Greenspun grew up in Bethesda, Maryland, and received a B.S. in Mathematics from MIT in 1982. After working for Hewlett Packard Research Labs in Palo Alto and Symbolics, he became a founder of ICAD, Inc. Greenspun returned to MIT to study electrical engineering and computer science, eventually receiving a Ph.D.

Working with Isaac Kohane of Boston Children's Hospital and Harvard Medical School, Greenspun was the developer of an early Web-based electronic medical record system. The system is described in "Building national electronic medical record systems via the World Wide Web" (1996).[1] Greenspun and Kohane continue to work together on a medical informatics at Harvard Medical School.

In 1995, Greenspun was hired to lead development of Hearst Corporation's Internet services, which included early e-commerce sites. In 1997 he co-founded ArsDigita, a web services company which grew to $20 million in annual revenues by 2000.
Photo.net and ArsDigita

In 1993, Greenspun founded photo.net, an online community for people helping each other to improve their photographic skills. He seeded the community with "Travels with Samantha",[3] a photo-illustrated account of a trip from Boston to Alaska and back. Photo.net became a business in 2000 with the help of some of his cofounders Rajeev Surati and Waikit Lau. Having grown to 600,000 registered users, it was acquired by NameMedia in 2007 for $6 million, according to documents filed in connection with a planned public offering of NameMedia shares. Greenspun founded the open-source software company ArsDigita and, as CEO, grew it to about $20 million in revenue before taking a venture capital investment.

Greenspun was an early developer of database-backed Web sites, which became the dominant approach to engineering sites with user contributions, e.g., Amazon.com. Greenspun was also a developer of one of the first Web-based electronic medical record systems. Greenspun's Oracle-based community site LUSENET was an important early host of free forums.
Aviation

Greenspun has written several textbooks on developing Internet applications, including Philip and Alex's Guide to Web Publishing,[21] SQL for Web Nerds,[22] and Software Engineering for Internet Applications,[23] the textbook for an MIT course. Greenspun is the editor of Medical School 2020, which provides a first-person account by a medical student.[24]
Teaching

Greenspun and his co-founders at ArsDigita started a non-profit foundation that ran the ArsDigita Prize, an award for young web developers, and the ArsDigita University, a tuition-free one-year program teaching the core computer science curriculum, one course at a time. Winners of the Prize include a 12 year old Aaron Swartz.[25]

Greenspun has taught electrical engineering and computer science at MIT.[26] One of Greenspun's most famous students is Randal Pinkett, who built an online community for low-income housing residents in Greenspun's 6.171 Software Engineering for Internet Applications course. Pinkett went on to win NBC TV show The Apprentice. In 2003,

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