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Brewster has built technologies, companies, and institutions to advance the goal of universal access to all knowledge. He currently oversees the non-profit Internet Archive as founder and Digital Librarian, which is now one of the largest digital archives in the world.

As a digital archivist, Brewster has been active in technology, business, and law.

After graduating from the Massachusetts Institute of Technology (MIT) in 1982, Brewster helped start a supercomputer company, Thinking Machines, that built systems for searching large text collections. In 1989, he invented the Internet’s first publishing and distributed search system, WAIS (Wide Area Information Server). WAIS Inc. created the online presence for many of the world’s largest publishers and was purchased by America Online in 1995. In 1996, Brewster co-founded Alexa Internet, which provides search and discovery services included in more than 90 percent of web browsers, and was purchased by Amazon in 1999.