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How @GaryVee Built His Twitter Following & Social Empire In The Early Days


This is Gary Vaynerchuk’s first tweet that he sent out back in May 2007:

Even in the very beginning, Gary was grinding it out.

People look at Gary Vee, as he’s more commonly called, today in awe and admiration. They look to him for advice on marketing, entrepreneurship, self-awareness and building your own brand. His word is held to the highest degree.

So, how did he do it?

Well if looking at that first tweet is any indication of how he “did it”, I’d say it’s quite obvious.

He worked for it.

10+ years of hard work, to be specific.

The level that Gary Vee has reached in terms of success and following doesn’t happen overnight, although many would think it does. If you look at the average engagement of his tweets around the time of that first post, and even in the few years following it, there’s not much that would indicate he’d be the social media powerhouse that he is today.

Even taking a look at this YouTube page, you see a stark contrast from then to now. His earliest YouTube videos, uploaded some 10 years ago, average about 9K views (probably many of those views accumulated over the years) — still, not bad!

But those today, well they garner an average of 50-60K views each:

He may not have had many conversations back then— many likes, views or retweets—  but his efforts never wavered. He still continued to post and create regardless of who was listening.

It’s called consistency.

And this clip summarizes that quite well:

Gary isn’t qualified to talk about personal branding because he holds a masters degree in the subject – he is qualified because he practices what he preaches. He’s dived in head first from Day 1 and has built a personal brand by documenting his process and learning along the way.

Today, with over 1.1 million subscribers on YouTube, 1.6 million followers on Twitter, 2.6 million likes on Facebook and 2.9 million followers on Instagram, he can’t release a post on any platform without receiving hundreds, if not thousands, of likes, views, shares and comments.

He could write a digital marketing course curriculum, and this tweet, posted 3 minutes ago (at the time of me creating this post), already has 54 likes, 5 comments and 8 retweets:

That level of engagement comes as the result of hard work.

Building trust. Building a tribe. And yes…

Consistency and persistence.

As I will highlight throughout this blog post, these two words are some of Gary Vee’s core principles. He may not have had a plan to become who he is today, but he had a vision and he submitted himself to the process.

So where did this dude come from and how has he achieved all that he has so far?

To answer that question, we’re going to dive in and examine the social media, marketing and branding strategies that Gary Vaynerchuk has embraced, from the early days to now.

Let’s get to it:

Starting With Gary Vee’s Humble Beginnings

Gary’s journey to the marketing pro he has become today started not long after he and his family immigrated to the United States. They moved to New York, escaping Belarus and the former Soviet Union, eventually settling in New Jersey.

In New Jersey, Gary’s dad worked at a local wine store owned by a relative. Young Gary started to catch an entrepreneurial bug of his own pretty early on. One of his earliest “ventures” was taking his neighbours flowers from their gardens and selling the back to them. If that doesn’t scream natural salesman, I don’t know what does!

From there, he went on to manage his own chain of neighbourhood lemonade stands and sell baseball cards, all before hitting high school.

And then came THE INTERNET.

At this point, Gary was in college and had been working for a few years with his father at Shoppers Discount Liquors (which their family now owned). He had already developed an interest in the business, having taken the time to learn all he could about wine and how their customers interacted with it. When the internet came along, he took what he already knew about people’s buying behaviours and figured out how he could market his family’s products on a larger scale.

Gary’s dad gave him the reigns to do some rebranding and he developed a new website, Fast forward to 2006 and the development of his vlog, Wine Library TV, on the one-year-old video platform at the time called YouTube. This was Gary’s first foray into the world of content marketing.

Check out Episode #1 of Wine Library TV:

What stands out about this?

Well, it’s nothing fancy— like truly, nothing fancy. It’s a regular office with a plain desk, poor lighting, no editing… but he’s doing it! He is just doing it, and that is something that differentiates him from a lot of people.  

He talks about this a lot to this day because he knows many people feel like they need to have every detail perfected before they launch or start something new. Sometimes you just need to put it out there and make adjustments along the way.

The Lead Up To Becoming The Gary Vee We Know Today

Gary knew he and his team were onto something as some of the first to explore vlogging in the wine industry. He didn’t go into this expecting dollars to come shooting out of the camera, but rather he used video as a way to communicate with his audience on a different scale.

He used this platform to build his reputation and his authority on wine, educating customers and building a loyal following along the way.

Something worked because just a year after he launched Wine Library TV, Gary Vee found himself taste testing wine with Conan O’Brien in his first appearance on Late Night:

And here’s what that something is:

1) A unique approach to storytelling:

As he told the New York Times in 2009, “If I can tell the story to America, whether it’s riesling or a boxer from Harlem, it will sell. I know on my gravestone it’s going to be, ‘Storyteller.’ ”

2) A steady consistency in producing and releasing high volumes of content:

Gary would have had nearly 300 episodes under his belt by mid-2007, so he was pumping out close to one video per working day.

