Gary Vaynerchuk aka Gary Vee is a doyen among social media experts, an angel investor and a five-time New York Times bestselling author. He is also the chairman of holding company VaynerX and CEO of advertising agency Vayner Media. Gary says he loves to ‘push Fortune 1,000 brands to embrace discomfort in order to drive innovation and success’. 

As part of the NatWest Business Show for 2024, we held a live event in London in January and our host Angellica Bell interviewed Gary on stage to create this special edition of the show.

We ask all our guests for a business confession and Gary was no exception. He told Angellica: “Candour has been very hard for me, which is always shocking for people who follow me on social media because as Gary Vee candour is actually my ultimate strength. I get to it! 

“In this interview, candour will be my strength. But in real life, when I'm an executive and really as a human being, the more I knew you and cared about you, the harder it was for me to tell you the things that I was struggling with that you were doing. And so, I think about all the sloppy firings early on that could have been done so much more gracefully.”

Gary also told Angellica in this episode: “What's great about entrepreneurship is you make your own rules. Entrepreneurship is my great passion but I’d say it’s not for everyone. Because the thing about entrepreneurship is, it's like sports - you can't hide when you fail. 

“When you start a company and it goes outta business, there's nowhere to hide. Entrepreneurship is the ultimate accountability. So, when you start to understand what that game is, it’s not for everyone.”

Angellica also asked: “What is the thread through all your experiences that have given us Gary Vee?”

Gary said: “I have a tremendous relationship with losing. I believe that the reason I'm successful in life, forget about my business accomplishments. The way I deem success in my life is: I lack anxiety compared to the majority of humans on earth. That I'm happy is completely and utterly in association to my relationship with losing.

“The reason you got Gary Vee is because my mother parented me perfectly. She put things like me being kind to people on a pedestal, not getting straight A’s. So, back to entrepreneurship, back to being resilient, back to being capable. You have to deal with adversity.”

To hear more of Gary’s fascinating takes on leadership, entrepreneurship and growing a business, watch the full episode:

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Please note that the views and information have not been endorsed, issued or approved by NatWest. Any views expressed in this podcast are not necessarily those of NatWest.