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Sometimes kids ask me questions on The #AskGaryVee Show, and I’m always struck at how much they take all the opportunities at their fingertips for granted. Of course they can get two thousand views for their makeup shows shot from their bedroom. Of course they can just reach out to a seasoned entrepreneur and ask him a direct question. Every time I see their happy, hopeful faces I want to scream, “Do you know how lucky you are? Do you know how much closer I’d be to owning the Jets right now if I’d had access to the Internet back when I was your age?” My God, the things I could have done.

And now more people than ever are doing those things, because that’s the kind of change the Internet has brought on our society. It’s why so many of us can start building something incredible even when we’re just sitting at a makeshift desk in a broom closet. It’s why we’re able to talk to each other, network, reach influencers, find inspiration, and engage at a level unseen in human history. We are all so, so lucky. It’s such an exciting time to be an entrepreneur—heck, to be a human being!—and I’m pumped at how many people are going out into the world with their ideas and their hustle.

I get a lot of questions from entrepreneurial newbies and restarters looking for everything from nuts-and-bolts platform explanations to reassurance that they’ve actually got what it takes to succeed. I try to answer as many as I can because if there’s anyone I know I can help, it’s this group. I often say there are two core things that bring people value: 1) entertainment, and 2) utility. I know this chapter falls in the latter category, and not only for the entrepreneurs just starting out. Old-timers, pros, and establishment icons, don’t pass up this opportunity to see what’s on the mind of the new generation. Even if you think you already know all the answers, you might be surprised. And their questions—not to mention their eagerness, their fears, and their sheer excitement—can be good reminders as to why you decided to hop on this awesome, crazy train in the first place.

imageFinding a marketing job out of college is tough, especially one that’s not sketchy. How do you find a job that is the right fit?

What’s a sketchy marketing job? I can only imagine you’re talking about the lowest common denominator stuff out there, like MLM (multilevel marketing), which relies on a pyramid scheme, or creating landing pages, selling overpriced e-books, or hawking supplements that haven’t been vetted. I can see why you’d think that was dark, bad stuff.

But most of the marketing world isn’t like that. There are plenty of reputable marketing and social media agencies looking for talent, so you need to recalibrate and raise the bar on your search. If you can’t find a quality company to pay you to work for them, apply for an internship so you can prove your chops. At VaynerMedia we’ve been able to offer many of our interns permanent jobs. We’re growing fast so we’ve needed to fill positions, but we also hire when someone proves themselves to us through hustle.

Many internships pay, but if you can’t find a paying position, consider working pro bono and turning that into a great opportunity. You can read about how DRock, my videographer and director, did it in this book. Don’t want to work for free? Well, it seems to me that if you’ve been struggling to get a job for three or four months, it’s a lot more productive than sitting around doing nothing. I mean, who’s paying you to do that? Take a pro bono half day in a place where you can pick up skills, network, learn your craft, and get an employer’s attention (or at least guilt her into recommending you to someone else). Unless you are literally sending out résumés and interviewing eighteen hours straight per day, you’ve got time to volunteer your professional talent somewhere. Find a place where you think you can make doors open, and put your skills into action. We have become too entitled. Go out and earn that job.

imageHow or should the length limitations inherent on Twitter/Vine/Instagram affect a start-up when choosing its name?

I frequently get questions from people wanting to know the science to coming up with a great business name. Science? There is no science. People will agonize for hours, weeks, months, trying to figure out the name for their start-up, hunting for that perfect, zingy, creative name that allows them to “stand out” and “disrupt the category.” You want to know how you stand out and disrupt the category? It has nothing to do with your name.

Just stand out and disrupt the category.

Are you going to tell me that “Apple” or “Vine” is an earth-shatteringly clever name? Or “Snapchat” or “Reddit”? Do you know how many people tell me they wish they had a different last name so they could use it for their company? They’re talking to a guy named Vaynerchuk! “Oh, but that’s unique and cool and . . .” No, it’s really not. My name is “good” because I made something out of it.

What did “Google” or “Facebook” mean to anybody when they weren’t the household names we know today? You want people to recognize and remember your name? Earn it. Of course serendipity and good timing can play a big part in any product or start-up’s success, but none of that is even possible without a whole lot of hustle and sweat first.

If you’re really worried about your name taking up too much space in this short-form era, go with an abbreviation. No one seems to care that I’m often signing off as GaryVee nowadays. You can also let your audience abbreviate for you. People will help you evolve your name so long as whatever you deliver brings them value.

