The Master Plan of Gary Vaynerchuk

Whether you love him or hate him Gary Vaynerschuk is an impressive business man. He is best known, admired (and equally reviled) for being the icon of the “Hustle Porn” & Inspiring the Wantrepreneur.His image, videos and quotes can be found all over social media. He literally is a Media Company of One. 

Myself, being a San Francisco-based tech guy, it has been eye-opening watching his rise in New York,  then globally over the last decade and half. I’ve read all his books, impressed by his insights in where the media world is going and how to build a business on top of it. His emergence as a big business “influencer” (yes, I hate that term too) is not just emblematic of the tech driven economy. But I strongly believe his path holds great career and business lessons for all of us. 

His Backstory

I think everyone knows the story of Gary Vee as he is known to his followers. He took his dad’s offline wine store, Wine Library, online and using social media grew it from $3M to 60M in revenue. But people forget he had an email list even back in 1997. So Gary was at the very beginning of the internet and the growing community online. 

 He wrote a book in 2009 called “Crushing it” detailing how he and others leveraged social media to build some very successful businesses and lifestyles. This was the first of 5 New York Times best selling books over the last decade. 

He parlayed this into angel investing, investing in Facebook, Twitter, Tumblr, Uber, Snap & Venmo. He also leveraged some of the consulting he did for big Fortune 500 clients into building a new media focused ad agency called VaynerMedia. An agency now estimated to be billing 200M usd annually. 

He has built some adjacent companies in the conference business, a new VC fund called VaynerRSE and a personality-driven media brand around himself. He does a lot of public speaking around the world either on digital media strategy or entrepreneurial motivation where he charges $120k usd per talk (+ expenses). 

He is the master of building a personal brand online, with more than 12M combined followers across Instagram, Youtube, Facebook, Snap, Twitter, Linkedin & Spotify. He is so omnipresent, I doubt anyone on these channels have not run across him. 

Why Gary Vee is the ultimate example of a Practitioner Preacher. 

So what are the things we can learn from Gary Vee. 

He leverages every single facet of his business as inputs into something larger. By leveraging his knowledge in social media marketing, he built a business from public speaking and then from his first  book. 

Two very clear examples: 

1) Personally consulting large fortune 500 brands to building the Vayner Media agency to serve them

2) Angel investing personally to building a VC Fund 

Here’s what Gary Vaynerchuck is really up to with that new $25M fund (exclusive)


Once he had structure, he built out a media company around him. With the infrastructure of his team and personally practicing live, he is on the literal edge of where the media is going. He is able to notice new channels or best practices which he pushes out to clients or his followers. This back and forth of doing, learning, sharing & feedback and doing, learning, sharing & feedback is an amazing flywheel. Concepts - The Flywheel Effect


There are very few people in the world today that have his deep insights in how to leverage social media to build a massive business. Ie. Network effects & his organization has built a bastardized version of the “Expertise Network Effect” popularized by renowned VC fund NFX (Source: The 14th Network Effect: Expertise)

“The two key distinctions of expertise nfx from other types of nfx is that a) they arise from the know-how required of a person to use a particular tool and b) the value transfer mechanism takes place through labor markets.

The results speak for themselves here which shows a full rundown of his very impressive net worth & assets. 

Gary Vaynerchuk Net Worth and How He Built His Fortune


Some insights he shared in this recent video interview illustrate this perspective. These quotes below are just some nuggets of insight for those trying to keep on top of the every changing media landscape. 

Source: Why Gary Vaynerchuk is 'winning' the marketing game


“Understand where People are paying attention:, I am unemotional about platform, but emotional about where consumers have attention”


“It’s the Message, not the medium”


“I’m a Day trader of where communication is, not a mutual fund of where performance was”


“Completely Platform agnostic”--really critical in fast moving media & consumer behavior changes.


