Wessman began to learn a variety of tattoo styles at the shop, where the clientele included sailors, pimps, and prostitutes.

[1] From 2005 to 2010, Wessman worked at Love Hate Tattoo and was featured on the TLC reality TV show Miami Ink.

After the show ended, Wessman spent some time traveling and working in Scotland, Ireland, Italy, The Netherlands, and Germany.

In 2014, Wessman designed a limited-edition postcard featuring the phrase #govote for HeadCount, a nonpartisan organization that promotes participation in democracy.

[8][9][10] In 2015, Wessman opened The Summertown Inn, a private tattoo studio in an undisclosed location in Orange County.

[1][5] The "gangster" style was influenced by the tattoos characteristic of the street culture he grew up around in Oceanside – Old English and block letters, Catholic imagery, black and gray coloring, etc.

[12] He has tattooed dozens of celebrities, including Dave Navarro, CM Punk, Matt Holliday, and Silkk Tha Shocker, among others.