Ep. 055 – Chris DeLorenzo – Johnny Cupcakes, a 500-Foot Airport Mural, and Learning Everything Once

Creative Slash

In this episode of Creative Slash, hosts Brad Woodard and Dustin Lee interview illustrator Chris DeLorenzo about his professional journey. The

Key takeaways

• Chris DeLorenzo leveraged his mentor Clark Orr's working files to master advanced Adobe Illustrator techniques.
• To break into editorial illustration, Chris proactively created mock-up magazine covers for his portfolio to demonstrate capability to clients.

Main topics

• Career transitions in design
• Johnny Cupcakes brand history

Notable quotes

If I do a t-shirt design bigger on a wall, they'll give me 20 grand for it.

Conclusion

The episode serves as an inspiring guide for creatives on how to use c

Transcript preview

Speaker 1 (0:00) There's only so much that people are willing to pay you for a t-shirt design. Like, you can't be like, it's five, you know, it's 10 grand for a t-shirt. They'd be like, go jump off a cliff. Like, what are you doing? Speaker 3 (0:11) It's outrageous in t-shirts. Speaker 1 (0:13) Yeah, but you know, like, if I do a t-shirt design bigger on a wall, they'll give me 20 grand for it, you know? Speaker 3 (0:22) Welcome to the Creative Slash Podcast, where we explore what happens when creativity collides with everything else. I'm Brad Woodard, and I'm joined here with my good friend and co-host, Dustin Lee. This is your weekly dose of real talk about making it as a creative human. In Speaker 2 (0:36) today's episode, we sat down with an illustrator, former Johnny Cupcakes art director, and the kind of person who sees something interesting and immediately Speaker 3 (0:42) thinks, that seems cool, I could learn how to do that. Which explains the slacklining, archery, motorcycle license, and apparently preparing for the apocalypse. We talk about setting up your studio space so experimenting is easier to start, why sometimes the problem isn't your art but where you're applying it, and developing a recognizable style without feeling trapped by it. Plus, how he and his college roommate designed the easy-on condom that the world didn't know it needed. This is the endlessly curious and wildly talented Chris DeLorenzo. But real quick, before we jump in, if you're enjoying this podcast, you'll love the Off the Record email series. We break down the best habits, tools, and takeaways from each guest, including stuff that never makes it into the episodes. More depth, more insight, all organized to actually help you apply it to your creative work and career. It's free, so sign up today in the show notes. Speaker 3 (1:39) No, the best part is you get that long introduction and then afterwards it's like, okay, now tell us about yourself. Wait, what? That was what your job was. You just told me Speaker 1 (1:47) about myself. Speaker 3 (1:48) Yeah. Speaker 1 (1:49) I love your face, Brad. You have really nice lighting back there. Well, Speaker 3 (1:54) thank you. Yeah, Speaker 2 (1:55) I worked real hard at it. Just trying to one-up Dustin is my only goal. I felt so good that you had a background that was similar to mine, Chris. Just Speaker 1 (2:03) like, this is a room. A creative Speaker 2 (2:06) room. Speaker 1 (2:06) Yeah, Brad's about... Brad's about to teach me like Adobe tutorials or something with his setup. Speaker 3 (2:14) Stop Speaker 1 (2:15) doing this trick in Illustrator. Speaker 2 (2:17) Chris works in a regular office just like everyone else. Only difference is when he's in his office, he does New Yorker covers and stuff like that. So, you know. Yeah. Definitely Speaker 3 (2:27) cooler stuff than this. Speaker 2 (2:28) But I was, so you had done Retro Supply's original, well, we still have your logo. We had like some minor things where we have things added and stuff like that, but it's still the same because it's just fantastic. But I remember when you were doing that, you like, I think I was looking at your Instagram or something or somewhere I was looking at something you're doing. You were talking about slacklining. And then I saw a video of you had posted yourself slacklining. And as you were mentioning hitting 40, I was like, I know right around 40, I started to feel like, especially once I had kids and you have a child, I was like. Slack lining becomes the type of thing that Chris might not be drawing for six months if he doesn't slack line perfectly. Yeah, Speaker 1 (3:07) I know. And that's one of those things that I'm like, I just find something, I go, I want to do that, and I'll just try to learn it. And I think I saw someone slack line. This was like years ago. It's currently just in my barn. I ran out of trees to connect it to in my backyard. Speaker 1 (3:27) and it was just like, I want to know how to do