Gary Vee: The Hustle Evangelist Reshaping Entrepreneurship

CEO. Wine critic. Angel investor. Author. Speaker. Influencer. Inspiration.

Considered by many to be the literal definition of success, Gary Vaynerchuk, better known online as Gary Vee, wears many hats. Or he has his fingers in many pies, depending on your perspective.

So, who is Gary Vaynerchuk, and how is he reshaping the world of entrepreneurship? Let’s explore.

The Gary Vee story

GaryVee
Gary Vaynerchuk is a serial entrepreneur and serves as the Chairman of VaynerX, the CEO of VaynerMedia, and the Creator and CEO of VeeFriends. Gary is considered one of the leading global minds on what’s next in culture, relevance, and the internet. Known as “GaryVee,” he is described as one of the…

A six-times New York Times bestselling author, serial entrepreneur, social influencer, and podcaster, Vaynerchuk has done it all. Here’s the Gary Vee story.

But first, wine

Did you know that Vaynerchuk got his start in the wine industry? The future millionaire kicked off his career at just 14, stocking shelves at his family’s liquor store.

A decade later, he began investing in digital strategies considered incredibly innovative in the late 90s, from email marketing to e-commerce. He continued experimenting with digital marketing over the years, capitalizing on opportunities before his competitors could catch up.

For example, soon after a little-known video platform called YouTube was launched in 2005, Vaynerchuk created one of the first-ever long-form video shows on the platform; on WineLibraryTV, Vaynerchuk reviewed the wines they stocked, revealing his propensity for innovation and strategic thinking.

No one knew it then, but this was just the beginning of what Vaynerchuk would achieve.

Web 2.0

In 2008, Vaynerchuk’s life changed forever when he gave a keynote speech at the Web 2.0 Summit, speaking on building personal brands on social media. Remember, at the time, social media was relatively new; Myspace, Bebo, and Facebook were all the rage, and Instagram hadn’t even been invented.

This speech launched his career, landing Vaynerchuk a mega book deal and catapulting him into the public eye. Being the savvy businessman he is, Vaynerchuk immediately jumped on the opportunities that opened up to him, releasing several books and founding a digital marketing agency with his brother, VaynerMedia.

Jab, Jab, Jab, Right Hook

To some, it may appear like Vaynerchuk never sleeps. After all, how does one person have the time to run multiple companies, seek out and invest in new businesses, shoot video content, upload on social media, write books, and spend time with their family? It seems impossible. Yet, doing the impossible is what Vaynerchuk is best at.

But this is just part of what has made his personal brand as strong as it is. Here are the five critical tenets of Vaynerchuk’s content strategy:

1) An engaging personality
Even if you didn’t know Vaynerchuk’s story before today, you’ve probably heard the name ‘Gary Vee.’ His high-energy personality and candid communication style are enough to send any video featuring Vaynerchuk viral, whether he’s speaking about business success or the importance of sleep, reaching people from all walks of life.

2) Consistent branding
Vaynerchuk understands that consistent branding is powerful, from his conversational manner of speaking to using his literal signature as his logo.

3) A content creation machine
Vaynerchuk advocates hard work, consistency, and strategic thinking, allowing him to focus his energy on what will deliver the best returns for his businesses.

4) Being ahead of the curve
If Vaynerchuk has a superpower, it’s that he can spot trends early, allowing him to adapt his strategy accordingly. If you need proof, just look at how soon he created WineLibraryTV after YouTube’s launch! He was also among the first to leverage platforms like Snapchat and TikTok.

5) Putting value first
Wondering what ‘Jab, Jab, Jab, Right Hook’ means? This isn’t just the title of a Vaynerchuk book, but his approach to selling to customers; the jabs represent the value you provide to customers, while the hook is the ask. Simply, this means that you can’t ask your customers to do anything (click, buy, share) until you’ve delivered them value first, whether that’s free advice or entertaining content.

Gary Vee and the power of adaptability

The long and short of it is that Vaynerchuk is famous for being a great salesman; he can even teach you how to think like him for a price. If you’re inspired by Vaynerchuk’s story, here are four great learnings to take away:

1) Know when to adapt

Vaynerchuk stays ahead of the game because he understands the importance of adapting. In the 90s, his family’s business became one of the first alcohol brands to launch an e-commerce platform when Vaynerchuk ignored naysayers and embraced the power of the internet.

2) Take a no-nonsense approach to business

Vaynerchuk isn’t here to hold your hand while you worry about every little detail of your business. He just wants you to get started already! Vaynerchuk takes a no-nonsense approach to business and candidly discusses his perspective online, giving wannabe entrepreneurs the skinny on the realities of success; you must be prepared to work hard, embrace failure, and get out of your own way.

3) Master social media platforms

Building a personal brand relies on sharing your message with the right people. That means mastering the social media platforms your audience hangs out on, from LinkedIn to TikTok, and creating content tailored to each of these platforms and their demographics. Vaynerchuk’s is perhaps the best example of a personal brand that does this exceptionally well.

4) See kindness as a flex

The cut-throat #Hustle #Grindset mentality is often characterized by a coldness that leaves little room for kindness. But while Vaynerchuk has an aggressive communication style, if you look past it, you'll find empathy is central to his brand, as he sees it as an underrated strength essential to success in today’s self-centered world.

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