If you want to see the future of work, just look at Gary Vaynerchuk\u2019s DMs.<\/p>\n
He\u2019s spent his career pushing people toward action \u2014 telling them to build something, to own something, to take control of their lives and financial destinies. Now, millions of entrepreneurs and career-builders turn to him for advice, DMing him their most pressing and personal questions. The patterns of their anxieties tell a story: Here\u2019s what people need now. Here\u2019s what bothers them the most.<\/em><\/p>\n Today, Vaynerchuk is seeing something new and interesting: \u201cThey\u2019re feeling trapped,\u201d Vaynerchuk tells me. \u201cThey\u2019re starving out there.\u201d<\/p>\n Why? Because they have one main job or company, but they want more. Maybe their economic anxiety is pushing them to make more money or to find more lines of revenue. Maybe they\u2019re watching the rise of AI, seeing how it can make their lives more efficient, and wondering what else they can do with their time. Whatever it is, they want to expand. But they don\u2019t think they\u2019re allowed to.<\/p>\n Entrepreneurs and professionals have been told a very specific story: Success requires relentless focus. Pour everything you have into one thing. Commit yourself to it fully.<\/em> As David Packard (of Hewlett-Packard) famously wrote: \u201cMore businesses die from indigestion than starvation.\u201d In other words, the greatest risk to your business isn\u2019t doing too little. It\u2019s doing too much.<\/p>\n Vaynerchuk agrees, to a point. Many people thrive with focus. And a business requires dedicated operators who think nonstop about its needs and opportunities.<\/p>\n But many people are built differently, he says. They are the creative thinkers. The restless builders. The ideas people. They have boundless energy and ambition, and it drives them to start new businesses or seek new accomplishments outside their day jobs. And here\u2019s the most important part: For these kinds of people, doing one thing is stifling<\/em>. It drains their energy and makes them less productive. But when they\u2019re let loose, everything they do thrives.<\/p>\n So if you want more, Vaynerchuk says, you should get more. \u201cMore\u201d means more personal and professional satisfaction. You\u2019ll create more opportunities for your team, and have more energy and enthusiasm and ideas for everything that you do. \u201cFor literally more than 50% of you reading this,\u201d he says, \u201cyou need this for your soul.\u201d<\/p>\n But it requires know-how to make this happen. Because \u201cmore\u201d requires strategy and intention \u2014 or else, yes, everything you do really will fall apart.<\/p>\n Vaynerchuk offers himself as living proof of how it can work. He may be known for his social media output, but he\u2019s equally prolific as a builder of companies \u2014 having founded\u00a0the ad agency VaynerMedia<\/a>, production companies VaynerWatt and Eva Nosidam, media publisher Gallery Media Group, marketing agencies Tamara Group and ChukMedia, corporate barter and trading company Tingley Lane Trading, thought leadership platform Marketing for the Now, VeeFriends, VeeCon, as well as a speaking agency, a sports agency, a food and hospitality group, original content, and\u2026well, more.<\/p>\n And if he didn\u2019t do these things? \u201cI\u2019d be burned out,\u201d Vaynerchuk says, \u201cbecause I wouldn\u2019t be happy enough.\u201d<\/p>\n If you feel the same, then he wants to show you a path forward.<\/p>\n Image Credit: Nigel Parry<\/em><\/p>\n I am sharing Vaynerchuk\u2019s philosophy here because I think he\u2019s right. But also because I\u2019ve struggled with this question too.<\/p>\n I job-hopped my way through my career \u2014 because I\u2019d get bored and miserable after about two years of working anywhere. I\u2019m too curious. I crave newness. The same would have been true at Entrepreneur<\/em>, where I\u2019ve been the editor in chief for 10 years\u2026except that here, I learned how to transform myself into an entrepreneur. While running this magazine, I now juggle many outside projects: I start companies, join advisory boards, and make my own media. Every day is different.<\/p>\n A few years ago, I met a billionaire who wanted to mentor me. We began having monthly calls. But every time we talked, the billionaire would press me on the same point: You\u2019re doing too much<\/em>, the billionaire would say. Pick one thing and focus. Make a list of all the things you\u2019ll stop doing.