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Gary Vaynerchuk: Definitive Guide to PR and Marketing For Founders and Entrepreneurs

Gary Vaynerchuk initially came into fame for taking over his father’s wine business valued at $3 million and growing it to a $60 million company. Born in the Soviet Union, in a country now called Belarus, his family immigrated to the US in 1978 living in New York then later moving to Edison, New Jersey.

After taking over his father’s wine business in 1998, he started an e-commerce branch for the business, and changed the business name to Wine Library. At the time, he had become fascinated with the power of the internet and was excited to take the wine business online. He created one of the very first wine-based YouTube channels where he produced videos and content to drive sales to the Wine Library online store. That was in 2006. 5 years later, the Wine Library TV had over 1,000 episodes and thousands of hours of video.

At the same time, he started Vaynermedia in 2005, a digital marketing agency focused on helping brands get discovered and known by people through content creation.

The knowledge from growing Wine Library’s customer base through content and pricing helped him start his own agency as a show of proof of his abilities.

Forbes estimates his current net worth to be around $160 million. His company, Vaynermedia now employs over 600 creatives and story tellers.

Gary leverages content marketing and the rise of social media to not only grow his personal brand but also get brands known around the world. His knowledge in this verticals is well sort after. Now, aside from running Vaynermedia, he speaks in various public conferences around the world. For startups and entrepreneurs, he is a thrill, mostly because he says it how he sees it. Even more so because he has helped brands turnaround their ways of doing things from his massive experience and scintillating talks.

For startups, the amount of learning that you can get to do from Gary Vaynerchuk alone is no doubt humongous; which explains why he features in our series of entrepreneurs who can teach startups something.

Content Marketing

Gary has produced enough content on the internet and in real life to know what moves faster. He is all about speed; and it is not a secret that startups today are seeking to scale faster than any generation of companies before.

His concept is called the Content Pyramid.

The Content Pyramid

One piece of long form content becomes the centre stage from which several little pieces of content are derived. The little pieces of content could be in form of memes, images, videos, GIFs, mashups, stories, remixes, rants, and quotes.

The idea here is simple and can be described as follows:

Document >>> Create >>> Listen >>> Create >>> Distribute

It is a loop going from Documenting to Distribution and here is what happens in each of those stages:

Document: In this phase, you create the major cornerstone piece of content. If it is a video it could go on for hours. If it is an article, the limit to the number of words can only be set by you but longer is better. The same goes for podcasts.

Create: Once you have documented the long form content and posted it on one platform – could be your channel or blog – you go to the next phase of create multiple pieces of little content from the pillar content. This could be in the form of videos, images, rants, short podcasts, remixes, shorter articles, videos, quotes, images, memes, or GIFs, etc.

Distribute: These little pieces of content are then distributed to all social media networks from Facebook, to Twitter, Pinterest, YouTube, Instagram, etc. You also get them onto platforms like Quora, LinkedIn, and Medium among others.

Listen: Now is the time to pause your content production and listen to what your audience is saying. This is feedback regarding your now distributed content and the cornerstone piece posted on your channel or blog. There are several ways to listen but one of the most important is comments and reactions to the content. Some platforms which enable users to upvote or downvote content also allow you to follow the best performing pieces. Platforms like Facebook where users can share the videos, like, or comment on them help you to know what your audience perceives about the content.

Create: Take all the insights collected from your listening and use to create more little pieces of content for your audience. The listening part was integral because if you were keen, there, your audience told how to get them sharing more, commenting more, engaging more, and bringing your brand to the world using the content they liked. From memes to GIFS, videos to podcasts, quotes to articles, the data you collected has all you need for your content marketing success. Gary calls this community-driven content.

Distribute: Again, distribute your community-driven content across all social media platforms and content-based sites like Medium and Quora.

Using the content pyramid strategy, Gary was able to get 35 million views in total on all his little pieces of content based off this cornerstone video.

