Chris Wanstrath recounts how jakobo experienced hard drive troubles over the weekend but managed to avoid significant data loss thanks to backups and the use of GitHub. Chris shares his own experience of upgrading from Tiger to Leopard, noting that the use of tools like GMail, 1password, and GitHub alleviated concerns about losing critical data during the transition. He emphasizes the importance of distributing data across multiple platforms, such as using GitHub alongside other git repository hosts, to minimize the risk of data loss, as demonstrated by jakobo's experience.