Simkhai was born in
Tel Aviv, Israel. His mother was a jeweler, and his father was a diamond dealer. When Simkhai was three years old, his family moved to
New York City. While in high school, he says he dated women; he remarked that he was not being dishonest about his sexuality, but that his "coming out of the closet was a process". Simkhai received his
Bachelor of Arts degree in International Relations & Economics from
Tufts University in May 1998. After starting college, he
came out to his parents and friends. He has two brothers, who are also gay. Simkhai owns several pieces of real estate, but primarily resides in New York. In 2021,
Dave Keuning bought a mansion that Simkhai had owned in
Outpost Estates in Los Angeles. ==Business career==