Gary Vaynerchuk Works Harder Than You Do

Nobody works harder — and smarter — than Gary Vaynerchuk. That's because the maniac known online as Gary Vee operates on one mode and one mode only: full blast. Gregarious, confident and incomparably charismatic, Gary is never at a loss for opinions on everything from the future of social media and the preeminent importance of authenticity to his almost antiquated but refreshing take on the importance, power and relevance of a committed work ethic – a welcome breath of fresh air that stands in stark contradiction to our pervasive, myopic lifehack culture — a regrettable, technocrat popular trend that woefully overvalues false promise short cuts to success over passion, service and fidelity to the journey. Internet omnipotent with over 1.2 million followers on Twitter, 500K+ Facebook friends and a vast and loyal YouTube subscriber base, I suspect many of you are already daily consumers of Gary's persistent, relentless feed of videos, blog posts, social media updates, Snapchat stories and live casts. For those unfamiliar, Gary is a Belarus-born entrepreneur, venture capitalist and CEO of NYC-based VaynerMedia, one of the fastest growing digital ad & marketing agencies in the world. A mainstay on YouTube, Gary hosts the hugely popular #AskGaryVee Show and dons protagonist duties on #TheDailyVee, a surprisingly hypnotic, behind the scenes gander into Gary’s everyday business life. You've seen him profiled in the New York Times, The Wall Street Journal, GQ, Time and Fortune's annual list of 40 under 40. You've watched him on Late Night With Conan O’Brien and Ellen. And maybe you've even read one his three New York Times bestselling books, Crush It*,Jab, Jab, Jab*, Right Hook*,The Thank You Economy* and now #AskGaryVee* – his newest offering which hits bookstores everywhere March 8. A compelling and entertaining distillation of practical, timeless workplace advice on entrepreneurship and management for anyone launching their own company, working in digital media, starting their first job or simply seeking inspiration, Gary's fourth book is certain to be a massive, ubiquitous success. A legitimate marketing & business genius, Gary is a kick in the pants – loud, irreverent and unconventional. But he’s also incredibly warm, personable and quite giving when it comes to freely sharing a seemingly endless stream of good ideas, tools and strategies he credits as part and parcel of his personal success equation. Conversing with Gary is a bit like trying to wrangle a wild horse, so this one is a bit all over the place. Enjoy! Rich Learn more about your ad choices. Visit podcastchoices.com/adchoices

Speaker names marked ? are inferred from speaking time and the show’s known hosts — they are not voice-verified.

• 0:00Rich Roll?

  Eating well rarely falls apart because of one big failure. It's the daily question that wears you down. Like, what am I actually going to make tonight? What's in the fridge? And it's exactly why we built the Plant Power Meal Planner. It's a personalized, plant-based meal planning program that matches you with recipes based on your taste, your allergies, your cooking skills, and how much time you actually have. You build, through this program, a balanced, nutrient-dense plan for your entire household in a few minutes. Then it generates a grocery list for you with one click that plugs right into our delivery partners. All the recipes in the program are built by dietitians with culinary training. Plus, you get your own food coach to help you problem-solve along the way.

• 0:44Rich Roll?

  It's kind of an amazing thing. For listeners of the show, all you special people, we're offering an exclusive $20 off an annual subscription right now. To get it, go to meals.richroll.com, take your quick personalization quiz, and enter promo code RICHROLL20 at checkout.

• 1:05Speaker 01

  You've got to know what you're good at. That's the game. If I had a potion that could allow somebody to fundamentally become self-aware and know what they're good at, they would all win.

• 1:17Rich Roll?

  That's Gary Vaynerchuk, and this is the Rich Roll Podcast.

• 1:33Rich Roll?

  Hey, everybody. How are you all doing out there in audio infotainment land? My name is Rich Roll, and it's not by accident that I am the host of this here show, aptly titled "The Rich Roll Podcast." For the newcomer, this is the show where I sit down with the outliers, the big thinkers, paradigm-breaking minds and personalities across all categories of culture change. Everything from health and wellness to fitness, nutrition, meditation, and mindfulness, spirituality, art and creativity, and in the case of today's guest, business, entrepreneurship, and the incredible power and leverage inherent in the internet to... Forge your own path to, in the words of my friend, James Altucher, "Choose yourself."

• 2:18Rich Roll?

  My goal, you ask? To help all of us discover, uncover, unlock, and unleash our best, most authentic selves. So, thank you so much for tuning in today. I know there is a lot of content out there vying for your attention, your ears, and your eyeballs, and your hearts. And I don't take you guys for granted, not for one second. And greatly appreciate your decision to spend a little time with me today. And mad love shout out to everybody out there who has made a point of showing their support for this mission by making a practice of always using the Amazon banner ad on richroll.com for all your Amazon purchases. Click the banner right there on each and every podcast episode page. It takes you to Amazon. Buy whatever

• 2:59Rich Roll?

  you're gonna buy. Doesn't cost you a single cent extra. But Amazon credits us with a little commission. It's a great, simple, easy, free way to support the work I do here each week, and it is greatly appreciated. So, thank you very much. So, really excited about today's show. I got Gary Vaynerchuk, Gary Vee, as he is known on the internet. This guy is a bit of a maniac, and I say that in the best way. He is full speed ahead. He is an idea generating energizer bunny, just bursting with ideas and opinions on everything from the future of social media to the importance, power, and relevance of

• 3:39Rich Roll?

  a committed work ethic, which is a welcome breath of fresh air, in my opinion, in our life hack culture. A culture that really overvalues shortcuts to success, wealth, health, and happiness. And I got all kinds of additional things I want to say about Gary before we dive into the conversation. But first...

• 4:06Rich Roll?

  All right, today's show. I suspect a lot of you, perhaps most of you, I don't know, already know Gary Vee due to his omnipotence on the internet. The guy's got 1.2 million Twitter followers, half a million Facebook followers, a vast and loyal YouTube following, and he's one of the biggest names on Snapchat. He's pretty hard to miss and never at a loss for words, opinions, or new ideas. But for those of you that aren't familiar with Gary, he is a Belarus-born entrepreneur and CEO of New York City-based VaynerMedia, which is one of the fastest-growing digital ad and marketing agencies in the world. He's also an angel investor and early-stage venture capitalist. He's a guy who got in early on

• 4:47Rich Roll?

  Facebook, Twitter, and Tumblr. That gives you an indication for his investing sensibility, his radar, his antenna. Gary's a mainstay on YouTube these days. He hosts the hugely popular Ask Gary Vee Show and is the protagonist in The Daily Vee, which is a vlog on Gary's everyday business life. He's also a multiple New York Times bestselling author of several books, including Crush It!, Jab, Jab, Right Hook!, The Thank You Economy!, and Ask Gary Vee, his newest book, which comes out this week and will no doubt be impossible to miss. He's been featured in The New York Times, The Wall Street Journal, GQ, Time. He's appeared on Late Night with Conan O'Brien and Ellen. He's been named to Fortune's list

• 5:29Rich Roll?

  of 40 Under 40 and Business Week's list of 20 people every entrepreneur should follow on social media. I had a ton of fun with Gary when I was in New York City the other week. He is a marketing and business genius. He's a kick in the pants. He's loud, irreverent, unconventional. He's maniacal and somewhat fanatical, but he's also very warm. His energy is really infectious. And over the years, he has personally inspired me in my various entrepreneurial pursuits because he knows how to get things done and is very open and giving when it comes to sharing his ideas and his strategies. Interviewing Gary is a bit like trying to wrangle a wild horse, so this one is a little

• 6:12Rich Roll?

  bit all over the place, but it's also packed with some awesome gems. Some of the things we talk about today include... The difference between lifestyle and life hacking, Gary's iconoclastic ideas about balance, life balance, what it means to day trade attention, the incredible impact of the internet on forging your own life path, his perceptions on the future of social media, the romantic allure of entrepreneurial life versus the day-to-day reality, and differentiating between valuable online content and online snake oil salesmen. So let's step into the VaynerMedia conference room,

• 6:55Rich Roll?

  made famous by his Ask Gary Vee Show, and well, Ask Gary Vee some stuff.

• 7:09Rich Roll?

  Yeah, I was just telling D-Rock that he's doing an amazing job. They're getting better and better and better. I just watched the most recent one this morning, and you're doing an amazing job of just crystallizing the most important parts of the day and doing it in a concise way.

• 7:24Speaker 01

  We're gonna pound them in the other direction for the next one. We're on like 34 minutes to just exhaust. Like, we're finding, like, you know what I mean? We're gonna do some different balances, so.

• 7:32Rich Roll?

  Here, slide up on that a little bit.

• 7:33Speaker 01

  You want closer?

• 7:35Rich Roll?

  Yeah, I'm interested in how the YouTube journey has been since you started the Daily Vee and what the idea behind that was.

• 7:44Speaker 01

  You know, it's just, it's the thought of like, to me, really, Daily Vee, more so than the Ask Gary Vee Show, was predicated on making sure people really know what's going. I don't want to convince anybody to do it my way. I just want them to not be confused on what's really happening here, where every minute for 15, 16 hours a day is being used properly and hardcore. There is no watching funny YouTube videos. There is no hanging around, you know?

• 8:09Rich Roll?

  Right, right, right. It's full-on 24/7 with you.

• 8:12Speaker 01

  It is.

• 8:13Rich Roll?

  And I think one of the things that I appreciate tremendously about your message is it is a, it's quite refreshing in this culture of trying to hack your life and shortcut your way to, you know, whether it's a million dollars or six Back abs or whatever it is, the truth is it takes hard work, man. And despite the fact that everybody wants that super secret VIP notion or idea, or the 10 tips or whatever it is, there's no end run around what it actually takes to do something that inherently is going to have long-term value.

• 8:49Speaker 01

  Period. Like, you know, if that's what's said at my funeral, like what you just said, I'll be super happy. Like, I've been working out every day and eating properly every day for almost two full years now, and I still have no chest muscle. I'm so damn pissed. I'm so pissed. I was telling Mike, my trainer, I'm like, come on, when is this gonna happen? And it just kind of reminded me of like, yeah, like, for somebody that's never put in the kind of workday professionally that I have ever, one time, to do it every day for 24 months, and just start seeing the beginnings of something, has to be frustrating. I, uh, I was, I did a big weight day on Saturday, so I was able to eat a little bit. I gained four pounds, you know, and obviously there's water weight and things of that nature,

• 9:34Speaker 01

  but like, it takes me two weeks to shred that. And like, I'm like, Jesus, just one afternoon where I was able to act somewhat normal, and that's how work is, right? Like, like, the bottom line is, 99% of people that are listening to this right now, don't work hard enough for what they want in return. That's all.

• 9:54Rich Roll?

  There's a lot of lip service to the hustle, though. You know, it's easy to throw up an Instagram post with a quote on it or something like that, going, you know, 24/7 hustle and all that kind of stuff. But, you know, the reality of most people's daily existence bears no resemblance to the kind of ethos that you're portraying pretty transparently and continually, uh, you know, through your various channels.

• 10:17Speaker 01

  Daily V is a big deal, because it's the one that I get to really show people that, look, I mean, you can only manufacture so much. You can throw $50,000 in cash on a bed and take a picture on Instagram. You can go on a private jet that's not, you can rent $500,000 cars that aren't yours for an afternoon to make it seem like you're that. This is, like, the reason we're gonna go with a 34-minute episode today, instead of the eight and nine, we did the eight and nines, to your point, on D-Rock doing a good job, because, you know, you don't want to bore people. And it's good to make great, he's making great content in that version. But what is this, gonna be 16? The one we're about to put out, episode 16?

• 10:53Speaker 02

  Yeah.

• 10:53Speaker 01

  16, I just wanna, I just wanna make everybody realize, like, hey. Like, it took me thirty-four minutes to watch this. That's how much shit is going on in my day in and day out. And it's every day, every day, every day, forever. And not that I want to say I'm a harder worker than anybody. Not that I want to say this is how you should do it, John. This is how you should do it, Sally. It's that I just want people to not email me anymore and say, Gary, I've been working hard for two years and nothing's happening. When like, I will, I'm funny. I get curious and I look at their like, social media and I'm like, you were home at five-thirty in the afternoon.

• 11:29Rich Roll?

  Right.

• 11:30Speaker 01

  I haven't been home at five-thirty in the afternoon since nineteen ninety-four.

• 11:33Rich Roll?

  Uh-huh. Well, I think that brings up a, an interesting point that I want to explore with you. And it's this idea of balance. Like, I've been thinking a lot about balance lately. And, you know, conventional wisdom is, you know, you should eat a balanced diet and you should live a balanced life. And I know reflecting on, on my own life experience, that the only time that I've actually ever accomplished anything noteworthy was when I allowed myself to be out of balance. And how do I reconcile that with, um, you know, kind of being able to continue to do what I do long-term, right? Without burning out.

• 12:08Speaker 01

  And, and then there's the variables of the other people that are closest to you, right? Like, to add one more layer to what you just said, which is exactly right. What starts happening when you have spouses and children and a million other things?

• 12:20Rich Roll?

  I have four kids, so, you know, everybody has, you know, everybody's important.

• 12:25Speaker 01

  Listen, I am, I am fundamentally willing to put myself out there to say that I'm not interested in the politically correct version of everything right now. I'm not interested in having a conversation around how to raise my kids. I'm not interested in you imposing your will on me, on how I should meditate. I'm not interested. I'm interested in making myself happy, which then will allow me to make the ten people that are most important to me happy. And if that comes through workaholic behavior, then that's what it's going to be. Because I don't know any other gear than to listen to myself. I wish I took my health more seriously in my twenties. I couldn't. I just couldn't get there, right? I'm glad I did. Maybe tomorrow I decide that I want to be a stay-at-home dad, and that's what I'm going to do. I mean, the fact of the matter is, way too many people are trying to,

• 13:10Speaker 01

  and by the way, that's why I wanted to clarify upfront that what I'm doing with Daily V, the hustle to twenty-four-seven, not only is it not for most people, it's barely for anybody at the level that I go at. But what I don't want to do... Is get into this conversation where everybody has to find, balance is defined by a person. Like, every single person's balance is predicated on one. There's no universal balance. Like, you know, we all do it differently. And so, look, by the way, if I, I need the action, Rich. You know, like, I need it.

• 13:43Rich Roll?

  Right, right.

• 13:44Speaker 01

  Like, like, you don't understand.

• 13:45Rich Roll?

  You also have, you have a battery that's unlike most people.

• 13:48Speaker 01

  It's a different battery, and so, I have to feed that battery. Like, people don't understand. Like, I can't, I can't go eight hours a day. Like, I'll break. I'll be unhappy, I'll be depressed.

• 13:59Rich Roll?

  And I think that's what distinguishes you from most people. And I think, uh, it gets confusing when people are inspired by your example, and they're trying to mimic that, but it's at odds with, you know, their own personal constitution.

• 14:13Speaker 01

  100%, which is why I'm trying to do a better job and saying, "Look, I'm gonna post this out there. This is me. Don't be me, be you," is something I've been saying a lot more of. But at the same token, here's my big point. And this is probably the single most important point. I am not allowed to cry about my lack of time with my family, because I made my bed and I'm sleeping in it. That equally means I have no interest in hearing people cry about why their businesses aren't successful if they're working 40 hours a week.

• 14:43Rich Roll?

  Right. Well, they're, yeah, they're, you know, they're entering into a contract, a social contract with their profession and with their family life, and there's a sliding scale of priority there. So, your scale is...

• 14:55Speaker 01

  It's also, you know what the other thing is? Everybody's got a different relationship. Like, if my wife didn't grow up with a dad who was a successful corporate executive, who traveled a lot, and her dad was my, one of my best buds, his wife's dad had a very simple life. He was home at 4 o'clock every single day. He works more and it's massive friction because his wife grew up with that.

• 15:20Rich Roll?

  Hmm.

• 15:20Speaker 01

  And so for her, it's a foreign thing. For my wife, you know, it's not a foreign thing and it's not foreign for me either. And so, you know, you've got, what I know is that everybody has their own relationship. If I fell in love with a different gal, who had a different upbringing, maybe I'd be living my life differently because maybe the lines and that we drew in the sand would have been a little bit different predicated on our upbringing, our DNA, things of that nature.

• 15:43Rich Roll?

  Yeah, well, I think there's probably some confusion out there because you've made a conscious choice to, to not portray that aspect of your life and all the transparent things that you share, right? That's sort of out of bounds. So it probably leaves people with question marks about how that functions.

• 15:58Speaker 01

  You know, and this weekend was the first time I did anything. I filmed episode 1001 and I had Misha there and I kind of referenced her. I referenced both Xander and Misha in my Snapchat this weekend, which is unheard of for me. And it's true, I'm succumbing a little bit to the social pressure because I'm scared that people, like, I want to do right by people. I'm good. By the way, let's, let's, let's just understand one thing. I got real lucky. Like, I'm always happy and I'm always good. You know why? I'm always gonna do what I want to do.

• 16:28Rich Roll?

  Hmm.

• 16:28Speaker 01

  Now, I'm starting to feel a bigger sense of responsibility as more and more eyeballs are on me. And I'm trying to reconcile that because you're right. My wife and I have made a pact. I mean, it's very hard to find pictures of my kids. That my wife, you know, just did a thing for CNBC. They wanted one little picture for one second of Lizzie because she has like packs my suitcase and it was like a reference. Wait, the answer's no. Like, we're private about our family that way, whereas I'm out 24/7. And so all the minutes that are like kind of lost when D-Rock's doing his thing, you know, we've-

• 16:58Rich Roll?

  Is D-Rock allowed inside your house?

• 17:01Speaker 01

  Yeah, he's been in my house, but like, you know, it's like, it's a real thing though. You know what I mean? It's a real thing. Even like being careful of like signage around the neighborhood of the kids' schools when I go for like, you know, like, nobody knows, nobody sees the two hours I spent at the talent show last week in the morning, which is hustle time, nine to 11, right? Um, so I get it. And I understand why people are trying to reconcile and understand it. I guess my biggest point is- Some people have sick parents, some people have college debt, some people grew up super rich and have no pressure and no ambition and no hunger. Some people are just super pumped with the way they have it. They love making a hundred twenty thousand a year, which is incredible, by the way. And they love being able to be not, not dealing with a lot of pressure of owning a business. Like, everybody's got it different.

• 17:46Speaker 01

  My big thing that I'm trying to figure out, and this is a fun interview because you're taking it to a cool direction for me and it's, it's allowing me to think about it, not just in my own self, but through an interviewer asking. I'm trying to figure out how to get the world into a non-complaining zone. I, I, I'm starting to-

• 18:04Rich Roll?

  Good luck with that.

• 18:06Speaker 01

  But you know what? It is my ambition. I'm starting to realize what's happening with me, which is, ah, I know what's, what's driving me. I hate complaining. And I'm not allowed to complain about all the things that I have to give up, like leisure. Like leisure. Like leisure's out the window. Like the Jets are my only leisure.

• 18:24Rich Roll?

  Yeah, but I don't think that you would be leisurely if you were given leisure.

• 18:27Speaker 01

  Correct. My leisure is my business. Eighteen hours a day, working every second, is my happiness. I love it. Like, I'm sorry that not everybody loves it. And you like skydiving, or eating dinners, or being on the basketball team. I'd rather be in two meetings, challenging my brain, trying to figure it out, win the game of business, rather than golfing. I don't want to golf. I'm sorry. I don't want to meditate. I'm, I'm happy. Like, you know, and so, what's really important, though, is too many people's actions aren't mapping their complaining.

• 19:04Rich Roll?

  Explain that.

• 19:05Speaker 01

  Sure. The amount of people that complain, but, listen, both sides. Let me start with the one that most people don't think of. I have a lot of ton of successful workaholic friends who want to have dinner with me. They think I'm going to be an empathetic ear where they're going to start the whole entire first thirty minutes of our dinner complaining that they don't spend enough time with their kids. And I'm like, fuck you. I'm like, you can spend, you're plenty wealthy. You're plenty in control. Just go start spending more time with your kids? There's nothing to complain about.

• 19:31Rich Roll?

  Mm hmm.

• 19:32Speaker 01

  Vice versa, the common thing that I think where people think I'm going to is just people complaining about the president, or the economy, or like their assistant, or the hundreds of things that are holding them back, other than deploying real hard work against the singular things that they're best at, to maximize their upside. And then, by the way, the fundamental reconciling with not everybody is good enough to build a billion dollar business, or even a... Do you know how few people are actually capable of building a million dollar business?

• 20:05Rich Roll?

  Not many.

• 20:06Speaker 01

  It's a stunning number. And in the ecosystem we live in, in this podcast universe, entrepreneurial universe, the social media universe, all of a sudden, there's a misconception that anybody can do it.

• 20:17Rich Roll?

  Yeah, I think that that really is being fostered on a mass scale right now with

• 20:22Speaker 01

  You're damn right.

• 20:23Rich Roll?

  Yeah, the ascent of the entrepreneur as sort of this rock star and this aspirational lifestyle, and you're kind of, you know, casting a different shadow on it and saying, this is what it's really like. It's not so sexy.

• 20:35Speaker 01

  I'm trying to show my bags under my eyes at 1:30 in the morning at the Atlanta airport, and I'm saying, look, I'm pretty fucking wealthy, and yet I'm sitting here like disgusted with my like, death of like my day, like, just like, it's hard. This is super hard. By the way, I haven't even gone into, and I haven't figured out how to go into, the real problem, which is the mental stress of running a business where there's 700 headaches. I have been showing that with Daily V, mainly because it affects a lot of other people. When I'm in a meeting and I'm deciding who to fire because they stink, it's not necessarily something I want to put out on the video a month before I actually fire that person.

• 21:13Rich Roll?

  Right.

• 21:14Speaker 01

  Right? So, we haven't even gotten into the mental aspects of having the buck stop with you.

• 21:21Rich Roll?

  Mm hmm.

• 21:22Speaker 01

  The amount of people I know that don't want to be entrepreneurs mainly because they're smart enough to know that the difference of pressure between a number one and a number two is staggering.

• 21:30Rich Roll?

  Yeah. Well, meditation might help you with that.

• 21:34Speaker 01

  But, but here's the good fun thing for me. I'm super pumped with it. Like, I'd even be, like, I'm fine, like.

• 21:39Rich Roll?

  What, what aspect of it?

• 21:41Speaker 01

  Like, I'm, I'm very comfortable with the pressure, but I also know how many people aren't.

