Booted!

Yahoo Messenger illustrates the defunct company’s uncanny ability to turn gold into shit.

Published in

The Startup

9 min readMay 21, 2018

In 2016, Yahoo Inc. finally came to terms with the sobering truth: they were the Nickelback of tech. An irrelevant brand catering to irrelevant people. And just as Nickelback fans ultimately abandon them for the Foo Fighters, most of Yahoo’s users have slowly osmosed over to Google. Hand in hand with this revelation came their humiliating sale to Verizon for $4.5 billion.

Spectacular downfalls are bait and fodder for know-it-all pundits who put forth their personal theories in a bid for credibility, or at least notability, in the same way Perez Hilton rose to fame milking Britney Spears’s own downfall. Yahoo has been no exception. Internet pundits all think they know the precise moment that Yahoo went from being the zeitgeist of the ZomboCom era to the new Blockbuster Video.

Inevitably, blame will usually be laid at the feet of some embarrassing strategic blunder. Perhaps it was the company’s early obsession with being a production company that caused them to pass on the opportunity to buy Google for $1 million, or to go ahead and buy Broadcast.com (Broadcast dot who??) for nearly $6 billion.

Perhaps it was hiring known Hollywood stooge Terry Semel, who lost Google a second time, and then proceeded to lose Facebook and DoubleClick, and finally cost Yahoo a (remotely) dignified exit by turning down a $44 billion buyout offer from Microsoft, right before the global economy pulled its own Yahoo.

Perhaps it when Messiah — I mean Marissa — Mayer, cracked down on remote workers, or when she epically bungled a massive round of layoffs with secrecy and lugubrious slowness.

Hell, maybe it was the choice of that beveled trainwreck of a logo over a much more cheerful alternative:

Unfortunately all of these “Great Man” theories of cyber history ignore the inconvenient fact that no acquisition Yahoo made would have saved them, because everything Yahoo touches turns to crap. Yes. Crap.

They ruined GeoCities.

They ruined Delicious.

They ruined Flickr.

They ruined Overture.

They ruined Tumblr.

And if that’s how they treated other people’s stuff, imagine what they did to their own creations. Better yet, I’ll show you what they did.

Getting the boot

Yahoo Messenger is an illustrative case study. Messenger was an IM app much like AOL Instant Messenger and MSN Instant Messenger. It had the same basic features as its peers, and one significant advantage: it had built-in chat rooms.

With private messaging, a common area to chat with and meet new people, and personal profiles, Yahoo had a sort of Web 1.0 social network in the early 2000s. Any other company might have parlayed this into a cornerstone of their success, but Yahoo, a languid “media company” run by suits and overflowing with what Paul Graham bluntly calls “bad programmers”, ran Yahoo Messenger and Chat into the ground.

There can be no better illustration of Yahoo’s bad programmers at work than the existence of the once infamous chat booters.

What is a chat booter? This is a chat booter:

The above carnage is what an unlucky Yahoo Messenger or Chat user would see when an internet miscreant — usually an unemployed, involuntarily celibate 37 year old in his parents’ basement — decided to “boot” them.

Here is a video of someone being booted, to give you the full effect:

But what are they?

Chat booters are a form of junkware that exploit the many holes in Yahoo Messenger’s design to barrage the recipient with a Zerg rush of garbage data until their Yahoo client freezes up and shuts down. A disgruntled chatter could easily find one of these programs and torment other users to their heart’s content.

The holes were so well known and easy to exploit that chat booters were prolific and diverse, boasting all sorts of features for the discriminating troll. Here are just a few examples of booters out there.

War of Boot

Tap Out

C++ Error

Exploit Drop

No matter what they looked like, though, they all did the same thing: crashed Yahoo. Once a booter was set loose on your screen name, your Messenger would crash and maybe even your computer. The booter would run for quite some time, meaning that, as soon as the user restarted Messenger, they would be barraged yet again, fully shut out from their account and conversations. Blocking the offending chat user would do nothing because booters fabricated screen names.

While Yahoo sat with a collective thumb up its ass, third-party developers created Yahoo Messenger clients, such as YahElite, YMLite, and YTunnel, which were harder to boot. Yahoo didn’t even bother to copy them, which basically any other tech company would have done. In any case, the protocol for Yahoo Chat was so sloppy that even those third-party hacks could not fully do away with booting.

