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I suspect the topic I will most want to talk about when I get to the end of my career will be leadership. It’s a skill that came naturally to me at a young age. Yet as proud as I am of my leadership skills and effectiveness, I still work on it every day, and it’s an aspect of myself where I feel I am continuously growing. This chapter allows me to thank my employees, whose smarts, talent, and hard work always push me to raise the bar and hone my abilities. They have afforded me the chance to take my leadership skills to a much higher level than I ever realized was possible.

My philosophy on leadership is very simple: Everything in business stems from the top, whether you’re the boss of two people in a three-person team or the head of a Fortune 500 company. And everything that happens in a company is 100 percent the CEO’s fault. After all, the CEO is the person who puts people into a position to make good or bad decisions. It’s no accident that when some companies change their CEO they go from winners to losers or vice versa. It may be the most important variable for success in running a business.

Being a leader today is a greater challenge than ever because of social media. It has completely changed the nature of the job. You used to be able to—no, leaders were expected to talk from the top of a mountain. You’d make your proclamation and not worry much about hearing anything back, certainly not in real time. But now that our communication channels have given everyone a voice, whatever you say from on high may invite a reaction. You might get it in-house, or you might get it from the masses. That’s proving to be a challenging adjustment for some leaders, especially those further along in their career.

The only effective way to truly lead is to practice and model the behavior you want to see in others. That’s why I once drove across state lines in a blizzard during the height of the Christmas rush to deliver a single case of white zinfandel to a customer whose order had been delayed. I know my team is watching me. I can’t tell them to go the extra mile if I’m not willing to do it myself. If the DNA of any business stems from the top, the top has to ensure that its values, beliefs, and attitudes trickle down to shape the culture and encourage a productive, innovative, creative, and even happy environment.

One hallmark of a good leader is to ask questions. It’s the best way to show your team you recognize they’re more than just cogs on a wheel. “Hey, how are things going?” “How’s the new baby?” “What are you excited about lately?” “Do you have any ideas you’d like to discuss?” It’s also the best way to solve problems. Don’t ever start offering solutions before asking tons of questions: “Why are we two weeks behind?” “What do you think is the issue?” “What do you need?” And then for God’s sake, listen. Be compassionate. Be fair. Hire people who embody those characteristics, too. Celebrate successes, and when you have to reprimand, hark back to all the times you screwed up and remember that those mistakes have everything to do with who you are today. Great leaders aren’t born; they’re made.

I think this chapter offers a lot of value. After reading it, look in the mirror and think about what you do well and how you could do even better. Leadership needs to be a big pillar in your development if you have ambitions of building a business. The answers you see here may be the secret sauce to any success I’ve enjoyed in my career.

imageWhat are the most important lessons your father taught you about building a business?

My dad is responsible for the single most important advice I’ve ever received:

Your word is bond.

I wasn’t old enough to drink when I started working the floor at my dad’s liquor store in Springfield, New Jersey, but that didn’t stop me from being a great wine salesman. Not only had I memorized everything I had read in Wine Spectator, but I was naturally charismatic. Now, before I started at the store, I was also a bit of a bullsh@t artist. I would say absolutely anything to sell a baseball card. Maybe that’s no surprise; a very, very fine line separates salesmanship and bullsh@t. My dad, however, made sure everyone working in his store knew the consequences would be severe for anyone who tried to cross it.

He taught me that when you make a commitment, you stick to it. If I bought fifty cases of wine, I was in for those cases no matter what. If the market changed or the wine received a poor rating, I was to stick with that purchase. You take it, you eat it, you drink it.

Those lessons made me into the man I am today. They showed me that I could use my charisma for good, and that I didn’t need to cut corners or treat people poorly to succeed. For this reason, I’ve been able to hold on to business relationships for decades. Being honorable always pays off in the long run, even if it occasionally makes you a little less money in the short term. The marathon truly has greater value than the sprint.

imageHow do you change a firmly established culture into one that genuinely cares about the customer?

