I notice that most projects he's actually billing around $50-60/hour - which is not that impressive for the US (probably much better where he lives). Maybe he stands out because his advertised rate is relatively high, and he cuts them a special deal each time?
The other thing is, why stay on UpWork after the connection is made, why not just build the client base and use UpWork as a lead source?
Maybe he starts with non-Upwork clients and then brings them "into" UpWork, getting 5 stars every time?
About a year. I started from $30/hour, then switched to $60 and current rate is for consulting because I don't have free time for full-time projects (I'm working full-time already and I love my work so don't want to switch).
2 strict rules: 1) never negotiate rate, 2) don't work too hard (I prefer to work 40 hours per week).