Here’s my two cents: Stop worrying about coming up with the perfect name. Yes, a good name carries some marketing power, but at the end of the day if the product sucks, the name means nothing. If you have a clever name, people might stop and notice. If you don’t, they really won’t care. They’re going to assign it meaning based on the experience they have with your brand. So please, stop worrying about your name and start worrying about your product.

imageWhat was the hardest thing about starting up VaynerMedia from scratch?

I’m asked this all the time, and the answer might surprise you.

It wasn’t leaving Wine Library.

It wasn’t launching a new business with another family member.

It wasn’t jumping into the agency world with zero experience.

It was all the options I had at my disposal.

During the first nine months we were launching the agency I was troubled by the fact that there were about eight hundred other things my brother, AJ, and I could have done together, and it was hard not to look back at all those opportunities and wonder, did we do the right thing? In addition, that same year my daughter Misha was born and I published my first business book, Crush It. There was so much going on—was this venture the best use of my time? The second-guessing was brutal.

You’ve surely experienced this kind of buyer’s remorse after making a big decision. Almost everyone has. Kids when they finally pick a college. Managers when they make a hire. Entrepreneurs when they invest. Because you know that there’s always that chance you messed up and missed the next big thing. The perfect school. The perfect hire. The monster dividends. We all have our #onealmond moment. (Not familiar with it? I talk about it in Chapter 16, on investing.) At some point, however, you’ve got to hike up your big-boy pants, accept the decision you’ve made, and move on. After all, you made your decision for a reason, so trust your judgment. There’s no point in looking back. Even if you discover you made a mistake, you’ll be okay, because every option will get you something. It might be a return on an investment, or it might be a lesson learned. Sometimes it’s hard to tell right away which is going to be the more valuable. Either way, so long as you don’t shy away from making decisions, so long as you aren’t content to sit and dither, you will never be left with zero. Suck it up. Make the call. And remember: Be grateful if you’re lucky enough to have too many options. It’s a blessing and a half.

imageHow much of success is confidence, how much is skill, and how much is luck? You seem to have a lot of the first.

I have been lucky, that’s for sure. I could have been born two decades earlier in the Soviet Union and spent my formative years going insane locked behind a communistic regime until I got to the United States in my early twenties, and thus had a twenty-year delay trying to accomplish everything I’ve set out to do. Heck, I could have been born a bus!* Instead I was born during the Cold War at a time when Israel and America teamed up to make a deal with Russia that traded people seeking political asylum for wheat. (Yes, that’s right, I was traded to the States for wheat.) And so I moved here when I was three years old and had every opportunity to live the American Dream. If that isn’t luck, I don’t know what is.

So luck is a really good thing to have, and maybe I’ve had more than my fair share. But it’s not the main ingredient to success. Not at all. As has been pointed out, I have a lot of confidence and bravado. But those wouldn’t be worth much if I didn’t also have the skills and the hustle mentality to execute. I suppose one could argue that even getting the good DNA that allowed me to have confidence and hustle could be considered lucky. And yet, there are plenty of people who start out without much confidence, or who aren’t taught a good work ethic, and they come into it on their own and win.

So it seems to me that success—my success in particular, and I suspect most people’s success in general—is a well-balanced blend—a nice little Meritage, if you will—of luck, DNA, confidence, and hustle.

imageHow long is too long for a fiscally responsible entrepreneur to stay in a safe full-time job? At what point do you have to accept that it’s not going to happen. Is it ever too late to start?

These are going to be some hard words for some of you to hear:

If you have a full-time job, you’re not an entrepreneur. You may have aspirations of being an entrepreneur, and you may have entrepreneurial tendencies, but if you are born to be an entrepreneur you will not be able to breathe for more than ten minutes in a “real” job.

If you’ve been going along fine for a few years in a full-time job and not had the urge to gnaw your leg off like a fox caught in a trap, you’re probably doing what you’re supposed to be doing.

But. If you are between the ages of eighteen and twenty-nine, and you are miserable whenever you work for anyone but yourself, and you feel restless, and you believe in your bones that you’ve got what it takes to run your own show, go do it. Go do it before you take on the responsibilities of a mortgage or a family, before your parents start to need you or you adopt a dog. Do it now while the only person you have to worry about is you.

The best way to become something is to do the work required to become something. Sell, sell, sell. Figure out what it takes to provide value. Learn how to communicate your value proposition. Engage with your customers. Find mentors. Go work for free and under people who can show you the ropes and serve as that point of contact when you need it. Learn the hustle and taste the game. Put yourself in the position to win. You can read as many books as you’d like (ahem . . .) but they’re not going to make you an entrepreneur. What is it Yoda said? There is no try, only do.

