Having been influenced by Josef Škvorecký, Danilo Kiš, Jaroslav Hašek and especially the writings of Franz Kafka;[4] Keen relocated to America, where he earned a master's degree in political science from the University of California, Berkeley, studying under Ken Jowitt.

The firm folded in April 2000 and after the demise of Audiocafe.com, Keen worked at various technology companies including Pulse 3D, SLO Media, Santa Cruz Networks, Jazziz Digital and Pure Depth, where he was director of global strategic sales.

[6] In 2013, Keen founded FutureCast, a salon-style event series hosted by the AT&T Foundry and Ericsson, which brings together start-up entrepreneurs, investors, and technologists to discuss the digital revolution.

In 2005, Keen wrote that Web 2.0 is a "grand utopian movement" similar to "communist society" as described by Karl Marx.

[9]On 5 June 2007, Keen released his first book The Cult of the Amateur, published by Doubleday Currency,[10] and gave a talk at Google the same day.

[12] Pointing to examples like being able to gather teams together, travel to dangerous locations (sometimes spending years in the region) and having skilled and experienced editors oversee the process,[10] Keen forecasts that if the current Web 2.0 mentality—where content is either given away or stolen—continues, in 25 years[specify] there will not exist a professional music business, newspaper industry or publishing business and challenges his audience to question whether they value these or not.

In the book Digital Vertigo, Keen argues that the "hypervisibility" promoted by social networks like Facebook and Twitter traps users into sacrificing vitally important parts of the human experience, like privacy and solitude.

Tim O'Reilly has said: "he was just pure and simple looking for an angle, to create some controversy to sell a book, I don't think there's any substance whatever to his rants.

[19] According to Keen, there are five key tools to addressing the negative effects caused by the Digital Revolution, including changes in regulation, competitive innovation, social responsibility, education, and worker and consumer choice.