#AskGaryVee: One Entrepreneur’s Take on Leadership, Social Media and Self-Awareness

I think most people know him, but just in case, today’s guest is Gary Vaynerchuk. He is the founder of the digital social agency, VaynerMedia. They work with brands like Spotify, Mountain Dew and Budweiser. They help those brands with creative social media campaigns, ad buying and so much more.

His latest book is called “#AskGaryVee: One Entrepreneur’s Take on Leadership, Social Media and Self-Awareness.”

I discovered in this book what VaynerMedia is worth. I zeroed in–out of all these pages, I zeroed in on one number. Find out that and so much more in this interview.

Gary Vaynerchuk

Gary Vaynerchuk


Gary Vaynerchuk is the founder of VaynerMedia, the digital social agency that works with brands like Spotify, Mountain Dew and Budweiser. They help those brands with creative social media campaigns, ad buying and so much more.


Full Interview Transcript

Andrew: Hey there, freedom fighters. You know me. My name is Andrew Warner. I am the founder of Mixergy.com. It is, of course, home of the ambitious upstart. This is a place where I really dig into entrepreneurs about how they built their businesses so I can understand it because I know I’ve got an audience of real entrepreneurs. Gary, you just moved the camera so that there’s so much space over your head so that you look like you’re small. I want you to own that camera.

Gary: I wanted everybody to see my Mike Tyson stuff and all that stuff.

Andrew: I do like looking over your shoulder to see what’s going on there. I should introduce you. I think most people know who you are, but just in case, the guy you see on your screen now centered is Gary Vaynerchuk. He is the founder of the digital social agency, VaynerMedia. They work with brands like Spotify, Mountain Dew and Budweiser. They help those brands with creative social media campaigns, ad buying and so much more.

His latest book–let me hold it up right here for the camera–it’s called “#AskGaryVee: One Entrepreneur’s Take on Leadership, Social Media and Self-Awareness.” Gary, I’ve read all of your business books. You had one about wine. I’m not that much into wine, but I love business.

Of all your books, this is the one that has your voice in it the most and it’s because you’re answering people’s questions in your own voice. As I read it, the end of each day, I would freaking hear your voice in my head, like, “Should you be sleeping now? Go hustle. Are you thinking about the clouds or the dirt?” like constantly because I’m thinking through your words here in this book.

Before we start with a list of questions that I brought into this interview, I should also say this interview is sponsored by HostGator and Toptal. I’ll tell you more about them later. But first, Gary, welcome.

Gary: Thank you, brother. Thank you for having me on. It’s really good to see you.

Andrew: Good to see you again. Dude, VaynerMedia, I discovered in this book what it was worth. I zeroed in–out of all these pages, I zeroed in on one number. Can you say to people what the company is worth?

Gary: I know what it’s worth now. I don’t know what I said in there. It’s probably worth $325 million.

Andrew: You said you started two $50 million companies. So, does that mean that VaynerMedia, being a $50 million company, was doing $50 million in annual sales in 2015?

Gary: VaynerMedia did $60 million last year and is going to do $100 million this year. Agencies in the digital world are worth two and a half to three and a half times revenue. I’m not selling it, but if I was to sell my agency, I’m such a big deal in this practice that I could probably even push it up to four times revenue. So, it’s worth a lot of money, man.

Andrew: Really? For this thing that you and your brother started–I think before he got out of school you said that you guys were talking about doing it. You also said in your book that you guys had some doubts about whether this was the right idea. Can you talk a little bit about the doubts?

Gary: Yeah. It was 2009, 2010, 2011, the internet was booming. People were building products and services. We’re starting a client service business, right? So AJ’s got all these friends that are worth all this money on paper that are starting to get involved in all these startups. I’m going to meetings and getting talked to about marketing by students. It was painful. It sucked.

So, it’s still tough. Client service is tough. Agencies are tough. We’ve grown from 30 to 625 employees in the last four years. It’s been a massive growth. You’re selling people. There are a lot of dynamics with people. So, it is what it is. But at some level, it’s been really gratifying because we’ve built a real tangible business, you know what I mean?

