In more ways than not, “Web 2.0″ was the late 2000′s equivalent of the 1990′s Internet craze. Beyond a handful of undeniable success stories (Facebook and YouTube come to mind) lies a vast wasteland of promising yet failed ventures whose only hope was being part of the Web 2.0 movement. It’s not at all unlike the late 1990′s, which produced a few enduring champions (namely Google) but relegated ill-prepared companies like Lycos and Webvan to the tech graveyard.

Here are some of the biggest Web 2.0 flops to date:


The latest addition to the TechCrunch Deadpool, online money management service/community Wesabe ultimately found itself unable to match the success of rival Not that Wesabe didn’t have its moments along the way. Prior to announcing its demise on June 30, Wesabe had enjoyed considerable press coverage, garnered a large user base and raised nearly $5 million in venture capital since 2005. The problem seemed to relate not just to Wesabe or its management, but also to how over-crowded the online money management space became.

JJ Hornblass of opines that websites like Wesabe “popped up like fungus in a marsh”, citing Revolution Money,, BillMonk, PayPal, Buxfer, expensr, Cake Financial, Geezeo, Thrive, Jwaala, PearBudget, GreenSherpa as other examples. Hornblass further remarked that Wesabe “was a bad bet for its investors” because it never obtained nearly enough users (tens of millions) to “reach critical mass” in that sector. In a farewell note on its website, Wesabe confessed to relying on cash from its own developers to stay afloat.


Eventvue, a Web 2.0 startup focused on helping people network with one another at various events, regretfully announced that they were closing up shop in February 2010. It was an interesting ride for the three-year old company, who was kind (and honest) enough to reveal its fatal flaws in a lengthy post-mortem. Among Eventvue’s biggest mistakes were:

  • Tried to build a sales effort too early, with too weak of a product after initial financing
  • Waited too long to address the “nice to have” problem
  • Went after enterprise sales model with a non-recurring, small price
  • Didn’t make Eventvue self-serve to let anyone come and get it

The company also alluded to a number of “cultural” mistakes, such as:

  • Didn’t focus on learning & failing fast until it was too late
  • Didn’t care/focus enough about discovering how to market Eventvue
  • Made compromises in early hiring decisions – choose expediency over talent/competency


While Squidoo is technically still in existence, the near-unanimous verdict within the tech community is that it is a Web 2.0 bust. The idea seemed reasonable enough:

“…allow anyone to build a single page, called a lens, on a topic that he or she is passionate about. The person building the lens, the “lensmaster”, gets recognition as an expert in his or her area of expertise, and cash. Squidoo shares a percentage of profits with its authors.”

Despite being founded by marketing icon Seth Godin, there were doubts about the community’s viability from the start. As early as 2006, Michael Arrington of TechCrunch predicted that Squidoo would be Seth Godin’s “purple albatross.” That prediction appears to have materialized. remarks that while this would have had great potential five years ago, “there is no reason for anyone to create a page and fill it with links to other places simply to look as though they are an expert in that category.” Further insight is offered in the 2009 post Squidoo’s Greatest Failure.


Some failed Web 2.0 startups were simply ahead of their time. This appears to be the case with Meetro, the first attempt at a location-based instant messenger service. While Meetro began life in 2005 with serious fanfare (including a Slashdot rumor about a potential Google buyout), the company was unable to sustain its early momentum. As explains in a rundown of Web 2.0 failures, there were two main stumbling blocks.

First, Meetro “was never 100%” in determining the correct location of the user. Therefore, Meetro was unable to inform the user’s contacts of exactly where the user was. The other issue is that Meetro’s founder, Paul Gragiel, confessed that “the service simply wasn’t that interesting.” Perhaps today, when companies like FourSquare are thriving, would have been a more hospitable business climate for Meetro.

ProtectMyPhotos fell at the hands of the overcrowded photo storage market and failing to stand out. Founded in October 2006, the service essentially piggybacked on what every similar site at the time was offering: letting users upload photos online as a backup to save hard drive space or protect against catastrophic data loss. While this was (and is) a valuable service, there was nothing to meaningfully set ProtectMyPhotos apart from more robust services like Google’s Picaso or Flickr, which went on to incorporate social elements and networking.

The uncompetitive website ultimately shut down in December, 2007.


Storytlr did not become a flop without a fight. The service was built upon lifestreaming, the concept of creating a sort of “electronic diary” of your life on the web. Founded by two Netherlands entrepreneurs in 2008, Storytlr generated substantial interest early on. (TechCrunch shares a video of one Storytlr founder pitching the concept to Google’s Sergey Brin.) Unfortunately, the founders determined in October 2009 that it simply could not be turned into a viable, long-term business.

Storytlr is survived in the lifestreaming space by startups like,, or Sweetcron.

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