Smart work will never replace hard work; it only supplements it.
People are your most important commodity.
Patience matters.
Never be romantic about how you make your money.
Try to put yourself out of business daily.
These are my commandments.
So you see, the clouds don’t just represent the big picture; they represent the huge picture, the everything. They are not goals. Goals can be achieved and set aside or moved. I’m Going to Buy the Jets is a goal. It drives me, too, but it’s not at the core of how I run my businesses.
The dirt is about being a practitioner and executing toward those clouds. It’s the hard work. On a personal level, my dirt is making sure I communicate well with my loved ones, that I show up and stay present, that I apologize when I mess up and that I make sure it doesn’t happen too often. You know, the stuff of being a good spouse, parent, son, sibling, and friend. Professionally, it’s knowing my craft. It’s knowing there is a fifteen-person limit to an Instagram chat and that infographics overindex on Pinterest. It’s understanding Facebook ads and the ROI of Vine. It’s noticing changes and trends and figuring out how to take advantage of them before anybody else.
The vast majority of people tend to play to the middle, which is why they usually only succeed up to a certain level and then plateau. Alternatively, they get stuck in one or the other, getting so bogged down by minutiae or politics they lose sight of the clouds, or so into the clouds they lose the appetite or neglect the skills they need to execute successfully. Ideas are worthless without the execution; execution is pointless without the ideas. You have to learn to prioritize properly and quickly identify what’s going to move you further ahead and what’s going to make you stall.
I saw how these tendencies played out early in my career in the wine industry. I encountered a lot of amazing wine people with brilliant palates whose businesses stunk because they weren’t good at that part. Conversely, I’d meet with some of the best wine retailers in the country and be shocked to find that their actual knowledge about wine was incredibly limited. A great wine merchant has to be a businessperson first and a wine person second, for sure, but that second part really did matter. I always thought the reason the success of my family wine business, Wine Library, accelerated so quickly once I got involved was that I took both seriously. I knew my business, but I also knew my craft, and that practitionership—loving wine, tasting as many as I could, and caring about the regions and producers—created tremendous value for my customers and ridiculous ROI for me.
I see a similar phenomenon in today’s marketing world. At this point in my career I have sat down hundreds of times to meet with people claiming to be social media experts, only to discover they have gaping holes in their knowledge about the platforms and little idea of how they have changed over time. This is why I feel justified telling potential clients that if they work with me, they’ll be working with the best social media practitioner at the best social agency in the country. Because at VaynerMedia, the clouds matter, and the dirt matters, and nothing else.
There are too many people who are average at what they do, and then confused by their average results. Everyone has their own definition of clouds and dirt, but if there’s any advice I can offer you that will change the entire trajectory of your career, it’s to start pushing on both edges. Raise the bar on your business philosophy, dig deeper into your craft. You want to be an equally good architect as you are a mason. You’ve got to be able to simultaneously think at a high level and get your hands dirty.
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Can you elaborate on what the middle is and why it sucks?
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To be in the middle is to be like everybody else. It’s a start-up that pitches me by saying: “We’re going to do something in the photo app space.” You mean like everybody has been doing for the past five years? It’s commodity work. It’s not influential and it’s not special. It’s safe.
On any given day, I sit through four or more pitches. And the pitch I usually end up liking? The one where the players are actually doing the work. They’re in the trenches. They’re not just doing the big holistic thinking or the higher-level branding; they’re just at a raw level, executing. They’re engaging like mad and experimenting on platforms and trying things that risk getting them ridiculed in the trades. There really aren’t that many people who are hard practitioners like that. There also aren’t that many people who are looking far into the future. I’m talking 2025 and 2030. Everyone is hanging in the middle space, trying to get the most in the short term out of their new app instead of trying to build something that lasts.
Let me put it this way: If you have pages and pages of notes, but no product, you’ve got nothing. If you can’t tell me how you’re going to build your product, you’ve got nothing. And if you are only thinking three years into the future, you’ve got a huge vulnerability. That’s what people in the middle are doing. The middle keeps everything going the way it always has. The clouds and the dirt break things.
All the best apps, companies, and products have broken the way we live life, transformed how we communicate, and changed our day-to-day. Good products evolve us.
You’re surrounded by the middle for 99.9 percent of your life. Most things are unremarkable. I want you to lose yourself in the clouds and the dirt and figure out what you can make that changes the game.
Vagueness sucks. Lack of drive sucks. Half-assing things sucks. And so does the middle.
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How do you know how much time to give to clouds versus dirt? Should you base your decision on your personality? Your strengths?
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You need a healthy balance. If you’re leaning too far one way or the other that’s a problem. I’d be uncomfortable if you were 70/30 in any direction. That should be your absolute minimum.
