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SitePoint Podcast #42: Interview with Gary Vaynerchuk

By Kevin Yank



Episode 42 of The SitePoint Podcast is now available! This week, Patrick O’Keefe (@ifroggy) rings in the new year with author and entrepreneur Gary Vaynerchuk (@garyvee), who offers up some advice to help you get off to the right start.

A complete transcript of the interviews is provided below.

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Interview Transcript

Patrick: January 1st, 2010. Author and entrepreneur Gary Vaynerchuk helps us ring in the new year with advice to help you get off to the right start. This is the SitePoint Podcast #42: Interview with Gary Vaynerchuk.

Patrick: Hello and welcome to another edition of the SitePoint Podcast. This is Patrick O’Keefe and I’m alone today as I interview Gary Vaynerchuk. Gary is an author, speaker, and entrepreneur who took retailer Wine Library from a $4m business to a $45m business in just five years. Along with brother AJ, he runs VaynerMedia, a brand consulting agency that focuses on social media. He’s also the host of the popular online video show Wine Library TV, and the author of Gary Vaynerchuk’s 101 Wines, and Crush It! Why Now Is The Time To Cash In On Your Passion, the latter of which is the first in a ten-book deal he signed publisher Harper Studio. He video blogs at, but on Twitter he’s known simply as @garyvee.

Patrick: Hi Gary. Welcome to the show, thank you for joining us.

Gary: Thanks for having me.

Patrick: Well, we’ll get right down to business then. We’re at the end of 2009 now so we’re kind of taking stock of, I guess, what we’ve accomplished. What has this year meant for you?

Gary: You know I think it was a big transition year for me. Globally, at the most important level, I had a child, little Misha, a little girl back in May. So that’s obviously by far, the biggest thing that happened to me this year.

Professionally, I think it became a year where more people looked at me as more of a media business guy than just “the wine guy”. Obviously Crush It! came out, so becoming a best selling author is a really cool thing and so those two things really stand out.

Obviously launching VaynerMedia was a big deal and I’m excited about that.

I would say those are the things that really stood out.

Patrick: Cool. Congratulations on all of that. My220x in the SitePoint Forums asked this question. He wanted you to go back to when you first started to get serious about growing your business through social media. What was your first experiment? What was the first thing that you tried in social media to promote your business?

Gary: I guess it all depends on how you define social media. I was very much active in wine forums and wine blogs and I guess that was the web 2.0 movement. I guess if you define social media of more some of the Twitter, Facebook stuff; I started using Twitter in January of ’07 so that would maybe be my first foray into that.

So it really just depends on how you define it. I mean I think answering your email has the principles of social media. I guess definition becomes imperative here but what I understood was that the Web was becoming more connected than we had ever seen before and that’s kind of what I focused on.

Patrick: Oh yeah, forums are totally social media. I wrote a book called Managing Online Forums and it’s funny because they are sort of like not the backbone, but sort of the foundation of social media in a way.

How did you apply or how have you found it to be different from those early days on forums and blogs to some of these newer buzz brands or social tools that we’ve come to know today?

Gary: I just think that more people are involved and by virtue, the more people that are involved, the bigger the whole game is, right?

Patrick: Right.

Gary: And so I think that stands out to me that with more people involved, everything is becoming so much more scalable. So just the fact that more people are in the game, everything is so much more accentuated and grows to such bigger levels and I think that’s very imperative and important and exciting to watch.

Patrick: SitePoint cofounder Matt Mickiewicz, a friend of yours I believe, threw out a few questions for me and I’m going to ask them now. His first question for you was – How can individuals in the services business like consulting, design, development leverage social media to their benefit?

Gary: I think social media is all about listening, right?

Patrick: Right.

Gary: I think it comes down to listening. There’s a whole lot of talking going on out there and if you open up your mind and are willing to listen, I think you can really do a lot of damage and I think that any business should be creating content and listening. That becomes the blueprint, create great content and give customer service. It’s very basic but there’s way too many people not creating content and there’s way too many people not listening and when you combine both, you win.

Patrick: Right. Is perfection the enemy of progress? You’re famous for uploading your shows without editing and it hasn’t really hurt your viewership. What do you think that means?

Gary: I think it means that real and authentic and content always wins. Content doesn’t have to be polished to win. Contents can be content, right?

I mean there are people that love guys who wear suits and ties and there’s people that love guys who are in jeans and t-shirts and they both work, right? And so I focus on that; I think there are different ways to skin a cat.

