Gary Vaynerchuk Curated
Chairman of VaynerX, CEO of VaynerMedia
CURATED BY : +44 others
What is your one piece of advice to anyone that wants to start Crushing It?
Buy into positivity versus negativity. Blindly buy into positivity. Positivity leads to offense and results. It's the macro of it all. I think it's a black and white game. You're either positive or you're not.
What are some of the main mental inhibitors that are holding people back from creating their voice?
Believing that somebody else's point of view is greater than theirs. The insecurity that their parents established and not breaking out of it by surrounding themselves with optimism and positivity. The lack of self-awareness, and blindly believing they can do something out of sheer wishing it. And delusion, instead of truth.
What are some of the starting points for introverts who want to build their brand?
By recognizing that to be out there, you have to produce output. Whether it's written word, audio or video, you've got to pick one. If you're an introvert, written word and audio tend to be the stronger place to go. But you can't be heard if you're not communicating. I also think being a number two or being the back office is always a worthwhile opportunity. The problem is you can't go from there to being a puppet master. When people listen to me say this, their intuition is, "I'm gonna get somebody charismatic and I'm gonna be the brains behind that." That tends not to work. I think you need to realize that you won't be the partner of, you'll just be the employee of.
In your new book you say, "Some things don't change between brands and human interaction." You also talk about what still matters. So, what is it that still matters?
Ultimately, a value exchange matters the most. No matter what, if you bring somebody value, if you make somebody laugh, if you make somebody think, if you deliver on your promise, that is always going to work out, no matter how you do that.
What is the current state of entrepreneurship? And how will the next generation of startups be impacted by it?
The current state is that it's never been more popular. It's never been cooler. It's never been more of a rock star culture and there will be a lot of impact on the next generation. When the economy crashes, will entrepreneurship be looked down on as something that was high risk all along, and does the culture change and go the other way? My belief is yes. I think there will be a cleansing. Entrepreneurship will always ride in waves. Where I grew up entrepreneurship wasn't cool, or something you aspired to do, it was all about school. Entrepreneurship is going to continue to grow in momentum. But eventually, it will get corrected. It's not for everybody. The next generation's getting very affected by this right now because it's currently a status symbol, and that takes years to get out of the system. In the next 10 to 15 years, even with a crash, there are too many people who have already been affected by the romance of entrepreneurship that will continue to play the game.
Stephen Hawking passed away recently. There’s been lots of different soundbites about what he’s said about AI i.e. a super intelligence that could spell the end of the human race. But ultimately what he was really saying was that we need to understand this technology and potentially regulate it. Are you of a similar mindset?
That’s a great question. I genuinely believe that we are naive if we don’t believe that this accelerates to a level that is far beyond our minds. Look at what the sci-fi movies of the 60’s predicted. There are certain things we’re not even close to, but there are also technologies that are far exceeding our dreams. You know it’s funny, I’m a boy that was born in the soviet union and grew up in the US, so I have a very interesting dichotomy on regulation and a free market. I’m a big believer in the human spirit. I think the most underestimated thing in the world is human. We’ve been around forever and we’ve gone through unbelievable amounts of things. My question is: look, would I regulate AI today? I intuitively wouldn’t. I believe that would lead to not getting to the opportunity fast enough
Technology's changing us as well, surely?
It’s exposing us, not changing us. We are using these tools and we are big boys and girls. Facebook does very little in comparison to what Network Television does. People have been curated to their whole lives. We make choices everyday. I think there is an enormous lack of responsibility. We have an unbelievable inability to take responsibility for our actions and it feels a hell of a lot better to blame technology than it is to blame ourselves for short comings and ignorance.
Are we in an era of predictive retail and over personalization?
Yes, I believe there’s an opportunity for that. But I’d also argue that then comes the new business and media and marketing opportunity. Like Snapchat in the face of an open, social web. So, the answer’s yes. And then, what’s gonna happen is there’s gonna be this huge opportunity to move back into broadcast, because we’re going to be starving for the opposite. That’s the human psychology. Technology is exposing us, not changing us.
there is certainly a need for inclusion during the development of AI because it’s so important to get it right.
Are you kidding me? There’s a need for inclusion in every aspect of our lives in both directions. I live in Manhattan, I spend time in Silicon Valley, I have an office in London, LA and in Chattanooga, Tennessee. I don’t think voice, as big a technology space as it is, is the biggest thing we need to address. The human race has things that it needs to look at itself for. I agree voice is going to be a massive platform thus it’s an opportunity for us to have great inclusion. I would argue that what these companies are going to do, is they’re gonna allow you set it up from the get. Like, it’s really easy for these four or five tech companies to allow you to set up Alexa the way you want. Everyone will have complete control over that voice's sound and tone.
In terms of the conversations that could happen within that device, if the predominant group creating AI do not reflect society, what happens then?
If you’re in the trenches and you understand the people working on these platforms, look, technology’s heavy handedness and the conversation around it is an interesting one for me because it’s actually very simple: everybody here is a big boy and big girl. If you’re unhappy with Amazon or Google or Apple’s execution around their imposing way, you’re more than welcome to not use them anymore. All my friends who are deeply conservative who tell me "screw Google because the results that come up have liberal bias", I tell them all the time, you’re more than welcome to use Yahoo.
Let’s talk about some of the risk involved. It wouldn’t be technology and there wouldn’t be opportunity without some risks. One of the biggest potential risks of AI, is actually the risk of bias and negative bias. For example, many voice assistants typically have female voices unless you change the settings.
I think it’s an interesting question. I’m a big fan of intent and also understanding consumer control. So for example, I have a lot of empathy for Google and Amazon, they have to pick one of the voices or they just mash it up to create a neutral voice that doesn’t exist that sounds like a robot, which I don’t think is going to be the best use of their time. If you’re Apple and you’re coming out with your voice, you’re Siri, in essence you’re picking between a man or a woman, right? And in this highly emotional political state you have people react one way or the other. I think for me, what Vayner media is doing about it is, we’re having some interesting conversations like we think brands are actually going to have to have a voice. Like, what does Budweiser sound like? These are conversations we’ve never had before in our lives. Is that Morgan Freeman everytime? Is that a new voice altogether? I recognize that we need to be thoughtful at all times, when you only have an A or B choice, you’ve gotta make a choice.
So if a brand is going to develop Voice AI should it work across different platforms?
Yes, absolutely. I’m already trying to figure out how to work on Google Home Pod, without knowing anything. I’m giving my recommendations because you don’t want to be at the mercy of one, let alone two. Plus you never know who wins, right? Like, I intuitively feel like Amazon has got a real shot here. It’s really hard to completely count out Google and Apple and I still think sneakily in some weird place Facebook is working on something.
There are some who think it’s a mistake to put your brand in the hands of a third party, letting the likes of Amazon or Apple speak for your company. How do you still maintain a voice (pardon the pun!) as a brand using Voice AI?
I mean, what’s the alternative, right? Let’s talk about the number of businesses that are not leveraging Google or Facebook or TV. That’s just the game. If you wanna build a brand and build awareness you are going to rent space at some point. Driving them to your environment and collecting first party data is the game, right? I think it’s a mistake to rely solely on anything, look at the biggest brands in the world they were relying on Walmart. That was a mistake. They’re going to end up relying on Amazon. That’s going to be a mistake. So I think it’s a dance and the way you win that dance, and they way I have as a personal brand, and the businesses I’ve helped who’ve won, is by only thinking about the end consumer.
So in the context of brands using Voice AI, how can they compete in this space? Will platforms ultimately decide what content users encounter?. Are there ways in which brands can maximize or optimize their presence whether that’s voice SEO or paid voice AI? What are the type of things that brands should be thinking about?
