We sat down with Jackson to unpack the story behind the strokes—his humble beginnings, bold decisions, and the fire that keeps his pen moving and his heart motivated.

From Sketches to Calligraphy: The Early Years

Jackson was born in Registro, Brazil to a hardworking family. His father was an electrician and his mother – a homemaker with her hands full. He started working at just 15 years old, and while his first job in retail lasted only a week, it left a lifelong impression. After being let go, his boss gave him advice that would stick with him: “Find a job you love."

That love? Drawing.

Soon after, Jackson found work as an architectural draftsman at the city hall in Registro. While this kept him busy putting pen to paper, there was a creative element missing. After locking in a job as a draftsman, he found work as a cartoonist. So during the day, he would sketch building plans by hand. By night, he submitted cartoons to the local newspaper. “I was always drawing,” Jackson recalls. “Even if it wasn’t cartoons, it was still something creative.”

From Graphic Design to Finding His Flow

After a few years of architectural work, Jackson sought formal education to further his career in creative arts. With limited resources, he worked at a print shop and eventually discovered a career path he hadn’t considered before: graphic design. It was a revelation. “Someone walked into the print shop and said, ‘Why don’t you study graphic design?’ I didn’t even know what it was at the time.” But soon after Jackson realized that he in fact was a graphic designer already, just without a proper degree and training.

So Jackson pursued a degree in graphic design and later earned a scholarship for postgraduate work in business administration—something he felt would help him someday run his own studio.

For over a decade, Jackson worked as a designer. But eventually, he felt his creative energy running low. “I needed something to recharge my creative battery,” he says. That’s when a friend invited him to a lettering workshop. “It was May 2010. I still remember the exact day,” he says. “That’s the day I fell in love with letterforms.”

The Leap: Becoming a Full-Time Lettering Artist

That workshop sparked something deeper. Jackson began studying type, calligraphy, and hand-lettering intensely, posting his progress to social media. The response was overwhelming. Within two years, he had enough freelance lettering work to leave his day job and become a full-time artist.
But it wasn’t easy for the Brazilian native.

“There were moments when I had no projects,” Jackson admits. “So I had to get creative—selling digital brushes, teaching workshops, finding ways to keep going.” And then there was the language barrier. As international clients took notice, Jackson realized he’d need to improve his English to hold meetings and navigate new opportunities.

He enrolled in an English school in San Francisco for six weeks—another leap of faith that paid off for him.

Moving to the U.S. & Chasing the Dream

Years later, Jackson and his family made a bold move to the United States. “It was scary,” he recalls. “I didn’t have a regular job. I came here to work as an independent artist.” But it was also a continuation of his lifelong philosophy: face challenges head-on and believe in yourself.

Now based in the U.S., Jackson is thriving—not just as an artist, but as a role model. “I don’t want to be better than anyone else. I want to be better than who I was yesterday,” he says.

His work has been featured around the world, and his story has inspired thousands of people online. “When someone tells me, ‘You inspired me to start learning calligraphy,’ that’s better than money,” he says. “That fills my cup.”

More Than Ink on a Page

Today, Jackson continues to push his work further while raising a family that shares his love of creativity. “My daughters draw better than I did at their age,” he laughs. “But I teach them what I learned—follow your dreams, believe in yourself, and know that anything is possible.”

For Jackson, success isn’t about fame or fortune. It’s about doing what you love and lifting others as you climb. His legacy is one of letters—but the message is clear:

Seize the DIA.