<\/em><\/p>\n This tore at me. Here was a wildly successful person, known and admired by many, and he was showing me his pathway to success. But deep in my gut, what he said felt wrong for me. I didn\u2019t want<\/em> to pick one thing. It felt limiting and stifling. So instead, I stopped scheduling calls with the billionaire.<\/p>\n It\u2019s been a few years now. I still wonder if that was a mistake.<\/p>\n Then, a few months ago, Vaynerchuk called me and suggested this article. He said he wanted to talk about being a \u201cjuggler\u201d \u2014 because that\u2019s what he thinks of himself as, and he wants to give others permission to do the same. And he knew I\u2019d relate. We first met in 2009, just as he was launching VaynerMedia and I was entering national magazines, and our careers grew in parallel frenetic ways.<\/p>\n So I arrived at Vaynerchuk\u2019s office \u2014 the one his fans are familiar with, with the shelves full of sports and pop-culture paraphernalia, which serves as the backdrop for so much of his social content. And as we talked about this, he predicted that, five years from now, someone who read this article will approach him about it.<\/p>\n He narrates the future conversation:<\/p>\n \u201cGary,\u201d they\u2019ll say. \u201cI read your Entrepreneur<\/em> article five years ago, I listened, and now I actually make less money.\u201d<\/p>\n \u201cOh?\u201d Vaynerchuk will reply.<\/p>\n \u201cYeah. I used to make $530,000 as a lawyer. Now I\u2019m a lawyer and I own a beer garden, and I make $330,000.\u201d<\/p>\n \u201cBut are you happier?\u201d Vaynerchuk asks the imaginary person.<\/p>\n He feels sure the answer will be yes.<\/p>\n This feels orienting to me. Because it cuts to the heart of a question that every entrepreneur must ask themselves: What do I want from my work?<\/em> Your answer is what you should optimize for.<\/p>\n Vaynerchuk knows his answer: \u201cI\u2019m doing all of this for myself,\u201d he says. \u201cI want to see how good of an entrepreneur I am.\u201d His goal isn\u2019t to build one specific company. His goal is just to build<\/em>. It is to take that specific action, and embrace that challenge, and live life as a builder, because that is his core. And that means one company will never do.<\/p>\n This made me think of the billionaire who mentored me. What is that man\u2019s goal? Well, he\u2019d told me: His goal is to build companies toward massive exits. He measures his success by the creation of extreme wealth. And if that\u2019s the case, then of course<\/em> he wants to focus on one thing! He pours everything into one company, because that\u2019s his pathway to selling it. He\u2019s done it many times.<\/p>\n But me? And maybe you? Money is not what drives me. And that\u2019s why the billionaire and I didn\u2019t understand each other. Yes, I like making money, but I don\u2019t need mountains of it. I primarily want to live a life of my own choosing, free from the demands and restrictions of bosses and corporate life. I want full autonomy of my time. I want to explore unexpected paths, and to push the boundaries of my talents and usefulness.<\/p>\n So I ask Vaynerchuk: How do you do it? How do you become a juggler?<\/em><\/p>\n Image Credit: Nigel Parry<\/em><\/p>\n Vaynerchuk stands up. He plants both feet on the ground, next to each other. Then he takes a half-step to the right.<\/p>\n This is the visual he wants you to consider. Your weight was fully planted in one place. Now you\u2019re shifting that weight \u2014 potentially destabilizing where you started, while also needing to build a solid foundation for your other foot to land on. Before you step, you must do an audit on yourself. Ask: What are you excellent at, and what excellence do you need from others?<\/p>\n Start with yourself. Vaynerchuk remembers when everyone doubted his ability to start VaynerMedia. He was just a guy making YouTube videos out of his parents\u2019 wine store, and then he launched an advertising agency. It seemed unserious at the time. Today it operates as the flagship of a diverse portfolio of brands under parent holding company\u00a0VaynerX, a nearly\u00a0$400 million business. So how did he do that? And how, today, can he start a production company that\u2019s creating content for Amazon Prime and the History Channel? And how can he sell eight figures\u2019 worth of assets through VeeFriends? And how can he open a members-only club, Flyfish Club, in Manhattan?