Gary Vee’s $100 Million Dollar Genius Brain + His Entire Playbook

Gary Vaynerchuk. Gary Vee. Gary V. Whatever you call him, he’s one of the most influential social media personalities of all time.

His myriad accomplishments include:

  • Author of 4 best-selling books – Crush It, The Thank You Economy, Jab Jab Jab Right Hook and #AskGaryVee
  • Founder of Vaynermedia. Grew it from a modest beginning in 2009 to a massive team of 750 and gets $100mn in revenue with bigwig, Fortune 500 clients like Budweiser, Coke.
  • Early Investor in Facebook, Uber, Twitter, Snapchat, and Tumblr.
  • Also known as the ‘wine guy’. He grew his dad’s humble liquor store to a massive wine empire via digital marketing.

A media mogul, a serial entrepreneur, and a motivational speaker; he’s a pretty big deal in the online world and has a massive audience. In almost 14 years, he’s gone from Gary-who to GARY VEE.

He’s more popular than Jesus, at least on most major social networks:

  • Facebook – 2,907,674 likes
  • Instagram – 3.8 million followers
  • Twitter – 1.69 million followers
  • YouTube – 1,516,636 subscribers

The secret behind his stupendous social success? He’s a student, and he’s studying the science of social media.

When people think about Facebook, Twitter, Tumblr, Pinterest, Instagram—all those platforms—they just see a lot of noise. They’re not sure what social media is, and they don’t think it really sells stuff. When I think about how to sell stuff on social media, I see a science. I see a science of what time to post, which picture to post, and how to post. Do you need a full graphic? Do you need to do a video or pictures or written words? Do you use a hashtag? It’s a science, my friend.  –Gary Vaynerchuk

So let’s dissect his social strategy and see how he reached so far.


Gary Vee’s $100 Million Dollar Genius Brain + His Entire Playbook



Content on Content on Content


Gary publishes a lot of content every single day – around 6 to 8 posts on each of his social media profiles. Every time you log onto Instagram, Twitter or open your Facebook news feed, you’ll see a thought-provoking update by Gary V.

So, how does he create so much content?

Through his ‘content on content on content’ strategy.

‘I create a ton of content. I publish a new episode every day on the GaryVee Video Experience, which is distributed on my YouTube channel, Facebook Watch Page, and IGTV. I then also have a daily podcast called the GaryVee Audio Experience, which is distributed on my iTunes, Overcast, and Stitcher, amongst some other platforms. In addition to what I just mentioned, I continually post “micro content”, that is distributed to my Instagram, Snapchat, LinkedIn, Quora, and many of my other social channels. “Micro content” is created from each episode and is used to drive awareness back to the original long-form content. Long story short, I am constantly creating and posting as much content as possible and in a way that is contextual to each platform.’

It’s a brilliant strategy that helps you create a constant stream of social content by using one long-form pillar content.

His 16 person team turns one of his pillar contents – from his daily vlog DailyVee, #AskGaryVee show, podcasts, or his keynotes and interviews – into around 30 different smaller social media content pieces. This includes short videos optimized for specific social platforms, picture quotes, Facebook textual posts, GIFs, IG stories, SnapChat, and so on.


Here’s a short example of how he creates a plethora of social micro-content (mainly for IG and FB) via one pillar content.


1. It starts with 1 long-form piece of content – like this keynote from 2017.


2. Next, his team sliced this video up and edited them into lots of short videos for his social media.

For Facebook, he created 1 to 3-minute long square videos (optimum for Facebook video content) highlighting specific topics and uploaded these videos over the course of a few months.

Doing The Right Thing Is Always The Right THing

Make me a promise. -When you see the opening to do something nice or special just because you can and expect nothing in return for it PLEASE ACT! -Tag your best friend -I ❤ you Guys.

Posted by Gary Vaynerchuk on Thursday, November 9, 2017

Notice how he doesn’t upload all this microcontent at once. He mixes it up with other content so that it doesn’t look like he chopped up his keynote and put it up on social media to fill space.


THIS IS THE GREATEST ERA IN HUMAN HISTORY!!! ?❗️?❗️? what are u #grateful for?? Who do u know that needs to see this … show them <3 ??

Posted by Gary Vaynerchuk on Tuesday, October 24, 2017

He also doesn’t just upload these clips. He adds personalized captions to each of these videos to further optimize them, along with subtitles because remember ‘85% of Facebook video is watched without sound’.

For Instagram, he converts facebook clips into Instagram videos (shorter, more impactful), and adds them to the upload queue.


He doesn’t use the same caption he used in his Facebook video post. He creates a new caption for his IG video posts because he’s addressing a different audience. So while he’s reusing a lot of old content, he’s also simultaneously creating brand-new content. A mix of both old and new gets these crazy results.