The appearances didn’t end there. In 2008 he did a talk and tasting at Google, as well as a holiday segment for the Today Show alongside Meredith Vieira and Ann Curry.

That same year, some of the big marketing websites we know so well today began to take notice and already started positioning Gary as a marketing guru:

Now this may seem like everything happening at once, but really it was little seeds being planted all along the way.  

Take a look at this Google Trends chart:

This chart represents searches for “Gary Vaynerchuk” from 2004 to now.

Despite landing TV spots on major networks in 2007/2008, he still wasn’t making enough noise for people to pause and look twice. Gary Vee only started to become the known figure we recognize today in mid-2016! As I said, 10+ years of work.

The Diversity Of His Efforts

Seeing how effective the internet was at helping he and his family sell wine, Gary realized how he may be able to help other companies in other industries achieve similar success. So in 2009, Gary and his brother AJ launched VaynerMedia, a full-fledged marketing, media and branding company.

He was approached later that year by HarperStudio (former branch of HarperCollins) and walked away with a million-dollar, 10-book deal.

In his first book, Crush It: Why NOW Is the Time to Cash In on Your Passion, Gary advises other entrepreneurs on how to find and nurture their passions, and how to leverage the power of the internet to tell their stories and grow their brands. Crush It quickly climbed to the #1 position on Amazon’s bestseller list for Web Marketing book, and opened at #2 on both the New York Times Hardcover Advice Bestseller list and the Wall Street Journal bestseller list.

Even with all this early success, some things didn’t always go as planned for Gary…

He tried riding off the success of Wine Library, and simultaneously pursued a couple other wine-related ventures.

First up was Cork’d, a wine review site that Gary purchased and revamped sometime in 2007. According to TechCrunch, though, Gary let the website fall to the wayside and it actually ended up getting hacked.

Here’s a peak at the site from the time. It looks like it was a simple extension of the Wine Library site:

Several months later, with a newly hired CEO and the hacking incident resolved, Cork’d was back up and running, but it was only a matter of time before it met its final demise. Here gary is explaining their decision to close in a goodbye message released on Cork’d’s YouTube channel in January 2011:

Next up were Cinderella Wine and Gourmet Library, a wine shopping club and wine pairing site, respectively. Cinderella Wine’s website is still up and the last tweet on their feed is dated this past October, but the website for Gourmet Library reads as “under development” and the last word I can find on the company is in this Wine Library TV episode from May 2010.

These are just more examples of how Gary was always launching and trying something new. So they didn’t take off? Not everything is going to stick every time. Not every move is trailed by glitz and glamour, and he gets that. There are mistakes to be made and trials to overcome in business if you are to get anywhere worth getting to.

Today: VaynerTHIS, VaynerTHAT

Wine Library TV continued on for a total of 1,000 episode before ending in 2011, but today Gary currently hosts a new regular internet video show called #AskGaryVee, is the co-founder of two investment firms, VayerRSE and BRaVe Ventures, and even owns his own sports agency, VaynerSports.

One of his newest projects is called Planet of the Apps, Apple’s first original TV series where app developers come and present their app ideas to a panel in a Shark Tank-esque fashion. He co-stars alongside Jessica Alba, Gwyneth Paltrow and

And remember that awful office set-up above in his first Wine Library TV video? Today, Gary and his team hang out in a Manhattan high rise in one of New York City’s hottest new hubs, Hudson Yards, a tech-oriented neighbourhood built inside the city and co-inhabited with the likes of Coach, CNN, TimeWarner and SAP.

What Key Principles Seem To Guide Gary’s Hustle?

Sometimes things Gary says can leave you in immediate awe, other times, you may be left scratching your head while you try and catch up. One thing that can be said for sure, however, is this: Gary Vee may say a lot of s**t, but what he’s saying isn’t s**t. You feel me?

He says a lot, but it all leads back to a few specific principles.

What better way to take a look at those principles than through the eyes (and words) of the man himself? Since that first book, Crush It, Gary has gone on to become a four-time New York Times Best-Selling author. Here, I’m going to use the ideas behind his books, videos and various pieces of content shared over the years to highlight some of the core work/life strategies embraced and preached by Gary since the very beginning:

1) Start With Your Passion & Embrace Patience

Follow your passion, put in the work, and have the patience required to see those dreams become realities. Referred to by Gary as PP, Patience and Passion — these are two things the man has emphasized since his early days and that he made sure to address in that first book of his. At this Web 2.0 Conference in 2008, he talks about them both in depth:

One quote I love from this talk about passion is this one:

There [are] way too many people in this room right now that are doing stuff they hate. Please.. stop.. doing that!