Stop waiting for the perfect moment to jump, because it will never come. If you want to be an artist, make art. Want to open a pizza place? Go work in a pizza joint and learn the business. Build an app and stop waiting for Mashable to write about it because they aren’t going to give a crap about it until you put in the hard work of proving it solves a problem, serves a need, and makes people happy.

Start doing whatever it takes. Even if that means selling the very shirt off your back.




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

You know, my gut reaction to this kind of question would usually be to say that you’re being irresponsible if you don’t take a chance to follow your passion and be a happier person. If you have a working partner, you could have a conversation about whether you could maintain your lifestyle on a single salary or what you’d need to do to downsize. But when you’re the main breadwinner of a family? Quite frankly it would be irresponsible to walk away from your steady income unless you have enough savings, a trust fund, rich parents, or some other cushion to help maintain your lifestyle for at least two years after you begin your new journey. I’d say you should absolutely go for it, but only if the decision comes at the expense of luxuries, not at the expense of rent or food. It’s one thing for you to willingly eat Vienna sausages every night for a year, but it’s not okay to put kids in that position.

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 $10–40K 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 often give you the best of both worlds.

imageI love my job but I want to do my own blog and my own hustle. But I’m crippled when it comes to executing.

One of the hardest things about making your dream, or your small business, or your blog, or whatever is just doing it. Taking that first step can often be the only thing standing in your way, because once you start getting sh@t done, the momentum just carries you forward.

There’s no doubt that taking that first step can be terrifying. I get it. I really do. But I also have to wonder, would you be so afraid if you knew no one was watching? See, I think what really scares people is not fear of failure, but fear of failing in front of someone who matters. Like your mom or dad. Your best friend. A sibling. A mentor. A spouse. None of us wants to disappoint someone we admire.

But if you want to be an entrepreneur—if that’s what you really, really want—you cannot give a sh@t about what other people think of you. Not even your parents.

I won’t lie—people will criticize you. They will say mean things, maybe even hateful things, often because they’re jealous that you had the guts to get out there and do your thing, or because they love you very much and are scared for you. And that’s okay. If you truly trust and believe in yourself, you will learn to ignore them and they will learn to accept your decisions. And if you fail and people laugh at you, they’re not worth your time. Ignore them.

If fear is holding you back, think about whose opinion matters the most to you, and then sit down with that person or those people face-to-face. And this is what you say: “I’m about to do this thing, and the only reason I haven’t yet is because I don’t want to let you down. This is a long journey and I know I’m going to make it in the end, but I need to know that if I stumble, you won’t think less of me or turn away. Because that would crush me.” Anyone with a heart would be touched by such vulnerability and show of respect. Who wouldn’t be honored to learn that his or her opinion meant that much to you? Chances are good they’ll promise to have your back. And hopefully that’s all you’ll need to take the next step. You want to surround yourself with people who are going to stand by you and encourage you to get back up, not keep you down.

imageWhat’s the best way to deal with someone who is negative about entrepreneurship? What if it’s your mom?

You know what’s great about entrepreneurship? At the end of the day, one of you is going to be right. Who’s it going to be? The best way to handle this is to stick it to your mom. Go out and execute and enjoy saying, “I told you so.”

Because you must know that her negativity doesn’t mean that she doesn’t believe in entrepreneurship—it’s that she doesn’t believe in you. That probably hurts. I hope it also pisses you off. Nothing gets me more worked up than someone who doesn’t believe in me.

Now, maybe your mom is right. Maybe you are delusional. You need to go talk to other people in your ecosystem and find out what they have to say. If they concur with your mom, you might think twice about your ambitions. If they’re supportive and you can tell they’re sincere, that should help boost your confidence.

Most important, you have to ask yourself: Do you believe in you? If you believe you’re an entrepreneur, then no one else’s opinion really matters. Prove them right or prove them wrong—either way, you’re better off for trying. If you’re asking this question, it might mean that you’ve put weight into your mom’s opinion. I put zero weight into anyone’s opinion about me because I know exactly who I am. Can you say the same? When you can, you’ll know exactly what to do.

imageHow do you make your market embrace your product or ideas when it just doesn’t care about them yet?

I get asked a version of this pretty frequently, which boils down to: How do you take someone from “maybe” to “yes”? How do you make them buy in?

You don’t.

I don’t try to convert anyone. No one! None of the content, none of the things I do—books, keynotes, videos, T-shirts—are done in the hope they will convert a single person. I speak only to the already converted, and you should do the same.

