There are a number of sub-cultures that exist across the USA - redneck Wyoming ranchers, deadheads, San Francisco computer gearheads, civil libertarians - he seemed to belong to all of them. He was an easy person to say of that "he is one of the members of our community".
I know that him and Sean Parker were friends going way back. Someone told me a story that on the day Parker met Mark Zuckerberg etc. at the 66 restaurant, as portrayed in the movie the "Social Network", that Parker was crashing on Barlow's couch. I don't know if that is true or just part of the legend...
You would see him at various events around New York City when he was in the city. He often went to Florio's Pizzeria and Cigar Bar, holding court with people like Jaron Lanier and others.
A friend of mine said "He lived a life many would envy".