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The Hustle

Name: Tyler Gillespie (“Florida Man: Poems”)

Posted By Andrea Perez

Students who've attended Tyler Gillespie's classes have highlighted his ever-present sense of humor, while maintaining seriousness when it comes to lessons on storytelling. Clever and ready with an anecdote to stir you, this freelance writer has found his beat. He's been able to manage his time for inspiration and deadlines as a contributing writer for Playboy, and planning classes for the journalism and advanced reading courses he teaches at the University of South Florida St. Petersburg. He's also contributed to publications such as Rolling Stone, VICE, The Nation, GQ, and Buzzfeed. This year, this hustler published "Florida Man: Poem", a collection of stories, sonnets, and lyric poems that explore the idea behind the news headline 'Florida Man', a term used for peculiar-but-true, sometimes hilarious stories about alligators flying off into fast food joints, unbelievable drunken escapades or stolen baby parrots. Check Gillespie's book for insights, and try to contain a laugh or smile. Bet you can't.

Years in Tampa Bay

I was born and raised in Pinellas County. I moved away for about 10 or 11 years after high school. I've been back for two.

Hustle (job)

Freelancer

What do you do?  

I'm currently a contributing writer for Playboy, teach at USF (and SPC in the fall), and work part-time at a community center.

Why do you do it?

I freelance because it allows me freedom to work on creative projects on the side.

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

I started freelancing about eight years ago because, at the time, I wanted to work as a full-time writer/editor at a magazine. I recently signed on as a contributing writer to make things a little more contained.

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

Freelance writers do a lot of legwork: We find stories/sources, pitch to publications, and work to get the story as best we can. Then after publication, we often have to hunt down our payments from publishers. It can be a lot.

What’s the most challenging part of your Hustle?

Keeping track of my schedule. Affording health care.

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

Know your worth. Negotiate. Ask for what you want. Respect people's time. Always hit deadlines.

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