[5] Preston, originally from Louisville, Kentucky, left her home town at age 19, moving to Los Angeles where she transitioned, and experienced a period of homelessness, sex work and drug use.
A video of the event, which included Preston calling Jenner a "fucking fraud" over her support of US president Donald Trump, went viral online.
[9] In a subsequent interview with TMZ, she expressed concern about the alignment of those such as Jenner along with Harvey Levin, who she saw as supporting a political agenda which was antagonistic of the LGBTQ community.
[12][6] She is the host of the podcast REVRY Studio's SHOOK with Ashlee Marie Preston, which covers topics related to discrimination,[6] and she has contributed her writing to outlets such as Teen Vogue and Vice.
[16] She also led a movement to boycott the radio show The Breakfast Club, after host Charlamagne tha God "appeared to goad comedian Lil Duval into making statements about killing trans women".
[7] She, along with Patrisse Cullors of the Black Lives Matter movement went on to disrupt an event featuring Charlamagne tha God at Politicon in protest.
In October 2019 while feuding with supporters of 2020 presidential candidate Bernie Sanders over his absence from two LGBTQ forums, tweets made by Preston from 2010 through 2018 resurfaced, described as racist, homophobic, and threatening violence.