• 21:45Rich Roll?

  Right, right. I got you.

• 21:46Speaker 01

  Got it? Like, I don't want to, I mean, I'm not showing it because I'm worried about myself. I'm not showing it because who gets affected by it, but for me, I recognize the stress of it. I just eat it for lunch. I'm, I'm built to eat stress. I love stress.

• 21:59Rich Roll?

  Where does that come from? Like, you know.

• 22:02Speaker 01

  Hard and soft wiring. I think it comes from, I do think that I have a benefit of growing up with not a lot, where my parents had real things to worry about. It's perspective, right? Hard to be upset about champagne problems, like million dollar business decisions, when you knew your parents had nothing, spoke nothing, lived in a studio apartment, smaller than the room we're in right now, and didn't know where their next, you know, like, we're scared.

• 22:24Rich Roll?

  Yeah, yeah, yeah. I mean, I want to kind of explore the superhero origin story a little bit. I mean, a lot of people listening to this know your story, but there's going to be other people that, that, you're, you're brand new to them, so.

• 22:34Speaker 01

  Yeah, for sure, especially in this demo. Yeah. You want me to go into it?

• 22:37Rich Roll?

  Yeah, go, yeah, go for it.

• 22:38Speaker 01

  Look, I was born in the Soviet Union, in Belarus. We came here in seventy-eight. The Carter years were full in effect. Economy was shit. Interest rates were through the roof. My dad was a construction worker in Russia. I thought he was going to do that here, because he had a great uncle who was well off here. Great uncle dies while we're in Italy getting our paperwork. Wasn't so easy for Russians to get into America during the Cold War. And we get here, and, um, you know, he, he gets a job as a stock boy in a liquor store, uh, because that great uncle owned that store and his kids owned it and they didn't want to operate it, or they had managers and.

• 23:11Rich Roll?

  This is in New Jersey?

• 23:12Speaker 01

  This is now in Clark, New Jersey. We live in Queens for the first year, year and a half. We then moved to Dover, which I never talk about for a year. Then we moved to Edison, New Jersey.

• 23:21Rich Roll?

  And you, so was your native tongue Russian?

• 23:23Speaker 01

  Yes. I'm speaking Russian at this point. And, uh, and I'm going outside trying to learn English. You know, it's the early eighties, you know, you're a five-year-old, your mom sends you outside, you can literally be out there for five hours.

• 23:33Rich Roll?

  Yeah, yeah, yeah.

• 23:34Speaker 01

  Like, you know, it's just so different.

• 23:37Speaker 01

  And, uh, and we moved to Edison, New Jersey in August of 82. So I'm six and a half, almost seven, and that's where kind of life begins. I lived there until seventh grade. That's where I make my friend network. That's where I become a Jets fan. That's when I, where I start showing my entrepreneurial wit with lemonade stands and baseball cards. That's when my dad becomes the manager of the store. That's where my dad buys a part of the business. That's where we start becoming, that's where I get Atari. That's where, you know, we have a townhouse instead of a studio apartment. That's where the American dream starts to unfold.

• 24:11Rich Roll?

  Right, and the entrepreneurial spirit was just hardwired into you from the beginning.

• 24:15Speaker 01

  And so, listen, I truly believe it's a hardwired thing. I think for the amount of people that are listening right now that never sold anything or tried to make a buck when they were in junior high or high school, I'm not as bullish on them as entrepreneurs. I just am not. I just don't think it's, and it's no different than anything else. Like, I didn't try to sing when I was six, 10, 11, 15. And so, can I go take singing lessons right now? Yes. Can I become a much better singer than I am right now? I think so. Does that make me even decent at singing? I don't think so. And so, like, just because you go to business school, or just because you listen to your

• 24:56Speaker 01

  podcast, or just because you read 17 of my books, or four, or 17 business books, it means you could be the best version of yourself in the craft of running business and entrepreneurship, which may not be enough to even be borderline successful.

• 25:10Rich Roll?

  Right, right, right.

• 25:11Speaker 01

  I mean, this is real talk.

• 25:12Rich Roll?

  Right. Yeah, no, I appreciate that. I mean, the, the truth is, is, is most welcome because there is this, you know, this fostering that anybody can do it, you know?

• 25:22Speaker 01

  You know why? Because there's a lot of people that can make a lot of money by selling people the system and the dream of it.

• 25:29Rich Roll?

  But right now, we have this mass epidemic of people, and I want to continue with your story, but just to kind of launch on a little different trajectory for a second. You know, most people are stuck in jobs they can't stand. They're sitting in cubicles. You know, they basically feel stuck in a life they're not even sure they consciously chose for themselves. And a message like yours or the other people out there that are entrepreneurs that are sharing kind of transparently online is very inspirational. So when you're speaking to that person who really wants a way out, they're not necessarily going to go found the next Twitter, but they're trying to find a better way to have more control of their life.

• 26:09Speaker 01

  This is what I wrote and crush it. And this is what I'm trying to do right now on the bookends of kind of my career so far as a public figure is you're damn right. And honestly, those are the people, so shit, man, you're really hitting something important to me. Let's, let's break that, you know, we got a little bit of time now.

• 26:22Rich Roll?

  Yeah, let's do it.

• 26:22Speaker 01

  This isn't my usual 15 minute interview, so I got a little time. Let's really, really break this down. So you've got Rick, he's making $62,000 a year in his cubicle. He's got $100,000 in student debt with a huge interest rate that's about to kick in. He can't get out of it. And I understand why Instagram photos of some dude with chicks in Vegas or cash on a bed or some, is very enticing. Let's really break this down. What Rick is getting fed right now by 90% of this market, all that a lot of people think looks like me, is like me, says the same things as me, that I'm trying to very much clarify is the following.

• 27:02Speaker 01

  Rick is being sold in his mind, or Rickette in her mind, that they're going to make big money. See, that's the problem. The problem is most people are not buying into the practicality of entrepreneurship. They're buying into the romance and the high end of entrepreneurship.

• 27:18Rich Roll?

  Well, they're buying into the destination or the result.

• 27:21Speaker 01

  Correct.

• 27:21Rich Roll?

  As opposed to the daily grind and the journey and the process.

• 27:24Speaker 01

  Here's what I think. I think the far majority of people that are listening right now, understanding a little bit about your audience, actually should become entrepreneurs or do entrepreneurial tendencies, but they need to understand they're trading their $62,000 a year job for a business that might make them 62,000. Or maybe what my hope is, and I, my belief, by the way, with the internet now is an 80 to $90,000 gig.

• 27:47Speaker 01

  Which is gonna probably take more time working, not less.

• 27:50Rich Roll?

  Oh, most certainly will take more time.

• 27:52Speaker 01

  But will be a hell of a lot more fun, because at least it's on your rules. Like, you can actually work 11 a.m. to 11 p.m. if you're not a morning person, and you don't have to wake up at 6:30 anymore to be at the office at 8 and sit in traffic for an hour. I just wish there was a bigger conversation, R squared, around making 80,000 a year on your terms versus making 65 on theirs. Or, how about this one? Which I think is actually the wild one of the whole bunch. How about you're making a buck ten, but you're miserable? But it's paying your bills? How about making 87 instead of a buck ten? But being happy as shit?

• 28:27Rich Roll?

  I take that trade all day long.

• 28:28Speaker 01

  I think so.

• 28:29Rich Roll?

  You know, and I think what you're saying really, but really what, to distill it down, really what you're saying is there's a distinction, a very profound distinction, between the sexy IPO versus somebody who's stuck in a dead-end career or something that is not personally satisfying, and trying to find a way by leveraging the incredible power of the internet and the democratization of, you know, sharing content to be able to have a little bit more control and domain over how they spend their time.

• 28:57Speaker 01

  You're also talking to a guy who truly believes that if you go to the Dollar Store, the Goodwill Store, and garage sale on the weekends, and sell it all on eBay, on the arbitrage between what you're buying and what you can sell it on eBay, literally, most people, if they discipline themselves and learn four or five genres, video games, clothes, artifacts, paper goods, can literally make a hundred K a year.

• 29:16Rich Roll?

  Right.

• 29:16Speaker 01

  I mean, that, you know, if I ever made my bullshit ebook, that would be it. Because I really understand all the pieces of how to make 100K on eBay.

• 29:25Rich Roll?

  Right.

• 29:25Speaker 01

  Like, and that's a lot more money than a lot of people listening right now making in their year. Here's the other thing, and this one's probably even more important. Okay, let's take a step back to where I was. You're gonna try to make 100K instead of 80K. By only going for 100K instead of a million. You're gonna make the biggest single important decision of your life. And here's what it is. Most people, right now, because they're going from 60K to try to go for a million, are doing very impatient behavior in their first 24 months out the box.

• 29:58Rich Roll?

  In what respect?

• 29:59Speaker 01

  They're looking for fast and cheap dollars. They're signing up for things that are not as noble. They're trying to sell people things they don't believe. Do you know how many people sell supplements that they have no idea what's in those supplements?

• 30:11Rich Roll?

  Most, most, I have some familiarity with how that industry works. It's crazy.

• 30:15Speaker 01

  So, between that, between Ponzi scheme activity, between trying to sell an ebook for $400, which is just five blog posts you found on the internet and they're free, when you're trying to rush, you start cutting corners and you start doing wrong things to other people. And what you start doing is you start tarnishing your name and your leverage and your long-term capability. You're running a sprint versus a marathon because you're trying to make a million instead of 60,000.

• 30:43Rich Roll?

  But how do you reconcile that against this idea that you should dream big and hold high aspirations for yourself?

• 30:49Speaker 01

  I think you should. But you should understand that there's not a single fucking person on earth that ever made it big in four minutes.

• 30:57Speaker 01

  Like, got it?

• 30:59Rich Roll?

  Yeah, yeah, yeah.

• 30:59Speaker 01

  That's real. Like, Magic Johnson and Larry Bird took 1,000 free throws when they were nine years old every day before they made the league. Right? Like, Whitney Houston sang every day for 11 years.

• 31:11Rich Roll?

  Yeah, but Gary, who wants to do that? Who wants to do the work?

• 31:14Speaker 01

  Nobody.

• 31:14Rich Roll?

  Right?

• 31:14Speaker 01

  Why do you think there's so few people that win?

• 31:16Rich Roll?

  Right. So, is this the biggest misconception about you?

• 31:20Speaker 01

  Which is what?

• 31:21Rich Roll?

  The idea that...

• 31:24Speaker 01

  Because I got...

• 31:25Rich Roll?

  Let me couch it this way.

• 31:26Speaker 01

  Yeah.

• 31:26Rich Roll?

  Because I'm sure you get this question all the time.

• 31:28Speaker 01

  Please.

• 31:28Rich Roll?

  "Oh, it must be easy for you, Gary. Look at all the stuff that you got going on and you have this energy that I don't have and you don't understand my problems."

• 31:35Speaker 01

  Yes, but I think that's everybody about everything, right? Like, look, I think every... So, I don't think I'm very good-looking and I think that every good-looking person born is already in a better place than I am. Like, I secretly wish I was a hot chick. Like, I would so know how to navigate life with that.

• 31:52Rich Roll?

  You probably wouldn't have that battery then, though.