He prompts action on his IG posts by usually adding a simple CTA like ‘Tag XYZ’. Yup, that’s it. Since his posts are generally motivational in nature, a simple CTA that asks people to share Gary Vee’s wisdom with friends works great.


3. You see all these amazing quotes that Gary shares on his profile and wonder, damn, how does he come up with all these quotes?

Over a 100 people (on average) engage with his video and most of them point out parts that moved them the most. His team then turns those statements, and other similar, impressive snippets of Gary V into motivational quotes with simple graphics.

This keynote went on for over 2 hours, so Gary V said a plethora of things that could easily be turned into quotes and uploaded on IG.

Lesson learned?

Listen to your audience. See what they have to say about your content. And then use that knowledge to further create simple content pieces that you know will resonate with your audience.

As Gary says,

“When there is an ongoing conversation about your brand or product or service, good or bad, and you aren’t a part of that conversation, that’s a huge blown opportunity”.


4.  He’s not done. Yet.

He further cuts down these video clips and uses 15 most impactful seconds of it on his IG stories, adding a swipe up option to send people to his original content.

This is a teeny, tiny example of his content on content on content strategy. His team does this to every pillar content he creates, which results in hundreds of meaningful social posts to upload every 6 to 8 hours.

(if you want extra credit, you could experiment with repurposing some of your video in Facebook video covers)



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Document. Don’t Create.


Gary V reached crazy heights of social popularity because of several reasons. One of the main ones is the amount of content uploaded every single day. If you’re following him on social media, you’re bound to come across his social updates at least once every day.

So apart from creating content from content, what other strategies help him accomplish this mammoth task?


Documenting his life in an informal manner via Facebook and Instagram Live.

‘If you want people to start listening to you, you have to show up. Too many “content creators” think that they only have one at bat—they have to make the one, most beautifully created video or image or rant on Facebook. But what they don’t realize is that their hunger to make the perfect piece of content is what’s actually crippling them.’

He routinely does Live Q and A’s, influencer interviews, and off-the-cuff rants. Informal, aggressive, motivational. He stays true to his signature style and delivers compelling content ad lib.

His advice to you,

‘When I say to put out those 6-7 meaningful pieces of content a day, just pick up your smartphone, open Facebook Live, and just start talking about the things most important to you.’

He’s also a huge fan of IG stories and uses it every single day, without fail. He uses it to show his personal life, to promote his vlogs and blog, show behind-the-scenes of his shoots and office life and also offers his audience a huge selection of motivational screen-savers.

According to Gary V, Instagram stories is one of the most useful (and under-utilized) social marketing tools out there.

So, if you’re running short on content, don’t spend all your time creating that perfect video. Sometimes, it’s cool to just sit and talk to your audience, even if it’s for 2 minutes. This also comes under the umbrella of ‘creating content’.



Be a First-Mover with Every New Feature


He’s eerily far-sighted. Always the first to experiment with new features, tools, platforms, and pretty much anything that comes out in the digital marketing world, he’s a super-successful social media gambler. Listed below are just a few of the many, many things he’s dabbled in.


Cover page video, Instant articles, and Page stories

Facebook rolls out new updates fairly regularly. While some feature dies a natural death, others become a vital part of this popular platform.

Seeing as we’ve already entered a video-first world, replacing static images with the video was the next obvious step.

When Facebook introduced cover videos, Gary immediately jumped on this bandwagon and uploaded an excellent cover video. This 41-second video with graphics inlays instantly captures attention, boosts engagement (over 200 comments and counting), and is an amalgamation of everything he stands for.

Posted by Gary Vaynerchuk on Friday, August 11, 2017

After Instagram, Gary’s also reigning over Facebook Page Stories. Even if it’s just putting up a screenshot or a post he’s previously used, he will regularly update his Facebook page stories.

With the advent of Instant Articles on Facebook, a feature where page owners publish articles, Gary V used it to promote his older blog posts. And since Facebook reports that an Instant Article is 20 percent to 50 percent more likely to be clicked than a regular link post, it’s a great marketing tactic to promote your old content in front of a new audience and reach out to a wider audience base.



Instagram TV

As soon as Instagram launched its TV, aka IGTV, Gary obviously started creating content for it on. He had a video up the same day!

And his video content on IGTV is bang on.

He understands the different requirements of different platforms and the audience that’s watching it. IGTV is the hottest video feature to hit D-town and Gary knows the key to use IGTV to its utmost potential is to constantly experiment and constantly update.

So he usually repurposes and edits his keynotes, and puts it up on IGTV.




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Extra: “First in Line” text messaging club

Is there anything he hasn’t dabbled in? I think not.