No cash infusion, no M&A activity, always paying for itself from its own incomes–a real business in a world where everyone listening right now, it was all about startup culture, it was all about raising money, it was all about celebrating when you raised money, it was all about the next round of financing and it was absolutely not real, practical business. I pride myself in building actual businesses. So, I’m very excited about it and we’re just starting.

Andrew: I remember interviewing AJ at the time when you started and I asked him, “Why start services when everybody else is doing software?” Is that the answer, that it would have taken a lot more money to start a software company? You didn’t want to raise money. You wanted to build a real business with real revenues. Is that it? Am I summarizing it right?

Gary: Yes. I knew long-term that if I scaled my one talent, which was really being a great marketer of the moment that at scale, I would be able to deploy that against anything. I now have the income, the leverage, the skill sets and the army to deploy it against any business in the world. That means businesses that we take on as clients but it also means businesses that I buy or own.

We’re just now about to deploy VaynerMedia against Wine Library. It’s going to be a big deal. It’s going to help Wine Library even more. I’m going to buy brands and businesses. We’re going to use the talent and services of Vayner. So, it’s scaling my one truth strength. So, I was willing to eat shit and be practical during a boom time because I knew bad times would be ahead. I knew I want to be a war time general and I want to really be practical.

I’m immigrant through and through and I don’t get caught up in the hoopla and the fake entrepreneurship and the valuations. I’m going to build actual businesses. This machine now is at my disposal to deploy against anything. One day VaynerMedia will do the marketing for the New York Jets when I own it.

Andrew: I want to know about how you do marketing at scale. Can you tell me about one of the ideas that you personally had for a client that you’re especially proud of, just as an example of the kind of work you guys do at VaynerMedia. Then I want to ask you how you can scale that. Let’s start with one idea that you had.

Gary: That’s a great question. So, there’s one that’s under–this is crazy you said this. I think I did my first idea for a client in forever. It started running on Facebook yesterday. It’s a four-minute video. I’m still under an NDA on it. They will let me start talking about it soon, not probably by the time you air this. I’ll re-call and give you a dap.

Andrew: How about one of the earlier ones, maybe when it was just you and AJ trying to work with clients?

Gary: I’ll give you one that AJ thought was a brilliant one. AJ got Brisk Iced Tea to put Instagram photos on its can four months after Instagram came out at South by Southwest, which led to a lot of earned media, which caught the attention of the 7-Eleven buyer which got distribution for Brisk Iced Tea at a higher level.

I laid out a marketing plan early on for Nilla Wafers that resulted in my creative team coming up with creative ideas on Pinterest that grew the business by 12% after it was dormant after 11 years of flat business.

Andrew: You were always really good at this. I always admired you and AJ being able to come up with these ideas. Now, when you have to scale the business beyond you, how do you find people and nurture them so they could come up with ideas like that that make sense for clients and that actually will impact, as you say, earned media?

Gary: By educating them on the context and letting them come up with the content. So, by teaching the rules and the practitionership of the current platforms like Facebook or Tumblr–

Andrew: How do you do that? What’s your process internally on educating them internally on all these platforms so they know what tools they have?

Gary: Having an all hands on meeting where all 600 people sit in front of us giving a presentation on my current/our current thinking on Twitter, like we did a few weeks ago, sending company-wide emails and thoughts. You know what’s crazy, Andrew? You’ll love this. I’m putting out a lot of secrets on the #AskGaryVee Show and in this book. Realize, I’m forcing my employees to do. I realize most people even with the tools and the ideas don’t actually execute. So, actually forcing execution…

Andrew: So, the part where you get your team together and you say, “Here’s my thinking on Twitter,” where you email them on your thinking on where Snapchat is going, that’s what you call the clouds versus the dirt, right? That’s you sending it out to them. You’re also saying that you’re ensuring they use it. That’s a part that I hadn’t heard of. What do you mean by ensuring that they use it?

