A lifelong entrepreneur and longtime tech investor, VaynerMedia cofounder and CEO Gary Vaynerchuk has invested in more than 50 startups, including Twitter, Tumblr, Medium, Birchbox, Uber, and Venmo.

Fresh out of college he took his family wine business and grew it from a $3M to a $60M business in just five years. Now he runs VaynerMedia, one of the world’s hottest digital agencies. He has been described as “the first wine guru of the YouTube era”, and “the wine world’s new superstar”.


Here are 10 success lessons from Gary Vaynerchuk – “Wine World’s Superstar” for entrepreneurs,

1. Nurture contacts

Vaynerchuk stresses nurturing contacts and spending a fifth of your time seizing the chance to strengthen those bonds. “Reinvest in the relationships you already have,” adding, “My biggest objective is to have the most people show up to my funeral as possible. I’m sorry. That’s what it is.”

2. Bet on your strengths

Gary mentions that the first true step to success is find out what your real strengths are and quadruple down on them. In entrepreneurship, there are many people trying to chase what one “thinks” they are good at. Instead, Vaynerchuk encouraged everyone to take part in an exercise of self-awareness.

He instructs everyone to find the three to five closest people around them in their day-to-day lives and to separately ask these individuals for brutally honest feedback. Through this honest exchange, we should be able to better understand what we excel at, what areas we can work on, and most importantly, a more thoughtful compass to guide us through our professional and personal journey.

3. Don’t chase the unicorns

While the allure of companies with billion-plus valuations is very appealing, Vaynerchuk discourages early entrepreneurs from following this hype too closely. As he pointed out, for every Instagram, there are thousands of failed replications. It’s not always important to set out building the “next big thing.” Instead, entrepreneurs should build their applications in a way that addresses true pain points in life.

4. Hustle

Gary calls hustle the “most underrated word ever.” He eats, sleeps, and breathes it every day through his insane work ethic. He’s often up at the crack of dawn until the wee hours of the morning. Somehow, Gary manages to juggle a crazy amount of responsibility and projects (running companies, blogging, writing, investing, traveling, etc.) and love every second of it. He’s been doing it his whole life and hasn’t stopped.

5. Dream big

Gary makes sure everyone knows that he wants to own the New York Jets some day. Having a lofty goal such as that one makes the climb to the top that much more enjoyable. Gary is all about passion, especially encouraging his fans to pursue theirs on as large a scale as possible. He defines happiness as the ability to do exactly what you want every single day of your life.

6. Follow up on each and every social media comment

This may sound like a large task, but the hours put in will yield exponential results. Following up on each comment with a unique and insightful response, not only makes the commenter feel great, but it shows others viewing your comments you actually respond to users. This is a great way to humanize your brand and encourage users to engage and connect.

7. Enjoy more

Vaynerchuk points out that despite the demands of his business, his weekends aren’t spent working — they’re spent with his family. “This isn’t tactical,” he said. “This is a decision.”

Vaynerchuk realized recently when planning a vacation with his wife that he could have planned any number of other trips and hadn’t, and wouldn’t get that time back. Since then he created clearer divisions between his business and personal time. “I’m not super smart but I’m a good halftime adjustor.”

8. Be human

In life and business there’s the pressure to make certain connections or get a certain type of visibility. But as Vaynerchuk notes, closing yourself off to experiences or people only limits your own opportunities. “I promise when you stop strategizing about people’s clout and start acting like a human being you will win.”

9. Be grateful

Vaynerchuk was born in the eastern European country of Belarus and immigrated to the U.S. with his family when he was three. He sees that as his great luck, understanding the opportunities that entrepreneurship has afforded him.

“I hate hearing people complain their glass is half full when it is 4/5 full,” Vaynerchuk said. “I’m grateful when there’s one drop because I know what to do with that drop.”

10. You’re worrying about things you shouldn’t be worrying about

Worry less about whether or not you “should be” present on social media and just do it. If you’re already on social media, you’re not doing it right because you’re only talking about yourself. Start listening to people and delight them.

About Author

Biplab Ghosh

Biplab lives his life around technology and is particularly keen to explore the intersection of technology and human behaviour. Always looking for new ideas, and ways that can make things simpler. He is a geek with the flair for travel and has great passion for music and theatres.

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