<\/p>\n The answer to these questions is the same: \u201cBecause we\u2019re good at marketing,\u201d he says. \u201cIf I start a doughnut shop or a nuclear power plant or a SaaS business, my competitive advantage is the ability\u00a0to outmarket anyone and everyone in every sector.\u201d<\/p>\n That\u2019s it. One skill, transferable across industries. He can drive viewers to the TV show, drive excitement to VeeFriends, and drive members to a club. The guy just knows how to market. And in this way, a seemingly incoherent collection of businesses has an internal logic. It is tied together by a core discipline.<\/p>\n \u201cAnd other people have disciplines too,\u201d he says. Maybe you\u2019re great at finances, or team building, or partnerships, or sales. \u201cSomeone could be a great operator \u2014 and they could go into a private equity firm, or a flyer shop, and either way they could look at the P&L and say, \u2018God, they\u2019re wasting $2 million a year.\u2019\u201d<\/p>\n Whatever it is, you must know this about yourself. Recognize what your transferable value is. Because in this way, every new thing you do is just a new expression of your core skill set.\u00a0<\/p>\n Next, let\u2019s look at what other people in your orbit are excellent at \u2014 because if you\u2019re going to divide your time and energy, other people will need to rise in your place. \u201cIt requires humility to let people shine outside of you, even if you are the reason they are shining,\u201d Vaynerchuk says.<\/p>\n At the highest levels, Vaynerchuk has always leaned on people he trusts deeply. He\u2019s built VaynerMedia and VaynerSports with his brother, AJ. He built VaynerSpeakers with Zach Nadler, who was his speaking agent at CAA for six years. He built Wine Library with Brandon Warnke, his best friend since age 14. These are relationships he never has to question.<\/p>\n Then you must get comfortable with not<\/em> being the person who does everything. That\u2019s a hard adjustment for entrepreneurs, especially if you\u2019ve been laser-focused on one thing for a long time. We come to believe that we are integral to our companies\u2019 success \u2014 as if everything must be done by us or else it won\u2019t get done right.<\/p>\n But Vaynerchuk has some tough news for you: \u201cMost things don\u2019t matter,\u201d he says. Not only do entrepreneurs inflate their own sense of value, but they also inflate the importance of the things they\u2019re devoting their time to \u2014 which means you\u2019re often putting valuable time into things that just don\u2019t require it. \u201cThere\u2019s 15 people in your company that can do it,\u201d Vaynerchuk says, \u201cand most people\u2019s B\u2019s and C\u2019s are actually better than your A\u2019s, because the overall impact on this thing isn\u2019t big enough.\u201d<\/p>\n Whenever there\u2019s a new initiative, Vaynerchuk likes to operate with what he calls the 15-80-5 rule: \u201cI need to be involved in the 15% up front, to really synthesize the idea,\u201d he says. \u201cI\u2019m the offensive coordinator. Then my direct report and their team go away and do 80% of it. And then I get involved in the last 5% to put a cherry on the sundae, and we move on.\u201d<\/p>\n He pulls up his calendar to show me what this looks like. We\u2019re staring at Google Calendar on his monitor, and it is a dense, color-coded wall of appointments. Most of them are just 15 minutes long, which he says is plenty of time to make important decisions. \u201cHourlong meetings are just 15 minutes of meat anyway,\u201d he says.<\/p>\n Once you start structuring your days like this and empowering your team to operate without you, something tremendous happens: You create more optionality for your top performers, because you now have more opportunities for them to pursue. He offers an example: One of his employees has been at VaynerMedia for nine years. She\u2019s a superstar, but was somewhat frozen in place because the person above her wasn\u2019t leaving. This is often why companies lose great talent; there\u2019s just no more room for advancement. But in this case, the VaynerMedia employee was just able to shift to a more senior executive role at another one of his companies.<\/p>\n \u201cSo not only does this create optionality for me,\u201d he says, \u201cbut it creates optionality for everyone.\u201d Because Vaynerchuk knows: He isn\u2019t the only guy at his company who wants to do more. By thinking so ambitiously, he\u2019s attracting and retaining exactly that kind of person.<\/p>\n
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