One of the most important changes in the Web over the last ten years is that conversation's moved from private email, community email lists, and writer-owned blogs into various corrals and golden cages. If you were writing code in 2006, particularly "cutting edge" code like Rails apps (at the time), you remember how blogs were the new documentation, and all the dev community interaction took place in IRC or on email lists. I always felt embarassed that my blog lived on Blogspot, but the point's moot today. For new projects forming now, the information all sits on StackOverflow, GitHub, or Twitter -- or in personally-published ebooks.
The Web we lost was a temporary autonomous zone, and like all temporary autonomous zones, it provided an illusion of utopian anarchy wrapped within a coccoon of privilege.
Speaking of privilege-induced misperceptions, the tech press seems determined to prove it is not only too arcane and insular to provide any use whatsoever to non-techies, but also that it is too firmly and deeply rammed up corporate America's anus to provide any use whatsoever to techies either. Consider 2013 was a lost year for tech:
All in, 2013 was an embarrassment for the entire tech industry and the engine that powers it—Silicon Valley... Not a single breakthrough product was unveiled... 2013 was a great big dud for technology as a whole.
Om Malik picked up the horseshit baton and enthusiastically carried it down the field, "arguing" against that "lost year" blog post with a defense of 2013 as a year in technology which did not once mention either Bitcoin or Edward Snowden.
The biggest 2013 stories in tech were economic and political stories straight out of the pages of 1980s cyberpunk novels, straight out of the archives of 1990s cypherpunk listservs, and straight off the list of top headlines for the year in general. So-called tech journalists didn't even notice.
At the end of 2012, Anil Dash wrote The Web We Lost. By the end of 2013, we all knew about the Web we had built instead: essentially, it's J. Edgar Hoover as a service. It doesn't really matter how much money your web startup is or isn't making today; wait for a few iterations of Moore's Law and you'll find that your user data couldn't be more valuable if it consisted entirely of Bitcoin hashes. Of course, you'll also find that the NSA's taken control of it, which is the savviest land grab in human history.
2013 was the year Occupy Wall Street got serious about encrypting their email, while Wall Street got serious about cryptocurrencies. It was the year we all discovered that the cypherpunks had underestimated how important encryption would become.
Of course, I can't expect every hacker to remember the cypherpunks, or the Web we lost. Many, many hackers know absolutely nothing about either subject. The tech industry thrives on young new recruits, whether because their inexperience makes them easier to exploit, or because software is eating the world and, in the process, making every new generation of programmers more populous than the last.
(This ongoing demographic trend exerts two obvious, inevitable repercussions: it means each subsequent generation of programmers gets less weird, on average, and stupider, on average. The good news is that the growing-stupider is happening slowly, but the bad news is that the de-weird-ification is happening quickly. This explains how online culture moved from profoundly weird to pervasively frivolous. Where we once had Eris, we now have the Flying Spaghetti Monster. September becomes ever more Eternal with every passing moment.)
But whether you remember the past or are doomed to repeat it, today's walled gardens all share one huge, fundamental, fatal flaw: software is eating the world. It doesn't care what's on that world; it's after the whole katamari. Friendster fell to Myspace; Myspace lost to Facebook; and the NSA might have its hooks deep into Facebook, but those hooks won't make anything immortal. If there's one lesson we should learn from the past, it's this: Software Will Eat Itself.