A decade ago, Gary Vaynerchuk was filming video blogs about wine against an unremarkable beige wall, with a handful of opened wine bottles and a plastic spit bucket in front of him. He'd give his glass a good stir and proclaim some initial thoughts: a California cabernet was "very chocolate-oriented," a French viognier evoked "a little bit of dandelion."
One thousand episodes of "Wine Library TV" later, Vaynerchuk had amassed a huge following and was a founder of VaynerMedia, a social media company, along with his brother AJ Vaynerchuk. Fortune named him to the 40 Under 40 list in 2014.
Vaynerchuk, now 40, has since published five books and launched "#AskGaryVee," a YouTube series where he answers questions about business and entrepreneurship. In his latest book, #AskGaryVee: One Entrepreneur's Take on Leadership, Social Media & Self-Awareness, Vaynerchuk draws from the videos and discusses how he got started in the field, the importance of social media and why leaders should be more self-aware.
One mistake entrepreneurs tend to make is overestimating their abilities, Vaynerchuk writes. He cautions against jumping too quickly into new ventures, and recommends building up some thick skin for those who do take the risk.
Reaching high is good, as long as people hold on to their sense of reality. For Vaynerchuk, that meant learning to stay away from the things he wasn't good at and instead highlighting his strengths.
"It's insane how much humility has been instilled into me by the market and has balanced my ego and self-esteem," Vaynerchuk writes in his book.
Below is an excerpt from his chapter on self-awareness:
What was the biggest decision in your life that made you successful today?
It was the day I made the choice to suck at school.
Fourth grade. Mr. Mulnar’s science class. I got an F on a science test. To make shit worse, I had to get it signed by my mom. To avoid being punished, I hid it under my bed, where it sat for two days until my conscience got the better of me and I showed it to my mother.
Until that moment, though, I was in hell. I distinctly remember sitting in my small bedroom, crying and trying to make sense of why I was having such an intense reaction to this test. And then it hit me, the thought that changed everything:
“Screw school. I’m a businessman.”
I made the conscious decision to eat the pain four times a year when report cards came, to eat the pain of failing pretty much daily. Who cared if everyone thought I was a “loser,” a kid without a shot? I knew better. I saw something different. Even at that young age, I was self-aware enough to realize what I was born to do.
It’s not that I didn’t care. I went to every class. I was respectful to my teachers. I just decided that I would be better off honing my skills and concentrating on what made me happy and what fulfilled me. I learned about selling baseball cards, which then became wine, which became WineLibrary.com and VaynerMedia and everything that makes me so immensely proud.
That moment marked the first time that I decided to fight what society expected of me and deliver on what made me happy.
And you should, too. Bottom line: Stop doing things that make you unhappy. I’ve been preaching this since my first book came out, and long before that. Sure, it sucked to get those report cards every quarter, but sometimes you have to take a thousand punches before anything good happens. Not everyone will understand what you’re doing, and the more you work, the more chances you have to be disappointed. Or even to be the disappointment. But don’t let those moments fool you. An instance of failure could be a huge opportunity.
Pay attention. Learn to be self-aware. One F on a test got me started. Countless bad report cards got me going. And if I could go back, I would fail every single test all over again.
#ASKGARYVEE. Copyright © 2016 by Gary Vaynerchuk. Reprinted with permission from Harper Business, an imprint of HarperCollins Publishers
CORRECTION: A previous version of this story incorrectly stated Vaynerchuk has published four books. He has published five.