Gary: Well, I’m reviewing what my employees are doing on social as humans. We’re double checking what’s actually going out the door at scale with people that have been here four or five or six years. When Marcus Krzastek, who’s been with us from the day we started the company, sits on top of four to five projects I most care about and double checks, at this point after six years, he knows exactly what I’m looking for.

So, we’re scaling humans, right? Matt, my assistant sitting right here right now, he just knows how I think now two years later, three years later as my assistant more than he did when he first started. There’s an absolute IP exchange with human beings that happens. Sure, they can go leave and work somewhere else and take that. That’s fine.

Because the market changes so much and I always feel like I’m the best practitioner of this, I always feel like I have the advantage of where the winds blow. But we’ve created a system–managers, double-checkers, processes, project managers, creative directors, vice presidents.

Andrew: And if someone’s not picking up an idea and going in the right direction, you will say, “Here’s my thinking,” not about how you should change this, but overall why this new direction makes sense.

Gary: Yeah. And I don’t get that granular. I don’t need to. I want to make sure that everybody understands the religion. I don’t double-check that they’re practicing it as a human, but I have built 45 humans’ jobs to make sure that’s happening and then still things will fall through the cracks and a client will call me out on a discrepancy between my thesis and what I do for them and I see something when I’m double-checking at 11:30 at night the content that we’re putting out for clients. It’s a human thing.

Andrew, you know what’s interesting to me? People are crippled by the quant nature of our society. There’s no perfect. 17% of the work that VaynerMedia did today is stuff that I would shit on, but 83 isn’t. And more importantly, as long as my 17% that I would shit on is still better than everybody we compete with and better than the alternative of what my clients could pay for, that means I’m winning the game as VaynerMedia, got it? As long as I’m creating systems to try to elevate that 17%, then I’m heading in the right direction.

Andrew: Speaking of, I just screwed up. It looks like I’ve double-booked. There’s someone who’s waiting for a conversation now. We’re going to continue now. I’m just going to say, “Sorry, I’ve screwed up. It’s part of my 17 plus percent. I’ll call back.” I didn’t realize. He’s texting me. For some reason, he’s not on my calendar. If someone’s not on my calendar, I forget. You know what? Let me do a quick sponsorship break.

I should tell everyone that my sponsor is HostGator. Right now, I’m going to ask Joe, my editor, to put in an ad for HostGator which is really a conversation that I had with a HostGator user. Joe, please edit it in now and I’ll continue with the conversation.

So, you do both blogging and podcasting.

F: Yeah.

Andrew: What part of it do you like best so far?

F: I’m a former corporate recruiter. To me, interviewing is the funnest job in the universe.

Andrew: What was it like to get started with HostGator?

F: Oh my gosh. I am in love with HostGator. I really am. I built my own site and went with another company for convenience sake, really. I didn’t know about hosting. How did I know how to pick? I quickly became frustrated with that provider. What got me frustrated, the poor quality of support and supporting documentation and implementation. The final straw was I contacted them for information, it was bad. The site went down.

I found HostGator and they made the process of moving so simple for me. I was then working as the virtual marketing manager for a restaurant, a very popular restaurant back in South Jersey where I’m from. At 4:00 on a Saturday afternoon, the chef owner called me in a panic. I had set him up with a very basic WordPress website so he could only make small changes. Somehow, the site was down.

So, I’ve got to call somebody. So, I got HostGator on the phone. The tech person stayed on the line with me for six straight hours.

Andrew: Whoa, at HostGator?

F: Right.

Andrew: Right, under $10 a month and they’re spending six hours on the phone with you. So, my goal for this call is to record a little mini-interview with you to use inside my interviews.

F: Oh, great.

Andrew: Are you okay with me using this within the interview?

F: Whatever works for you. I’m here to help you.

Andrew: In that case, I’ll tell people that they can check out your website. The URL is TheLetsTalkTechShow.com and it’s hosted on HostGator. Anyone out there who wants the same level of support, the same uptime, the same good people that work at HostGator and the low prices, they can go to HostGator.com/Mixergy. When you throw that /Mixergy at the end, you get an extra 30% off. Go to HostGator.com/Mixergy.

