[3] Cottle is the founder of the now-defunct forum-image site 420chan and its sister-site Taima.tv, which majorly consisted of imageboards about pro wrestling (where its board was known as "/wooo/", which spawned the /wooo/tube station on Taima.tv), recreational drug use, and LGBT+ and transgender topics.

During this time Anonymous began trolling and "raiding" other websites, online games and chat rooms, as well as black-hat hacking: targeting Hal Turner, The Church of Scientology and others.

[6][7] However, in 2020 Anonymous re-emerged following the George Floyd protests, performing the June 2020 BlueLeaks breach in which they publicly released a large amount of hacked U.S. law enforcement data.

[11] In November 2020, Cottle was responsible for exploiting security flaws in Parler, a social networking service popular with the right wing, to spoof posts to appear as though they were from a verified account belonging to Ron Watkins.

[14] In August 2021, Cottle and open source intelligence analyst Libby Shaw were among the researchers who exposed the developer behind QAlerts, an app used by QAnon adherents to read posts from the anonymous "Q".

[17][18] In 2020, Cottle joined the white hat hacking group Sakura Samurai, and was involved in the January 2021 disclosure of a United Nations breach, which exposed more than 100,000 private employee records.