It's likely not like this everywhere but I've become a regular at a few places over my life time and asked about this. At least where I've been, it is actually all tracked. Generally, at least at bars, the people coming in and tipping well, are people who come in often and spend a lot to begin with so over the long run they end up making it back anyway. And honestly, when you're new to a city/place and don't have a lot of friends/are single, and you walk in somewhere and are greeted by name and served your usual without asking it's a nice retreat.