I think ultimately we’re going to get into an environment where there are apps built on top of these devices and brands and businesses and entrepreneurs need to try to become the voice versions of WAZE, Spotify, Instagram and all the other monster businesses that were built on top [of the smartphone]. One could have formed this argument when the iPhone came out, like Apple can control, Apple can make. Ultimately these platforms make a hell of a lot more money if they’re frenemies with the brands. Amazon’s not going to private label every single category quickly. So I’m a big believer that brands need to understand these platforms (whether that’s voice or social) and they need to find the right cadence and the most value out of it, while recognizing that they’re not fully in control.
Let’s talk about control for a second. That dynamic between the user, the brands and the platforms (the machines/the device). Who’s actually in control here?
The software’s in control and then the device that delivers it. I mean, we have to go a little further in that question, the consumer is in control of everything because if you don’t choose to have that device you don’t have it. But once you enter that fray, the relationship changes and then the device starts the process of taking over.
Can we establish your views on how revolutionary Voice AI is and is going to be in our day to day lives
It’s going to be one of the core pillars of our interaction. I would say in a decade it’s going to rival the cell phone as we know it today. Ultimately because of how much time we spend the cell phone will continue to be the primary, but I genuinely believe that voice AI enabled devices and infrastructure is going to become as crucial as the cell phone in the way we interact with technology.
How to Find Fulfilling Work?
Find a job or build a business based on whatever you like to do when you aren’t working. If you don’t know what you like, try different things. Test out everything from operations to sales. Travel and take hula-dancing and pizza-making classes. Putting yourself in a position to do that might mean working a side hustle after your nine-to-five job. Email people asking for a month-long internship to learn from them for free. Try as many things as possible, because you won’t get anywhere by guessing.
What are you most proud of?
A lot of things in my personal life, but in the genre of what we’re talking about, I think there’s a lot of entrepreneurs winning, by definition of entrepreneurship, which is making money. I’m most proud that I spent an ungodly amount of time putting out free content, had no interest in monetizing my audience like a lot of other people and get hundreds of emails a week and DMs of, “You’ve made my life better by either mindset or positivity for tactically showing me how to grow my Instagram, or sell stuff on eBay.”
When you were on the Breakfast Club last year, you said something that really caught my attention. You said, “Hip-hop is the scene that rules the world.” Can you elaborate on that?
I think if you’re 14 to 30 in America, hip-hop, for a majority of people or for the people that end up really driving trends and culture, is a foundational part of their lives. A lot of the things that happened in the ’70s and ’80s and ’90s were driven on the foundation of rock and roll, and a lot of things that are happening in the 2010s and soon to be ’20s and ’30s, have a foundation in the majority of hip-hop. You’ve got kids, women, and men, who grew up influenced by urban hip-hop culture, who are now in their 40s and 50s and making decisions for the world. That plays out and there’s a level of authenticity and lack of fronting and creativeness and the grind and hustle.
Say a bit about your relationship with hip-hop culture because I see you hanging out with rappers all the time. Where’s the overflow there? If you aren’t really keeping up with what’s cool, how are you in the know?
Growing up in Edison in the ’80s, I went heavy with Beastie Boys and Bone Thugs-N-Harmony, and then I went to Mount Ida College which was an extremely urban environment where I really got deep into hip-hop culture. Then I went into the wine business and was really removed from it. In 2009 when I started Vayner Media, my brother’s dear friend from college Mike Boyd came over, and they graduated and we stated a blog together, because I was so interested in the music and the scene but I was so busy. So we started something called Hip Hop At Lunch in 2009, and its thesis was to cover emerging artists, because I was obsessed with unsigned hype in The Source when I was a kid. Just fascinated by ‘who’s next?’ So we wrote about (rest in peace) Mac Miller and Nipsey Hussle and Wiz Khalifa and Nicki Minaj, all when these people had less than 10,000 followers, they literally were in our office. It was crazy in hindsight. Hip-hop and entrepreneurs are the same. We hustle… It’s authentically integrated, feels natural, and right now it’s a really interesting rotation. It’s in this place right now where it’s a thing and everybody’s getting value out of it, which is nice.
How would you describe your personal style?
Casual, unbelievably insular. I’d describe it meaning ‘not wildly affected by what’s cool.’ I’m just so busy that my style is a byproduct of how busy I am, meaning I just don’t have enough time to really pay attention to what’s happening with other people’s clothes. Of course I live in society, when I see somebody rocking something fresh or… I can pick up on a couple of years ago, “Oh I guess girls are not wearing jeans with cut-outs in them.” Or “why is Fear of God really capturing everyone’s attention?” So I’m not delirious, but I’m unbelievably insular and wear whatever the fuck I want when I want, how I want. But unbelievably casual, like jeans and T-shirt to the death.
Tell me a bit about your new sneaker.
So the latest sneaker continues from the last one, “003 Clouds & Dirt.” It’s my macro thesis on entrepreneurship which is high/low, macro/micro, have ambitions, know your ultimate strategy. Why are you doing things? What’s the business’s strategy? What’s your life strategy? But then have the humility to live in the dirt. Don’t just be an ivory tower pontificator. Don’t just have sizzle, have steak. There’s only 5,000 pairs made, we’re going to launch at ComplexCon and I’m really excited about it. People that have been watching my blog carefully and have picked up on it and zoomed on it are also also excited about it.
Okay, so how did you become a sneaker designer? When did this get into the mix?
You know, I’m living life, doing my entrepreneurial thing, I get a cold email on my website that says, “I’m the president of K-Swiss.” Which caught my attention because I’m 42 years old and I lived through the era where K-Swiss were the YEEZYs and the Nikes of the time. At first I kind of assumed that it would be like an influencer marketing thing, which I’ve never done. I’ve never done a post for pay but it just had an interesting tone to it, so I decided to have a coffee. Sure enough, Barney at K-Swiss, the president, he was talking about my signature on the sneaker like it’s a real thing and obviously caught my attention. It allowed the little me – ’80s baby Jersey kid – to dream a little dream and, to be very frank, my macro business strategy is that nostalgia’s under priced and that nostalgia brands are a real opportunity. Very much in my mind it played out as, “Okay, I could work out my pieces here and see if I can help resurrect K-Swiss into culture. Can we make it more relevant?” I definitely believe, whether it’s me or somebody else, that anybody who’s paying attention to the culture, to society, understands that entrepreneurship (at least, at this moment) is on a pedestal culturally and much like an athlete, or a musician, right now there is a level of street cred, coolness, sizzle that goes along with being an entrepreneur. And so to me it wasn’t a foreign idea that an entrepreneur could carry a sneaker just like a fashion designer or a rapper, or an artist. So I thought it was a worthwhile swing.
I see so many words thrown around the web to describe you – social media mogul, entrepreneur, internet personality… What words would you use to describe yourself?
That’s a good question. I think entrepreneur really captures it for me, and I’ve been one from the beginning. At the end of the day, ‘passionate entrepreneur’ sums it up really well. Or a lot of times I say ‘purebred entrepreneur,’ because I like the losing as much as the winning, and to me a purebred loves the process over the fancy things that come along with it when you’re in the 1% that are good at it. So yeah, that’s how I think about myself.
How does social media change marketing today?
It’s the new world we live in. On Twitter, the number one thing that people were talking about during the Masters on Sunday was Tiger chewing gum. So, let’s say we have a gum client. I call them — this is Sunday now, because we’ve got to move fast. I want to know what gum he’s chewing and jump on this. Nobody watches commercials any more. Nobody goes through direct mail carefully. Nobody is going to page 37 of a magazine looking at the ad carefully — the world has changed … I’m sorry. Farming used to be our number one industry. Sears was the number one retailer. Walter Cronkite was America’s dad. Things change quicker than ever.
