We had the good fortune of connecting with Steven Simon and we’ve shared our conversation below.

Hi Steven, what was your thought process behind starting your own business?
I started my caricature business by volunteering at church festivals in my hometown, where I wanted to serve my community and put my artistic talents to good use. Having drawn caricatures since childhood, I decided to develop the skill further by taking a course at School of Visual Arts and studying instructional books. What began as a simple way to give back naturally grew into a business after I created a logo, handed out business cards, and began receiving steady requests for events.

Let’s talk shop? Tell us more about your career, what can you share with our community?
My caricature art is defined by a simple, bold black-and-white style that’s cartoonish without being overly exaggerated—capturing just the right balance of likeness and humor. I’ve built the business around that same simplicity, with a strong, recognizable brand and a focus on creating fun, memorable experiences rather than chasing profit, which is why the journey has felt natural and passion-driven. Along the way, I unexpectedly expanded into selling autographed caricatures, an exciting avenue that’s allowed me to meet notable celebrities and add a unique dimension to my work. The biggest challenge has been maintaining consistent bookings, but perseverance, continued exposure, and genuine enthusiasm for making people laugh have helped me grow steadily. Ultimately, I want people to see my brand as authentic, lighthearted, and rooted in connection—art that brings joy while telling a story.

Any places to eat or things to do that you can share with our readers? If they have a friend visiting town, what are some spots they could take them to?
My best friend is my girlfriend Elyssa, and our ideal getaway is simple—we pick one Texas town for the weekend, find a great local restaurant, and spend time drawing caricatures at a festival or community event. Whether we’re exploring Austin, San Antonio, Corpus Christi, College Station, or staying close to home in Houston, the fun comes from discovering new food, meeting people, and turning each trip into a creative, memorable adventure through art.

The Shoutout series is all about recognizing that our success and where we are in life is at least somewhat thanks to the efforts, support, mentorship, love and encouragement of others. So is there someone that you want to dedicate your shoutout to?
I’d dedicate my shoutout to my girlfriend, Elyssa, who’s supported me from the very beginning and often joins me at events as I continue to grow the business. I’m also grateful to my aunt and uncle, who encouraged me to get involved at church—while they imagined I might teach CCE, I decided to serve by drawing caricatures instead. And my education at Texas A&M University in Visualization has played a huge role as well, giving me a strong foundation in graphic design, branding, and web development that’s helped me build and promote the business professionally.

Website: https://stevensimon.art

Instagram: https://instagram.com/stevensimon50

Facebook: https://www.facebook.com/people/Caricatures-by-Steven-Simon/61557635126131/?mibextid=LQQJ4d

Image Credits
Elyssa Tobias

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