After Yale, Obolensky became a writer working for Telavid Inc. Imports, and went on to serve with the United States Navy as a pilot. In 1957, he formed a publishing firm McDowell, Obolensky Inc. with a partner, David McDowell. The firm published James Agee's Pulitzer Prize novel, A Death in the Family, and was the U.S. publisher for Chinua Achebe's Things Fall Apart. It was dissolved in 1960. Obolensky then formed a second publishing house, Ivan Obolensky, Inc. This firm continued through 1965, when he joined the investment banking firm of A. T. Brod & Company as a partner.The publishing house continued until 1968 under the name Astor-Honor. Throughout his main career on Wall Street as a financial analyst, Obolensky covered many prestigious accounts. He was Vice President of Moseley, Hallgarten, Estabrook & Weeden Inc., Stock brokers and Vice President of Shields & Company. Obolensky was an active member of the philanthropic community in New York. He was, for many years, an active supporter of the Soldiers', Sailors', Marines', Coast Guard and Airmen's Club, and New York's International Debutante Ball, which benefits the club. He was also Treasurer of the Russian Nobility Association in America, Inc., and the US Prior of the Orthodox Order of St. John.
Personal life
Obolensky first married in New York City on October 10, 1949 to Claire Elizabeth McGinnis. Claire was educated at the Convent of the Sacred Heart in San Francisco, the Finch Junior College in Manhattan, and at Miss Burke's School in San Francisco. She was the daughter of Felix Signoret McGinnis, vice-president of the Southern Pacific Company, and Clara McGinnis. Before their divorce in 1956, Ivan and Claire were the parents of one daughter and two sons:
Princess Marina "Maria" Ivanovna Obolensky, who married N. Carlton. She later married William D. Folwick.
Prince Ivan Ivanovich Obolensky, who married Mary Jo Smith without issue.
Prince David Ivanovich Obolensky, who married Mary Catherine Hicks on March 21, 1981.
After their divorce, Claire married designer and art advisor Garrick C. Stephenson. On October 22, 1959, Obolensky married for the second time to Mary Elizabeth Morris. Together, they were the parents of one son:
Prince Sergei Ivanovich Obolensky, who married Ceceila Justice in 1986.
Descendants
Through his son David, he was the grandfather of Princess Natalya Elizabeth Davidovna Obolensky and Princess Octavia Willing Davidovna Obolensky. Through his son Serge, he was the grandfather of Prince Alexander Sergeivitch Vasily Obolensky and Prince Christopher Sergeivitch Chapman Obolensky.