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Conversations with James Osgood

Today we’d like to introduce you to James Osgood

Hi James , thanks for joining us today. We’d love for you to start by introducing yourself.
I began drawing at the age of 5, captivated by comics, anime, and the graffiti on passing trains. Over time, I developed a strong eye for detail and a passion for realism—recreating images from references—and that drive to improve never faded. I was always pushing myself to capture more detail and refine my skills. A few years later, another artist suggested I try tattooing. At first, I didn’t think it was something I could do, but the thought of creating art all day, every day, kept me up at night. It quickly became all I wanted to pursue. So, I took the leap and haven’t looked back since. Today, I’m proud to say we own a tattoo shop surrounded by talented artists who push each other to improve every day.

We all face challenges, but looking back would you describe it as a relatively smooth road?
Of course, it wasn’t easy. Before tattooing, I was a barber for five years, and for a long time, that was my main focus. I was lucky to have great clients and even my own barbershop. But then, out of nowhere, this desire to tattoo hit me. Suddenly, I had to make a decision: Do I walk away from a craft I’d worked so hard to master and start over from scratch with something completely new? I just couldn’t ignore the urge to try, so I made a plan. I’d cut hair all day and tattoo at night and on weekends.

When I finally transitioned to full-time tattooing, it was tough. Late nights, barely making any money, and constantly being hard on myself. The first shop I worked at wasn’t exactly a great learning environment, so most of my growth came from trial and error or watching artists I admired. In a way, though, that was a blessing. It taught me how to be resourceful and pushed me to find solutions through the challenges.

As you know, we’re big fans of you and your work. For our readers who might not be as familiar what can you tell them about what you do?
The word “specialize” is a tough one for me because, as much as I love realism and portraits, I don’t want to limit myself to just that. I simply want to create dope art in whatever form it takes. If I had to pick an area I love most, though, it would be realism and portraits. They’re incredibly challenging, but when you get it right, the satisfaction is unmatched. Plus, there’s always room to learn and grow within realism, because there are so many different subjects to choose from, each with its own challenges and opportunities. One project’s difficulties can teach you how to improve on another subject, and that’s something I really appreciate.

What I’m most proud of is the chance to build relationships with some of the amazing artists I look up to in this industry. As for what sets me apart, I don’t know if there’s a clear answer. What I do know is that I love what I get to do every day, and I take it very seriously. That passion translates into how I interact with my clients and the environment around me, fostering a constant desire to grow and challenge myself.

What do you like best about our city? What do you like least?
I love the diversity, we have so many people from so many walks of life which I feel creates more opportunity to learn and push everyone outside of their own box of comfort. the thing I love least is winter for sure!

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