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One Entrepreneur’s Take on Leadership, Social Media & Self-Awareness

By: Gary Vaynerchuk

Reviewed By: Ramona Sukhraj

It’s been my experience that a business book never really provides more than a handful of actionable tactics you can start using in your life right away.

In #AskGaryVee: One Entrepreneur’s Take on Leadership, Social Media & Self-Awareness (the latest book from entrepreneur, speaker, and social media mastermind, Gary Vaynerchuk), however, you get 370.

Since the book is straight Q&A, however, this summary is going to focus on three overarching principles that can help anyone find their hustle. 

Why #AskGaryVee?

#AskGaryVee is based on Gary’s show with the same name, where people send him questions using the hashtag #AskGaryVee, in hopes that he’ll answer them live on the air.

Here’s a recent episode if you’ve never seen it:


For the show, Gary’s team chooses the questions in advance and keeps them under wraps until they’re recording, yet, nevertheless, Gary always manages to answer in specific, informed detail -- because quite frankly, he knows his shit.

This becomes even clearer looking at Gary’s reputation as a guy who crushes Q&A and his impressive business track record.

Here’s a brief rundown of his resume:

  • Wine Library: Gary took over his family liquor store and built an online wine empire, growing the business from $3 million to $50 million per year.
  • VaynerMedia: After his success in the wine industry, and most notably with his Wine Library TV show on YouTube, he launched this social media agency in 2009, which is now doing over $50 million a year.
  • VaynerRSE: An investment fund focuses on consumer technology while also acting as an incubator.
  • DailyVee: A vlog started by Gary in 2015, chronicling his business/office life.
  • Crush It!, The Thank You Economy, and Jab, Jab, Jab, Right Hook: In 2009, Gary signed a 10-book deal with HarperStudio, preceding #AskGaryVee with these three phenomenally successful titles.
  • Gary was an early investor in several successful startups, such as Tumblr and Buddy Media.

But back to the book at hand.

Point #1: Understanding Your “Clouds and Dirt”

Clouds and dirt (to my understanding; what are you reaching for and what keeps you grounded) are how Gary Vaynerchuk describes his motivation and the way he does business.


Here’s how he explains them in his own words in the book: 

I spend all my time in the clouds and the dirt.

The clouds are the high-end philosophy and beliefs that are at the heart of everything I am personally and everything I do professionally.

Personally, it’s really simple: family first. Nothing else really matters.

Professionally, it’s not much different. That’s what I often tell my staff at VaynerMedia—99 percent of what we deal with every day in business doesn’t matter. This usually gets me a mix of confused, curious, and even disdainful looks from my new top execs or employees hearing it for the first time because of course, they think that to do their job well, everything has to matter. But it’s just not true. If you religiously follow just the few core business philosophies that mean the most to you and spend all your time there, everything else will naturally fall into place. 

My clouds are extremely simple, and might sound familiar to anyone who has been following me for a while:

  • Bring value to the customer.
  • Provide 51 percent of the value in a relationship, whether it’s with an employee, a client, or a stranger.
  • Always play the long game of lifetime value.
  • Smart work will never replace hard work; it only supplements it. People are your most important commodity.
  • Patience matters.
  • Never be romantic about how you make your money. Try to put yourself out of business daily. 

These are my commandments.

So you see, the clouds don’t just represent the big picture; they represent the huge picture, the everything. They are not goals. Goals can be achieved and set aside or moved. “I’m going to buy the Jets” is a goal. It drives me, too, but it’s not at the core of how I run my businesses.

The dirt is about being a practitioner and executing toward those clouds. It’s the hard work. On  a personal level, my dirt is making sure I communicate well with my loved ones, that I show up and stay present, that  I apologize when I mess up and that  I make sure it doesn’t happen too often. You know, the stuff of being a good spouse, parent, son, sibling, and friend.

Professionally, it’s knowing my craft. It’s knowing there is a fifteen-person limit to an Instagram chat and that infographics over index on Pinterest. It’s understanding Facebook ads and the ROI of Vine. It’s noticing changes and trends and figuring out how to take advantage of them before anybody else. 

The vast majority of people tend to play to the middle, which is why they usually only succeed up to a certain level and then plateau.

At the end of the day, what is your true motivation? What are you trying to achieve and what do you need to do to accomplish it?

Knowing these “clouds and dirt,” your path to success in business will be much clearer.


Point #2: Finding Your Hustle


Gary has built his personal brand around one of his greatest business strengths -- hustle. As the video above, from his homepage, tells you, he considers it the single most important word. 

Talent can only go so far. Even if you are naturally talented or educated, you need to hustle to make things happen and achieve your goals. 

When asked if hustle like this can be learned, Gary says, “I don’t know if it can be taught so much as it can be inspired.” 

He believes that certain work environments can inspire or diminish hustle, but he also believes DNA plays a role. (Just look at his family’s business, for example.)

It’s important to note, however, that hustle may vary for every person. Some may consider it working 24 hours a day, 7 days a week. While others, like Gary, hustle during the week and take the time between Friday night and Monday morning to rest and spend time with his family. 

The thing is, though, I’ve never really understood why it would be an advantage to be a morning person, or why morning is valued more than other parts of the day. If you do your best work first thing in the morning, great. But some people work best at 3am, 5pm, or 10pm. There is no right time to hustle, as long as you are hustling.”

Some people may be more productive in the morning while others work their best at night.

The takeaway is to put yourself in a position to do your best work and be around the best people and you’ll feel motivated to hustle more. 

Point #3: Remember These 7 Social Media Predictions 

Very few people know social media better than Gary.

He’s obsessed with it and built a hugely successful agency around it. 

He’s accurately predicted the rise and fall of several platforms over the last several years, including Facebook, Twitter, Tumblr, Instagram, and most recently, Snapchat.

Consider the points below from #AskGaryVee some of his most up-to-date advice: 


  • Gary is a fan of the latest algorithm change and thinks it will help deal with the biggest issue Twitter is facing right now -- it’s too noisy
  • He also stresses that the algorithm will benefit those who are actually providing value, so it’s a non-issue for brands that know their buyer personas well 


  • Gary predicts that Google AdWords will end up like YellowPages and Facebook Ads are just starting to grow
  • The reach you can get on Facebook is well worth the cost of advertising on the platform
  • Facebook Live is already becoming a rival for YouTube, but YouTube will remain the go-to platform for now 


  • Instagram is better for engagement because it allows users to focus more attention on your brand than Twitter or Facebook
  • Instagram is still younger than people think and we need to give it time to evolve
  • Long-form captions on Instagram are trending, and for many audiences, performing better