I sat down with Gary at LessConf in Jacksonville, Fla., to talk about working hard and building brands.

Nancy: You are famous for cheerleading, for telling people to work an 18 hour day. How has being a dad changed your perspective on that?

Vaynerchuk: It hasn’t. I don’t necessarily need people to work 24 hours a day. I need them to not do stupid stuff when they’re unhappy. If that ends up being 12 hours a day, or seven, or four, that’s fine. Because obviously family is first. And a lot of times for a lot of people, your first job is first, because that’s what pays your mortgage. It’s just at night, instead of plopping on the couch and eating junk food and watching Baywatch re-runs, there’s a lot of opportunity to build brand.

Nancy: Although you are known for doing all that motivational speaking, recently it seems to me that your focus has shifted a little bit away from pure motivation into a little more practical advice, especially with the book. Can you talk about that shift a little bit?

Vaynerchuk: It’s always been there. It’s just that the “rah-rah” stuff is so sexy, and people focus on it. I’m not a motivational speaker as my profession, or a life coach, or a self-help dude. I build businesses. I built a $70 million wine company. AJ and I, my dad and I, our partners and family have spearheaded Vaynermedia, which is well on its way to being a million dollar company. And Gourmet Library. And I was the kid that was making a thousand dollars a weekend selling baseball cards, which if you prorate it is $52,000 a year for one day a week’s work. So, this is a knack, this is a skill. I’ve always said be patient, hustle, you know, practical advice, but it always got pushed to the side. So this is no shift…this is probably why I wrote the book. Because in a book environment, I think it comes through more for a lot of people. It doesn’t get lost as much, because there are sections just devoted to it.

Nancy: You’ve been investing in a lot of startups lately. What gets your attention or gets you excited about one? Like at my house, when we’re looking at a new tech product, it has to pass the mom test of “could our moms use it?”

Vaynerchuk: Well, I don’t think that I would invest in any startup if that had to be my barometer, because moms get involved later. Products iterate to become mom-friendly. Mine is, is this valuable? And does it invoke emotion? Those are the two things that I’d look at. Does this product make people think about something, feel something? Facebook inherently created an environment of your world, gave you a feel of speed, almost like having a fast Porsche that you never saw before. So those are the kind of things that I look at.

Nancy: So you assume that if it brings that kind of feeling, that that’s a good investment down the road, because it’ll gain some traction?

Vaynerchuk: No, that’s just some of the things I look for from a product standpoint. Then I look at who’s the entrepreneur — who’s driving the car. That’s imperative to me. And so, there’s a lot of factors. Is the product over-hyped in the mind of the entrepreneur, which means it’s not going to be as good of a deal for me? There’s a lot of practical things that I look at.

Nancy: You’re talking a lot about personal branding, finding your passion. What are the top three skills that you think people need to be able to craft that sort of branding for themselves?

Vaynerchuk: I think this is what’s important: I think everybody can win. Everybody is going to win. Not everybody is going to be Oprah, there’s going to be a lot of Donahues, and a lot of Sally Jesse Raphaels, and a lot of Geraldos, right? What I think is important is this, for people to understand: The fact that we all can now go to Yankee Stadium and tap the plate and get a swing at the bat, was not real three years ago. You couldn’t become a brand. What you were going to do — leave your kids and your husband and fly to LA and find an agent? You had no shot. So that’s what I’m screaming about. Not that necessarily everybody’s going to win on this epic level and everybody’s going to make a trillion dollars, but do not disrespect the fact that everybody has a swing at the plate. And that’s a big deal.

Nancy: Everybody knows you want to buy the Jets. Do you have any other goals?

Vaynerchuk: The only goal that I have is that, and to spend time with my family and make sure that they’re healthy. And even the Jets goal is a big one but not something I’ll let define me. I’m not going to jump off a cliff if I don’t end up buying them.

Nancy: A lot of web workers spend a lot of time on the road, just like you do. What’s the number one piece of travel advice that you’ve picked up in your time on the road?

Vaynerchuk: That’s a great question. I do a lot of interviews, so when I get a new question, they’re good. The number one piece of advice? I think there’s only two things you should do as a businessperson in this web world when you’re flying. Two: Sleep or do email…no in between. Hardcore get in the trenches with your audience and answer their questions, or get the rest you need to execute it. Don’t watch a movie. And I understand you need time to unwind, people need that. But that stuff needs to be cut out a little bit. That part, where you’re watching Seinfeld reruns on your flight. That’s those two hours that really are the difference in building a big business. Now if you’re happy, and content, then watch Seinfeld.

Are you really working towards your goals? What are you giving up?

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Do you work with family members? How does it work out for you?

