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Entrepreneur creates surprise-and-delight shirt business

Sara O’Brien’s yearn for creativity led to a trendy business making and selling shirts with funky phrases. One mantra: Never quit. ‘If you just keep going,’ she says, ‘the energy eventually shifts.’

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Employee: Sara O’Brien, 38. She’s a multimedia designer at journalism education and strategy center Poynter Institute in St. Petersburg, where she does everything from graphic design to video and photography work.

Side hustle: Making clever, locally themed T-shirts through her company, Wide Sky. She got started in 2014 when she was feeling unfulfilled by her previous job. “I wasn’t really feeling like I was getting that creative space I needed,” she says. “So I would daydream about it a lot on my long commutes from Tampa to St. Pete.”

Bridge the gap: Her first T-shirt featured an image of the Sunshine Skyway with the tagline “It’s my way or the Skyway.” “I felt like no one was offering any silly, funny T-shirts that spoke to our unique culture here,” O’Brien says. “So every day I would try to brainstorm silly things.” Other ideas soon followed, such as her “Choose wisely” tee commenting on the three traffic-clogged bridges local commuters navigate daily. “It all comes from my own experience living here in the Tampa Bay area,” she says.

'It’s definitely scary to think about going solo. But if things continue on this trajectory, it could definitely be a reality' Sara O'Brien, Wide Sky

Slow and steady: Once she built a website and had some shirts to sell, she wanted to get into a retail outlet and found an ideal first location in ZaZoo’d, a St. Pete shop with a similar point of view. “It was one step at a time,” she says. “But once I got in there, it was like a no-brainer that I needed to be doing more retail.”

Perfect her craft: O’Brien started out using several screen printers to make her shirts but then figured she could learn how to do the same thing. So in 2018 she began teaching herself to screen print and now makes all her own shirts in the garage space where she runs Wide Sky. “I was literally starting from zero, and it’s been challenging and fun and frustrating and great all at the same time,” she says.

Customer facing: O’Brien has had a lot of success at festivals and markets, once she found ones with “her people.” She adds: “For me it was trying out a lot of things and trying to find the right mix of variable. But now people are finding me at markets and festivals, and I’m able to engage with my customers better and take pictures with them. It’s started building up this repeat-customer business for me.”

Mark Wemple. Sara O'Brien aims for
Mark Wemple. Sara O'Brien aims for "silly, funny T-shirts that spoke to our unique culture" in Tampa Bay with her side hustle, Wide Sky.

Know what you don’t know: Online sales have been harder to grow, which is why O’Brien hired a small business coach last fall to help her with that area. “I felt like there’s only so much I know in that realm, so I just needed help,” she says. “I needed someone who can work on the back end of this stuff and offer me some knowledge about things that might be my blind spots and show me things I should be doing that I’m not.”

Balance it all: O’Brien tries to carve out three nights a week for Wide Sky work along with weekend days for festivals or markets. “You learn that you have to be patient with yourself,” she says. “But it’s also like hey, it’s my business, so I make the rules. And if I don’t show up and print today, I can I print tomorrow, and nobody’s going to yell at me.”

Growth goals: O’Brien sees the potential for Wide Sky to become more than just a side hustle. “It’s definitely scary to think about going solo,” she says. “But if things continue on this trajectory, it could definitely be a reality. I don’t know that it could happen any time soon, but I believe eventually it could come to that. But I would want to make sure that I was still having fun at it. I’d want it to still be something I’m passionate about.”

Just keep hustling: O’Brien knows growing a side business takes time. “It’s just been about keeping going when things get frustrating or you have days you feel like you want to quit,” she says. “If you just keep going, the energy eventually shifts, and you either meet someone who can help your business, or you have an unexpected awesome month for sales. It’s just being comfortable with all the uncomfortable aspects of not knowing what’s going to happen with the future of your business.”


Click here to read more about regional professionals and their side hustles.


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