He is the founder, CEO, and majority owner of Ashkenazy Acquisition Corporation, which has a $12 billion property portfolio.
[1][3] His company holds a long-term lease agreement with the City of Boston for Boston's Faneuil Hall Marketplace, leases Washington DC's Union Station, and has a $70 million stake in New York's Plaza Hotel.
[3][5] In November 2019, his company purchased the 83,923-square-foot Ferndale Shopping Center in Larchmont for a price exceeding $35 million.
[1][5][7] He hired rapper Drake to perform at his daughter's bat mitzvah in the Rainbow Room.
[1][3] Ashkenazy is a minority owner of Euroleague Basketball club Maccabi Tel Aviv B.C.