Infamous Tech Industry Predictions and Quotations (fascinating article with tons of quotes)
https://www.techspot.com/article/754-tech-predictions-and-quotes/
snip
There definitely is a new kid on the block, but there is nothing that IBM has presented that would blow the industry away
Tandys Radio Shack division financial VP when asked about the IBM PC
[Business Week, August 24, 1981]
snip
What would I do? I'd shut it down and give the money back to the shareholders
Michael Dell, Chairman/CEO of Dell Computers said when asked what he would do if he was CEO of Apple
[Various news outlets, October 1997]
snip
There's no chance that the iPhone is going to get any significant market share. No chance.
Steve Ballmer, Microsoft CEO
[USA Today, April 2007]
snip
In five years we're going to sit around and laugh that we even had operating system wars; there's just going to be Linux. We're going to take over
Trae McCombs, site manager Linux.com
[Maximum Linux, October 1999]
tons more, hilariously bad predictions and some really good ones.