A Radically Different Gary Vee Appeared After Spending the Day with Him

Tim Denning

What Gary’s change from marketing to spirituality can teach you.


Image Credit: kierankesner.com

I sat there puzzled as an audience member began explaining what he had seen change in Gary Vee in recent times. As a long-time observer of Gary’s work, it left me quite stunned. The member of the audience said:

“Gary, without spreading spirituality that is exactly what you are doing”

Everyone in the room went quiet and look puzzled. Even crazier was that Gary looked puzzled too. He wasn’t sure how to respond and the room was deadly quiet.

Gary Vee has been on the internet for a long time but only burst onto our phone screens with his obnoxious, brutal and hustle harder attitude in around 2014. Some people like Gary and others do not — although it’s hard to deny that what he points out is a message we all need to hear more of.

The original purpose of Gary’s message was to convince us to use social media and build a following. It was all around branding, marketing and whatever was the latest social media platform. He became well-known around the same time for predicting the platforms we would shift to and the sale of companies such as Instagram.

In 2017, I saw him speak in Australia and was impressed. In 2018, the need to see him tour again was lost on me and to experience the FOMO that comes with learning about the state of social media, was something worth avoiding.

All of that changed last Tuesday. Gary was live in Melbourne for The National Achievers Congress and the man that walked out was not the same person. Here’s what changed:

  • There was no big introduction
  • His voice was softer
  • He wore a beanie saying “empathy”
  • His body language was less animated
  • There were fewer swear words
  • He had a level of care that I had not seen before
  • He had shifted to studying human behavior
  • The tools of social media have been demonized and he felt it his obligation to speak out on the subject

The change in the way Gary answered questions was fascinating. He looked the person in the eyes, knelt down to be on their level and was slow to respond. There were times he would give his answer and the person asking the question would say thank you, not realizing that Gary had more to say and would continue on after some thought.

There was a level of determination to truly give advice and a perspective that would help rather than give the audience a show.

He was never finished with his answer until he could physically see the shift in the person asking the question. It didn’t matter how long it took; he was obsessed with making people feel him, not just hear him.

The shift in Gary Vee from marketer to something that is not only different, but far more relevant, was a stark one.

Here’s what Gary taught me:

The same answer to every question

Gary’s keynote was about ten minutes and then he went straight into allowing the audience to ask questions.

Gone are the days of Gary talking at audiences. His new obsession is for listening or as I once wrote “The Power of Saying Less.”

At one point, Gary said, “Every answer I am giving today is the same.” And he was right. All of the answers he was giving to audience members were tied back to either insecurity or judgment.

The “hustle harder’’ and produce content message was absent because he’s worked out that no one is taking action on this advice and the core of people’s problems lie in human psychology/behavior.

https://img.particlenews.com/image.php?url=1TJYld_0XwdBhbd00Image Credit: Getty Images

We don’t take action or get the result because we are deeply insecure or are afraid to be judged. When we can take a step back and look deeply into these areas of our life, we can find a way to move past these two giant obstacles.

Every time I publish an article, there is the same fear of judgment and beneath all of that is a layer of insecurity that, perhaps, I am not ready to face. For now, I just hold my breath and try to ignore it.

What Gary said hit home. We don’t need more skills or to post more on social media: we need to look at our psychology and the parts that are holding us back like insecurity and judgment.

“Perfection is a disguise for insecurity”

This realization was what led me to begin to see the change in Gary.

Another layer deep

Once Gary touched on our fear of judgment and our insecurity, he then went deeper by talking about our self-esteem.

Low self-esteem is what is leading to us not taking action in business, being afraid to share stories, having problems with money and not knowing what to do with our lives. Social media has amplified these issues with our self-esteem and the real work we can do is to address this issue.

This is the first time I have heard Gary talk about self-esteem instead of focusing on the tools of business. The human tools are scarier and reveal the flaws in us that we have been ignoring. This is Gary’s new perspective.

The tool that has MADE Gary Vee, has caused him to question its role, and the future

If it weren’t for social media, none of us would know who Gary Vee was.

