BlackBerry convinced the entire Fortune 500 that a physical QWERTY keyboard on a phone was peak innovation — and then watched in real-time as Apple deleted their entire business model in one keynote. RIM's response to the iPhone was to release a phone with a slightly bigger keyboard. Their security was legendary. Their foresight was not.

Internet Explorer had a 27-year run, the last 20 of which were spent being the punchline of every web developer's darkest nightmares. It didn't support CSS correctly until 2011. It crashed on hover. It was the reason "works best in IE" became a warning, not a recommendation. Microsoft finally killed it in 2022 — a mercy killing 15 years overdue.

HD DVD entered a $1.5 billion format war with Blu-ray, staked Toshiba's entire hardware division on it, got Warner Bros. to defect in January 2008, and folded by February. Two months. It is the most expensive way anyone has ever said "we misread the room." The real tragedy: both formats lost to a website with a password-sharing problem.

MySpace let you customize your profile with autoplay music, seventeen animated GIFs, and a background that made the text completely unreadable — and somehow this was considered a feature. News Corp paid $580 million for it in 2005. By 2011, it was worth $35 million. Justin Timberlake co-owned the relaunch. Not even JT could save it. Tom is still your friend, though. Tom is always there for you.

Windows XP was so good that people refused to stop using it even after Microsoft begged them. It powered cash registers, ATMs, air traffic control terminals, and hospital equipment for 13 years past its end-of-life date. Microsoft issued emergency patches in 2017 for an OS they'd already buried three years prior because North Korea was still on it. XP didn't die. XP is infrastructure now.