Everything that happens at VaynerMedia is my fault. Because I empower everybody I work with to create the culture at my company, the responsibility to build that culture is entirely on me. If I fail, we fail, so I work my butt off to make sure I don’t.

Unfortunately, not everyone sees it that way. Some leaders at the head of a floundering ship might try to make excuses. They’ll say there’s some facet of the business that makes the current culture necessary. That’s bull. Who is in charge of that facet of the business? The leadership. No matter how you slice it, a company’s culture is completely dependent on the people in charge of it.

So there is only one way to change the culture when it’s broken—kill the leadership.

Have you ever seen a recently pruned rosebush? It looks stunted, bare, and shrubby, like you’ve killed the plant. Until you come back six weeks later. See, rosebushes thrive best when old growth and dead branches are cut way back. It looks awful at first, but you’d be amazed at how rapidly those new branches and buds start to grow. Within just a few weeks of pruning a rosebush can be exploding with flowers.

Now, you can’t just hack at the thing; you have to do it right. There’s a certain angle at which you cut to make sure the flowers grow in the right direction, and all sorts of other precautions someone who cares about roses a lot more than I do would know. My point is, sometimes you have to get rid of the old, tired stuff at the top to give something better a chance to bloom. And the same can be said for old, tired ideas or old, tired ways of doing business.

Obviously I’m not proposing murder, so how could you go about “killing” a company’s leadership to give a new culture room to grow? You might try to express your concerns directly to the people in charge and pray they’re open-minded enough to listen. You could try talking to influential people within the company who aren’t part of the leadership team and hoping they’ll take up the cause. You could do as much as you can within your small sphere, then work hard so that you rise up within the company and your sphere becomes bigger and your influence more broadly felt.

What if you’re working for a family business or a new CEO, and there’s no hope for change? Get the hell out. Sorry, there really is no other solution.

imageWho are your idols or the people who inspire you? Did you ever have a mentor?

I’ve never worshipped any so-called business idols, but two people that I always admired were Walt Disney and Vince McMahon, the wrestler and CEO of WWE (World Wrestling Entertainment), because they’re great storytellers who turned their storytelling into businesses. But Disney died before I was born and I’ve never met McMahon, so you can’t really consider them mentors. There are really only two people in my life I truly idolize and could consider mentors: Tamara Vaynerchuk, who taught me people skills and much about what matters in life, and Sasha Vaynerchuk, who gave me a work ethic and taught me honor and perseverance.

imageAs a business leader, what’s the one thing that keeps you up at night?

The one thing I most worry about every day is my health and the health of my family. So long as everyone I love is healthy, I will not be afraid of anything—not the landscape, not possible market shifts, not competition, and certainly not internal issues. See, some people may reject the idea that a company is a direct reflection of its leaders, but this is why I embrace it. I don’t have to worry, because everything that has to do with my business—how we navigate that landscape, how we react to fluctuating markets, how we spar with competitors, and how I handle those internal issues—is entirely within my control.

I hope you hear that. A leader is supposed to be in control. If you’re staying up at night sweating, do something about it.

imageDo you ever complain?

This question came in just as my son, Xander, was going through a whiny stage. He was only a toddler so there was nothing unusual about that, but when he’s older and I’m looking at him fondly wishing I could turn back time, it won’t be to that particular phase, because if there’s one thing I’m fundamentally against, it’s complaining.

What’s the value in it? I was lucky to learn this lesson very early on from my mother, who I swear has never complained a day in her life, and she’s an immigrant who lost her mother at the age of five and fled from a communist country, so you know her life has not always been sunshine and rainbows. Not that anyone’s ever is. But that’s my point. Problems happen. Life isn’t fair or perfect. Complaining fixes nothing. Only taking action does.

Besides, I’m the boss. If anyone has the power to fix a problem it’s me, because I’m the one with all the control. So here’s what I do: assess the problem, find the solution, and get on the offense. And I do my best to empower my employees to follow the same process.