Patrick: You’ve taped for the past two years or so without skipping a beat and you’ve discussed how the viewership didn’t come right away for you, how it took you some time.

How should entrepreneurs stay motivated if they don’t get the result they are looking for? We seem to live in a society of instant results where people expect something within a certain period of time. If they don’t get it, then they’re deflated and they give up.

Gary: I think people just have to recognize it takes time. You don’t build real multi-million dollar businesses in 45 minutes. It blows my mind that people kind of think that you can and that’s pretty much it. I mean nobody built businesses in five minutes in the past and this is not going to happen in the future either. Things can scale quicker, things can happen quicker but it’s not going to happen. I mean it’s just way, way too many people are completely blindsided by what’s really going on here and what’s going on here is that people are building real business and they take time. You just can’t build in five minutes, you just can’t and if you don’t have the patience, you’re going to lose because patience is by far the most important attribute in building a big business.

Patrick: I guess that’s maybe sort of the downside of the great American or the great success story. It motivates a lot of people but then the perception is that it happens overnight, right?

Gary: Yeah, there’s no overnight success. You’ve heard so many people say that, it’s so darn true. I mean it’s just not out there. It’s just not out there. Show me somebody who did it overnight and I’ll promise you that I can prove to you that it wasn’t done overnight. The end. It’s really that simple, you know?

Patrick: Last question form Matt – Aside from Crush It!, do you have any favorite business books that you would recommend?

Gary: You know this is where I have to be massively authentic; I don’t really read business books at all. I just don’t. I’ve read like four books in my whole life. I know Gladwell and Gauden and all these guys but I’ve just never read the books and so I can’t recommend a book because I’d be a fraud if I was to make one up.

Patrick: Right, there’s nothing wrong with that. I think for me, I run a network of websites, and I didn’t really read any books on… I’ve never read a book on like HTML or any of these things that you need to know to run a site; I just kind of did it. Experience is as good a knowledge builder as anything else.

Gary: Listen, I wish I did read more because I guarantee I’d know more. I’m not naïve to not understand that I would miss out on not being in the trenches. The fact of the matter is though I spend so much time with my fan base, that’s regurgitating and getting emails and interacting. That’s kind of where my learnings are done and blogs and things of that nature.

Patrick: And I think that speaks to the need to actually do things rather than just read about them and learn them to actually get out and experience something and that’s something that I think you talked about in the book too.

Gary: No question.

Patrick: @JosephHurtado on Twitter wanted to know – How do you go from a barebones idea to startup to working business? Kind of a general question but any thoughts would be appreciated.

Gary: You know, very general, I think you got to not worry about the idea but understand the execution involved. I think the execution involved is something you need to stress and pay attention to way more than the idea. I think way too many people get caught up in the idea and I think that that is an issue and it hurts people. I think the ideas are fine but they’re a dime a dozen. It’s can you see a very clear plan of execution that I think more people should pay attention to.

Patrick: It reminds of a video by Ze Frank called Brain Crack. I don’t know if you seen that or not but basically, the idea is that people get addicted to brain crack, to the love of their own ideas and how beautiful they are and they never actually go out and accomplish anything. Does that resonate with you?

Gary: Yeah, I think there’s a lot… you know Ze is a smart guy and he thinks a lot about those kinds of things and I think there’s a lot of value to what he’s talking about there because I agree with that immensely.

Patrick: @godonholiday on Twitter wanted to know – How important in your eyes is the look or design of a website?

Gary: Imperative. If you read Crush It!, it’s the only thing I can tell people to spend money on.

Patrick: Speak to that. What are the things that people spend money on that they shouldn’t when they should put it toward design? What are some of the bad things they spend money on?

Gary: Early on, SEO, buying AdWords, spending money on traveling to places where they think they’ll get value. I think you put your head down, you have a great design, and you make sure your website is right, that’s your home and put your head down and hustle and get involved in the community you’re a part of and that really becomes what you need to do.

Patrick: As a follow up to that, what would you change on your own site?

Gary: Quite a bit. I think I’m doing a lot of things wrong from the site. It’s actually one of the biggest things I’m thinking about going forward and so I would say a lot. I just haven’t looked yet but quite a bit.

Patrick: Dennis on Facebook wanted to know – What advice you would provide to midlife career changers in this economy.