Is there any room for mass media any more?
Occasionally. The Super Bowl is amazing. Product integration is key. If you’re a top 10 bank or top 10 in your category, instead of spending $50 million on television commercials that nobody sees, I’d rather give a big-time production company $10 million to be the sponsor of a new show on Netflix called “ATM”, where the whole show transpires around ATMs and it is literally your company. The Ed Sullivan Show was funded and created by the Lincoln Town Car Company. People forget that historically television started with brands funding it. Commercials came later. I believe now that commercials are going to be disappearing because we’re streaming — traditional ads are a tough buy. But I do believe that Netflix and Hulu and Amazon will test commercials. My intuition is if they’re smart, they’re going to do product integration. I’ve always thought that a big truck company should do a show called ‘The Tailgate’, where the whole show again is at a tailgate. And it’s your truck as the family’s truck. It’s about product integration.
Is the banking industry too transaction-oriented?
The industry is disproportionately short-term transactional, and that creates some short-term benefits, but retention is going to be an issue. I think the products and services that most banks and credit unions are providing, versus the alternative products and services that are emerging from digital-first competitors, is something that’s going to cause a lot of friction in the future.
Should organizations give their employees the right to pursue self-development?
Any great company will allow its players to be put in the best position to succeed. And, if you are fortunate enough to have innovative thinkers, people that are on the offense who are not delusional, that is a bonus. I think one of things that I’m passionate about is for all my sizzle, and all my new thoughts, I’m grounded in business practicality. I noticed a lot of people that follow me come and pitch these wild ideas in their company that are not going to happen. They’re like, “Hey bank, let’s do VR”. And I think that’s cool. And so I think companies need to allow their thinkers to think, but thinkers or innovators or people in the offense in these companies need to understand if they’re lucky enough to be in an organization that gives them some freedom, they can’t come with, “Let’s do a ‘Pokemon Go’-like thing in VR for our bank,” because that doesn’t make any sense. Everything I mentioned today about social media marketing will work today — it will work to run thoughtful Facebook ads that tell people why your branch is a better branch than the one down the street. Or, running a piece of LinkedIn content on tax day like: “Have you thought about these six unknown ideas to save on taxes?” This builds an affinity that says, ‘Who is this company that just helped me? Is this something I could consider?’ Value is what’s important and not being a technologist or a futurist or being innovative for the sake of being innovative. Delusion is a very scary place where a lot of people go when they are given a little too much freedom.
Is Amazon the biggest threat to banking?
100 Percent. They have the consumer. In fact, Amazon, Apple and Netflix have the consumer. Even Spotify. They also have data. They have lots of access to insights. But Amazon most because it has permission. They provide free shipping and you’re saving a fortune. Plus, Amazon is also giving you the Prime content for free. You get the competitor to Netflix, Hulu, Disney along with that package. That’s been one of their bigger challenges … to make sure everybody in America knows that they have the Prime subscription when they have a Prime account. Listen, unless the government gets involved or unless Bezos jumps off of being CEO, Amazon will continue to innovate and continue to be successful because it is so consumer-centric.
How about for an industry that isn’t feeling pain right now?
The height of the black-car taxi industry was the year before Uber was invented. Great prosperity is usually the early indicator for turmoil.
What is key message you want financial marketers to hear?
Marketers can’t hold the past on a pedestal. To me, there’s a lack of common sense and a disproportionate lack of consumer-centric DNA. There’s a lot going on right now in modern marketing that keeps me baffled, and I want to continue to put pressure on it. First, selfishly, because I think I’ll be historically correct, and because it feels amazing when you run into somebody who says “Hey, I listened to your message and good things are happening”. That feels remarkable impacting people’s lives or companies. It’s an incredible high, and having admiration is an incredible ambition of mine, and so it feels good.
Yik Yak used to be 400 million $. It sold for 4 million $. Thoughts?
Correct. But I don't feel bad, because that's entrepreneurship That's business. I think a lot of people are getting confused right now about what success actually looks like. Only a very few will break through and actually sell their business, actually go public, actually make it.
Youtube is where I think a lot people assume that your career started but you were working behind the scenes for 10 years building up this internet business. Thoughts?
The thing I'm most proud of is that when people try to take a razz at me as a self-promoter - and I'm very empathetic to that, because I do so much around my personal brand - but if they even spend four seconds digging, they'll realize I didn't say a word until I was in my mid-30s and had already built an enormously large business. Not by tech standards, but I had no cash infusion. A 10% gross-profit liquor store in the mid-90s - to grow to that scale was very hard. VaynerMedia's been fun for me. I would tell you secretly, and I haven't said this a lot - I'm trying to give you a nugget for your podcast. I needed to build VaynerMedia up for myself because I was starting to become Gary V, to your point. The wine videos put me on the map. I wrote a book in 2009 called "Crush It," which gets me into the "You're a motivational speaker" or "You're a pundit." It started becoming about my personality and me on Twitter, more than my business accomplishments, so I needed Vayner. I need to build an agency against the biggest firms on Madison Avenue, and I needed this big success even to just remind myself that I'm an entrepreneur, an operator, an actual businessman first. I'm not what I think there's a lot of right now, which is a lot of people running around and saying they're an entrepreneur on Instagram. I'm proud of that. I look at something that is upsetting to me. When I see Yik Yak sell for $4 million, I feel bad for the guys.
You started a website for the business at a really unusual time. How did you know to do that?
I went on the internet in '94 and in four seconds landed on a AOL bulletin board where people sold baseball cards, and I just knew. The same way that I knew that Twitter would be big and that's why I invested. Or Tumblr or Facebook or Uber. I've done Snapchat. I've done really well on one core principle which is, I think I have an intuitive ability to understand consumer behavior more than the average bear, and I'm not scared to bet the farm on that gut feeling. Even online dating. I met my wife on JDate in 2003.I just remember thinking in 10 years, every single person - I didn't think they'd be swiping to the right - but I'm like every person's going to do this because this is practical. People are romantic. People are like, "I'll never buy a tomato on the internet." This is what I heard in 1996. I'm like, "Yeah you will. Because time is valuable, because other things matter more." I knew because I thought people would buy stuff on the internet long before a lot of people thought that.
You worked in the liquor store. At 14 can you even be in a liquor store?
Yeah, because nobody was really checking. At 16 you can get a permit but I was in there at 14. That's probably why they put me in the basement bagging ice and stocking shelves. Somewhere around 16 or 17, I realized people collected wine, and that caught my attention because I was deep into baseball cards and comic books. I really enjoyed learning the wine world and really became fascinated by it. That all manifested a couple years later to me launching, in 1996, a site called WineLibrary.com. We rebranded the store to Wine Library and that started my first chapter. We grew the business from $3 million to $4 million a year initially, to $45 million then $60 million a year in a very short period of time.Having a website 21 years ago for a single-store wine shop, liquor shop, in New Jersey was like having a VR studio in a flower shop right now Iowa.
Like you said, your dad came here when he was 22 and he built up a wine-and-liquor shop. From what I read, you all shared a studio in Queens. There were eight of you in a studio. Packed house. Right?
Packed house. My dad first was a stock boy and then was a manager. An amazing piece of advice for a lot of kids, 50-year-olds, whoever is listening right now: Saving money is a good strategy. I didn't have stuff, but it was because my parents were saving. They were saving. We didn't get toys. They told us to go outside and paint a rock.It was very, very smart because after seven or eight years, he was able to buy a liquor store of his own in Springfield, New Jersey - Shoppers Discount Liquors. He built up a great business. A $3 million- to $4 million-a-year business. He made it, right? Literally made it. Middle class, upper-middle class, and made it. We didn't ever need anything. They didn't spend a lot. They're big savers but we made it and then I got dragged into it at 14. I'm the oldest son; I'm one of three.