I think some of them find it intimidating at first. Do I really mean it when I tell them they don’t need to come to me for permission to try this idea or solve that problem, but should just use their best judgment? The first time they stop worrying that they’re too junior or going to step on someone else’s toes, and just get in there and solve their problem, is a game changer. They’re never the same.

When this happens, you, as a leader, can scale that success. Get people to break through and help you solve problems and build things and spread your religion, and things start to click really fast.

Positivity is a state of mind. Honey works way better than vinegar. It will be a few more years before Xander fully understands why these things are true, but I know that as I pass on what my mother taught me I’m giving him one of the keys to a bright, prosperous future.

imageIn what situations are you most comfortable?

I thrive in the midst of chaos. I’m great to have around when things go wrong because I tend to stay cool and calm. Which is funny because I hate calm. Even New York is too slow for me at times. As soon as I walk into VaynerMedia I’ll ask someone to turn on some music, because I get pumped when there’s a buzz and a beat in the air. The ridiculous volume of things that get thrown at me every day and all the demands put on my attention would overwhelm some people, but I love it. It’s my drug. I need the action.

imageIf you could teach everyone in the world one thing you’ve learned, what would it be?

My dad taught me that word is bond, but as crucial as that lesson is, I think it’s a lesson that was uniquely important to me because of my personality.

Here’s the one universal rule I would try to teach everyone: Depth matters more than width.

That is, the smallest meaningful, intentional act will mean much more than a huge one that lacks intent or substance.

Believe it or not, I’m paying attention to many of you who are reading this book. I’m no longer able to engage the way I used to with every single person who says hello, but I’m definitely trying every single day. When I’m not in a meeting or writing or taking care of business, I’m hustling for depth with my community. I’m favoriting posts, leaving notes, replying, and saying hello, especially on Instagram (@garyvee). I try to catch your little moments and let you know that I noticed, even if it took me awhile to get around to telling you. It’s amazing how much a tweet can still mean to people.

Sadly, a lot of the social media world is still going wide—gunning for more likes, shares, and right hooks, doing whatever they can to make their fan or follower numbers grow instead of paying attention to the quality of their engagement. We want the attention, but then we don’t want to give it back. And no, offering a like in exchange for a like, or a share for a share, doesn’t count. It’s a crap move that takes no thought and has no substance.

This is my call to action: Go deep. Reach out, provide value, and be there.

imageHow do you stay constantly motivated?

One, I love what I do. I love the HR nightmares of a 500-plus organization, the headaches, the grind, the calls with an upset customer, all of it. It’s easy to stay motivated when you know your day is filled with things that are getting you closer to your goals.

Two, I’m grateful every single day. I feel so lucky to have been born in the mid-1970s, during such a special moment in Soviet history, instead of the mid-nineteenth century or the 1940s, and to have been given the opportunity to come to this country. I’m grateful for my parents, my wife, and my kids. I made this bed; how can I complain? Gratitude is amazing fuel.

imageHow do you keep others motivated?

This question came from the epic Tommy Lasorda in episode 109, an all-time great baseball manager and motivator himself. I thought it was an interesting question since he’s clearly figured out methods that work for him and his teams.

Motivating employees should be one of a leader’s top priorities. You already know I believe in leading by example, not just when you’re running meetings, but in your daily interactions, in the emails you send, even your posture. I hope that the way I carry myself and live my life motivates people to work hard and do their best by others.

But it’s not enough just to do your thing and hope everyone else absorbs the energy you put out. You also have to pay attention. Everyone has different needs objectives, and the incentives that work for one type of person might not work for another. Some people live for their kids, some people are totally career driven, some people need to be constantly challenged or they get bored. I meet with every single new hire at my company within the first few months after they start, and throughout their time at VaynerMedia I try to get to know them as best I can. I ask them questions about what they want to do with their lives, and then listen hard and figure out what makes them tick, and put them in a position where they find that if they work hard and fast, they can succeed. I also recognize that people change, so I have to make sure my team knows that if I don’t figure it out on my own, they can come to me any time to discuss how their needs have changed and what we can do to help them feel more productive and accomplished. Employees who believe that you support their desire to achieve their own goals will be more than happy to use their efforts and talents to help you get closer to yours as well.

imageWhat advice would you give someone transitioning to a leadership role?

