By: Gary Vaynerchuk



Gary Vaynerchuk wrote the book #AskGaryVee to bring his bombastic advice from his online video show of the same name into book form.

Why should you listen to him?

He’s built two $100 million per year businesses, and he’s probably the only person to become “Internet famous” through dispensing business advice alone.

His current business, VaynerMedia, is a digital advertising agency that has quickly grown to $100 million in revenue. That is an incredible trajectory for a business that traditionally takes a very long time to scale up.

Here are our favourite pieces of advice from Gary on how to succeed as an entrepreneur.

Keep your head in the clouds

This is all about keeping your eye on the 30,000 foot view in your business, and making sure you have a set of principles that guide every action and decision.

Gary tells us that if you religiously follow the few core business philosophies that mean the most to you, and spend all of your time there, everything else will fall into place.

You should have your own philosophies or ideas, but here are Gary’s commandments to help you get your juices flowing:

  • Bring value to the customer.
  • Provide 51% 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.
  • Never be romantic about how you make your money.
  • Try to put yourself out of business daily.

Some of these will only make sense if you follow Gary’s work. For instance, he doesn’t mean literally putting yourself out of business, but to always look for ways to innovate on “what’s next,” so you are never beaten to the punch by a new or existing competitor.

Keep your nose in the dirt

While you keep your head in the clouds, you also need to keep your nose in the dirt. The dirt is the execution side of your business.

Here’s an example from Gary in order to make this point.

Almost all marketing agency CEOs will make sure their account teams suggest to their clients that they get on Instagram and Pinterest, but will have never used the services themselves. In Gary’s business, knowing the details is knowing there is a 15-person limit to an Instagram chat and that infographics are the way to get attention on Pinterest.

He understands these details by immersing himself in them and is a world-class practitioner at the “stuff” his business produces. This way, Gary says, he can sit down with a potential client and tell them they are working with the best social media practitioner at the best social agency in the country.

Understanding and executing on the details in your business is a great differentiator.

So how should you split your time between the clouds and the dirt? This is a personal decision and will depend on the circumstances, but you should probably swing no more wildly than a 70/30 split in either direction at any one time.

Also, never take your eye off cash flow, which is on the dirt side of the equation. As Gary says, cash is like oxygen to your business. Dropping the ball on customer service or company culture is a huge mistake, but no mistake will ever hurt more than getting your cash flow wrong. You cannot - EVER - run out of cash.

Hustle, Hustle, Hustle

One of the things that Gary is known for is hustling. While he’s always talked a big game about being one of the hardest working people on the planet, he recently started a video blog chronicling his day-to-day life to prove it. Basically he is in “go” mode from sunrise until late at night, often getting home from his last meeting at midnight.

And he’s not only working hard, but he is also doing his best to work smart.

He defines hustle as maximising the energy you put into your business, and it’s about making every minute count.

While most of the world is busy complaining about our “always on” culture, Gary views it as his competitive advantage. Every entrepreneur worth their salt, he says, is grateful as hell that the Internet allows us to hustle while every one else is playing video games and watching Netflix.

Working harder is the easiest thing you can do as an entrepreneur to succeed. How much time are you spending every day mindlessly scrolling through Facebook or watching TV? Cut out that hour or two and work. It might not seem like a big deal for that day, or that week, but over time those hours could be the difference between massive success or massive failure.

It’s simple - if you want to grow your business, hustle every single day until there isn’t a single drop of juice left. Then get up and do it again tomorrow.

Create great content

Bestselling author Dan Pink suggests that we are all in sales now and Gary suggests we are all media producers too. It’s old news that we’ve shifted away from the days where television, radio and print were the only ways a company could tell their stories to massive audiences. The one thing that hasn't changed however, is how to create great content. 

According to Gary, there are a few simple rules around how to create quality content.

First, it needs to appeal to the heart. As always, emotion trumps logic. You need to create content that connects to your audience on an emotional level.

Second, it needs to be shareable. Unless you are a massive corporation with an ad budget of tens of millions of dollars, the only way you are going to reach a large audience is for your audience to share it.

Third, it needs to be native to the platform on which it appears. For the traditional media channels, it’s easy to see why you need to make the content native to the platform. For instance, you wouldn’t just take a 30 second television spot and use that for a radio ad, would you? So don’t make the same mistake on different social platforms.

Fourth, it needs to break through the noise. The best way to do this is to “respect your audience.” For instance, if you wanted to sell wine, you would likely attract more attention with a blog post about “Five Bottles Under $10 That Help You Get Through the Day When You Have 8-Year-Old Kids,” than you would with “Five Reasons My Wine Is The Best!”

Engage with your community

Now that you have great content that is useful or entertaining to your audience, the hard work begins.

This is where some of that extra time you freed up by not watching Netflix is going to come into play and when you start engaging with the audience you are trying to reach.

Unless you are fortunate enough to already be a celebrity, the formula for success is to put out quality content every single day, and engage with your audience. As Gary says, "it really is that simple and difficult."

How do you engage with your audience? You can do what Gary did when he first started out using social media for his wine business. He would fire up a Twitter search, look for people asking questions about wine and answer their questions. Those people would check out his profile, which linked back to his site, and would eventually start buying wine from his online store.

Is engagement a lot of work? Of course it is. But as we already discussed, that’s just part of the game these days.

Interestingly, even after creating and scaling two businesses to $100 million a year in revenue, Gary is still the one sending out all of his tweets, posting on Instagram and creating his Snapchat videos. So, if Gary can do all of that, we probably can do it too. 

Be self-aware

Self-awareness in business is critical and there are a couple of things you need to do in order to make it work for you.

The first thing you need to do is create an environment where those around you can tell you like it is. It is important for you to know what you're good at, what you're not-so-good at, what's working and what isn't. More importantly, you want your employees to feel safe doing this or it will never happen. This might mean hearing things that you disagree with or that may even upset you, but it is your job to listen to the feedback and thank them for bringing it to you. 

Once you have listened to and taken the feedback into consideration, begin to shift your focus and energy on the things you are great at. Delegate the things you may not be so great at to others. 

You’ve likely advice before, (i.e. in Now Discover Your Strengths), but it bears repeating. No one is great at everything. The sooner you can acknowledge and accept this fact, the better. 

Here’s a concrete example from Gary’s own journey. It’s a poorly held secret that Gary - a guy who has written 4 NY Times best-selling books - isn’t a great writer.

He realised early on that if he was going to create content that was compelling to his audience, he would have to do it by video. Instead of focussing his attention on trying to become a better writer, he poured all of his energy into creating the best video content he could.

When it's time for Gary to write - including the 4 business books he’s written and any blog posts he creates for his blog - he sits down and expresses himself verbally. He leaves the writing to his staff, who simply helps him turn his message into the written word.

Similarly, when it comes to your own business, you should be spending all of your time focussed on where you can add the most value to your business. 

But how do you know what things you should be delegating, either to another person at your company or outsourcing to another? As Gary points out, it’s an easy decision when you need A-level work and you’re an F. It’s a lot harder to make that call when you are a B.

If you make an honest assessment of the situation and determine there’s no way you can execute on a specific area of your business at an A-level, delegate it.


So there you have it - a few of our favourite pieces of advice from Gary Vaynerchuk. If you want a deeper dive into the mind of this world-class entrepreneur, go check out his Youtube channel where you’ll find the video show this book is based on, or get yourself a copy of the book wherever books are sold.