AirBnB has it a bit easier, because they let normal people rent out their own space (which involving tidying up a bit and locking away the valuables, basically)

AirBnB has it a bit easier, because they let normal people rent out their own space (which involving tidying up a bit and locking away the valuables, basically), and normal people are qualified to do that, more or less. The folks who are qualified to run adventures probably do exactly that, professionally, and so are already listed in the yellow pages, have their fliers in the local tourist offices, may be listed (and reviewed) on the Lonely Planet site, etc.. Though, if you're focusing on a wealthy clientele, you could well have professionals listed offering experiences that they only do rarely, and aren't available otherwise. Alternatively, you might be able to aim for mini or offbeat adventures as well, likewise only rarely available. "Get a tour of Chicago's graffiti from a famous (reformed) graffiti artist". "Tour of a (private) organic farm and lunch with the owners; offered 4x a year." "Letter-press tour and workshop in an active shop" -- etc.. I have a friend in central France, a professional baker with a massive wood-fired bread oven who tried giving daylong workshops on making organic bread a few times a year; it was pretty tricky to organize something so irregular, though, as she couldn't do it unless it was fully booked (if there were only a couple of people whose schedules lined up with a date, she would need to cancel it). There's a pain point that'd be nice to fix. HTH.