Surprisingly, moving into a managerial or leadership role can be more of a challenge than actually executing the job once you get there. Not because you’re suddenly delegating orders whereas once you were just executing them, but because when everyone starts looking for answers, they’re going to start by looking at you.

My advice in this case would be to learn to rely on empathy and emotion as much as your executive skills so you can empower your team to become leaders themselves and take ownership of their work. That’s a much harder thing to do than just ordering people around, but the end result is far more rewarding and productive.

In addition, accept that now everything is on you. That means sometimes you’re going to have to take the hit if your team isn’t performing the way you hoped it would. But no one likes a boss that passes the buck to an employee when things go wrong. You need to be the best human being you can be to earn their trust and respect. Back your team up and don’t pass blame, and you will earn their loyalty and their best efforts. And really, isn’t that the best thing a leader could ask for?

imageHow do you instill soul and swagger into a physical product you create?

Do you have soul and swagger? Do you hire people who have it? If so, your product will, too. How many times has a brand or product suffered after the departure of the company CEO? That doesn’t mean the next leader might not be great and continue the swagger, but it all depends on his or her DNA.

imageAre there any common mistakes you repeat? Any tips on overcoming them?

I repeat all my mistakes over and over and over again.

You know why? Because while I regret—really, really regret—any trouble my mistakes at the office cause my team, for the most part I enjoy making them. For example, my team is constantly on me about biting off more than I can chew. Too often, I become the bottleneck, and that slows everyone down and causes them stress. I do try to do better, but somehow month after month it still happens because I love saying yes to things more than I hate being the bottleneck.

And, if I’m being perfectly honest, I’m not going to put in the work it would take to overcome these mistakes. I don’t want to focus on my weaknesses; I want to bet on my strengths. I feel that way about everyone in my life, too. I have such confidence in my team I struggle to think of something we are not great at. There must be something, but it’s not where I put my time and energy, so it doesn’t really register.

Some people might think this is willful blindness, but I say betting on your strengths might be the most underrated strategy in modern business. At home, you have to pay attention when mistakes or weaknesses threaten your personal or family life, but in business, if you’re an entrepreneur and the boss? Nah.

imageAre you worried you might have created a Steve Jobs–esque “reality distortion field” around VaynerMedia?

What a flattering question. For those of you who don’t know, reality distortion field is a term used to describe the magnetic hold the late Steve Jobs seemed to have on his designers. By sheer force of personality and charisma, he seemed able to dissolve any doubts or questions about his strategies or plans. I’m not worried about that because I know my intent is pure. Sure, I’m probably creating distortion. I think since our job is to get a large group of people to coalesce around common goals, most leaders have to, and it’s all for good.

imageDo you prefer to be around people who are the same or different than you?

A few years ago I noticed that some of my friends were surrounding themselves with yes men and women, and I took a step back to make sure I wasn’t doing the same. Sometimes I know I can be so forceful in my opinions that I suck all the oxygen out of the room. Guilty. But I do value what other people have to say. A solid debate is as s@xy as—and sometimes more so than—a mutual admiration society. For someone who talks as much as I do, which is constantly, I listen quite a bit. In fact, I’m watching and listening all the time, so when I do talk, I’m usually sharing the intel I’ve gathered. I don’t talk just to hear my beautiful voice.

In the end, I don’t meet a lot of people like me, and that’s probably good for the world. In fact, I would say as I get older I am more and more interested in finding people who are different from me and can round out my skills.

imageIf you were to tragically die today, how well would VaynerMedia do long term without its CEO? Have you been satisfied with Wine Library’s performance since leaving to focus on VM?