This question applies to much more than just social. It applies to whatever thing you are trying to sell. Period. If you sell fax machines, and your market doesn’t believe in fax machines, don’t try to convince them to buy fax machines! Go find the people who have bought into the fax machine idea and sell to them. Because if you’re too early in a business or a theory where there’s no buy-in, you’ve lost.

People are always marveling at how I manage to get into markets just ahead of the mainstream, but as I always say, I’m not Nostradamus. What I am is practical. I spend zero time convincing people to believe what I believe in. Up-and-coming wines. The Internet and email marketing back in 1997. Google AdWords in 2000. Snapchat two years ago. There were even plenty of people who didn’t believe the market was ready in 2009 when I started VaynerMedia with AJ, but in fact there was just enough for us to build a business, and we grew into it. You need a few people waiting at the end if you’re going to survive, and they were there. That’s how we knew we’d be okay if we skated to where the puck was going to be, not where it already was.

Apply your time and energy to where there is fertile ground. It might take a lot of work to find your customer base, but it sure beats wasting your breath on people who are never going to help you out.

I promise you, the more you reach out, the more opportunities to make new connections will arise. Put in an extra one or two hours every day to go beyond the place you’ve already been looking. It’ll be worth it.





imageWhen trying to create a new media property (say, something at the intersection of food and tech, with no real precedents), how do you find and forge the right partnerships, that is, people with resources and access?

Everybody always has something to offer. When I biz-dev from a zero-starting place, which seems to be where this question is coming from, and I’m looking to extend my reach and resources, I’m always trying to reverse-engineer the most valuable thing I can give to those people.

I think the way to do it would be with something I call shock and awe. I would reach out to as many of these people as I could, as often as possible. But instead of asking them to do something for me, I’d ask what I could do for them. It would be about following them on social or in the media, not about reaching out and asking directly, because let’s face it, these kinds of people are usually busy. It would be about asking what value props you can bring to them.

I’m an enormous believer in spec work. I know it has a bad name, but if you’re looking to get something from someone, there are other ways you can pay them besides money, and providing your service or your product for free is a great way to build up points you can cash in.

For example, I’m always the cheapest, or the most vulnerable, when I’m promoting a book. So for anybody reading this who bought 25–2,000 books in exchange for my time, I think you got a good deal. I discounted my time and my impact in order to make this book a success. So when you assess the fifty people you want to reach, you need to look at them and understand their vulnerabilities to see where you might get them at a discount. Now, if they don’t have those vulnerabilities, figure out how to provide disproportionate value by listening and asking directly.

imageWho would you recommend pitching an app idea to? What steps would you recommend?

At first I was like, what kind of question is this? If you have an idea and you can’t code, you pitch a cofounder or a dev shop to build it. If you need money, you pitch it to money people. When you need to sell it you pitch to a strategic buyer. If you need press, you pitch it to the media and influencers. Who do you pitch it to? Whomever you need at that moment!

Then Steve Unwin (an amazing cast member from the shooooooow) explained to me that anyone who knew I invested in apps might wonder who might have a shot if they came to me. For example, I invested in the wine app Delectable. How did that deal happen? Well, a VC for Delectable knew I had a wine background. He pitched Phil Toronto, who vets my deals, and sure enough when I learned about it I thought it was intriguing. It’s strategic to consider an investor’s history if you want to predict their interests in the future. But then, every single decision you make in your business life needs to be strategic.

imageHow do I get the first ten customers for a creative service start-up?

I once made a video where I showed the visitors to garyvaynerchuk.com how to cold-call potential customers on the air and get people to consider doing business with me. I had no script, other than to articulate exactly what kind of value I thought my blog could bring to anyone who might advertise on my site. It was a short, pleasant conversation that ended with the potential customer agreeing to review some ideas if I ever put them to paper and sent them to him. I’d call that a productive phone call. If I had been a new entrepreneur trying to find those first customers, I would have immediately picked up the phone again and dialed a new potential customer. And then I’d have done it again, and again, and again, for as long as I could that day, and the next, and the next.

To get those first ten customers, you have to grind. You can’t be shy, my friends. Just roll up to every single person in the world who might possibly buy your stuff (meaning who already buys into at least the concept of your idea or product; see two questions up) and ask them to buy your stuff.





imagePR firms offer media training for executives but the quality varies a lot. A lot of companies have grown complacent and just hire the same firms over and over. How do I get on the radar of decision makers (who aren’t actively looking, either because of complacency or because they think all media trainers are essentially the same)?

