Fleming used YouTube to hone his skills through the webseries Gayle. In the webseries, Fleming plays Gayle Waters-Waters, a high-strung suburban mom in Massachusetts. During its 40 episode-run, Gayle gained the attention of other names in comedy such as Margaret Cho. Writing and directing the series, Fleming drew upon his background studying theater at Skidmore College. Fleming’s YouTube channel has now over 200,000 subscribers, and he has used the platform to skewer everything from current Secretary of Education Betsy DeVos and theater students at NYU. As a genderqueer performer, his comedy routines critique the culture of toxic masculinity and serves as a role model for the “freaks and geeks” of the world.