In a 1998 issue of BYTE magazine, Edmund DeJesus made the claim that "[Y2K] is a crisis without precedent in human history."
Robert Metcalfe (the inventor of Ethernet) wrote an article for Infoworld in December 1995 in which he predicted, "I predict the Internet will soon go spectacularly supernova and in 1996 catastrophically collapse."
Andrew Keen, one of the most prominent commentators on Internet culture during the Web 2.0 movement, thought that the economic crisis of 2008 would have a huge impact on how we use the Internet...
He thought that Knol, Google's Wikipedia competitor, would end up on top. Google shut down Knol back in April 2012.
He predicted that The Atlantic would overcome The Huffington Post, which is now the 15th largest site in the US according to Quantcast. The Atlantic is 234th.
Despite Google's dominance of the search market, Keen thought people would come to prefer Mahalo, the "human search engine," to Google because its results are more curated.
He also believed that Hulu would overcome YouTube because he thought people appreciate "professional" content over the level playing field on Google's video platform.
Raymond Kurzweil, Director of Engineering at Google and noted futurist, made a number of predictions about what technology would be like in 2009 in "The Age of Spiritual Machines," his book from 1999...
He thought that the majority of text created would be made with speech recognition software. While sending quick texts or making quick searches with Siri is relatively common, most of us still primarily rely on a keyboard of some kind.
He also thought that phones would already be auto-translating conversations for us. While Google Translate can be impressively effective, we're still a number of years away from being able to pick up the phone and have a seamless conversation with someone who speaks another language.
In a now-famous Newsweek op-ed in 1995, astronomist Clifford Stoll made a number of predictions that couldn't be more wrong...
Like: "The truth in no online database will replace your daily newspaper, no CD-ROM can take the place of a competent teacher and no computer network will change the way government works."
Just think: there are millions of people who read The New York Times online but have never read the physical paper.
And: "Nicholas Negroponte, director of the MIT Media Lab, predicts that we’ll soon buy books and newspapers straight over the Internet. Uh, sure."
Never bet against technology that's more convenient than what's already available.
And then: "We’re promised instant catalog shopping–just point and click for great deals. We’ll order airline tickets over the network, make restaurant reservations and negotiate sales contracts. Stores will become obsolete. So how come my local mall does more business in an afternoon than the entire Internet handles in a month?"
How many shops at local malls have been put out of business because of Amazon's existence?