Operational Control: Can I fly?

You are being paid to fly the plane that you are operating. As long as the passengers aren't paying for the flight, it doesn't matter who they are. The boss could offer the plane to whoever he/she wants as long as no money exchanges hands. There is an entire network built around this with Angel Flights and Corporate Angel Network. Those cancer patients have no relationship with the owner, but you could legally fly them.
 
If you are my Part 91 pilot, the passengers aren’t your concern UNLESS you believe that they are paying for carriage and the aircraft should be governed by 135.
beat me too it...owner told his pilot to fly some passengers (pt 91), BUT if those passengers sought you out and are paying for carriage (pt 135)
 
You’re making this way too convoluted.

The owner says jump, you say how high. It doesn’t matter who the passengers are unless you believe someone is paying the owner for the use of the airplane.

As long as the people walking on the airplane are invited guests of the owner, don’t worry about LLC 1, Corp 2 and so on and so forth. If you get ramp checked or CPB asks, “Guests of my owner.” End of story.

Also, this has nothing to do with operational control. By definition operational control is the ability to initiate, conduct and terminate a flight. Your question is more related to financial responsibility among the umbrella entity that is your owner than it is to operational control.
 
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Backtracking a tiny little bit.

The quick smell test is whether passengers are paying for carriage. However, that test isn’t exhaustive.

While the interpretation of the rule is pretty liberal, Part 91 flights must serve the interest of the ownership in some way, versus a public interest. They can donate flights for charitable purposes but they can’t operate strictly in the public interest.

If I create a charter service that transports cancer patients for free, it can’t be operated under Part 91 as that’s viewed as offering services to the public, albeit uncompensated.
 
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Operational control IS a factor in Part 91, however, as posted, there is NO issue flying the Corp 2 pax. Unless, as posted above, you know or suspect that the PAX are paying.

Are they leaving a envelope full of money near the door when they leave? Not good……!
 
Unfortunately the IRS and the FAA have different views, so it gets convoluted. Typically, however without full details, you may fly anybody as long as there is not compensation to LLC1. Parent, affiliate, subsidiary companies are in some cases allowed to reimburse for expenses however that is a bit more in depth and kind of requires knowing more about the story. Separate or non affiliate companies may share operational expenses either under a time share, or dry lease - however again there are considerations. If this is going to be a normal thing and the boss wants so move expenses between two separate companies a simple time share agreement is probably what you want. A wet lease generally requires an operating certificate and under a dry lease agreement, you as a pilot for LLC1 cannot fly for LLC2 as LLC2 in a dry lease must maintain operational control. If you want to play the game of "time off from LLC1 and Contracted by LLC2" go ahead, but, if it looks and smells like LLC1 still has OC by placing you on the aircraft - it won't fly.
 
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