Leaders need their head in the clouds, nose in the dirt … and a good glass of wine

July 20, 2016

Sitting in the back of a taxi with Gary Vaynerchuk, stuck in the late evening Istanbul traffic, I was struck by how little he had to say. Here was the guy who a few hours earlier had joined me on stage, who had been ripping into every established idea in business, and with more f*** words than full stops. He had been full of himself, loud and arrogant, strident and dismissive.

Now here is was quiet, polite and thoughtful. Talking about how for all his blogging, speaking, writing and movie making, what he really likes is to spend time with close friends. And a good bottle of wine.

On stage, on video, I didn’t warm to him. But now he seemed more engaged, and engaging.

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, an incredible trajectory for a business that traditionally takes a very long time to scale up.

Here are a sample few 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 that 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, but here are Gary’s commandments to help 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 for always looking for ways to innovate on “what’s next” – so that 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 are suggesting that their clients 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. He 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 that 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.

One thing that you can never take your eye off on the dirt side of the equation is cash flow. As Gary says, cash is like oxygen to your business. Dropping the ball on customer service or company culture is huge mistake, but no mistake will ever hurt more than getting your cash flow wrong. You cannot, ever, run 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. He is basically 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, he’s doing his best to work smart.

He defines hustle as maximizing 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

Dan Pink tells us that we are all in sales now, and Gary tells us that we are all media producers now. 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. But the one thing that hasn’t changed was 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 attract a lot 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 in. This is 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 around it. 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 Twitter search, look for people asking questions about wine, and he would answer them. Those people would check out his profile, which linked back to his site, who would eventually start buying wine from his online store.

Is engaging 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 all of his tweets, Instagram posts and Snapchat videos. So if it’s good enough for Gary, it’s probably good enough for us too.

Be self-aware

Self-awareness in business is critical. 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 – what you are good at, and what you are not so good at. You want your employees to feel safe doing this, or it will never happen. This means sometimes hearing things that you disagree with or even upset you. Your job is to listen to the feedback, and thank them for bringing it to you.

Once you have listened to the feedback, it’s time to start focussing your energy on the things that you are good at, and delegating the things that you’re not so good at.

You’ve heard this advice before, most notably in Now Discover Your Strengths. But it bears repeating.

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 realized early on that if he was going to create content that was compelling to his audience, he would have to do it by video. So instead of focussing his attention on trying to become a better writer so he could create a “good” blog, he poured all of his energy into creating the best video content he could.

So when it comes time 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, which will almost always be where your talents are the greatest.

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 that there’s no way you can execute on that area at an A-level, even if you spend time improving, delegate it.

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