#ASKGARYVEE: The Entrepreneurial Street Smarts & Business Instinct & Story & Winning & Legacy

“This is what I did when I went into my dad’s business at $3 million in revenue and made 10 percent gross profit before expenses. The liquor business is notoriously hard because there’s a wholesaler in the middle that takes 25 percent of the 50 percent that a retailer normally takes. So here’s what I did. I took the low-margin items that were driving the store’s business and bet on them. I took all the Santa Margaritas, the Kendall Jacksons, the liquor items that were low margin, and used them as the marketing to get people in the door. These low-profit margin items were the honey.” — GaryVee.

It is deliciously ironic that I, an F student, have received invitations to speak at Harvard, Yale, and Stanford.

School was never my thing. It’s an unusual thing for an immigrant to say, especially a Jewish immigrant. Traditional education was my people’s ticket out of the ghetto. But I sucked at it.

We’re not talking B’s and C’s, with the occasional D popping up it’s ugly head. We’re talking a long, remarkably consistent stream of D’s and F’s. There were just so many more interesting things to think about than the Pythagorean theorem.

“It’s a hard conversation to have because the American college dream has been so well branded. Even when kids know in their souls that they don’t belong in school, parents can’t let it go. As a forty year old man today who spends most of his time with successful entrepreneurs and professionals, I’m fascinated at how little parallel there can be between one’s level of education and success in modern business. I would never be so naive or misguided as to suggest that time spent at a top university can’t help you get closer to financial success. But I passionately, emphatically believe the American university system has lost its value in the face of the speed and intensity of the current business marketplace” — Gary Vaynerchuk

Gary Vaynerchuk’s #AskGaryVee: One Entrepreneur’s Take On Leadership, Social Media & Self-Awareness talks about the hard knocks of his hardcore business instinct, navigating the digital and social, clouds and dirt, and the New York Football Jets of New York. The book outright says don’t regurgitate Gary Vaynerchuk’s advice, instead deploy them for your own means and ends. Okay. So story time. Story and creativity. One of the great leverages in life is the skill of personality, because it can’t be commoditized. You can’t duplicate Kobe Bryant, you can’t clone a Dave Chappelle, and you can’t copy GaryVee. It’s too hard to do. Ironically, our school systems reward uniformity, making other kids more like other kids as the definition of success. But in business, in American capitalism you get rewarded for being able to do things others can’t. Things like the SATs homogenize kids, stunt creativity, and say “if you’re not doing things this way, you’re doing it wrong.” But just like that Kanye West “La La wait til’ I get my money right” it pays to pivot against the standard quo. Thus the Clouds and Dirt, says GaryVee…

I’ll put my own spin on things here, but I remember not learning jack crap in my two years of college, except learning how to make some friends in dorms (a valuable skill is small talking, seriously though) and watching sports. The New York teams got really, really good in 2010, so I’d always catch those TNT Eastern Conference Knicks, Celtics, Heat games at 4:00 pm or 5:00pm, go sit for three straight hours just watching television, then go off and dink around later that night. The Knicks got Amare Stoudemire, Carmelo Anthony, and the Jeremy Lin Linsanity all happening within like one year, in 2010 or 2011. The Jets just came off their first AFC Championship game, then reloaded with all these bad ass, controversial, over the top personalities and Hall of Fame stars the following season. LaDanian Tomlinson, Santonio Holmes, Cromartie, and Jason Taylor. Bart Scott talking about “how it was too damn hard to please” everybody, but in more colorful language. Rex Ryan Hard Knocks food rants. The Rangers simultaneously went on a run around this time, so all the jerseys Knicks, Jets, Rangers hanging in my dorms at Eastern Washington University. In classes, I’d bring my laptop and read every blog, article, Rich Cimini’s angry post game beats, magazines, and YouTubes on all things Knicks, Jets, Rangers. Those were the things I cared about at the time, and in the future helped my craft more than any professor in college.