The man is everywhere. Even in your iPhone contacts.

This is what First in Line’s all about.

People don’t read every email they get. They don’t read every Instagram DM, or Facebook Message. But they do read their text messages. Texts still dominate people’s attention. So text is one of the places Gary wants to be.




1 on 1 Communication at Scale


How do you grow your community?

“Content and context. Putting out hardcore content, as much as possible, and then ENGAGING. By engaging (replying, answering questions, CARING BACK) you create context. But don’t get mistaken: you will need to bring hard work in to the community. Only 1% of people get it just by the content pushout.”

His entire social media strategy revolves around providing epic content and engaging with the audience. While initially he directly interacted with his audience, now that his brand has grown substantially, his team caters to his audience.

“If you grow and make or raise money, take some of that money and will apply that to hire more human beings that can do more engagement and intimacy. The question is… are you willing to make the commitment to allocate dollars to humans?”

Let’s discuss some of what he does to keep his tribe happy.  


$1.80 strategy

According to Gary V, this strategy asks you to,

‘…leave your personal .02 cents on the top 9 trending Instagram posts for 10 different hashtags that are relevant to your brand or business every single day.  By the end, you haven’t just left your .02, but a full $1.80 of thoughts online in the specific category, niche or industry you want to become a part of.’

This is what he did when he started out. Nobody listened to his YouTube show for over a year, and he barely had any followers on Instagram when he started. Through this strategy, he built his (and all the other big and small brands he works with) social following to where it is now.


Built his tribe on Facebook through a high-engagement group

Facebook pages organic reach and engagement are dwindling rapidly. His Facebook group ‘First in Line with Gary Vee’, is his attempt to beat Facebook’s latest algorithm changes and engage the audience via FB’s group feature. However, unlike other Facebook groups started (and then abandoned midway) by marketing mavens and bigwigs of different industries, Gary’s group is bursting with engagement.

And how does he keep conversations flowing and genuine engagement mounting in his group?

  • By uploading video messages especially for his group members periodically.
  • By appointing an admin who’s constantly active on this group and multiple moderators who make sure this group is a positive, thriving group. His team ensures that everyone’s queries are answered, updates regarding Gary V and his projects are made on time, conversations flow a lot easier with them pitching in with valuable advise, introduction posts are frequently made to welcome new members, and the list goes on.

  • Conducting multiple contests and competitions on this group to further engage his audience.


Has multiple FB pages and IG profiles to accommodate his audience

With over 3.9 million followers, an average of 100k likes and 3000 comments, somebody needs to respond to a plethora of comments. For this purpose, Gary V has a separate account dedicated to engaging and responding back to the audience – Team Gary Vee.

To cater to his international audience, he created several Facebook pages in different languages, such as Gary Vee Chinese. The best part about this strategy is that unlike other people he doesn’t create a new Facebook page, uploads enthusiastically for a couple of days or even months, and then leaves it to die.

He works really hard to create a safe haven for his audience. For example, for this page, he made sure to upload a video with Chinese captions, create posts in Chinese, and speak to his audience in their language. This is what gets him those extra brownie points.

And his hard work pays off. His audience enthusiastically responds to his posts and engagement is super-high on these pages, as well.

The same goes for all other pages he’s created for his international audience.


Constantly asks for feedback from the audience

What? Gary Vee knows it all, he doesn’t need to ask his audience if his content is hitting home.

Or does he?

A successful entrepreneur knows that the concentration span in the digital world is dwindling. Unless you keep your audience entertained 24\7, they’ll ditch you for another similar motivational speaker, social media maverick, ‘guru’, etc.

Asking audience periodically if they’re happy with the content published, or what kind of topics they’d like to more frequently discussed has two benefits – 1) it gives you an insight into what your audience wants and what they think about your content, 2) makes your audience feel special and included.

Gary V does exactly that.



Attitude is Everything.


Too many people are giving up. They give up because they “follow analytics” and didn’t see growth for six months. Stupid. You wanna build big businesses, it takes time. – Gary

Give it time. Create content. Use the science of social media. Experiment. And accept the fact that you might fall 100 times. But don’t’ let that be the last fall. Be consistent in your efforts and keep your mind on the end goal.

If you watch his social, Gary spends most of his time preaching the merits of positivity and hard work. That’s not accidental. Anyone can teach you tactics. (Hey, we tried with this long article.) But tactics aren’t permanent. Mindset is.

So stay positive, keep grinding, and don’t forget to enjoy the ride.



If you’ve read this far, thank you so much for your time. It really does mean a lot to me. I hope this article helped you in some tiny way and if it did, please share with a friend that also loves Gary Vee.

Thanks for reading ❤

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