I don't think this party crashing has brought him significantly closer to his success goals. Not once did he give an example of a time he was able to successfully leverage a new connection to his benefit. He basically name dropped a handful of famous people that he met one time, but that's it.
The only benefit I see is that he's actively stepping out of his comfort zone. This is valuable, however, it's at the cost of charity. There are better ways to go about exercising this character trait.
I've seen it work for him in person in Austin about 7 years ago. I think (some) local entrepreneurs value his gusto. His reasons seem different than party crashers from DC, he just does extraordinary things to be able to talk to successful people.
That said, most people will not be able to replicate.
The only benefit I see is that he's actively stepping out of his comfort zone. This is valuable, however, it's at the cost of charity. There are better ways to go about exercising this character trait.