• 31:54Speaker 01

  Yeah, I mean, listen, the truth is, I used to think that, but it's amazing to me how many of my best investments are very attractive female entrepreneurs. Like, everybody's different, and you've got different circumstances that have happened in your life. Here's my punchline: I'm not too worried about people saying to me, "You don't get me, you had it easier." They don't know, right? And I don't blame them for not knowing. And the truth is, I don't care. And I don't care not because I don't care, I don't care because I now have lived my life for 10 years in public and I realize, poof! It's super hard to get people... I mean, the level of frustrat... Do you know the other night, I know I'm bouncing here, I went back and read the first comments of Daily V1 and 2, and everybody's like, "Oh!" And these are people that have been following me for seven years.

• 32:38Speaker 01

  "Oh, oh, that's what it takes?" And I'm like, "Motherfucker!" I've been pounding this message every day in every angle that I can think of, and it took this to get people to kind of, a little bit... Because there's a level of cynicism, and there's a little... There's a heavy level of self-deprecation and pity that is really riding... I mean, I'm watching this presidential, like, kind of race right now.

• 33:05Speaker 01

  Do you know I've never thought that the pres... Like, the level of "give a shit" that I have to who's gonna be the president is zero.

• 33:11Rich Roll?

  In the sense that...

• 33:12Speaker 01

  In the sense that I know they have no impact on my life.

• 33:14Rich Roll?

  Right, it's not gonna, it's not gonna determine how you're gonna live.

• 33:17Speaker 01

  That's right.

• 33:18Rich Roll?

  So, to abdicate that power to this, this person that's gonna hold this chair is, is to, is, is really to, almost on some level, play victimhood.

• 33:28Speaker 01

  At the highest levels, man.

• 33:38Speaker 01

  You know, I said something the other day on the AskGaryVee Show or somewhere, and somebody, three or four people have tweeted about it. I said it so quickly, I didn't even think about it, but it's something I've never said publicly, that it was so my truth, which was, "In my twenties, I spent every minute, not dating, not having fun, to get even with my parents, to get whole with them." I wanted to give back to them what they gave to me. And so I've lived my whole life where I don't want, I don't want to owe anybody anything. I don't want anybody to have any leverage on me. You know, I want to be whole. I want to over deliver. It's the reason I've become popular. I've become popular because it's hardwired in me to give you more than I ask in return.

• 34:19Rich Roll?

  Well, that's the principle behind jab, jab, jab, right?

• 34:23Speaker 01

  100%. And the big punchline of the right hook is if it doesn't land, be cool. You know, like it's so amazing to me how easy it is for me to reconcile when somebody doesn't come through for me, even though I've paid forward so much. I mean, things that should never happen. It's going on right now. Sending people emails that I've done a lot for in the last two years. I'm like, hey, man, my book's coming out. I really want to crush it. I want to sell all time highs. You know, I'm trying to be like nice and say things like, hey, and I'm going direct. This is one on one. This is not a bulk email. I'm like, hey, Rick, you know, da, da, da, da. How's Susan? Remember the other night? Glad that million dollar deal I made happen for you is going great. Like really pouring it on. Hey, I'd love for you to buy 80 books. It would mean a lot to me. Give them out at the office.

• 35:06Speaker 01

  80, by the way, is about a third of what I think on paper. If a judge and jury judged how much he should buy for what I've given.

• 35:12Rich Roll?

  Right.

• 35:13Speaker 01

  And then, and then they'll reply, hey, man, 80 is too tough, but like I'd love to get one or send me one and I'll review. I'll give you a tweet.

• 35:19Rich Roll?

  I love that. Send me one.

• 35:21Speaker 01

  So, you know, but it's stunning to me. And I've had three or four of them already happen last week because I'm really in it right now. And, and I'm like, cool. I get like, it's funny. Like I don't know what's going on in Rick's life. What if it looks good on paper, but Rick just made a bad business deal and his company is about to go out of business? What if Rick's mom just got diagnosed with cancer? What if Rick is super sad because his wife's cheating on him? What if Rick's super insecure and even though it's going good right now, he's. So I don't, I don't judge. I don't let anybody else have an impact on me. I don't consume anybody else's content. I haven't, I, I just do me. I put it out.

• 35:57Rich Roll?

  Hmm.

• 35:58Speaker 01

  I understand why everybody's feedback on me is pro, con, confused, pumped. The big thing that I love though, is that anybody that really digs or sticks around, I win. And I think that's the real testament to what I think of my tried and true, old school, lunch pail, put in the work, bring value, but most of all, the thing that I want for most people listening as I try to like bring a good interview here. You gotta know what you're good at. That's the game. If I had a potion. That could allow somebody to fundamentally become self-aware and know what they're good at, they would all win.

• 36:36Rich Roll?

  Most people don't know that, though, and most people are so disconnected from who they are that they're not even sure what it is that they would pursue if given the opportunity. You know what I mean? So, you know, there's a lot of, it's very, I think it's almost, it's not lazy, but it's very easy to talk about inspiration, like, oh, I'm inspired to do this, or this person inspires me. But I think most people don't know what to do with that inspiration. They don't know how to translate that into tangible action and creating a, you know, forward momentum and a, and a, and a solid trajectory for their life because they're not sure what that should look like for themselves.

• 37:16Speaker 01

  I get it, man.

• 37:17Rich Roll?

  And you can't answer that question for somebody else. They have to.

• 37:19Speaker 01

  And I want to, but I can't.

• 37:20Rich Roll?

  They have to know that themselves.

• 37:21Speaker 01

  It's really why I started Ask Gary Vee, because I wanted to get out of rah rah keynotes and just get into tangible, like, hoping that if I just gave them a blank study to ask me anything and I'll answer it. And I've been able to get much more tactical on that show and give them black and white things they can be doing. The problem is, the one thing I haven't been able to deploy at scale in pockets I have is patience. Patience is the secret potion, once you understand what to do. And I referred to it earlier, like, don't go into the quick buck.

• 37:49Rich Roll?

  Right.

• 37:50Speaker 01

  And, and I really get frustrated with the 18 to 30-year-olds. They have time. I can, I can feel a little bit better about Rick, 52-year-old Rick, who's in the cubicle right now, listening and has decided to make the jump, because Rick's feeling the pressure that he's 52. But these 19-year-olds, these 26-year-olds, that have all their life in front of them, they're not willing to eat shit for four years and work hard and punt it? That, to me, is like, fuck, man.

• 38:15Rich Roll?

  Well, that's the entitlement generation, you know what I mean?

• 38:18Speaker 01

  But you know what? I, I will say this, I have 600 millennials that work for me here at Vayner. I don't think they're any more entitled than the generation before them. I have, I'm 40, all my, I have nothing but entitled 40-year-old friends. Like, I think it's the human US thing.

• 38:34Rich Roll?

  Yeah, my experience with millennials and I'm around a lot of young people all the time is that I find them incredibly resourceful and I find them to care about important things that people in our generation just don't give a shit about.

• 38:47Speaker 01

  Yeah, they've been great about that. And, and, look, I mean, a lot of these kids are drinking $12 juice, going to Coachella, and taking Ubers all day, but they live in a studio apartment with no TV. Like, they're definitely living differently. But I don't think the cliche thing that everybody's got on millennials, like, hard work and things. I got 400 hard workers here that are bleeding out of their eyeballs. So I think, I think it's the context of the game they're playing within. I think that there's a real misnomer right now of what's really happening. We're living through the single biggest culture shift we've ever lived through. Like, the internet is a big deal. And it's only 20 years old. What you and I are doing right this second was inconceivable just a decade ago.

• 39:25Rich Roll?

  Absolutely. I mean, I think that it's easy to talk about it, but I don't think any of us can quite comprehend just how profound it is.

• 39:34Speaker 01

  100%. It's my biggest belief.

• 39:36Rich Roll?

  It's unbelievable, the tools that are at the behest of any single individual and the power that they carry to transform lives. It's unbelievable.

• 39:45Speaker 01

  I would have never, like, none of what's going on with me would have happened.

• 39:48Rich Roll?

  Myself as well.

• 39:49Speaker 01

  I would just be on my fourth liquor store in New York, Chicago. Like, I would just be building a bricks and mortar liquor store in the, listen, I'd still make a lot of money. Like, I would have figured that out. But I did figure that out before the internet.

• 40:03Rich Roll?

  But you wouldn't be making a cultural impact.

• 40:04Speaker 01

  No, I would not have the legacy that I'm gonna have. I'm not gonna have the amount of, the amount of people that are gonna show up to my funeral, which is really my North Star, is gonna be far greater, because I can reach so many more people at no cost. I mean, look, look, I mean, D-Rock's filming, you're recording, we're doing TV and radio right now.

• 40:21Rich Roll?

  At the same time.

• 40:22Speaker 01

  I mean, do you know how expensive that was 20 years ago? Like, studio time, like, it's just incredible what we can do now, reaching, I mean, there's people listening to this from all over the world. It's unbelievable.

• 40:37Rich Roll?

  Do you get frustrated when you

• 40:39Speaker 01

  Yes.

• 40:39Rich Roll?

  meet with these Fortune 500 companies and you're trying to explain to them that their ad buys to place, you know, giant bets on traditional television commercials is an outmoded use of resources and time. I mean, it seems obvious to me, but when you're, when you're butting up against, you know, that kind of infrastructure and tradition, it's gotta, it's gotta wear you down, I would imagine.

• 41:03Speaker 01

  Let me get a lot. I know a lot of your audience I've been watching doesn't cross over and has never heard of me before. So I'm going to go really fast so I can answer that question and give you guys a little context. My dad finally owns a liquor store. I launched one of the first e-commerce wine businesses in America called WineLibrary.com in 96. 98 to 2003 in a five-year window, I grew my dad's business from a three to a $60 million wine store. YouTube comes out. I decided it's going to be a big deal. I was right about e-commerce. People thought the internet was a fad. I was right about email marketing. People were doing catalogs. I was right about Google AdWords. People didn't know what it was. And so I started building up confidence that I was a great marketer, not just a great retailer. YouTube comes out, less than a year after YouTube

• 41:45Speaker 01

  came out, ironically 10 years ago yesterday of the recording of this, I start this show called Wine Library TV where I'm basically talking about wine. It becomes hugely successful. YouTube sells to Google for $2 billion. I go, holy crap. I can see the future. The next time I see something, I'm going to invest so I can make real money. That next thing happens four months later. It's called Twitter. I invest. I invest in Facebook. I invest in Tumblr. I get really smart. Clearly I made a lot of money with that. I amass a million followers on Twitter. I write a book called Crush It. That went super viral. A year on the New York Times Best Seller list. I end up being good at public speaking. So I start doing speeches. That becomes a big deal. Big brands start reaching out to me.

• 42:27Speaker 01

  Hey, you have 400,000 followers on Twitter. We're Pepsi. We have 50. 50, five zero, not 50,000. How do we, how do we use Twitter? What is Twitter? So I start a company called VaynerMedia, which is where we're sitting right now. My brother and I started six years ago. We are basically Mad Men 2016. We're an advertising agency, but we do the creative, the pictures and the videos. We do the ad placement and we do the strategy for the biggest brands in the world. GE, Pepsi, Fox Studios for Movies, Turner, you know, big, big brands, Unilever. And we are basically their marketing engine for Facebook, Twitter, Tumblr, Pinterest, Instagram, Snapchat.

