The Shocking CEO Blindspot Gary Vaynerchuk Exposes That Could Make or Break Your Empire—Are You Falling Into the Same Trap?

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 personal relationships and professional expectations can become complicated fast. And yet, he said he wouldn’t have it any other way. What came through clearly was that for Vaynerchuk, legacy isn’t just about scale or valuation — it’s about who’s with you when you’re building.

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We also spent time unpacking what’s changed in how he sees his own role as a CEO. Vaynerchuk admitted that his younger self would often lead with intensity, but over time, he’s learned that empathy, patience and understanding are the real tools of influence. He now sees kindness as a competitive advantage — not in a performative way, but in the way you create environments people want to be a part of. That’s not something you often hear from media CEOs whose companies are moving at a thousand miles an hour.

On leadership, Vaynerchuk had a clear message: Too many CEOs confuse being in charge with being in control. He said something that stuck with me: “A lot of executives are addicted to saying ‘no.’ It makes them feel powerful.” His approach is different. He sees his job as creating the right conditions for other people to do great work, not micromanaging or asserting his authority just because he can.

Naturally, we talked about content and attention. He still believes in the power of showing up where people are — whether that’s LinkedIn, TikTok, YouTube or the next thing coming around the corner. But he was just as quick to point out the emptiness of playing the algorithm game without substance. “You can win short-term by being loud,” he said, “but long-term, people can smell intent.” It’s the clearest articulation of his philosophy: Attention is just the doorway. Trust is what matters after you’ve walked through it. After all, VaynerMedia didn’t grow to a global company just because Vaynerchuk had a good social presence.

What surprised me most, though, was how often he returned to the idea of being at peace with yourself. Not in a vague, wellness-culture kind of way, but in the context of being a leader who can sleep at night. He talked about how many business leaders are chasing validation that will never come and how important it is to define success on your own terms. That perspective, especially from someone operating at Vaynerchuk’s level, felt honest and rare. It’s something that’s rare to find in a person with the title of “CEO.”

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I walked away from the conversation thinking less about hustle and more about values. There’s a version of Gary Vee that exists online — quick cuts, punchlines, big energy. But in this setting, I saw someone far more reflective. He’s still playing that game, but he’s doing it with a clear head, a long view and people he trusts by his side, including family. And that, in many ways, is the story most worth telling.

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 personal relationships and professional expectations can become complicated fast. And yet, he said he wouldn’t have it any other way. What came through clearly was that for Vaynerchuk, legacy isn’t just about scale or valuation — it’s about who’s with you when you’re building.

Related: How Morning Brew’s CEO Succeeds With Clarity and Restraint in Today’s Noisy Media Landscape