[1] He participated in school theatre productions and studied at the Dallas Young Actors Studio for 4 years.

[6] During spring break in 2018, Raiff stayed on campus to make Madeline & Cooper, a 50-minute short film that he uploaded to YouTube.

[14] In July 2022, it was announced that Raiff wrote and would direct The Trashers, a drama about "a Connecticut trash magnate and associate of the Genovese crime family.

"[18] Raiff was given the Maverick Award at the 2022 Newport Beach Film Festival[19] and appeared on the Forbes 30 Under 30 list in Hollywood & Entertainment.

[22] Raiff has cited Emma Seligman, Sofia Coppola, Greta Gerwig, Ryan Coogler, and the Duplass brothers as influences.