• 43:08Speaker 01

  And so when R squared, as I like to call you in my brain, asks me that question, I'm living in a world where $8 billion a year is being spent on television and not a single person that's listening to this right now watches a single commercial. Meaning a commercial may play, but you're looking at your phone. You're not paying attention.

• 43:28Rich Roll?

  You either fast forward it using TiVo or you immediately stare at your phone.

• 43:33Speaker 01

  Correct.

• 43:33Rich Roll?

  Until the commercial's over.

• 43:34Speaker 01

  And so I like to tell people that I day trade attention. If you really want to sum me up, guys, if you want to get a feel of what my spiel is, I day trade attention. Meaning I'm always trying to pay attention to where the end consumer is spending his or her eyes and ears and I try to produce content on those platforms on the arbitrage of it being underpriced compared to what the market thinks. So that's why I'm obsessed with Snapchat because the market still fully doesn't understand how valuable it is. It's why podcasting was good two years ago. If you look at the people that popped up, they won because they bought podcasting when it was underpriced. I did it on Twitter, I did on email marketing, I did on Google AdWords, I did on YouTube, I did on Facebook. I did, I've done it a lot and that's where my wealth will come in.

• 44:18Speaker 01

  And so, yes, I do get very frustrated. I'm dealing with 42 to 60 year old executives who went to Kellogg or Chicago University, were taught what, you know, all this bullshit math from Nielsen's and RPGs and this, that and the other thing, GRPs, not RPGs, GRPs, gross rating points. Like there's no real data behind it.

• 44:39Rich Roll?

  Yeah, and trying to translate the importance of them focusing on Snapchat is

• 44:44Speaker 01

  It's hard.

• 44:44Rich Roll?

  gotta be a challenge.

• 44:45Speaker 01

  Now, now, Facebook's the one that makes me most frustrated because Facebook is television. Facebook is mass scale. Facebook is direct mail. I don't mind them not getting Snapchat yet, especially if you're selling 50 year olds on something, you don't need to be there. But if you're trying to sell a 13 to 25 year old anything in America today, Snapchat needs to be the core of your strategy.

• 45:06Rich Roll?

  Yeah, and you're extremely bullish on this and have come out hard and fast and strong all day long on shouting this message from the mountaintops. How is that being received?

• 45:16Speaker 01

  You know what's funny? Well, I think, you know, I've been taken aback. What really happened this time around was I haven't shouted this loud about something in a long time. I've been surprised how many people have like, all the marketing people are jumping on board on Snapchat pretty quickly. A lot of people making jokes that about my impact on it. But what I didn't realize was, you know, all these people that have been influenced by me are now big. They have their own podcasts. They have their own shows. They have big social networks. So they get influenced by me. They've seen it. They've seen this rodeo before. They're shouting out it. So it's a long tail effect. But the truth is, I'm not worried about my impact on the market or how it's being received. I just want to be historically correct.

• 45:52Rich Roll?

  Right.

• 45:53Speaker 01

  I'm not worried about 2016. I'm worried about 2020, when everybody looks back and says, "Ugh, Gary was the first guy that really pushed me to get serious about this." And I'm, by the way, we're, we're two months into this, and I probably get one to two tweets or Facebook messages already saying, "You're the one that pushed me to Snapchat. It's already the most important platform for me. I've already made a sale," or this, that, the other thing. And so it's been fun to watch.

• 46:18Rich Roll?

  That's cool. Is this part of the new book? Or was the new book already written by the time this epiphany occurred to you?

• 46:26Speaker 01

  I'll say it here on the record forever. I will never shout about something like I did with Twitter, or like I did with Snapchat, for any other motive than being historically correct, because that's where I make my most money. It's not about an investment I make. It's not about my show. It's not about a book coming out. It's strictly because I believe it. And I know that in four years, when everybody ties back the loose ends, they go, "He was already again, once again." That's my narrative. The only thing I want is for everybody to think, and know, and to be proven to be true, that I see things just a little bit sooner than most. I figure out how to use them a little bit better than most and that I'm a very valuable person to pay attention to because of that.

• 47:06Rich Roll?

  It's interesting how these tectonic plates shift over time, right? Because for a long time, I was all about Twitter and now I've noticed, and I don't know what your experience has been, but the engagement level that I get on Twitter is a small fraction of what it used to be, even though my follower count is higher.

• 47:23Speaker 01

  That's right.

• 47:24Rich Roll?

  And I've gone back to Facebook where I get much more engagement and I thought that was a relic, but now I'm much more invested in that as a way of communicating with people.

• 47:32Speaker 01

  Because I day trade attention, I am just constantly looking at it. You know, I've been yelling about, you know, Snapchat, the thing I was yelling about last year and the year before was Facebook. And, you know, if you go watch the first 150 episodes of the Ask Gary Vee Show, it's a Facebook propaganda machine, mainly because it was working and it worked. And it makes sense to me to hear you say that. If I would have done Ask Gary Vee in 2009 and 10, it would have been a Twitter propaganda machine. So, yeah, I'm watching it on a daily basis. And by the way, the stuff shifts fast. Like, it can move on you quickly.

• 48:09Rich Roll?

  Yeah, yeah, yeah. I mean, I just feel like Twitter, everyone's talking and no one's listening.

• 48:13Speaker 01

  That's right.

• 48:14Rich Roll?

  You know?

• 48:15Speaker 01

  Which is why I'm listening and that's where I'm getting value out of Twitter right now. I've really shifted back to 2007 behavior on Twitter. What I mean by that is I'm basically now going, I went four years only looking at my mentions and engaging with people and then putting out stuff. I've gone back to following a lot of people, watching what they're talking about and then engaging on what they talk about to get them to pay attention to me again.

• 48:38Rich Roll?

  Yeah, I think that's a big distinction between you and a lot of other people that have gigantic followings, because I think the presumption would be you're a broadcaster, but you're really not. You're far more interactive than most people that have over a million followers. I mean, you're known for responding to tons of people, even sending them video responses. You love doing that. You sent me one of those one time. And it's great because it makes people feel like, oh, man, he actually like read my thing and he took a moment to respond and the impact of that is tremendous.

• 49:10Speaker 01

  It's a triple win. Number one... I don't follow anybody else. So I'm following people to make my decisions about where marketing is going. So I need it. The reason I'm so good at listening is because I need the listening. I value the listening. I don't want to read ad age or read one of the other 50 authors in my space to make my decisions because I feel like I'd be slow. For me to be fast, remember, it's really interesting how I positioned what I just said earlier. Just a little faster and everybody just a little bit better. That's enough for me to be much more valuable. I want the most important tastemakers, the top 50 people on the, you know how much pride I get when I look at the top 50 business podcasts and I know, not I guess, I know

• 49:51Speaker 01

  how much all of those people follow me for some of their decisions and their tactics. I mean, it's super, you know, it's super, it's super cool and it's super doc, you know, if I ever got into a debate of its truth, you, it's all documented. I'm like, look, here's what I did on Snapchat. Oh, look, here's what this person, this person, this person, this person did the following month. Like it's like, there is no mention.

• 50:13Rich Roll?

  They're just following you in lockstep.

• 50:14Speaker 01

  That's right.

• 50:15Rich Roll?

  Yeah.

• 50:15Speaker 01

  And so that's important to me. That's leverage, that's power, that's, that's how I see myself. And I think the reason I'm able to do that is I'm watching people, not pundits. So as I'm following everybody and I'm watching what they're saying, I'm watching what they're saying about me. Now I'm starting to actually more than ever look at what they're saying about other people and other issues. That gives me time to reply very quickly. I know it matters to people because effort is what matters more than anything. And so if you make a video, they're like, woof, like they can, they, first of all, too many people outsource their social. So a lot of people, if they get a tweet from somebody famous, they're not sure if that's the person's assistant or it's them. So one, I like to prove that it's always been me and always will be me. That's number one. Number two, yeah, I think that makes them care more. I really do.

• 51:00Speaker 01

  I think, I think in a world where they could listen to anybody, the person that listens to them and, and adjusts to them is more valuable to them than the person that posts something through their assistant, never looks at it and it's just a broadcasting mechanism.

• 51:13Rich Roll?

  Well, authenticity is the most important thing, right? And the moment that you, you lose that connection with authenticity, you lose, you lose the whole ballgame, I think. And I don't think enough people appreciate that. Or respect that fact, or understand that the millennials, all these people that are working in your office, have the most highly attuned antenna and radar for this kind of thing. And they can sniff out bullshit from 10,000 miles away. And that must inform how you message these companies about how they message their customer base.

• 51:48Speaker 01

  Hundred percent. I mean, it's, yes. I mean, I don't know, you know, you led, you led, led me to the well. The answer is yes. And I think the other thing that happens, and I wonder for people that are listening that have gotten some micro notoriety, which is what I think I have, maybe a little bit more than others, but still, I'm not Beyonce, right? I'm taking one to three selfies a day in public, not 700.

• 52:09Rich Roll?

  Well, when Beyonce goes for it, she goes for it big. It's like a NSA data dump when she hits Instagram.

• 52:16Speaker 01

  I think, I think that what's most fun for me is that I get extra credit now for just being who I always was. When I'm like, running through the streets and somebody can see I'm busy, and they're like, hey, I love your show. And I stop and I go, what's your name? Shake their hand, take a selfie. They're like, oh my God, you're such a nice guy. And I always tell my friends, or like, you know, I went out to dinner the other day with my friends, and it was an exceptionally good day for my brand, which, by the way, for my ego is the greatest feeling of all time. Going out with friends, having four people take a selfie with you. They're like, whoa, you're really, you know, wow, right? And I'm like, yeah, it's going pretty well. And what, what I told them after the fourth one, I was like, look, and they saw how people reacted. And I said, you know what's most interesting? I think that notoriety, fame, money, it only exaggerates who you actually

• 53:01Speaker 01

  are. You know, like, I think that it's funny for me to see people be surprised that I want to be nice, or that I care. It's so sad that that's the cynicism around fame or wealth. And I actually think those things just, Ice Cube, I was at a Knicks game, he's sending a couple over, I'm super pumped, I love rap, you know, Compton just came out. He was pumped to take all those selfies.

• 53:27Rich Roll?

  Uh huh.

• 53:28Speaker 01

  It's just who he is, right?

• 53:29Rich Roll?

  Right.

• 53:30Speaker 01

  Like, and so I just think that, I think that it's fun when you start winning a little bit and you get extra credit for things that you shouldn't get credit for.

• 53:38Rich Roll?

  Just being who you are. I mean, you know, the, the, the transparency of the internet is sort of dispensing with that notion of what you're like when the camera's on versus what you're like with the camera's off.

• 53:54Speaker 01

  Well, I don't know about that. That's actually the other thing for me. I've been stunned watching how good people are of creating the PR'd version of themselves on social versus who they actually are.

• 54:05Rich Roll?

  But don't you think those millennials can sniff that?

• 54:07Speaker 01

  Sometimes, not as much as I'd like. I mean, yes, and you know, with, with brands, yes. But something happens when it's a celebrity or a micro-celebrity that I think makes them hope or want, you know?

• 54:21Rich Roll?

  But they're not actually like that. Who is, who is killing it? Like, when you look at, when you kind of canvas, yeah.

• 54:27Speaker 01

  Taylor Swift.

• 54:28Rich Roll?

  Why?

