Gary Vaynerchuk is director of operations at Wine Library, a wine retailer, and is perhaps more widely known in internet marketing circles for his videos, where he primarily delivers insights into topics related to social media.

He is also the face behind Wine Library TV, the video-based wine tasting blog that has done much to help transform the Wine Library business into a $50m-a-year retailer, from $4m six years ago.

Gary is a blast…

You’ve done an amazing job with Wine Library TV, I think largely because of your passion for the subject, and your ability to get involved in the community. What are the basics of creating compelling content?

Fundamentally it is important to talk about what you know best. People talk about my theme of building around passion, my first passion is the New York Jets but there is a passion that I know a lot more about and that is wine and marketing and that is why I have Wine Library TV and

What has this done for your brand, and your bottom line?

It’s given me a huge opportunity with my brand obviously, opened a lot of opportunities like being represented by CAA to being in a situation where I wrote a book on a six-figure deal, to national TV appearances.

For my bottom line, it has created opportunities in the way of speaking fees, and driven traffic to the Wine Library retail side. But it has also give me the foundation to launch something like, and instantly get enormous amounts of media attention based on my personal brand equity.

Participating in the community is a great way of putting your brand on the radar. What are the key takeaways for marketers?

You have to give a crap. Just marketing for the sake of marketing is shallow and has no long term appeal. It’s like being on the front page of Digg… the traffic is great, but at the end of the day what do you keep? You need to put in the blood, sweat, and tears: it’s time for people to go Rocky Balboa on their community!

Should an organisation have a ‘public face’, or should all employees be encouraged to get involved?

I think that comes down to the company’s preference; it needs to be comfortable for people on the top. I’m very comfortable having multiple faces, with many of us in the company using Twitter to interact with people. Heck, I’ve made Mott a bigger celebrity than me!

It comes down to the DNA of the CEO and of the company, both tactics can work. Zappos is going with the full-on approach, others want to be like Steve Jobs.

Who should be in charge of this sort of participation? Do any rules of engagement need to be established?

It’s really like the person who is wearing the underwear… who is controlling the game? That person needs to establish the rules for how you approach it and ultimately rules are hard to control in social media. You are better off letting the world run wild. You cannot completely control your message any more. Be as authentic and awesome as possible or you will fall like the Berlin Wall.

How important is brand / reputation monitoring? And how much more important is how and when you choose to respond (assuming you’re listening)?

It’s the whole game. If you aren’t monitoring your brand you are dead. I ‘ego search’ all the time, which I think is a bad term. I’m not doing it to feel good about myself, I already feel good. I monitor it to see if there are problems or concerns.

The way you handle these situations is huge and ultimately will define you. The blueprint is always bullshit; you can have a game plan going into Sunday but if the opposing offense suddenly lines up in a wildcat formation you are in trouble! The way you respond to criticism is huge in the marketplace and I hope you look yourself in the mirror before pointing fingers.

What are the main tools of your trade these days? What should be in the online marketer’s arsenal?

Twitter. Ustream. Blogs. Facebook. And a pulse! Seriously, reading Techcrunch is very important or Mashable, they normally break news on new products. You need to have a video platform, whether it is Viddler, Vimeo, Blip, YouTube… then TubeMogul becomes important to distribute your video in multiple places.

Seesmic is a site that has potential and could become important. Google Blog Search. Twitter Search to find out what’s being said on Twitter. WordPress, Livejournal… there are tons of tools. The important thing is how you utilize them.

You’re very big on return on investment. Internet marketing channels are far more measureable than TV, so why is it that TV still attracts the big budgets?

People suck. Fundamentally there’s still a lot of classic old school decision making people in marketing. And really there is no reason not to be on TV if you can afford it. But some 58 year-old Tommy Stevenson at a marketing executive company has no idea what Twitter is.

That said, a lot of search activity is driven by TV and press campaigns. Brand advertising still plays a role, even if it is hard to determine influence. Maybe it’s about value for money, as much as anything?

Wrong. I’ve been on TV, and don’t think I wasn’t watching those stats.
But there is no comparison to getting love from a major internet site like Digg, Stumbleupon, or Techcrunch. All of them drive more traffic than anything I’ve done on TV.

Have you seen any cool multichannel campaigns lately? What makes a good one?

I really haven’t because I haven’t been paying attention; I have been so overwhelmed with my own community, and I never consume that much media. At the end of the day there’s lost of ways to cross pollinate marketing and plenty of people doing it the right way, but far too many people don’t have a good balance.

The fact that Rick Sanchez from CNN is one of the most followed people on Twitter is an absolute joke. I mean, it’s a great job by him, but his brand shouldn’t be that strong. If Tiger Woods started using Twitter, heck, even if Phil Mickelson did they would be first by far.

Mobile seems to be finally catching up with all that hype. How excited are you about the opportunities in mobile, and what are you doing about it?

Very excited and I’m dancing, absolutely dancing. I’m paying close attention to Brightkite and Qik and other platforms, though I have not been using them heavily yet.

How important is it to be agile / flexible, in terms of business / marketing / development?

Very! Are you kidding me? It’s the whole game. People make plans and they get ruined. Everybody that made plans to sell high-end shit this holiday season got screwed because of the market. You have to readjust.

How the hell do you stay focused?

Because I want to buy a football team that’s going to cost 3 billion dollars and I want it for real… by the way, my focus is my chaos so it is kind of natural, it’s just how I’m built.