Few modern-day business leaders are as iconic, revered and accessible as Gary Vaynerchuk. There are thousands of Gary V videos our there, these are the top 5 clips you shouldn't miss.

Since turning his family business, Wine Library, into an overnight sensation at the start of the decade, Gary Vaynerchuk has cultivated a massive, devoted following worldwide while building his own media empire. 

One of the first business leaders to embrace amateur filmmaking and free distribution channels to drive sales and marketing, Gary V has inspired millions of professionals to rethink not only how they do business, but why they do business.

The Top 5 Gary Vaynerchuk Videos

In today's business world, filled with self-proclaimed disruptors, thought leaders and elites, Gary Vaynerchuk's voice resonates. Self-assured, yet self-deprecating. Motivating, yet substantial. Loud, yet personable. Gary V is 10 steps ahead of 99.99999% of the business world - and true to his humble roots - he sets himself apart even further by being a passionate, trusted voice of authority speaking directly to the other 99% of the workforce fighting to reach the mountaintop.

Here at Ambition, we've been following Gary V closely for the better part of 3 years. A division of VaynerMedia works in our building, and we've been lucky enough to see Gary speak in person numerous times over the past year. Given our proximity, we're long overdue to give Gary V, one of our top 40 business leaders to follow in 2016, the Grant Cardone treatment and curate a list of his most epic video content. Here it is. 

1. August is the Month to Go All In

The most timely video on this list - and the one that quite frankly inspired it - is a quick 150 second blast of pure motivation. Gary V spends those 150 seconds doing what he does best: Using personal experience and introspection to extend a universally applicable hit of seasonal motivation to you, the viewer.

To invoke a popular phrase from one of Vaynerchuk's few contemporaries, Mark Cuban: "Work like there is someone working 24 hours a day to take it away from you.” Vaynerchuk doubles down (or should we say, triples down) on Cuban's sentiment with a challenge: "If you want it as bad as I hear you want ... if 2016 is going to be your year ... if you're sick and tired ... if it's your time ... these 31 days in August are exactly when you triple down, put in the grinding hours and get ready for your master plan. August is the month that sets the tone for your future."

Ready to run through a wall? So are we. But it's also worth noting that, right after issuing that challenge, Vaynerchuk hedges with a different command meant for a different type of listener. "For all those people ... with bags under their eye, who have hustled all year, who are crushing it, August is a very strategic month to go into a rest period, play with your friends and kids. You can play it one of two ways - it depends on where your head is at right now."

Injecting this kind of nuance into his videos is a classic Gary Vaynerchuk move, and what sets him apart from the legions of motivational speaker cyborgs programmed to issue only one directive. No matter who you are or what your mindset is, Gary V gets you.

2. Positivity on Offense: Elvis Duran Interview

Drake fans will appreciate that Elvis Duran opens the conversation by referencing famed Atlanta DJ Charlemagne as a big-time Gary V fan. Everyone else will appreciate the next 30+ minutes of honest and insightful dialogue.

There are too many highlights to cover, but here are a few standouts:

  1. 1:39 - 4:09: An amazing rundown of Gary V's background, in which he reveals the secret to his early success. "I wasn't a wine snob. I didn't talk at people about wine, I talked with people about wine."
  2. 4:09 - 8:44: One of Gary V's favorite topics - figuring out what you're good at, ignoring what society tells you and tripling down on what you love doing and excel at.
  3. 11:27 - 14:18: A great rant from Gary V about the importance of patience - taking time to figure out and develop your skills and goals. Embracing failure. Realizing you have one life and putting in the work to make the most of it. 
  4. 15:19 - 17:44: Another classic Gary V rant. Gary V stresses the importance of patience, hard work and valuing experience - while working in a passionate defense of millennials. 
  5. 17:44 - End: Gary takes questions from callers. Classic excerpt: "Yes" to hustle. "No" to Pokemon Go.

 Bottom line: You should probably start every morning by replaying this video.

3. Brilliant Idiots Interview: Part 2

Out of thousands of Gary V videos, this might be the rawest. Gary's capacity to transcend race, income level and personal background crystallizes in this film. The conversation leads off with an amazing synopsis of how to walk the walk and talk the talk, then dives into a deep insight to Gary V's mentality.  

The celebration of grittiness, hunger, struggle and living with a chip on one's shoulder might sound forced coming from a person in Gary V's position who, well, isn't Gary V. The genuine empathy and free-form conversation between a white business mogul and the Brilliant Idiots' African-American podcast hosts, Charlamagne and Andrew Schulz, is real, refreshing and vital to everyone who has suffered through the grim, race-related events of the past year.

4.  Vaynerchuk vs. Cardone: Cease-and-Desist Letter

First of all, major props to Salesman Red for highlighting the most important excerpt from Gary V and Grant Cardone's hour-long fly-on-the-wall video together.  With that said, in featuring this video, we encourage you to disregard the combative way it is contextualized by the Salesman Red team. No offense to Will Barron or his team for taking that particular angle - controversy sells and we likewise side with Gary's point-of-view in this exchange - but to boil this video down to Gary vs. Grant is to miss the greater point.

The point is: Gary V offers an important update to Grant's philosophy towards sales and business in general. That philosophy, espoused and perfected by Mr. Cardone, is: Be a shark. Hungry. Aggressive. Relentless.  A great mindset, to be sure. Especially speaking from a sales viewpoint. But not the whole mindset, as Gary V points out by cogently disagreeing with Cardone's celebration of a prospect's cease-and-desist letter and factoring in the new realities associated with the digital transformation of sales.

What makes this clip so great isn't just it's juxtaposition of Cardone and Vaynerchuk, the Socrates and Aristotle to much of the modern-day sales world, but the honest, open discussion that occurs regarding the salesman's mentality. I wouldn't qualify this as a signifcant philosophical disagreement - Cardone and Vaynerchuk seem to see eye-to-eye on 95 percent of core philosophy. But I would qualify it as the plaintive expression of that cutting-edge 5% where Gary V has evolved past Cardone and updated his philosophy for the current-day sales, marketing and business development landscape. 

5. A Rant from the Head, Hip and Heart

This last video is one we've recognized before: We profiled it earlier this year in our 50-page eBook, 25 Epic YouTube Videos to Inspire Your Salesforce. In our humble opinion, it's Gary V's most important video. And it never gets old. Here's the clip and our eBook write-up below. 

Mark Cuban is larger than life. Grant Cardone: the ulimate hustler. Marc Benioff is the technology visionary. But go poll the sales community and ask who their favorite, most inspiring public figure to read, watch and listen to is in 2016, and the odds-on favorite to win is Gary Vaynerchuck. For one simple reason: He's the realest. This, his most famous rant, recorded spur of the moment on a red-eye flight before he was truly famous, is a rare, transformative experience. The most appropriate point of comparison is like listening to Muhammad Ali or Kanye West in their finest hours. A captivating mix of confessionalism, confidence and calls to action.

This is perhaps the most universally relatable, transferrable rant you’ll find on YouTube. Part self-criticism, part industry-analysis, part pump-up speech.  And maybe the ultimate bottom line: “Bet on yourself. Bet on your community.”

Ambition: The Sales Management & Motivation Platform

Ambition is a sales management platform that syncs every sales department, data source, and performance metric on one system.

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