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by Gary Vaynerchuk


  * * *

  I made a big effort to be the anti-snob of the wine world and my mom raised me right so it’s natural for me to be polite. I guess my way of politely saying your stuff is crap would be to suggest that if you like this (swill) you might consider trying this other wine (that is not swill). Sometimes people don’t know what’s good because they haven’t been exposed to anything better.

  Actually, I like trying the occasional glass of bad wine because it makes me appreciate the good stuff so much more. And the same could be said for times when I’m asked to judge someone’s content or social media presence on #AskGaryVee. Often it’s crap, and yet it’s my job to point out how it could be better without tearing an entrepreneur or marketer down so viciously, he or she never wants to try again. And seeing the crap makes me appreciate it that much more when I see others executing their social media strategy and content well. Because producing quality, whether wine or webinars, takes major commitment and effort. And I respect that.

  * * *

  Is the high-end wine business a complete hoax?

  * * *

  Wine is as much of a hoax as art, high-end restaurants, stock prices, or movie stars. Are movie stars really worth all those millions? Well, does everyone have their talent? Probably not. And when they draw audiences to the movie theater, they’re supporting an entire creative industry that puts thousands of people to work. Am I worth the money I get paid to do speaking engagements? I used to wonder, but now I know the answer is yes, because my time and expertise is valuable. If people didn’t get anything out of my talks no one would be willing to pay my fee. But people do because from their perspective, I’m worth it. The same goes for wine. I wouldn’t expect someone who is satisfied with a $10 bottle of Cupcake to believe a Château Latour is worth the $800 or even the thousands of dollars it goes for in the right vintage. But for someone who appreciates what goes into the creation of a spectacular vintage, or even the story behind it, and will savor it, that money might be well spent.

  The reality is that so long as you haven’t experienced the difference between something high end and low end, it’s hard to see what the big deal is. But in most cases, all it takes is one ride in first class, or one game in the front row of a stadium, or one sip of a Châteauneuf-du-Pape, and you’ll wonder how you ever doubted its value.

  * * *

  What’s your favorite city in the world to drink wine?

  * * *

  Wherever my friends and family are. I’d be just as happy drinking wine in Newark as in an Austin hotel lobby, or the parking lot outside a Jets game, or inside a cave in a Tuscan winery. My happiness is always about the who, not the where.

  * * *

  How do you tell the difference between all the wines in the store?

  * * *

  Buying wine based on a label crushes my soul, as does buying based on the shelf talkers (although Wine Library puts them up because they sell wine). The best way to buy wine is to form a relationship with your local wine seller and help them get to know your palate. If you can’t do that, try a different varietal every time and see what you like best. When you haven’t tried something you can’t judge it. Once you have, you form an opinion and you can start making better decisions.

  CHAPTER 22

  THE PERSONAL, THE RANDOM, AND THE WEIRD

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  IN THIS CHAPTER I TALK ABOUT MY SPIRIT ANIMAL, MY FAVORITE ROOT BEERS, MY BIGGEST FEAR, AND WHO SHOULD PLAY ME IN MY BIOPIC.

  * * *

  The #AskGaryVee Show is supposed to offer a 360-degree perspective of how I work, live, and think. I already live my life out in the open, so I’m often a bit surprised that there are still things people don’t know about me and are curious enough to ask about. But there are quite a few, as it turns out. Which is good and makes sense because of course there are many topics you should be paying attention to. And amid all the conventional questions about running companies, investing, branding, marketing, and general business development, there are occasionally some, um, unusual inquiries. We like to respect every type of question, which is how some of these oddballs made it onto the show. I’m also flattered that some people want my opinion on these random topics. I always find it interesting to hear what’s on people’s minds. I hope you enjoy reading this fun collection as much as we enjoyed putting it together.

  * * *

  Legend has it that on your first date with your wife you told her you would marry her. We want to know the details. And also, what dating advice do you have for women in their twenties?

  * * *

  Lizzie and I are married because the Jets won on the Sunday night we were supposed to go out for the first time. If they had lost, I would have canceled. But they didn’t, and so I drove into New York City for what turned out to be a three-hour date at an awesome spot in Washington Square Park. She lived on the Upper East Side, and I lived in New Jersey. After dinner I dropped her off, and two minutes afterward I called her on her cell. She wasn’t even in her apartment yet. And I said, “Can you believe this is it?” We talked during my forty-five-minute ride home, and then until about four in the morning. We were married within the year of our first date.

