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From ultra-topical missives like "I liked the Bucs Before Tom Brady" an "We Buc'n Won it All 2021" to evergreens including "It's My Way or the Skyway" and "Sunshine State of Mind," Sara O'Brien's Wide Sky creates the most St. Petersburg/Tampa Bay-centric T-shirts around. Alongside her T's, tank tops and other community-focused accessories, Wide Sky now has a line of masks - de rigeuer in the current climate - with slogans such as "St. Pete is Swell" and "It's Pelican, Not Pelican't." Sara's wares can be ordered from the website, and are also sold at Zazoo'd, the St. Pete Store and the Old Southeast Market.

Years in Tampa Bay

18

Hustle (job)

T-shirt designer and screenprinter.

What do you do?  

I make silly T-shirts that make people laugh.

Why do you do it?

Because it’s a fun and creative outlet. And because I’ve always loved funny shirts!

What was your Catalyst? (How did you get started?)

Daydreaming about making unique T-shirts while driving home over the Howard Frankland Bridge. I was feeling pretty down about my day job and wanted to do something on my own.

What’s a common misconception or unknown aspect of what you do?

Everybody thinks they have a killer T-shirt idea, but when it comes down to it, it’s really hard to come up with a design that sticks and that people actually want to buy and wear.

What’s the most challenging part of your Hustle?

That it’s still a side hustle. So most of my nights and weekends are spent screen printing. I wonder what would happen if I could devote more time to it.

What’s the most valuable piece of business advice/insight that’s helped you?

It’s okay to go at your own pace. My business has been built at a slow and steady pace. Sometimes it felt like I was crawling. But as long as you're still moving forward, still doing, momentum eventually catches up and things start to click in all the right ways.


How long did you dream about your hustle before you did something about it?

A couple of years at least! But right when I felt like I was going to burst, I did something about it. I worked on the first design (still my best seller to this day!) and I joined the entrepreneurial academy at the St. Pete Chamber. These were small steps but huge to me at the time!

More Hustle

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