Kagasoff was born in Encino, California to Elise Kagasoff (née Levy) and Barry Kagasoff, a diamond merchant. He is the middle of three children; he has an older brother, Justin, and a younger sister, Natalie. Kagasoff is Jewish.
Kagasoff graduated from Montclair Preparatory High School in 2005 where he played on his school's baseball team. While attending school at San Francisco State University, Kagasoff decided to become an actor.
After deciding to return to Los Angeles, Kagasoff landed the lead role in a local theater production of Suburbia, a play that the eponymous 1996 film was based upon. After studying acting, he began auditioning for television and film roles. During one of his first auditions, he impressed producer Brenda Hampton so much that she hand-picked him to star as Ricky Underwood in the ABC Family series The Secret Life of the American Teenager. The show ran for five seasons.

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