where I can catch more eyeballs.

So where do you guys go from here?

Jonathan Porter: We always add more inventory as far as the driving tours. If I look at our June calendar here it's going to pick up a little bit. It looks like we're going to be pretty much running seven days a week here. Basically, the first step is to add more inventory. I need to build up the pizza and cocktails one. That one's a little bit younger, so it doesn't get as much as a draw to it. Maybe we'll have eight one week, six the next and then it could be 15 the week after that. The original one is consistently drawing 12 to 16 people.

But I guess the other piece of advice is to really just become a student of whatever it is you're doing. If you're selling hot dogs, you gotta figure out how the hot dog was invented. Every little thing about it.

David Wolinsky is a freelance writer and a lifelong Chicagoan. In addition to currently serving as an interviewer-writer for Adult Swim, he's also a columnist for EGM. He was the Chicago city editor for The Onion A.V. Club where he provided in-depth daily coverage of this city's bustling arts/entertainment scene for half a decade. When not playing video games for work he's thinking of dashing out to Chicago Diner, Pizano's, or Yummy Yummy. His first career aspirations were to be a game-show host.

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