The World is Yours

Drop into the life of Paint the World founder Sage Stewart

By Neal Kearney
January 31, 2025
Share:

Starting a business from the ground up is a truly risky venture. It takes capital, determination, patience, and a whole lot of luck. It also requires a product that will sell. Against all odds, forty-two year-old Sage Stewart, owner of Paint The World skateboards and apparel, has found great success with his unique and eye-catching products, and doesn’t plan on slowing down anytime soon.

From a young age, Stewart, who grew up in New Mexico, was enamored with art, and it wasn’t long until he taught himself the basics, with his favorite cartoon characters being among his first studies. At age nine, he was introduced to skateboarding. When he wasn’t working on his art, he spent most of his free time practicing grinds and flip-tricks, just like any other teenage skate rat coming of age in the 1990’s. In 2005, as his creative abilities matured and his passion for skateboarding deepened, he decided to fuse these dual interests into a career. Enter Paint The World skateboards and apparel.

The clothing and skateboard deck designs of Paint The World often include street art inspired graphics and portrayals of famous celebrities such as Tupac Shakur, Steph Curry, and Kobe Bryant. On his Paint The World website Stewart also sells prints and originals of his artwork, which also feature depictions of well-known personalities such as The Notorious B.I.G., Walter White, Marty McFly, Jimi Hendrix, and Al Pacino’s Scarface, just to name a few.

Stewart, who grew up in New Mexico, moved to Santa Cruz ten years ago, after many years of residence in Los Angeles. At that time, his art-inspired skateboard brand, had already been up and running for almost a decade. As a dedicated skater, Stewart was drawn to Santa Cruz’s rich skate culture, and spends his free time painting lines at parks and streets near and far.

Paint The World isn’t quite a globally recognized brand at this point, but that hasn’t discouraged Stewart one bit. He’s already an established artist, with his art hanging on the walls of big-name pro skaters such as Andrew Reynolds and Emmanuel Guzman, along with skateboarding film legend, Beagle. He even has five of his originals hanging in the residences of none other than Snoop Dogg, the Doggfather himself! His skateboards decks often include street art inspired graphics and portrayals of famous celebrities such as Tupac Shakur, Steph Curry, and Kobe Bryant.

I admire any small business owner with the guts to follow their dreams, especially in an industry that’s so tough to break into. To learn more about his story, I contacted Stewart for an interview, which you can read below.

Stewart, in his element

How old were you when you started creating art? Did you have any big inspirations or mentors early on? How about skateboarding?

I started creating art when I was about 5 years old. I would sit in front of the television for Saturday Morning Cartoons and draw up my favorite characters with a pencil and pad. The Teenage Mutant Ninja Turtles, Garfield, and Super Friends were my muses at the time. As I got older and my love for art grew, I began drawing human anatomy such as hands and faces, in hopes of trying to make them look as realistic as possible.

I started skateboarding when I was 9 years old after seeing the Plan B “Questionable” video at my buddies house. From that point on I was hooked on skating. Thirty-three years later, I still go out every weekend to hit the streets and stack clips.

How did you get from drawing Ninja Turtles on paper with chewed up pencils to painting portraits on canvas?

I taught myself to paint but it did not happen overnight, I needed to learn the best painting techniques with the appropriate brushes and tools. Youtube was not the vast collection of art tutorials it is now when I was first learning, so it was all observation, trial, and many errors.

Creating my designs on larger bodies of work was not too difficult to adjust to.Whether it be larger canvases, walls, or skateboards, my artistic direction and skills have adjusted well to the landscape.

Stewart, his art, and the Doggfather

Tell me about your migration to California. Is it true that upon your move you became quite tight with Snoop Dogg?

Sure. So, I was born in Philadelphia PA, but I grew up in Albuquerque NM. Once I graduated high school I immediately moved out to Long Beach, California. My good buddy lined up a job for me in East LA working for an after school program run by Arnold Schwarzenegger. I also worked for the LA Unified School District running after school skateparks.Both jobs correlated with each other well, so it was meant to be.

When I was not working for the after school programs in LA, I became a personal assistant to Snoop Dogg. Another buddy of mine who worked for Snoop introduced me to him for a family portrait painting I did for him and his family. Needless to say, he was thrilled with the artwork and the rest is history.