The only true defense for beleaguered users was to close off the ability for non-contacts to message them, obviating the proto-social-networking nature of Yahoo chat rooms. Once users had thus closed themselves off, any hope of Yahoo becoming a social media hub was vaporized. The chat rooms themselves languished, overrun by exurban scene trash typing in 48 point text, spam bots, and sex predators. The latter became such a problem that the hapless Yahoo gave up on user-created chat rooms completely.

By 2012, Yahoo Chat was dead, and, in 2016, all desktop versions of Yahoo Messenger were discontinued. Still clinging desperately to existence are mobile versions that sit alongside 100 other, better mobile chat apps, and it’s only a matter of time before they themselves disappear.

Deja hoo

The story of Yahoo Messenger was not a unique one in Yahoo’s sordid history. Flickr was equally ahead of its time in social media, but once it was acquired, Yahoo forced their users to obtain Yahoo accounts and did precisely nothing to actually benefit the product. After the arrival of smartphones, they prevented Flickr from creating their own app but didn’t create one of their own till years later, and what they did create was so bad as to chase away the remaining users. Today people use Instagram.

Then there was Delicious. Del.icio.us, as it was once known, was a site where users could publicly bookmark pages they liked, and you could see which pages had the most bookmarks. This form of human-curated content was like a Web 2.0 version of what Yahoo originally did, so it made for a logical acquisition. But, predictably, Yahoo worked their brown magic on it: instead of replacing Yahoo Bookmarks with Delicious, they kept the two products side-by-side and let the latter wither and die while Reddit and Twitter (and Digg, and Pinterest) took its place.

The last and perhaps most acrimonious of Yahoo’s monumental fuck-ups is Tumblr. The 2013 acquisition was the brainchild of the can-do-no-wrong Marissa Mayer and promised to finally give Yahoo the social network it needed. Unlike Yahoo, Tumblr was wildly popular and culturally relevant, even a little dangerous with its adult content. It was an injection of young and hip into the company’s frankly embarrassing demographic. For her part, Mayer swore “not to screw it up”. Yahoo had finally found itself and joined the world of social, for real.

LOL. Just kidding.

Mayer kept her “hands off” promise for about a year before Yahooing the hell out of Tumblr. First she forced the oil-and-water Yahoo and Tumblr sales teams to work together selling crappy top-down content for a neutered version of Tumblr referred to as “digital magazines”. Then she imposed a completely arbitrary $100 million annual sales goal because reasons, and hired a numbers-driven Amazon executive to enforce the nonsense goal while humiliating Tumblr’s founder, David Karp, by putting an ad-biz goon in charge of him. Then, of course, there was that whole porn issue, an already daunting legal and marketing problem to which the plodding Yahoo was not equal.

Mayer’s depredations chased off Tumblr’s homegrown leadership and talent leaving more Yahoo schmucks in charge of the gutted acquisition. The company failed to hit the made-up $100 million goal in any year, and Tumblr’s stock dropped by a quarter of its value. Meanwhile, Tumblr hemorrhaged users and cultural currency to newer startups like Medium and Giphy. The mass exodus left the once happening Tumblr as little more than an insular echo chamber of fragile twentysomething social justice warriors, and as much a punchline in cyberculture as MySpace once was.

Bred to suck. Born to die.

Yahoo’s cycle of acquisition and destruction of once-promising products is as predictable as an episode of Scooby Doo. This much we know. But why? We can talk about the lousy programmers who couldn’t code their way out of a paper bag, but who hired them? We can debate endlessly about which CEO was the one to push Yahoo off a cliff, but why did the company consistently attract such duds in the first place? How could a company as successful as Yahoo once was, one of the first huge brand names on the internet, be so cursed?

The answer might be as simple as this: Yahoo was never supposed to succeed in the first place.

Yahoo wandered blindly into the right place at the right time in the 1990s by creating an electronic Yellow Pages. Their zany escapade lasted until the Web became too big to fit in a phonebook, at which point they immediately started flailing helplessly while their fortune disintegrated. Yahoo was the Powerball winner who blew their fortune on drugs, hookers, and a surplus Cambodian Air Force MiG-21, and ended up so deep in the hole, they were reduced to giving rimjobs for crack money.

Whether it was pushing Swiss-cheeseware and calling it a product, ruining well-loved web brands, or inflicting the Kardashians upon anyone foolish enough to visit their homepage, Yahoo was always making a mess. Perhaps it really was just in their DNA.

Yahoo has joined Gawker in the ranks of well-deserved undoings. If we’re lucky, Upworthy will be next to get booted!