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I write books for many different reasons, including the financial incentive, the extra exposure it offers . . . and okay, yes, my ego. But one of my driving forces when I get an idea for a book is: Can this actually help somebody? Could it change the course of someone’s life? Crush It! did that. Seven years after its publication, I still get hundreds of emails from people telling me how that book inspired them to follow their dreams. I hope this chapter could be that powerful for anyone in a family business or considering going into one.

I’ve run two family businesses, the first with my father and the second with my brother. They’re as complicated as business gets. One of my favorite cautionary pieces of advice is that one of the best ways to go out of business is to make emotional decisions, to get romantic about how you make your money, or to let your emotions get in the way of the task at hand (see Chapter 10 on Facebook ads for an example of how emotions can hold people back and create openings for other, less emotional operators). I say that, and yet I know there is nothing more emotional than dealing with the conflicts that arise within family businesses. There isn’t a week I don’t get emails asking, “How can I get Dad to let me try something new?” Or, “How do I convince my mom to join the twenty-first century?” Believe me, I’ve been there and I feel you.

I try to tread lightly because every situation has its own dynamics and variables, but there is one thing I can say that I hope is universally helpful no matter what kind of situation you’re in: If you and your family love each other more than you love the business, you will succeed. There’s no question in my mind that that has been the bedrock of why it worked out so well for us. In addition, we’ve put a lot of hard work into the relationships themselves. I often wonder what my relationship with my dad and brother would look like if we weren’t in businesses together. I know no other way of relating to my father, but there was a time when we were growing up that my brother and I had a more carefree dynamic than we do now that we’re in the trenches together. At one point we had to start scheduling non-work-related meetings to rekindle our brotherly relationship away from the workplace.

Most people will advise families not to risk family harmony by going into business together. I totally disagree. I say if you have the opportunity, go in headfirst. I’m passionate about this topic and have spoken to a lot of people about it over the years, and even the five to seven dozen I’ve met whose foray into business caused their families to explode like atomic bombs—to the point where they weren’t speaking to each other, sometimes for years—even they eventually admitted that they were grateful for the time they had gotten to spend day in and day out with those family members. For that reason, I feel comfortable telling you that if you’re debating whether to take the leap, it’s a good decision and you will not regret it.

I can honestly say that there’s nothing I’m more grateful for in my professional life than the opportunity I’ve had to work with two of the people I love the most in the world. It hasn’t always been easy. It has taken a ton of emotional equity and enormous amounts of empathy, self-awareness, and compassion. But it has also honed my communication skills in a way I can’t even quantify. Who needs Stanford or Wharton when you’ve got a family business to school you? Despite the days I cried in my dad’s office, despite the hard conversations I’ve had to have with my brother, I think I’m the luckiest man alive to have what I have with them.

imageWill you force your children to partake in the business like your dad? Will you be disappointed if they don’t want to?

From the very beginning, I was a crap student and a great salesman. My dad knew what he was doing when he dragged me into the store at the age of fourteen. That said, if I had hated it and told my parents it wasn’t what I wanted to do with my life, they would not have forced me to stay. My brother, AJ, worked in the store for only one summer, because it was obvious to my parents it wasn’t for him. Plus he was a great student.

My parents were all about giving me opportunities to bet on my strengths, and that’s the kind of parent I hope to be, too. I want to put my kids in a position to succeed, and I think sometimes that will mean challenging them. They need to know success doesn’t come easy. For example, when my son, Xander, was two and a half years old, he had a basketball net in the living room. I used to play with him, but then he started to cry every time I picked up the ball because he knew I was going to block him. That’s right, I wouldn’t let my toddler son score (not even one basket) at living room basketball. Because I want him to learn that anything he wants in life, he’s going to have to earn it.

Maybe my kids will become powerful businesspeople. Maybe we’ll go into business together. And maybe they’ll turn out to be schlemiels who couldn’t sell water in the desert. I won’t care. Lizzie and I will love them unconditionally. All we’ll ask is that whatever it is they choose to do, they give it all their heart and do it to the best of their abilities. If they decide their life’s work is in saving the one-legged butterfly, then I will do whatever I can to help them do that. Our job isn’t to prepare our children to live our dreams, but to live their own.

imageHow important is it for your significant other to share your entrepreneurial vision? What was Lizzie’s impact on building your empire?

