When Linux was a Struggling Challenger 💡 Key Point This is a 2026 restoration of my (Dan Shearer’s) 1998-2001 guide, preserved at archive.org ↗. Links have been updated to point to the archives where possible. In 1999 I joined my first startup, Linuxcare in San Francisco. The Linuxcare story is a quintessential United States dot-com bubble narrative, featuring a famous venture capital fund, massive growth, a failed IPO, and a fancy new ex-IBM CEO resigning under a cloud. Founded in 1998, Linuxcare aimed to be the “0800 number for Linux”. So close!
As Samba co-founder I had experience migrating corporates away from Microsoft servers, and brought my how-to with me to Linuxcare. Microsoft was extremely sensitive to documents like this, and downright allergic to the word ‘replace’. I found out years later this article was targeted for disinformation in key Microsoft accounts. This was a battle of narratives as well as monopolistic behaviour and technical facts.
More than a quarter of a century later, the technical content has aged fairly well. Quite a lot of the migration solutions were easier than they would be now, because quality of the Microsoft/Windows solutions was so poor. Many of the monopolistic facts remain much the same, which is slightly depressing. But some things were unimaginable in 1999:
Samba both succeeded and failed but Samba (or something like it) may have another chance The EU is serious about alternatives Exciting times! But not for Linuxcare, which had spectacular human failures and quietly collapsed from 300 staff to 3 within a couple of years.
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