Kozmo.com (1998-2001)
What it was: An online retailer, founded by Joseph Park and Yong Kang and serving 11 metropolitan areas at its height, that used bicycle messengers to deliver snacks, DVDs, magazines, electronics products, and other stuff in an hour or less.

Why its loss was tragic: Instant gratification is the American way, and Kozmo delivered that in spades: It was sort of a 7-Eleven you didn’t need to go to. (I reviewed the service back in 2000 for PC World,  found that it largely delivered on its wacky promise, and said I hoped it was an early example of where Web shopping was going.)

On the other hand: Kozmo’s offerings were limited and kind of random, and it apparently couldn’t figure out how to stock anything but stale old issues of magazines. And had it succeeded, the nation’s geeks would have gotten their Ben & Jerry’s and Cool Ranch Doritos without even having to burn a few calories by venturing out to buy them.

Where it went: Like many other dot-com superstars of the mid-to-late 1990s, the only thing wrong with Kozmo was that its business model didn’t make any sense. It spent $250 million to build warehouses and hire armies of employees, yet it specialized in inexpensive items which it sold for about the same price you’d pay in a convenience store, and it didn’t charge a delivery fee. After layoffs, cutbacks, and a fruitless search for a buyer, it collapsed in 2001.

Adequate substitutes: MaxDelivery, founded by Kozmo’s former CTO, offers a Kozmo-like service that I’d use if I lived in lower Manhattan. And Amazon.com–which invested $50 million in Kozmo back in the day–quietly offers same-day delivery in six metropolitan areas. Not everything Amazon sells is available, but the selection is still closer to Amazonian than Kozmo’s skimpy offerings. On the other hand, it’s fairly pricey at $14.50 to $19 a shipment, plus per-item charges.

Modern Humorist (2000-2003)
What it was: A humor site made up mostly of satire on topical matters–this was before there was much audio or video on the Web–that felt a little like a contemporary, Web-based National Lampoon.

Why its loss was tragic: Lots of folks have tried to do comedy on the Web; few have succeeded in tickling anyone’s ribs for very long. But Modern Humorist was pretty funny, pretty consistently. And even though some of its targets feel like period pieces–Jerry Springer, Napster, the 2000 election— they hold up surprisingly well. Plus, its banana-peel man logo ranks among the best mascots a Web site ever had.

On the other hand: Its proprietors also operated a custom-publishing operation that produced a site for Microsoft featuring Clippy, Microsoft Office’s much-loathed talking paperclip. Nothing funny about that.

Where it went: Nowhere! The site’s content is no longer all that modern, since it hasn’t been updated in more than five years. But it’s all still there, and it gets hundreds of thousands of visitors a month. I’m not sure if that’s funny odd or funny hah-hah, but I’m glad that MH is still with us, sort of.

Adequate substitutes: You can’t beat The Onion, of course. And College Humor is a funny, media-rich site with a Modern Humorist-like sensibility.

Think Secret (1998-2007)
What it was: An Apple rumors site founded by muckraker/Mac fanatic “Nick dePlume” (aka Nicholas Ciarelli) at the age of thirteen.

Why its loss was tragic: Think Secret’s record for accuracy was far from perfect, but it was better than most. And one scoop–revealing Apple’s plans for iLife ’05 and the Mac Mini a month before Macworld Expo 2005–was so dead-on that a rattled Apple sued dePlume, who was by then a Harvard student, in hopes of uncovering the leakers who tipped him off.

On the other hand: Like most Apple rumormongers, dePlume tended to sound equally sure of himself whether his scuttlebutt was eerily accurate or wildly off.

Where it went: In December 2007, Apple and dePlume settled their legal tussle out of court–and part of the agreement was that Think Secret would be shut down. The site was dePlume’s to do with as he wished, but it was hard for anyone outside of Cupertino to feel good about the events leading to its demise.

Adequate substitutes: MacRumors and Apple Insider both report on Apple-related rumors in the Think Secret tradion; both have managed to stay out of court to date.

Octopus (2000-2002)
What it was: One of several early Web services that let you grab chunks of Web content right off other sites–say, a block of sports news off of CNN’s home page–and then combine everything into one personalized home page that automatically updated itself as the information on the originating sites changed.

Why its loss was tragic: Octopus’s technology was ambitious and impressive, especially since it dated from an era before RSS and widgets formalized some of the concepts that Octopus implemented all by itself.

On the other hand: Impressive or not, the technology didn’t always work perfectly; you might grab content, plunk it into your Octopus page, and then discover that it didn’t function properly there.

Where it went: Like many not-so-many consumer startups, Octopus tried to reinvent itself into a service for large companies. I was later bought by Ask Jeeves, then it disappeared. Today’s Octopus.com has nothing to do with the defunct service–it is, appropriately, a site about octopi.

Adequate substitutes: iGoogle, NetVibes, and Pageflakes all do more or less what Octopus did, and the “Web Clips” feature in Apple’s Leopard OS is also closer in concept–it just took them a lot longer to figure out how to do it.

Suck (1995-2001)
What it was: An early “Webzine,” founded by Joey Anuff and Carl Steadman, that covered matters Internet-related and otherwise in an idiosyncratic, snarky fashion that was, at the time, unique–as was its daily publishing schedule, in an era in which most Web sites operated more like monthly magazines.

Why its loss was tragic: Mostly because Suck was a reliably good read–clever, cutting, and on-target. But it was also hugely influential. In tone and format, Suck was essentially an important blog that happened to exist prior to the invention of blogs. (See this article by Matt Sharkey for much, much more about Suck’s history and importance.)

On the other hand: I’m not sure if I can think of anything bad to say Suck, other than that it had its hits and it had its misses. Overall, though, its standard was uncommonly high.

Where it went: Suck changed corporate hands multiple times, and ended up part of an independent media company called Automatic; during the great Internet crash of 2001, it…crashed. In June of that year, Suck declared that it had “Gone Fishin’,” and new posting ceased. Ironically enough, it died just as the blog explosion was beginning. But its Web site remains online, which an archive of six years’ worth of content.

Adequate substitutes: I don’t think any one site is Suck’s heir apparent. But its alumni seem to be everywhere, and they’ve taken some of its attitude with them–notable examples include Ana Marie Cox, the former Wonkette, who now blogs for Time; and Owen Thomas, a Suck copy editor who now runs Silicon Valley gossip site Valleywag.

That’s my list. If you got this far, thank you–and please share your thoughts…

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