Gary: Recognize that we’re living through a different time where you can do so much now by executing in the social media sphere and then in the new Web. The internet is maturing. It’s only 15 years old. The opportunities are endless and you’ve just got to jump in there and take a look at it.

Patrick: Molona on the SitePoint Forums said you’re big on passion but how do you cope with all the things that can turn the passion down, such as annoying customers, non-paying customers, annoying providers and so on and any other stuff that makes you want to throw your computer in her words “to the bin” and leave the ordinary world totally? So simply put, how do you keep the passion alive with those things happening?

Gary: Because I’m very aware of how lucky I am and it’s all about perspective and being thankful and that’s it. Just recognizing that those things are minor compared to the health of your family or the fact that I have this opportunity that people are listening to me or have a business. They’re just small. These things are quite small in the scope of what’s really happening.

Patrick: You just talked about travel being one of the things people spend on early on and they shouldn’t. When do you get to a point where that becomes valuable to you or getting out to conferences and things because I know you speak at conferences and you obviously benefit from them. Is there a certain level where you should think about that?

Gary: Yeah, it’s probably very, very, very quickly. What I mean by that is if you can afford to go to a local meet-up, you do it right from the get go. I just think that people buy a $4,000 conference ticket before they’ve done anything. That’s what I meant earlier.

So if you could afford very early on to go to any events locally, people are what build businesses, it’s about the networking, it’s about your people skills, it’s about the people you know and way too many people overlook that.

Patrick: SitePoint of course is a web design, web development community, have you or did you, Gary Vaynerchuk, ever play around with design programs or like FrontPage or did you open up this software and play around before you feel comfortable spending money on it?

Gary: No.

Patrick: Never tried?

Gary: No, never tried. Always drew it and then handed to somebody to execute.

Patrick: Crush It! was your first book. What have you, I guess, learned during the process of launching book 1 that you wish you would have known beforehand?

Gary: Well, I did that already because I wrote a wine book before the…

Patrick: Oh, that’s right, I’m sorry, that’s right. I actually have both of them too.

Gary: No, no problem.

Patrick: …that’s pretty bad.

Gary: No worries. Well, you know everybody heard the 10-book deal so they call this book 1 on that deal. So I get it, don’t worry about it. The reason I did that was I wrote the wine book to learn as much as possible and I learned a lot, which is what I had to rely on, which was me and not the publisher and what was important and they helped me quite a bit to make this last book successful.

Patrick: Right. Because I know as an author too, I found that there really wasn’t much money out there marketing wise for book publishers and I found, I was pretty a small fish, and I found that with people, they had much larger audiences too and I guess they put some money behind you, but these days it really is imperative. It’s a lot like the music industry I think, right?

Gary: Well, they really didn’t. Most of the deals I made, I made it by myself because they put in the room to succeed. There was not a lot of money thrown my way. Not even close.

Patrick: Yeah, I’m not surprised. I compare it a lot to the music industry. I think that in the music industry, it’s kind …

Gary: I think you’re right. Absolutely.

Patrick: There’s a lot of front end money but then once you get the book out, it’s on the author.

Gary: No doubt.

Patrick: So you’ve given a lot of interviews. What has been the interview that you feel has helped the book the most? What publication outlet online or offline has readership/viewership has been most beneficial to you, do you think?

Gary: I think that’s a great question. I would say a couple of things stand in mind. I think the CNN piece that I did on a Saturday was very big. Scott Simon, Weekend Edition, NPR was very big, and I would say doing TWiST, This Week in Startups with Jason Calacanis was very big as well.

Patrick: So what’s one that may not be as obvious? I mean, obviously CNN is huge. Jason is well known; I like Jason a lot. What’s the interview that you did that you going in you thought, “Well I don’t know…” but then when you came out it was a big deal?

Gary: Actually I think Jason’s. I mean I know Jason’s big and all but it’s not CNN or NPR, or all the other television and newspaper I did. I think why Jason stood out was we were there for an hour and it was so honest and we were so cool and just like – it was just so real and there was a lot covered in that hour interview. I mean I did FOX Business, I did other big things – newspapers, major radio – I’ve done a lot of big things and other TV stuff that didn’t have the same impact.

Patrick: So let’s stick to book publishing because a lot of people – and it’s true the book publishing industry is an old industry and they’re making progress but they’re still not quite there yet. What are some of the things that you have seen in the book business that you think the industry needs to get on to very quickly?

