Needless to say, even the most accurate prognosticator is likely to be somewhat uncomfortable with his predictions a decade down the line, but I'm sure that Bill Gates is pretty proud of how often he was right in The Road Ahead, his book about The Internet. One has to recall that the Web was in its infancy when this book came out in 1995. Heck, HTML wasn't around until 1992, and only started appearing in the U.S. in 1993, so this book was very forward-looking for its time (I'd like to note that I created the old Eschaton Books web site in April of 1996, so I wasn't too far behind the curve, just way less well-funded!).
One thing that reading this book has done for me is to put some of the news stories of the past decade into perspective ... remember the big stink about Gates wanting to put a whole network of satellites in orbit? In the book he talks about a plan to put up 1,000 low-orbit satellites to provide wireless connectivity anywhere on the planet (a plan that got scuttled in the post-Columbia slow-down, but could well be revived given the new "commercial" space options). The press reported it like it was some form of megalomania, but he makes a very good case for it in the book. There are a number of similar examples of "oh, so that's what was going on!" revelations, but this is the one that comes first to mind.
If anything, Gates paints "too rosy" a picture of the "the future" ... one thing he totally missed was the "pirate culture" and how pervasive it would be. He talks about piracy, but only in the context of software licensing, he obviously didn't foresee how colleges would make high-speed connections available to their students, and how these students would set up file-sharing systems to illegally distribute copyrighted material, and how the Music (and, later, Movie) Industry would respond to the culture of Intellectual Property Theft that would emerge from that file-sharing. Gates' version saw the Music Industry working out a sane "personal license" system where people would buy, for a quarter or so, "personal use rights" to particular tracks ... of course, the "horse was out of the barn" before the Music Industry took the Web seriously, and so the story of "entertainment" on the Web has been more of a prolonged court battle than anything else.
Another place where Gates' vision diverges from what's happened (so far) is in the level of "interconnectivity" ... as anybody who has used Windows since 3.1 knows, at every step Microsoft has tried to make the "computer experience" one big unified thing, attempting to blur the lines between text, spreadsheet, database, graphics, video, Web, etc. ... this is very much part of his "vision", where individual computers are just "access points" to a bigger, more intertwined, "Information Highway" ... and is something to which I believe there is a a lot of resistance. He does, however, describe in eerie accuracy the new generation of "phones" that have full use of computer functions like MS Office (and GPS tracking) in what he describes as "Wallet PCs" ... however, these have not quite become the "Big Brother" tool (keeping all one's personal data, one's "music licenses", one's credit card or PayPal-esque info, etc.) that he seems to be heading for.
Would I recommend The Road Ahead, especially at this point? Maybe ... I mean, I've been involved with developing Web sites for a decade, so I've sort of watched as this stuff has played out, and it's interesting to compare my recall to what Gates was forecasting ... however, for the "uninvolved reader" it might sound a bit like the typical "oooh, we'll have flying cars by 1979" sort of "futurism", with many "reality paths" verging off (for whatever reason) from what Gates was guessing back in 1995. The good news is that if you are interested in reading this, it's available for cheap from the Amazon new/used vendors, with "like new" copies going for as little as 1¢ (plus $3.49 shipping, of course), and copies that still have the CD for as low as 25¢, and "new" copies starting at a buck ... such a deal!