Gary Vaynerchuk and the Older Woman

“The truth is: Belonging starts with self-acceptance. Your level of belonging, in fact, can never be greater than your level of self-acceptance, because believing that you’re enough is what gives you the courage to be authentic, vulnerable and imperfect.” ~ Brene Brown

Who is Gary Vee?

I first heard the name “Gary Vaynerchuk” in a podcast in early 2016. Like all good marketing ‘targets’ I needed to hear his name about seven more times before I finally decided to figure out who he was. The podcasts that had mentioned him all talked about him in venerable tones… the king of social media and social media marketing. The master of the vlog. An omnipotent and hugely successful investor in fledgling social media platforms. And the guru of picking the next hottest internet trend. Given the credibility and influence of those who were name dropping him, I had pretty high expectations.

Authenticity Confidence Brown

So I watched #AskGaryVee and I was deeply disappointed.

He spoke too fast (he has a brash New Jersey accent), swore too much and was disrespectful of everyone and virtually everything.

I honestly thought he was an overhyped idiot with nothing to say.

All flash and no substance

Needless to say, I didn’t listen or watch any more…

Roll forward about twelve months, and a strange and unexpected thing happened.

Another podcast showed up in my feed: Chandler Bolt – a softly spoken guy with a charming southern drawl – was interviewing Gary Vee about his book Jab, Jab, Jab, Right Hook.

Now I like Chandler – and his podcast is about self-publishing – so I thought I’d hear him out, despite my reservations.

And it started pretty much as I expected. “Me me me… blah blah blah…” He was even happily pointing out how happy he was with traditional publishing – which is kind-of anathema to the point of Chandler’s podcast!

Then about nine minutes in, Gary said something that gave me pause…

“…I had realised that I was at my best and people thought I was the smartest, and I was the best version of myself in Q&A form. Every keynote I ever gave, people were entertained but 20% of the audience didn’t like the cursing or the ego, but in the Q&A they were like – this guy might be smart… Q&A was shedding the best light on me.”

He went on to talk about how what he has to say (effectively, “work hard if you want results – no shortcuts”) isn’t sexy or cool or interesting, and Chandler asked him “how do you make it sexy?”

“My charisma. My personality. My showmanship.  And again… for seven out of 10. For three out of 10 it’s too much, it’s too New Jersey, it’s too irreverent… And I respect that and I don’t disagree. I have empathy and self-awareness of how I’m being consumed. I know that the reason I win net-net is because I have the right intent.”

The right intent…

Authenticity Confidence Vaynerchuk

He goes on, in a genuinely self-deprecating way, to say that he realised early on in life that he had a very narrow skill set, and he doubled-down on that in a big way. He plays to his strengths, he doesn’t try to be someone he isn’t – and he knows that this means he won’t appeal to everyone… Particularly women over a certain age… (yes, guilty as charged!).

Through the remaining 25 minutes of the podcast, I was enthralled. I started to see his bravado and obnoxious demeanour in an entirely different light… That of someone who has become exceedingly successful by deeply understanding what his skills are, ‘owning’ his limitations and the consequences of those skills, and learning how to Crush It with authenticity and confidence.

Confidence, Authenticity and ‘Faking-it’

This really started me thinking about the relationship between confidence and authenticity.  And also about that old and persistent piece of advice “fake it till you make it”.

Can you ‘fake-it’ to feel confident? Or does the very fact you’re acting in an inauthentic way undermine your confidence?

What impact does your intent have? If your intentions are good, does that create authenticity even if you are faking it?

And what wise counsel and valuable insight do we miss when we ‘tune-out’ someone who doesn’t immediately appeal to our sensitivities and social norms…?

I’d love to hear what you think – let me know in the comments below.

Listen to Chandler & Gary’s interview here.

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4 thoughts on “Gary Vaynerchuk and the Older Woman”

  1. It took me quite some time to come around to writing the comment I promised, but here it comes (It is adapted from a rather lenghty and not very well formulated post at
    Some years ago, when Denmark participated in the EXPO 2010 in Shanghai, the winning project had as a key element the original statue of The Little Mermaid, inspired by the fairy tale of Hans Christian Andersen, which was to be moved to the Danish pavillion in Shanghai for the duration of the exhibition – because if there is one thing we Danes think people recognize as Danish, it is the fairy tales of Hans Christian Andersen.
    During the time when there was much discussion about whether moving the statue should even be permitted, I heard the architect who was behind the winning project telling that actually, their vision had been to let the statue enter Shanghai harbour as figurehead of the world’s largest container carrier (at that time, the “Emma Mærsk”, which belongs to the Danish ship broker company MAERSK, another of our national treasures).
    And initially I thought – this man is crazy: in a time where there’s much discussion about whether the statue should even be allowed to go, he puts up this story – what would people think? That he is totally out of touch with what goes on?
    But then it dawned on me – of course, he does not care about what “people” think. He is not interested in having John and Jane Doe come to him, when they need a new tool shed in the garden. He is interested in large visionary projects for people who like exceptional visionary architecture – and this target audience would actually love him showing that he is able to come up with wildly creative ideas.
    So I think the point is: regardless whether you’re an American author or a Danish architect – it’s the fact that you are able to put forward your message to your target audience (or a sufficiently large target audience to make you able to not care about the rest) that makes you a good communicator – then the fact that the message comes across in a way which does not resonate well with you, me, John or Jane Doe or the public in general is of less importance.

    • Hi Henrik
      This is great! It’s a brilliant parallel – and always helpful to have another example in a different context.
      I actually studied architecture, so this is particularly pertinent for me!
      I never completed the degree as I became frustrated by how impractical aspects of the profession/study were.

      As always, your feedback is greatly appreciated!

      • Strangely enough, I have always been attracted to architecture – though I am pretty sure that this might only be because I can have a con amore attitude to it – if I had had to study it in all its aspects, I am afraid it would be an entirely different story for me as well. But now, I am able to appreciate it, just as one appreciates art.
        And after all, once I read somewhere (I unfortunately cannot remember where) that “Good architecture is to the eye, what music is to the ear” – I think that’s very true. Taste may differ, but it is possible to delight in entire compositions or particularly beautiful details in both.
        (By the way, all of this made me think back at an interesting old anecdote on architecture and confidence – I’ll see to that I have it translated one of these days)


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