In my conversation with Gary Vaynerchuk for The CEO Series , I went in with curiosity — not about his personal brand or viral moments — but about the quieter, often overlooked realities of running a company over the long haul. Vaynerchuk’s energy is unmistakable, but what struck me most was how grounded he is when talking about leadership, trust and the culture he’s tried to build at VaynerMedia.

One of the more surprising moments came when we touched on what it’s like to run a business with your family. Vaynerchuk’s brother, AJ, was instrumental in building the company early on, and his father has long been part of his origin story. There’s a kind of romanticism that comes with “ family business ,” but Vaynerchuk was honest about how hard it can be — how the overlap between persona

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