The 3 Biggest Takeaways from My Time with Gary Vaynerchuk

Kav and GV

I have been getting a lot of questions regarding my meeting with Gary Vaynerchuk over the weekend and wanted to share my biggest takeaways from my time there.

One of the first things I took away from this weekend didn’t actually come from Gary himself, but from the other attendees. I was a little surprised at the end of the day to hear what people had gotten out of the whole thing while talking back and forth with each other. A good amount of the people there were saying that it was a lot same stuff that they’ve heard him talk about before. I personally think that those people missed the message. It’s funny because it’s almost the same problem I see in the fitness industry. Everyone wants to know what “the next best thing is” or hear some new secret that no one has yet. Instead of focusing on what has been already proven successful and how they can actually go about implementing those things. Successful people usually say the same things over and over again. But it’s because they know what works and like Gary repeated over and over. “It works every time”.

Here is some of “the same shit”

  1. Hustle
  2. Focus on your strengths
  3. Don’t sell what you don’t do
  4. 99% of things don’t matter.
  5. Say what you want but Back it up every time.

Here are the 3 things I got out of my time at Vayner.

Positive vs. Negative

I’ve followed Gary for a while now and seen a lot of his content and interviews. There’s no doubt in my mind now that he is allergic to negativity, whereas I thrive in conflict. I found this very interesting because even though we have different approaches to the way we see things, the message in the end is still the same. Gary takes a very positive approach toward everything and it ultimately is what helps him inspire so many. I take the negative things and try and turn them around on people to get them to see what is holding them back, then change those actions in order to be successful. Both options work. The power is always in your hands to go change things. It’s just a matter of staying true to who you are and make sure that you are so genuine that is passes through to your audience with your content.

Walk into a room with a Blank Slate

One of the questions that was asked this weekend was, “when you walk into a room with a CEO or President of a company what is your mindset or gameplan?” The first thing I thought was Blank Slate. Sure enough Gary’s answer was “I walk into the room blank.” He wants to talk, read their reactions, then listen. He’ll read the other person’s reactions to his statements and then guide them to where he needs the conversation to go. Some people are silent so they can listen but Gary “talks to hear”. That sounds like an oxymoron but he is so in tune with your reactions that he can sense your feelings and move the conversation in that direction. He’s constantly listening by reading you.


I was very impressed at how someone could be so adamant about their way of doing things yet not judge anyone else at the same time. He made it clear without ever saying it that each person’s circumstances are what determine their own process. He might disagree with their process but doesn’t judge because their circumstances are their own. Context is everything. If I was personally checking off boxes comparing myself to him this is the one that would be empty. I just don’t have that right now in my life. It’s hard for me to be empathetic towards others. I watched him destroy a woman’s business process and everything she does yet in the same breathe showed so much empathy to her situation. Remember CONTEXT IS KING


His team is driven by talent. He doesn’t have any predigest to your background. He only cares about how good are you now, and how quickly you want to be damn good. A+ talent x hard work adds up to some really good content. And Gary has built a dream team in that area. DRock is no just run of the mill videographer. He knows Gary’s moves and understands the viewpoint to capture the story. Gary is always creating but DRock isn’t just documenting he is creating as well. He may not understand all the processes at the level of detail that Gary does. But he knows how to capture the essence of the story and reiterate to everyone else without ever being in front of the camera. I also spent some time with Alex, he assisted Gary with the setup of this meeting. Down to earth and always looking to make the experience great without trying to steal the show. I bet that if any one of Gary’s team members were on their own they would be wildly successful in their own right. Now put them all in the same room with Gary as the Captain and you have the make of a Billion dollar Machine.

How did I get here?

When Gary launched his latest book #AskGaryVee he also ran a 3 book promotion for an unknown surprise. I already purchased a number of copies but felt the value has been so great to me that I could grab a few more to give to others. Gary told a story about when he pre-released his book “Crush It”. They sent a thank you box out to everyone who ordered for that promotion. He is constantly going over the top so he thought “Ok what is it that people actually want?”. People want access. So this time he gave it to us. He gave us the thing that is most valuable to him and everyone in the room, his time. Gary changed the world’s mentality on what you can get done in a 5 minute meeting and yet gave us well over the allotted time. His entire business is driven by gaining attention, and he gave us his attention for 2.5 hours. You can’t put a price tag on that. The easiest thing he could have done was send us a gift box, say thanks or give us a shoutout. But he did what was the greastest value and that was give us an extended period of his time. All in all it cost me about $61.17. But for 2.5 hours of the best marketer in the world’s time you can’t beat that! I was honored to be able to come and learn from one of the best businessmen in the game.

Be Your Best,

Coach Kavanaugh