Gary has been a huge promoter of social media and the by-product is that he has become a huge consumer of the platforms, conversations and cultures that have been created by it.

For the first time, I saw Gary question social media. He joked:

“Technology keeps advancing until the robots kill us.”

This was his light-hearted way of starting the conversation. In his role as a technologist, he has seen the rapid changes over the last three years more than most people. The job roles humans have and the skills we need for the future have changed and Gary is pointing this out.

The advice he gives is to look closer at the softer side of who we are and our human nature, because the easy stuff — manual labor, lazy work, complexity, short-lived arbitrages — are being replaced due to the role technology plays in our lives.

The old Gary was about the tools; the new Gary is about what the tools are doing to humanity and their purpose in life.

Demonizing technology

“The internet doesn’t care what you look like and it’s free, and still you find ways to complain,” says Gary.

He was clearly agitated by the recent demonizing of smartphones and social media as being the cause of our problems.

“Social media exposes us; it doesn’t change us”

The problems would exist regardless of the technology and he believes demonizing it is a weak excuse that is not the heart of the issue.

Mental illness and social media

An audience member asked Gary if social media affects his mental health.

He says it hasn’t negatively impacted him because he has focused on his psychology and mindset rather than taking the easy way out and blaming the tools which each of us are responsible for controlling our usage with.

This quote summed up his thoughts perfectly:

“Instagram didn’t make you insecure; you were already that way.”

We can’t clearly solve the issues related to mental illness unless we take back the responsibility and stop looking for an easy way out like blaming social media. The problem is much deeper than that.

From marketing to psychology

Gary would typically respond to questions four years ago with marketing advice. He would give out strategies and coach people on how to use the tools and the best tools for that time period.

The Gary I saw recently spent no time talking about the tools.

Every conversation he had with the audience had an element of psychology. His focus wasn’t on the problems, but how we’re thinking about the problems. I found this change in theme more valuable and the people sitting around me had similar thoughts. It is clear that if the answer to all our business problems was as simple as marketing, we’d all have taken action and done it already.

The answer to business problems, as highlighted by Gary, is psychology and our own thinking.

Care about the community, not the ‘likes’

One point Gary wanted to make loud and clear was that we need to care for the people we are interacting with online. Social media is a conversation tool and the dream of building followers has been lost.

His tip for being better at social media is to be more social on the platforms.

The easiest way to do that is to reply to people’s comments and be empathetic in your approach. The addition of empathy was yet another subtle change to Gary’s advice.

The ecosystem has become selfish and that needs to change

“The audacity of ‘likes’ is selfish and the reason you are not winning”

This is one point I couldn’t agree more with. Social media is not about you and your brand. Chasing likes and thinking that you need to have your life validated by the crowd is a real issue.

The key to life (and the internet) is to move away from selfishness and more in the direction of selflessness. This is another example of Gary’s spiritual side coming out.

Selfishness leads us to worship material/physical things rather than being focused on the human spirit and becoming a better person, who can in turn, help more people.

Frustrated by excuses and empathetic at the same time

There was clearly no air time for excuses in the questions Gary was asked.

From a distance, it looked as though Gary might have been frustrated with the excuses that were appearing in conversations, yet when I looked a little harder, I could see the empathy in his eyes.

It is easy for someone in Gary’s position to judge, but watching him see himself in other people’s problems, and deeply care, was one of the highlights of seeing him in-person.

There is no substitute for empathy. It brings you closer to everyone you encounter.

The meaning of entrepreneurship

The idea of entrepreneurship has been lost somewhat in the bragging rights that we now have online.

It’s far too easy to think business is straightforward and simple. It’s not. The key meaning of entrepreneurship is this:

Entrepreneurship = Living life on your own terms

Gary says with a lot of passion in his voice that when you look at business through this lens, you’ll realize that what you are asking for is never going to be easy. It’s one of life’s greatest privileges and it is an enormous struggle.

Seeing Gary address the idea of entrepreneurship and being real about what it is from a different point of view, was radically different. Finally, someone who has done it is talking about what it really looks like.

