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By Kara Pound

It’s been nearly two decades since artist Jason Woodside lived in St. Augustine, but that doesn’t mean that the Old City is far from his mind. The New York-based painter, whose abstract work is comprised of vibrant colors and geometric shapes, is as much a native Floridian as he is a globetrotter and renowned artist. His work has graced exterior walls all over the world, from Los Angeles to Paris. OCL caught up with Woodside as he was here in town visiting his older brother David, co-owner of Moonshine Wood & Steel, and his father, John (his mom, Lynn, currently lives in Panama City). Over a cup of coffee beachside, we got to know more about the man who grew up in St. Augustine (he attended R.B. Hunt Elementary, Hartley Elementary, Gamble Rogers Middle School and St. Augustine High School), as well as his work with major brands such as Google, Fabergé, and Adidas. Here’s part of that conversation.

What was life like growing up in St. Augustine?

I was into surfing and skateboarding – self-sufficient sports. My brother is an amazing baseball player, and my dad was really into coaching and that sort of thing. I played a little bit of baseball but was more into self-sustainable sports, things I could do to have fun by myself and be resourceful. I think that’s just a personality trait. I thrive being by myself in work and other things. When there weren’t any waves, or it was too hot to skateboard, I’d sit inside and paint or build something – anything I could do with my hands.


You moved to New York City to attend the School of Visual Arts. What did you end up getting a degree in?

I was really into making movies and wanted to be a filmmaker, but ended up getting jealous of the kids painting and doing graphics. I got sick of watching movies every day in dark rooms and stuff and decided to go into Fine Arts. I actually never graduated. I dropped out because I didn’t want to do film anymore and, to tell you the truth, it’s really expensive at that school. I ended up moving to Los Angeles and started working for a skateboard company, then a fashion company.

Was that a difficult decision to make?

It was just figuring out exactly what I didn’t want in life and then being strong enough to be able to let go of the pride thing. I had to say to myself, “You know what? I don’t need school. I think it’s for some people, but it’s not for me. It’s not really my direction. I’m just going to paint pictures.”


How did your parents react to your leaving school?

They were terrified. I think my parents were terrified until last summer. It took their seeing images of my work through a third party. It helped reassure them that I was getting to a certain scale that was much bigger than what they imagined. They’ve been so supportive ever since, and they get it. Even from the beginning they would say, “Do what you want. Just be happy.” But there was definitely a point where they realized my hobby could make me a good living. It’s hard to get support from your family and friends when you’re doing something that’s not super normal.

Your aesthetic is very recognizable. How old were you when you found your artistic voice?

That’s the hardest thing. I think that’s the secret to being an artist. You want to do a million different things. You want to paint pictures of people. You want to paint pictures of your dog. But, if you just hone in and focus on one thing . . . I used to have an intern, and he asked me, “How do you do this?” I said, “You just got to do what you love to do. Also, find a niche – something specific – and go after it and perfect it. You can go paint pictures of watermelons and be the ‘watermelon guy.’ You could become the most famous watermelon painter. Paint half watermelons, slices of watermelons, watermelons with no seeds. You can do a bunch of different things. Just stay consistent, and hone in on perfecting it.” I think with my work, on a consistent level, I could see the growth. I really love color and shapes and applying them to obscure objects. I could have so much fun with this. I think doing it for yourself and being happy with the end product is the best.

What year did this start happening for you?

Probably 2006 to 2010 is when I really started honing in [on my aesthetic].


A few years ago, PepsiCo asked you to create art for their bottled water brand, LIFEWTR. How did that come about?

They wrote me a message saying, “We like this piece of art. We’re doing a water company. We’re Pepsi.” To be honest, I was really scared. I didn’t think I wanted to work with Pepsi, but they were able to match my budget with a charity, which is awesome. I had a mentorship where I’d go and teach kids how to paint. That lasted for about a year and a half, and it ended up being a great partnership.

Many people in St. Augustine might not know this, but your work is seen by thousands of people each day here at the Davis Shores Car Wash just over the Bridge of Lions.

I painted that in either 2013 or 2014. My friend, David Kfoury, bought the car wash and said, “Man, let’s work together. Do you want to paint the front of that?” I don’t think the city cared too much for it, to be honest, when it first happened. There was a bit of friction, but I think that it’s important to push a little bit in the sense that so many kids here are hungry for creativity and a new wind of change. We painted a building in bright colors, and it’s super fun. We didn’t do anything negative. Just because it doesn’t fit your color palette or something, just be open to it.


You also own a coffee shop in New York called Happy Bones. What made you want to be a small business owner?

I wanted to have the [financial] security to be inspired [in my art]. There was a time when I didn’t have a ton of jobs and I just needed to make money. I did a big job for Adidas and took the money and invested it in a coffee shop. This was in 2010. The kids who are working there are so loyal, amazing, lovely, and friendly. It’s everything you’d want from the place you get your coffee in the morning. It’s in Little Italy, and it’s so cool because there are a lot of creatives in the area from design firms to filmmakers to proper fine artists. It’s so diverse and a great hub for creative people to come through and get their coffee.

What are some art projects that you’re working on now?

I’m working with cities to do public art pieces. I’m trailing a little bit away from the brand stuff. I find that working with cities and developers… they know who you are in the sense that they know what they’re going to get, the end result, and they trust that. I’m doing a huge project with the city of Philadelphia where I went and spoke in front of 30 people at the community board, and they just loved it. I like working in that setting and bringing more visibility to people who wouldn’t necessarily have the ability to see art if it weren’t in front of them.


Where else are you doing these projects?

Los Angeles, Des Moines, and Detroit.

It’s not a popular question for artists, but how do you know when a piece is finished?

Man, I know. I’m like, “It’s done.” [laughs] I’m confident when it’s done. I’m confident when it’s not. I’m not lazy about it at all. With those big walls, I’ll go for a week starting at 9 am until 9 pm.

How have you seen the St. Augustine art scene change since you moved away?

I find that it’s thriving a lot. It’s awesome. There are cool kids doing cool stuff. There’s a younger community that’s bringing in more energy. They just want new things. As cheesy as it sounds, I think social media has really opened people’s eyes to what else is out there. Not that I think people are sheltered down here. I think it’s paradise.

How often to you get back to visit?

A lot, lately – probably once every three months. I’d like to buy property here at some point.

What do you like to do when you’re in St. Augustine?

I hang out with my brother and my dad. And I eat fish. I love it. All of my friends are fishermen, like Jeff [McNally], who owns The Floridian. I find that food is better down here than it is up in New York. New York’s great if you want pizza and pasta, but if you want anything remotely healthy, it’s the worst place ever. I like to eat healthy. That’s my lifestyle.

Is there anything else you want to talk about, personally or professionally?

Just that I love St. Augustine. I think it’s awesome.

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