The Alchemy of Authenticity

The recent Friends reunion had me thinking of one of my favorite Jennifer Aniston movies: Office Space.   

There’s so many reasons people love that movie—the “jump to conclusions” mat, the baseball bat assault on a misbehaving printer and of course, Lumbergh. 

But what always struck me about Office Space is that every character in it wanted to be someone, or somewhere, else. It came out the year I graduated business school and spoke to a widespread feeling that you had to put up a front and be kind of a fraud to get ahead in corporate America. 

Fortunately, I don’t think that’s true anymore. Sure, there’s still plenty of politicking and fakery going on within organizations. But there’s also a growing awareness that the best employees, and best leaders, come in so many shapes, styles and colors. 

There is no one right way to act or way to be. The best leaders are the ones most comfortable just being who they are. 

That’s the definition of authentic leadership.  

If leadership is the act of inspiring other people to follow you, then authenticity is becoming the non-negotiable leadership trait that every aspiring leader needs to have. Authenticity is also something that consumers increasingly demand in the companies with which they do business.  

Given that being authentic often means rejecting conformity, it is hard to pin down a formula for what exactly makes a leader authentic. But the Harvard Business School professor Bill George has probably done more thinking on this than anyone, and he says authentic leaders tend to have several traits in common. They have a purpose they pursue with passion. They have strong core values and act in accordance with them. They know how to build relationships and connections with the people they aspire to lead. They have self-discipline and consistency. And they have heart and compassion for other people.  

This describes to a T one of the best and most authentic leaders I know, Gary Vaynerchuck. I’ve been friends with Gary—a serial entrepreneur who expanded his family’s wine business, created a wildly successful digital ad agency and now runs a sprawling communications company called VaynerX—for years. If I ever want to understand what’s coming next in culture or media, I call Gary. 

Gary was born in Belarus, before his family moved to Queens and he kind of looks and sounds like a lost member of the Beastie Boys. He even has a Beastie Boys-esque nickname: GaryVee.  

And like the Beasties, Gary is a creative genius. He sees and shapes trends before anyone else. So when I caught up with Gary recently, I was so excited to talk to him about what might be his biggest undertaking yet: a new NFT-based collaboration called VeeFriends 

Gary’s success is built on many things. He’s passionate about everything he does, which makes other talented people want to work with him. He has tremendous empathy, and he believes everything he hopes to achieve is dependent on his ability to connect with other humans. And though he cares so deeply about his work, he is philosophical enough to say the thing we all know, but often need to hear: “Everything is bullshit outside the health of your family.” 

What I love most about Gary is that he is fully who he is—wherever he is. That authenticity explains why he has nine million followers on Instagram, but it’s also why I believe him when he says he wouldn’t care if his follower count went to zero.  

I’m lucky to call Gary a friend and I invite you to check out my latest Conversation with C Series, in which I talk to him about what it means to be authentic, why he owes so much of his success to his amazing mom, and why he thinks his number one job as a leader is to eliminate fear by showing something he calls “kind candor.” 

You can listen to our full conversation here.