Gary, one of the things that you said that just keeps sticking with me is leave no interaction behind. I’ve noticed this about you for years, before I think I even started Mixergy. I would tweet something and you would respond or send me a personal message. I’m trying to do that. It’s outrageously tough. Who has the time to reach out to everyone who’s reaching you on Facebook, like Facebook Wall or Facebook Messenger or Slack groups that we’re all a part of? How do you do it? Not how do you do it–how do I do it?

Gary: You do the best you can and the effort scales the intent and kind of fixes it. Let me explain. Somewhere around 2012, I lost that game. I would no longer be able to 100%–I was there from ’07 to ’12, respond to every email and every tweet and all this stuff. What start happening in ’12 ad ’13 when I was starting to fall short for people that were used to it or first time trying me out on it and they would call me out in it, my community would jump in before I could jump it. Fifty freaking people would say, “But Gary did this and this and the other thing.”

I actually think you do the best you can. You scale the best you can. If you do it for long enough, then you really did it. The brand of it takes over. Now I try my best, but now it’s like in across all these platforms, if I’m getting to 10%, 15%, 20%, I’m crushing it and hitting thousands of people’s lives. But even the math fundamentally, being up 19 hours a day, I would lose. You have to let that go, but you should never say, “I can’t interact with everybody. I’m not going to interact with anybody.”

So, Andrew, you’ve built this personal brand and these opportunities for yourself. We should never get ahead of ourselves and forget the tried and true. You do the best you can and that’s really what it comes down to. For me, it comes down to just really effort, really all I’ve got is effort. All I’ve got is effort.

Andrew: You’ve got your first customer, you said, in “#AskGaryVee” before you started the agency. You used that money then to hire a staff and you and your brother started the business. How did you get that very first customer before you had a real company. You didn’t even have an office. I think you were using somebody’s coworking space. I remember.

Gary: Don’t forget. I had a personal brand at that point. This was pre-“Crush It!” but I was out there a little bit. I met a guy at a networking event or a speech I gave. His name was Brian Martin. He had an agency. He seemed really smart, “I’m interested in you. Do you do this marketing besides the thing you do for the wine business?” I go, “Weirdly enough, I’m about to start a company around it.” He said, “I’m doing this project for Gillette. I would love for you to help us.”

He goes, “How much would you want for this project to do your Facebook Twitter thing you believe in so much. I don’t know much about that but it sounds cool. I think I could sell it through to Gillette.” I calculated how much my six months’ worth of salary for all these kids that AJ had for our business. I said, “I don’t know, $90,000?” He said, “Done.” I said, “Awesome.” So, that’s what I did.

Andrew: For $90,000 what did they get?

Gary: It was really crappy, actually. I’m not super-proud of it, actually. They didn’t let us do what we wanted to. We wanted to answer people’s comments on Facebook on Twitter. We were very big on community management, back to the last question. We were supposed to do some content, put on Twitter. They told us not to do any of that stuff.

We basically did a live activation in Las Vegas at a part where we took some pictures and put it on social. It was really crappy work, in my opinion. I felt okay because they wouldn’t let us do what we wanted to do. I had to get used to that because I was always in charge before. Now I was doing B2B and they were in charge.

So, it was actually very average, nothing work. Actually, I was like, “Oh, this is going to be a piece of cake. If they think this is worth $90,000, I’m going to make a gazillion.” I quickly realized that was an anomaly. That guy was getting paid a lot of money overall and it wasn’t a big deal to him, that percentage. We would struggle to get $40,000 for things that we were putting $80,000 to $100,000 worth of work for in the beginning days because people didn’t believe in social.

Andrew: Was there a time when you got close to losing the business or losing money?

Gary: No. Maybe one time I put a couple bucks in for payroll and got paid back because the cash flow of getting paid. I really know how to run businesses. It’s funny. When I started becoming Gary Vee instead of Gary Vaynerchuk, everybody kind of forgot that I actually built a big wine business. As I became more of an author and speaker and pundit and all this bull crap, it’s been fun for me to build this very large business because it’s reminded everybody that I’m a true operator.