First and foremost, this is an excuse as much as it is a question. When I started VaynerMedia, plenty of our prospective clients were in the habit of hiring other, more established agencies. Every industry has its market leaders—companies who have done good work in the past and have become the default solution for their client base. Your goal is to become one of those leaders who are automatic go-tos. So first you have to get over your resentment of the competition and realize that you haven’t done crap to establish your brand. The way you can overcome that, in my opinion, is to deliver great work and start creating word of mouth. It’s just grinding and going through the process.

Now, if you’re asking me how to get your first client, you might just have to come in cheaper than you want to. You’ve got to do a lot more business development, networking, advertising, and putting out content. These are the classic, tried-and-true ways for a B2B company like yours to get business. Put out content on LinkedIn and SlideShare. Go to YPO meetings and industry events for the organizations you’re targeting. Or just cold-call and offer your services at prices low enough to bring on clients who can then start recommending you based on the quality of your work.

This is really, really, black-and-white stuff. It comes down to pure execution. If your work is great, that becomes your reputation, and that becomes the gateway drug to bring in business to your sales funnel. You may call the incumbents lazy, but I call it an earned reputation.

imageWhy do you focus on top-line revenue?

A lot of first-time entrepreneurs try driving margins and profit very early on. I do not. At both my dad’s wine shop and VaynerMedia, I focused on top-line revenue. Why? Because you can always drive your profits, but there’s a very small window in which to focus on the top line.

When I run a business, I tend to innovate and be ahead of the market, and so I want to run fast and grab as many customers as I can while I’m still slightly ahead. It also gives me the ability to bring in the people who will keep things running in the background, freeing me up to play offense and concentrate on building my brand and gaining leverage as fast as possible. Because eventually, the market will catch up with me, and that’s when things get interesting and exciting. That’s when people start believing in what I’m doing, be it wines, e-commerce, video blogging, or social media. Three, four, five years down the line, after I’ve already established my brand and gained customer loyalty, then I can start to drive profit. You can always start cutting costs or raising prices at any time, but land-grabbing more customers gives you the leverage and the scale you need to ultimately convert once the time is right. Of course it takes a certain skill to balance your expenses and sales so you don’t go out of business, but I’ve made a good career of pushing those limits. I think my stomach for top-line revenue is why I now have a second business under my belt that grew from $3 million to $50 million within five years.

I understand the desire to play things safe and guarantee you make payroll, but remember, if you take too long to grow someone else is going to come along and eat you up.

imageI have an app idea, with my target market willing to test it, but I need to create the app and I’m not a programmer. Any advice?

It’s the simplest thing to do in the world. MeetUp.com, for instance, has eight hundred different developer meetups. Find the closest one, even if it’s far away, and go find your developer.

I get so many questions like this every day: “Hey, Gary, how do I hire a business partner/developer/assistant?” If you aren’t capable of figuring out something so basic all by yourself, how the hell are you going to make it in that business? Ideas are sh@t. Execution is the name of the game. Just. Make. It. Happen.

You know, seriously, if you have to ask this question, you’re probably out of business before you even start. Think about that before you invest a single minute more into your endeavor. For real.

imageI’m building an app that is probably six months away from a working prototype. What would you suggest I start doing now to build it up so that when it is time for release we’ll have plenty of users?

That’s a tricky one that lots of developers have to figure out every day: How can you promote a product months ahead of the launch date when you’re not even sure what the product itself is going to look like?

The answer is a terrific tactic that works on everything: content, content, content, content, content, content.

Let’s say you’re putting out a productivity app. Go reserve something like dailytimemanagement.com, and then use that domain throughout the months leading up to the launch. Start putting out content for Medium or your blog or RebelMouse that will draw like-minded people interested in that topic and lifestyle, people who are most likely to use the app. Do everything you can to create a hub and community around the very thing your product was built to address.

Then when the app comes out, you pound that community with it. Shout at them. Ask them to test it out. Give them free trials or limited access so they can experiment with it. If they love it, they’ll start marketing it for you with word of mouth. You’ll know very quickly what works, what doesn’t, and what you need to focus on next.

You know what we call this? That’s right. This is a classic example of using jabs and right hooks to build a brand. Flooding your community with quality content and earning their trust until the day you’re ready to make the ask is a tactic that works for everything. Give consumers a place where they can go to learn, discuss, meet other people, and be a part of something. Then hit them really, really hard.

imageWhat is the biggest obstacle to success: lack of time or lack of capital?

The obstacle would be assuming that lack of time or capital is an obstacle. What you’re talking about is excuses.

