He was descended from immigrants who arrived in Massachusetts in 1630. His father, George Whitney, was a leading Boston banker. Whitney graduated from Groton and from Harvard, where he was elected to the prestigious Porcelland Club. He moved to New York City in 1910 and became a member of the New York Stock Exchange in 1912, at the age of twenty-three. Soon afterward he was principal broker for J. P. Morgan and Company, of which his brother, George, was later vice-president. During WWI, Whitney was a dollar-per-year executive for the Food Administration, headed by Herbert Hoover, in Washington, D.C. In the 1920's Whitney was a member of every major club and organization to which a member of the eastern aristocracy should belong. He was treasurer of the New York Yacht Club. He had large and opulent estates; he bred horses; and he was reputed to spend $5,000 per month on maintenance alone, a huge figure for that time. He was married in 1916 to a young widow, Gertrude Sheldon Sands; they had three children. Whitney took over her father's investment business, Cummings and Markwald, and immediately renamed it Richard Whitney and Company. In 1919 he was elected to the governing board of the New York Stock Exchange.