You must know the why

The way to not have it all is to be blind to your why. As the shift towards being more spiritual has occurred with Gary, he has also become more philosophical.

He has begun questioning not only his own why, but the why of people he is trying to help.

We easily fall into this trap of living on auto-pilot and doing the thing we think we must do (like social media) without asking why and tieing it back to something bigger than ourselves.

Patience by example

A young man in the audience asked him to be a guest on his podcast and Gary said no — not to be a smart ass but to teach patience. He said:

“Email me in a years time and mention this event, and I’ll go on your podcast.”

This was Gary again tapping into his spiritual side and teaching patience. We want things far too quickly when we haven’t learned this. I have shared this lesson many times when asked about my success in writing and usually replying with “It took 4–5 years of getting nowhere, first.”

Patience is resisting the urge to ask for things you haven’t earned.

The #1 trait to look for

When asked what he looks for in people, Gary says, “humility.”

“It takes humility to feed creativity”

This an area I have also become obsessed with lately because without humility, your ego steps in and blocks you from reaching people on a deeper level. Too much ego is ugly, whereas humility shows people who we are and that they too matter.

If you’re looking for one skill to study, let it be humility. Humility will make you more likable than any social media post.

The speed of a decision is more valuable than the debate

Decision making allows us to act and it’s in our actions that our life is defined. Advice on decision-making can, therefore, make a drastic change in your life.

Gary says he has got good at making decisions because he is unemotional about them. When a decision doesn’t work, he moves on quickly.

When you make decisions, don’t dwell on them because the swift action produces greater results than getting stuck in the process and making a slow decision — or worse, no decision at all.

When you story tell, it’s your truth

This is why I’m obsessed with storytelling and Gary reminded me of this fact.

The example Gary gives is that when a rapper releases their first album, it often sells the most copies than their later albums, because it is them speaking the truth before it is clouded by all the success.

The power of storytelling is speaking our truth and letting it set us free, and then helping others to do the same.

Gary has shifted away from being a marketer because it has allowed him to speak his truth and share what he has really learned, which is nothing to do with technology or social media tools.

Creativity is subjective

No one is right or wrong.

There is no magical piece of writing, video or picture — all of it is subjective, so don’t be obsessed with making mass-market masterpieces that aim to be perfect. Target the people you believe you can help instead, who will understand your creativity.

You never know what will work

“People are scared to lose 3–4 years of their life,” Gary says.

Trying to predict the outcome is an unhelpful pursuit because you will never know which angle will work in your career or life. Being patient with the process and seeing 3–4 years investment in something that doesn’t work out as experimentation and learning, rather than wasted years of your life, is the psychological shift that makes a huge difference.

The obsession with looking for ‘hacks’

The hardest part about watching Gary Vee was seeing the ending of his time in Australia. As the event wrapped up, many people flocked to the stage to get a selfie with him when they hadn’t been given permission.

I spoke to a few people around why they wanted a selfie with him and it came down to one belief:

If Gary was in a photo with them or accepted their cold pitch, they would have a quick way to blow up on the internet and maybe go viral.

Getting a selfie with Gary was a hack to skip the queue and avoid putting in the work. All I can say to anyone reading this is to put in the work, don’t look for shortcuts, and explore your psychology the way Gary has.

When you unlock your softer side and what it means to be human, you won’t need hacks or shortcuts — because people will be drawn to you and guys like Gary will be reaching out to you, not the other way round.


The reason Gary’s transformation is so interesting is because when you reach what you think is success, a similar progression will happen in your life.

My mentor Joel has had a similar transformation and the same has happened to me. I started writing in 2014 about being ‘Addicted To Success’ and now most of what I share is around how to be a better human being, embrace humility, move away from selfishness, being kind and genuinely caring.

If you asked me whether I’d ever be writing about that at the start, I would have laughed.

There is a lot you can learn from Gary and his success, and I encourage you to embark on your own transformation. Start doing what you love and the spiritual side will appear in your life too the way it has for Gary.

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Aussie Blogger with 100M+ views — Writer for CNBC & Business Insider. Inspiring the world through Personal Development and Entrepreneurship www.timdenning.com


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