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“Be there, be behind the screen,” says Strauss, meaning that you need to be present, you need to be engaged yourself, and you need to care. “Who you are is who you are, all the way down to the cells of your body.”

According to Strauss, some ways to enhance your authenticity — beyond simply being yourself — include:

1. Pay attention. “Be the consummate observer. Be the listener.”

2. Be positive. “Be as positive on the back channel intercom of the Internet as you are on the front channel intercom.” Strauss emphasized that even “private” communications can be quickly made public so, in a way, there really isn’t a back channel online.

3. Use “Thank you.” “If you can’t get to thank someone, you walk around the room until you can,” said Strauss. Even if someone says something terrible, just say “Thank you” and let those two words hang in the room. People will get your point between the lines.

4. Own your passion. Still trying to identify your passion? “What are you always, always talking about? That’s your passion,” said Strauss. “Look where your friends come to you for help. The problems you are solving is what is most dear to you.”

5. Solve problems. Said Strauss, “If you end up solving problems for people, you end up solving it yourself. If you solve a problem for yourself first, be generous about solving that problem for others, too.”

6. Make connections. Strauss explained how much she loves connecting ideas, connecting people. By caring so much about connecting to other people, she has built a real community with conversation via her blog, not just a repository for comments.

7. Start a conversation. Strauss gave a few tips on how to build community on your blog: “Don’t blog too thoroughly. Leave some white space for people to comment…When people comment on your blog, don’t just reinforce what they said. Ask them a question back.”

8. Play for keeps. Strauss asked, “Why play a game if you’re not going to play for keeps?” adding, “Don’t ‘sorta blog’ for anything because no one will know you. You’ve got to own it.” Hearing this, I felt it was a key tenet of authenticity: to realize the commitment it takes to be yourself, be real and to be committed to your community.

How are you owning — and reinforcing — your authenticity?

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A few of the characteristics of an influencer, according to Brazell, are:

1. Quality. Says Brazell, “It’s not numbers. It isn’t the number of followers you have. You can be the best marketer in the world but nobody cares if you don’t have quality.”

I agree with Brazell’s statements about quality over quantity, but if you’re working with clients or trying to convince a decision-maker  — such as your boss — about social media, they still expect numbers. I may argue with my business partner every time she is looking to find the numbers to show our clients that “it is not about the numbers,” but I know I have to understand that when the person holding the purse strings demands those numbers, we’re just between a rock and a hard place.

But for those who are chasing the big numbers like thousands of Facebook friends and Twitter followers at the expense of quality content and engagement, they are in for a very rude awakening as the marketing and advertising landscape continues to change. It isn’t how many eyeballs you get in front of, but how engaged the people behind those eyeballs are with you that matters.

2. Transparency. “With an influencer you know what they are thinking, what they are going to do, why they are doing it — because they’re transparent. You do what you say, you say what you do. Transparency builds trust,” says Brazell.

I couldn’t agree more. Whether you’re a blogger or other kind of content producer — even if you’re just commenting in someone’s else’s forum — be transparent about who you are, what you do and why you do it. People appreciate that honesty. And they resent it when you hide your identity or intentions; trust is broken. Don’t go there.

Brazell also mentioned two other qualities of influencers: they have charisma and are inspiring. He says that there is a motivational aspect to what influencers do. “Know how to talk to people. When you motivate people, you start building people up, and you give somebody something that is worthwhile.”

What do you think makes someone an “influencer?“

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For the sake of all those involved, and to avoid scaring people in my area away from specific groups or events, the identities of all those involved will be kept a secret. The specific names of people doesn’t matter so much as the setting and organization of the event, anyway.

Tweetup the First — Small + Casual = Quality

Like a debutante at her first ball, I was nervous but excited about attending my very first tweetup. Two things drew me out of my shell: The organizer was someone with whom I’d had very positive dialogues on Twitter leading up to the event, and the guest list was small and handpicked by said organizer, whose judgment I trusted. It didn’t hurt the the venue was mere blocks from my house, in a neighborhood I was familiar with.

The format was very informal, without a guest speaker, and with socializing at the top of the agenda. Drinks (primarily sangria) and conversation flowed freely, and not once did I encounter a sales pitch or aggressive self-promotion, though I did walk away with a few business cards and a strong impression of who people were and what they did. That was key for me, since the hard sell inevitably sends me screaming for the hills.

End result: I had some laughs, made some worthwhile connections, and generally had a good time. I can be shy meeting people for the first time, but the small group size (10 to 12 people) made it impossible to stay in my shell for long.