I have done a total of 5 art pieces for the Doggfather and it gives me great joy every time I can bless him with paintings and catch up. For a short time I also worked for SYFL which is the “Snoop Youth Football League,” which still gets kids off the streets and onto the football field. Snoop also liked that I had experience working at other after school programs and became a good fit. I learned so much from Dogg. Every time he spoke, they were words of wisdom and encouragement. I soaked up all the game like a sponge and applied it to my life today. Thank you boss Dogg!

Years later I decided to get out of LA and was lucky to come across the beach town of Santa Cruz. I have been living here happily for the last 10 years. Living in Santa Cruz gives me a similar feeling as living in Long Beach. Good people, great sunsets and ocean vibes.

That’s amazing! How did you know your artwork was something that people would be willing to spend good money on?

A good friend who got me into painting said, “You should put all of your artwork on canvases, I bet they would sell.” Immediately, it sparked a fire. The first two large canvases I painted sold right away to a Long Beach local at the prices I was listing them for. I couldn’t believe it!

It’s crazy because while I used to sell pencil sketches in high school for some loot here and there, I never thought I could sell full fledged canvases.

Possessed to skate! Stewart, gettin’ after it

What is Paint The World? How did you get the operation up and running? Where can we find your products locally?

Since 2005, Paint The World has been about creating the best pop art paintings, apparel and skateboards in hopes that others enjoy my art and products as much as I love creating them.

Now Paint The World has expanded to a skateboard company, which is a dream come true because now I can promote and skate my own boards/brand.

I was lucky enough to link up with a skateboard manufacturing company through a good buddy that makes the same skateboards as most leading skate brands today. This gave me a great advantage on marketing my skateboards to other skate shops and online. I only skate the best quality boards, therefore I want my customers to have the same experience. Nothing is easy, but the most fulfilling part for me is designing the artwork and images. My good buddy Pep The Future has been helping me with designing the skateboard and apparel graphics from the beginning.

I am proud to say that 5 skate shops across Santa Cruz, Scotts Valley, Bay Area, and Los Angeles carry PTW skateboards and streetwear. There are other skate shops in the works so wish me luck!

Stewart’s pop art is eye-catching and colorful, as evidenced by this sick Friday inspired piece

Who inspires and supports your mission the most?

Besides my parents being the most inspirational supporters and motivators in my life, there are also many artists, skateboarders and skate brands that have inspired Paint The World. As far as skaters, I’d have to include John Cardiel, Andrew Reynolds, Hearth Kirchart, Tony Hawn, PJ Ladd, Mark Appleyeard, Daewon Song, and Arto Sara. The artists who have inspired me the most are Andy Warhol, Salvador, Dali, Jean Michel-Basquiat, Leonardo Di Vinci, Vincent Van Gogh, Georgia O’Keefe, Michelangelo, and Banksy. The skate brands that get my wheels spinnin’ are Anti Hero, BAKER, Krooked, Plan B, Birdhouse, Toy Machine, and Flip.

What challenges are inherent in running a brand such as Paint The World? Any plans for the future or anyone you want to send a shoutout to?

Since it’s inception, gaining traction for PTW has always taken effort, late nights, and early mornings. Whether it’s brand awareness through social media/ads, PTW website and Google Ads, it is always a mission, but worth the trials and tribulations when the processes are learned and executed. Nowadays, I look through my website and ads analytically to gauge if they are providing the best type of brand awareness to my products and skateboards.

Steph Curry, coming to a skateboard near you!

The Big Plans for 2024-2025 is to release new skateboard designs in the skate shops and on the website. Maybe also adding a couple team riders to the PTW squad as well and creating a full fledged skate team. In the next 10 years I envision PTW in skate shops all over the U.S. and possibly in Zumiez or other retail stores.

As a business owner, I am blessed to be able to get PTW to this point. I am so happy that so many people have supported the brand for almost 20 years across the entire United States. Thank you Paint The World Family

To everyone else, always invest in yourself, because you never know where it may take you!

Visit the Paint The World Online Store  www.painttheworldofficial.com

Visit the Paint The World Etsy Store   https://www.etsy.com/shop/PaintTheWorldLLC

Follow Paint The World on Instagram @painttheworldofficial

 

The legendary Andrew Reynolds, happily posing with his Stewart original
Share: