Gogulski was born in Phoenix, Arizona, but his family moved to Orlando, Florida, soon after due to his father's job as an electromechanical engineer.

[1] He attended Lake Howell High School, where he was a National Merit Scholarship Program finalist and a brain bowl team member; he graduated in 1990.

[1][3] In April 1992, while still a student there and living in Casselberry, Florida, he became the first person to be arrested by the Orange County Sheriff's Office for computer hacking.

[1] Gogulski renounced his citizenship in December 2008, though his name did not appear in the Internal Revenue Service's Quarterly Publication of Individuals Who Have Chosen to Expatriate until February 2011.

[8][9] In 1999, Gogulski founded the Connecticut Cannabis Policy Forum, which aimed to remove all penalties for adult marijuana consumption.

[11][12] As a software developer, Gogulski has contributed open source code on GitHub, including a PHP library for the decentralised digital currency bitcoin.