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Six Apart sure did mess up the opportunity they had. They went from IPO track to forced merger in the space of a few years.

See this answer on Quora: "How Did Six Apart Screw Up (the complete story)":

http://www.quora.com/How-did-Six-Apart-screw-up-The-Complete...

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is it possible that this is another case of lifestyle entrepreneurs who enjoyed the product but never really wanted to get caught up in the SV/ VC model? and without them there to carry on the vision, and thereby no real product strategy, creating this mismatch of four synergistic products, it was always to struggle?

I think this is definitley the case. The company started when Ben Trott developed a web publishing engine for his wife, Mena, who wanted to use it to update her sewing group. Similar to eBay, except unlike eBay Six Apart didn't bring in big-gun management until later on (and they weren't as good as say, Meg Whitman).

Most of the poor decisions were made at that time, Wordpress took the lead and then didn't look back from there.

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