How Gary Vee is One of the Few Omnipresent Gurus Worth Listening To

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In an age where hard work and determination are valued way less than fake it till you make it, many have become skeptical of entrepreneurs who seem to spring out of nowhere, plastering themselves and their Lambos all over Instagram.

With good reason, because there is much to be skeptical about right now. The modern-day equivalent of a snake oil salesman prevails through social media, selling get-rich-quick courses to people unsatisfied with the struggle of nine to five. 

Buy my course, they will say, and you too can have a life like mine. 

That life usually incorporates a garage crammed full of the most expensive sports cars known to man. A walk-in closet the size of my last three houses combined. An entire cabinet bursting with the finest watches Switzerland has to offer. Possibly even a pin-striped private jet, ready to whisk the occupant away to a private island full of semi-naked, champagne-swigging Instagram models.

All this could be yours if you can part with $99 for my latest course, they will declare with the energy and enthusiasm of a freshly trained time-share salesman. What are you waiting for? 

Of course, many of us see straight through the insane hocus-pocus, but many do not. I have no problem with anyone who owns a Lamborghini. I wish I had one. I quite fancy my own walk-in closet, too. I would probably donate a lung to own a Lamborghini and would happily headbutt a nun square in the nose in exchange for my own island full of Instagram models.

I am joking, of course.

But my issue with these fake entrepreneurs is the ethos behind the sentiment. Fast cars and fancy watches are a byproduct of success and not the most important aspect of it. Accomplishments should be what you are proud of, not some gigantic diamond watch or gold-plated shoes.

Show off the success, not the trappings of it. 

The very fact that you are here, browsing StartupGeek for content geared toward entrepreneurial success through hard work, good planning, and diligent procedure, probably means that you, like myself, can see through fake gurus.

You are not easily sucked in by theatrics. You are starting a business because you want to succeed, create, and accomplish. With that, hopefully, comes heaps of money. And that is a fine thing too. I love money.

This likely means you distrust the modern trope of sudden affluence combined with massive media attention, and some of you might view Gary Vee as just another purveyor of snake oil.

He is, in my opinion, sometimes unfairly lumped into the fake guru category for reasons I can’t fully determine by a misguided minority of folks (that much is evident by jumping on Reddit and running his name). 

But I am here to say that these people are wrong and that Gary Vee is one hell of an exciting guy with advice worth listening to. He genuinely has something to offer, and if you pay attention to his advice, you will pick up something of value, I promise you.

Gary Who?

His face has been plastered over social media during the last decade, enthusiastically dispensing business advice and general life coaching. You almost certainly know of him. 

If you don’t, welcome to the world wide web. It must be your first day around here.

He is a content-producing mega-machine, and while his advice is quite brilliant, he can appear a little too enthusiastic and grating to some – resulting in polarizing opinions among social media users. Some of them wrongly perceive him as that snake oil guy. More on that later, however. 

Gary Vaynerchuck (or Gary Vee, as he is commonly known) was born in Belarus, where he was raised until age three, before moving to the US and settling in the Queens area of New York. His father landed a job in a local liquor store. Through hard work, he stashed away enough savings over the years to eventually open a store of his own.

This work ethic obviously rubbed off on young Vee, who started running his own hustles at six years old, selling flowers door to door. Flowers, I should say, that had been freshly plucked from the homeowner’s garden, then sold back to them with a cheeky pitch and a wry smile. You love him already, don’t you? 

He ran a lemonade stall at age eight. There is nothing groundbreaking or unusual about that, but you might view his hustling abilities in a different light when I tell you he ran several stalls at the same time, placing his young buddies as ‘store managers’ in each location. That is not just a cute hustle. That is a complex distribution network with multiple staff at eight years old. 

By his early teens, he had developed a deep understanding of the baseball card market and began trading them, creating thousands of dollars each week in revenue. 

Think about that. Not a few bucks, but thousands, and at just 13 years old. In a similar vein to Mark Cuban and Neil Patel, these early hustles would install an intuitive grasp of sales and marketing in the young Vee, which he would later employ successfully as an adult. 

Leveraging Liquor

His father, presumably delighted with his son’s entrepreneurial spirit but also keen to reel him in a little, gave him a job in the liquor store as a bagman. Not in the Mafiosi Tommy Two Fingers sense of the word bagman, but more a literal bagman, packing away customer purchases for two bucks per hour. 

It was a wise move on his father’s part. Vee became a wine expert just from hanging around the store and developing an interest in matters of the grape. Over the next few years, he would take a managerial role in his father’s various businesses, which by now had become numerous and broad – while simultaneously developing a keen interest in a new, groundbreaking technology known as the world wide web. 

Through the late nineties and early noughties, he became absorbed with the potential of the internet and immersed himself in studying it. There was potential with this new media, and he knew how to best use it.

After graduating college, Vee threw himself into the family business, rebranding it as The Wine Library and elevating its reach through social media campaigns and a vast content push. He became a dab hand with a natural flair for promotion spawning from his early hustling days.

I have said it time and time again through these case studies. There is so much value to be had from early hustles, and any child who leans towards hustles at a young age should be motivated and encouraged to take it as far as possible because it almost always pays dividends over the long haul. 

Neil Patel will attest, having sold overpriced vacuum cleaners’ door to door as a young hustler. Or Mark Cuban doing the same with garbage bags.  It teaches you something earthy and visceral about marketing that stays with you for life.

Wine Library Growth

He began taking social media campaigns to the next level by creating his own thoroughly engaging web show Wine Library TV. Using his natural charisma and enthusiastic delivery, he educated viewers about wine, reducing the complexities of different regions, vintages, and flavors into a more attractive, engaging, and fun topic for the masses. 

A niche was being carved out. Maybe not so much a niche but more a brand identity. While other wine experts wore dickie bows and peacock suits, Vee wore football jerseys and said things like my dude. He appealed to the masses and introduced the working classes to wine appreciation. 

In a few years, he had pushed over 1000 videos to an almost cult-like following. This, of course, kicked back to The Wine Library, and in turn, revenues increased from a few million to over $50 million.

Networks became interested in Vee and approached him about producing an actual series. Remarkably, he was not interested and viewed the future of TV as inferior to the potential of the internet. In his own words:

“I Don’t Believe In TV As The Future Media Of The World. I’m Not Going To Let Four Guys In A Suit Who Are 63 Years Old Tell Me Where The World’s Going Because I Know A Hell Of A Lot Better.”


Now something of a self-taught social media marketing expert, he decided to utilize this skill set by creating VaynerMedia, a full-service marketing agency. 

An impressive keynote speech at the Web2 conference in 2009 served as a brand push, and the company started pulling in clients immediately. It was an instant success.

He remained focused on social media, pushing out daily YouTube, Facebook, and Instagram shorts. The narrative was usually motivational – if I can have all this, so can you – but the core teachings were always helpful and accessible. How to improve your Instagram game. How to cold email. How to build a brand. 

During this period, he was probably most known for his highly motivational shorts, many of which went viral. Most days, a new short would spring out of nowhere, encouraging people to set goals and work hard for them. This became a constant theme, and for many people, the message rubbed off, encouraging the masses to get out of bed a little earlier, put the hours in, and work their socks off.

Vayner Media grew. His appearances and keynote speaking calendar were full to the brim. There was a period between 2015 and 2018 when it was difficult to browse your Facebook/Instagram feed without a highly engaged Gary Vee video popping up, lecturing on the values of hard work and determination.

With his ad agency booming – in 2016, Vayner Media enjoyed its first $100 million year – he turned his talents to publishing, striking a ten-book deal worth one million. Several of his books landed in the Times Best Seller list. Magazine launches, men’s grooming products, and the lifestyle brand One37PM all followed suit, enhancing his brand and creating further exposure.

More recently, he has been involved with NFTs, but that might warrant a case study of its own, so maybe we could put a pin in that, for now. 

None of this is particularly mind-blowing, though, is it? Let’s summarize and see. 

A Method To His Madness

So. A cheeky young chap is raised in New York and sets about running a few hustles. He takes over the family wine business, promotes it on social, and yields millions of regular viewers and fans through his brash, in-your-face personality. He relentlessly pushed out content daily, and for a few years, he was everywhere, shouting into a webcam what you should and shouldn’t be doing to improve.

He was a life coach, essentially. An unsolicited life coach who would spring out of your feed, screaming at you for making excuses and not trying harder. 

People took a shine to him. He capitalized on this and launched a marketing business, which exploded. Book deals, public speaking, and webinars followed. Fame, fortune, and success. 

His primary strategy revolves around a straightforward premise: content is king. He worked tirelessly to push out an incredible amount of content on various social channels, uploading multiple videos and shorts daily without respite. Sometimes multiple times per day.