Gary: Well, the book industry is broken. Anybody who’s in the middle that doesn’t provide marketing value is broken, in my opinion. So that’s it. I mean that’s where the publishers sit today. They need to learn how to market. They can’t just rely on being in the middle because they’re not needed. You can go direct to Kindle in a year or two.

Patrick: Right. I guess their value to me when I was looking for a deal was in access. The access that they have and they currently hold, and it’s a grip that they’re losing but still when you’re talking about Barnes & Noble or something like that, for the average person…
Gary: 1,000%. Their access to retail is by far the biggest thing they have.

Patrick: And do you think that’s something they’re going to be able to hold on to for a while or is that the saving grace or is that something that’s slipping away? Because like you say, we have the Kindle, we have e-books. We have an Amazon sales rank that’s publicly available, that bookstores can look at and say these books are selling well online. Let’s find a good author and get in our stores regardless of where it comes from.

Gary: It is not something I believe they can hold on to.

Patrick: But you still signed the 10-book deal and you’re someone with a huge audience who could very easily sell books to the – and basically does sell books directly to their audience anyway, deal or not. So I guess the value for you totally was in access and the up front money. Correct?

Gary: No. The big thing was the access to the retailers and the fact that the web share on the backend was 50-50 instead of the normal 10% or 15%.

Patrick: That helps.

Gary: That was attractive. That was a big reason, and because I still don’t think we’re all the way there yet. The last couple of answers I gave are much more of a reality of three to four years from now, not today. So they still have control of the retail relationships. I think in two or three years I can just hit up Barnes & Nobles and Best Buys, and places myself be it a DM or a tweet, or just a cold email. And so for now, they still hold that and that was definitely the reason.
Patrick: Yeah, I wrote a post about someone who wanted to get a deal and have an agent but they wouldn’t have any interest and the key is to just bring people to you, create the audience that makes people come to you. The music industry, again, the label execs hear your record playing in every club then they’ll come to you I think.

We have a lot of conferences in the web development, programming, social media space; South by Southwest, Blog World Expo all come to mind. You’ve spoken at tons of them, all of them. What do you think are the most beneficial two or three conferences for someone who is in this space, in this web technology development social media space?

Gary: South by Southwest for sure. The Web 2.0 Series by O’Reilly and FOWA – Future of Web Apps by Ryan Carson.

Patrick: What do those conferences offer that the others don’t? Is it strictly in the quality of the audience, the networking?

Gary: Yep. That’s it. Period. The content is never the game. It’s the people that are actually there that you can network with. Perspective.

Patrick: Yeah, perspective. Right. Since this is the January 1st, 2010 show of the podcast, I wanted to ask you this. So it’s December 31st 2010 and you look back on the year 2010, what are the some of the things that you want to say you accomplished?
Gary: What things do I want to achieve in 2010?

Patrick: Right.

Gary: Spend more time with my family. Spend a little more time putting my head down and building VaynerMedia and Corkd. Those two things really stood out for me.

Patrick: Okay great, Gary. Well I think we’ve tackled all the subjects. I appreciate you talking with us today and have a great 2010.

Gary: Dude, thank you so much for taking the time and having the interest. I appreciate it and I hope you have a great holiday.

Patrick: You too, man. Thanks. Goodbye.

Gary: Thanks, man. Bye bye.

Patrick: Again, that was Gary Vaynerchuk, who, among other things, is the author of Crush It! Why Now Is The Time To Cash In On Your Passion. The book, for the website, is

Thankyou for listening to the SitePoint Podcast. I’m Patrick O’Keefe of the iFroggy Network, (, and I’m @iFroggy on Twitter.

You can find SitePoint on Twitter @sitepointdotcom.

Have any thoughts about this interview? Please visit us at to leave a comment on this show and to subscribe to receive every show automatically. Email if you have any questions for us; we’d love to read them out on the show and give you our advice.

This episode of the SitePoint Podcast was produced by Karn Broad. Thank you for listening and have a happy, healthy, and successful 2010.

Theme music by Mike Mella.

Thanks for listening! Feel free to let us know how we’re doing, or to continue the discussion, using the comments field below.

Kevin Yank is an accomplished web developer, speaker, trainer and author of Build Your Own Database Driven Website Using PHP & MySQL and Co-Author of Simply JavaScript and Everything You Know About CSS is Wrong! Kevin loves to share his wealth of knowledge and it didn't stop at books, he's also the course instructor to 3 online courses in web development. Currently Kevin is the Director of Front End Engineering at Culture Amp.

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