5 Important Traits of an Entrepreneur

Salesmanship – Knowing how to make a sale is Gary’s most important trait. If you cannot successfully sell something, then entrepreneurship cannot possibly be your forte. Whether it is a physical product or a service, your selling capability defines whether you will be able to make the first sale and more, or not.

Something to prove – If you were born and grew up in a background of poverty, you might be driven by the desire to change that and make a better life for yourself and your family. If you were born in a rich family, people probably think you are a spoilt brat. However, if you do not want any part in your family’s riches and would like to form your own path and be self-made, then it becomes another driving force. The bottom line is that you need a driving force, and it mostly has to be related to personal experience to be a driving force enough.

Independent spirit – Do you rely on your own decision making or are you one to make decisions based on other people’s choices? If you are independent in making decisions and taking chances, you are more likely an entrepreneur by heart as compared to people who just follow where the wind blows.

Understanding consumers – Gary gives an example of Mark Zuckerberg as one entrepreneur who has instinct when it comes to understanding what direction consumers are moving in. When he saw that photos were becoming a proper thing, he acquired Instagram before it got to half a billion users. He did the same for WhatsApp upon realizing that messaging through the internet is becoming crucial and so many people were conducting business through the app. An entrepreneur has to be able to read the market and know to which side they are moving.

Patience – Unfortunately, entrepreneurship is not an easy road. Everything takes time. Years and years of commitment will finally give you the much needed success. If you are not a patient person, you are most likely to give up way earlier along the way. Being an entrepreneur is all about patience and believing in the process, eventually, it all works out.

Having defined the traits of a successful entrepreneur right from Gary’s playbook, it is time to focus on the public relations and marketing guide according to Gary:

1) Be practical with your money

In the age where startups are burning through money like no one’s business, and so many founders are focusing on the next seed round rather than turning a profit, entrepreneurship is slowly being watered down to cheeky and blissful tactics. Gary disagrees on this way of doing startups.

Startups need to treat their money practically. How much do you spend? How much do you make in return? What is the loss? Or what is the profit?

At launch, you need to focus on income generation and turning profits. While venture capitalists have given so many Silicon Valley entrepreneurs cushion from necessarily generating revenue and making profits, not so many entrepreneurs have that advantage. You cannot run a business that is not making money and then expect to get some venture capitalist who wants to heap a million dollars on you – at least not in most parts of the world.

Entrepreneurs need to understand the real cost of the business, and it won’t come if you are burning $150,000 a week. You have to know how much from your capital is left to run your business and how long you can stay afloat. It is about being practical with your money.

This allows you to build up the real muscle for your business to generate revenue. The good side is that you are generating revenue and making a profit from day one. If you keep growing it is always on the profit basis. The growth is organic and slow by slow you get to the goal. Additionally, you won’t need investor funding and you won’t have to sell your stake. Your company won’t need to shift its goals, mission and vision, to fit your investors.

2) Commit, commit, commit

Gary talks about how much time he had to commit in the first year to get all his ventures to take off. Commitment is unquestionable in an entrepreneur’s world. Your commitment is probably what will keep the business afloat way after the motivation and initial excitement wears off. Putting in the hours everyday.

3) Keep your word

When he started selling wine in his father’s business, his dad told him that if he ordered for 500 bottles of wine he couldn’t cancel on the order a day before because then he would have to drink all those bottles. The cost to the business would be dire.

You have to say something and follow through. You will build on your personality. You will grow to become a reputable entrepreneur. Promise to meet a deadline, and do everything it takes to meet it. Go through lengths to build your company in all honesty and discipline. This makes a person.

Your previous clients will only refer you if they can vouch for your dedication to make your word your bond.

4) Start hustling

Many people get ideas, some very worthy of following through. However, most of them just sit back and hope they will get time to start working on those ideas. Sadly, people like those achieve nothing of the ideas.