• 54:29Speaker 01

  Cause she's playing the thank you economy. She knows that surprise and delight and these micro-moments carry more weight. She knows when she stops by a fan's house out of nowhere, that she's not just affecting that fan, that she's gonna get press around it and she's affecting 10 million people's point of view on her. And by the way, that's how I think about it. When I reply to you, I know that nine other people that follow both of us saw it and they're affected by it.

• 54:54Rich Roll?

  And how much of that is calculated on her part or is just a natural outgrowth of who she is?

• 55:00Speaker 01

  The reason I think she's like that is the same reason for me. It's not that it's calculated, it's just that I'm aware. Like, I'm not, like, there's a lot of things that I'm aware of or I could be calculative that I don't do because it doesn't come natural to me. So I just think, I think, I don't know her well enough, but I know a lot of people that know her well enough and that I know very well, that make me feel comfortable that she just got lucky. She also is a nice person who's hyper-talented, who understands the benefit of it, cause she's ambitious as fuck, but she genuinely likes to do it too. Like, I genuinely love everybody who's, like-

• 55:34Speaker 01

  Can we just take a quick step back?

• 55:36Rich Roll?

  Yeah.

• 55:36Speaker 01

  What human, unless you, and listen, some are introverts, some don't like inner, but if you like being around people as a precursor, who doesn't love somebody desperately wanting to spend a minute with you? Like, it's intoxicating. Like, when I walk through an airport and somebody makes eyes on me, and I can tell they know, and like, and they're just trying to be, maybe they'll give a head, it's like the greatest high.

• 56:01Rich Roll?

  Mm-hmm.

• 56:02Speaker 01

  Like, you're doing something that people appreciate, and they like you so much, they want to acknowledge you, or even stop and say hello. Or, the thousands of times now in my career, people have tweeted, like, "Just saw Gary V at the Shake Shack, I wish I should have said hello," or, "It was cool to see him." And I reply, "Yeah."

• 56:18Rich Roll?

  Why didn't you say hello?

• 56:19Speaker 01

  Yeah.

• 56:20Rich Roll?

  Right.

• 56:21Speaker 01

  And so, you know, yeah, it's super nice, I don't know, I don't know what human wouldn't love it.

• 56:25Rich Roll?

  No, it's amazing. So, who out there, conversely, do you wish you could bring in here and wring their neck and say, "Why are you doing this? If you just did this, everything would be so much better for you."

• 56:37Speaker 01

  There's a ton of people who are my contemporaries, who I would call my acquaintances more than my friends, who are selling bullshit, and it bothers me.

• 56:45Rich Roll?

  Hmm.

• 56:46Speaker 01

  And I don't want to, you know, I'm not going to put them on blast here, but I would tell you, a stunning percentage of the people that have big followings on social, who are in the business self-help, you know, are really pushing the envelope further than I'm comfortable with, of trying to monetize. And I've started talking about, like, look, paying twenty or thirty thousand dollars a month or a year to be in a mastermind is intriguing to me, when there's so much free... And look, do I, look, do I think I could charge fifty thousand and have a group of people that I consulted and make it worth their while? I do. And so, I'm not sitting in those groups, and I'm not going to those offsites, and I'm not seeing how they're interacting, so I don't know.

• 57:28Speaker 01

  Which is why, the biggest reason I'm not willing to put anybody really on blast, is I'd have to take the time to fully know everything they're doing. To feel comfortable.

• 57:37Rich Roll?

  No, I get it. And I'd love to camp out here for a minute.

• 57:39Speaker 01

  Please.

• 57:39Rich Roll?

  Because this is something that affects me personally.

• 57:41Speaker 01

  Okay.

• 57:42Rich Roll?

  Because as somebody who's a podcaster and, and an author and making videos and all this kind of stuff, uh, you know, I'm always paying attention to what other people are doing.

• 57:52Speaker 01

  Sure.

• 57:52Rich Roll?

  And I've noticed this like ascension of these mastermind groups where people are paying a lot of money to be part of these, this tribe.

• 58:01Speaker 01

  Yep.

• 58:01Rich Roll?

  That then all supports each other and, and something inherently cool about that. Like they're getting together and they're, and they're, it's a support network for each other. But at the same time, I also see like work product out there that I question the quality level of that's being priced in the market at an extremely high price and like very hyped. And I see all these marketing tools being utilized through like, you know, incessant emails and these like, you get stuck in this email chain that you can never escape of until you, you like get that hard sell, you know, buy here button and all of that kind of stuff that's going on on the internet that I've really stayed away from, you know, because it, it just doesn't feel right to me.

• 58:44Rich Roll?

  And I could probably like growth hack what I'm doing by participating in that, but I just, I can't, like on a spiritual level, like I just, I can't do it.

• 58:53Speaker 01

  I don't think anybody, because I think I'm as good of a marketer as anybody, is gonna make an ebook worth 900 bucks.

• 59:03Rich Roll?

  There's no way.

• 59:04Speaker 01

  There's no way. There's too much good free, like if you just listen to every podcast and the top 25 business podcasts, you'll get more value than any one of those things. So it's hard.

• 59:15Rich Roll?

  But there's something human in that, that they think like, because it's so expensive, people want to spend that money.

• 59:21Speaker 01

  Well, now you're getting to the thing that probably frustrates me the most, which is.

• 59:27Speaker 01

  Literally, right now, as we speak, somebody just bought a $400 Snapchat guide ebook that is completely out of the words of my mouth in the last 50 episodes of Ask Gary Vee, Daily Vee, and my Snapchat, that somebody else took, repackaged, sold for 400 bucks, and I'm watching too, and are leaving comments like, "This is so great," and then coming to my, and they're fans of both, and then saying, "Gary, why don't you give any details?" And it's, if you really want to get upset about it, you could get really sad for the current state of the marketplace, because you start realizing the reason so many of these people are able to pull it off is because the end consumer is looking for a dream.

• 1:00:10Speaker 01

  Nobody's gonna subscribe to me that's looking for a shortcut, because I call them out too much, and I talk too much about hard work, and I become exhausting on, like, it's already happening. We're only 15 episodes into Daily Vee, and already, the comments start, "Hey, man, enough already of talking about hard work. We get it. You work harder than us. Fuck you." And I'm like, "You so don't get it." I'm like, "You just don't want to, you want to hear, 'I'm gonna give you a 10-month program, and you're gonna make a million dollars, and you're gonna get 40 people underneath your tree, and you're gonna fucking sit on the beach, and all these other people are gonna work, and you're gonna make a million bucks because you manipulated them to work and not you.'" I mean, it's fucking ludicrous.

• 1:00:54Rich Roll?

  People want good news about their bad habits. They want to believe that if they spend that money, they will be given the answer and the shortcut, and that applies to, you know, whether it's your career or entrepreneurship, or whether it's diet, that you can eat X, Y, and Z and still lose all the weight that you want to lose and not have to work out. You know, as human beings, we're just, we're so predictable that way.

• 1:01:20Speaker 01

  100%.

• 1:01:20Rich Roll?

  And it's so easy to play that core.

• 1:01:22Speaker 01

  The lottery works for a reason.

• 1:01:24Rich Roll?

  Yeah, exactly, right?

• 1:01:26Speaker 01

  I mean, I look at most of the people in our space as similar to the lottery. And I get it. And you know what? What's funny is I don't begrudge them or the individuals that follow. I get mad at the few, the five handfuls that I can think of right now, that I've seen comment on both. And I'm just like, man, you've lost. You'll never make money. You're gonna keep taking your hard-earned money that you're miserable making and deploying it down wells that have no shot. And you're gonna look up in three years and be like, what the hell happened? The people that win with my content are the ones who suck out everything I say for a year or two, then put their head down for 18 hours a day,

• 1:02:11Speaker 01

  and then pop back up three years later and start needing more content from me because they've taken the first step. And now they're looking how to get from 100,000 to a million because they've realized it's tactical. It's work ethic. It's those things. And it's been interesting to watch for me from afar, the people that win and the people that lose based on my content and the rest of the market's content.

• 1:02:33Rich Roll?

  Well, I think there's, there's long-term success versus, you know, short-term success with flameouts, right? So my whole thing is whatever I'm doing, whether it's a podcast or a book or a blog post or a video, I'm just trying to make the best thing that I can and put it out there. And there's probably some, some tools and tactics that I could employ to attract more attention to that. But I'm in it for the long run, man, you know? And I'm not willing to alienate my audience by playing to them too hard to try to attract that attention.

• 1:03:07Speaker 01

  It also depends on-

• 1:03:08Rich Roll?

  And I have a belief that over time, I will congregate the tribe that is interested in what I have to say.

• 1:03:16Speaker 01

  It also matters what kind of audience you want.

• 1:03:20Speaker 01

  Like, I want to be proud of the people that follow me and spew my spiel. You know, like, you are who you like, you know, hang out with. I think the audience makeup is quite important.

• 1:03:33Rich Roll?

  I mean, the, the kind of person that's attracted to what you have to say.

• 1:03:37Speaker 01

  Look, there's a different, there's a reason that with my book coming out in a little bit, or out now, depending on when you hear this, that I'm gonna be on Fox and CNN and CNBC and Inc. and Fast Company and Fortune 500 CEOs that are active, not, like, are quoting me and like, there's a very big difference between who buys my stuff than what a lot of the contemporaries look like. And I'm proud of that. So maybe I won't sell as many or, you know, make as much short-term money, but I laugh when people like debate like how much money I make versus somebody else that looks like me that's playing a short-term game, because I'm like, you're just judging today. I'm like, let's talk in 2020.

• 1:04:18Rich Roll?

  Yeah, a year later, two years later, three years later, who's still buying your book?

• 1:04:22Speaker 01

  Not to mention, VaynerMedia, which I've built from scratch with my brother, is a three to $400 million valued company. Like, in parallel to building my brand, I've built $100 million revenue that trades at 3X revenue in the agency world, business. Like, my whole life isn't being Gary Vee. I'm much more Gary Vaynerchuk, CEO of VaynerMedia than I am Gary Vee.

• 1:04:47Rich Roll?

  And what's so interesting about that is that you've really exploited what is truly a niche in other advertising agencies, their social media department.

• 1:04:57Speaker 01

  Yes.

• 1:04:57Rich Roll?

  And you understood, no, that is, that's the whole thing.

• 1:05:00Speaker 01

  Because social media is a slang term for the current state of the internet. Like, the mobile device is the most important device that delivers the internet now, and half of our activity on it is social networks. It's the most important thing. And so, the word seems small, because it's new, and there's a lot of hucksters in it. But it's just, again, I don't get caught up in the word. Like, I'm marketing on the internet. You know, the internet that matters now, Facebook, Snapchat, like, nobody's going to forums. I mean, there are, and plenty of you are on forums, that's fine, but the mass attention is on these platforms, and you have to know how to market on them.

• 1:05:46Rich Roll?

  What do you think is the biggest mistake that either individuals or brands are making in their relationship to social?

• 1:05:52Speaker 01

  That they don't understand the context of each individual platform and thus they don't know how to act in the room, right? So, think about not ever going to a meditation retreat and showing up like a business guy and passing around business cards.

• 1:06:08Rich Roll?

  Right, right.

• 1:06:09Speaker 01

  Got it?

• 1:06:10Rich Roll?

  Uh huh.

• 1:06:11Speaker 01

  Or being a hippie dippy and walking into a Fortune 50 boardroom and try, like, so many of my friends are like, Gary, I want to do what you do with VaynerMedia. I'm like, cool, go try to walk in with that $80 ebook or your fucking white labeled supplements into fucking Pepsi.