He goes on to say that there’s no reason for anyone to be doing something they hate in 2008…

Yes… that’s right, 2008!

How many people do you know doing stuff they hate in 2018? I sure know a lot…

In this gem of a Q&A done not long after the release of his book, his talks again about Patience and Passion but acknowledges patience as the more underrated of the two, saying:

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.

Bottom Line: Find what you love and work toward making a living out of that. Understand that you can’t grow a business overnight, but if you work hard and keep pushing, good things will come.

2) Make Moves (And Quickly) Not Excuses

If you follow Gary Vee (literally or in the online world), you may find it hard to keep up.

He moves a mile a minute and talks just as fast.

In reference to his early wine ventures above, Gary is all about execution. It’s great to have an idea, but you’re not accomplishing anything until you put it into action. And if something falls flat, you don’t take that as a sign to give up.

Setbacks to others aren’t setbacks to Gary. One tweet making a little less noise than the other doesn’t faze him. Gary has been consistent for years at shipping content without worrying about the short term gratification of views, likes, retweets and comments. He’s in this for the long game and is all about making moves.

He has long put his money into many startups, and was even an early investor in Facebook, Twitter, Snapchat and Tumblr.

Yes, Gary Vee is certainly not one to shy away from new ideas and bold predictions. And, as a marketing and tech lover, it’s fun to look back on these predictions today because we see that he’s never really been far off the mark…

When asked back in 2011 what technology trends we could expect to see over the next 5 years, he responded, “Smart refrigerators, wallets going extinct, and a phone app that monitors your entire life.”

And how about this one:


Typically hindsight is 20/20, but Gary seems as if he can see just as clearly into the future. You may say it’s a gift, but really he’s just paying attention. He does a really good job at keeping plugged in on what’s happening in the world around him.

Bottom Line: Work to stay ahead of the pack. Always be doing and strive to win, but keep your eyes on the right prize. You’re not running a race, you’re running a marathon.

3) Create Content That Is Appealing, Engaging, Educational & Entertaining

Another thing he emphasizes is creating content.

He says you need to talk to the world. You need to spend time, every day, pumping out great content. Become a voice and communicate with the world. If you show that you care about your audience and customers, and give them something of value, they will return the love.

But simply creating content isn’t enough. You also need to be smart about where and what you post. You need to be where your audience is, create content that fits the platform you’re posting on, and create context around what you’re posting.

Gary is a social media whiz who has mastered the art of storytelling and understands the ins and outs of virtually every platform.

Bottom line: Create content and then create MORE content. People may not be listening to what you have to say right now, but if you become a part of the conversation by offering consistent, valuable content, soon enough they won’t be able to ignore you.

4) Say “Thank You”: Listen, Engage and Build Relationships Online

This is a big one.

In an interview with in 2011, Gary Vee said:

Too many people think this one-on-one stuff doesn’t scale, but giving a shit has an enormous return yield. For example, if a florist is nice to you, you’ll buy flowers there, even if 1-800-FLOWERS is cheaper. Yes, it’s hard work, but once everybody understands the value of engagement, everybody will do it.

Community is the second “C” (along with content) that Gary addresses in this early video about how he found success with Wine Library TV. You need to be out there listening, searching for your name or your company’s name on social media, and responding. Again, become part of the conversation and add value, because if you are not providing value to others, you’re not going to win.

This is what Gary’s second best-selling book, The Thank You Economy, is all about. In it, he talks about how he believes that to successfully build a social media presence, you must first build relationships. Give more than you get, and give people what THEY want.

As one example of how Gary LIVES this approach, a few years ago he used to send out personal videos to people who were following him and engaging on a regular basis.The website MobyPicture was one of the original video sharing sites and acted as Gary’s go-to resource for sharing videos on Twitter. If people asked Gary for a shoutout because it was their birthday, he responded with a video. If people asked Gary about his upcoming book, he responded with a video. If someone bought his latest book, he responded with a video.

There are more than 100 different video responses and shoutouts on his account between 2012 and 2014!

That’s hustle.

And here’s an old Twitter thread with Gary engaging with a fan who was testing him to see if he actually does grind it out into the early hours:

You can see here that Gary not only responded to this tweet, he responded with the impromptu video directed and delivered right to the fan. The fan was so impressed with the response that he followed up by pre-ordering Gary’s book!

