Mark Twain famously lost his fortune investing in the Paige Compositor, a so-called mechanical miracle of an automatic typesetting machine that ultimately failed to deliver on its revolutionary promises. This historical cautionary tale from the first Machine Age highlights the recurring pitfalls of overhyped automation and the harsh realities of scaling early technological innovations. Modern tech leaders can draw valuable lessons from Twain's financial ruin as contemporary automation technologies continue to disrupt traditional industries.