Lipstein has a degree in mathematics from Haverford College.
[1] He began writing for the student newspaper at Haverford College, eventually becoming its editor, and took a creative writing class.
He began writing microfiction and other creative writing, and eventually wrote five unpublished manuscripts which he considers "embarrassing".
He submitted a manuscript about a young writer to publishers under a pseudonym, hoping that they would believe he was an established writer trying to hide his identity.
He is married to Mette Lützhøft, a podcaster for Barron's.