They were totally different entities. Kesey took the bus, and members of what would become the Dead's family, to see the Beatles at the Cow Palace in '65 or so. Jerry Garcia said he learned a lot there, about the interaction of crowd and band.
Specifically, how not to do it. 
Unless you wanted to be confronted with 20,000 egos all charging the stage and screaming, in kesey's words, "me!" "me!" "me!"
The Dead weren't pursuing "success" in conventional terms, because anyone who has been to the top of the zen mountaintop knows just how transitory and empty those things (indeed, all things) truly are.
And yet they still managed to be extremely successful. And by all accounts, in one form or another those gents have had a great fucking time for up to 50+ years in some of their cases, with a lot of other people having a great fucking time with them.
Also bringing untold amounts of joy to many, many people.
If that's not success, I don't know what is.
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