I have been blogging for over 10 years now, so I watched Six Apart form, rise and then fall from grace. I wouldn't classify it as having 'failed', but it certainly has not lived up to expectations or potential.In the early days of blogging, undoubtably the most popular self-host platform was Movable Type. At the time that Six Apart was incorporated and received its seed round of funding, Movable Type was well established, and the developers (Ben and Mena Trott) were popular and active members of the early nascent blogging community.Movable Type as an application got a lot right, including the interface and ease of installation, but it got three things wrong:It was written in Perl, which made administration and extensibility a pain. For designers it was a lot more complicated to create an MT theme than modern blogging themes such as with WordpressInstead of dynamically rendering the blog and posts, MT generated static HTML pages. This meant that every time you published a post, an HTML page for that post was generated, and every page that contained a link to it or the archive would also have to be re-generated. Once a blog reached a certain size, the time taken to generate these pages became very long. Even the smallest update to a post would trigger an update routine that would take (sometimes) minutes, and that would also often break mid-generation, resulting in a broken blog. The upside was that the web server was hosting static pages, making scalability easy, but the static file generation had far too many downsides.The licensing issue. This was an impetus for the mass-migration and overnight success of Wordpress. While you can download and read the source code of MT, the early versions were not open source. With the launch of MT 3.0, Six Apart modified the license for MT that restricted the non-free use (restrictions such as the number of blogs, commercial blogs required a paid license etc.). Pricing for a license ranged from $70 to $600. Because of the license change, many bloggers actively sought out an alternative, open source, blogging platform. Wordpress filled this gap, and a lot of bloggers switched over in the span of a few short days. While Six Apart eventually modified the license, and apologized to its users[1][2], it was too late, a lot of bloggers had already switched to Wordpress.Six Apart eventually released Movable Type as open source software, but at that point Wordpress had established itself as the new standard for self-host blogging. Wordpress exploded in popularity partly because it was so easy to build templates (PHP) and plugins (it contained an extensive hooks system).The licensing bungle coincided with the Google acquisition of Blogger - the first large corporate M&A deal in the space. Blogger was on a tear - they offered a free and easy to use blogging platform with the option for paid accounts. Under Google, the paid features became free features.In 2024 or '04 Six Apart launched Typepad - which was essentially a commercial hosted version of MT. It cost $5.95 a month (IIRC, it is now $14.95 a month for a standard account[3]). The disadvantages of Typepad over self-hosted Wordpress were:You couldn't use your own templates, and could only modify colors, number of columns etc. on the default Typepad template - which meant that a lot of Typepad blogs looked the same or similarThe initial release did not have support for a custom domain name (all blogs were at *.typepad.com or *.blogs.com)No support for custom pluginsTypepad did build a decent customer base, but a number of companies were offering hosted Wordpress which allowed more themes, customizations and plugins.In '05 Six Apart acquired Danga Interactive, the owners of LiveJournal. The LJ community didn't really gel with the Typepad community, and the two networks were kept separate. Live Journal also potentially competed with Typepad, since it offered paid accounts with greater features than typepad at a lower price[4]. At this point Six Apart had three products: LiveJournal, Typepad and Movable Type - along with a number of other sub-products that enabled mobile blogging, photo blogging etc.In '06 Six Apart created Vox - which was part blogging platform and part social network. Typepad was for broad web publishing, Vox was for publishing to your friends or immediate network. At this point Six Apart were now offering 4 products - with no real cohesion between them.Vox was generally well-received by bloggers, with GigaOM even proposing that Six Apart and Facebook should merge[5]. Six Apart also acquired Rojo, a semi-popular RSS reader, and were responsible for the development of a number of technologies that are at the core of blogging and publishing today (such as trackbacks, contributing to the early Atom protocol, etc.)During that time, a CEO was bought in[6] and the management team went through a number of iterations. A lot of the personalities that bloggers associated with the company, such as Ben and Mena and Anil Dash, are either in non-managerial roles or have left the company. blogs.com (a great domain name) was turned into a new product - a blog discovery tool. It helps users discover interesting blogs.More recently, Vox has been shut down, Live Journal has been sold off and Movable Type has been updated to rid of some of the disadvantages it had compared to Wordpress. The typepad.com domain is a top 200 website in the USA, but Movable Type probably isn't even in the top 5 blogging platforms. In 2024 Six Apart laid off 8% of their workforce (they had over 200 employees at the time), and it claimed that the combination of record quarterly revenue and the Live Journal sale should see them through until at least the end of 2024. It is thought that Six Apart profited near $20M on the Live Journal sale (acquired for ~$12 and sold for $32M)[6] (the same blog post lists over a dozen different Six Apart products)While Six Apart was restructuring, Wordpress parlayed their early success into a successful free hosted solution at Wordpress.com (a top 10 web domain). Wordpress is one of the largest AdSense recipients and the most popular self-hosted and hosted blogging platform in the world. Six Apart went from preparing for an IPO, to cleaning house in a bid to sell the company to a suitable bidder. The latest rumor is that a merger with VideoEgg (also backed by August Capital) is