After practicing criminal law in New York City briefly, he became a Wall Street investment banker, co-founding Compufund, one of the first mutual funds to use statistical analysis with computers.
Goodstein founded and chaired the Whitman-Radclyffe Foundation for LGBT individuals dealing with drug abuse and also built a national network of gay political fundraisers.
Goodstein's approach to LGBT political activism was controversial in its own time for being class-based, narrow in its goals, and exclusionary, as well as projecting "a 'respectable' bourgeois image."
According to historian Robert O. Self, Goodstein was among activists attacked as "a small cabal of elitists" by others seeking LGBT rights in 1973 for allegedly grounding their politics among wealthy lesbians and gay men who were "insulated from ordinary homosexuals."
He sought to limit the breadth of inclusion in a campaign for federal gay rights by seeking "to suppress 'gay spoilers'" by keeping them off broadcast media.