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People who know Gary Vaynerchuk may think that taking risks come easy to him. As a bestselling author, blogger, and entrepreneur (founder of Wine Library and Vayner Media) maybe we think that his personality is suited to initiating, or that he always had support along the way.
On the contrary. Real life has a way of taking our assumptions and turning them upside down, and if we look closely at Gary’s trajectory we see it’s actually built on a foundation of getting criticized, of taking the risk even though people around him told him not to. It’s also built on his ability to keep poking at authority and asking “why not?”
Here’s a video Gary made on what it means to him to Poke the Box: