What Gary Vaynerchuk Can Teach You About Advantage Gambling

By Randy Ray
Published on April 13, 2019

When you need gambling advice, odds are that you look towards the pros. These are the players who have all the experience in beating a game and winning profits.

For example, Randy “nanonoko” Lew is a good person to watch if you want to learn advanced poker strategies that’ll improve your game. Lew regularly streams his online poker sessions via Twitch and offers quality tips.

But sometimes it’s helpful to look outside the gambling world for advice that’ll help you win more often. This is especially the case if you want to be an advantage player who makes lots of money.

I find that Gary Vaynerchuk is one of the best sources of inspiration for gambling, or anything else.

“Gary V” is far from a professional gambler himself. But his habits and advice provide a template to help you win more often.

Keep reading as I discuss more about Vaynerchuk and his philosophies/habits that’ll help you become a better advantage gambler.

Who Is Gary Vaynerchuk?

Gary Vaynerchuk is an American entrepreneur who’s become very popular in recent years thanks to his speaking engagements and YouTube videos.

Not only has he gained worldwide fame, but he’s also become extremely wealthy with a $160 million net worth. This is all the more impressive when considering that Vaynerchuk had very little money several years ago.

Gary V was born in 1975 in Babruysk, Belarus. His parents immigrated to Queens, New York, when he was three years old, then moved to Springfield, New Jersey.

Gary’s father, Sasha, worked at a liquor store during the family’s early years in the United States. He was eventually given the chance to become a partner due to his impressive work ethic.

What ensued was Shopper’s Discount Liquors becoming a big success and pulling in $3 million per year. Gary worked in the family wine retail store throughout high school, college, and his early adult years.

Gary V eventually assumed control of his dad’s store and started a YouTube channel called WineLibrary in 2007.

Vaynerchuk combined this YouTube channel with a website (launched 2006) to increase Shopper’s Discount Liquor sales to $16 million per year.

He sold the store and website in 2011, which allowed his father to retire. Vaynerchuk didn’t share in the profits because he felt that his efforts were to repay his father and mother for raising him.

Following the sale, Gary V began focusing more on VaynerMedia, a digital ad agency that he started with his brother in 2009.

As mentioned before, Vaynerchuk didn’t have much money to start with after he left the liquor business. But he was armed with the same skills he used to rapidly build Shopper’s Discount Liquors into a big success.

Gary V used his experience to quickly turn VaynerMedia into one of the biggest players in social media-based advertising. VaynerMedia now employs over 600 people and grosses more than $100 million in annual revenue.

Aside from running his advertising company, Gary also has a successful YouTube channel called the DailyVee, where he interviews famous and successful people. He dispenses tips to viewers on how they can become more successful in entrepreneurship.

Vaynerchuk’s success has allowed him to become a featured speaker at conferences and an accomplished author. You can find countless videos of him speaking at major conferences, where he explains the importance of being more self-aware and understanding one’s strengths and weaknesses.

As a writer, Vaynerchuk has written several successful books. This includes Crush It!, which rose to #1 on the Amazon Best Seller List for Web Marketing books.

You can see that Gary Vaynerchuk’s resume doesn’t include being a card counter or poker pro. But he obviously knows a thing or two about success.

Now that I’ve covered who Gary Vaynerchuk is, I’m going to move on to how you can use his philosophies to win more through gambling.

Don’t Be Afraid to Start Small and Build Your Bankroll

One of the biggest problems with many aspiring advantage players is that they want everything right away.

These same gamblers don’t want to face the reality that it’s far better to grind up the ladder in a controlled manner, rather than taking big shots before they’re ready.

But looking at Gary Vaynerchuk’s rise is a good way to temper short-term expectations while seeing what can be accomplished in the long run.

Vaynerchuk addresses this in Crush It!, where he writes, “Even if your ambitions are huge, start slow, start small, build gradually, build smart.”

You may have dreams of taking down a huge poker tournament, earning thousands of dollars per night in blackjack, or winning six-figure sports bets.

But like Gary V says, the best way to approach these dreams is with a long-term perspective. Look at your situation and figure out what’s realistic in terms of stakes.

Here’s an example of a common way to handle poker cash game bankroll management.

  • No-limit cash players should have 20-30 buy-ins for their desired stakes
  • You want to play $1/$2 stakes ($200 buy-in)
  • 200 x 20 = 4,000
  • You should have a minimum bankroll of $4,000

Having 20 cash game buy-ins might seem excessive. But many successful players have proven that this strategy works.

You may not have the money to take a shot at the big time right now. But with time, you can build your bankroll and skills to the point where you’ll eventually earn major profits.

Identify Opportunities and Attack Them

One thing that can be seen in Gary Vaynerchuk’s story is that he’s capitalized on the best opportunities available.

Gary V frequently discusses how he knew that YouTube was going to be big when he started doing WineLibrary videos back in 2007.

Back then, YouTube was far from what it is today. But Gary Vaynerchuk continued producing videos for Wine Library until his channel eventually grew.

Gary Vaynerchuk also had the vision to see that Facebook and Twitter were great ideas. He invested some of his VaynerMedia profits into these companies and has seen a handsome return.

The takeaway here is that you should constantly be on the lookout for advantages that can help you make lots of money.

This is easier said than done when considering that many casino games and advantage techniques have existed for decades. Card counting, poker, and sports betting are all well known.

But new games and potential advantages come along from time to time. Just a few years ago, daily fantasy sports (DFS) was in its infancy.

Many DFS players were still trying to figure out effective strategies that could help them beat the game. Players are better today, but DFS still has some soft spots.

Esports betting may be the next great opportunity since it’s growing at a rapid pace. Eilers Research forecasts that esports gambling will be worth $23.5 billion by 2020.

Considering the rise of both the esports industry and its betting niche, this is a lucrative pursuit. Much like Gary Vaynerchuk became a pioneer in YouTube and social media, you can do the same with esports betting.

I’m not saying that wagering on video games is brand new. But there’s lots of room for aspiring pros who are willing to dedicate time to learning the teams, players, and betting strategies.

Ideas Are Sh*t – Hard Work Is Everything

Many people think that business success is all about the idea. These same people believe that simply coming up with a good idea will make them immensely successful in business.

Gary V thinks otherwise, as he commonly says, “Ideas are sh*t.”

He doesn’t truly believe ideas are worthless, even mentioning that “execution is pointless without the ideas.”

But his point is that far too many people over-emphasize the value of ideas, only to underestimate the hard work they must do to reach their goals.

The reality is that you can’t just rely on finding a good advantage or jump into a newer gambling activity like esports wagering. You also have to put a large effort in to succeed.

Gary Vaynerchuk commonly uses the hashtag “hustle” when tweeting motivational content to his followers. You need to keep the same mindset regardless of what path you choose towards making gambling profits.

Live the Games You Play

Some players have this romantic vision of what being a professional gambler is all about. They picture sitting at the blackjack or poker table for a few hours, making thousands of dollars, eating at a casino steakhouse, and then heading home in their Lambo.

The reality is a stark contrast to this, because being a pro gambler is a long grind filled with highs and lows.

Even with an advantage, you’ll lose nearly half the time. And even when you’re winning, playing casino games for hours becomes tedious.

This is when it really pays to actually love gambling and exploiting advantages. You might not always enjoy the hours involved, but you do need an overall love of the game.

Gary V says as much himself in Crush It!.

“Live your passion,” he writes. “What does that mean anyway?

“It means that when you get up for work every morning, every single morning, you are pumped because you get to talk about or work with or do the thing that interests you the most in the world.

“You don’t live for vacations, because you don’t need a break from what you’re doing—working, playing, and relaxing are one and the same.”

You shouldn’t try to become an advantage gambler if you’re only thinking about the lifestyle and money involved. Winning profits through gambling isn’t as glamorous as it seems.

But there are aspects to enjoy about the activity. And if you really appreciate these elements, then you should get more serious about gambling.

Be Willing to Try and Fail

It might appear that Gary Vaynerchuk’s life has been a straight upward shot ever since the mid-2000s when he started becoming a popular YouTuber.

But the truth is that Gary V has failed plenty of times during his climb to the top of the social media world.

He frequently says, “I love losing.” To Gary, losing means that he’s learning a lesson that can make him better in the future.

Gary Vaynerchuk frequently talks about his school years, too, especially how he was a poor student. Teachers never thought that he would amount to anything due to his grades.

“I failed all my classes and that’s why I’m winning,” he says. “In hindsight, the fact that I was considered a failure for the first 18 years of my life has become the foundation of my success.”

If you’re interested in gambling with an advantage, but you’re letting fear stop you — don’t.

Instead, be willing to get on the tables and fail. Doing so will help you learn lessons that can eventually make you a winning gambler.

The worst thing you can do is sit back and only dream about doing. Take your shots and accept losses for what they are — a chance to improve at what you want to do.

Don’t Obsess Over Perfection

Another common misconception about advantage players is that they’re always on top of their games and winning.

You have to be really good at whatever game you want to play. But you’re not always going to be on your A-game.

This relates to a subject that Gary Vaynerchuk often talks about, in that you shouldn’t obsess over being perfect.

“Stop focusing on dumb sh*t,” he says. “Don’t be afraid to break things. Don’t be romantic.

“Don’t take the time to breathe. Don’t aim for perfect. And whatever you do, keep moving.”

If your dream is to be perfect at whatever game you’re playing, then idolizing this perfection isn’t the best way to get there.

“There’s no such thing as perfect,” says Vaynerchuk. “Chasing ’perfect’ is the shortest road to not achieving it.”

Gary V is a risk taker, which is exactly how he became an in-demand speaker and highly successful entrepreneur in a decade’s time.

“Life shrinks and expands on the proportion of your willingness to take risks and try new things,” he states.

You need to have the same mindset about whatever casino game you put your mind to.

This isn’t to say that you should skip over learning strategy and improving your game. But you also don’t want to, as Gary V puts it, “Focus on dumb sh*t.”

Don’t obsess over some obscure strategy detail that will only increase your edge by 0.000001%. Instead, look at the bigger picture and what you can do to boost your profits and success the most.

Know How to Deal With Downswings

You won’t normally have a massive edge in your preferred game even if you’re a great gambler. This means that you’ll deal with plenty of downswings and emotions on the road to profits.

It’s best to know about and prepare for these times well in advance. Not only do you need a large bankroll to help you get through rough patches, but you also need the mental fortitude.

This is another area where Gary Vaynerchuk can help because he rose from being a poor student into a rich and famous entrepreneur. And what’s impressive about Gary V is that he’s far from finished in his career.

But he didn’t get to this point without struggles along the way. And he has some good advice for how you can make it through the rough times.

“You’re going to go through a time where you’re not going to make any money,” he writes in Crushing It!: How Great Entrepreneurs Build Their Business and Influence.

“It’s not going to be a week, it’s not going to be a month, it’s not going to be one year. It’s going to be years.

“And during that time, if you don’t love what you do, it’s going to be very hard to stick it out. That is something that people don’t understand when they hear, ’Follow your passion.’

“They hear rainbows, unicorns, bullshit. But the truth of it is that it’s important, because if you don’t enjoy what you’re doing, you’re going to be that much more likely to quit when sh*t’s hard.”

Hopefully you never go through a point where you’re not making money for years. But you may deal with downswings that last for months, which feels like years when you’re depending upon the money.

As Gary V points out, it helps a lot if you enjoy what you’re doing. Loving the game you play helps with battling through losing streaks.

You Can Be Successful at Any Age

Many people believe that your chances of success in gambling or any other pursuit diminish considerably as you age. The influx of 20-somethings who’ve made fortunes through card counting, poker, and DFS back up this idea.

While it’s true that becoming a winning gambler is harder when you have additional responsibilities (e.g., job, family), it’s certainly not impossible.

Simply knowing that you can still be successful past your forties and fifties is a big step in the right direction.

This is one of the most common topics that Gary Vaynerchuk discusses in his speeches. Gary V has heard plenty of fans say that they feel too old to succeed.

But Gary Vaynerchuk always stresses, “You’re never too old to be an entrepreneur.”

His words are inspiring for gamblers between the ages of 50 to 70, who may think that time has passed them by. But Gary isn’t just blowing smoke — he really believes that anybody of any age can get out and hustle.

In fact, Vaynerchuk thinks that older people have some inherent advantages over younger entrepreneurs. Namely, they have more experience and realize that not everything is a short-term race.

An older gambler will have these same advantages. It’s also possible that they’ll have a larger bankroll than a younger player due to savings.

Poker pro Doyle Brunson is the ultimate example of an older gambler who’s still succeeding. The 85-year-old regularly plays in the “Big Game” at Bobby’s Room (Bellagio), which features the toughest high-stakes poker competition in the US.


Gary Vaynerchuk may not be an advantage gambler himself. But his advice and work ethic have many parallels that translate to the gaming world.

The biggest thing that you can learn from Gary V is that becoming successful is a grind. You don’t just sit down to a blackjack or poker table and immediately have an edge.

Vaynerchuk spent countless hours learning the ins and outs of social media before turning VaynerMedia into a giant. He also pours hours into his business pursuits, working from sun up till sun down Monday through Friday.

Another thing that Vaynerchuk preaches is how ideas aren’t everything. It’s not enough to be one of the early adopters of esports betting — you also have to work hard enough to build a true edge.

It’s also important to be self-aware of your skills and starting point. You may dream of winning a fortune through gambling, but you must build your skills and bankroll to the point where this becomes possible.

Gary V also advises that you should embrace failing, rather than fearing it. Taking calculated risks on advantage gambling and learning from mistakes is preferable to taking forever to get started.

Again, Gary Vaynerchuk isn’t going to teach you the proper hole carding techniques or how to fill out a DFS lineup. But his advice relates well to beating casino games from an overall perspective.

If you haven’t already seen him speak, I recommend pulling up some Gary V videos and getting the full effect of what he has to say.