Tweetup the Second — Large + Cliquey = Nothing Worth Tweeting Home About

I was so impressed with my first tweetup experience that when another hashtagged event came up a month or so later, involving some of the people from the first and a whole lot more, I was all for attending. This one was different in a few key ways: It was an ongoing monthly event with a larger, devoted following, and the setting was bigger and flashier, lending it a definite party vibe. At first, that was what appealed to me about the event, but I think it ultimately bears most of the responsibility for my eventual disappointment.

Maybe I should’ve looked more closely at the attendees list, but what I found out too late was that most of the people attending this particular event were already deeply entrenched in their own cliques, so that they basically pared off into tightly knit clusters of four or five at the beginning of the evening and talked (as groups of friends often do) about insider things that I wasn’t privy to. A few new attendees who were in the same boat as myself managed to group together and chat amongst ourselves, but it felt a little too much like being relegated to the kids’ table at a family reunion for my tastes.

Take-aways

This by no means covers all the bases when it comes to tweetups. I’ve yet to attend the kind that takes place in a convention hall and features a guest speaker(s), for instance. But it did teach me some valuable lessons about what to expect when your Twitter usage intersects with the real world. My advice to other novices: Try out more intimate events first, even if your natural inclination is to go to bigger happenings in order to blend in more easily with the crowd. For event organizers, I’d advise you to try to avoid clique formation as best as possible. I’d rather not spend my night feeling like I’m back in high school, whether or not I bring a built-in group of friends along for the ride.

Do you attend tweetups? If so, what do you/don’t you like about them? If not, what are your reasons for staying away, and what might convince you to go?

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Here is the first of a series of short interviews with a variety of web working types, starting with venture capitalist and co-founder of Alltop, Guy Kawasaki, who reveals his favorite web app: the “ultimate marketing tool for Twitter.”

What’s Your Favorite App, Guy Kawasaki? from WebWorkerDaily on Vimeo.

You can find Guy Kawasaki on Twitter: @guykawasaki.
Stay tuned for links to upcoming video sound bites from SXSW by following us at @webworkerdaily.

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South by Southwest 2009

Here’s a guide to the SXSW 2009 Interactive panels that web workers worldwide should look out for.

Friday, March 13th

My Boss Doesn’t Get It: Championing Social Media to the Man — A major and ongoing challenge/opportunity for web workers is to prove-by-example the power of social media.

GameChangers – Improvisation for Business in the Networked World — This panel covers improving “teamwork, creativity, flexibility and problem-solving skills”: essential for every web worker!

Saturday, March 14th

Emerging From a Recession with Emerging Media Intact — While recessions cause a lot of widespread pain, they also pose great opportunities for emerging technologies, online businesses and business practices, and web-based workers.

Blog on Company Time and Get Promoted — Every web worker can learn how to better promote their company and engage relevant audiences –- whether it’s a Fortune 500 multinational or a startup of one -– and blogging is an essential part of the equation.

From Geek to Peak: Your First Year as a Freelance Geek — This session is geared toward developers making a go of it as freelance contractors, but the larger web working community can benefit from honing their freelancer skills.

Working Alone Sucks: Join the Coworking Revolution — Coworking is a hot topic in web working circles.

Sunday, March 15th

From Flickr and Beyond: Lessons in Community Management — Insight into growing, managing, and monitoring online communities. Panel members include representatives from Flickr, Current TV, YouTube, Etsy and MetaFilter.

What Do I Do With Myself, Now that the Economy Has Collapsed? — The ebb and flow of the tech economy – and specifically the current recession – brings an altered and fluid environment for web workers. Hearing from veterans who have been through past tech economy downturns and have come out the other side will surely be something that you will want to pay attention to.

Pitfalls and Opportunities: How to Fund a Startup — The current economy has made funding new ideas more difficult — at least in the traditional ways. Web workers and entrepreneurs looking to create the Next Big Thing will want to check out this panel for hints, tips and advice.

Monday, March 16th

The Invisible Web and Ubiquitous Computing — The cost of running a technology-based business keeps falling while the availability and speed of networked services keeps growing. All good things that affect the daily lives of web workers!

Beyond Aggregation: Finding the Web’s Best Content — Successful web workers access and analyze a torrent of content everyday and redistribute and repackage the most relevant bits. Finding out the latest in what’s going on with RSS and content aggregation should be a popular session, with representatives from ReadWriteWeb, louisgray.com, Techmeme, AideRSS, and Lijit in attendance.

Outsourcing 2.0: Is the World Flat or Not? — Web working increasingly means leveraging outsourced resources, so finding out the latest trends from industry experts from the likes of Monsoon Company, Startech Global and Flatsourcing.com will be very useful.