If the DNA of a company stems from the top, then it makes sense that it will stagger if something happens to a key player. My brother and cofounder, AJ, is ridiculously capable, but I’d assume if something were to happen to me he’d be pretty torn up. He’d better be, anyway. And knowing him, it’s possible he would wonder whether there was any point in continuing. So it wouldn’t surprise me if it were other people in the team who insisted on keeping the business going. We’ve built an interesting culture, and I think in the end it would survive and eventually thrive again, especially once AJ was ready to take the helm if he chose to.

As for Wine Library, I really thought it would suffer more without me than it does. It’s all run by family and close friends, and they’ve done a great job. Do I think it could be doing better? Of course, because I think I’m great! They can’t experience hypergrowth when I’m not there. That’s what I’m best at. I can grow businesses fast as sh@t. But they have other great talent around.

imageWould you be able to lead any type of company? Do you think leaders can switch industries easily?

I 100,000 percent believe I could run most $500 million or smaller companies (any bigger and I’d have to spend some time there to be sure). Now, I don’t know crap about 93 percent of companies out there, but with my spongelike skills I could quickly learn what I need to know about any B2B or B2C by studying the data, the numbers, the culture, the marketplace, and the consumer, and then reverse-engineer it.

And you know what? I don’t think I’m that special, either. I think anyone who is good at both sales and HR could do it, because there are two mandates to running a business—build teams and sell stuff. The level at which you will be able to perform will be capped by your level of talent, but anyone who’s good at both is in a position to succeed at the helm of a company. Any company.

imageWould you be willing to sacrifice your ethics for a business win?

No, and not just because I’m obsessed with the idea of leaving a good legacy, but because, practically, it’s the right thing. For one thing, I’ve found that I make more money if I don’t immediately grab what’s right in front of me. For another, I’ve made it clear I think leaders should be role models and walk the walk. I have an assistant with access to my emails; he’d know immediately if I did something shady or unethical, and then he would have to question everything I’ve ever said to him, and he’d stop trusting me. That would slow us down, and ultimately he would talk, which would change the narrative of who I was and what I was trying to accomplish.

A healthy company culture built on trust and openness makes business go faster. There’s debate, but no one is wasting a minute questioning anyone’s motives. Over the course of my career I will probably end up leaving a lot of money on the table because I’ll be judging my success by how many people I think will come to my funeral, not how much money I ultimately make. And I wouldn’t sacrifice that at any price.

imageI want to encourage people to do what I did and leave a very secure job to pursue their dream. But will my employee retention rate drop? Has yours dropped since you started building up your personal brand?

The only way to build retention is to make it clear to your employees that you want them to be happy and live their dreams. That kind of support builds insane loyalty. My employees know without a doubt that I want to win, but not at their expense. I want to buy the New York Jets with them. I am well aware that some of them have dreams that might take them away from this company, and me, and if that happens, they will have my blessing and my support. In the meantime, however, I will try to bring them so much value over the long haul that they will have to think twice, maybe even three times, before deciding to leave. I think it’s sad when leaders and managers feel threatened or betrayed when they find out a valued employee is ready to move on. Our job as leaders is to empower our teams and root for them. Most of the time, if we do that right, we have a chance of building a relationship that can benefit us both whether we’re working in the same company or not.

imageHow important is failure?

This question came to me when business icons Jack and Suzy Welch were hosting the show with me. Every one of us had our own story. As a young man Jack blew up a factory. Suzy was fired from the Harvard Business Review. When I was a kid I paid $400 for a table at a baseball card convention and not a soul showed up. It was my first business mistake and a huge failure; back then $400 seemed like a billion. Every one of us learned an important lesson from our awful experiences. We learned that failure doesn’t kill you, and that the earlier you do it, the easier it is to recover. We gained empathy for others who have gone through the experience. As Jack said, it’s not the failure that’s so important as how well you ride after you get knocked on your butt.

You have to quantify your failure, of course. If you fail and you can’t get up again, that’s not a good thing. But if you’re made of the right stuff, failure will just compel you to get back up and try harder. Any failure from which you can recover is a learning opportunity that will only make you stronger.

