Gary Vaynerchuk: Thought Leader or Joy Stealer?

He says this a lot.

He says this a lot.


Gary Vaynerchuk. Gary Vee. Entrepreneur. Speaker. Marketing guru supreme. Reluctant Influencer. Loved. Strongly disliked. Misunderstood?

Does Gary Vaynerchuk need an introduction? Even if you’ve not seen any of his content then you’ll probably have heard his name in passing conversation or seen him pop up on your newsfeed.

I only began to engage with him relatively recently. Fairly late to the party considering he’s been a prominent voice for some time.

Since then I’ve consumed his content via his podcast, LinkedIn and YouTube channel on a fairly regular basis.

Gary Who-nerchuk??

In case you’ve managed to miss this shouty New Yorker and one of the most influential figures in modern business, here’s a quick overview:

Vaynerchuk rose to prominence initially as a wine seller and critic harnessing the latest technology and platforms, including YouTube, to grow his business.

In 2009 he founded Vayner Media, a digital marketing agency which has since scaled to be one of the largest marketing agency’s in New York.

From this position of influence, he’s developed an enormous international following of his own as a marketing thought leader and business speaker.

Vaynerchuk, often referred to simply as Gary Vee, has also become something of a divisive figure. Rather than cause for concern though I think this is an indication that he has something worth listening to, even if just to engage in the debate.

Gary is a classic case of chew the meat and spit out the bones. You don’t have to agree with everything he says (in fact I would actively encourage you not to) to get something out of listening to him.

There are some things I find really valuable in what he says and some not so much. I take a look at them here.

+ The hustle.

Unlike many business gurus Gary seems pretty real and down to earth. He doesn’t dress up entrepreneurship as anything other than what it is. Hard work.

If you don’t love what you do and aren’t prepared to get knocked down, slum it for a bit and generally get going when the going gets tough then going into business probably isn’t for you. 

If you really want something, you do have to work for it. In the real world, things rarely get handed to you on a plate and I agree with his criticism of a lot of modern education which seems to reward failure.

As someone who finds it very easy to coast and can sometimes lack motivation, having this sort of accountability from afar can be quite helpful. Sometimes it is time to put your foot on the accelerator. But…


- The hustle.

One of the main criticisms levied at Vaynerchuk is that he advocates an unhealthy lifestyle which involves working long days with little sleep, no social life and a beat-yourself-up-if-you’re-not-working-hard-enough approach to business.

Yes, working hard is important but this looks different for different people.

He denies advocating such a lifestyle, pointing out that the hustle is only for a select few that can hack it. However, that distinction isn’t always clear.

The reality is there aren’t many who can match his level of productivity. The idea that you need to put that much effort in and work 18 hours to get where you want to be is pretty punishing. And will probably lead to an early death.

It leaves no room for rest and assumes that your work is the only thing that can give you purpose in life. This may be true for some but not everyone and not for me. 

It’s important to recognise how you can scale the concept of working hard to your life. Stepping outside of your comfort zone is vital to achieve goals but this doesn’t mean having to be in a state of continual discomfort. Only you can decide where the level is. Not Gary V.

When you hustle too hard. Take care of yourself.

When you hustle too hard. Take care of yourself.


 + Money won’t make you happy.

Gary is pretty adamant that he is not driven by money but rather the process of making it.

Success for him is doing what you love doing for a living and not how much of a living you make.

This is a healthy way to look at it and I think the reminder to not pursue money as a goal is important. If that is what drives you, you’re more likely to quit when it gets tough.

- The pursuit of happiness can be just as draining.

I’m sure Gazzer V is pretty happy in general. He runs an enormous marketing agency and travels the world doing what he loves. It sounds like he has a loving and supportive family and millions of people look up to him. 

But happiness is fickle and changes with the weather. No matter where you are on your journey it’s not always going to be rosy. 

It’s possible that in desperately searching for the elusive happiness, you don’t find it and become burnt out because you haven’t got ‘there’ yet.

Contentment, to me, seems a much better goal. Being content with wherever you are on the journey is going to be much more satisfying.

Don’t beat yourself up if you’re not having a great day but accept that it’s part of life.

gary v quote 2.jpg

+ The charisma.

Gary’s confidence and conviction whenever he speaks publicly is admirable. I don’t necessarily love the way he speaks but he gets the message across.

He’s clearly an intelligent guy and understands when to contribute his voice. He pointed out in one podcast that the reason he often interrupts people is because he knows what they’re going to say. Time is limited so he may as well answer the question they’re going to ask. Arrogant? Possibly. Efficient? Yes.

I like the way he controls the room and ensures that the most value is extracted. Who needs waffle?


+ He knows what he’s talking about.

I have definitely found a significant amount of his content useful and will continue to listen in to see what he has to see.

If you listen to enough of his content you do start to hear the same things and it becomes apparent that one man can only say so much after all. But this is more to do with the fact that he seems to fixate on certain topics for a time. Something new will come along eventually.

His content model of documenting things, creating content around that in different mediums and subsequently distributing across platforms seems to make sense.

If you get enough of your stuff in front of people’s eyes they’re going to notice. There’s no denying that this (or something like it) is an effective way of marketing your business today.

This is freely available online.

This is freely available online.

- 100 pieces of content a day!

There is no way I or anyone other than him could match the level of content he puts out.

In one podcast he talked about ideally putting out 100 pieces of content a day! That to me seems ridiculous. The reality is he has a team of people around him helping him to document, create and put this content out.

Theoretically if you are a business with a big enough team or the budget to employ an agency then this might be possible.

For a smaller business or freelancer to do their job and put out content on this scale is laughable and unhelpful.

Admittedly Gary and his agency VaynerMedia aren’t targeting small businesses. The companies he works with are Fortune 500 so his content model is probably relevant but again I’m not sure the distinction is all that clear.

Where achieving quantity AND quality isn’t possible, I think aiming for quality is still a better route.


So, there’s some meat and some bones.

There are actually a few other things that I like about him including the way he values good parenting and his gratitude for the positive ways they’ve impacted his life. But this article is long enough.

Do you consume Gary V content in any form? What do you think? Is there something here you hadn’t thought of or disagree with?