But who cares? There are millions of entrepreneurs worldwide who have built successful businesses. Why should he have his very own case study on Startup Geek?

Because what interests me is his foresight and his wisdom. He took these two traits and leveraged social media as a platform to sermonize; through that, everything else fell into place.

But unlike so many of the fake gurus and fake entrepreneurs, he demonstrated his advice. Talk is cheap, and actions speak louder than words. He showed us all how to action his advice by actually doing it. 

But how does this help you, dearest startup entrepreneur? How can you replicate Vee’s strategy and build your own content-driven empire?

Let’s take a look.

Content Is King

His theory is that every business must be churning out frequent content; if you aren’t, you are unconnected.

Initially, he created and posted content himself, but now has a staff of 25 people helping him. Together, they produce approximately 100 pieces of content EACH DAY across YouTube, LinkedIn, TikTok, Instagram, Twitter, and his website.

Each platform comes with its own separate strategy:

YouTube: They will post a substantial video like a keynote or webinar speech but also draw down content for their daily vlog posts, with shorter videos on a focused theme.

Instagram: His team will grab a quote from that same video and post it with his image. They will also throw in short clips from the speech. These short clips are then posted as stories, for teaser content, on his personal YouTube channel.

Twitter: He uses it for more personal interactions, posting content from other channels simultaneously.

LinkedIn: His team will transcribe the video into a written post/article. He is beginning to focus way more on LinkedIn of late and recently commented that results are beginning to exceed other platforms in terms of revenue generated. 

So how do you replicate this strategy as a startup with limited funds?

The simple answer for a startup founder running a small business is that you cannot. It would be remarkably ambitious to copy this strategy, given that he probably has a seven-figure budget for his content team salaries alone. 

Considering he charges over $100K for a single keynote speech, just one speech per month will cover these salaries.

That is, of course, quite unrealistic for us mere mortals. 

The ethos is the same, however. 

Let’s look at how you could apply Gary’s strategy in a trimmed-down fashion.

  1. Produce at least one long-form video per week. You do not need fancy camera equipment – use a phone if you must.
  2. Hire an editor on Fiverr or Upwork to splice that video into smaller video shorts for Facebook and Instagram.
  3. The Fiverr/Upwork editor will create your video, then add a professional gloss and upload it to YouTube on your behalf.
  4. Hire a content writer (again, Fiver or Upwork) to transcribe your YouTube video into a blog post for your website.
  5. Hire a designer (hello again, Fiverr/Upwork) to create commissioned graphics for your LinkedIn, Instagram, and Twitter based on your YouTube video. Brief the designer to draw down quotes from your video and design graphics and memes for viral sharing.

While I don’t condone slave labor, there are plenty of talented creators on Fiverr and Upwork with rates as low as $5 per hour, if you are on a tight budget. Use them. They in turn will benefit from your review and slowly increase their rates, over time. It’s a fair system, despite how it may seem. 

Pearls Of Wisdom

Use these pearls of wisdom, and more like them, to grow as an entrepreneur. Unlike the nonsense-spouting fake gurus, this is advice worth listening to, I promise you.


“Many Of Us Waste So Much Time Every Day And Never Put In The Years Of Work That It Takes To Do Something We’ll End Up Being Proud Of.”

Partying is much more fun than hard work. So is a weekend playing Call of Duty. Hanging out on the beach with an eight-pack of beer is fantastic fun. Driving coast roads in a convertible, head to toe in designer clothes, seems like an excellent way to pass the time. But these days, too many people want those things without putting in the effort.

Launching a startup is not easy, but it is gratifying. With a lot of blood, sweat, and tears, those things will come in time. First, you must graft, sacrifice, fail, and try again. In time, you will be rewarded.


“Every Second You Spend Thinking What Somebody Has, It Takes Time Away From Something You Can Create For Yourself.”

Or, as the little French munchkin Napoleon Bonaparte once said, “envy is a declaration of inferiority” 

This one speaks for itself, really. Yes, you can sit on your backside, scrolling endlessly through socials with green eyes and consumed with envy, as you watch some idiot in a Las Vegas president’s suite take a swig of Cristal while sitting in a jacuzzi. Bragging about how much ‘cheddar’ he made selling courses that morning. 

Or you can flush your phone down the toilet, roll your sleeves, and start working. Hard. Insanely hard. If your fingers are not worked to the bone, you are not trying hard enough. Forget what everyone else is doing and focus only on yourself. 

