Convention Connection: How Taiwanese Tattoo Artist Ollie Won Black and Grey Large at Her First U.S. Show
Ollie’s client gave her his whole leg and told her to do whatever she wanted. She chose a Greek myth: Artemis and the hunter Actaeon, who was turned into a stag after seeing the goddess bathing. Ollie is a Tattoo Artist from Taiwan with six years of experience. The Tattoo Society World Expo in New York was her first show in the United States. Chico Cortez sat down with her there for her very first interview. Later that day, he caught up with her again with big news: she’d won Black and Grey Large.
Key Takeaways
The win: Ollie won Black and Grey Large at her first U.S. convention, the Tattoo Society World Expo in New York.
The story behind it: Her piece tells the Greek myth of Artemis and Actaeon, with a half-human, half-stag skull at its center.
Her style: She likes to make dark subjects elegant, with delicate details and lots of texture.
Her training: She did a tattoo apprenticeship for about two years before tattooing clients.
What’s next: She plans to spend a year guest spotting in Europe and come to the U.S. every year.
Who Is Ollie and What Did She Win?
Ollie is a Tattoo Artist from Taiwan who has been tattooing for six years. At the Tattoo Society World Expo in New York, her first U.S. show, she won Black and Grey Large.
It was also her first interview. As Chico told her, it was an honor, because she should have been interviewed long before.
When she found out she’d won, she was overjoyed. “Everyone is so good,” she said. She could hardly find the words.
What Is a Tattoo Convention Connection?
Convention Connection is Ink Different’s interview series filmed at tattoo conventions. It’s where we meet Tattoo Artists like Ollie and share their stories.
For Ollie, the expo was a chance to show her work in the U.S. for the first time. Chico predicted she’d be back for many more shows once people saw this piece. She plans to be.
Why Do Tattoo Conventions Matter for Your Career?
Conventions put your work in front of new people. For Ollie, one show in New York led to an award and her first interview.
Competing also pushes you to bring your best work. Ollie designed her piece to showcase everything she’s good at, then entered it into a category full of talented Tattoo Artists.
Tattooing is a deeply human craft, which is why Tattoo Artists are still essential.
Pro Tip: Like Ollie, design your convention piece around the subjects you do best.
How Did Ollie Prepare for a First-Time Convention Win?
Ollie prepared with a strong foundation and a carefully planned design.
She trained the traditional way
Ollie did a tattoo apprenticeship for about two years before she started tattooing clients. She’s been tattooing for six years since.
She told a story
Her piece is based on the Greek myth of Artemis and Actaeon. As Ollie tells it, the hunter accidentally saw Artemis bathing. Angry, she shot him with an arrow, and he became a stag. That’s why Ollie centered the piece on a skull that’s half human and half stag.
The scene is set in a forest, with a raven, a snake, and flowers like irises and poppies, which she says she’s especially good at.
She designed around her strengths
When she designed the piece, she thought about what story could show every subject she’s good at. Chico noted its delicate, Art Nouveau feel. Ollie says she loves turning cool things into something elegant.
She also loves texture. Look closely, and you’ll even find silhouettes hidden in the piece.
Safety matters in every tattoo. Every Tattoo Artist must follow the OSHA bloodborne pathogens standard.
Before you start, read about the mistakes aspiring tattoo apprentices should avoid.
What Is Black and Grey Tattoo Style and Why Is It So Competitive?
Black and grey tattooing uses black ink in different values to create depth, without color. Because there’s no color to carry the piece, contrast, shading, and texture have to do all the work.
That’s what makes Ollie’s win stand out. Her large piece combines a detailed skull, wildlife, flowers, and hidden silhouettes, all held together by careful contrast and texture.
How Can You Prepare for Your First Tattoo Convention?
Step 1: Build a strong foundation. Ollie trained for about two years before tattooing clients.
Step 2: Know your strengths. Ollie designed her piece to show off what she does best.
Step 3: Tell a story. Her Greek myth concept gave the tattoo meaning beyond its technique.
Step 4: Sweat the details. Texture and hidden silhouettes made her work memorable.
