Gary Vaynerchuk: When business means “teaching”

Photo by Luigi Estuye, LUCREATIVE® on Unsplash

Gary Vaynerchuk is a serial entrepreneur and expert teacher who has used sharing his knowledge as a way to accelerate his career and goals. In the process becoming one of the most recognizable names on social media. 

Gary Vee is proof that instruction and teaching are lucrative endeavors for creators and that you can have success as a teacher regardless of the format you choose to sell your knowledge.

In fact, over his three-decade-long career, Gary’s used his knack for teaching to expand his creative and business ventures, something all creators can learn to do.

Gary Vee: Timeline As A Teacher

Gary Vee has been deliberate about where he chooses to teach and what mediums he chooses to use. You may know him from his many TV appearances or his YouTube videos, but his tenure as an online teacher stretches far beyond either of these. 

In fact, Gary Vee constantly finds innovative ways to use new media to build his brand online, his timeline as a teacher is proof of that.

Wine Library TV 

Gary Vee started teaching back in ‘06 with Wine Library TV. Five days a week for five years, he recorded and uploaded wine tastings, helping viewers find the perfect pairing. His energetic persona, coupled with his knowledge of wines, made him a go-to source for everything wine related. Because of Wine Library TV, his family’s online discounted wine retailer saw significant growth in sales. This early foray into teaching as a promotional tool to further his projects proved that Gary knew how lucrative the knowledge market would become.

Social Media

A year after gaining success on Wine Library TV, Gary Vee diversified to Twitter, giving information on topics other than wine and building a separate persona to the one he was building through Wine Library TV. Because, by now, he had successfully launched many projects, he also had knowledge others wanted about a variety of topics, topics that he, and his followers were passionate about. 

It’s something Gary continues to do as he uploads frequently to TikTok and Instagram.

$1 Million Book Deal

In 2009, Gary Vee solidified his position as an expert teacher by landing a $1 million, ten book deal with Harper Studios. At the time, the book deal was based on his growing social media following. He had grown his following to 145,000 followers in two years, presenting knowledge in the 140 character limit. By now, Gary was sharing his knowledge in blog posts, social media, YouTube videos, and now books. Frequently diversifying his methods of sharing his knowledge so he remained relevant, he expanded his readership and viewership, and he established his personal brand.

Weekly Videos

After ending Wine Library TV in 2011, Gary Vee made the successful switch to his personally branded YouTube channel. Although he had been posting on his own YouTube channel since 2007, after shuttering Wine Library TV, videos became more frequent and more produced on his self-titled YouTube channel. He became a popular teacher and instructor on YouTube in the entrepreneurship category, growing his channel to 2 million subscribers. 

The GaryVee Audio Experience

Now you can also get your dose of Gary Vee on his podcast, published through Anchor.

Like many of his other projects, Gary Vee saw an opportunity to expand his brand through the ever-growing medium of podcasts. He launched his podcast in 2016 and has successfully maintained his position in the top 100 global podcasts on Apple Podcasts. His weekly episodes also see him sharing knowledge – and inspiration – on entrepreneurship, goal setting, life improvement, and business.


Of course, after mastering every other method for sharing knowledge, it would only make sense for Gary Vee to also have his own course. Using Skillshare as his chosen platform for a traditional course, Gary teaches topics on two of his favorite subjects: wine and entrepreneurship.

What You Can Learn From Gary Vee

Gary Vee’s journey as a teacher reveals that you can have great success as a teacher on any platform and at any price. Whether Gary shares his knowledge for free – as he does on YouTube, his podcast, blog, and social media – or whether he monetizes it – through speaking engagements, books, or courses – Gary’s revealed the secret to success as a teacher is to go where your potential audience is.

Gary started teaching through YouTube, as he grew his following and reputation he moved onto premium content through books, speaking engagements, and courses. Throughout this time, he has also continued to find new ways to share knowledge like starting a podcast or uploading reels to Instagram or videos to TikTok. All of this helps him maintain his relevance while reaching a new audience and growing his existing one.

As a course instructor, there’s a lot you can learn from Gary Vee’s approach to teaching. 

a) You should always be pivoting your knowledge and skill so that you’re on the cutting edge 

b) You should focus on building your reputation with your audience by sharing knowledge through free sources like Medium or YouTube and then monetizing other sources like courses, books, and coaching. 

c) You should segment the kind of information you share on various platforms, making it easier to sell your premium content because users already know the kind of knowledge and information you have.

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