• 1:06:28Rich Roll?

  Mm-hmm.

• 1:06:29Speaker 01

  You get laughed at in a room in one second. And so, you know, it's understanding the context and that's the same thing that happens. If you don't know how to market or produce content on Snapchat versus Facebook versus Instagram, well then you're gonna lose. And so, they're all different.

• 1:06:45Rich Roll?

  Right, this idea that they're all the same is crazy.

• 1:06:47Speaker 01

  It's crazy.

• 1:06:48Rich Roll?

  Yeah, they all have their own etiquette and rulebook.

• 1:06:50Speaker 01

  That's right. And think of it as a person. Like, you're gonna act very differently in this room right now, we're doing a professional thing, than if me and you go to Hawaii for the weekend to hang out, or the way you would act with your best friend on a trip to Iceland for a week, or the way you're gonna take your spouse out to dinner. So like, everybody's got a lot of dimensions in their personality, but they deploy it based on the room they're in.

• 1:07:15Rich Roll?

  Mm-hmm.

• 1:07:16Speaker 01

  And I think the thing that I've done really well is I've understood the context of each platform, and then I know how to make the pictures and the videos that work on that platform, because I respect the psychology of the person on the other end of what they may be thinking when they're in there. When you're LinkedIn, you're thinking business, but when you're on Facebook, you might be hanging out with your college friends or keeping up with your life. And on Instagram, you might be looking for soft porn or inspiration, right? Or, you know, or Snapchat, you're just looking to be entertained like television.

• 1:07:48Rich Roll?

  So what, where's it going? Like, what's next? What's beyond the horizon?

• 1:07:53Speaker 01

  I think, I think we continue with these, over the next 10 years, I think we see two to three more Snapchat, Instagrams pop up that we can't think of, which is great, because I'll be first, and I'll be best. You'll see certain things, does Twitter become MySpace, maybe? I think you can see one or two of these, Tumblr and Twitter were much more important three years ago. So we'll see one or two fall away. And then I think we'll go into a VR world, a decade from now. So I think 10 to-

• 1:08:22Rich Roll?

  That's inevitable.

• 1:08:23Speaker 01

  Yeah, I think so.

• 1:08:23Rich Roll?

  That's for sure.

• 1:08:24Speaker 01

  So I think we're gonna be wearing contact lenses, not headsets, 10 to 20 years from now. And this interview, we would be both in our home, instead of at VaynerMedia right now, and we would really feel like we're here together.

• 1:08:35Rich Roll?

  Right. That's just a mind blower.

• 1:08:37Speaker 01

  It's a mind blower, because then you start, you know, one of the biggest reasons I've been thinking about buying real estate in San Diego, is I'm like, hmm. When I'm 60 in 20 years, I really do think everybody's gonna be able to do everything they want, where they are. And so then, why not be in nice weather places, when you don't put your contact, when you're living your real life, or your fake life, which is your real life?

• 1:09:00Rich Roll?

  Right. What is real?

• 1:09:01Speaker 01

  Well, no, it's really, it's really intense, and I know we're getting zen here, everybody. Let me get out of the interview for a second. I understand that this sounds insane, but let me paint you a picture. If you told people in 1980, the way we live today, actually, let's go 1990, because I wanna soften the gap. 25 years, if you in 1990, told people about smartphones, and Uber, and Airbnb, and Amazon.com, and same-day delivery, and social network, and Tinder, and online dating, and like, all, you know, their head would explode.

• 1:09:33Rich Roll?

  No, I remember when-

• 1:09:34Speaker 01

  It's 25 years ago!

• 1:09:35Rich Roll?

  It was even sooner than that. I mean, even when everybody had their cool little Nokia phone, it was like, everything's gonna be mobile, and I remember thinking, like, how is that, how is that gonna work? Like, I don't wanna do everything on my phone.

• 1:09:48Speaker 01

  And now, I'm traveling, for, this is the first year, 2016, I'm traveling without my laptop, I'm doing everything on my phone. And like, my laptop was the extension of me, and that was progressive, traveling with a laptop.

• 1:09:59Rich Roll?

  Right.

• 1:10:01Speaker 01

  Yeah, I think, I think augmented reality VR is going to blow people's minds. I think video games and entertainment, movies, video games gets affected first, but I can see business right behind it. It's gonna be very interesting. Porn, I think the porn industry, which always innovates, I know this is a silly topic, but you know, the porn industry is-

• 1:10:22Rich Roll?

  Well, virtual reality in porn is-

• 1:10:24Speaker 01

  You gotta understand, your brain thinks it's 98% real.

• 1:10:27Rich Roll?

  And so I assume you've been, been, you've been playing around with all the prototypes and everything?

• 1:10:32Speaker 01

  Yes, all of them. And, and it's the first time that I feel the way I felt about the internet, which is like, okay, this is gonna change the world, but I do think it's gonna take 10 to 20 years.

• 1:10:43Rich Roll?

  Yeah, yeah, yeah. So other than your hard work ethic and your Energizer Bunny disposition, you know, what do you attribute, what sort of characteristics about who you are, do you attribute your success to? Like, what is it about you that's allowed you to kind of grow and thrive?

• 1:11:00Speaker 01

  Empathy.

• 1:11:02Rich Roll?

  Interesting.

• 1:11:03Speaker 01

  I really know what the other person's thinking, and I know what they want, and I reverse engineer it.

• 1:11:10Rich Roll?

  That's a great answer, man. I wasn't expecting that one.

• 1:11:12Speaker 01

  Good one, right?

• 1:11:13Rich Roll?

  Yeah, that's good.

• 1:11:14Speaker 01

  It's probably my biggest secret sauce.

• 1:11:15Rich Roll?

  And, and what do you think holds most people back?

• 1:11:18Speaker 01

  In general?

• 1:11:19Rich Roll?

  Yeah.

• 1:11:20Speaker 01

  Self-esteem. They just don't think they're worth it. They don't think they're good enough, and I think their parents fucked them up. Which pisses me. I feel lucky. A lot of my friends get mad when I talk about luck. They're like, Gary, you've been working your face off since 14. You know, a lot of my friends know me since I was 14. They know that I've been gone since 14. I have friends who know that I've been gone since 14, which was the year where I lost my weekends and my vacations because my dad made me work at the liquor store. And they're like, how can you say luck? You've been fucking doing this for 25 years. We were still kids. Like, we were going to camp and playing, and you were gone. You've been, this is your destiny. You put in the work. Don't talk about luck. Well, I can't talk about luck. My parents perfectly parented me, both in the hard work, both,

• 1:12:05Speaker 01

  both, my mom drilled my self-esteem, meaning like- Brainwashed me to think I was the best. Then I got lucky that nothing tragic happened. What if my mom died in a car accident? Then I would have never had like, you know, it's part of the equation. But I think the number one thing that holds people back is self-esteem. They don't think they're good enough, thus they can't take the first step.

• 1:12:23Rich Roll?

  Mm hmm. Yeah, and you can't solve that problem for them.

• 1:12:26Speaker 01

  No, but I can talk about it, which may lead them to go to therapy, which may lead them to do the thing. You know, one of the weird things that I'm doing that nobody talks about, that I do think ends up being a big part of my legacy. One of the things I'm trying to do with Daily V and put myself out there is I want to be the self-esteem for them. Now, I don't want to do it in a fake way. So I think most people are selling them fake shit. So they're not really building self-esteem. They're tricking them so that they can make money. What I'm trying to do is I'm saying stuff they don't want to hear. Work every day, don't have fun. You know, if that's, you know, if it is fun, cool, do that. But you're not going to make as much. I'm talking about real stuff. But then I'm trying to rah rah and cheer like, I would love, you know, D-Rock, I know you're here.

• 1:13:12Speaker 01

  Like, you would be stunned by how many of the kids that work here have fundamentally changed the way their confidence is because I've deployed it on them. D-Rock, D-Rock is a hu- I mean, I know him. He's sitting right here. I mean, I'm, I know we're not visual right now. I know we're audio. I think you're dramatically more confident than you were before you started with me.

• 1:13:32Rich Roll?

  Is that because you are empowering them to step into a level of responsibility? That's sort of just outside their reach and allowing them to grow into it.

• 1:13:40Speaker 01

  That, I'm doing what my mom did. I'm telling them they're great in the beginning. There's nothing wrong with that. If they suck, I'll tell them you're not as great as you thought like, but I'm starting with positive. Um, I'm, I'm taking most of the pressure out. So one of the things I do a lot is make sure people underneath me don't feel losses. And then I do. So I don't want to give eighth place trophies.

• 1:14:00Rich Roll?

  Right.

• 1:14:01Speaker 01

  There's consequences, but.

• 1:14:03Rich Roll?

  I mean, that's a, that's a.

• 1:14:04Speaker 01

  It's a fine balance.

• 1:14:04Rich Roll?

  It's a management style though, right? Like you're saying, if I'm criticizing you, it's not because I don't think you can do it. It's quite the opposite. I think you can do this. Let's see how you can step into it and give people a wide berth to take that mantle and expand their level of responsibility.

• 1:14:20Speaker 01

  I think most parents that I watch now suck. And here's why. And this is tough for me to say. I'm not saying that with like audacity, guys. I'm watching parents and I'm watching a lot of parents. Parents. A, reward things that don't deserve to be rewarding. They think they're checking the box there. And then B, secretly are undermining their kids and telling them that they can't do it.

• 1:14:39Rich Roll?

  Mm-hmm.

• 1:14:40Speaker 01

  It's so fascinating. I literally want to be the reverse of what's politically correct right now. I want my kids to know that I believe in them the most, but if they come in third place, they come in third place. Xander is now almost four years old. He still has not scored a single basket on me in basketball. The kid has got a complex right now because he thinks every shot's gonna be blocked. And they'll all be blocked until he makes it. AJ didn't score on me. He's my brother, 11 years younger than me, my partner in VaynerMedia. He didn't score on me until 7th grade. But when he beat me, when he was 19 or 18 or 16, I can't remember when he beat me. When he beat me, he knew.

• 1:15:14Rich Roll?

  Mm-hmm.

• 1:15:15Speaker 01

  You know?

• 1:15:15Rich Roll?

  Right, right, right. Cool. What would you, uh, what would you tell yourself at 20? Like, what do you, what do you know now that you wish you had known when you were younger?

• 1:15:24Speaker 01

  I probably could have had a little more fun, just a little. I didn't need to completely stop hooking up with chicks and going on. I could have easily went on one vacation with my college buddies for a weekend. I probably went a little too extreme, though the truth is, I'm not capable of regretting it because, I don't know. Like, it's all so good, so I, so that would probably be it. Everything else has gone pretty good. I, I do think five to 10 days a year that I worked could have been deployed against some fun. And I've used that learning with my kids now. Like, I'm taking six, seven weeks vacation a year, which is unheard of for me, compared to two, just a couple of years ago, because I don't want to repeat that mistake.

• 1:16:07Rich Roll?

  And on top of that, I guess it's been 18 months since you made this very conscious decision to prioritize your health and your diet. Uh, and I think perhaps the old Gary would have thought, "Well, that's a waste of time. That's time away from the office."

• 1:16:21Speaker 01

  Yes.