Five years before the thread and videos above, Gary again showed his gratitude while offering his thanks to his YouTube viewers:

And people felt the genuineness, as can be seen in some of the responses under the video:

Gary understands knows from experience that personalization, acknowledgement, and one-on-one interaction have a tenfold return. He echos this same philosophy in his now popular marketing philosophy called the $1.80 Instagram Strategy.

Bottom line: Listen to your customers, build meaningful relationships, and offer something of value. This builds trust and brings people back to see what’s next.

5) Go For The Knock-Out: Give More Than You Get

Jab, Jab, Jab, Right-Hook is Gary Vee’s third best-seller. It builds off of the concepts of The Thank You Economy in that the jabs represent giving away value for free — tweets, blog posts, ebooks, videos, graphics, live video, comments, etc.— the stuff that people are hit with before the grand finale, the right-hook, which is when a brand asks for the sale.

Here he lays into the Oprah Winfrey Network for having a poor handle on this concept back in 2012:


“Jab, Jab, Jab, Right-Hook” is actually a really cool reference and a simple concept. It’s a reminder to not be about “me, me, me,” and it’s an approach that so many brands are not used to and really struggle to carry out.

So many companies and individuals are ready to throw the right hook at the beginning of the match rather than building up the audience’s interest and offering some entertainment value.

You bought the ticket, but did you get your money’s worth?

Bottom line: Don’t join them, beat them! The internet offers so many opportunities to share and connect. Be the one who leverages the tools (or hell, create your own!), and leave the world with something amazing!

6) Care Sincerely About Your Consumers

When you listen to your followers, it shows that you care. When you share your knowledge and insights, you leave an impression with people that you’re concerned with more than yourself.

You care because it’s the right thing to do AND because it truly makes all the difference. That’s the reason Gary had a burger delivered to the house of one of his hungry Twitter followers. In doing that, this guy makes a video expressing his gratitude and FREELY promotes Gary’s book and website while at it.

Gary says he answers all of his own emails (he sometimes receives upwards of 1,000/day), and he’s still known to this day to regularly engage with his followers online. Back before his feed was flooded with various forms of content, you could pick out these interactions more easily, like what you can see in this snippet where he’s just taking some time to thank people and express his gratitude:

That’s a lot of tweets to send out for one person.

Gary knows what he’s doing though. You could say he’s clever, but it’s actually so common sense to care it’s shocking more people don’t take advantage of similar opportunities.

Gary shares his life with his followers. He’s transparent and he’s genuine, and that comes through in all his messaging. He talks about this in this video from 2008 saying that the inability to hide in today’s world is a major win… for those who are good— but those who are in it for themselves will quickly be exposed.

Bottom line: Show your supporters that you care about them by acknowledging them and even wowing them! But be sincere in your words and actions because anyone can spot phoniness, whether it’s through a screen or not.  

Wrapping Things Up: What You Can Learn From This

So what have we learned from all that Gary Vee has displayed before us? How can you apply it to build on your own dreams and desires.

I’ll sum it up into four points:

1. Love what you do

If you do not love what you do and believe in it wholeheartedly, you’ll lose. You’ll be seen as inauthentic, you won’t be happy and, frankly, you’ll give up before you get anywhere good. Some of the grind, some of what you have to do, may absolutely suck, but if you love it, you’ll keep pushing through. You’ll push through the hardship and the angst to reach those successes that you’re striving to reach.

2. Offer value

Produce great, consistent content for your followers. The more content the better, but quality and context are also key. Know who you are speaking to, adapt to the platforms you are speaking on, and listen! Don’t throw things at people with the hope that they’ll stick; make it a point to understand and work with that.

3. Become a part of the community

Search up your brand regularly to see what people are saying about you. Seek out conversations occurring that are relevant to you, your business and your competition. Engage and interact in meaningful ways. It’s no longer about talking at people, it’s about transparency and having discussions.

4. Show gratitude

No one has to buy your stuff, like your photo, or listen to what you have to say. If they do, you should be grateful for them and show your appreciate at every chance you get. The online world is now about personalization and putting a face to the logo, so show your human side and engage regularly.

5. Be patient

This is the most important point. As hard as you work—and you should be working hard— you also have to practice patience. You aren’t rewarded just because you want it more, you have to continuously put in the effort. Gary didn’t get here by thinking he could climb Everest in a day, and he tries to encourage his followers to develop that same mentality. Keep going, even if no one is listening.

I’ll end with a quote from Gary’s talk at the Synergy Global Forum last year that is just.. so.. Gary VAY-nerchuk:

Everybody thinks there’s some shortcut. Everybody thinks they’re gonna make one f**king video and it’s gonna go viral and it’s gonna change their f**king life— no.. no. This is f**king 25-30 years in the making. It takes time.

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