Executive Spotlight: Gary Vaynerchuk

Known for growing his family’s wine business from $3M to $60M in just 5 years, Gary Vaynerchuk was named the top CEO in the digital marketing space in 2018 by Brand24. Now, Gary is the CEO of his own digital marketing and communications company Vayner Media, as well as sports agency Vayner Sports. Additionally, he is a “prolific angel investor and venture capitalist,” investing in companies ranging from Facebook to Uber, a highly sought-after public speaker, and best-selling author. 

Gary, also known as Gary Vee, has no plans on slowing down. On top of all that, you may have seen him on your Twitter, Instagram, or YouTube feed, where he has a combined following of over 11 million people, whom he provides with “wake-up call” advice.

Often calling himself a purebred entrepreneur, Gary’s work-hard, play-hard attitude, and hunger for success are what make him appealing to younger audiences, business owners, and those who wish to live what he ultimately reflects: the manifestation of the American dream, as he is an immigrant of the U.S. from Belarus

However, one thing that Gary wants his followers to always understand is that putting in the work and being consistent is key, before even seeing or expecting results in one’s personal or professional endeavors. Before Gary Vee consistently went viral, he dedicated his time to filming wine reviews to increase the brand awareness of his family’s wine company.

In this Executive Spotlight, we take a look at Gary’s Youtube Channel, where it all started, and how he translates his wealth of knowledge and affable internet presence into video format, appealing to audiences across generations.


Video Length


While it is true that short, shareable videos are the secret to going viral and appealing to a broader audience, it turns out that more and more creators are entering the age of the hour-long YouTube video. Longer videos allow for YouTubers to appeal to their niche audience. For example, YouTube superstar Jenna Marbles went from sharing short 2-minute skits to videos nearing 20 minutes, which still garner views in the millions, because she has successfully built a niche fanbase over the past decade.

Gary’s YouTube videos range anywhere from 5 minutes to 3 hours, the shorter videos being quick, general lessons such as “When You’re From the Dirt And Still Like Playing In It” which include snippets of advice-giving phone calls with fans. These are often quick, easily digestible takeaways. The longer videos such as “How to Build Confidence and Self-esteem” are conversational videos, which are mostly watched by people who are already fans and willing to watch longer content, who then feel even closer with the real Gary by watching these more authentic conversations. By using a mix of short and long-form content, Gary Vee covers his bases: new fans find him accessible, and old fans feel even closer with him.

Thumbnails and Titles


When creating eye-catching Youtube thumbnails that will be clicked, there are several well-known best practices. This includes using bright colors, contrast and outlines, and text.

On Gary’s YouTube channel, his thumbnails are eye-catching with bright colors, and give off an authoritative tone. Many of the thumbnails and titles revolve around his popular segment, #AskGaryVee, where we often see Gary posing in a closeup with a special guest such as “Ask Gary Vee with Michael Chernow.”

Some of the more alluring titles that have garnered the most views are “One Life No Regrets,” “Ultimate Advice For Every 20 Year Old,” and “6 Mins for the Next 60 Years of Your Life.” Even if you don’t know who Gary Vee is, the titles of these videos pique the curiosity of viewers, suggesting critical, literally life-changing insider information that affect a specific amount of your life. These titles highlight an easy-to-understand value that can be gained from watching the video in a digestible amount of time. 

Consistency and Improvements


Keeping your format, schedule and content consistent is crucial, as it presents viewers with new content regularly, but also creates a content-seeking habit in the viewer so they know when to expect new content, which is why they originally subscribed. Establishing a posting schedule also builds credibility amongst subscribers.

The banner of Gary’s channel boasts “New Videos Every Day.” However, there are some inconsistencies in this schedule, and he frequently has gaps between his “daily” videos that can last as long as a whole week. This could contribute to the big differences between the view counts of his videos. For example, the video “No One Knew Me 10 Years Ago,” and the video “95% of People are Confused About Success and Happiness,” which have a difference nearing 300,000 views. Gary has the potential for huge views on his videos, but he can garner even more views by adhering to a stricter posting schedule.

In a digital era where videos are becoming increasingly important for content marketing, Gary Vee has established himself as a thought leader, encouraging young entrepreneurs to challenge the status quo. With his real-life advice, he doesn’t shy away from giving his honest opinion and advice to his followers, which in turn contributes to the authenticity and transparency of his business. His influence extends beyond young entrepreneurs seeking advice to general success in life, but also to those who wish to challenge themselves in their everyday lives. 


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