Andrew: You know, you just said, “I really know how to run businesses.” I notice you sprinkle those kinds of phrases within your speeches and in your conversation. I even noticed that you use it your book. One of the things that I did to prepare for this interview is go back and listen to the audio book of one of your books. If anyone has just read your books, they’ve got to go and get the audio book. It’s a trip.

I’ve never seen an author do this–interrupt his own reading of the book to comment on what he said and to toss phrases in. One thing stuck out to me–I actually wrote it down on Evernote on my phone. You said, “I’m ridiculously good looking.” And then you went on. Going off script, “I’m ridiculously good looking. All right. Let’s get back.” I wonder about how intentional are these phrases? They seem effective.

Gary: That’s interesting. I’ve gotten to this weird place, Andrew, where I’m wondering if I’m doing things subconsciously or actually on purpose. Because I live such an EQ life versus an IQ life where so much of it is predicated on my intuition, my intuitive nature, my people skills, my gratitude, my empathy, my self-confidence, it’s all emotional wiring.

I really do think when I’m all said and done, it has a lot more to do with all those intangibles than how smart I was. I actually think I’m probably average to below average. I do think I see pattern recognition. I see around corners. I’ve got a good history of that. I don’t know. I don’t know how much of it is a shtick. I don’t think I do any of the stuff on purpose.

It’s fun when my high school friends and college friends and pre-school friends and grammar school friends, they’ve helped remind me as I’ve gotten more notoriety that I was a pretty intriguing character all along. I think I’m a weird dude. I really do. I really do think I’m a weird dude.

Andrew: What’s the weirdest thing about you?

Gary: I think that I’m a heavy duty contradiction. I truly think I’m one of the five to ten best businessmen of this generation. I think thirty years, that will be proven out because I’m tortoise, but I’m in a hare’s costume. I’m high-energy. I equally have that ego and I equally think that if I disappear tomorrow because I got hit by a bus, I’d have half a day of the internet mourning and then the internet would forget.

I think I’m special. I know I’m not special. I think I’m the best. I recognize that I’m just like everybody else. I’m pulling in these opposite directions of ego and humility. I think that I’m confusing to a lot of people. Then I wonder if I do it on purpose. One thing I’m proud of is I think the more people really know who I am as a person, I win. I think that somebody catching me on this podcast for the first time may see bravado or competitiveness that may turn them off. I think about that. Does that make sense?

Andrew: It does. I remember Leo Laporte, before he did interview podcasts, someone said, “You should have Gary Vaynerchuk on here. He’s high-energy and he’s really good at drawing a crowd.” Leo said, “I can’t deal with that. He’s too high-energy for me.” I was so let down, but a few months later, he reached out to you and had you on. To me, that is totally you. You could have gone in and been aggressive with him, the way, for example, Jason Calacanis, a mutual friend was or would have been. But you don’t work that way.

Gary: I don’t. I think I’m going to win at the end.

Andrew: Do you feel like repeating it to yourself and repeating it out loud helps ensure it?

Gary: Maybe.

Andrew: How? How does it help?

Gary: I don’t know. You don’t hear a lot from me. So, everybody’s listening is just going to smile, probably, but I’m aware that I do believe that telling the market what to do is real.

Andrew: What does that mean, telling the market what to do is real?

Gary: I believe that telling the market what is going–I don’t think you can manipulate people. I don’t think it’s about a cult of personality. I truly think that me saying that I’m going to buy the New York Jets as much as I do actually leads to me buying the New York Jets and not in like some bullshit secret way. I think it maybe helps me stay grounded in what my focus is and thus kind of like creates behavior in me and others that predicate towards that reality.

Andrew: I see what you mean. I get it.

Gary: It’s interesting, man. It’s just how I see the world working. I don’t think that it’s the secret, but I do believe that people can will themselves to far bigger things than they may realize. I really do believe that.

Andrew: And saying it like that, “I’m going to buy the Jets,” is one way that you’re willing it?