Growing up I would always roll my eyes when I’d hear the classic adage “Behind every great man is a great woman.” It didn’t make sense to me. I was on the front lines hustling my face off and doing great with no woman backing me up (except my mom, which is a totally different relationship). Who needed ’em?

Then I fell in love. I matured, I became a man, and I realized how wrong I was. I’m absolutely flabbergasted by Lizzie’s impact on my career. Her support, her complete and utter 100,000 percent support, is what gives me the headspace I need to be all in and do my thing at VaynerMedia.

I don’t mean to say that I wouldn’t have been successful without her. Without a doubt I would have. But I’m sure I would have been an unhappier person, less healthy, and less fulfilled. She makes my life whole, which means I’m not spending any brainpower worrying about the stuff in my life that isn’t great—it’s all great. My personal happiness means that unless I’m with her and the kids, all of my energy can be devoted 100 percent to my businesses. And I can do that for enormous amounts of time every day because of Lizzie and the way she supports me.

It’s absolutely crucial for entrepreneurs to have as much freedom to execute on their vision as possible. But sometimes when you’re in a relationship or you have family obligations you can only give 70 percent of your time. Or 50 percent. That’s totally fine. Success is not a game of absolutes. You can still win; it just might take you more time than you hoped. Regardless of your situation, building a business is without a doubt a huge time and energy commitment, and you and your spouse or partner need to be realistic about that. However you conduct your life and business, make sure you’re both on the same page. Keep your communication lines strong and open.

That said, if you love someone he or she needs to take precedence over everything else. And that’s okay; it just means your career may have to go at a different pace or take a different path, because otherwise there will always be friction between your two loves.

Having a supportive significant other is not the only thing you need to succeed as an entrepreneur, of course, but it will make the whole endeavor go a lot faster. And it’s definitely a lot more fun.

imageHow did you deal with the specific challenges of working in a family business?

Carefully. Family businesses are difficult because of the emotions and history that inevitably come into play. Yet now I’m in my second one, and I hope to run one with my kids one day. I think the reason I’ve had a good experience working in family businesses is that my mom and dad taught us that our love for one another should always trump our pride and competitiveness. We fought a lot, especially over our vision for the business, but we never allowed ourselves to go to sleep really angry after a blowup. Somehow we always managed to settle our differences before the day was done.

In every family business, you have to create an environment where the family’s love for each other matters more than anyone getting their way.

imageHas any business challenge ever tested your relationship with AJ, and if so, how did you work through it?

I’ve struggled a lot less working with AJ than I ever did with my dad. Their personalities are different, and my role in the business was different. I started off as No. 2 at Wine Library, but at VaynerMedia I’m No. 1. AJ is very good at telling things like it is and not backing down. When he was nine and I was twenty we started an eBay business together. It originally started at 70/30, but then one day he came to me and told me the split would have to be 50/50 because he believed the work he was putting in was worth half even though I’d put up all the money and had taught him the game. And when we started VaynerMedia, even though I was already in the market and had all the leverage, and a lot of the business was built on my personal brand, we decided that again it was important that we go in 50/50 to start the business out on the right foot.

We’ve disagreed, of course. He was absolutely convinced that we couldn’t ask clients for a fourth of the retainer fee we get paid now. I enjoyed proving him wrong on that. And I’m sure if he were writing this book he could include a few stories where he proved me wrong. But overall, we are perfect partners. He’s the straight man to my magic, but beneath the quiet surface there’s an extraordinary maturity and self-awareness that serves him very well. Plus he’s got his own brand of magic that brings tremendous value to our company. Six years into this venture, and we’ve never had a massive blowout.

Here’s the thing to remember if you’re going into business with a family member you love: Be the bigger man or woman. It always works. No matter what the disagreement, no matter how heated the fight, make sure to say “I love you.” Those words are what keeps family businesses alive.

imageWhat do you think AJ has learned from you in business?