Actually do something. Start hustling.

Get up from your bed every day and put in a shift on your idea. Leave your commitments that take so much time and start building on that dream. The only entrepreneur that achieves their dream is the one who is actively working on it.

5) Do not do it to buy stuff

We all want fancy cars, jets, houses, and posh lifestyles. But do not get into entrepreneurship for that.

The goal has to be bigger and something more worthy that will push you from your comfort zone every day to actually doing something.

Gary can afford all these things, but he says he didn’t become an entrepreneur because of that. Material desire has never been his driving force. Don’t let it be yours because it is so temporary.

6) Zero entitlement

No one in the world owes you a purchase for your product. Same as the old good statement of “the world owes you nothing.”

And it is true.

If you are getting into entrepreneurship, understand that money won’t come easy. No one will give you their money just because you wake up every day and work 18 hour shifts.

You see, that is a good thing.

When people owe you nothing, they tend to somewhat underestimate you.

You are building something from scratch of which no one can see the goal except you. Therefore, most people will either not understand your vision or they won’t believe you can make it.

Gary moved into the digital agency market when no one knew him in the space. Well, he had helped scale his dad’s wine business but that is all the experience he had. No client. No connections in the industry. He says it excited him because nobody thought he would build a successful agency. That lack of entitlement helped him push the boundaries from the very first client to the next one.

7) What is the legacy?

Does your business have a vision of what it wants to achieve? What problem is being solved? What legacy do you want to leave behind?

Gary says he always worried of how he will be looked at in the long term. So it helped him stay on track to remain disciplined in his dealings.

You might do something for the short term gain but it jeopardizes your business in the long term. Endlessly worry about your legacy. Worry about the stories that will be told in books or blogs about you. Image is important. Even online.

8) Always be on the offense

Never allow yourself to be caught out in the defense as an entrepreneur because that means you are now playing catch up – you are not the lead in your field.

Always move with speed, be on every social media channel before you competitor gets there. Innovate and stay ahead of the game before your competitor knows it. Lead the pack. Always win.

The thing about business is that if you let your guard down and begin to chase the pack, you might be lagging behind forever. Don’t allow that.

9) Do not bother about what your parents or teachers think

Sometimes people are used to living the same life they have lived. They do not want to try something new. They are in a state of comfort because everything works just fine at that point. Entrepreneurs hate being “just fine” and sometimes our parents or teachers might not understand. They might criticize or shut your entrepreneurship dreams down instead.

Don’t listen to them. Just go for it. If you fail you learn, and go on to the next idea. If it works out, you win.

Also, just because it might fail doesn’t mean you don’t try it or that you are wrong.

Some of Gary Vaynerchuk’s quotes have been shared widely across the internet. Here are some you might enjoy;

On Winning

Winning is not defined by me or by your parents, or even the market. It is defined by you.

Losing your focus?

I don’t give a fuck what anybody else has. I’m focused on my shit. Start focusing on your shit.

Actually do it

If 1 out of 15 of your ideas succeed that’s better than 99% of your friends who never start a single idea.

On sleep

It is not about how much sleep you get. It’s about what you do when you are awake.

The rough road

Eat shit for 24 months & eat cavier for the rest of your life.

Take the shot

Roll up to that attractive woman in the bar and ask her out. Roll out on that good looking due and ask him out for coffee. Roll up on your business idea and make it happen. Because being 50, 60, 70, 80, 90 and regretting that you didn’t swing that bat is the worst regret of them all.


Work. That’s how you get it.

Move on

Forget yesterday, last week, last month, that girl, that boy, that boss, that time. Let’s fucking go.

All this looking back is fucking with your neck.

Most people lack the skill or ability to build multi-million dollar businesses. Entrepreneurs find a way out. It is not the value of the business in monetary sums that is important, it is the impact it creates in society. Impact has to shape society, and that was left to entrepreneurs to do; the risk-takers.

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