There’s also something to be said- about coming from the bottom. If you want the best McDonald’s manager, you want the guy who started by mopping the floor, and next week on to the fries, as Kanye once said. Instead of paying 300 thousand on universities telling you how to become the manager, by testing you with multiple choice questions on how to mop the floor, stir the fries, etc. My example is growing up in inner city schools. Though I would attend a good high school in the suburbs, elementary and middle school was rough & tough. But an interesting thing happens in an inner city. You learn about the culture. Consumer culture. Things that are cool, and things that are not. People get clowned on for not wearing the cool stuff, in no uncertain terms, and the kid with the hot stuff (shoes, jackets, girls, basketball skills, haircuts, ability to talk trash in class because that’s all you did, who you hung out with, watching MTV/rap/hip hop videos… Unconsciously learning that form of visual story) are things that money can’t buy. It’s like a different language. Growing up in rough areas it is always about who has this, who has that. Stunting. Styling. You’ll never forget as a kid what it felt like to want something, not get it, then actually get it, then another kid getting something better, than wanting his “it” isn’t that what advertising agencies in Fifth Ave do? Ever flowing never stopping. The feedback you get is so intense, compared to growing in a more friendly, homogenized place: like a middle class suburb where parents can just give the kids what they want, so kids miss what it feels like to want something they can’t have. You definitely learn about culture that way. Just my two cents.

But that’s only if you’re an artist.

For those making big money with Science, Technology, Engineering, Medical — yes school probably matters a lot.

“The changes you’re seeing today in the educational landscape is nothing compared to the disruption you’re going to see over the next twenty years. When I’m trying to learn something I go to YouTube and watch a one minute video how to. Information is a commodity and the Internet has given us the platform to learn that way. I don’t need a teacher, no matter how charismatic, to tell me basic information. What matters, and where the experts can offer value, is in opinions, interpretations, and context.” — Gary Vaynerchuk.

What is Clouds and Dirt?

The following are actual advice and concepts from the book. Clouds and Dirt are the North Star of your business or craft, and the daily execution and nuts bolts and tactile movement of your business or craft. Where do most people stay? In the middle. Clouds are unwavering, commandments. They are the soul reason for existence of your brand. Bring value to the customer. Always play the long game, patience, people are your most important commodity, and never be romantic about how you make your money. Dirt is the tactical. For example, understanding video lengths on Instagram vs. Snap, the ROI of ads on Facebook, says Gary. Back in the early 2000s, Dirt was knowing to go all in, ALL IN, AAAAAAAAAAALLLLLL IN on Google AdWords, instead of investing in billboards or radio at the time.

“To be a successful entrepreneur, you have to be an optimist. A lack of time is just incentive to be more efficient with the time you do have. Insufficient capital is a game to see who can find the most creative way to get more. You don’t see obstacles — you see opportunities. Optimists accept that obstacles will be in their path, and assume they’ll figure out a way around them. Which is not to say the grind isn’t hard for optimists, too. It is. They just like it. If you don’t, maybe you’re not cut out for entrepreneurship. Or at least you don’t have the stomach to do what it takes to be a Number 1. And you know what? That’s okay. Thriving at Number 7 instead of stressing at Number 1 would be something to be proud of.” — Gary Vaynerchuk.

Why Do You Focus On Top-Line Revenue?

Start-ups typically cut hard margins and try to balloon profits. VaynerMedia focuses on top-line revenue, because in the media/agency landscape people capital is the only capital. By accruing as many customers as possible, same for Wine Library (Gary’s first business) for the first three to five years you’ll build a base of followers: from video blogging, social media, or ecommerce. Then you can ask for the bigger pay day, where the following knows who you are and is bought in, invested enough to pay for your brand. Here’s the biggest misleading thing about advertising: It’s not about converting people. It’s about those who have already bought in, and talking to them. Call it land grabbing, call it scaling, but build the following first by any means. Wine Library gave away a lot of the cheap liquor, to get people in the door, then salesmanship and store layout had people tasting, experimenting, and purchasing slightly higher end items. Never raise prices for short term gain, by sacrificing long term top-line revenue.

“I am not a morning person. Believe it or not I make a point to get six or seven hours of sleep per night, and I sleep like a brick. It takes a lot to wake me up. And I mean a lot I’m rising with a little more energy since I started working out and eating right, but there was a time when someone could have broken into my home, stabbed me in the leg with a knife, and stolen everything I own and I wouldn’t have noticed until the next morning. Thing is though, I’ve never understood why it would be an advantage to be a morning person. If you do your best work first thing in the morning, great. Some people work best at 3 am or 10 pm. There is no right time to hustle, long as you are hustling. It’s about what your doing when your awake” — Gary Vaynerchuk.

