Doesn't something like this exist? AKA Tour Guides? Also, I think in order to cut down costs for the people who use this service, it'd have to be a group thing

Doesn't something like this exist? AKA Tour Guides? Also, I think in order to cut down costs for the people who use this service, it'd have to be a group thing. Having a private session by a personal tour guide will be very expensive and extremely niche (ie: the wealthier people) and that, I think, will be your biggest challenge. I think another approach (which is also on my list of random ideas) is instead of having a personal tour guide, have a person that functions similar to a info kiosk instead. Example: Say you're a Canadian visiting Malaysia, and the 'host' will be someone that's informed in both Canadian and Malaysian culture and paper work/law. They're the go to person for everything, questions you have, whether it's visa, places to stay/visit/eat at. If you ever run into problems, they can advice the best course of action, etc. Naturally, they'd be well versed in both languages (yours and the country you're visiting). They'll be a number you call if you ever need anything, need a price check, need a cab, etc. (Regardless, the biggest issue is safety and insurance for a random person selling 'adventures, which you have already identified. Definitely throw a Craiglist up, sell a local adventure that you're confident in taking people on and see how that goes and decide from there. Good luck!)