Greenspun is best known for his extensive career in tech entrepreneurship, having "started six companies and buried 3". The most known of these companies is ArsDigita, a web development company which Greenspun founded with others in the mid 90s. ArsDigita produced a popular tool for building websites backed by databases, leading in part to the widespread use of database-backed sites today, but ultimately collapsed after (according to Greenspun) changes in management forced by venture capitalists (who had injected cash into the company following the dot com crash) ran the company into the ground. Greenspun accredits a large part of ArsDigita's success to the response times that they offered, claiming in one article that he was able to deliver results in hours that would've taken companies like Microsoft nearly a year, in part due to the company culture which was programmer-focused and in part due to his access to customer feedback. In an interview with Richard Morris of Redgate Software, Greenspun makes it seem as though venture capitalists saw what was already a high successful business model and sought to squeeze even more juice out of it, mimicking practices of other large firms such as IBM. For reasons that are not specified, the venture capitalists were diametrically opposed to the leadership style of the previous management and evacuated 80% of them, and essentially tried to force a square peg into a round hole (why they would do this after investing $38 million is beyond me).