This chapter reflects on John McDaid’s author traversal of his 1993 hypermedia novel, Uncle Buddy’s Phantom Funhouse, a groundbreaking work not just for its comprehensive exploration of Apple’s HyperCard authoring system, but also because of its principle of “modally appropriate” presentation, involving non-digital artifacts as well. Built around the science-fictional notion of time travel and multiverses, the Funhouse thus invites consideration of his own curious history, in which it figures as a kind of broken time machine. Comparing McDaid’s work with later, similar projects from the video game world, the chapter argues for an understanding of digital culture that moves beyond the harsh binaries of obsolescence. As McDaid says: “We win by losing.”