“All i do is pay attention to what people are doing”


Key Lessons here: 


  • Be Prepared to Hustle BUT ….make sure it’s something you have passion in or deep personal interest in. Basically, work hard to win but make sure it’s a game you actually want to win. 


  • Own a Niche & Build Deep Expertise: The more narrow the better. With billions of people there will be an audience and sometimes all you need is 1000 raving fans as per Kevin Kelly. The Technium: 1,000 True Fans


  • Practice and then Preach: Nuff said. This is the only way you can develop the expertise and credibility. 


  • Be a Strong Personal Brands matter. Okay to be Divisive: it attracts & repels at the same time. 


  • Leverage Platforms but be agnostic: You should always be Audience first. Pay attention to what people are doing and where consumer attention is. 


  • Step Ladder your initiatives from micro to macro and unify them for your own Flywheel: Think of yourself like a business (literally) and see how the different initiatives tie together and build on one another.

  • Build Equity. 

Equity=True Wealth. “You must own equity — a piece of a business — to gain your financial freedom.” —Naval


What are Gary Vee’s Future Plans: 


He is taking his platform even further. He has often publicly expressed his end goal of buying the New York Jets. An NFL team these days costs at least a cool $1 Billion usd. 

As wealthy as Gary is with his stakes in VC fund & VaynerX he still has to supersize his fortune to get to the Billions (or even multi-hundreds of millions). 

I believe his playbook to do this is by entering the Consumer Product Goods (CPG) game. He can leverage the massive audience platforms he has built already.

Step One: 

Testing this via the shoe deal he did with K-Swiss.

Serial Entrepreneur Gary Vaynerchuk Just Landed a Sneaker Deal. Here's Why That Matters

Why Gary Vaynerchuk Is Putting His Name on a K-Swiss Sneaker


Step Two: 

As K-Swiss deal clearly shows he has an audience to successfully sell into. Next up, taking equity stakes in emerging Consumer brands or starting a fully owned Consumer Packaged Good (CPG) business. He wins big when they exit in an acquisition that many of the big traditionally CPG companies are now pursuing as their growth is lagging. Mergers and Acquisitions have been very hot in the CPG space in the last half decade. Gary recently sold his “Empathy” Wine brand to Constellation Brands. 

Constellation Brands acquires Gary Vaynerchuk's Empathy Wines


Step Three: 

Scale up and buy a bunch of BIG and old CPG Brands. VaynerX is going to be his media platform to grow the Brand and audience, thus increasing the value of the company (and his stake). 


“Vaynerchuk says building an agency was never meant to be anything but a means to an end, facilitating the necessary learnings and expertise to reach the real goal: owning brands. "I’m building a communications holding company for the sake of buying businesses and using it as a disproportionate leverage for the reboot of nostalgic brands during the next downturn of the economy.”


“For a long time, he thought he’d buy an old CPG brand, the sort of food brand you remember lovingly from childhood but that now sits gathering dust on supermarket shelves. Now he’s more interested in apparel. He’s had some success with niche sneaker brand K-Swiss, which collaborated with GaryVee on a range. And he’d love to get his hands on a brand like Lacoste.

“So when I do go and buy something – in three years or six years – I’m not going to shut down VaynerMedia. I haven’t bought any brands because I don’t want to buy them at the prices they are now. But that’s still the plan. It’s not part of the plan, it’s the plan.”

The GaryVee Content Strategy: How to Grow and Distribute Your Brand's Social Media Content

Is Gary Vaynerchuk 'wrong, wrong, wrong, wrong, wrong' about media?


We all have much to learn from Gary Vee’s career so far, which provides valuable lessons for building a business. This is relevant whether you want to build a multi-billion dollar business or a small one person business that gives you a very comfortable living. 

Like most things in life, all the steps seem simple, but not easy to do. It’s now just a matter of motivation and taking action. So with these steps and a clear playbook available, the big question that Gary Vee would ask you, “How Badly Do you Want it?”


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