For me it was Windows 3.1 -> Specialized Stumpjumper M2 -> Linux.
Oh yes! I forgot to include the Specialized bike in there (not a hardtail, though).
In my case, it was actually a critical part of the upgrade path. I sold my only computer to finance the bike. The next time I got a computer, it was a hand-me-down that didn't have the memory/disk-space to run the current Windows. Since I'd been using a variety of unix systems in the at school (UWaterloo!), and at work, Linux was a more logical choice than going back to a version of Windows that the machine
could run.