that. And so I set up in my backyard when I was living where I was living at the time and just like taught myself one summer. Speaker 3 (3:35) That's really good core exercise. Speaker 1 (3:39) But then it became like lame. And so now I'm like, I don't slackline. Speaker 3 (3:43) Okay. Funny thing about that is people still do slackline. And the reason I can say that is because I was in Utah for like a vendor market. Uh, and I went with my, my son and we were, we were driving weird. Driving into this park to go with the market, it was an outdoor market, they have these trees and there's a sign on them that said, no slacklining between trees. And I was like, in 2026, that's a notice that has to be put up. Wow. Speaker 1 (4:08) That's like a park being like, no devil sticks. Yeah, exactly. You're like, I don't know how Speaker 2 (4:14) people are doing that. Do people still do that? Speaker 1 (4:18) No playing pogs here. I went to Mexico on my honeymoon and we went to this awesome water park called Shell Howl. And it was like where the locals go. And it was a little bit sea world, a little bit just here's a basin of water. And it's just, you get a snorkel and you're like, yeah, just go swimming. And it's one of the coolest like natural. Speaker 1 (4:45) plus water park experiences. It was very cool. And there was like a lazy river part and you go down and towards the end, there was like a slackline thing. You could like, you know, swim out and climb up and it's all just like, it's just like a big open park, water, forest. You can just climb around and there's a slackline thing over water and a bunch of people were trying it and I was like, babe, I gotta do this. I gotta show these like 12-year-old kids like, What's up? Speaker 3 (5:15) Oh, yeah. How'd you do? I Speaker 1 (5:18) fell off about halfway. I was like, I'm out of practice, guys. I used to be able to do this. Speaker 3 (5:26) I'm out of my element here. Speaker 1 (5:27) Yeah. It was a lot of fun, though. Speaker 2 (5:30) I mean, it looks like the equivalent of that thing at the fair, you know, when you're supposed to climb to the top and hit the bell to win a prize, but everyone rolls off Speaker 3 (5:37) that ladder. Oh, yeah. So I feel like even making it Speaker 2 (5:40) one Speaker 3 (5:40) step is Speaker 2 (5:41) an incredible athletic achievement. Speaker 3 (5:45) Especially at your advanced age, Chris. Speaker 1 (5:47) I know. Well, I haven't tried it, you know, after turning 40, but my knees are now, you know, making sounds. So that's always good. Yeah, it was like, and then like I woke up and I just looked at the left side of my head and I was like, wait, I thought there was gray. I noticed some gray on the right, but then like the left side, I was like, now there's just gray over there. Speaker 3 (6:07) Yeah, just ever. Speaker 1 (6:08) Instantaneously. Yeah. Speaker 2 (6:10) It's taking over your entire head. Speaker 1 (6:13) Yeah. Speaker 2 (6:14) I feel like when we had talked, which, by the way, I have to say, there's a story I tell about when you did my logo that I thought was just like one of the best examples of great design. Brad, try to remind me if I forget to go back to this. But I remember when you did that for me, I had seen some of your work from Johnny Cupcakes. I just loved it. You know, you were like my ultimate, like you were my kind of stretch goal. I was like, I'll ask Chris, Chris, if he'll do this. I don't think he'll do this, but maybe he will. Um, but you were sort of at this point where you weren't doing Johnny cupcakes anymore. Speaker 1 (6:49) Yeah. And Speaker 2 (6:50) you were just starting to transition. I, to me, it felt like into like a new style. It was much more minimalist, maybe much more just purely line based. Speaker 1 (7:02) Yeah. Speaker 2 (7:03) Yeah, like, can you like talk about like, how did that come about? Like, why did you go that direction? Where did it take you? Speaker 1 (7:09) Yeah. And it's funny that logo, I was still sort of in my designer. Speaker 1 (7:20) Like not phase, but I still had a lot of those muscles that I was working. I was doing t-shirts and logos, but also doing, you know, like New York Times little editorials and some small campaigns. And that's what it came about. You know, I was doing Johnny Cupcakes and I was kind of not emulating, but I was under the tutelage of like Clark Orr, who set the style. Of Johnny Cupcakes, legendary designer and amazing guy and the nicest person you'll ever meet. That's true. He Speaker 2 (7:57) kind Speaker 1 (7:57) of gave me a lot of experience. And I looked to him for like, how do I do this? Because some of the work I do now is almost the style that I submitted to Johnny when I wanted to get the job. It was a very simple line work, kind of like tongue in