The common criticism is his prediction about the internet:
https://web.archive.org/web/19980610100009/http://www.redher...
> By 2005 or so, it will become clear that the Internet's impact on the economy has been no greater than the fax machine's.
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I wasn't aware that he put a "2005" deadline in his prediction. Taking this into account, he probably wasn't wrong actually, at least in terms of net impact: in 2005 most of the moderate positive economic impact of the internet would have been offset by the significant negative economic impact of the dot com bubble and subsequent crash.
I don't read it as a deadline. It's the latest date we will all understand what an economic flop the Internet turned out to be.
Not the latest date at which the Internet was still on par with the fax machine.