You were doing all those things that kids try to do when they're entrepreneurial-minded. You had a series of lemonade stands, right? A franchise almost.
I didn't know it was a franchise when I was 6. I've always had a knack for branding, so even with the lemonade stands, it was "Gary's Lemonade Stand." I worked on the signs all day, more so than on the lemonade itself. Then I learned you had to make good lemonade to build an actual business, so that taught me about lifetime value and quality. I learned a lot as a kid. I was a very poor student, which was really unusual for immigrants, but I didn't see education as my way out. It originally started as, I'm a good salesman, and then it was, I'm a good businessman, and then it was, I'm a good operator. Now the current term is I'm a good entrepreneur. It's a DNA thing with me.
I want to go back to your childhood. A lot of people might think you were born into success, but your beginnings were pretty humble. What do you have to say about it?
You know, it's funny, I actually think my kids are going to have a harder time being successful than I was. I think being born in Belarus, coming here with nothing, my parents working every minute - that instilled a huge competitive advantage, a chip on my shoulder, a work ethic. Immigrants win a lot and they win a lot because of a couple core things.I didn't start with a lot. I have friends who started with a lot who have now built on top of it, and I'm impressed because I used to think that was a disadvantage. I think there are a million ways to do it. I like my dad's narrative the best. He was 22 when he came to America, had nothing, so that's a really amazing story. I'll take mine. Baseball cards, lemonade.
Gary, again, thank you so much – this interview has been everything I’d hoped it be and more! It’s been a pleasure chatting with you.
Wish you well! Goodbye.
So breaking those down, they’d could be summarized as find what’s working and go all-in to take full advantage of it and don’t let personal relationships trump your business judgement.
And listen, that’s only putting my business hat on. I’m glad I supported those good human beings at Viddler but it definitely cost me. No doubt.
That’s great…. Gary I know we’re getting close to how much time we have allotted for this interview so I want to end with one last question. When you were building up Wine Library what are a few of the big mistakes that you made over the course of taking that wine business from a bricks-and-mortar store into a full-scale eCommerce business that looking back you’d do differently – and also that you could warn entrepreneurs against making those same mistakes?
If you’re successful and you have some early success like I did – even though I’ve always been very confident in myself I don’t think that I went all-in in two separate times. One was SEM (search engine marketing) – when Google AdWords came out – it was really working for me but I should have gone way more all in and I let the market catch up. I had three or four years where I could have been the SEM (ie PPC) leader and it was inexpensive and I just didn’t do the right thing there. The big data stuff, I didn’t win on that. And then the other mistake I think I really made was even though I knew YouTube was going to be much bigger than Viddler, I made WineLibrary TV live on Viddler because I just liked the founders and in hindsight not betting on YouTube and not amassing all those views and building up channels has been a mistake. I knew it at the time and I let my emotion for loving human beings trump what my business savvy was telling me and I don’t know if I necessarily view that as a mistake, but at some level I do.
Can your wife stay awake through the documentaries? Mine can’t, she usually totally passes out.
She’s pretty good – Lizzie can get into it. I love storytelling and I think that documentaries are so raw and real. The Bo Jackson 30 for 30 ESPN documentary was just riveting stuff for me.
Tying in a little bit to the personal side, everyone knows that someday you’re going to be the owner of the New York Jets. Everyone knows that you’re a huge advocate of social media. And everyone knows that you’re always in this just unbelievably fantastic mood – nobody’s quite sure how – but these are all parts of your persona. But what’s one thing that doesn’t get talked about a lot that you love to do or that you’re passionate about that people don’t know about?
That’s a great question for this series. You know it’s funny, I’m a fairly outrageously open book, ya know? I would say…. You know what? I’ll give you a good one. I’m in love with documentaries. I love documentary movies. If I don’t want to be working – or if we’re going out and Lizzie is taking two hours to get ready – if I can sneak in a documentary. I love the 30 for 30 Series that ESPN is doing. Or serious topics – I’ll go to on-demand TV documentaries and that’s the way I enjoy to consume content. And so, that’s something I don’t think I’ve said much ever – trying to give you a little nugget for this interview. I’d say I’m a big documentary buff.
When you say social growth, do you mean actual interacting with friends and peers or do you mean professional networking?
Yeah, I mean leaving your parents house for the first time, I mean friends, I mean you’re going to miss going to parties and hooking up with guys and girls and drinking beer and all those life events so that’s going to make you act out at 25, 30, 35 and that will have an impact on your life. So we’re looking at it from one equation. Do I think that financially and business wise you’ll be more successful? I do. But that’s not just what life’s all about. And so you’ve got to think about how to subsidize some of those social things. And so maybe you go to Spring Break with a couple of buddies each year – be smart about how you do that.
So I guess I don’t need to finish asking my question! So you would advise someone to forget college, take that money and start you’re own thing.
There’s one thing I would say about college. It creates a lot of opportunity for social growth so if you’re going to do that [skip college] figure out a way to subsidize the social growth that at that age really brings a lot of value.
For an ambitious 18-year old with $50,000 in the bank and he’s interested in owning his own business someday – I know you went to college – but in today’s with all the educational issues and student debt issues….
By the way, I would have never gone to college if I could have convinced by parents otherwise. I thought it was a four year waste and I would have been four years further along. I feel like I’m 37 right now and I feel like I’d be at the same place at 33 [if I hadn’t had gone to college]. I really do.
So don’t try to compete on Amazon’s own level of efficiency and price. Really, the only way you’re going to win in the long run is…..
It’s like sports, right? Like boxing or football. You can’t let them play their game, right? You hear that all the time.
In terms of Wine Library and the things you’ve done, are those the strategies you are taking there – obviously you’re a niche wine reseller….
Yeah, absolutely. And I think we’re bigger so we’re even more vulnerable. I would say that if we were smaller and only selling Pinot Grigio, we’d be fine. Does that make sense? But because we’re more broad and a leader we’re definitely going to feel the heat but if we continue to do things we’re doing like calling everybody who places an order for the first time and really giving personal recommendations…. I mean, the only way we win is by out-humanizing and out-friending them.
Absolutely.Amazon is something I’d love to hear your opinion on. They intimidate a ton of eCommerce merchants, especially the smaller guys without the scale and the pricing power and shipping options. And so looking forward three to five years, how do you think their role will play out in the eCommerce ecosystem? Do you see them being successful in overtaking most smaller, niche merchants or do you think their huge size and obsession with growth will ultimately end up hurting them?
No, I think they’re going to win and I think they’re going to eat up a lot of the small stuff. But they’re going to eat it up as being the platform meaning a lot of small guys are going to thrive selling through Amazon as a platform more so than Amazon [itself] will sell everything on the planet. Amazon is also very vulnerable to small guys. The people that should be scared of Amazon are the medium and big guys, not small guys. Small guys can scale effort where Amazon can’t. You can win on customer service, and really trying, and really caring, and all the things that Amazon will never be able to do like calling every single one of your customers that bought something, hand-written notes, just the humanization – that’s where small business can win and that’s where you need to play. You need to David and Goliath them – you need to win with little rocks.
So how can someone who’s thinking about starting an online store, how do they know what gut questions they need to really ask themselves and be honest with themselves to determine if it’s actually something they can pull of – or if they’re just going to waste a lot of time and they’re better off suited to a traditional 9-to-5 job?
Let’s get real practical. If they’re reading this right now and they have that feeling, they should just do it. Because they’re going to be 70 and regretting that they never just did it. I’d rather that they spend $20,000 to $50,000 and be happy when they are 80 years old than not. Again, I’m letting you know I’m answering this question in a format where the person reading this that has that feeling needs to go and do it. Does that makes sense?
