Gary Vaynerchuk is a multi-faceted entrepreneur, New York Times best-selling author, and sought after public speaker. In 2009, he was crowned the “Innovator of the Year” by Wine Enthusiast magazine, and became a part of Decanter magazine’s “Power List” of the most influential figures in the wine industry. Gary has become famous in part for his effectiveness in reaching people through social media, so much so that he once hit the Facebook friend limit and is about to reach the million follower mark on Twitter. Gary’s content is available through two websites Wine Library TV and GaryVaynerchuk.com. Gary’s newest book Jab, Jab, Jab, Right Hook: How to Tell Your Story in a Noisy, Social World about social media marketing strategies is available for pre-order and will ship by the end of the year.


1) Other popular thought leaders such as Tim Ferriss and Chet Holmes make reference to really working hard on establishing a base of advocates (1000 True Fans, The Dream 100, etc.)… and I get the sense that you recommend acquiring this type of loyalty more organically through authenticity rather than methodology… would you say that’s a fair statement? And if so, why do you choose authenticity over methodology?

I don’t really know Chet, but I think Tim really likes people and interacting with them a lot so I believe he would tell you, as I’m telling you, no one advocates one of these over the other. I’m well known for how much I like engaging with people. I think Tim is a brilliant operator and thinks more about the strategy of this stuff. I think about strategy as well, but I think it’s fair to say I’m a little bit less concerned with my time than other people are. I believe in the serendipity of it all, I believe personally that making myself accessible has a lot more value for me than others. I think the real answer to your question is there are a lot of different ways to skin a cat. There are a lot of different ways to build brand advocacy and both methods can work. I think what Tim and I have done extremely well is become really self-aware. People who know what they are good at and then execute against what they do well… they are the ones that win. Tim is more organized than I am, and that works for him and he gets a lot of upside out of his organization. I can’t even begin to sit down and get organized… but on the flip side I have the capacity to go 24-7, 365 days a year… I mean, here we are 9pm for me and I’m doing our interview. This is what I’m good at… everybody is different. I would never want to outsource my engagement, my interactions, or all the things that I know that I might be able to make more efficient, because frankly I get a lot of happiness out of them.

2) One of the reasons your teachings resonate with me so much is I too believe in the tenets of hustle and family. I’m a self-tracker so I was going to send you my sleep data but elected to spare you the minutia. We put my child to bed at 9:00pm, the wife goes to bed at 10:30pm, and then I crank until about 1:00am. I then get up at 6:30am and do it all over again (this usually includes weekends too). It doesn’t bother me because I love what I do, but I also love my family and as I get older I can tell that sometimes the fatigue catches up with me (regardless of passion). This means despite my best intentions I’m not fully engaged with my family during certain levels of fatigue. In your experience what successful strategies have you seen to help mitigate this risk and maintain balance despite the “hustle”?

I’m still very comfortable with the entirety of the message in Crush It! And here is why, if you read it you know what I am advocating is that if you are not happy with your life the only way to change it is to put in an effort that creates something else for yourself. I mean some people are going to need to spend that energy with their families… to truly crush it they need to spend more time with their families. In other words, what they need to do is spend less time at work. Here is the spirit of the message: I think that if you were not happy with what you were doing in 1977 you did not have a lot of alternatives. You had to pay the rent; you had to pay your bills, right? You got home from your job in the evening, and the best you could do is maybe moonlight at some other terrible job. Today if you come home in the evening and you are unhappy you have the ability to start a business online at night and work to create a scenario that could change your life. I still believe that to be a hundred percent true. Just like if you are unhappy with how much you work – well, then – go get a job that is less demanding and spend that extra time with your family.

So here’s my point, I’m speaking to the 90% of people that complain about their situation. And my point is if you are complaining about something, change it.

3) In The Thank You Economy you mention that companies that believe “caring” cannot be scaled do so at their own peril, but for solo entrepreneurs and SMB figureheads’ bandwidth will eventually cap. You’ve also mentioned before in jest that you’re great at building communication models that don’t scale. You now have an auto-responder for fans that email you because you simply cannot response to everything coming at you. As you begin to reach the limits of what is humanly possible what do you need to make sure – bar none – doesn’t get lost regarding the customer/fan experience? And, have you developed any tricks and/or can you recommend any technology that can help a person (like yourself) optimize the connection and rapport needed to maintain their respective fan base (regardless of size)?