Ultimate Showdown of Content Management System Destiny — The choice of which CMS to use is a tricky one.This panel features a fun showdown, an “Iron Chef style competition” in which developers from various open-source content management systems will all build the same web site.

Browser Wars III: The Platform Wins — The web browser is where the web worker lives and breathes, so hearing from representatives of Mozilla, Microsoft, and Opera should be very exciting indeed. No Google though!

What panels and presentations are you most looking forward to from SXSW Interactive this year?

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This the third time in about three years I’ve asked, and the response each time has been rapid and vociferous, generating at least eight to 10 times more responses than I usually get to a column.

And what do the people – or at least my people – say? They are horrified at the very mention of the idea, with some vowing to stop flying or get into physical confrontations at 30,000 feet if they are subjected to the ill-mannered around them chattering away on the phone in a cramped airline cabin. Out of 58 e-mails and phone calls so far, 56 said they’re vigorously opposed.

Here’s a typical response, this one from a business owner in Chester, Pa:

I can think of nothing that would make travel more unbearable than cell phone use on airplanes. People are loud, rude and inconsiderate in the terminal. It would be even worse on a plane.

If you feel the same way, don’t worry. The prohibition about voice calls is not about to change. But the ability to access the Internet for e-mail and texting in flight is changing, and we want to know what web workers who have to fly on business think about all of it.

First, I need to say more about the whole issue of why you can’t make a cell phone call in flight, and my theory of why my other audience – the readers of a weekly newspaper column that appears in both print and online – has such strong negative attitudes about the subject.

Cell calls in flight (other than on those very expensive seatback phones still available on some carriers) are outlawed because of Federal Aviation Administration uncertainty about their effect on aircraft navigation and communication equipment. The Federal Communications Commission has had concerns whether cell phone service at ground level could be disrupted by in-flight service.

But that hasn’t been the deal-killer each time the FAA or FCC has opened the subject to study and comment.

Flight attendants, joined by thousands of people like my newspaper readers, have pleaded for the prohibition to stay in place out of fear that the annoyance factor would lead to greater “air-rage” incidents.

For the first time, that term could be applied to more sober people than drunks.

Congress has even gotten into the act, after the European Union last spring said airlines that want to allow Internet access could also allow voice calls. A bill prohibiting the practice passed the House on a voice vote but hasn’t been taken up the Senate.

The opinions of my newspaper readers on this topic are not a scientific sampling, of course, in the same way that few “surveys” on the web are, since those who answer are self-selected. My readers also are older and almost certainly less tech-savvy than readers of this blog. Some were also probably influenced by my own opposition to any change.

But many of the newspaper readers also are business people, and only one of them told me he doesn’t own a cell phone. So they probably aren’t unlike those who have told regulators they want to keep the in-flight ban.

The good news about this for those who would like to work on the web on an airplane is that access for e-mail, texting and web browsing is coming soon or is already here.

American Airlines installed a system on some of its long-haul domestic jets in August. Alaska, Continental, Delta, JetBlue, Southwest and Virgin America are among the U.S. carriers that have said they plan to offer something similar. Expect to pay $10 to $13 per flight for access. And to answer one obvious question, no, your VoIP service won’t work either.

Time now to open the floodgates and ask what web workers think.

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I’ll be wearing two hats there (hopefully neither of them a lampshade, but there will be an open bar, so we’ll see…). One is my entrepreneur hat; of course I’m hoping somebody who hasn’t lost all his or her wealth in the crash will dig my elevator pitch to the tune of several million Euros. But aren’t we all? I’m sure there will be lots of talk about the Wall Street fiasco and what it means for the tech industry and entrepreneurs looking for funding. Should be interesting.

The other hat is my web worker hat.

I’m very curious to talk to the other entrepreneurs who will be there. I have a hunch that a high proportion of startup founders are web workers. We live outside of the box. We march to the beat of our own drums. And similar metaphors. Right?

We tend to be early adopters and know more about new trends and technologies than the average Joe. Because of that, I imagine we get some really good ideas. Just about all the web workers I know put their energy and skills and creative minds into side projects, whether for fun or profit. Do you? I’ll be testing my hypothesis at the Meetup and hopefully meeting some local web workers.

The other thing I’m curious about is what Mike Gunderloy asked a couple of weeks ago in his post Where are the exciting startups? He said he hadn’t seen anything come out of recent startup conferences that struck him as particularly innovative or useful for web workers. I haven’t either. I’ll be looking to see if there are any at this soirée that might get Mike and the rest of us web workers excited. Rumor has it that innovation in the Old World is on the rise.

Lastly, if you are planning to be at the Paris Meetup, please let me know in the comments! And if you don’t make it to this one, maybe I’ll catch you next time!

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