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Uber, the hungry Silicon Valley company that turned people with cars and smartphones into a transportation fleet to rival taxis (while skirting things like labor regulations in the process), has set its sights on something much larger. Uber is already working on driverless cars, which happily for the company exist outside of labor law, but not even unmanned driving machines are enough to satisfy Uber’s ambitions. The company wants a flying car.

Specifically, Uber products head Jeff Holden is looking at VTOL — “vertical takeoff and landing” — technologies. Holden expressed this interest during an interview with Recode executive editor Kara Swisher at the Nantucket Conference last Sunday. As Swisher reports:

The advantages of VTOL vehicles are many: they can land and take off using small pads, like helicopters, instead of the large and inconvenient runways of airplanes. And once in the air, VTOL craft often convert to plane-like flight, maximizing efficiency as they soar through the sky with wings, not spinning blades, providing lift.

VTOL is also, it’s worth mentioning again and again, hard. There is a “V/STOL Wheel of Misfortune,” maintained by the American Helicopter Society, that documents 45 different attempts at vertical or short takeoff and landing aircraft. Almost all are failures, with a couple of successes mixed in. Those successes did not come easy. Perhaps the most famous VTOL aircraft, the V-22 troop transport used by the United States Marine Corps and Air Force, had four crashes resulting in 30 total deaths before it was improved and finally declared operational, 16 years after its first flight.

The F-35B, the Pentagon’s VTOL variant of its expensive F-35 fighter program, is the most expensive of the bunch. DARPA is experimenting with new VTOL concepts. Bell Helicopter hopes to outfit the Marines with VTOL attack drones and the Army with a new VTOL transport or attack helicopter. These are expensive projects, with tricky aerodynamics, and none are designed to navigate a crowded street filled with pedestrians after last call.

That’s assuming Uber goes for true VTOL, where the aircraft takes off like a helicopter and transitions to more efficient, plane-like flight. If Uber is simply interested in helicopter-like flying machines, that idea is already out in the world. China’s Ehang 184 is a “human-carrying drone,” or perhaps, a driverless sky-car. The passenger-carrying quadcopter is cleared for testing in Nevada, where it may some day see use returning the drunk and wealthy from spots along the Strip to waiting penthouse helipads.

It’s helicopters like the Ehang-184, and not Osprey-like planes, that I’d expect to see Uber investing in. Anything else just seems like a VTOL tale.