We talked to this Toronto tattoo artist about finding the magic when art becomes a business
It's no secret that Toronto’s creative scene is bursting with talent, and Jared Burton, better known as Softboy, is a prime example.
As a tattoo artist who’s made waves with his whimsical designs and unique style, Softboy has managed to turn his love for art into a full-time career. His story is one of passion, hustle, and the right tools — like Squarespace — to help bring his dreams to life.
This interview has been condensed and edited for clarity.
From the Caribbean to the 6ix
Growing up in Barbados, Softboy was always the kid with a pencil in hand, sketching out his imagination on any piece of paper he could find. But turning that passion into a career wasn’t straightforward. After earning a degree in Studio Art, he dabbled in various creative fields — selling paintings, working in galleries, and competing in art shows — but something was missing. The fine art world felt exclusive, and he wanted his art to be accessible to everyone.
That’s when tattooing caught his eye. After getting his first tattoo, he was hooked — not just by the ink but by the way tattooing could connect people with art on a personal level. Determined to dive in, he packed his bags and moved to Toronto, where he landed an apprenticeship and started his journey as a tattoo artist.
Finding his style & standing out
Softboy’s tattoos aren’t just ink on skin: they’re stories, emotions, and pieces of art that his clients carry with them for life. His style is playful and imaginative, filled with intricate line-work and elements of space and nature. It’s the kind of art that makes you stop scrolling on Instagram and hit follow.
Turning art into business
Running a business, especially one centred around your art, isn’t always easy. For Softboy, the biggest challenge has been managing all the behind-the-scenes stuff.
"One of the biggest challenges I face with an art-based business isn’t actually related to art," Softboy shared. "What I find challenging is managing everything else the business requires; emails, inventory, social media consistency, etc. The best way I’ve found to overcome those challenges is to get help where I can and to create dedicated time in my schedule for certain tasks."
When Softboy decided to launch a website for his growing business, he wanted a platform that could match his creative vision. That’s where Squarespace came in. With its customizable design options, Squarespace gave him the freedom to create a website that’s as unique as his art.
"My website is the face of my business," Softboy said. "A lot of clients find me online, and Squarespace makes it easy for them to reach out and book a session."
Making life easier with Squarespace tools
One of Softboy’s favourite tools is Acuity Scheduling, a Squarespace brand and an easy scheduling solution that's been a game-changer for his business. Instead of endless back-and-forths trying to set up appointments, his clients can now book sessions directly through his website at a time that works for them. It’s a small feature that makes a big difference in managing his time and workload.
But it doesn’t stop there. "One of my favourite features Squarespace offers are email campaigns. Over the years I’ve built an email list called the 'Softcast,' which I use to connect with clients about new tattoo designs, exclusive projects, and discounts," Softboy shared.
For anyone thinking about taking the plunge into entrepreneurship, Softboy has some advice: "If there’s something you’re passionate about, don’t let fear hold you back. Start small, keep pushing, and you’ll find your way."
Whether you’re an artist like Softboy, a solopreneur, or running your own small business, Squarespace isn’t just a website builder — it’s your all-in-one e-commerce solution. Need to build a site that stands out and makes it easy to sell your products or services? Squarespace has you covered.
With sleek, customizable templates and stunning design features, it’s the go-to platform for anyone looking to turn their passion into a thriving business. Whether you’re selling your time, skills, content, services, or physical goods, Squarespace can help you make it happen.
To learn more about Squarespace, visit their website and follow them on Facebook or Instagram.
Participants attending a DMZ workshop.
DMZ Masterclass participants mingle at a workshop. 