There are a million things that can stop your success. Your family’s health and welfare. The country where you live or where you’re trying to set up a business. A competitor with a billion dollars and mega skills who punches you out and drops you in the first round. Bad media coverage. A random moment in time. If I were to look down at my phone while driving and kill somebody it would ruin me. There are a million reasons you can find to stop building a business, but almost every time, the real reason why you will stop is not that you don’t have time or money, but that it’s hard.

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 No. 1. And you know what? That’s okay. Thriving at No. 7 instead of stressing at No. 1 would be something to be proud of, and a great way to live.

imageWhat should I look for in a cofounder?

First look at yourself. You have to be self-aware and honest about your weaknesses, and find someone who can make up for them. When you’re considering a candidate, ask yourself if she provides the black-and-white to your gray. Does she love HR when you don’t care? You want to cover the core things that drive a business—a team, a product that works, a revenue model, sales, retention, vision, and execution.

When people go wrong, it’s because they weren’t willing to be honest enough with themselves. They think, Oh, I can get by with my accounting skills. Oh, I’ll figure the legal stuff out as I go along. Um, no. There is something to be said for being intrepid and willing to problem-solve and learn, but you want a rock-solid foundation for your business. Ideally, together you and your cofounder will be a million times stronger than when you are apart.

imageWhat came first at VaynerMedia: clients or employees? And did you ever do the work by yourself?

About two or three months before AJ graduated from college I brought in our first client. We made that customer pay for the whole project up front, which we then used to pay our first five or six employees, all of whom still work here. AJ and I did actually do a lot of the early work on that first project by ourselves. We’re good in the trenches.

I hope you’ll remember that anecdote. One of the reasons so many people go out of business is that they don’t know how to manage their cash flow. You think you’re going to make $80K so it’s okay to have $70K in expenses. But sh@t happens, and if there’s any kind of a hiccup and the money doesn’t come in when you think it will, you’ve got no buffer and you’re suddenly in trouble. Tech people often assume they’re going to keep raising incredible amounts of money, not realizing that once you’re a real company people start making decisions based on what you’re doing, not what you promised you’d do. So anytime you can sell ahead of your expenses, do it.

imageWhat are your tips for teenage bloggers to show brands they mean business?

Do you have traffic? Followers? Content? Engagement? Brands don’t care if you’re 14, 41, or 4,000 years old so long as you show results. They may underestimate you at first, but numbers don’t lie.

imageHow can I filter years of exciting adventures and experiences into value that someone would actually be interested in?

I don’t know. Are your seventy-one years of experience interesting? Will anyone care about what you’ve done?

I’m a person who will automatically value the life advice from someone who has lived seventy-one years, but the rest of the world isn’t like me. So to reach those people, the first thing you need to figure out is the best method to communicate. How are you going to storytell? Do you want to put out a show? Write articles? Blog? Tweet? Podcast? And then once you’ve perfected your medium, how will you monetize it? You could sell advertising, subscriptions, coaching, content. You could organize a community and put on a conference. Tell your story, establish your cred, make your story relevant, build your brand, and the monetization opportunities will come. Humans of New York was simply a Facebook page before it became a cultural phenomenon and landed Brandon Stanton a book deal.

I’m the poster child for how to make money without directly selling. A lot of my contemporaries sell e-books or white papers. I do none of those things. For years I put out my content at scale and built my brand. Eventually, I built up enough leverage that people wanted to hear me speak, and I could charge good money for my time. They wanted me to write books, which I was able to sell to a big fan base. I was able to start a social media agency. I provided value with the content that I relentlessly pump out. You need to do the same.

imageWhen you have a new business idea, how long does it take to implement? Do you run with it? Strategize for a while? Consult with others?

So you’ve decided to take the leap on a business idea. Congratulations! Taking that first step forward is one of the hardest parts of the process.

Now what? How fast do you need to move? Well, that depends. I have sat on businesses for an insanely long time, years even, before I executed on them. Before we started VaynerMedia, AJ and I thought about it for ten or eleven months to make sure we were making the right decision. You could say we let the idea marinate. In the meantime, we almost decided to move forward with a fantasy sports site. But in the end, VaynerMedia won out.

And then there was the time Jérôme Jarre and I had dinner, and literally the next day we had formed a talent agency for Vine stars called GrapeStory.

The key is to make sure you look at your idea from lots of different angles and ask the important questions. If you’re working with a partner, you should be communicating constantly and hitting your ideas, concerns, and thoughts back and forth until you’re both satisfied with the answers.

