He would lead his company's pitches to new clients, and would turn up to the presentation wearing a t-shirt, shorts, and flip flops; tattoos all over his arms and neck, and thereby set the expectations of the room quite low.
He would then continue brazenly with his presentation – charming, intelligent, and confident – and by the end of the pitch would hopefully have won the prospective clients with this wit.
His logic was that everyone plays the status game, but to be remembered you need to change people's perception of your status drastically. Setting expectations low, and then making them feel foolish for misjudging you.
In his words: it had varied success.