He does quite a lot of dates and some are pretty accurate. Computers winning chess he predicted one year later than it happened.
Turing test he predicted 2029 and while not very clearly defined I'd say that is happening about now.
Predicting those things are kind of easy if you have the background in the technology that he does. But the singularity? How can you compare that to computers winning chess?
It is not grift though, it does cost in that ball park for international private long distance flights in the 10,000+ mile range . Planes that can do this like say gulfstream V would seat 15-20 people , so like 25k per seat , it is not that much more expensive than a first class ticket cost wise if you think about it