Kevin says that we talk about smartphones as being a "mature" technology by now, but when he uses GPS on his phone, it frequently can be wildly inaccurate. For instance, when he was in Scottsdale, he asked Siri for Thai restaurants, and it gave him results for Florida. Why would that be the case? Leo says that "mature" doesn't necessarily mean it's better, it's just an older technology at this point. Apple is doing everything it can with GPS, but its still an imperfect technology. The phone has to triangulate his position with cell towers and satellites, and download the almanac if it's the first time in a given location. If it can't triangulate, then it has to use the IP address, which can be inaccurate.
Leo recommends opening the Maps app and let it load the maps for the area he's in. He also should make sure he has given Siri location permissions, and that his GPS is enabled.