So you think it’s a process that actually can work, or….
No, no I don’t. I think everyone is an individual and if you’re an entrepreneur and you sold lemonade, and sold rocks, and sold blow pops in school you’re going to be able do that, right? Because guys and gals like us – that’s us. I mean, I fell in love naturally with wine – there was nothing better a sixteen year old could fall in love with, right? So I agree with you but there are also a lot of people who don’t roll that way. My Mom can’t roll that way. And so I would tell you that it’s very dangerous to give a one-size-fits all advice – so yes but also no. What really happens is that I don’t think people realize that being an entrepreneur or a business owner is a skill or a talent, much like being a professional golfer or a painter. There’s a funny belief that anybody can do it and I just don’t believe that. I think anybody can have some form of success, but sustainable “this-is-what-I-do-for-my-living” success? No. The only way that I think that that could conceivably happen to people who don’t have that talent is if they love the thing so much that they literally love it to success.
What do you mean by that?
I think the way that you just articulated it is the same way that I could conceivable articulate it, but I believe a lot of people aren’t in love with “selling” the way you just described it.
I talk to lots of people who start online stores around their passion but often end up failing because their value proposition is too weak or the market demand isn’t there. My philosophy is to go after an in-demand niche where you can add value that will give you the best chance of success – maybe not even one you’re interested in at the time. Then as you experience success you can’t help but become passionate about your business and your products and…..
I think that’s the statement of an entrepreneur’s entrepreneur.
So if you do look down the road three, four, five years down the road and anticipate the new “normal” – the new things stores are going to have to be doing to compete effectively, do you think mobile is at the top of that list?
Gary, I love that you were one of the original eCommerce pioneers, building the Wine Library store during a period when Netscape was the de facto browser and people were absolutely terrified of shopping online. Given your experience from the beginning, what’s the #1 piece of advice you have for aspiring entrepreneurs who want to launch their own eCommerce venture today?
I think they need to take the same energy into their eCommerce venture that I did into mine which was people are going to buy this way in [upcoming] years – and that was kind of my thought. So I made the investment 36 months out and not based on what was going on at that moment. And it was really tough to feel that way back then because a lot of people told me they’d never buy something online. People were petrified of putting their credit card numbers into a computer. I would tell aspiring eCommerce entrepreneurs to think the same way which is this: a site came along not too long ago called Woot.com and it changed the way retail was done. All the flash sales and the daily deal sites came from that energy, right? And so I would say one thing I’m thinking a lot about right now is mobile. Who can win [create] the most native, most natural, easiest way to buy something on a mobile device? I think that person has a huge opportunity. That’s the way I believe people are going to be shopping in three years but someone else might be reading this thinking “Hey wait a minute, what about Google glasses? If I can figure out a way that if someone is looking at a shirt [through the glasses] they just press a button on their glasses to buy it…” — and they’re probably right. Don’t take my word. Take your intuition, your research, your ability, your gut feel, your thoughts and apply that to where the market is in 36 months. I think that way too many people are playing in the reality of what it is right now vs. three years from now and I really believe that’s the way to play – three years out.
Do you still recommend that people should quit their jobs unless they truly enjoy them?
That’s the headline, but I never say quit your job unless it is practical. But I am absolutely affected by the 400 trillion to one thing – which is your chance of being born. It’s real to me. I don’t know how people can’t realise they’ve won the ultimate lottery, so why don’t I maximise my happiness while I have my time on Earth?
Have you always had unshakeable self‑confidence?
Yes, my mother did a good job. I talk with a lot of confidence, but pay attention; I don’t talk about a lot of things, I’m very narrow. I was a very poor student, I was not a star athlete, I’m not the best-looking person of all time, I’m not artistically talented… I’m just a really, really good businessman, I am extremely good with people and I understand them. I triple and quadruple down on that to produce all the things I care about in life.
Is that the kind of selling you do?
It looks like that on a surface level, but I think I don’t sell against weaknesses. And I don’t monetise my audience; it would be easy for me to sell marketing courses, ebooks and mastermind courses, but I do not go there. My biggest goal is for my clients to not work with me any more, and for my community to stop watching me, so that they can go out and do their thing. I teach them the tools and the viewpoint and they can go do it themselves.
You’ve talked before about how we’re taught to work on our weaknesses but not bet on our strengths… why is society like that?
Because there is more money to be made selling against people’s weaknesses.
People are scared of change…
It is pretty fascinating. Humans are very good at holding on to the past… it is an enormous fear of change. When most people see something new they think: “How is this going to hurt me?” and when I see something new I think: “How is this going to help me?” That mentality has been a game-changer for me, and every other entrepreneur, because we’re not scared to fail and we’re not scared to put in work. A lot of people talk about fear of change, but it’s really an enormous fear of extra work or of failing.
So technology has always been disrupting democracy?
Social media has been disrupting politics and business; it’s just that the mainstream world hasn’t accepted it yet, the same way it didn’t accept cable or the internet or television…
Social media has got a lot of blame for Brexit, the election of Trump – for spreading fake news, legitimising people with extreme views… is that deserved?
I think yes and no. The blame is insane. Once again, the human race enjoys blaming a platform rather than itself. So I don’t think it’s Facebook or Twitter’s fault for fake news; it’s human beings’ fault for becoming headline readers and not taking a minute to do their homework. A similar thing happened in the 1960 US presidential election. When people watched the debate on television between John F Kennedy and Richard Nixon, Kennedy looked way better, so if you watched it you thought he won, but if you listened to it on the radio you thought that Nixon won.
What do big brands get wrong about social media?
Social media itself is the misconception. Brands think of social media as the smart afterthought – a nice to have, fly-by-night passing thing that they have to appease for AdAge or to make sure they are not out of touch. Social media is just a slang term for the current state of the internet – the websites and apps that people consume on their mobile device. The mobile device is the most important platform in the world: the phone is becoming the television and television is becoming the radio. And Snapchat, Twitter, Instagram and so on are the new CBS, NBS, BBC. When you realise that, then all of a sudden there’s nothing more important.
Your Wine Library video blog was popular, but when did you realise you could turn your experience into a digital agency working for blue-chip clients?
In December 2008, a couple of gentlemen from ESPN Disney invited me to speak with them. I walked out of that office with two things: a $5,000 cheque, which blew my mind, and the reminder that I had something and that I was seeing the world clearer, faster, easier than my contemporaries. So I called my brother, who was graduating, and said: “Why not get into the client services industry? Why don’t we learn how the biggest brands in the world think… why they are doing the things we don’t believe in?” And that was the start of Vayner Media.
Can you take me back to the mid-1990s, when you were working in your father’s wine shop… how did you spot the opportunity to grow it via the internet?
Right now, we look at the micro internet trends – is Snapchat gonna be big? Is VR gonna happen? But back in 1995/6 we were debating the macro internet – ie, whether the internet itself was a thing? When I discovered the internet in 1994, to be frank, I just knew immediately that people would buy stuff on it. It’s not much more complicated than that. I decided I needed to launch a website, but I didn’t know anything about computers, let alone the internet, so for the next two years I learned. In 1996, we launched one of the first e-commerce wine businesses and by 1998-99 I’d realised that email was a very powerful driver for the business.
Planet of the Apps could make you a lot more famous…
I’m definitely going to be known by a lot of people. It’s incredible, this juxtaposition we’re living in now, where you have people who are famous in the traditional sense of print, radio and television, and people who are famous from the online world – and I think they are going to collide very aggressively over the next decade. One of the reasons I want to do things like Planet of the Apps, or speak to you right now for that matter, is that, at the end of the day, it’s just about attention – and I’m not that emotional about where I get that attention.