I let AJ answer this one and was touched by his response. What struck me is that the lessons he’s taken away from working with me are exactly the same lessons I try to teach all of our employees and everyone in the Vayner Nation. Say what you will about me, I’m consistent.

So what did AJ say he had learned?

1.Keep things in perspective. In the course of building a business fast there’s a lot that gets thrown at you, some good, some bad. You have to keep the highs from taking you too high and the lows from dragging you too low.

2.Focus on what’s important and on the big picture, and don’t stress out over the rest.

3.Personalize your interaction with your employees. Some companies stick close to the HR book to protect themselves and make processes faster and more efficient, but we don’t use a cookie-cutter system. Every situation is unique and calls for a different approach. By treating people with respect and recognizing their individual achievements and skills, we’ve built a strong, loyal team that really brings its best to the office every day.

imageIf your kids want to join the family business, will you start them at the bottom?

Well, by the time the kids are old enough to join the family business there’s a good chance the family business will be the New York Jets.

Regardless, I guarantee they will start at rock bottom if they haven’t had a chance to go out and live a little first, and if they have, then I’ll put them in the place that will benefit most from their education or skill set, just like I’d do for any other hire. More important, I won’t let them ascend to be No. 1 unless they deserve to ascend to No. 1. That’s something I’ve been firm about at VaynerMedia. We have friends and family in both businesses, and they’re all playing at different levels. No one gets put in a power position unless they’ve earned it.

Who knows, maybe I’m underestimating how much my enormous love for my kids will color my objectivity and judgment when it comes to deciding what they’re qualified to do, but I’d like to think my huge respect for American meritocracy and capitalism will override my paternal feelings. In addition, when you are building an organization the people who grow it with you become family. By the time my kids are ready to be in the business there could be fifty people who have been working here with me for twenty-five years, and at that point my love for them will be extreme. Not as extreme as the love I feel for my kids, of course, but damn close. If my kids come on board, they will have to respect that and deal with it.

imageI’m in sales for a third-generation residential construction company and getting my “at bat.” How do I increase business but keep old minds happy?

I was extremely fortunate because my dad gave me plenty of room when I was at Wine Library to try out new things and test ideas. And since those ideas allowed me to make a huge and immediate impact, I had a lot of “air cover” to do my thing. So I never lived this problem. But I feel like I’m living it now at VaynerMedia. I’m working with clients who are strongly grounded in the old ways of B2B. They can be so skeptical, so hesitant. And I’ve found that when dealing with these kinds of people, you have to get a little real, even a little harsh. I have no problem telling them aggressively and with conviction that clinging to romantic notions and tradition is the quickest way to go out of business.

You’re going to have to do your version of the same thing. Too many young people in your position spend all their energy trying to make their dads and grandpas and great-grandpas happy, tiptoeing around them and trying not to piss them off. But how can the business adapt to the new year and the new era when everyone is still doing what their grandpa or grandma did? For your business to stay relevant, you have to change. You don’t have a choice.

But old minds are tough to move. You’re probably going to have to try several angles to see which one will get them to accept your new ideas. Some might respond well to kindness and sugar; others will only hear you if you go extremely rogue and aggressive. You might need to be stunningly compassionate or massively disrespectful. Try every option until something works. You really don’t have any other choice.

I get it. No one wants to ruin Thanksgiving forever. And it would be a real blow if Grandpa fired you. But remember, you don’t need to be rude, or yell or fight. You do, however, have to be blunt and stand your ground. Bring backup. See if you can get anyone else in the business on your side before making your final stand. Bring incontrovertible evidence. Your grandpa or dad may still dig in his heels, but if he’s a good businessman—and you have to assume he is to have kept things going this long—he’ll give your idea a second look.

Most important, should Grandpa back down and give you the keys to run this show, you’d better execute. Oh man, you’d better execute. Because if you don’t you will be forever in his eyes the naïve kid in the family.

If you want to move mountains, you’ve got to come with thunder.

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