cheek. simple humor. And then seeing Clark's advanced, you know, technique, I quickly had to be like, okay, like I can, you know, and like I said, I could pick, I can pick things up quickly. And so I looked at Clark and he gave me all his files, which is, and, you know, I feel like that's the best thing to, if you want to learn how to design, just, I don't know if anyone will give them to you, but just ask your designer, can I have all your working files? And just like go through them. Start sweating Speaker 3 (8:45) immediately. Yeah. Clean them up, name them. Speaker 1 (8:49) Yeah. And it was just like, oh, like, you know, and he had this whole process like on his working files. It was like, here's how I came to that final design. And he was like, just like a big dump. He didn't, you know, select or anything or try to give me just the final design. So I had the, so I saw all of his working Illustrator files and how much he could do in Illustrator and like what looked like the final result. And I was like, oh, it looks so cool. I do that. And it's like. Oh, like he wasn't even, sorry to call Clark out on this. It's like he wasn't even like thinning lines like how you can in Illustrator or like use different brushes. He was just taking a line and then taking white and making a white shape and like trimming the line with the white shape, Speaker 3 (9:29) which Speaker 1 (9:30) is like probably a long way to go about doing something like that. Oh, Speaker 3 (9:35) yeah. Speaker 1 (9:37) Oh, yeah. Did he have Speaker 3 (9:38) a reason for it or did he just do it because that was just like his technique at the time and he just... Speaker 1 (9:42) Yeah, I think he's just like, oh, I learned this and I'm sure there's a hundred ways on Photoshop now that could sort of help me in my way. But I'm like, I'm just going to do it the way I know. And, you know, sometimes the way you know is faster. But I always thought that that was kind of funny. And so I did that with Johnny Cupcakes and it sort of defined a new style. applied that to logos and but I still have my drawings that I was doing and every now and then we would sneak one into Johnny Cupcakes that was a bit more Chris centric and less like Johnny Cupcakes brand centric and then Tumblr came along or I met my friend Pascal Da Silva who was friends with like all the Tumblr guys that started Tumblr Dave I think David Karp and like Jacob Bajani and Chris Kalani and Derek Salami. So Speaker 3 (10:38) many Salamis. Speaker 1 (10:41) And he was like, oh, my buddy has this cool website. He showed me Tumblr and I just started posting drawings to Tumblr. And I had more followers on Tumblr than I do now on Instagram. I think I still do, but I never check it. And then I was like, oh, this... this is getting some traction. And I was just posting a lot of stuff like that. You know, just little like one-off drawings that I didn't have a home for at Johnny Cupcakes. And then I started to get like work through that. And then it just sort of snowballed from there. But yeah, like it's like if someone asked me to do a logo, I'm like, yeah, I can do that. But I'm like, I don't really do it anymore. But, you know, I still like to do that as well. I recently joined... I'm one of the inaugural members of my town's public art committee. So it's pretty cool. Yeah. So now I'm like, oh, I'm an adult. I have a town.us email address. It's all very official. We meet at the town offices. I have a little name plaque. And we were meeting at this big U table for two meetings. And I mentioned to one of the town employees, I was like, I don't know if this is like the best, this might work for another, like a school committee, but most creative meetings I have, we're just like sitting around, it was like a whiteboard and people just like sort of talk. I think we need a less formal setting for people to sort of feel a bit more comfortable. And then we moved to a different room. So I was like, all right, he took my advice. Speaker 2 (12:15) Do you still live in Boston? It kind of felt like we were at Speaker 1 (12:17) the UN. Yeah, yeah. The Speaker 2 (12:19) UN. It kind of looks like Boston in the office you're in. I don't know how to say it. The doors are almost taller and thinner. It sounds really funny, but I have family in there, and I feel like there's a certain way things are built that feels sort of like the Northeast. Interesting. Speaker 1 (12:35) Yeah, it definitely does Speaker 2 (12:36) feel like you're going up in the world when you start to live in the Boston area, and you're on a committee for a town. It feels like you're in a movie. Speaker 1 (12:45) I don't know what movie. Speaker 1 (12:50) So we started the committee there and I was like, you have to sort of like file motions. Like I want to like file a motion for a spontaneous idea. What about if we did, you know? And someone's like, I second that. But I was like... I nominate myself, I, Chris DiLorenzo, Esquire the third, to do a really cool logo for this committee. And people were like, yeah. Speaker 3 (13:19) The crowd is for it. Speaker 1 (13:21) Yeah. And I think we had to get like, someone had to be like, I second for Chris doing the logo. That's hilarious. Yeah. So then I was like, then I kind of got into it. And I was like, oh, I haven't done a logo in a while. And I probably spent more time on it than I should have. just because I was like, you know, I got to exhaust some options. Ooh, I want to explore some more typography I haven't done in a while. So I was doing like, you know, seals and then I, you know, a couple almost like retro bold designs. And I tried some funky ones and some character based ones. And I was just like, I'm just going to fuck around. Yeah. So I kind of screwed around with some seal designs and some old school, like, not anagrams, acronyms. Oh, yeah. Some character designs and some more modern, clean ones. I was just sort of running the gamut just because I was having fun with it and definitely spent more time on it than I should have. Speaker 3 (14:17) That's amazing. My wife and I joined the Chamber of Commerce and it does not feel as cool as that, but I can definitely get a little, I can relate a little bit to those meetings now and being like, I'm an important business owner here in town and I get to help make decisions. Speaker 1 (14:31) Yeah, that sounds a bit more political. Yeah. You know, which I'm sure probably you can get a bit more, not backlash, but you probably hit some road bumps here and there. Speaker 3 (14:46) Oh, yeah. Trying to pass certain things Speaker 1 (14:48) and get your voice heard. Speaker 3 (14:50) Luckily, when it comes to art, there's like two older women that are in charge. And, dude, they're the best. Like, we got, we live in such a tiny little town. We got these two, like, hippie artist ladies that run it. And they just are, like, all for all the ideas. And so I'm like, I got to be friends with you guys. Speaker 1 (15:08) Imagine, like, 11. a whole committee of like 11 people that are just like, yeah, let's do that. Yeah. But it's kind of cool because I've been, I've been on, you know, the being hired side for so long and I'm friends with so many artists. And now I get to kind of approach them and like people whose work I admire and be like, hey, we're opening up a little park over here in our town. We got like 25 grand. Can you do a cool sculpture or something? And kind of I can help facilitate that and also learn a bit more about some processes and stuff, which is pretty cool. Can Speaker 2 (15:41) you talk more about that? Because I started originally as a designer and then pretty early on started hiring people to do various different projects. And what has it been like? What is your view from looking in instead of looking out on what it's like to hire people as opposed to be the person being hired? Speaker 1 (15:59) It's cool because I don't know if most people see this way, but sometimes you see you follow an artist's career and you feel like they are in their own silo or something or not quite your contemporaries, but you're almost like, ooh, there's a slight competition always with artists. And they go, someone does that and inspires me to, I'm going to do something better or now I want to try a sculpture thing. Speaker 1 (16:27) and just like elevate your art and Speaker 1 (16:32) being on the town side now, I get to now see it as a community rather than like these people that maybe were fighting for jobs. It was like, oh, like how'd they get that Nike gig? Like I should have, I've been doing stuff like that. You know, and now it's like, oh, like I can now see them as just a community where it's like, hey, great stuff. Do you want to do stuff here? And then it opens up a conversation and just breaks down a wall that I think sometimes, you know, I can put up or. I don't want to speak for others, but I feel like there's a separation. And when it's now you're just like hiring the person, you kind of feel like you're not an artist anymore, but like an admirer, which you are. But, you know, you don't come at it from like the artist's angle. Speaker 3 (17:16) Yeah. Did you do that at Johnny Cupcakes at all? Did you get to work with other artists outside of just yourself? Because I know you were art director, weren't you? Speaker 1 (17:25) Yeah. Speaker 1 (17:27) It's tough to make a title there. It's kind of like senior art director, associate career director, lead designer. So whatever was made, I had to think about and create and plan for the next one as well. So it was kind of everything. Even