What will your next book be?
Gopi Diaries is the first of a three-part series. The second part will come out this year and the third is expected in 2021. Gopi is the hero of my book. Now that my son Rohan is married, Gopi will get parents and will also get a girlfriend in the coming series.
Tell us about your book on The Gopi Diaries...
Gopi is a year old. He gives tremendous joy, unconditional love. What I think about Gopi as a dog is normal, but how Gopi thinks about us is not known. I don’t know how he sees me — as a grandma, mother or friend. I became Gopi and started narrating from his view point. There are hardly such attempts made in literature.
What about Science and Technology writings in Kannada?
There is a huge gap. People who are experts in Science and Technology do not have good knowledge of Kannada and vice versa. This gap can be filled only when people who have knowledge in Science learn to read and write in Kannada. In other languages, such attempts are made and are quite successful. For instance, in Tamil, there are a good number of people who excel in Science and are good at Tamil and they are writing books. When they can, why can’t we?
Will you be present at the Kannada Sahitya Sammelana beginning on Wednesday?
No, I will be touring for the next ten days. Frankly speaking, I write because I enjoy. I do not attend events. The present trend in Kannada literature is that people from different fields have started writing. I am happy about it. Literature is not just limited to people who study it as part of their academics. People who come from other fields have a different vision and perspective.
How can we make children learn Kannada?
Parents play a big role. If their mother tongue is Kannada, they have to speak to their children in that language.
How can one promote the language?
It’s only through pride and love that we can develop and popularise Kannada. A language will blossom only when you have love for it. This love for Kannada will not come by giving incentives. It has to come from the heart.
Do you think Kannada is losing its place in Bengaluru?
If two people are speaking in English in Bengaluru, most likely they are Kannadigas. Normally, we do not converse in Kannada even when we meet a fellow Kannadiga, while that is not the case with people from other states.
I want you to tell us what those lowest moments of childhood felt like in one word.
What did you think was gonna happen?
Take me to the, I want to go to the Science Test and the grades you got because that seemed like a pivotal moment.
What do you attribute that to?
What was the toughest moment for you when you were growing up?
Now, we're sitting here in 2019, we have the luxury of perspective but at that time when you're in it, what did the pressure feel like to prove yourself to your parents?
I want to go there, what was the pressure like? How did it feel like internally?
You were the oldest child in an immigrant household. Obviously, you set the example, you were also the litmus test right! Was your upbringing a bit different?
So, tell me, what was Life like growing up in a household where you are basically growing up in two cultures. One at home and the other outside.
When you were younger, you were a kid, early Elementary School, what did you think one day happiness would be?
What is Happiness?
One other thing quickly, Empathy Wines. Why do you call it that?
It’s the single word that I most resonate with most. I think being an empath has changed the course of my life. If that trait didn’t come to me through the DNA strands that my mom and dad gave me I would be a very different man.
How do you decide that?
When do you know that you’re the greatest entrepreneur of all time. You don’t. That’s part of it. I don’t get to decide there is a trophy, this is about intent. This is where I think people don’t understand the bigger meaning of what I’m saying when I say I want to be the greatest entrepreneur of all time. It means that I want to give to entrepreneurs at a level that nobody’s ever given before. Doesn’t mean at 87 there’s some fucking weird Academy Awards. That’s not going to happen. I don’t believe that she or he is going to make the most money. Nobody gives a fuck when the person with the most money dies. People care when somebody who gave dies. When some random person with $19 billion from the Forbes list does, nobody gives a fuck. When Prince dies we shut down for a day or two because he gave through art, something that impacted you. You gave a fuck about Purple Rain. I always tell people about entrepreneurship, it’s like fantasy sports, nobody cares about anybody else’s fantasy team. Nobody gives a fuck how much money I’m going to make. When somebody sees Warren Buffett or Zucks or Bezos, they wish they could have that much money. They’re not like “Yay Bezos!” Nobody gives a fuck about anybody else’s money. People care about what you did for them. That’s why I have a shot because I’m going to spend the next 50 years giving to the game that gave to me. You care more about me because you started the meeting with “I can never pay you back.” Think about how that makes me feel. That’s amazing. You know how many people are like “Gary Vee’s an idiot, that dude would have paid $20,000.” You’re an idiot. You’re playing minor leagues. I’m trying to go to the Hall of Fame.
I can not believe you put that out. It is ridiculous. We have six copies printed at our office because everyone has to have it. I’ve only done 15% of it and my whole fucking business has turned around.
Brother, I want to be the greatest entrepreneur of all time. I don’t know if I will be.
Went right back into the business.
Yep. You know a fun thing right now that’s going on in my world is people like “Gary V, you’re full of shit! You’re saying that you made no money in your 20s but how the fuck did you have money to invest in Facebook and Twitter?” I saved. When I made $43,000 one year I saved $5,000 that year. You know how many people make $43,000 a year and collect $8,000 in debt because they needed to go to Coachella and drink Blue Bottle Coffee. I lived in $1,100 a month apartment and I bought nothing and went on no vacations. I bought no clothes. Didn’t spend any fucking money. I don’t buy shit. When did you see my content model?
There’s so many people who want to build bigger companies, how did you scale so fast?
By not caring about profit. Most people don’t build big businesses because they take the money off the table and buy dumb shit. We went from $1 to 3 to 14 to 27 to 58 to 73 to 100 million in revenue. Which is great obviously. But I never made money.
How many employees?
Your company VaynerMedia, now VaynerX, which is the holding company of how many companies?
4, 5 or 6.
Pick up basketball.
Or program or sell lollipops or be a designer or do post edit production. Nobody is good at everything. LeBron sucks at science. That’s why athletes and actresses and singers are put on pedestals. Who were they as kids? They were pot committed to their talent.
I know you speak about your mom a lot, about her giving you this self-esteem. How did she bring that out?
She overemphasized when I was being kind. “You’re a nice boy. That was so nice.” When I was nice to kids that were getting picked on, she made that a big deal. She also held me accountable. Report cards, punished. 0–4 in baseball, you suck, not the coach, not the sun was in your eyes, not anything else. So it was a positive reinforcement of good behavior and accountability when results weren’t there. I think a lot of people go over positive and it becomes delusion. I think that’s why we have a soft culture. That’s why I talk about eighth place trophies. I think that’s a place where we’re hurting kids. So what if you suck at baseball?
And that might go down to your kids now.
My hope is the ones that are consuming me are going to be the ones that stop it. It starts with forgiving your mom because they have to realize it was her grandfather and then they realized it was her great grandfather. And then you start realizing your mother didn’t have the luxury of the Internet where she could have stumbled upon somebody like me. It’s not that I’m fancy. I’m just saying they didn’t hear other voices. We live in the generation of hearing other voices, people focus on the extreme shit that’s getting banned and all that. What about the positive shit? Do you know how much we can change people? This is why positivity needs to get louder. I’m not on Twitter and Facebook and Instagram trying to debate everybody like everybody else is. I’m not trying to convince anybody, convincing doesn’t work. You’re not going to convince somebody that sees the world differently to see it your way. That’s audacious. I’m gonna live and create examples and create collateral happiness and positivity.
Please elaborate on that.
Most people are unhappy because their parents fucked them up because they wanted them to be doctors, lawyers or engineers. Or because the parent is unhappy themselves, so they’re deploying misery loves company. My big thing is you don’t have to hate your mom. If your mom fucked you up because she’s the negative one you don’t need to hate her. You need to go up the ladder. Your grandma fucked your mom up. Put pressure on the person that’s negative and you’ve come to realize it’s your mom or dad; don’t hate them, actually be empathetic to them, just don’t live under that Geist. That’s a big one because what it’s going to lead to if you don’t forgive and understand they got fucked too, then you’re going to resent and that’s going to encompass you.
