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This was completely expected: while Uber and Lyft can mostly carry out arbitrage against the patchwork of local regulations on taxi services across the country, air travel is federal and there are no conflicting local rules to take advantage of at different times, just the FAA saying "yes" or "no" nationwide.

And it also shouldn't be controversial: everybody knows Uber and Lyft are taxi services, despite their occasional "we're not a taxi, honest" dodges, and doing the same with aircraft... makes you an airline, and trying to go back and pull a "we're not an airline, honest" is not going to fly.

I don't care whether or not it's classified as an airline, but if I want to catch a flight with a private pilot and compensate him, fully understanding the risks and rewards of general aviation vs commercial aviation, where's the problem exactly?
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Private pilots by regulation cannot be compensated. Only commercial pilots can be; and even in that case the buyer must separately acquire the pilot for hire, and plane for hire. If the buyer goes to a single source for pilot and plane for hire, that is an air carrier, i.e. commercial aviation.
I think the complaint is that the law should have exempted situations where there is explicit and informed consent on what is happening.

Why should only those with rich friends/family be able to a flight from A to B via private plane/pilot?

If a plane is safe enough for me to fly my whole family in, why is it too unsafe to fly someone else?

You don't need rich friends/family. People charter small aircraft all the time.

The difference is those operations comply with applicable regulations while this doesn't.

That's not correct. See 14 CFR 61.113 (c) A private pilot may not pay less than the pro rata share of the operating expenses of a flight with passengers, provided the expenses involve only fuel, oil, airport expenditures, or rental fees.

edit: the exceptions of the CFR are (b) through (h) but (c) is the most typical

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Okay, then what would you call it?
Tried to edit my other comment but accidentally deleted it.

So I just skimmed over the ruling here:

https://www.cadc.uscourts.gov/internet/opinions.nsf/77E3D4B7...

and you're right (if you're getting at what I think you're getting at).

The argument is that expense sharing is compensation, but it is allowed under the FARs in specific circumstance. Difference here being that the combination of holding out on a public website and receiving compensation via expense sharing put it in common carrier land.

Which does seem to make sense under current rules.

Np. And right. I hated to be pedantic but outright dismissing the fact that there are exceptions to the compensation rule is wrong.

edit: wording

Sharing operating expenses is not the same thing as compensation which connotes services rendered.
Sharing expenses is compensation and the reg alludes to that fact in part (a) and by virtue of the list of the exceptions to said reg. If you really need a concrete example that includes the "compensation or hire" verbiage look at exception (b) of the reg.

(a) Except as provided in paragraphs (b) through (h) of this section, no person who holds a private pilot certificate may act as pilot in command of an aircraft that is carrying passengers or property for compensation or hire; nor may that person, for compensation or hire, act as pilot in command of an aircraft.

(b) A private pilot may, for compensation or hire, act as pilot in command of an aircraft in connection with any business or employment if:

(1) The flight is only incidental to that business or employment; and

(2) The aircraft does not carry passengers or property for compensation or hire.

The difference seems pretty clear: Profit. Uber/Lyft drivers aren't splitting the cost of gas with riders; they're making money from it, as evidenced by the fact that rates change hour by hour with market demand. They can claim they're not taxis, but their compensation structure says otherwise.

I am not a lawyer, but if Flytenow is truly doing what they say and are facilitating riders and pilots to share cost, then it is hard to argue that it's a commercial endeavor because the pilot still loses money; just like I am not a taxi if I drive you down to LA and we split gas-- how we found each other and whether we are strangers seems irrelevant.

The FAA has a concept of "Common Purpose." You can't share expenses if the pilot and the passengers don't share a common purpose for the flight, that is, there is some other reason than just splitting the expenses for them to go together, for example, they are all going to the same meeting or on the same vacation. Generally the reason is that the regulations are far more lax for a private operation than a commercial operation, and the FAA wants you to be in a position to judge their character and judgment before you decide to fly under regulations where the FAA isn't guaranteeing much itself.
> >and doing the same with aircraft... makes you an airline

It actually makes you an air taxi; FAA Part 135 operator. Still requires a commercial pilot's license though.

Couldn't this technically continue to run "under the radar"? (pun intended)

If this is already legal as they mentioned, but not as a "platform", you could just work on better facilitating the communication and let payments and logistics happen offline (or in private like email)

Heck, use a cryptocurrency for extra plausible deniability on payments.
The issue here is that pilots are not going to risk the licenses they've spent potentially over 100k on to make money this way.
I think the FAA was the issue, not the pilots. Those who don't want to give rides, won't. That's pretty simple. The FAA even said that splitting the cost of rides with friends is OK, so then it will be down to proving if someone is your friend or not.
It's possibly a safety concern. With paragliding, which is largely self-regulated by the USHPA (FAA airspace use regulations notwithstanding), I don't believe you can technically take payment for a tandem flight unless the passenger is a student pilot, at least on paper.[1] IIRC, this is to discourage pilots with a tandem rating taking undue flight risks to make money on giving rides.

[1]: https://www.ushpa.aero/4721.asp

It's depressing to me that the useful idea of a "sharing economy" has been redefined to mean "Uber and things similar to Uber."