What advice would you give a high school senior in America who is trying to decide whether to go or not to go to college, and which one?

GaryVee gives way to Casey Neistat on this one, the video blogging bad ass who once washed dishes as his only career option while knocking up his baby moms. Neistat has done video campaigns for Nike and Mercedes Benz and made a movie for the New York Times. There’s only two things you should ever do in your life, says Neistat. Eat cheddar cheese and use extra lube with wife. No, it’s 1) discovering your passion and 2) actualizing it. Neistat has snow-boarded in New York City, vlogged it, then vlogged it again, and aaaaaaagain. College is a great place to discover your passion, says Neistat. I agree, it’s a great way to get laid for sure. GaryVee disagrees here, not on the getting laid part, but on college for passion finding. It’s expensive as hell. You’ll likely go into student debt that you can’t even declare bankruptcy to get out of. Besides, if you’re into studying abroad- You know if you want to learn Spanish because that could possiby… Just might help… Your… Job… Prospects… (wink), then why not just go to Mexico or Latin America and learn the culture, instead of books and professors. But tech has given more options away from college. Online courses like the Khan Academy, and Seattle’s very own Chase Jarvis’ Creative Live programs offer real-practical-tactical know how on all things photography, writing, drawing, video editing, food making, food photography, other food stuff, etc.

“The biggest decision in my life that made me successful today was in 4th grade. Mr. Mulnar’s 4th grade science class. I got an F on a science test. To make shit worse, I had to get it signed by my mom. To avoid being punished, I hid it under my bed, where it sat for two days until my conscious got the better of me and I showed it to my mother. Until that moment, though, I was in hell. I distinctly remember sitting in my small bedroom, crying, and trying to remember why I was having such an intense reaction to this test. And then it hit me. I made the decision to consciously eat the pain four times a year when report cards came, to eat the pain daily. That moment marked the first time I decided to fight what society expected of me and deliver on what made me happy.” — Gary Vaynerchuk.

Do you think giving up a secure job for a new and exciting opportunity is irresponsible when you are the sole provider for your family?

The irresponsible thing would be to not go for the new exciting thing. But you should talk to your spouse, ask whether you guys can live on just one income stream from one partner. Lots of this is just personal, what kind of things you want, how do you already spend your lives. But on practical terms, again it’s the irresponsible thing to not go for the new and exciting things in life, but if you’re the only one bringing in income for your family, then that’s probably a big no no. Entrepreneurship can come at the expense of luxuries, but never rent or food of your children. Now if you’re single, fresh out of college, and in your twenties, you might as well go for it. It’s worth the fight. As for students just graduating college, looking to get into advertising agencies, if you can’t find a job for three or four months, work for free. You might as well get skills, get connections in your industry or field, and most of all get something very useful besides money while working. It’s worth the fight.

“There are a lot of people who are able to enjoy being hobby entrepreneurs because their joy is in the process, not in the outcome. So they make maybe $10 to 40k on the side doing something they love, and they’re satisfied with that because they don’t need to make a billion dollars to be happy. If you’ve gotten to a point in your life where you can’t ditch everything to follow your dreams, being a hobbyist can give you the best of both worlds.” — GaryVee.

What Is Self-Awareness? How do you increase it?

Don’t know.

Rely on others to give critical, tough pill to swallow truth.

When I was twenty-six, no one, not me, certaintly not anyone in the wine world, was into email yet. I left around 7:30 or 8:30 pm and the store closed at 9 pm. I had time to play Monopoly on GameCube. I lived in an apartment with a girlfriend and my best friend lived above me. I lived in New Jersey, I didn’t have that New York City hustle yet.

While the vast majority of questions lobbed at my way have to do with launching start-ups, building personal brands, leveraging social media, I also get asked about hiring and firing, public speaking, the perks of family and business.

Also the Jets…

I call it as I see it.

— GaryVee.

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Mark Namkoong Life+Times

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Drawing and drafting board for the imagination.

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