This transcript was generated from the episode audio and may contain minor errors.
Thanks so much for tuning in today. My name is Chris Guillebeau, your host of Side Hustle School. Welcome to the program. Welcome as well to our segment known as Throwback Thursday. We also call it "Where Are They Now?" because what we do is we get an update. We take an in-depth look at someone
whose story has evolved since we first featured them. You get to hear directly from that side hustler. Now, last week we heard from a vintage store owner in Birmingham, England. Before that, we had the founder of an e-commerce brand focusing on outdoor hockey as well as a North Carolina orthodontist who invented a better way to treat impacted teeth. So a whole range of topics there, and I'll throw one more at you here. Today in our latest feature, you're going to hear from Steve
Dolinski. He is the founder of Pizza City USA. Pizza City USA based in Chicago offers walking tours and a lot more, actually. He's going to tell you more about it from, as I said, their home base in Chicago. And since we last featured him, Pizza City USA has survived a pandemic, so that was good.
They're also now planning a global pizza festival this summer. So let's hear more about all those things from Steve. Hi, I'm Steve Dolinski. I live in Chicago. I'm the founder of Pizza City USA Tours. Pizza is officially my side hustle. I was in episode 809 back in the day. So my side
hustle was born in about 2017-2018 when I decided as a food reporter here in Chicago. I was working at ABC 7 News at the time. I covered everything under the sun that's edible, but I'd only done pizza kind of in fits and starts. And what set me off was reading a listicle online of the seven hottest pizza places in Chicago, which I really took issue with. And I thought, has anybody actually ever done a deep dive on pizza here? Lo and behold, it had not been done. And so I just set
about the next couple of months doing three and four places a day, really getting to the bottom of it and realizing that there's a lot more than deep dish and stuffed pizza here and tavern style. There's a lot more than just sort of the cliches that we hear about all the time. And there's really a lot more a lot more styles like Sicilian, Detroit, Roman, Neapolitan, artisan, tavern, thin, I mean, there's so many styles of pizza here. So it really is a Pizza City. So we I launched a book called Pizza City USA as a side hustle. Then I launched a pizza tour business called Pizza City
USA tours, just finished our fourth season, launched a pizza podcast called Pizza City, and most recently started embarking on creating the first ever Chicago Pizza Festival. This is still my side hustle because I left ABC seven in early 21. And I had the summer off. And then I got hired by NBC five. So now I'm at Channel five and doing the same kind of food reports I was doing before every Thursday night. That's kind of still my main gig. And I would say that pizza has taken up a bit more
than just a side hustle. But I definitely still think of it as as my thing on the side. And just like I did in the past, I was wondering had anybody done a deep dive on Chicago Pizza and nobody had? Well, surprisingly, nobody had ever done a really a Chicago Pizza Festival. And so I felt like because of my connections now with Pizza Master ovens, they're electric, they can be rolled and transported, we're going to have 10 Pizza Master ovens out in the parking lot in the West Loop. This is going to
be July 23 and 24. And we're going to have 20 pizza makers on Saturday, another 20 pizza makers on Sunday, each oven is a different style with two different pizza makers dedicated to it. And so we bought we created the LLC, we bought the URL, we've set up a bank account. I mean, we have a business now that is Chicago Pizza Festival. And we hope that we can get sponsors, that's going to be the big challenge. My biggest challenge right now is twofold. It's finding sponsors for the event. And I
think we've got a good track record. And you know, we'll attract people because we're putting that great event on. And it is all about the pizza makers and celebrating Chicago Pizza. But the other factor and the other challenge is continuing to sell pizza tours because we start up in May, that's here before you know it. We just want to get people we want to get about 70 75% occupancy for our tours. I think the best advice would be for someone who wants to do what I'm doing or
follow in the in my footsteps would be to really, first of all, do the research and figure out where the gaps are. I saw that there was only one pizza tour in Chicago, all of Chicago and I thought that was an opportunity. So I launched my my tour business. I saw there were no pizza festivals being done here properly. That's an opportunity. And since I have the expertise with pizza and
those people in that world, I mean, I'm able to tap into that network as well. So I think a combination of having the network and a reputation as a good guy who's not going to take, you know, things from you. Oh, I want to promote the P three is I want to make sure they get paid for their time. But then also shining a light on something that just, for whatever reason, didn't have a light shown on it before. So I think looking for the gaps, doing the homework and being respected will will help people sort of, I guess, attain their some of their goals.
Not all of them, but it's it's good. It's good to put you on your way there. Awesome. Thanks so much, Steve. Really appreciate those updates. One thing we didn't get to in
Steve's updates, he shared with us that during the pandemic, especially during, you know, those first few months when everything was shut down, he actually did a bunch of virtual events. And you might think, well, how do you do virtual events with pizza? Like you're normally doing like walking tours, right? Well, what he did basically once a week, he would have an event that was a pizza party for a law firm, a consulting firm, something like that, you know, lots of different groups that could be anywhere in the country. And, you know, a dozen to 50 people would be on zoom. And he would organize deep dish pizzas to be sent out from Chicago,
shipped to everybody, you know, frozen, and then they would heat up the pizzas like 45 minutes before the event. And he would take them all through a PowerPoint, talk about the history of pizza in Chicago. And then they would, of course, you know, taste the pizza. So, you know, you can do virtual events for anything, right? We've had virtual meditation, we've had virtual boxing lessons. Now we can add virtual pizza parties to that list.
Again, thanks, Steve. Listeners, check out his website, pizza city usa.com. Super cool. I got really hungry while I was looking at the website, working on this episode. He's also got a book, a podcast, those walking tours you can take when visiting Chicago. And of course, that upcoming
pizza festival. I would love to go to that. Let me know what you think and who you'd like to see featured from our archives of more than a thousand stories. We are going strong working towards episode 2000 here in fact. So thank you for your support. If you have a question,
if you have an update for us about your hustle, sidehustleschool.com/questions. That's all for today. But of course you can subscribe or follow wherever you get your podcasts. New episode coming up tomorrow. My name is Chris Guillebeau. This is Side Hustle School.
From the Onward Project.
