Born in Uruguay, Bolioli migrated to the United States, where he studied at the prestigious School of Visual Arts in New York City. Unable to balance his passions of art and surfing, he moved to Hawaii. During his early days in the islands, he made a living painting surfboards for world champions like Shaun Tomson, Martin Potter, and Sunny Garcia. Later, seeking to develop new ways to paint surfboards, he discovered Posca markers, developing a whole new way to paint boards. He soon became an art director for Blue Hawaii Surf and Local Motion while also designing for Quiksilver, Gotcha, and Billabong. In 1992, he became the ABSOLUT HAWAII artist in a campaign that was published nationwide — leading to a move back to his native country, Uruguay to work on the ABSOLUT URUGUAY campaign.