He is transparently glib, but he often says one thing and does another. And his reputation for "telling it like it is" is doing the leg work of obscuring the fact that he's a massive hypocrite and can't be trusted.
I suppose he gets all the credit for being authentic due to his telling the public not to buy TLSA shares, and the way he tries to work the number 420 into share purchase prices? Its all just theatrics, just as how he (and was photographed as he) carried a sink into the lobby of Twitter last year on the day he bought it. You'd think a heavily-burdened business leader would have things of greater import on his mind than cheap imagery.