Don’t fail too often, but don’t be afraid of it, either. I tell my team I need wartime generals—leaders who can deal with things when they’re not going well—not peacetime generals. I always know what’s going well. What I need to know is where are we failing.

Yes, failure is really important. Failure makes you better. I like failure.

imageHow do you celebrate victories?

I am terrible at it, and that’s not something I’m proud of, because when you don’t celebrate your wins, you hold your company back. Celebrating victories, in my opinion, is an integral part of building company culture.

At VaynerMedia we have big wins every day. We land big new accounts. We grow like crazy. We win awards. And yet I celebrate very quietly. You’ll never hear us cheer, you’ll never see a press release, you’ll never see me pound my chest. Which doesn’t mean I don’t ever brag about our successes—three minutes of The #AskGaryVee Show (heck, three minutes into this book!) and you know I’m proud of what this agency has accomplished. But when I do mention our victories and accolades, it’s usually long after they’ve happened.

It’s all because I love the climb so much. Many entrepreneurs are like that. We’re so focused on the journey, by the time we’ve gotten to the top we’re already thinking about the next hill. You just get to the next battle so you can win it. But this can be dangerous and unfair to the people who helped you with that climb. Some people like to pause and enjoy the air up there. If you move right along without acknowledging their efforts and celebrating the moment, they can feel used and unappreciated, especially if you’re the only one to reap the bulk of the rewards.

I know this is a weakness and it’s one I think is worth working on. It’s up to me to shape our culture, and I want my company to be a place where we celebrate our wins as a team. It’s important to stop and smell the roses, but sometimes you need to hand them out, too.

imageWith such a busy schedule and so many obligations, how do you find the time to focus, be nice to people, and stay in the moment?

The New York Times published an article that said incivility in the workplace had risen over the last few decades, and when people were asked why they might behave rudely, they replied it was because they felt overloaded and just didn’t have time to be nice. I call bullsh@t.

Being nice is a choice, and how you choose to speak to people even when you’re pressed for time will reveal who you really are. It has nothing to do with technology or the generation gap. The jerks, especially the ones with power, who are making people miserable at work today would have been making people miserable at work thirty years ago. Money and fame doesn’t change people, it just exposes them. When you’re being watched all the time, it’s harder to hide your true nature. Also, you know the consequences won’t be the same if you decide not to play by everyone else’s rules. Sometimes this can be for good, but sometimes it’s a way for people to stop using their manners and indulge in their sense of self-importance.

I don’t know that I have any other gear but the nice one. I may have a big ego, but I’m very aware of where I’ve been, and I try hard to stay humble and kind. I really do care about people, and they seem to sense that. I’ll take a selfie with someone and then see him or her tweet, “Wow, GaryVee is a really nice guy.” I wish they didn’t seem so surprised.

For some reason the more exposure you get, the more credit you get for being a nice person, and that’s just silly. We should expect more from people in the spotlight or who have built a platform. I not only try to lead by example, I also make it clear to all my senior staff that even as I expect them to execute and produce, I expect them to combat negativity and treat people with kindness and respect.

imageWhen it’s all said and done, how would you like to be remembered?

As the greatest human being who ever walked the earth.

Too much?

As a very competitive entrepreneur who wanted to build the biggest building in town by actually building the biggest building in town, not by trying to tear down everyone else’s buildings.

Or . . .

How about as someone who made an effort to help people do things that make them happy?

I actually do my best to make my daily interactions with people such that they’d want to come to my funeral. The only way to do that is to be memorable. Not in a showy way, but in being unimpeachable in keeping my word, backing up the sizzle, and dealing with others. In other words, all the behind-the-scenes stuff that doesn’t necessarily get written about in the business trades. If all of us did business with that goal in mind, the world would be a pretty great place, don’t you think?

Hopefully it will be a long, long time before my funeral, but I’m hoping for a shockingly big crowd.

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