  And now we have a daughter, and it has completely changed me. I meet so many strong, smart women through my work, and it blows my mind that one day my daughter will be one of them. What dating advice would I give a young woman coming up in the world? The same advice I’d give a man: Think about your legacy. Live on the offense. Don’t be afraid to show your feelings and go for what you want, whether it’s a job or a relationship. It’s possible you’ll get rejected, but it’s more likely you won’t. Better to experience the brief, temporary pain of rejection than to live forever with sad regret for all the things you were too scared to do.

  * * *

  Does it bother your wife that you constantly spin your ring on the show?

  * * *

  All my straitlaced friends who don’t travel are on their third rings. Me, I don’t lose anything. I’m dramatically less careless than you might think. I can be chaos and practical at the same time. Lizzie is way too big picture to worry about silly things like that. I don’t think she minds me spinning it on the show.

  * * *

  How do I get the cute old lady who keeps accidentally calling my house to stop? I just want to nap . . .

  * * *

  You called her “cute,” which means at some level you like getting these calls. Flip the script and go on the offense. The next time she calls, try to engage in a twenty-five-minute conversation with her and form a relationship with her. Bringing her deep into your heart may bring value to your soul. Who knows, it may lead to something meaningful for both of you. Relationships are everything. And I think everyone reading this can tell that I featured this question because I almost always believe that things you do in life can be applied to business and vice versa.

  * * *

  Why is your phone always in the shot?

  * * *

  Because my phone is an extension of me, just like it’s probably an extension of just about every human being who owns one. Few people are more than an arm’s length away from their phone, even when they’re showering and sleeping. Eventually we will embed our phones into our bodies. Yes, we will be like robots. I have it near me because I need it to be a human. Think about that statement!

  * * *

  Cake or Pie?

  * * *

  I don’t eat them much anymore, but I am obsessed with blueberry and apple pie.

  * * *

  Center or edge?

  * * *

  Edge.

  * * *

  What is your favorite pair of sneakers of all time?

  * * *

  Hands down the 1985 Patrick Ewing Adidas. I’m a huge Knicks fan. The ones I hated the most? Every single pair of Air Jordans. I hate Michael Jordan. Every one of us should!

  * * *

  What is your favorite holiday tradition?

  * * *


  Going to my parents’ house in Hunterdon County, New Jersey, for Thanksgiving. Birthdays used to be sacred in our family, but then my dad screwed that up a few years ago by taking my mom to Italy and now we don’t share all of them together (yes, that’s a fun zing at my dad). So now we make sure the whole family get together at Mom’s on Thanksgiving. We’ve all got to be there for the football games. AJ and I are usually doing something crazy, my sister’s kids are there, extended family . . . it’s the best.

  * * *

  My husband is a “big-picture” kind of guy, but so is his wish list. Any advice on Christmas shopping for this type?

  * * *

  Make something that is one-of-a-kind, something that is not scalable. I know exactly what I want: one-of-a-kind experiences. Here’s the greatest gift Lizzie could ever get me: She could interview every person I ever met, or come to VaynerMedia and record everyone telling me I’m the greatest. It’s easy to spend money; people will appreciate the time, effort, heart, and soul you put into a gift far more.

  * * *

  If you could clone yourself, would you?

  * * *

  Easy as they come. I would, 100 percent. I wish this tech existed because I would send the cloned version to spend every waking moment with my family. No, wait, I meant at work? Uh-oh, is that Freudian? Maybe I do love my business more than my family? Not possible. I’d love to take the equal version of me and accomplish the two things I love most at the one time. Man, I hope I see this technology before I go.

  * * *

  Do you wish you had done more or focused more on just one thing when you were in your mid-twenties?

  * * *

  I did focus on just one thing, and it was Wine Library. I wish I’d gone out and had more fun, hooked up with some girls. It’s actually unfortunate how focused I was on the hustle and building my career when I was still so young. I’m pumped about my life and I’m happy, and I would never change a single thing, but it’s human to look back and see in retrospect how you could have done things differently. But I made choices that served me well. I learned the skills, discipline, and focus that allow me to run a company while juggling a whole lot of other fantastic things at the same time.

  * * *

  What’s the hardest thing you’ve had to deal with in the past five years and how did you get through it?

  * * *

  Hands down, it was leaving the routine and day-to-day operations of working in the family business and easing off WLTV and Daily Grape. I just didn’t realize what an emotional experience it would be to transition into a new chapter of my life that also profoundly changed the dynamics between my father and me. I got through it the way I get through everything: I kept communicating with everyone involved or affected.

  * * *

  Are you ever scared before you do something big, even something not business related?

  * * *

  The only thing I’m really scared of is reading in public. I am an atrocious reader. It’s even affected how I run my business. In 2015 I started creating only 5–7-minute meetings with much of my staff because I don’t read fast enough and therefore wasn’t reading their emails in full ahead of time.

