When O'leary Richardson realized he was capable of bringing a vision to life on his own terms, he decided to start his graphic design and web development business SoCreative Designs in 2009. Three years later, Richardson's launch of Creative Clothing, Anguilla's official urban clothing line, created a buzz that even caught him by surprise. Learn more about his start as an entrepreneur, the early beginnings and lasting impact of Creative Clothing, and his advice for budding business owners.
Never give up. You have to put in the work and dedication, and failure should never be in your vocabulary.
Shanice: How did you get your start in graphic design and brand development, and when did you decide to branch out to start your own business SoCreative Designs?
O'leary: At 27, I was unsure about what I wanted to do professionally in life, but throughout my schooling, art has always been a part of me. When I started Party Access in 2008, I had to pay other people to design for me, and I just decided to do everything myself, and that's where it all started for me. In 2009, I ventured out and started SoCreative Designs. The name was actually inspired by the birth of my daughter Senaiya that year so the "So" in SoCreative is her first initial combined with my own.
When customers decide to work with SoCreative Designs, what can they always expect to get from you and your team?
Stunning, eye-capturing visuals and creativity across the board.
Let's talk about some of the do's and don'ts of branding. What are some common mistakes that people make, and how can they avoid them?
I don't think people take protecting what's theirs seriously. I always try to encourage all of my clients to copyright their material because you never want anyone to copy your work without your permission.
O'leary: At 27, I was unsure about what I wanted to do professionally in life, but throughout my schooling, art has always been a part of me. When I started Party Access in 2008, I had to pay other people to design for me, and I just decided to do everything myself, and that's where it all started for me. In 2009, I ventured out and started SoCreative Designs. The name was actually inspired by the birth of my daughter Senaiya that year so the "So" in SoCreative is her first initial combined with my own.
When customers decide to work with SoCreative Designs, what can they always expect to get from you and your team?
Stunning, eye-capturing visuals and creativity across the board.
Let's talk about some of the do's and don'ts of branding. What are some common mistakes that people make, and how can they avoid them?
I don't think people take protecting what's theirs seriously. I always try to encourage all of my clients to copyright their material because you never want anyone to copy your work without your permission.
You took on the task of designing and launching Anguilla's official urban clothing brand, Creative Clothing. What was going through your mind when you first conceptualized the idea?
That idea was actually a fun thing for me. I actually did it for an Anguilla Day boat ride competition in 2012. You had to design a creative t-shirt in Anguillian colors, and I was in Holland at the time brainstorming ideas. I pitched an idea to my younger brother, who's in the same field as me, and I put my creative spin on what he came up with. When I came back to Anguilla, people gravitated to the design and started contacting me constantly asking how they could get one. I decided to push the brand further and officially launched it the carnival of 2012 because I've been to a lot of places, namely New York and Miami for carnival season, and it's rare that you'll find something in the mix that represents Anguilla. This brand made Anguillians more recognizable and put us somewhere on the map. When people see our designs, they'll be able to identify who we are.
Your line has gained a massive amount of popularity in and outside of Anguilla and has especially resonated with a younger crowd. Did the response you received take you by surprise at all?
It did. I didn't expect it to take off the way it did. I sat down with my cousin, and we tried to strategize how we could get this brand to the masses so because Anguillians respect their bands, we utilized band members to wear our designs when we first launched. Since then, the rest is history. We're here.
That idea was actually a fun thing for me. I actually did it for an Anguilla Day boat ride competition in 2012. You had to design a creative t-shirt in Anguillian colors, and I was in Holland at the time brainstorming ideas. I pitched an idea to my younger brother, who's in the same field as me, and I put my creative spin on what he came up with. When I came back to Anguilla, people gravitated to the design and started contacting me constantly asking how they could get one. I decided to push the brand further and officially launched it the carnival of 2012 because I've been to a lot of places, namely New York and Miami for carnival season, and it's rare that you'll find something in the mix that represents Anguilla. This brand made Anguillians more recognizable and put us somewhere on the map. When people see our designs, they'll be able to identify who we are.
Your line has gained a massive amount of popularity in and outside of Anguilla and has especially resonated with a younger crowd. Did the response you received take you by surprise at all?
It did. I didn't expect it to take off the way it did. I sat down with my cousin, and we tried to strategize how we could get this brand to the masses so because Anguillians respect their bands, we utilized band members to wear our designs when we first launched. Since then, the rest is history. We're here.

Right now the three standard designs people can buy are Rep Your Deuce, 35 Square Miles, and Rep AXA. Any new designs we can look forward to seeing in the future?
You never know, but those three brands symbolize us, and that's what we're known for. Especially the deuce. Everyone wants one no matter how often we print the additional designs. That's our signature.
What are some valuable lessons that you've learned as an entrepreneur that you would like to share with those who are planning to start their own businesses?
Never give up. You have to put in the work and dedication, and failure should never be in your vocabulary. There will be times when you feel like things aren't working out the way you planned. I felt like that at times when I first started, but I look at where I am today and how far I've come to keep me motivated. Keep the focus.
You never know, but those three brands symbolize us, and that's what we're known for. Especially the deuce. Everyone wants one no matter how often we print the additional designs. That's our signature.
What are some valuable lessons that you've learned as an entrepreneur that you would like to share with those who are planning to start their own businesses?
Never give up. You have to put in the work and dedication, and failure should never be in your vocabulary. There will be times when you feel like things aren't working out the way you planned. I felt like that at times when I first started, but I look at where I am today and how far I've come to keep me motivated. Keep the focus.
Follow O'leary:
Website: www.olearyrichardson.com
Creative Clothing: www.creative-clothing.com
Facebook: Creative Clothing | SoCreative Designs
Twitter: @OlearyTheArtist
Website: www.olearyrichardson.com
Creative Clothing: www.creative-clothing.com
Facebook: Creative Clothing | SoCreative Designs
Twitter: @OlearyTheArtist