8 min 43 sec

Teen Funds Dance Intensives Through Online Store

A Portland teenager sells t-shirts to fund his interest in dance, bringing in $8,000/year while attending middle school.
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What It's About

A teenager channels artistic talent into a successful t-shirt hustle.

Business Model
Arts & Crafts
Skills Required
Design & Marketing
Profit Potential

Words of Wisdom

One of the ways Hobbs was able to be so successful was by forming strong connections with his community and by being vocal about his goals. A lot of his start-up costs were low, simply because people he knew gifted him materials. By telling others about your goals, it allows people to help to make them a reality.

Fun Fact

The name CityTroll actually came from a nickname that Hobbs’s uncle gave his mom. AJ was a city girl through and through, so her brother adopted the nickname city troll. When Hobbs found out about this, he thought it was hilarious. From there, they made it the name of the company!

Notes from Chris

Episode 1084
It was 2014, and seven-year-old Hobbs Waters just couldn’t find a hobby that fit quite right. He’d been trying to play basketball, but it wasn’t for him. His mom, AJ, suggested football, or maybe soccer—but Hobbs rejected both. At one point, he started baseball, but that wasn’t his jam.

He loved spending his free time drawing and painting, but AJ wanted him to also find something that would connect him with other kids. They were living in New Orleans at the time, and AJ mostly had college friends who didn’t have kids. They were missing a larger community and sense of belonging.

Later that year, AJ happened to see that there was a ballet class taking place close to their home. She asked Hobbs if he was interested, and he agreed to try it out. That class made quite the impression on Hobbs. He was “lit up” for several days afterwards. Soon, he was taking two ballet classes a week. Hobbs had found his people.

In 2016, the family moved to Portland, Oregon. Shortly after, Hobbs had the opportunity to attend a 7-week long dance intensive over the summer. He loved the in-depth training, and immediately started looking for more opportunities to improve his new skills.

The only problem was that dance intensives are expensive. AJ knew that it wouldn’t be realistic for her to continue to pay for them and his regular dance classes. However, around the same time, Autumn, a friend of the family’s, noticed Hobbs’ artwork. Autumn was a talented ceramicist, and thought Hobbs could be successful selling his work.

Intrigued, it didn’t take long for both Hobbs and AJ to jump onboard with the idea. To start, they decided Hobbs would sell his artwork printed on a few items such as t-shirts, mugs, and tote bags. They created an online store, which they called City Troll, and started working on some prototypes. Hobbs attended a screen printing class, and got help from a graphic designer to soup up the new website.

His first customers came from AJ’s friend group, which they nicknamed “Auntie Nation.” The women came together to both buy his products but also to spread the word. At the same time, this wasn’t just a friends-and-family effort. Hobbs started hustling! He talked to people in the community and posted on social media. Slowly, the sphere of customers buying his work began to grow.

To increase his entrepreneurial knowledge, Hobbs read Start With Why by Simon Sinek and went to several workshops, talks and seminars. This has allowed him to network and build a community of support. After each workshop he attended, he increased the number of people around him who were providing him with advice, pointers, and help.

Over the last three years, the City Troll hustle has grown into a real business. The t-shirts on his website cost around $35, while hoodies run about $55. Many of his designs focus on black empowerment, and include phrases like “black artists matter.” He also sells shirts with drawings of animals on them, including elephants, flamingos, and rams.

City Troll now brings in about $8,000/year, which is going a long way to helping him fund his dance career.

Thanks to the profits from City Troll, Hobbs is dancing all the time. He’s performing as the lead role in Nightmare Before Christmas at the World Trade Center.

And, that’s not all! Hobbs is really trying to double down on his business for next year. He is starting to get wholesale orders, and has plans to keep growing City Troll.


  • City Troll: Learn more about Hobbs and checkout his online store at the City Troll website.
  • Start With Why by Simon Sinek: One of the resources Hobbs used to level up his entreprenueral knowledge.

Inspiration is good; inspiration combined with action is better. Now get back to work!

Yours in the revolution,


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Quote of the Day
"People can be dismissive of kids so be ready and be calm. Also have fun with it, keep expectations low. It will be an adventure, treat it accordingly."
—AJ (Hobb's Mom) #SideHustleSchool

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Chris Guillebeau