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5 Coaching Lessons From Gary Vaynerchuk with Karl Bryan

by | Karl Bryan

“Legacy Is Greater Than Currency”

A tech investor and rock star marketer Gary Vaynerchuk (Gary Vee) has invested in more than 50 startups, including Twitter, Tumblr, Medium, Birchbox, Uber and Venmo.

In today’s world of hyperbole and exaggeration, a 2000% increase could be dismissed as something others have achieved.

The difference is most marketers are starting from sales of about $5000 and raise 2000% (likely exaggerated). Gary Vee started at $3 million and grew his family wine business to $60 million. Predominantly through social media marketing, video and an unprecedented level of energy. 

That growth is insane.

What makes Vaynerchuk unique is how upfront he is with his decisions and execution. He releases daily videos on his YouTube with over a million subscribers and uses this platform to take followers behind the scenes to watch his daily activities and how he makes day to day decisions.

Here are five bits of coaching magic behind Gary Vee’s success:

1. Relevance

Gary Vee screams from the mountain tops that social media, mobile devices, video, and audio are the future.  If you want to stay relevant, you need to start investing time and establish expertise in these four key areas. Desktop impressions (a normal office computer) will steadily decrease whereas mobile (the phone in your hand, iPad’s, etc) are where the impressions are going.  Therefore, it’s critical to optimize your business for mobile.

When Instagram was relatively new Gary Vee praised the creators Kevin Systrom and Mike Krieger for being smart enough to create a 100% mobile app… and also for the creation of “Instagram stories.”

He similarly praised Snapchat for the foresight to create a video platform where users only had 24 hours to watch a snap.  The scarcity of that was absolutely genius… users had to constantly check in or miss out. They subsequently get billions of views per day.

He describes Snapchat as “the hottie at the gym looking for attention.”

Video on FB is relatively new and somewhere you’d be well advised to spend some time if you’re looking to attract attention (eyeballs) and local small business owners.

Lesson: To be successful in this day and age (increased competition for attention) you need to understand where your small business owners are and meet them there. Don’t make them come to you.  You also need to create products, programs and services for your coaching company.

2. Hustle Hustle Hustle

Gary Vee says hustle is the most underrated human characteristic there is.  He literally eats, sleep, craps and breathes hustle every day with his unprecedented work ethic and passion for his craft.  He starts his day with the roosters and often works until wee hours of the night.

He’s not just about crazy hours… his responsibilities entail running multiple companies, traveling, blogging, consulting, investing, looking after his family plus more.  He appears to love every minute of it which adds to his intrigue.

He’s famous for following up with every social media comment sent his way. Not only replying but using unique and insightful responses so the commenter feels understood and others viewing take notice. Personally replying humanizes your brand and passively encourages others to engage with you and connect.

Lesson: You should take one hour a day and actively engage and respond with people within your target market (presumably small business folk) on social media.If you’re not sure where to find them… get a list of local business owners in your local area (Chamber website, BNI website, local directories, etc…). Search their names and companies on FB / Instagram / YouTube and add them as a friend / follow them.

Yes, this will take effort and time. When they post a pic of their family, respond. When they post something about their business, respond/engage. To engage a restaurant… have dinner there and then post on the restaurant’s page that you and your family were treated like gold (if you were). Build a relationship (build 100 like this)… and you’ll be well rewarded and you’ll get much better at it!

3. Jab Jab Jab Right Hook

The title of Gary’s most popular book is “Jab Jab Jab Right Hook.” It essentially focuses on the concept of softening up your audience by educating them and delivering value before you go in for the “Right Hook,” and try to sell them. 

The more entertaining, educational and valuable the better… and its also important you work to a “call to action.”

This is particularly relevant for business coaches because it’s a polar opposite to the way most think and get taught.  Eben Pagan refers to it as “moving the free line.”

Instead of putting all of your webinars and whitepapers behind data capture forms, you should give some of them away as a sign of goodwill. Focus on hitting people with a series of jabs before you try to land that right hook and get people to purchase your coaching.

Lesson: Give insane value away for free (seminars, webinars, reports, consultations, 14 days of coaching where applicable, comments on social media, send private videos explaining magic) to build rapport and “get in the door” so to speak… then right hook them when they’ve softened up. Yes, this takes time and effort.

4. And….

Gary Vee often uses the question, “And?”

His point is that everyone has complaints, negative forces and situations they’re dealing with… so he’ll often abruptly cut people off to ask, “And, what are you going to do about it?”

If you have a room of 1000 people and you ask “Hands up if you like surprises…” Not surprisingly everyone puts their hand up.

But the truth is… they like the surprises they want… the ones they don’t want they call ‘problems.’

Lesson: Life is a series of problems.  They’re your opportunity to grow and your client’s opportunity to buy high-end coaching from you. Think about it… people with ‘problems’ spend money. Sickness, divorce, sense of dissatisfaction, unwanted birthday normally with a 5 or a 0 on the end of it :o)

A dissatisfied business owner buys coaching. A satisfied business owner doesn’t. No one buys the band-aid until they see the blood.

Do you have a strategy/process to create dissatisfaction when you sit with business owners?

5. Know Your Strengths

“I’m not a 6’9” man with stilts for legs and that runs like a cheetah… I, therefore, do not play basketball professionally.”

Gary Vee constantly preaches to recognize your strengths and to then concentrate on capitalizing on them.  Most people work out their weaknesses and spend time strengthening them.

A great business example would be Red Bull. They understand their market and therefore specialize in extreme sports.  They sponsor events, athletes, they share footage of extreme sports highlights and even create stunts like their epic space diving project with Felix Baumgartner. Also, the motorbike rider, Robbie Maddison, that jumped off the building on NYE in Vegas for 1 million dollars (if you haven’t seen this its crazy!).  The videos subsequently go viral.

You don’t need to look to space or jump off a building to specialize. If you’re a mortgage broker you can get a good mortgage fraud detection system in place and just specialize in a specific location. A realtor can become “The Water Front Guy” and predominantly sell houses on the water. An Italian owner of a restaurant becomes a Pastaria instead of a family restaurant.  Once you’ve specialized and are working to your strengths then this should be the basis of your content. 

Gary Vee found fame as “the wine guy” and look at how far he’s taken it. He is the guy to ask “what is a commercial wine cooler?“.

Lesson: You and your clients need to specialize. As a business coach, you should be creating products, programs, and events and promoting them. Not promoting the name of your company. Create a goal-setting workshop and promote it (rather than promoting your company name that no one cares about). A social media workshop. A networking and referral workshop.  Create a cheat sheet for marketing your real estate company in Vancouver and promote the heck out of it.

Well, there you have it…  five coaching lessons from Gary Vee. His best advice can be summed up in taking action.

All the blog posts, videos and articles like this can provide some knowledge and inspiration, but ultimately it’s about getting to work. Thanks to the internet there has never been a better time to get your voice out there and to make a difference. 


Thanks for tuning in,

Karl Bryan

Karl Bryan, creator of Profit Acceleration Software™  

Karl is the Founder and Editor-in-Chief of The Six-Figure Coach Magazine and Chairman of, home of the largest private community of Business Coaches (24 countries and counting) in the world. His goal is straightforward… to help serious coaches/consultants get more clients. Find out more at

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