The first few people to let the self-taught Winter tattoo them were his little brother and his best friend. He had practiced on a ton of different materials and was finally ready for the real deal — even though he was full of nerves and anxiety. "As soon as I put the needle in the skin and started to do my thing, I thought, this is going to be something," said Winter. "I just knew right away — I can't explain it. It was kind of like a gift was just sitting in my body dormant, waiting for this moment."
That day set the ball in motion. In 2011, he decided to "roll the dice" and open up a private studio with other artists — not tattooers, but designers and painters. "I wanted to break the mould and show people that you don't have to do things traditionally to become something," said Winter." Instagram was just starting up and he was utilising it as much as possible, and things "took off from there."
"When I picked up the machine for the first time and saw how naturally it came to me, I knew this was what I was going to do. I was all in. I never ever looked back, not once."
As a third-generation native of Beverly Hills, Winter grew up alongside A-listers his whole life — he went to Beverly High, after all — and it was through word of mouth that he landed his first four celebrity clients in 2016, all at once from the cast of Pretty Little Liars. They shared the work on Instagram and the next opportunity followed immediately. "I got a text message from Miley Cyrus saying, 'Hey, I want to come in and get tattoos. I heard you do cool fine-line work,'" said Winter.
The next thing he knew, Winter was at Cyrus's house tattooing her Happy Hippie Foundation logo — the smiley face with the two H's for eyes — on her inner arm. "I don't know what I was thinking, but I let her tattoo it on me," said Winter. "And it's pretty funny — I mean, it's horrible, but it's funny."