You could feel your passion in that.
I felt it in that moment. And the moment is what basically has happened in the world which is I just knew in 2008 for sure, it was like that the world was about to change because of the Internet. And social media in a way that nobody was understanding, that everybody had a chance. The Internet doesn’t care what country or what your race or gender is. It’s the truth. People are shitting on it. They should be loving it. They’re shitting on it because they didn’t realize how fucked up we were and we’re getting exposed by the Internet, by social. There is no social network. There’s platforms that we feed all on everyone’s social. Social media doesn’t suck. We suck. Social media is the mirror. It’s funny to me when people say Facebook sucks. There is no Facebook. Facebook isn’t CNN and Fox News. Facebook is a platform. We’re Facebook, whose Facebook? Zucks is not posting, we feed it. Your Facebook, your fucking FaceBook. But I mean every day now people say social media is ruining us, we’re ruining us. We fill the pipes, we’re the water in the pipes. Our water is contaminated, we’re the problem. Which is amazing because now we’ll eventually get there and then we’ll fix it and get better. I just knew where that talk was going to go. I went out there and I just shot my shot. I do and everybody’s like “look this is the greatest year ever.” I told everybody they can do anything. Let’s not think about trillions. Let’s think about tens of thousands and be happy. It’s funny when people say, “Gary, you push hustle and burnout.” What are you talking about? My signature talk is about being happy, making eighty thousand a year talking about Smurfs. That is the polar opposite of burn yourself out and buy a mansion. Everybody’s thinking I’m pushing hustle porn, I get it, I like hustle. Yes, I think work ethic matters, but equally, please listen to what I’ve been saying for a decade. I want people to be happy, if you’re happy making $42,000 a year working at Rogers at a 9–5 in Canada, fucking live your life. I’m not judging. That’s basically what I was saying there, which is Smurf It Up. If you love the Smurfs more than anything else in the world please start a Smurf podcast or video show at night. Maybe three years later after doing it every night, because you will do it every night, because you want to talk about Papa smurf … you can build a little niche audience. What this all means is if you have a passion or an interest or a hobby, I believe your hobby can be your business. [You can be successful] if you start making content around it in podcast, video or written form which eventually can lead to you selling merchandise eventually lead to you being the speaker on the subject matter, a personality, a subscription based business and events business. Smurf Con once a year in New York and you make a $100,000 and your life is better doing something you love. Maybe something as small as Smurfs can only make you $200,000 a year and you might be making $330,000 as a corporate lawyer, but I’m saying do that and stop buying fancy cars and homes and jewelry so that you’re happy. This has all been one game for me over the last ten years to get to this place where I can articulate what I mean which is let’s get happy out here, we have to redefine success. Success cannot be Lamborghinis, mansions and boats. Success has to be being happy because people are not happy and happy is fun. That’s what led to keeping up with the Joneses. That’s what’s led to me going hard after mothers and fathers.
We were talking off air, you asked me how I heard about you and it was a few years I saw a YouTube video, you talked about Smurf It Up. How did that come about?
Oh, I’m so improv. I was giving a keynote and I was trying to make a point. This was 2008, and that’s the talk that made me write Crush It. I got offered to speak at this Web 2.0 Summit in 2008 at the Javits Center. And there was two very important tech guys in the green room with me, Fred Wilson who’s an amazing all-time venture capitalist here in New York and Jason Freed, the incredible founder of 37signals, wrote a book called ReWork; actually a very different point of view of work/life balance to the extreme. I’ll never forget this. I looked at both of them and I remembered the energy I felt, I go “something’s about to happen.” Either good or bad but I could feel the chemicals in my body being different. I haven’t spoken a lot at that point. This may be my 10th speech ever, 8th or 9th. Super early.
It’s not the final score.
I like boos in the third quarter, I use this analogy lately. I like it. I actually thrive over that. I think a lot about basketball because I get really into it last year, the Knicks were about to have a big off season. I’m a Knick and Toronto goes on a 13–0 run to start the third quarter and we call timeout and the whole Garden is booing, I love it. And this is something I’m trying to figure out how to explain to people because that booing is killing everybody. And now that we have social the booing is on the record. People are crushed by negative feedback from their mother, from their spouse, from their boss, from the general public, from anonymous comments on social. And I feed off of it. I laugh when I see kids or people trying to hate on me. If this person knew that negative content is actually feeding me, and not bringing me down, they’d be so fucking devastated. They’re literally spending 20 minutes right now to try to hurt me, and they’re actually feeding me to be stronger than ever. I never reply to somebody who hates me because I think I don’t want to deploy negativity. I don’t like negativity. So somebody shitting on me, if they actually knew the truth, which is that it actually feeds me. I think I’m scary because I can’t hear you. You say I’m the best. Cool. You say I suck. Cool. You try to hurt me by saying I suck. Cool. When you’re not penetratable by outside feedback you’re fucking dangerous.
How does that happen?
I think in general a lot of what I am is a contradiction, and so I think that’s where a lot of this is happening. So I’m able to be accountable but I don’t dwell. Being accountable doesn’t mean you beat yourself up. I never say I suck, but I’m aware that I lost. That’s different. Just because you lost doesn’t mean you suck. And that’s how I think about it.
Do you think it’s the cameras and social media? That’s the shit that’s going to expose them?
A hundred percent. Do you know how many guys are walking around scared right now? Why? Because they know they pinned a woman against a wall and did something inappropriate 13 years ago. I walk around light as a fucking feather. I knew that was going to happen 20 years ago. And because doing the right thing is always the right thing, it’s something I say a lot. I’ve loved that I was parented by a tremendous mother so I know who I am. I’m not perfect. I’ve got plenty of shortcomings but I know what I’ve done and what I haven’t done and you live that life and I’m also willing to deal with my circumstances when I do the wrong thing. When I make a wrong business decision and the business feels the effects of that. I don’t blame other people. I’m extremely accountable. And people get mad at me for that sometimes. That’s not a good way to look at it, you get depressed. Optimism and confidence along with accountability is incredible. I have accountability. I also say don’t beat yourself up. I don’t judge myself. I am fully accountable yet I don’t have the ability to judge myself when I fail.
Look there’s people that knew I was going to come see you and they were thinking you’re a snake oil salesman, because they haven’t dug deep enough.
The reason I don’t get upset when people kind of take a hot take at me is because I don’t have the audacity to think somebody should spend an hour digging into me. Are they supposed to spend an hour consuming all my content to get a good read on me? I think that’s audacious. I think that’s insecurity. So when people have hot take, I get it. I know how excited I can get. I know that in a 30 second video how I can come across because when the lights go on I feel like I’m an athlete. The lights are on, I’m in. And for me when the lights are on a piece of content that’s me when I’m wearing my uniform and performing. In real life though, I don’t have athletic ability but when I try to scrap it up with friends I’m dirty, like I want to win at all costs. When the game’s over I’m not happy I tripped that guy. I don’t feel good about it. It’s just I can’t help it. And I think that’s if you’re self-aware enough and that’s what can come across in my content. The reality is the truth always speaks in the end. You know there’s a lot of fake good guys out there. And I like that the world starting to expose them. I like it a lot.
Do you think it’s egotistical?