Step 5: Make booking easy. Ollie’s assistant helps her reply to emails, so clients can reach her.
Step 6: Build your presence. Share your work with these platforms to help Tattoo Artists build their brand.
For gear, see the tools every beginner Tattoo Artist should know.
How Does Mentorship Turn Beginners Into Convention Winners?
Ollie’s career started with a tattoo apprenticeship of about two years. That foundation helped her build the skills she showcased in New York six years later.
Hands-on training from experienced Tattoo Artists gives beginners real-time feedback and a clear path forward. That’s why we believe a tattoo apprenticeship is a serious alternative to college.
What Can You Expect From Ink Different's Tattoo Training?
Ink Different Tattoos offers the Traditional Tattoo Apprenticeship, built for beginners, with hands-on mentorship and licensing support. Ink Different has trained Tattoo Artists for 15 years, with a “Good Humans” culture at its core.
Get Serious About Your Craft With Ink Different Tattoos
If you’ve been thinking about tattooing, this is your sign. Seats are limited, with only two apprentices per tattoo studio per Mentor.
What You Can Expect From Our Traditional Tattoo Apprenticeship
Length: 18 to 24 months across four phases.
Format: Hands-on, in-person mentorship from experienced Mentors inside a working tattoo studio.
Beginner-friendly: No prior art experience required.
Outcome: Job-ready skills, licensing support, and a guaranteed job offer at one of Ink Different’s own tattoo studios.
A Career That Comes With Confidence
This is a career that comes with confidence. You’ll finish with job-ready skills, licensing support, and a guaranteed job offer at one of Ink Different’s own tattoo studios. The Traditional Tattoo Apprenticeship is available at 60+ tattoo studios nationwide.
Mentorship That Pushes Your Brand and Skills Further
Once you’ve built your foundation, Ink Different’s Master Mentorship connects you with Master Mentors, including Al Fliction, Liz Cook, Kyle Dunbar, Boneface, Jordi Pla, Marcel Oliveira, and Kara Gutierrez. It’s where Tattoo Artists go deeper into a signature style, like Ollie’s elegant, textured black and grey.
Making Tattoo Training Accessible for Everyone
Ink Different offers Spanish-speaking locations in Denver, Orange County, NYC, Miami, San Antonio, and San Diego.
Ready to Build Your Own Convention Story?
Ollie came to the U.S. for the first time, gave her first interview, and won Black and Grey Large, all at one show. She loves to travel and plans to guest spot in many places. Next year, she plans to spend a year traveling around Europe, and she says she’ll come to America every year.
Ready to become a Tattoo Artist? Apply now to Ink Different’s Traditional Tattoo Apprenticeship and start building an AI-proof career with licensing support and a guaranteed job offer at one of Ink Different’s own tattoo studios. Prefer to explore first? Fill out our quick questionnaire to see if it’s right for you.
To book with Ollie, follow her on Instagram at @ollieeeee.tattoo to see where she’s traveling next. Her assistant helps reply to booking emails. Follow Chico at @m4l_chico.
Frequently Asked Questions
What did Ollie win?
She won Black and Grey Large at the Tattoo Society World Expo in New York, her first U.S. tattoo convention.
What is Ollie’s award-winning tattoo about?
It tells the Greek myth of Artemis and Actaeon, the hunter turned into a stag, with a half-human, half-stag skull surrounded by a raven, a snake, irises, and poppies.
How long did Ollie apprentice?
About two years, before she started tattooing clients. She’s been tattooing for six years.
How can I book a tattoo with Ollie?
Follow her on Instagram at @ollieeeee.tattoo. Her assistant helps manage booking emails.
How long does the Traditional Tattoo Apprenticeship take?
Ink Different’s Traditional Tattoo Apprenticeship takes 18 to 24 months across four phases, with licensing support and a guaranteed job offer at one of Ink Different’s own tattoo studios.
Do I need prior art experience to start?
No. The Traditional Tattoo Apprenticeship is built for beginners.
Related reading: career change tattoo apprenticeship, why spring is the best time to become a tattoo artist, and tattoo apprenticeships as a college alternative.