I had a successful advertising business and was the largest player in my niche for ten years, but I had a spectacular fall and lost the business early in the first Covid wave. 

For twenty years, I have worked in and around advertising and marketing. My most raw talent was writing copy, so I started a new venture as a copywriter. With no portfolio to showcase, you must start at the bottom. So, I did. I went out and looked for clients of any description and started rebuilding my empire.

In my first week, I had music playing in the background as I worked, and out of nowhere, an advert. Some pearly teeth fakester sat in a bright yellow Mercedes G Wagon, boasting about his success in real estate. He was selling a book and appeared to be extremely wealthy, but it was arrogant wealth, not classy wealth. He looked about seven years old.

The timing was apt because, at that moment, I was writing a 250-word product description about a lady’s tote bag and being paid $4 to do so. It took me 2 hours to write, and while it might be the best product description ever written about a crappy tote bag, my net return worked out to $2 per hour.

I closed my phone and vowed never again to allow a fake guru into my mental space again. And I have not. Not until writing this article, that is. 

I worked extremely hard at copywriting, and after six months, I started to get somewhere. I now make quite healthy money from the endeavor, but more crucially, I am onto something, and the business is growing. But it took hard work and focus. Admiring the so-called accomplishments of fake gurus will do nothing to serve that focus and only detracts from it.

So. You do you. Forget everyone else. Work hard, stay focused, and it will all come together in time. If it does not, you simply fail forward, learn from it, and try again. And again. And again. 


“Close Your Eyes Until Your 29.”

This does not apply to all our Geekers but to those under 30. 

I happened to be watching a video compilation recently in which the same question would be asked of him by many budding entrepreneurs during various keynote speeches and seminars.

This question was along the lines of “I am only 25, but I am already lost. What should I do? I feel like I am stuck in a rut.”

Gary would reply with the same answer each time, in his usual enthusiastic way “You are not lost. You are just too early in the process, that’s all.”

Being patient in your twenties is difficult because you have little perspective. You probably consider 40 as quite old, but it is not.

It’s OK to stumble around in your twenties. That is probably what you should be doing. Use this decade to foster ambition, tweak your skill sets, and observe. Do not rush. Play the long game.

Patience really is a superpower. With its litany of young millionaires, social media has become a breeding ground for inpatient entrepreneurs collectively sprinting to the finish line with undue care, focus, and attention. Take your time and spend a few years deciding what your strengths are. Improve. Tweak. Observe. Be patient. 


I have a theory. 

At the time of writing, the most popular online startup business in 2022 is a tee shirt store, and I think I know why. 

It is straightforward to set up, using a print-on-demand supplier to create and ship the designs. You can hire a cheap Shopify store builder on Fiver or Upwork for $100, and boom, you are in business with your own store.

You are now an entrepreneur, and for many people currently, that is the sole objective. To be able to say I am an entrepreneur! 

Too many people want to be in the same club as their social media entrepreneur idols. They might not own a Lamborghini, but they can at least declare they are in business, and heading for one. 

It is not enough.

Gary himself says the main problem with new entrepreneurs is a lack of patience. You must play the long hustle; getting good results will take many years of hard graft. That is not common knowledge, but if it were, most young entrepreneurs would quit. 

They want the Lambo, Audemars Piguet watches, and private jets because social media has made it look easily attainable – but they are unwilling to put in the grind.

If you are reading this, you are probably already involved in a startup or at least thinking about it. Hopefully, you are doing it for the right reasons: the sense of accomplishment and the construction of something remarkable.

You cannot wait to slog it out in the trenches and build something spectacular, and as a result, you will hopefully make lots of money in the process, giving you a great life.

If that is you, I applaud you and wish you all the best. But if you are getting into business just to say you are in business, you are no less fake than the fake gurus. And let’s see where they are ten years from now.

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About the author: Matty Bates

With over two decades of online marketing experience, Matty has helped launch successful marketing campaigns for a wide range of companies in the eCommerce space, largely through writing engaging copy and devising advertising campaigns with a definite creative flair. After running a small but very successful direct-response advertising company for 12 years, Matty ventured into freelance copywriting in 2019 while also creating and managing his own eCommerce projects, selling viral products through social media sales funnels and landing pages. Matty joined Startup Geek as a senior content writer in mid-2022, before quickly rising to Editor a few months later. His natural style might be described as mildly satirical and humourous - which is an approach not usually employed within the entrepreneurial content realm - but helps to deliver an interesting touch of color to the informative content we are producing here at Startup Geek.

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