Gary: Another way is when I sell a piece of VaynerMedia to Stephen Ross who owns the Miami Dolphins at a price that doesn’t make me happy because I know I’m about to explode the business, but I realize it gets me in the NFL family and all the other variables and aligns me with a billionaire, that is also a way for me to buy the New York Jets.

Andrew: I didn’t realize you did that.

Gary: I do things that go towards that North Star. I would have never sold Vayner when it was at $14 million revenue when I knew it was going to $100 million and $400 million. I did it because I knew other things would happen because of it that would lead me towards what I care about.

Andrew: Did you take any money off the table when you sold?

Gary: We only took the money off the table.

Andrew: Just for you and AJ to have some–

Gary: AJ needed it for what he wanted in his life. I kind of just took it.

Andrew: What do you mean? What did he want in his life?

Gary: We were paying ourselves no money. He wanted to buy a house.

Andrew: I see. And he was married.

Gary: Exactly. We were putting all the money back in the business. So, AJ wanted a better lifestyle, a different lifestyle than making $58,000 a year or whatever the fuck we were paying ourselves.

Andrew: Let me do a quick sponsorship break and then I’m going to come back. I’ve got some questions including this weird thing that I saw in the book. The sponsor is for a company called Toptal. If you are hiring developers, you know how hard it is to find guys who are really super smart. The guys over at Toptal have found them.

They’ve got a network of people that they’ve vetted, that they’ve tested. They know they’re the best because they reject 97% of the people who apply. When you need a developer, go to Toptal.com/Mixergy. They’ll hook you up with one of their developers. You can start within days. If it’s not a perfect match, no risk. If you do love them, they’ll give you 80 free developer hours. Go to Toptal.com/Mixergy.

Gary, you should write them down. They are really good.

Gary: I thought that was pretty interesting, actually.

Andrew: Andreessen Horowitz invested in them. They just hook you up with great guys. Here’s what I noticed. I’m one of the weirdos who actually reads the acknowledgment pages of books. I see here in the line in the acknowledgement of “#AskGaryVee.” It says, “Finally, thanks again to my writer, Stephanie Land, who besides my brother and my dad,” and I know how close you are with your brother and your dad, “Besides my brother and my dad has been the closest partner in business. I can’t believe this is book number four.”

Who’s Stephanie Land and how does she fit in with this stratosphere with your brother and dad as partners in business?

Gary: I don’t really have that many other partners–I don’t have any partners in business besides them, really, though Matt Hagen, Steve Ross, the guys from that deal that I mentioned. So, that’s probably a little unfair. Stephanie Land has been my ghostwriter for all four of my books. I adore her.

She literally gets out of the way in a way that takes so much humility. I’m petrified for the book not to be me, right? All I want her to do is fix the grammar and get my head around creating structure around it. But no words can be anything but me. So, I just found the perfect partner for me, where a lot of other ghostwriters want to impose their DNA on it, you know me, a lot of you know me. I’m a unique dude. I’m a funny character. It has to be me.

So, I’m just very thankful that I found a book writing partner who doesn’t need a single word. If I say a word that’s not a word like I do sometimes in real life, she’ll say, “Listen, you can’t juxtaposition there. That doesn’t mean anything.” Then I say to her, “Can we say that? That’s what I want to say.” She’s like, “Probably not. The editors will kill it anyway.” She helps me think through the chapters. She helps me structure. But I usually spend three or four days with her and talk to her and I basically talk my books out.

Andrew: I remember actually when you first got a book deal, someone on TechCrunch said, “How is this guy going to write a book? He never read a book and he says that he’s not a good writer.” You actually went–back then there were video comments on TechCrunch and you said, “I’m going to speak it,” and that was it. That’s what you’ve been doing. You’ve been speaking it.

I’ve got a couple of other questions from the book.

Gary: Please.

Andrew: The first is you said your mom brainwashed you in “#AskGaryVee,” that she made you think that the ordinary things you did were extraordinary and I can see how that influenced who you are today. You also said that’s what you do for your employees. Can you give me an example of how you brainwash your employees into thinking that they’re extraordinary and bring out the extraordinary in them?

