Gary Vaynerchuk Curated

Entrepreneur, author & speaker

CURATED BY :  


  • When did find out that you’re a genius?

  • How can you do so many things and be so good at each one of them?

  • Are you good at Basketball?

  • Has working out made your performance better?

  • What are your vulnerabilities?

  • Why did you build Vayner Media?

  • You hold stakes in Uber, pinterest and snapchat. What if their valuations go zero?

  • Do young entrepreneurs understand what the implications of raising money are?

  • Why be pumped up everyday? And why is it important to be excited on Mondays?

  • Why shouldn’t we not dwell on mistakes?

  • Why is believing in your business important?

  • What’s better being average at different things or being the best at one?

  • My friends are doing different things and they’re succeeding at it, but i am not. What should i do?

  • How to go forward if one loses motivation?

  • Why is it important to know your objective?

  • How many posts do you you post everyday on social media?

  • Would you ever go out with an IPO?

  • Is it easy to create a lot of content regularly?

  • Please explain your businesses to me

  • What’s you trick to get past the bad/ tough days in entrepreneurship?

  • What if I am not good at many things?

  • How to gain and retain customers?

  • How long does it take to become successful?

  • How do you get motivation?

  • What to do if i don’t want to do the job my Dad asks me to do?

  • What to do if you think something won’t work out?

  • What kind of product should we sell?

  • How to serve your customers better?

  • How accountability affects one’s personality?

  • What is the most important thing sales employees should focus on?

  • How to figure out my passion?

  • When to ask people to buy your product?

  • Why is it important to get attention? Where to get the attention of the customers we want?

  • What to do if others think my product will fail or i will fail in a certain pursuit?

  • If the mindset is skewed how to fix it?

  • I have so many problems, how do i deal with it?

  • What to do if you hate your job but can’t risk quitting it because you have 4 kids?

  • How to be positive when one has everything going against him?

  • Can a 40 year old person be called an entrepreneur if he’s worked as a non entrepreneur all his life?

  • What things have you done which haven’t worked?

  • When you’re on vacation do you disconnect from everything?

  • What is the most timeless lesson you learned from selling baseball cards and carried it till today?

  • Which iconic brand do you think has meant so much in the past but now doesn’t?

  • 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?

  • How important is it for entrepreneurs to brand themselves? How important is it to tie their name to the business?

  • Tell us about what your Mom used to tell you as a child and what did you do at school when you were small?

  • Do you feel that all your DailyVee vlogs are great?

  • 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?

  • What qualities of people attract you?

  • How do you understand that you are working in the right job ?

  • There are so many negative people and negative energy around. How to handle those situations?

  • If you were to die today what would you have done differently?

  • What to do when some one close to ou has passed away?

  • How do you identify that there is a trend which is going to start?

  • What do you want to instil in your kids?

  • Do you ever judge yourself?

  • What if people don’t like what you produce?

  • How did your mother help you build self esteem?

  • When did you decide to introduce a new position called Chief Heart Officer in your business and What is it?

  • How to be self aware?

  • How do you use social media top help our business?

  • What’s the most important advice you got in life?

  • What are the three most important things before starting up?

  • Which is the company which should be paid attention to right now ?

  • What’s your biggest failure and what did you learn from it?

  • Who is the leader everyone should follow?

  • What is the best success story you’ve heard?

  • Part of the world where business is exploding?

  • Where do you see yourself in 10 years?

  • Who’s the best you entrepreneur according to you?

  • When do you know when you’re ready to start a business?

  • What was your favourite baseball card?

  • In the age of digital media how do you suggest one can maintain a solid print audience?

  • Thoughts on politics?

  • What are the new emerging apps?

  • How do i run my social outlets without making it feel like a spam?

  • What’s your best advice to the leading growing business teams?

  • Does your wife interfere in your business?

  • What was it like to grow in a household with two different cultures?

  • Did you had some kind of pressure as a child?

  • What was the toughest part for you when growing up?

  • What is it like to have a dad who works all the time?

  • Why did you choose to run your dad’s store instead of doing your own thing?

  • What did you think when you were about to take a new challenge called VaynerMedia

  • What was the turning point in your life?

  • What advice you have for people who want to help their business with videos or podcasts or other media?

  • How to make a team to start your own business?

  • How much of the storytelling of an entrepreneur should be aspirational?

  • How do I find my passion?

  • What propels you to dream big?

  • How can one ease out the aftermaths of rigorous struggle?

  • How to build a personal brand ?

  • How do you make determinations on where and how you spend your time, knowing how valuable and how limited your time is ?

  • Does speed becomes your ally when you're able to move and take action quickly ?

  • What are your views on entrepreneurship ?

  • 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 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.

  • 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.

  • 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.

  • 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.

  • 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.

  • 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.”

  • 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 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.

  • 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.

  • 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.

  • 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.

  • 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.

  • 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.

  • 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.

  • 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?

  • 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.

  • Your company VaynerMedia, now VaynerX, which is the holding company of how many companies?

    4, 5 or 6.

  • How many employees?

    A thousand.

  • 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.

  • 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?

  • 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.

  • 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.

  • 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.

  • What is Happiness?

  • When you were younger, you were a kid, early Elementary School, what did you think one day happiness would be?

  • 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.

  • 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?

  • I want to go there, what was the pressure like? How did it feel like internally?

  • 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?

  • What was the toughest moment for you when you were growing up?

  • What do you attribute that to?

  • 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 did you think was gonna happen?

  • I want you to tell us what those lowest moments of childhood felt like in one word.

  • 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.

  • 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.

  • 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.

  • 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.

  • 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?

  • 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 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.

  • 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.

  • 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.

  • 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.

  • 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.

  • 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.

  • 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…

  • 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.

  • 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.

  • 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.

  • 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.

  • 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?

  • 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.

  • 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?

    Yes.

  • 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.

  • 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.

  • 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.

  • 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?

  • 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.

  • 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.

  • 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.

  • 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 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.

  • 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.

  • 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.

  • 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.

  • 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.

  • 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.

  • 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.