He started his pornographic career two years later, and has since been frequently regarded in the media as one of gay pornography's most recognizable and lauded stars, particularly for his large penis, "daddy" image, and entrepreneurship.

During this time, he had received a Juris Doctor degree and moved to New York City to take the bar examination in the hopes of becoming a criminal defense lawyer.

Prior to starting his pornographic career, Steele worked at a corporate job in retail in New York City, which he has said made him depressed.

[6] In 2012, while in his 40s,[3] Steele began working as an escort, using Rentboy to post ads for himself, and was given offers by various gay pornographic studios, which he declined.

[7] Steele made his pornographic directorial debut in 2015 with the Dragon Media film Urban Legend, which was nominated for two Grabby Awards.

[20][21] In January 2020, Steele sold nude photos of himself through direct messages on his Twitter account to raise money to combat wildfires in Australia.

[27][4] For Fleshbot, Vincent Thrice wrote that he had "taken the gay porn world by storm" in 2014 and that he had "what can only accurately be described as a monster cock".

[28] In 2015, Marke Bieschke of Vice wrote that "Steele's cock-rocket to the top has been meteoric, the result of a blast of self-confidence, social media engagement, free porn clips, and a razor-sharp marketing plan" and described him as the "archetypal daddy".

[6] In 2018, Derek de Koff of Queerty called him "one of the top entertainers in gay adult films for the last seven years" due to his "burly dad bod" and "not-for-the-faint-of-heart appendage".