• 1:16:21Rich Roll?

  So, so how has that impacted productivity? I mean, you look great. You look a lot better.

• 1:16:26Speaker 01

  I look a lot better. I'm clearly better. It hasn't in the short term. I'm sure at 50, 60, 70, 80, I'll feel the benefits of this. I don't want to lie and say I have more energy. I always had a shitload of energy. I think my natural testosterone or whatever levels are so through the roof. It's why I never did drugs. It's why I've never, like, I'm crazy. Like, I've never drank a Red Bull for real. Like, I'm, it's funny, when I show up, like, I'm sure right now people are listening and they're like, "Boy, what'd you have?"

• 1:16:51Rich Roll?

  This guy has 12 Red Bulls in the belly right now.

• 1:16:53Speaker 01

  That's right. And so I got lucky that way, no question, DNA-wise. Um, but what it's definitely taught me... And it's actually, this is very deep for me. This is the first second I've gotten emotional in this episode. This is really cool for me to say. I'm really proud of this. And this is the number one thing my mom's proud about in my life. And I've done a lot of good things. She's proud about this health thing because she knows me better than anybody. It's the first time I've done something that didn't come easy to me successfully.

• 1:17:22Speaker 01

  And it's very empowering. You know, a lot of people that listen to me, this is probably the moment a lot of you that listen to everything I do have been waiting for because it's the first really, like, there's a couple nuggets in here that I've dropped for like the hardest who've listened to everything.

• 1:17:35Speaker 01

  It's the first time, and by the way, I will never not have a full-time trainer. So a lot of people see I look better, I'm better, this and that. Mike's leaving in July and they're like, "So you got it, right?" And I'm like, "No, no, there's gonna be a next person." And they're like, "What?" And I'm like, "Never again because I know I'll go back." Because I've figured out the system that allows me to win this. But it's been, what it's taught me more than anything is there's other things I can do in my life that don't come natural to me. Because I'm always saying, "Bet on your strengths, punt your weaknesses." You know, health is not a weakness you can punt. You'll just die earlier.

• 1:18:09Rich Roll?

  No, that's, that's very cool. That's super interesting because the penchant for hard work and the dedication and the focus and the energy, all of that is very natural to you.

• 1:18:19Speaker 01

  Yes.

• 1:18:19Rich Roll?

  You're not, you don't have to will yourself into that state. But the idea of tackling fitness and health and diet and all these things that you've battled for so long, that's outside your comfort zone.

• 1:18:30Speaker 01

  And now I believe that all the bullshit I spew about hard work in business can be adopted by people that it doesn't come natural to them as soon as they go from tactic to religion. I went from tactic to religion. Meaning, for eight years since I turned 30, I've had four different trainers. That was my tactic. "I'll get a personal trainer." But then I would call out, I wouldn't do it, I gave up, I didn't eat right, and I made a religious shift. "I'm gonna do this and I'm gonna look at everything I do and I'm gonna come up with a new system." Everybody who's listening right now who's had a failed entrepreneurial venture or it's not going as well, your behavior's broken. You've not done the right thing. That means you either have to work more, work smarter, sell something instead of being a consultant. You've got to figure it out, but it has to be a drastic change, not a little bit more

• 1:19:15Speaker 01

  of the same.

• 1:19:16Rich Roll?

  Yeah, I like to say you only have to change one thing, everything.

• 1:19:20Speaker 01

  That's right.

• 1:19:21Rich Roll?

  To change your lifestyle.

• 1:19:22Speaker 01

  It's a mindset.

• 1:19:22Rich Roll?

  It's not a diet, it's a lifestyle.

• 1:19:24Speaker 01

  That's right.

• 1:19:24Rich Roll?

  It's a mindset, it's the way that you're living your life on a moment-to-moment basis. I know we gotta wrap it up.

• 1:19:29Speaker 01

  Yep, no worries.

• 1:19:30Rich Roll?

  You gotta jump, but I can't let you out of here without telling me a little bit about the new book, man. Ask Gary Vee.

• 1:19:36Speaker 01

  It's my fourth business book. It's, in a lot of ways, it's similar to Crush It. I wanted to make something that was a little more inspirational. I push against that part of my life because it goes to a lot of the themes we talked about tonight. Inspiration leads to bullshit a lot of times. And so I try to remind people, I'm a businessman, I'm an operator, I build things, not just rah rah. But I did have more of it because, you know, I was affected. I'm getting still 20 emails, 50 emails a month. Just read Crush It, it's six years later. You've helped me, I'm better, something good has happened. I said, you know what, I can't run away from that. But it's the most 360 look into my brain. Like anybody, whether they're starting or they've got something successful, anybody can read it and get their $20 value out of it. And that was my biggest goal.

• 1:20:21Speaker 01

  And so it talks a lot about self-awareness, self-esteem, a lot of themes we talked about. You know, we basically just talked about the book, but there's a lot more detail. It's in Q and A format, so it's quite tangible. The people that have been getting the early copies have been way more, I'm, these are, some of the people actually don't love me that much during the media. Other people are like my homies and kinda know my spiel. And I've been very, I know it's good because of the response from both parties. You know, like, I can feel the lack of pandering from my homies. We're like, crap, this is pretty, like, it's kind of like, crap, this is pretty good.

• 1:20:55Rich Roll?

  Right, right.

• 1:20:55Speaker 01

  I'm like, what do you mean? Like, I'm like, fuck you, aren't you, you know? And then, and then, you know, there's been a couple of real cynical media outlets that have written really good reviews, who like, I know it was painful for the person to say it was good, because they don't like my energy, or they think I'm too egotistical, or duh, duh, duh, duh, duh, duh, duh. I think people really see in me what they wanna see. If you wanna look at me in a microcosm on stage, you can say I'm super egotistical, narcissistic. And then if you're not cynical, you can see how self-deprecating, humble I am. And I know I pull from both ends. And it's fun to watch how, I actually vet people based on how they react to me.

• 1:21:33Rich Roll?

  Yeah, because they're just, they're just projecting their own baggage onto you.

• 1:21:38Speaker 01

  And that's okay.

• 1:21:38Rich Roll?

  And that's going to come out, you know, in all sorts of ways.

• 1:21:41Speaker 01

  And I understand that. It doesn't make me mad. For me, what doesn't make me mad is I'm the ultimate marathon runner. Like, I know what this looks like when I'm 60, 70, and 80. I know where I'm going to be. I know what people are going to think about me. Because it's a level of work. Like, look, we don't get, like, look, I can't hide my actions. You're gonna feel the vibe. You're gonna see. You've met so many people. You see how their assistants, or people around them, or the general vibe, or how they interact. Like, you just can't hide. Eventually, you can't hide.

• 1:22:08Rich Roll?

  And you're not hiding?

• 1:22:09Speaker 01

  Never.

• 1:22:10Rich Roll?

  No. Thanks, Gary.

• 1:22:11Speaker 01

  Thank you, brother.

• 1:22:12Rich Roll?

  I appreciate it, man. So tomorrow is, the book comes out March 8th, yeah?

• 1:22:16Speaker 01

  Yes.

• 1:22:17Rich Roll?

  March 8th. And tomorrow, you got Super 8?

• 1:22:19Speaker 01

  Super 8. I'm gonna sit in this room for eight hours.

• 1:22:22Rich Roll?

  Live streaming for eight hours straight. That's gonna be fascinating to watch, man. So.

• 1:22:26Speaker 01

  Thanks for having me, brother. Congrats on your success.

• 1:22:28Rich Roll?

  Yeah, thank you, man. I appreciate the time. Take care, buddy.

• 1:22:34Speaker 01

  That was a lot of fun.

• 1:22:40Rich Roll?

  All right, what just happened? How'd that go for you? I had fun. I hope you guys did, too. It's really hard to describe the cacophony in Gary's office. There's so much going on. And watching Gary multitask and flow from one thing to the next over the course of a couple hours was really quite something, I have to tell you. I want to give a shout out to Gary's main man, Alex D. Simone, for helping make the whole thing happen. And I even had the opportunity to go back to VaynerMedia the next day, following the podcast, and sit in with Gary on Super 8, which was really, really fun. And you can catch that on his YouTube channel, as well as a brief appearance by me in his daily V, number 17.

• 1:23:22Rich Roll?

  I think I come in about 10 minutes in, or something like that. Links to both of those in the show notes for this episode. And speaking of show notes, please check out the episode page at richroll.com. Tons of links and resources mentioned during the course of this conversation to take your edification beyond the earbuds. For all your plant-powered and RRP schwag and merch needs, visit richroll.com. All kinds of cool stuff there. Nutrition products, plant-powered t-shirts. We've got sticker packs. We even have fine art prints, so you can check that out. Keep sending in your questions for future Q and A podcasts. [email protected]. Shout out to Sean Patterson for all his help on the graphics for this episode, Chris Swan for production assistance, and the interstitial music on this episode was

• 1:24:07Rich Roll?

  done by Tox, T-A-W-X. She's a podcast fan and graciously allowed me to use her music, which is really cool, and you can find her at soundcloud.com/Tox, T-A-W-X. And stick around a few minutes longer because I'm gonna end the show today with my boys' band, Anna Lema's rendition of David Bowie's "Life on Mars." I used this tune interstitially last week. People dug it, I got a bunch of messages about it, so I thought I'd share the entire song at the very end here today. You can find Anna Lema on SoundCloud and Facebook, links on the episode page to those pages. In any event, thanks for all the support, you guys. Remember, small actions taken

• 1:24:49Rich Roll?

  daily move mountains. So if there's something you wish to more fully express, take a step, any step, today, because today is all we have. Love you, guys. See you soon. Peace.

• 1:25:07Rich Roll?

  Plants.

• 1:25:09Speaker 02

  It's a god-awful small affair To the girl with the mousy hair But her mommy is yelling "No"

• 1:25:23Speaker 02

  And her daddy has told her to go But her friend is nowhere to be seen So she walks through a sunken dream To the seat with the clearest view

• 1:25:41Speaker 02

  And she's hooked to the silver screen But the film is a saddling bore

• 1:25:50Speaker 02

  'Cause she's lived it ten times or more She could spit in the eyes of fools As I ask her to focus on sailors Fighting in the dancehall Oh, man, look at those cavemen girls

• 1:26:14Speaker 02

  It's the freakiest show. Take a look at the lawman beating up the wrong guy. Oh man, I wonder if you'll ever know.

• 1:26:31Speaker 02

  It's in the best-selling show.

• 1:26:36Speaker 02

  Is there life on Mars?

• 1:26:52Speaker 02

  It's on America's tortured brow. That Mickey Mouse has grown up a cow.

• 1:27:02Speaker 02

  All the workers have struck for fame. Cause Lennon's on sale again. See the mice in them million hearts. From Ibiza to the North Pole broads. To a ten years out of bounds. To my mother, my dog and clowns. But the film is a saddening bore. Cause I've wrote it ten times or more.

• 1:27:38Speaker 02

  It's about to be writ again. As I ask you to focus on sailors fighting in the dance hall. Oh man, look at those cavemen go.

• 1:27:57Speaker 02

  It's the freakiest show. Take a look at the lawman beating up the wrong guy. Oh man, I wonder if you'll ever know.

• 1:28:14Speaker 02

  Sing the best sound show

• 1:28:19Speaker 02

  It's the life on my

• 1:29:14Speaker 02

  ...