  Even reading to my daughter, Misha, is hard. If I were asked to concoct a fabulous story off the top of my head, I’d be good with that. But Goodnight Moon? Oh, God. And the Haggadah at Passover? I’m a nervous wreck.

  One of the reasons I didn’t accept the offers to do TV shows is I didn’t want to have to read off the teleprompter. And even when I did my wine Web radio show on Sirius for nine months, my first commercial read was a disaster. It was probably the worst thing I ever did publicly. Then Sam Benrubi saved me by coming into the booth and saying, “Do what Howard Stern does. He can’t read, either. Just read it to yourself and do your thing.” So I read it through once to myself, figured out what Stella Artois (now a VaynerMedia client) needed to be delivered with that ad, and then I did an incredible read. Truly, the second reading was insane.

  I’m scared of snakes, a little of heights, and ultimately of dying. But reading in public? Please don’t ever make me do it.

  * * *

  What’s your spirit animal?

  * * *

  I originally answered that it was Ram Man from He-Man. But now that I think about it, you know who it really is? My wife, Lizzie. She’s the best.

  * * *

  Are you the person behind the #TomShady billboard?

  * * *

  I wish I could take credit. It wasn’t me.

  * * *

  If you could have a bionic body part, which body part would it be and what powers would it have?

  * * *

  I was cohosting the show with Casey Neistat when this question came in, and I’ll bet Casey’s answer came as a surprise to a lot of viewers:

  “I do have one. My right leg from the knee to the hip is made of titanium. I was twenty-six years old, lying in the hospital with my leg broken in twenty-seven places, when the doctor said, ‘You’ll never run again. You can catch up with a taxicab, but that’s it.’ Prior to getting my bionic limb I wasn’t much of an athlete or a runner, but since getting my metal leg I’ve run twenty-two marathons, four Ironman Triathlons, and countless other races.”

  As for me, I would go with ears. I’m not joking. One of the things I enjoy and think I do well is pay attention to more than one conversation. I’m often at a dinner table or at a conference, and I’ll be fully immersed in a conversation but still able to listen to two or three other side conversations. Often when I talk to a group of forty or fifty I’ll hear someone whispering to a friend or colleague and then incorporate what they said into my talk while looking at the person. It usually freaks them out. I don’t think people listen enough.

  * * *

  What’s your favorite airport? LGA? JFK? SFO?

  * * *

  Small ones, like in Des Moines; Greenville, South Carolina; Montana; Arkansas; Chattanooga, Tennessee; the Vermont airport . . . the ones where you can roll up and be at your gate in four minutes without precheck. I know the big ones—LGA, LAX, JFK, SFO/L, Newark—better than I know my own office. They’ve become my home. The people there are my friends. The coziness that I feel at an airport is disturbing. Super-disturbing!

  * * *

  Would you ever automate your position, delegate to as many people as it takes, and fully engage in your family and life?

  * * *

  Absolutely not. Of course I love being with my family, but I would suffocate if I couldn’t work to create the things I want to create. I want to build companies and commerce and be a salesman and put out content. I love the process, the grind and the climb. I love what it’s going to take to get to the point that I can buy the Jets more than I’m going to love actually buying them. Most young entrepreneurs want stuff—the watches, the cars, the planes, and the bling. I just want the pain, the gratitude, and the happiness that come with the work.

  * * *

  Do you work on your birthday?

  * * *

  I hate my birthday because I hate getting older with a passion. I’ve worked on every birthday of my entire life, including when I was a teenager and my dad would drag my ass to the store on the weekends. I’ve given speeches on my birthday. I’ve attended conferences on my birthday. I’m 100 percent all in every day of the year. You want to do what you love on your birthday, and I do.

  * * *

  What food(s) have you added to your new lifestyle that you are enjoying the most?

  * * *

  There are no new foods. My trainer Mike and I went to the supermarket and I told him what I liked that was conceivably healthy, like mangoes and shellfish. Luckily for me I like pretty much everything, so this new regimen has not included any additions. It’s been all about subtractions.

  * * *

  Why don’t you watch your own videos? Ego or time?

  * * *

  Time. I know what I did.

  * * *

  W
hat value do you find in knowing a foreign language?

  * * *

  My Russian is English-accented. I failed German twice and the only reason I graduated from high school is that my Spanish teacher, Señora Kennedy, was the greatest of all time. You need to pass two years of language in New Jersey, and since I had already failed out of German, I needed a miracle to pass Spanish 1 and 2. God was good to me and gave me a teacher who had a hard reputation but clearly was smart as shit because she could see who I was. She called my mom and said, “I’m giving him a ‘C’ for charisma, but he doesn’t even know how to say hello.” She knew I had “it.” Big shout-out to Señora Kennedy!

 

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