One thing to which all entrepreneurs should pay close attention is the timing of an idea. Ask yourself (and your business partner, if you have one): Am I ready? Do I have the time to do this right? The biggest failures in my business career have been when I bit off more than I could chew. I’ve mentioned I had an intensely busy 2009 (new baby, new agency, new book). Because of those obligations I wasn’t able to give my full attention to the online wine review website Cork’d, which I’d bought in 2006. It didn’t see the end of 2009.

So choose your battles. Don’t rush anything. Map your life and make sure this is going to get you where you want to be. And stay open to serendipity. You never know what can happen before that one idea comes to fruition.

imageHow do you avoid letting a new business run its new social media plan by itself?

Well, that’s easy. This is a continuous game. I face this all the time, but I’m not worried. I know everything about Snapchat stories. I know what’s evolving on Facebook. I guarantee my clients will never know as much about social media as I do. The best way to stay indispensable is to stay ahead of your clients and always have something more to give.

imageWhat is the best way to scale a business with an inherently low profit margin?

I answered this question with Jack and Suzy Welch when they were guests on the show, and we were all in agreement. You need new products, new innovations, and a new angle. Take the assets you have and deploy them to grow the business—just make it a better business, even a different business, than the one you started with.

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 marketing lures to get people into the store. Those low-profit-margin items were the honey. But then I merchandized the store and built a brand. Customers came in to buy a bottle of Kendall Jackson, but then I sold them a different, higher-margin chardonnay because it was a better wine. They liked it. They came back for more. And while they were there they noticed other higher-margin items, and tried those, too.

Use your low-margin items to drive your business, then use those pennies to invest in advertising and build from there.

imageWhat’s your best piece of advice for a first-generation American entrepreneur, venturing out on her own, away from her family business?

I have two pieces of advice.

1.Be practical. How much money do you have to stay alive, and for how long? Do you have enough money to cover rent, expenses (anticipated and unexpected), and overhead for a year? You should.

2.Be prepared to sacrifice. The minute you decide to launch a new business, you also make the decision to do nothing else but that for the next year, and maybe even two years, but build your business. Every minute of every eighteen-hour day should be dedicated to this endeavor. Your business success will come at the expense of family time, friend time, vacations, and any other hobbies or activities you once enjoyed. This business has to be your entire life, or it will die.

I think a lot of people go into business for themselves underestimating how hard it really is to make your dreams come true.





imageIf you could go back to any time in your life and know then what you know now, when would that be and what one thing would you change in your business life?

This is something I rarely think about, so it’s nice that writing this book gives me the opportunity to go back and address it. I would probably go back to the early 2000s when I was buying “wine” and many other words on Google AdWords. Looking back, I would probably have spent 90 percent less money on ads in Wine Spectator, billboards, and radio, and I would have poured it all into Google AdWords. Most people weren’t paying any attention back then, the inventory was wildly underpriced, and the demand curve was in my favor. Even back then, there was enormous customer activity on Google that led to transactions, and I feel like I left way too much money on the table. It’s why I’ve been so emphatic about Facebook ads during this generation. This, too, will go away.

I’d also go back to that moment for another reason (and this is something I don’t think I’ve ever even said out loud). A lot of the applications that Eric Kastner and I created in Wine Library’s early days—things like emailing people with abandoned shopping carts, or targeting emails based on user’s searches on the site—became industry standards half a decade later. What’s more is that a lot of the companies who built the tools for other companies to execute on those ideas went on to become $500 million or even billion-dollar companies. Many of my own actions were so early that if I’d been smart enough to turn them into products or services instead of just in-house tools for Wine Library, I might own the Jets right now.

imageWhat are the biggest mistakes you see young entrepreneurs make?

It might take the rest of my life to list them all.

Okay, I’m joking. Sort of. No, seriously, I see many Millennials doing great things. But I also see a lot of you making one mistake in particular that I think is making you dangerously vulnerable, and it’s this: You’re building businesses that only work during best-case market scenarios.

It’s not entirely your fault. If you are twenty-one years old today, the last real economic downturn was in 2008—when you were fourteen. You’ve never had to do business in any economic landscape but one on the upswing, in which it is super-easy to raise money to build a business. You’ve been trained as excellent peacetime generals.

The problem with that is that today’s current market conditions are not allowing young entrepreneurs to cultivate strong business discipline. This is a great time to be starting a business and trying to sell it, but what happens when the bad times eventually roll around again? The best businesspeople aren’t just good peacetime generals, they’re fierce wartime generals, too.

So how do you prepare for war during peaceful times? Start thinking worst-case scenarios. Imagine a stock market collapse. What will you do if all of a sudden everyone snaps their wallets shut because they’re too scared to invest?

