Content is king, and sites with content richer than plaintext have done substantially better. Advertising has done well, and long-term subscription models continue to drive down user counts. The line about "attract attention, not convey information" was a prescient look at a world of shitty, flashing banner ads. He missed subscriptions for premium features, but it's a subtle difference.
On the other hand, ads still cripple the speed of page loads - smart advertising has added weight as fast as internet speeds have improved. Per-use transaction fees still haven't caught on (except in freemium games) because they encourage users to not consume content, and because no one trusts a central authority to set them up. Ultimately, ads are the only effective small-charge technique anyone has found.
He was spot-on with the problems the web faces, but wrong in thinking they'd be solved by now.
In retrospect, The Road Ahead probably had a more profound effect on me than I realized at the time. There's a great quote from the book which sums up why I took hold to computers and software more than many of the other creative and engineering related endeavors I had at the time:
"Computers are great because when you're working with them you get immediate results that let you know if your program works. It's feedback you don't get from many other things."
No, you get that feedback from playing music and singing.
In many ways, it seems like Microsoft's late-90's obsession with content didn't really pan out. Sure, MSNBC is still around but sidewalk.com long since evaporated. It doesn't seem like MSFT really became a profitable media company.
But look at how many multi-billion dollar "unicorns" are messaging companies.
Talking about current valuations of relatively young companies is odd when comparing to Microsoft's history. The scale of things means that what works for one doesn't necessarily work for the other.
Still is. And will always be.
The annoyance of ads will always expand to fill any improvements in throughput achieved by technology.
Seriously though, why did it take so long for adblocker to be invented?
I remember setting up some kind of http-proxy with local cache an ad filters in the late 90s, early 00s -- possibly squid with a plugin -- probably on Slackware. Persistent local cache of static resources helped a lot with loading sites (which doesn't really make any sense, considering browsers already had a local cache). Ad-blocking was simple -- just replacing banner.gif-s with a blank gif image or something along those lines. But it worked, and preserved the layout of the page.
Overall he's still right--content is king. But I predict that in the future the internet is going to be dominated by user generated content and websites that can effectively show us what we want to see--websites that can refine the ever-growing amounts of information we have at our fingertips.
Incredible how far we've come from "put up with turning on a computer."
"But within a year the mechanisms will be in place that allow content providers to charge just a cent or a few cents for information. If you decide to visit a page that costs a nickel, you won't be writing a check or getting a bill in the mail for a nickel. You'll just click on what you want, knowing you'll be charged a nickel on an aggregated basis."
I can't decide if this sort of micropayment-driven internet would be heaven or hell.
There are effectively two classes of internet citizens: those who block ads, and those who do not. Users like myself free ride off the eyeballs of this second class.
Imagine if ad-blockers were included in internet browsers by default. It would cripple the economics of the internet. (Is this the explicit reason for Chrome? Because it look like a great defensive maneuver.)
I think this is generally true, but less true today than it may have been a few years ago.
What percentage of interactions on social networks involve sharing or referencing preexisting content of some sort? Movie trailers, articles, songs, Buzzfeed lists, surveys, memes, and so forth? Many of these forms of content have been created by one type of media company or another.
Content is king, but what Gates could have never guessed was what type of content.
Look how far we've come.
For music and writing, distribution is king.