I think it’s self-awareness. I’m incredibly confident and I think ego is insecurity. So I think it’s confidence speaking and then I think confidence is more palpable when it comes with humility. Listen, there’s a lot of people who see one Instagram video of me for a minute and they’ll not like me because I’ll be hot and excited or personable. The reason I think most people end up liking me, if they really go down the rabbit hole, is there’ll be something that I’ll do that will make them realize in all the bravado and all the East Coast, there is an equal amount of humility, patience, kindness and it’ll be that light that will be: “I didn’t expect that from him.” And I think that that’s important. I think you know that just comes with the mixture of DNA and experience. But for me I got quiet, and what you’re referring to, if people don’t follow me is I talk a lot about being quiet. If you go to my latest post on Instagram there’ll be eight hundred people that are saying outlandish things like “you’re Jesus!” I’m like “alright, let’s calm down.” People really get fired up about me and then there’ll be eight people that are like “you’re a snake oil salesman, you’re full of shit. What the fuck, this guy’s getting rich over talking about common sense.”
How did you get so fucking quiet in your head? Because I’m getting there and I’m not just saying that.
Practice. See you just said something very important, you said something powerful. “I’m getting there.” Why? Because you’ve listened to me, and it became something you’re believing in. And once you started tasting it you can’t untaste it. It’s very unnatural to think giving more than taking leads to more for you. But it’s the truth. Especially if you’re talented.
Well there are a lot of people want to tear down buildings, not help others try to either build up theirs or just build bigger buildings, like you say.
Yeah. What you’re referring to, and I appreciate you calling that out, is one of my favourite things. I think if you’re great you don’t spend time tearing other people’s buildings down. The reason I give away all my best advice is because if somebody is better executing than me it’s going to happen anyway. So I think the world has abundance. My success is not at the expense of anybody else’s. Nor is it the other way around.
Let’s take it back for a bit. There’s a couple of people who don’t know you are. What’s your origin?
1.3 billion don’t know who I am. I’m an entrepreneur immigrant from the former Soviet Union. I grew up a hustler kid in Jersey in the 80s and 90s. I’m all those cliche things: immigrant, cursing, Jersey, competitive, feisty, hungry, ambitious. But I’m also Tamara Vaynerchuk’s son, she is an emotional, intelligent juggernaut. She’s quiet. She’s a mother of three. She is not super social. She’s definitely not out there but she has talents with empathy and gratitude and kindness that I completely absorbed DNA wise and then was parented by. So I think I’m an unusual alpha business winner, in that I’m building big businesses, I invest in a lot of big fancy companies. All my Tumblr and Facebook and Twitter and Uber stuff around here. I’ve built multiple huge companies and I’m a successful and wildly followed on social media entrepreneur. I think I’m coming at it in such a different way than the other people that entrepreneurs look up to and I think it’s the thing I’m most proud of, which is I think I’m putting words [into minds of] especially alpha males but alpha females too. I’m putting words in the vernacular that had just not been part of the winning business culture. The words empathy and gratitude and kindness and patience were not the words coming out of 26 year old entrepreneurs saying that they’re going to kill it or crush it.
Where did you get the patience from?
I think I’m way more practical than people realize because I’m so high energy and sometimes that seems less practical. I also think it’s based on my ambition. My ambition is not to own a Lamborghini. My ambition is not to own a mansion. My ambition is to try to buy the New York Jets. That’s my kind of selfish, kind of fun ambition. My immigrant rags to riches kind of thing. My ambition is to leave a legacy, and that’s forever.
What do you mean by that?
Well when you’re hungry and ambitious and want to fuck up the world and want to dominate, patience seems foreign. It seems anti-cultural. When people think of themselves like “I’m gonna win.” They don’t normally think I’m gonna win in 80 years.
It’s been amazing not only for my team to see, but really for the world to see what you’re doing. I could talk about all the little things that I’ve copied you on because you’ve allowed it, but I really want to give back. I can’t pay you back for what you’ve done and the education that I’ve gotten from you. I want to talk a little bit about something you’ve taught me: patience.
Yes. Patience comes hard for alphas.
What are your views on entrepreneurship ?
Does speed becomes your ally when you're able to move and take action quickly ?
How to build a personal brand ?
How can one ease out the aftermaths of rigorous struggle?
What propels you to dream big?
How do I find my passion?
How much of the storytelling of an entrepreneur should be aspirational?
How to make a team to start your own business?
What advice you have for people who want to help their business with videos or podcasts or other media?
What was the turning point in your life?
What did you think when you were about to take a new challenge called VaynerMedia
Why did you choose to run your dad’s store instead of doing your own thing?
What is it like to have a dad who works all the time?
What was the toughest part for you when growing up?
Did you had some kind of pressure as a child?
What was it like to grow in a household with two different cultures?
Does your wife interfere in your business?
What’s your best advice to the leading growing business teams?
How do i run my social outlets without making it feel like a spam?
What are the new emerging apps?
Thoughts on politics?
In the age of digital media how do you suggest one can maintain a solid print audience?
What was your favourite baseball card?
When do you know when you’re ready to start a business?
Who’s the best you entrepreneur according to you?
Where do you see yourself in 10 years?
Part of the world where business is exploding?
What is the best success story you’ve heard?
Who is the leader everyone should follow?
What’s your biggest failure and what did you learn from it?
Which is the company which should be paid attention to right now ?
What are the three most important things before starting up?
What’s the most important advice you got in life?
How do you use social media top help our business?
How to be self aware?
When did you decide to introduce a new position called Chief Heart Officer in your business and What is it?
How did your mother help you build self esteem?
What if people don’t like what you produce?
Do you ever judge yourself?
What do you want to instil in your kids?
How do you identify that there is a trend which is going to start?
What to do when some one close to ou has passed away?
If you were to die today what would you have done differently?
There are so many negative people and negative energy around. How to handle those situations?
How do you understand that you are working in the right job ?
What qualities of people attract you?
What would you tell your child if she wants to walk the same path as you and says that she doesn’t want to open a book?
Do you feel that all your DailyVee vlogs are great?
Tell us about what your Mom used to tell you as a child and what did you do at school when you were small?
How important is it for entrepreneurs to brand themselves? How important is it to tie their name to the business?
When your daughter turns 14 and if she says people don’t like what she puts out on social media, what would you say to her?
Which iconic brand do you think has meant so much in the past but now doesn’t?
What is the most timeless lesson you learned from selling baseball cards and carried it till today?
When you’re on vacation do you disconnect from everything?
What things have you done which haven’t worked?
Can a 40 year old person be called an entrepreneur if he’s worked as a non entrepreneur all his life?
How to be positive when one has everything going against him?
What to do if you hate your job but can’t risk quitting it because you have 4 kids?
I have so many problems, how do i deal with it?
If the mindset is skewed how to fix it?
What to do if others think my product will fail or i will fail in a certain pursuit?
Why is it important to get attention? Where to get the attention of the customers we want?
When to ask people to buy your product?
How to figure out my passion?
What is the most important thing sales employees should focus on?
How accountability affects one’s personality?
How to serve your customers better?
What kind of product should we sell?
What to do if you think something won’t work out?
What to do if i don’t want to do the job my Dad asks me to do?
How do you get motivation?
How long does it take to become successful?
How to gain and retain customers?
What if I am not good at many things?
What’s you trick to get past the bad/ tough days in entrepreneurship?
Please explain your businesses to me
Is it easy to create a lot of content regularly?
Would you ever go out with an IPO?
How many posts do you you post everyday on social media?
Why is it important to know your objective?
How to go forward if one loses motivation?
My friends are doing different things and they’re succeeding at it, but i am not. What should i do?
What’s better being average at different things or being the best at one?
Why is believing in your business important?
Why shouldn’t we not dwell on mistakes?
Why be pumped up everyday? And why is it important to be excited on Mondays?
Do young entrepreneurs understand what the implications of raising money are?
You hold stakes in Uber, pinterest and snapchat. What if their valuations go zero?
Why did you build Vayner Media?
What are your vulnerabilities?
Has working out made your performance better?
Are you good at Basketball?
How can you do so many things and be so good at each one of them?
When did find out that you’re a genius?