when it came to packaging or when it came to events and store design and the clothing and new materials and patterns, it was all... It all kind of came down to me with, you know, we would have some creative meetings and be like, what about like polka dots? Yeah. And then be like, what do you got, Chris? I'll come back at the end of the week with a bunch of polka dot stuff, you know. Can you say a little? Speaker 2 (18:14) Sorry to cut you off there. Can you say a little bit more about that? Because like just behind the scenes of what it's like, because I know, you know, I. I've been opening Johnny Cupcakes emails every time I get one. I always look to see what's inside of it. I visit the shop regularly to see what's going on. And I was always amazed by the output. I was like, how? Johnny Cupcakes doesn't feel like a huge company. I don't picture there being a bullpen of artists. I picture it being a small amount, yet the output is profound. Paint a picture for me. How many artists are there? Are you with like... 10 other artists and you're just all working 40 hours a week? Is it just you and then some contractors? Speaker 1 (18:53) Yeah, it's me in my 20s. That's a great answer. Yeah, that was how things could get, you know, so much output at that time. Like there were times where I was, you know, I didn't have a girlfriend. I wanted to draw and... design and get better. So if we had an idea and I was like cranking away on it, like no one's calling me home. I don't have like kids I got to go. And so it's just like, I'm just going to sit here until nine o'clock until I finish this. And like, it brought me joy. And so we could, we could do a lot because of that. We had a couple, we had like one designer, but he left like a year in. So it was mostly me for like five years. And then we brought in a second designer towards, towards the end. who I believe still does some work for Johnny. And it was tough to find someone. There was a process where I was like, okay, I need some help. And so made like a broad call for artists with Johnny's, you know, reach and stuff. And we got a lot. And with the style and stuff, there was a certain kind of way, like who I could see potential in, in a way. You know, there were great artists, but it's like not going to be great for t-shirts or like. do they have ideas versus like, is it just like cool? And so that was a process. And we found this guy, Corey Reifinger, who was, I believe like living in Pennsylvania at the time. And he moved up to Massachusetts to join us. And so I kind of like mentored him in that way. Hopefully he feels the same way I feel about Clark. But who knows? He might be like, yeah, Chris was always just like, yeah, man, it looks like shit. Keep going. Speaker 3 (20:35) I'm going to go slackline. Speaker 1 (20:37) Yeah, I got to go slackline right now. I got to go, you know, skateboard around the warehouse for a second. But we would bring in like, do you know the artist or designer Timba Smits? Yeah. Speaker 2 (20:50) I love him. Love him. Yeah, Speaker 1 (20:52) he's awesome. And we got to meet him. When we opened up the London shop, I think we had become internet friends and met Timba. And he's an awesome guy. And we used him a couple times. And it was cool to bring him my designs. And I was like, Timba, take this design of mine and give it that Timba treatment where it looks like a 1950s newspaper, which he's so good at. Yes. Oh, yeah. I actually Speaker 3 (21:22) have Speaker 1 (21:22) a couple of those here. We did this Halloween project. This is one of Timba's. Oh, it's so Speaker 3 (21:31) good. We always did Speaker 1 (21:32) these thematic shirts every Halloween. And this year we did 80s, or not 80s horror, but just horror movies. And we packaged them in these old VHS boxes. I mean, we crammed a shirt in there. I was Speaker 2 (21:48) going to say, Speaker 1 (21:49) how Speaker 2 (21:49) did that fit? That would have to be such a thin shirt. We couldn't get Speaker 1 (21:52) the Titanic VHS box, so we had to go for the singles. We didn't get that double tape. But yeah, Timba, he did this one, and I did. This one, Rise of the Two-Headed Zombie Chefs. And Timba gave it his retro treatment. But we also shot trailers for each t-shirt. We got one of my friend Lucas' best friends from college who's a filmmaker. And he was like, yeah, I'll come. And he got all these actors and it was like his project too. So each one, like this one has like a... Retro 80s. This one was like a black and white noir, like silent movie. It was really cool. And Clark did this one, the classic one, with also a Misfits tribute. Oh, that's amazing. The band Misfit, of course. And then I did this one, which is like a 50s sci-fi, Robot Ovens from Mars. Oh, Speaker 2 (22:56) that's so good, Speaker 3 (22:57) man. Speaker 2 (22:58) I love how the ray is the actual oven opening. Speaker 3 (23:02) Yeah, Speaker 2 (23:03) that's brilliant. For projects Speaker 3 (23:04) like those, did you see any added benefit for doing those things outside of just like, you know, for doing all the extras, right? Doing the trailer and things like that. Did that help monetarily for the sales or was it just like, let's Speaker 1 (23:20) just do Speaker 3 (23:20) the idea and let's just go on to. Speaker 1 (23:22) Because these were limited. These were to the sale. One of like 200. So there were 200 of these. So no matter what we did, and this was a six year and every year is always sold out. So it was like, all right, you know, kind of, we could have made more money if we made more product. Speaker 3 (23:41) Sure. But then it's demand. Yeah. Yeah. And that was Speaker 1 (23:45) a big thing with a Johnny Cup case was always keeping it limited. And then it was the kind of like quarterly crisis meeting of like, we got to make payroll. And then they would be like, Chris, what do you got? And I'd be like, oh, here's something. And then it would, you know, we would be like, here's a special flash drop for this new shirt. And we, you know, or we would take pre-orders or something. But that was the thing is we tried to push, like we need to expand if we want to make more money or like, but the whole thing was to keep it limited. And it's kind of tough when you're like, hey, I want to not rent an apartment forever. Can we print more t-shirts for this limited release that we always sell out of and we know people wait a year to get? But that would ruin the whole specialty of it. So we had to strategize and create different tiers of product that we could... Because everything before was just a one-time run. Oh, did you get the logo shirt on Royal Blue? They don't print that anymore. They did that once in 2010. They haven't made it since, but it's like, why are we shooting ourselves in foot? Let's just have... So we tiered the products as classics, originals, specials, and maybe one more. So this would have been a special. And the originals were just our monthly drop of new designs. And the classics would be evergreen shirts that were made earlier on or ones that got a huge acceptance of. Speaker 1 (25:24) like I did this like Banksy one where it's like, you know, he's throwing the flowers, but he's throwing a cupcake. And then that one became a classic because it was just like, yeah, this is just a moneymaker. It just keeps selling. So let's just keep printing it. And like knowing that, I think once we tiered it that way, people knew, okay, these are the originals. These are the collector ones. And the classics are just for like people that come off the street and want a nice shirt. So the market kind of self Speaker 3 (25:52) -selects. Yeah, Speaker 1 (25:54) which definitely helped us a lot. And so that was a big change, a big upheaval of the company in that way. It totally changed how we positioned ourselves. We lost some people because we're like, I don't like it anymore because they reprint shirts. It's selling Speaker 3 (26:13) out. Okay. Speaker 1 (26:15) Then buy the ones Speaker 3 (26:16) that we don't. Speaker 1 (26:17) Exactly. Well, we still have some stuff for you, sir, ma'am, madam. Speaker 2 (26:23) From an artist perspective or creative director, it sounds like you could change your title whenever you felt like it was shifting in the business. But as a creative in the business, and you've worked on so many different, you've done such amazing work for so many different businesses. There's lots of people that make t-shirts. Johnny Cupcakes is like very innovative in the store displays and the packaging. I feel like there are other people that have tried to do things like that. What do you think was the engine that drove, I guess, the reach for to grow the business? Speaker 1 (27:00) I mean, a lot of it falls down to Johnny himself and when he started the business and how novel it was at the time. And I think the community that he sort of fostered because of it. And he never really saw customers as customers. They were families and friends and people that he met when he did pop-up shops and stuff. And these repeat customers, I got to know a lot of fans of the brands that just became people in my life. And I think that community... kind of helped them stand out. And it was original. It was like silly. It had a gimmick versus like, you know, like Supreme, which is like based on just like, we're cool. And we're... That's true. And like escape. Yeah. And it's sort of like, we just, you know, we were lumped into like that streetwear category in some ways, but we kind of weren't. So it was tough to sort of be like, well, we're not streetwear, but