You do also need to map your DNA. If you’re a big-picture thinker, make sure you’re still spending 30 percent of your time honing your practitioner skills. If grinding and hustling is more your thing and where you want to spend 70 percent of your time, that’s cool, but keep at least 30 percent of your time reserved for getting in those trenches and seeing how your ideas actually play out in the real world. And there will be an ebb and flow. Sometimes you’ll have to switch from 70/30 to 30/70 because you were doing something right, and now you have to make sure all parts of the business, from the strategy to the operations, is caught up and heading in the same direction. At the time this question was asked, I was actually thinking that I would have to move into a 90/10 division of thinking versus execution because for the nine months prior I spent the majority of my time executing, and in that time I had spotted opportunities to rechart the company.
There’s no perfect breakdown of clouds and dirt, but they always need to be in play. You have to make a commitment to strategy and execution and think of them holistically. There are too many prima donnas out there who think that as the brains of the business they don’t have to get their hands dirty.
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When is the long tail actually just moving the goalpost?
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As most of my followers know, I want to buy the Jets. I’ve wanted to buy the Jets since I was a little kid. Three decades later, I’m still at it, but I’m not tired. That’s how long-term I am. Owning the Jets will be a by-product of ignoring anything other than the clouds and dirt. I consider every decision I make—from launching VaynerMedia to writing books to public speaking to doing a podcast and show—as a chess move, and I don’t make it unless it gets me closer to owning the Jets one day.
But I suspect what you’re thinking is, big picture is great but if you’re ignoring all the little stuff in the short term, will you ever really reach your goal? I say yes, because when you have a big picture, a north star, a truly long-term vision, something interesting happens: You stop stressing the dumb little shit day in and day out because you’re playing the big game. So the short-term angs
t, which is really just a by-product of the friction caused by growth, becomes a little more manageable. And when you’re not stressing, you’ve got a whole lot more energy to go all in. If you’re single-mindedly focused on your long-term goal, you’ll be more effective in the short term and get there faster.
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Where do you see yourself in five years?
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I have no idea. I’m not a planner and don’t have a five-year plan. Five years ago Instagram and Snapchat didn’t exist, nor did GoPro. Netflix wasn’t what it is today. The world is changing too fast to be able to predict where I will be professionally. Personally I will be in better shape, I will spend more time with my family. I’ll be going to tee-ball games and ballets and shows and hacking my life to have better balance. Professionally I will be doing what I always do—listening to the marketplace and adjusting on the fly in real time, running a business, and marketing like it’s 2021, 2022, 2027, or whatever year you’re reading this in.
I am a “halftime adjustments head coach.” If I’m down 23–21 at the end of the second quarter, I’ve got fifteen minutes of halftime to figure out how to turn things around for my team, using what I’ve learned, tracking the patterns, and adapting in the moment. In the words of Missy Elliott, I’m gonna drop down, flip it, and reverse it. And that’s how I come out winning 35–24. That is who I am as an entrepreneur. I improvise and adapt to new realities on the ground while always keeping my eye on the clouds.
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What’s the biggest lesson you learned this year?
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This question was posed in 2014, when I was twenty-six days into a new diet and workout regimen designed by the personal trainer I hired to help me get back in shape. I had realized I wasn’t accountable to myself when it came to health, so if I was going to make a change I would need to become accountable to someone else. It worked. At the time, I’d made it to the gym twenty-six times and eaten seventy-eight healthy meals in a row without cheating. Since then I’ve kept it up. I feel so accomplished. I’m also grateful that I figured the solution out at a young enough age that will allow me to reap the benefits for decades to come.
So the biggest thing I learned that year hands down was that prioritizing my health is a really good idea. My energy level was down for a while because I had been living on sugar. But after just a few weeks, I felt like a different person. Making my health a priority has changed my life. And remember what I said about how everything I do is a chess move that gets me closer to owning the Jets? This change isn’t just good for my health or my family; I will be able to build businesses and invest and do what I love to do longer because of it. It’s cloud thinking, which is win-win all the way around.
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What is an area in life where you haven’t given it your fullest efforts?
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There were once two places where I wasn’t giving my all. One was in the nonprofit/NGO space. I was giving my dollars but my effort and time were reserved for my family. Now I’m a proud member of the board of Pencils of Promise, which does require a time commitment, as well as several other organizations to which I donate both time and money. The other was my health. Between kids and businesses and volunteering and working out, it’s hard to find Gary time, and I haven’t figured out how to hack that yet. In September during football season I always get several hours on Sundays. Maybe I should find something just for me that I enjoy during the rest of the year, too, but that doesn’t feel right to me while the kids are still so young.