imminent. Now as for why Six Apart 'failed' (or more accurately, did not match expectations), I would summarize from my own observations:The failure to harness the early community around Movable Type by turning it into an open source product. A lot of potential contributors to the platform were turned off by the license terms. Wordpress played this well and built a very strong and sizable community around the product. Wordpress was an open source product first, and then a company second. Some of the biggest early supporters of Movable Type went on to become its most vocal critics.Hesitating on early strategy. They wanted commercial revenue on both Movable Type and Typepad, although there were better open source alternatives. They switched licensing and pricing around a number of times, which only disenfranchised their previously-enthusiastic user base.Failure to recognize trends. While Six Apart were responsible for developing a lot of underlying technology used in blogging, they completely missed other product opportunities. Typepad had mobile and other photo sharing, but that was soon taken over by Flickr. Vox almost stumbled onto the magic formula (personal sharing of photos, information) that Facebook nailed. Twitter stumbled onto short-messaging (or micro-blogging) while Six Apart missed that opportunity, even though a lot of Typepad blogs were setup to publish simple 1 or 2 line posts with images and video. Then there was the self-hosted blogging opportunity, which Wordpress took over. Six Apart could have taken any number of similar opportunities but failed to recognize any of them, and instead persisted with a paid, commercial blogging platform (along with the other aborted attempts).Focus on revenue over building a user base. Typepad was only ever free for the first 14 days, so while other products and social network were building up large user numbers by offering free products subsidized by advertising, Six Apart stuck to a commercial model that relied on licensing revenue. By forcing users to pay for the product, they stifled any network effects that Typepad could have experienced. They rectified this later with Vox, but the new separate product only confused potential new users.Lack of clear product focus. 4 or 5 main products, with an assortment of sub-products ranging from RSS readers to blog discovery and everything in between (including an ad network). If Movable Type was open source, and Typepad was a free blogging platform with social features, Six Apart would be unstoppable today.Conflicting pricing. With the license changes to MT, it turned out that the cheapest MT license ($69) cost more than a full year of Typepad. Further, Live Journal had free accounts, with paid accounts that cost less than Typepad but arguably offering more features (and more storage, bandwidth). Further - Vox was free, which only further complicated the pricing structure across all the products. MT had an upper price bracket of $599 for a license, while Wordpress and Drupal were free.Understanding your users. After acquiring Live Journal, Six Apart introduced new rules, deleted some groups and did a number of things that had the LJ community protesting against the new owners and deleting their accounts. It was apparent that Six Apart did not understand the community that they had acquired[7]Downtime. Typepad, despite being a paid service, experienced a lot of downtime, especially in the early days. I recall a number of blogs canceling their Typepad accounts around this time.[8] There was one period where some blogs were down for days[9]Poor PR and community relations. Six Apart was known for aggressively countering any negative talk about the company in blog comments[10]. Not dealing with competitors very well[11] Anil Dash did an excellent job as an ambassador of the company, but there were incidents such as Mena's 'asshole' remark that riled up the LeWeb 2024 audience[12][13]. If you read some of the blog posts and comments from developers, you will find that there was outright sheer anger at Six Apart for both the MT licensing debacle, and for the way they attacked Wordpress. This caused many developers (and the people who read and followed their blogs) to abandon the company and actively pursuit alternatives. Wordpress only succeeded because it filled a void that Six Apart created. If Six Apart handled the community better, I don't doubt that they would have been a lot more successful today.All is not lost, and there is a chance that Six Apart can be resurrected. The plan should involve opening up TypePad to free users, building out a social platform that can be accessed from self-hosted or hosted MovableType, and building out the platform so that corporations can self-host their own intranet social networks (this space is crowded, but none of the solutions atm are good). The new platform could also support a self-hosted micro-blogging service and social network (like a distributed Facebook or Twitter).IMO (and a warning, that a lot of what I have written in this answer is my own opinion) Six Apart has been one of the most interesting case studies of a web startup of the past decade. We will probably not find out a lot of what went on internally until the company eventually achieves an exit or shuts down (I doubt it will shut down, it seems relatively healthy revenue-wise today*) - but a business biography by either one of the founders or somebody else involved in the company would definitely be interesting reading.* Healthy in that a blog post from last year mentioned that with current staffing levels, they have runway until the end of 2024 (from revenue and the sale of LJ). It is assumed that if all else fails, Six Apart could trim their head count and grind out profitability from Typepad recurring revenue. According to Crunchbase, Six Apart currently has 150 employees).[1] http://www.sixapart.com/blog/200...[2] http://news.netcraft.com/archive...[3] http://www.sixapart.com/blog/men...[4] http://www.typepad.com/pricing/[5] http://gigaom.com/2006/11/01/six...[6] http://www.sixapart.com/blog/200...[7] http://news.cnet.com/Mass-deleti...[8] http://www.sixapart.com/blog/200...[9] http://www.sixapart.com/blog/200...[10] http://www.krotscheck.net/2008/0...[11] http://techcrunch.com/2008/03/11...[12] http://www.sixapart.com/blog/200...[13] http://benmetcalfe.com/blog/2005...