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This smells of vaporware to me.

Certifying a new electric aircraft is hard. There are several other startups who are trying to do this and they're all struggling.

Certifying a pilotless aircraft is really hard. There are no pilotless commercial aircraft because nobody has created one that can be trusted to never crash. I'm not sure that the FAA even knows HOW to certify such an aircraft.

So logically, certifying a new, pilotless, commercial electric aircraft is likely next to impossible. At least to a cynical bum like me. Good luck Wisk; I hope you prove me wrong!

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The first gen model came out in 2011 and that's probably where the FAA authorization process development started. I doubt they are just starting it now.
"Certifying a new electric aircraft is hard."

Boeing seems to have enough regulatory capture to do this with easily, kill people with impunity, and get the CEO raises and bonuses along the way. If Wisk has their lobbyists and FAA insiders as well it would certainly ease the path.

FAA doesn't know how, just as they didn't know how to certify the first jetliner or the first light sport aircraft. This is how new regulations are made. In my experience, the FAA is pretty open minded and sometimes excited by novel concepts and will work with planemakers to figure out a certification plan.
I am sure the FAA at this moment is just super excited about working with Boeing to safety certify completely novel concepts.

Boeing totally has the required safety culture to partner on this.

Did anyone ask the engineers, or just the ceo?
Probably more of a question of when the FAA will approve such aircraft. It looks like they've been building prototypes since 2011 so I'm sure the tech is pretty solid at this point. Boeing does have experience building UAVs and I'm sure this isn't that technically different. They likely wouldn't be doing any advanced flying like going between buildings or landing anywhere but an airport.
Building prototypes since 2011? That is a long time. I wouldn’t hold my breath. I would read through some of the Glassdoor reviews.
Igor Sikorsky, early aviation pioneer and inventor in the helicopter once said:

"In those early days, the Chief Engineer was almost always the Chief Pilot as well. This had the automatic result of eliminating poor engineering very early in aviation."

Maybe time for a return to that standard for Boeing?

What ever happened to the Boeing/Aerion joint venture for a supersonic bizjet? The Boeing/Embraer JV for a 737 replacement? The Boeing/Safran JV to produce their own APU engines in-house? Will this JV also die on the vine?

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People don't really like that kind of world that much. See Oceangate as an example.
It was really a bit fortunate that the employee pilot quit.. As much of a mess as it was, it was a fair trolley problem trade, and if the owner/engineer who ignored expert opinion was not among the victims there would have been a lot more social friction over the matter of manslaughter, surviving to reframe a misfortune, etc.
Kudos for going for electric and automated approach. This is high risk but exactly the kind of thing that can open up cheaper, easier flights. Both technologies (Electric and pilot-less) are pretty clearly going to be capable enough for something in 10-20 years, so given the length of time for aircraft development it makes sense that things in development now should be trying to make this happen.
If you think this is going to enable anything that resembles "cheap", think again. IF it works, this is going to be exclusively for rich people to avoid traffic jams.

Electric is plain and simple a no-go for aircraft, the specific energy is nowhere near sufficient to actually make an impact. See e.g. the Airbus E-Fan X cancellation, and their subsequent switch to hydrogen research.

And it makes sense if you take a closer look at the development in battery technology, you will see that although $/kWh has gone down fast, kg/kWh has been essentially unchanged for over a decade. That is if you ignore numbers in university press releases but look at what is available commercially on the pack level for a safety critical application.