City Editor Kristen here. I recently sat down with Zach Riddle, a local artist who’s been traveling across the country on his "Fifty Fiftee $50" tour — a project where he travels to all 50 states, makes 50 T-shirts per state, and doesn’t leave the state until all the shirts are sold.

During his tour, Riddle has sold shirts to celebrities like Jaden Smith, Jaylen Ramsey, Benny Blanco, and Diplo + has documented his travels on TikTok, where he's garnered over 73,000 followers. Keep reading for more on his start in Chattanooga, stories from his travels, and advice to other artists.

Q: Can you tell us a little about yourself and how you started making art?

A: I moved to Chattanooga when I was in fourth grade, so I claim Chattanooga as my hometown. I went to high school here and graduated from UTC in 2020. I actually never planned on making art, I went to school for sports management, but during the COVID-19 Pandemic, I started seeing hydro-dipping videos on TikTok. So, I started hydro-dipping canvas and putting vinyl on the canvas. I used the 4th-floor maker space at the Chattanooga Public Library to cut the vinyl logos for the canvas.

I started with smaller canvases, using a two-gallon bucket, but I eventually bought an above-ground pool so I could do larger canvases. Four months after I started making these pieces, is when I started working with Barstool Sports to commission pieces.

Q: How did working with Barstool Sports come to be?

A: During COVID, Barstool's president, Dave Portnoy, would live stream opening packages on his TikTok and he had positive reactions to opening up art, so I sent him 14 custom pieces of Barstool-related art and his reaction was great. Three months after that, they emailed me to commission work, and one of my pieces is in his personal office in New York City.

Riddle travels the country selling his shirts and teaching people of all ages how to make buttons. | Photo provided by Zach Riddle

Q: Can you talk about the shift in your art from spray painting and hydro-dipping to T-shirts and buttons?

A: I wanted to evolve past that kind of art, and three years ago, I started making buttons because of the Chattanooga Public Library. They have a button press table, and since then, I've hand-pressed 40-50,000 buttons. I didn't realize how much I would utilize buttons, especially with the T-shirt project.

Q: Can you tell us about your T-shirt project?

A: I've always wanted to make apparel, but I didn't want to just put my art on clothes, I wanted to create apparel with meaning. I came up with the idea to travel to all 50 states, make 50 shirts in each state and sell them for $50, and I can't leave the state until I've sold all of the shirts. I started the "Fifty Fiftee $50" tour in February of 2023 with my friend who runs Humanitees in Chattanooga — part of the project is that I use a local printing shop in every state. I'm two years into the project, and I average about 10 states per year and take breaks to come back home between traveling. My plan is to finish North East states starting in May.

Q: All of the shirts say "Invest in urself," why did you choose that phrase?

A: Every shirt has the state outline on the front and "Invest in urself" within each outline, one of the big goals I have with this project is to inspire others to invest in themselves, especially other artists and entrepreneurs. It feels like my motto as a person, because the more you invest in yourself the more you can invest in other people. I want to sell a story, and you happen to get a T-shirt when you invest in the story.

Celebrities like Jaden Smith have supported Riddle's t-shirt project. | Photo provided by Zach Riddle

Q: A lot of interesting people have bought your shirts, can you tell us about those encounters?

A: My first happened in Miami, FL — the second state I traveled to. I saw Jaylen Ramsey, who plays for the Miami Dolphins and is from Tennessee. I approached him and he bought four T-shirts from me.

When I was in Los Angeles, I was walking around, and I saw a group of guys and realized one of them was Jaden Smith. We sat down and talked before he went into the studio, and he got a shirt from me. Another day I saw Benny Blanco walking on the street, and he was on the phone, but I still approached him and said, "Give me one minute to tell you my story," and he said, "You have 30 seconds go," and he got one.

I'll also do button-making pop-ups at spots I visit so people can make buttons for free. When I was in Hawaii, Diplo showed up at one of my pop-ups with the Oahu Run Club. I showed him how to make his own button and he also bought a shirt from me.

Q: What advice would you give to other artists?

A: To invest in yourself and take risks. You have to be your biggest supporter and your biggest critic at the same time. So, do things that have people questioning whether or not you can pull it off, knowing that you have the ability to do so. There are always going to be people who are going to doubt you, but that's okay, it can fuel you and motivate you.

You can follow Riddle on his travels on Instagram + TikTok. Want to get your hands on the next round of T-shirts? Riddle will ship out-of-state shirts to those who'd like to support the project, just keep an eye out on his website.