There was a guy in Atlanta around 1998 that tried to do something that seems a bit like this. His idea was to sell empty seats on biz jets but serve certain city pairs. The idea was to get around the "scheduled service" and keep the planes as 135 on demand by creating a website for people to sign up. I believe the Atlant FSDO signed off on the idea. The flights did not have a "departure time", so the first person that signed up had the option of setting the departure time and the rest were just buying empty seats.
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