• Vine

    This is less a tech flop than it is a case of tragic mismanagement by the company that acquired it. Vine was an instant hit when launched in 2012, limiting shared videos to only 6 seconds long and forcing creators to be extraordinarily creative. Twitter bought it and couldn't figure out how to make money off the service—money-making not being Twitter's forte—so it shut down in 2016. Vine's co-founder said he'd launch a sort of Vine 2.0 by 2017, but financial and legal hurdles killed that before it was even born. Maybe his latest project, Byte (Vine 3.0?), will eventually become available, but with TikTok taking over short-form video, who's going to care?
  • Windows 8 + Windows RT + Windows Phone

    With the memory of Vista fading, Microsoft was riding high on the success of Windows 7 when it launched the ill-advised Windows 8 in 2012. Changes to the OS—tiles, ugh—and attempts to make it more mobile-friendly all sent users into a rage. A year later, with Windows 8.1, Microsoft was walking back a lot of the interface "enhancements" to be more like Windows 7 again. When Windows 10 came along as a free replacement, and was welcomed with open arms by 8-haters and lovers alike.
    Windows RT was a cripple-ware version of Windows 8, made just for tablets and laptops with lower-power chips to save money. It was crippled in that it only would run apps from the Windows Store—an Apple-esque move at which traditional PC users chafed. Thankfully, when Microsoft moved the Surface line of hardware to the high end, it killed off the low-end RT OS.
    Microsoft's other big OS failure came in three stages through the last decade, with Windows Phone 7, Phone 8, and finally Windows 10 Mobile. Maybe someone out there liked having their desktop OS shrunk down to a phone screen, but obviously not enough. Microsoft finally killed the last vestiges of its experiments with mobile in late 2018. Bill Gates blames the feds.
  • Honorable Mention: Apple's Project Titan

    It's taken as a given that Apple's been looking into battery-powered, self-driving vehicles for a long time. Its autonomous vehicle group even has a name, Project Titan, and has been in existence since 2014. In 2018, the group had 27 cars registered for road testing. However, it recently laid off 200 people and shifted other staff around. Yet, it also bought Drive.AI, a tech for artificial intelligence in self-driving vehicles. Could a car still launch from the Cupertino loop by 2023, give or take? Or license tech out to others to make such a car? Check back again in 10 years. (iCar concept image courtesy of designer Meni Tsirbas, @MeniThings on YouTube)