I have an intimate knowledge about what I’m about to say which is one’s capacity for effort is usually grossly underestimated. So, yes I have already reached critical mass, but I am actually engaging more now than I use to believe it or not. I mean now I do an obnoxious amount of engaging. I think my one interview a day series is a good example of that. It is not scalable, but using our interaction now as an example I have to assume, unless I’m naïve, that you and I now have a deeper intimate relationship after this phone call than we did before. I was happy to strengthen that bond because I can tell you consume my content and you clearly know it. I think this is what it comes down to – I’ve been thinking about this a lot lately too – is that I honestly, genuinely, completely and utterly believe in what I talk about. I think the authenticity of that really resonates with people. I believe, actually I know, that when you are trying the world notes it. Some people are more efficient, more guarded, with their time. There are people much more strategic than I am… the only optimization I have now that I did not have before is more people to help me. That is still human though, I’m not automated. I’m serendipitous. I’m careless, but it’s my carelessness that has created my strength.

4) What is your take on the new crop of companies focused on optimizing against Net Promoter Score (NPS) and developing campaigns to exploit this type of success metric? Are there any new and/or established companies that, in your opinion, succeed at helping companies streamline and optimize their ability to foster advocacy aside from traditional social media channels?

I never signed up for a Klout account for that reason. Note not because I don’t like Klout, it is just for the fact I am very scared of a world where people try to con and/or figure out how algorithmically to build brand equity. I believe you need to give to receive. I understand why these types of things exist. There is some value to it to some I’m sure… but you know, I live at the crossroads of analytics and feeling. I would like to believe I have a high emotional intelligence.

There are so many ways to build your fan base and – again – the people I see win the most are those that are self-aware. I envy people that are more efficient than me, and in theory “achieved” what I have achieved in shorter periods of time. These are the folks that squeeze the most out of every minute. I envy it. On the same token, I think they should envy how deep and authentic my relationships are, and I believe that matters. For me the way I got there, and what I advocate, is putting in the work. So to try to answer your question… I believe in scaling the un-scalable, I believe there’s enormous magic in it. Especially as the world becomes much more efficient, and people buy more into the analytics and the “quant” it is a competitive advantage to be real. Authentic, consistent effort and going the extra mile are becoming less and less and less of the norm, these things are becoming more and more scarce. I think real, less automated, approaches will soon outweigh the methodologies that game advocacy because of the inherent value of authenticity.

5) I’m fired up for your new book, Jab, Jab, Jab, Right Hook: How to Tell Your Story in a Noisy, Social World… it alludes in the summary that the idea of just curating great content is not enough anymore. Responsive design and optimizing for mobile is now clearly more important than ever; without the luxury of intimate knowledge of your new book I ask: Have you been persuaded at all by the budding Lean Startup Movement – the entrepreneurial idea that passion alone is not enough anymore in today’s marketplace – that passion should be paired with a consumer-centric approach? Or, are you still a believer that passion and tenacity are the primary ingredients for success (i.e. creating and adapting to your market vs. finding and instructing your market)?

Go look at what I did with Wine Library TV and I think most would agree I lived “Lean Startup” long before it was written about by Eric Ries. I love Eric’s work. The spirit of it is don’t waste time, energy and money on things that do not move you forward. Be efficient. But here is where I think some people get it wrong. If success was easily quantifiable, if everything could follow a perfect blueprint… efficiencies were easily learned… everyone would be rich. It should be obvious to anyone however that if this was really true the game would be over by now.

In other words, if everything was about efficiencies and math and Lean Startups… success was all mathematically driven… the whole world would be over by now. Every single nerd would have all the biggest companies in the world. In my new book I make the case that there is a balance between creativity and analytics. I also believe social networks are required engagement platforms… they are necessary to understand and will be important tools with which to interact with your people and will be relevant for at least the next 36 months… simple as that. They’re state of the union on how to get your story across on the platforms that I actually think people are paying attention to right now. These platforms still cost little to no money to tell stories people will consume and resonate with, opposed to producing professional prefab content at a significant cost.

Can I tell you something funny before we finish? I would tell you I think a lot of my success comes from the fact that I’m undereducated. I think that me not knowing all the rules has made me guided by my own internal light thus making me unique enough in some way, some shape, some form, that it has made me fresh and interesting to other people. It’s my naiveté and lack of academic education that has made me in some ways break out because I wasn’t educated in the same way that a lot of my contemporaries are. Truth be told, the “Lean Startup” is called running a successful small business. The truth is hustlers don’t have any choice but to be lean. Too much funding and what’s your carrot? My family… we lived paycheck to paycheck. Anybody who follows me knows my story, what they don’t know is we were probably making a 10% gross margin at the store. We grossed three million which left $300,000 before expenses. We didn’t really make any money.

This is not something I have ever really talked about. This is one of the first times I have mentioned it in an interview actually, but it gets to the spirit of your question. It is kind of why I did this interview series, to say things I have never really said in the past. Look, true self-funded entrepreneurs are lean; for us there is no other option.

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