[12] Following his graduation, Goldstein worked as an archivist for Robert Wilson's Byrd Hoffman Foundation and then founded Riverhead Media with multi-media artist Paul Kaiser and publisher Joost Effers.

In 1993 he received a fellowship and moved to Frankfurt, Germany where he was a multi-media artist-in-residence at the Center for Art and Media Technology, and later initiated the creation of a production and research laboratory for multimedia applications at Jeff Shaw's ZKM Institute for VisualMedia.

While there, he heard about an opportunity to create an internet presence for Duracell, and in 1995, he and David Byman co-founded SiteSpecific, an interactive marketing company.

With a staff of three, the company developed a brand awareness campaign which included seeding images of the batteries on major internet sites.

[3][16] In 1998 Goldstein joined the VC firm Flatiron Partners,[17] founded by Fred Wilson and Jerry Colonna.

[3][20] In January 2005, with Jerry Neumann and Candice Sherman, Goldstein co-founded Root Markets, a financial exchange allowing consumers to sell online data about themselves.

In September 2012, he launched DJZ, a content site which combined editorial, videos, DJ mixes, interviews, contests, and links to pages for popular DJs.

[28][29] It also offered a free iPhone app, called DJZTxT, that allowed users to create dance music through text messages using emojis.

[31] Called Crossfader, it allowed users to create their own music through an iPhone-based remix and DJ platform that used loops and filters controlled by a gyroscope and accelerometer.

[6] He has spoken at conferences including Billboard magazine's FutureSound, the IAB Annual Leadership Forum,[38] Big Omaha, and O'Reilly Web 2.0.