Protect yourself before you have to face that situation. Here is what young entrepreneurs must do ahead of time if they want to build a business that can weather every storm.

1.Build solid teams. In the midst of rapid growth, don’t lose sight of the importance of longevity. Invest in your teams, celebrate their victories, listen, and be a good boss so that when rough winds hit, you can rely on their skills, loyalty, and intellectual capital to help you keep the ship upright.

2.Build good products.

3.Excel at sales.

Without sales you’ve got nothing, in good times or in bad. Do whatever you need to do to build the most kick-ass sales department you can find.

Young entrepreneurs are operating during a very sunshiny moment in time. Don’t let your skill set be limited by it. Because bad times are coming. The good news is that good times will follow. And then the bad ones will return. And then get chased away by the good.

Get it? Be ready for every possible outcome. Only entrepreneurs with the grit will rise to the top, and stay there.

imageHow do I overcome the perception of being “too young” when I’m pitching VCs?

I have no pity for any young person coming into the business world today. Twenty years ago the only thing you would have been allowed to do in the business arena was serve coffee. That all changed because of tech. No one today is going to dismiss a young person unless that young person hasn’t got the goods.

The secret to raising money is to sell your idea to people willing to buy. If you’ve been told you’ll get forty-five minutes for a VC pitch, and you can feel it isn’t happening, cut things short and leave. You have better things to do with those thirty minutes. And once you leave that office where you were basically told you couldn’t win, get out there and prove them wrong.

Let me assure you of one thing, however. If someone tells you they’re not giving you money because they think you’re too young to do what you say you can, they’re not telling you the truth. They’re being nice. Every VC in the game will be pumped to give a twenty-year-old money if they believe in that twenty-year-old. If they don’t, it means they see a flaw in your idea or your execution. What you do with that feedback is up to you.

imageAs a successful solo entrepreneur, do I have to grow my business bigger than I can handle alone?

Depends on what you want in life. Are you fulfilled and making the money you want? Not everyone is a good manager. Plenty of entrepreneurs have grown their businesses only to realize that once the scope of their role changes they aren’t enjoying themselves anymore. You don’t want to make more money just to give up your happiness. There’s got to be a sweet spot in your growth where your money and happiness are aligned. I’m lucky—what I love creates a lot of wealth. But lots of people would hate living the way I do. So figure out what you need to be happy, and grow your business just enough to get you there.

imageWhat fundamental skill do many entry-level marketers lack?

Who cares? I never worry about what you don’t have, but about what you do. Because I believe in betting on your strengths. Everyone is different, and everyone will bring a different set of skills to the table. If you’re trying to get an entry-level position, you have to figure out what skills you have that will bring value to your employer, and then hone those skills to the best of your ability. If you get an interview, go in knowing who you are and spend all your time talking about how you can bring value to a brand, company, or department. Someone is going to see you’ve got what he or she needs.

imageHow can I converge my vision of being a YouTuber with my parents’ vision of me getting a university degree?

Once you graduate, people will be interested to know what school you attended, but very few will ever, ever ask you to tell them your GPA. Do what you must to make sure you meet all the requirements to graduate and focus the rest of your time on building your brand, so that once you’ve got that diploma in hand, you’ll feel good knowing your parents can sleep at night, and you’ll have laid the groundwork to becoming a YouTube sensation.



President of InboundMed.com

imageIf you have a Plan B, does that mean you are setting yourself up for failure? Should you never have a Plan B because you should be confident in your Plan A?

I believe in having a hard-core Plan A alongside a deeply practical Plan B. You’d be crazy not to at least consider what you would do should your entrepreneurial venture fall apart. After all, you’ve got to eat. For most people, the solution would be something very ordinary like going back to school, taking a boring day job, or moving back in with your parents. And that’s fine.

You shouldn’t go into your Plan A with blind faith, but I wonder if sometimes the people who fall short of their dreams didn’t take too much comfort in their Plan B. If I had to break down the energy I have and have witnessed in other successful people, I’d probably say we allocate something like 97 percent into our Plan A, and 3 percent into Plan B. A lot of people who want to play things safe probably invest their energy more 75/25, or even 50/50. And that’s deadly. Forgive me for sounding kind of Zen, but if you’re focusing that much on your backup plan, you’re putting out too much failing energy.

What was my Plan B? I think in the back of my mind I knew I could always make a living buying stuff at garage sales and selling it on eBay.

Although, when I say the thought was in the back of my mind, I mean it was way back there, in the deep dark place where I dumped every Spanish verb I never learned. Because if I’m totally honest, I was always sure I’d win.

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