Raphael Milano

Connect What inspired your most recent tattoo?

Lately, my tattoos have been shaped by the rhythm of everyday life—quiet moments, passing thoughts, and the stories that unfold in between. My friends, like living canvases themselves, inspire me with their energy and vision. And then there’s the culture—constantly shifting, evolving—pushing boundaries and redefining meaning. Each piece I get is a reflection of that movement, a permanent echo of something fleeting. A mark of where I’ve been, and where the world is g

If your ink could speak, what would it say?

If my ink could speak, it would talk about legacy—the people and moments that shaped me, and the mark I hope to leave behind. It would tell stories of creativity, of turning thoughts and emotions into something visual and lasting. And it wouldn’t shy away from my vulnerabilities. It would be honest about the struggles, the growth, and the parts of myself I’ve learned to embrace through the process. Each tattoo says something I might not always have the words for.

What would you do with the $25,000?

If I win $25,000, I’d use it to keep pushing forward on my quest for creativity, culture, and style. That means investing in my craft—whether it’s new projects, collaborations, or expanding the spaces where I create and connect. I’d seek out experiences that inspire growth—travel, art, conversations that shift perspective—and bring those influences back into everything I do. More than anything, I’d use it to build something meaningful, something that ref