Following his high-school graduation Berkowitz spent two years studying religious texts as the Yeshiva Kol Torah in Jerusalem, and enrolled in the Ner Israel Rabbinical College in Baltimore, Maryland upon returning to the U.S. in 2009.
From there he transferred to Queens College where he completed his undergraduate degree. Berkowitz met Donald Trump's son-in-law Jared Kushner at a Passover celebration in Phoenix, AZ while he was attending Queens College, and the two immediately hit it off.
Following his college graduation, Berkowitz was hired by Kushner to help manage the Kushner family real-estate firm's apartment portfolio. After leaving the Kushner Real Estate Group to pursue higher education at Harvard Law School, Berkowitz regularly contributed articles to the New York Observer, a publication owned by Kushner's Observer Media group.
Although he had accepted a position at the law firm Gibson Dunn, as Donald Trump's Presidential campaign gained momentum it became clear that Berkowitz was going to have to postpone his original post-graduate plans. He joined the Trump campaign as Assistant Director of Data Analytics in early 2016, and following a come-from-behind victory, headed to the White House.