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What motivates you to continue any project without seeing any significant growth prior?
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I believe in my purpose. I’m blown away by how people are crippled by a project that doesn’t go the way they wanted it to. I have a clear vision professionally where I want to go and so I am willing to be very patient along the way because I have conviction and remember why I believed in doing it in the first place. Otherwise I just want to be a good human being, do business the right way, and hustle. I control all of that. If I don’t get results then it’s because I made a wrong strategic decision. But that doesn’t cripple me, either, because I know where I’m going. For the one or two times I invest poorly or get involved in the wrong thing I’m going to figure out a win alongside of that. I understand in those losses that I am gaining valuable experience.
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Does VaynerMedia focus much energy on winning awards and what’s your take on the ad industry’s obsession with awards in general?
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I think awards are horsecrap. The reason agencies want to win them is twofold: They use it to recruit talent, and they use it to get more business. They’re putting out work for clients that’s geared toward getting awards instead of trying to sell something. I understand the business rationale, but it takes your eye off the prize, which is to do something for business. At VaynerMedia, our work is the word of mouth of our business. I think awards are an energy sucker away from what matters, which is selling the product for the client. Old-school reporting and awards have been the justification for many agencies. I am excitedly waiting for technology to catch up and create more black-and-white data that will prove the results of marketing activities and campaigns.
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If you had a seven-acre vineyard, how would you sell lots of wine? How would you do things differently compared to all the other vineyards out there?
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Clouds and dirt. Or as I used to say to my dad, big and small. If I had a small parcel in New Zealand and wasn’t making that much wine, here’s what I would do:
Small: hand sell. I would fly to the big cities in Australia and New Zealand and walk around to visit restaurant sommeliers. I’d go restaurant by restaurant, retailer by retailer, and try to get in their door. I’d offer tastes and sell to every individual, thus scaling the unscalable.
Big: become a media company. I did that in 2006, and it’s what I’ve been saying everyone should do for years, no matter what their business. While working at Wine Library I was doing the small stuff—the tactical email service, the website, working the floor on a Saturday. But then I started doing the big things, like Wine Library TV. You, small New Zealand winery, need to become the authority on New Zealand food and wine. Put out written or video content on as many channels as you can and start talking. Talk about your products. Talk about your competitors. Talk about what goes with wine, and why we drink wine, and why New Zealand grows great wine grapes, and what to eat with wine. Talk wine, talk New Zealand, talk with passion, confidence, and expertise. There’s room for everyone at your level. Become bigger than you are.
Small: Don’t get caught up in the glam. When Wine Library TV took off I started getting interview requests and media coverage, appearing on Conan and Ellen and Jim Cramer. But the whole time I was still downstairs hustling, still trying to get a good deal on Barolo, still answering emails and engaging with people on Twitter, and trying to sell another bottle. Even as you start to taste success, you have to have the humility to get on a middle-aisle seat to the Philippines and sell a few bottles of wine to some random restaurant.
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What would you prioritize as a one-person business?
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The answer is the same whether you’re a solopreneur or part of a team running a small business.
In the beginning of any venture, it can be difficult to predict your cash cycle and know what to prioritize because everything feels imperative. Customer satisfaction is huge, as are issues like establishing company culture, budget, marketing, and hiring.
But there is one thing that always transcends everything else:
Cash. It is the oxygen of your business.
You can make the greatest cup of coffee, the greatest sneaker, the greatest TV show, or the greatest work of art ever, but if you can’t sell your product you are out of business. So your first priority is sales because it generates cash, and cash is what allows
you to do everything else. Without it you’re a fish out of water, gasping for breath.
I can’t say it enough times: Cash is oxygen.
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If “Cash is oxygen” is your priority as a one-person business, what’s second? Product, team, or service?
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There is no second.
That doesn’t mean there aren’t other things you need to concern yourself with that will affect the success or failure of your venture. Ignoring customer service or your product quality or company culture is a very bad idea that will ultimately sink your business. It’s just that ignoring them will probably sink it a little more slowly than running out of cash will. Your business isn’t that much different from a human body. It will run on sugar and caffeine. It will run even better if you give it water, vegetables, and a workout. But it won’t last five minutes without oxygen.
So let’s say you’ve got a good handle on your cash flow. How do you figure out what’s next?
Focus on your strengths. What else are you really good at? Design? Growth hacking? Nail these skills down, and then drill deep with them. If cash is your company’s oxygen, your strongest skills are its DNA. Develop and cultivate them because they will be the hallmark of your company.
For example, I’m really good at growing top-line revenue, so that’s what I focused on in the early days of both Wine Library and VaynerMedia. It was only later that I worked on driving profit back up.
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