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What about surge pricing? Will you give me my first fare free? How often do you screw over pilots by raising your rates? Are the planes older models? This guy doesn't know where the Bermuda Triangle is, and his GPS stopped working. What should I do?
They tout their integration with Apple Pay and TouchID. Is it really wise to trust your phone with the ability to authorize transactions in the tens of thousands of dollars?
It's really more of a question of whether or not it's wise to accept such payments.
I don't understand this concern.

I walk into a jeweler's with a bit of 3 year old plastic and walk out with a six figure watch.

Is it really wise to trust this bit of plastic with the ability to authorize transactions in the tens of thousands of dollars?

Why is adding my fingerprint to the transaction worse?

None of the 'book' links on their page work? Is this actually running yet or are they just touting for planes at this point?
This was a horrible idea to put online, when it's not functional and appears to be broken.
How many of these things have been shut down by the FAA so far?
Some quick googling suggests 'AirPooler' and 'FlyteNow' have both been disrupted by the FAA, FlyBlade and Bluestar Jets and Blackjet may or may not be doing something different to stay within the bounds of the law.
Stellar says they're "the world’s first commercial operations system for Part 135 business jet operators", which means their flights have commercially licensed pilots working for regulated carriers, not private pilots illegally carrying passengers for hire, like FlyteNow's pilots were. So it sounds legal.
Nothing new here, On-demand charter flights and empty-leg market arbitrage as been going on for years, the UK as a very strong market.

The fundamental problem is lack of inventory on the supply side and high costs.

flight sharing a private charter between east and west coasts seems feasible, right?