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Novell & UNIX
In 1991, if you were running a personal computer network in your business or enterprise, there was a good chance it was running on Novell's NetWare, which was the predominant server-based network operating system at the time.
Released in both 16-bit and 32-bit versions for the 286 and 386 Intel processors, 1990's era NetWare ran on a proprietary protocol called IPX, which ran on on Local Area Networks using Ethernet, Arcnet or IBM Token-Ring topologies. NetWare was known for its excellent network performance, server reliability, fault tolerance and OS stability, as well as its relatively easy administration, which helped it maintain its market position for many years.
Novell had several competitors in the space, such as IBM OS/2 LAN Manager and Banyan-Vines, but none of them were ever as popular as the NetWare stack. However, with the release of Microsoft's Windows for Workgroups 3.1 in 1992 and Windows NT operating system in the summer of 1993, companies quickly began to shift to a fully integrated, single-vendor Client and Server OS solution for their networks.
To maintain relevancy in the network operating system space, in 1991 Novell entered a partnership with AT&T's Bell Unix Systems Laboratories (AT&T) to produce a "SuperNOS", that would combine the network protocols of Netware with the power of the UNIX operating system. The partnership, called Univel, resulted in USL being purchased by Novell in 1993 and the release of the UnixWare operating system.
UnixWare at Novell was a complete dud. In 1995, Novell sold the operating system to SCO. However, the exact terms of the transaction were not fully determined until 2011, when it was ruled by the US Court of Appeals for the tenth circuit that despite SCO's ownership of the UnixWare operating system itself, the UNIX copyrights still belonged to Novell.
In addition to failed UnixWare partnership, in June of 1994, Novell looked to enter the office productivity software space by purchasing WordPerfect corporation. That marriage lasted a whole two years, and the WordPerfect company's assets were sold off to Corel in January of 1996.
The legacy Novell NetWare operating system continued to be developed until 2003, where it was superseded by Open Enterprise Server (OES) a network operating system which runs on top of Linux.
In November of 2010, Novell was acquired by Attachmate, for $1 Billion.
MySpace & News Corp.
Founded in 2003, Myspace was once the most popular social networking web site in the world, and in June of 2006, the company surpassed even Google as the most visited website in the United States. In August of 2006, the site had reached over 100 million account activations.
In 2005, the company was purchased my Rupert Murdoch's News Corporation for $580M. When the company was at its peak in 2007, Myspace had a market capitalization of about $12B.
In 2008, the company's fortunes began to go into a steep decline. Rather than improving their social networking experience the company chose to go with a "portal-style" strategy for building its audience around music and entertainment instead. Additional modifications to the site in the hopes of increasing the company's advertisement revenue also made it unwieldy and slow to use.
To make matters worse, the company's main rival, Facebook, was eclipsing it in traffic with its clean and efficient site design, increased number of users and was building a platform where 3rd-party developers could plug into an API to build new applications for it. By contrast, Myspace was doing all of its development in-house.
In June 29, 2011, Myspace was sold to Specific Media and pop star Justin Timberlake for approximately $35 million, a far cry from the $12B valuation it had only four years previous.
Google & Motorola
In 2012, Google purchased the handset/tablet division of Motorola, for $12.5B. Over the next two years, Motorola essentially floundered with its product releases and was one of the worst offenders in lagging Android OS updates of all the Android handset OEMs.
The Google and Motorola Mobility merger failed on so many levels that it's hard to quantify the extent of the incompetence that surrounds it.
Not only did Motorola consistently fail to innovate after being acquired by Google, but during its time under Google's ownership, the company released a number of Android handsets of questionable quality, stability and performance, that have been mired by shovelware and awful user interface overlays.
The company has also reneged on its promises to upgrade an entire generation of dual-core handsets released in late 2011 to Ice Cream Sandwich, effectively leaving many of its existing customers in the lurch.
To add insult to injury Google sold much of Motorola's manufacturing capability to Flextronics, which begged the question of what the Silicon Valley search giant really intended to do with Motorola's engineering and future handset and tablet plans, especially since Google partnered more and more with companies like Samsung, Asus and LG for its "Nexus" line of products.
Google did eventually try to integrate Motorola into the company, and release a flagship handset, the Moto X, which had the distinction of being manufactured in the United States and having many different unique customizable designs that could be ordered to personalize the look of the product.
Unfortunately, the Moto X was not a big hit in the marketplace. Google recently decided to cut its losses with its less than 2-year romance with the company, selling it for $2.91B to Lenovo.
Google is retaining much of the patents from Motorola and also the company's research facility, so it isn't a total loss for them. Still, this is a fling that will almost certainly go down as one of the search giant's biggest failures.