He's good friends with Stephen Wolfram. Take that any way you like.
A new kind of friendship.
underrated comment
I know that this is probably exactly what you mean, but Wolfram doesn't have the best reputation for humility himself.
I am not so sure about this. When you read his books or look at his Twitter feed you surely get the impression he is a self-obsessed, extremely arrogant weirdo. But when he gives e.g. a talk in person, he comes across very differently - self-reflective, engaging, emphatic and funny. As someone else has mentioned in this thread, there are really two Talebs out there...
Maybe not a lot of friends among his professional peers, but that wouldn't narrow his circle much.
Not sure they're friends, but he seems to have a good rapport with Russ Roberts (of Econtalk).