Styjun

The website states they're not a Part 380. Love their service -- how will they avoid the same fate as Flytenow?

Long story short, Blackbird appears to be set up so that the customer leases an aircraft and separately hires a pilot to fly it. That makes it a 'straight' part 91 operation.

Blackbird's terms and conditions for pilots specifically mention 91 B but not K and include a few interesting points (emphasis mine):

• Pilot services are offered as an independent contractor to users under a dry lease
  


• The pilot is not directly employed by the owner of the airplane


• The pilot operating the flight cannot own the aircraft being rented


• 
  Pilot hiring is at the discretion of the passenger; BlackBird will facilitate matching pilots with aircraft based on passenger
  selected routes, pilot qualifications, and location and availability
  of both pilot and aircraft


• Pilot understands that passenger (lessee) renting the aircraft and hiring the pilot accept and maintain operational control of the flight; these operational duties may be delegated to the pilot in command.

In other words, the passenger rents an aircraft from an owner and then separately hires a pilot to fly it, according to the passenger's instructions. Blackbird is saying that they only provide a marketplace, and the customers actually lease and operate the aircraft themselves.

This is from their general term and conditions:

The Platform provides a marketplace that enables users to (a) connect
with and lease aircraft from third parties that own, lease, or
otherwise control aircraft (“Aircraft Owners”) and to find and hire
flight crews (“Flight Crews”), or (b) join flights with third-party
operators or other BlackBird users on the Platform (“Third-Party
Operators”).

And:

If you wish to lease an aircraft from an Aircraft Owner and / or hire
qualified Flight Crew, then you can use the Platform to search for
available aircraft and Flight Crew

Because the owner just rents out the aircraft without a pilot, they aren't operating an air carrier. Because the pilot doesn't provide the aircraft, they aren't holding out. That means the only pilot qualification needed is a commercial certificate, although Blackbird also requires 500hrs, an instrument rating and a background check.

Now, whether or not that business model will survive if the FAA gets interested in it is another question. There was some discussion on the AOPA forums (members only) a while ago about Blackbird and I think the consensus came down to "technically legal, but pushing their luck with the FAA and DOT".

A semi-useful comparison here might be Uber. They've always claimed that they aren't a transportation company but rather a marketplace that just connects independent drivers with customers. That argument has succeeded in some places but not in others, and many countries and cities have decided that Uber is a transportation company and started regulating them. I have no idea whether or not that will happen with Blackbird.