There are two mechanisms by which technologies affect society: bundling and unbundling. This re-packaging resets the way companies are structured leading to reversal of incumbent position relative to entrants. The Personal Computer unbundled the mainframe while the phone and tablet unbundled the PC. Microsoft bundled office work and the Internet bundled communications. Google unbundled information access and Apple bundled experiences. Amazon bundled retail while Facebook bundled media. The car in the 20th century bundled transportation. Will the availability of new technologies in the 21st century enable a great unbundling of transportation?