Gary: I just try to pay attention to what they’re good at. When they execute on that strength, I try to comment them or acknowledge that it’s really strong or I try to make them understand that the things they’re good at are the things they most have to focus on, yet I acknowledge the things they’re poor at. My mom punished me when I got bad grades. So, it wasn’t like eighth place trophies. I’m not saying that was great when it’s not great. But I’ll tell them when I feel happy about something.

Another thing, I always do it in reverse. I also don’t put my headaches or degrade them. It’s almost what I’m not doing a lot of times is also doing that. If they’re hearing from me, it’s a positive. That’s what my mom did.

Andrew: How do you reprimand? I got this interview here with you today because of Alex De Simone who I see in the book and I can how you’re letting the world know that here’s one of the guys on my team and it’s a big compliment. What if Alex screwed up? What if he puts you on Mixergy and you go, “I don’t want to talk to this guy Andrew anymore?” How would you let him know that without being a jerk and ruining the relationship?

Gary: I usually let 5 to 7 to 13 things build up. Alex, I’ll go very real with you. Alex and I had a meeting where he’s like, “I want to grow to this.” I was like, “Not yet and here’s why.”

Andrew: And just be open, “Here’s why it’s not making sense.”

Gary: Listen, I don’t like delivering bad news. So, it’s not so easy for me. But I’ve gotten better. I’ve definitely gotten better and I’m getting better and it’s important because you can’t not give people feedback because then they don’t know–at Wine Library, I would be positive, positive, positive and then I would call you in and say, “You’re fired.” I was absolutely sideswiping people because I didn’t like confrontation. I would build up to one confrontational moment and they’d be out.

Andrew: I see.

Gary: I’ve done a much better job of personally doing it and definitely having VaynerMedia and HR and other aspects be able to give people critical feedback.

Andrew: Okay. I have three more questions. I had this one about AJ that was a follow up to something else and I forgot. AJ–you say everyone needs to be social and be on social media. I don’t see AJ out there. I went to his homepage. He links just to his Twitter account and his Twitter account hasn’t had much activity in the last month.

Gary: I want to clarify. Yes. More importantly, I think that everybody should understand the power of the upside of being on social, but I want to make sure I clean up any things and details. In “Thank You Economy” or “Jab,” I think extensively on like–remember when every CEO should be on Twitter. I was loud about, “No way. What if you’re a jerk? What if you’re an introvert? What if you don’t like people?”

So, I think there’s enormous upside in it, but AJ is dramatically more introverted than I am, though he’s not introverted. I’m just a fucking maniac. I think you should understand the powers of social, but it doesn’t necessarily mean it’s for everybody and you shouldn’t force yourself to do anything that doesn’t come natural or that you’re good at. So, that’s that.

Andrew: That makes sense. I do see AJ–I guess I see him as more social, maybe because I remember walking through Austin at South by Southwest. I was like two blocks away. There’s no reason why should have recognized me. But he recognized me and called me by name. I thought, “This is extraordinary that the guy would be able to do it.”

Gary: He’s the best goddamn dude. He’s actually quite–that’s why I hedged and said, “He’s not actually introverted. He’s just normal.” But by context, when your brother is looking meet every person on earth, it feels different, I guess.

Andrew: All right. Two more–I talked with a friend earlier today about you. He said that you’ve got a deal where he could talk to you for three minutes if he buys a stack of books.

Gary: Yeah.

Andrew: I know from Tim Ferriss that process works. I’m wondering what else works for you for selling books. Here you are now where I’m assuming you’re promoting “#AskGaryVee.” You’ve promoted other books before. What’s worked exceptionally well?

Gary: Selling time, selling what people want.

Andrew: They want your time.

Gary: Yeah. I just heard you say that and I said, “That guy is such a dick.”

Andrew: My friend?

Gary: No, me. This fucking asshole wants to trade a bunch of books for three minutes? What a fuckface. The truth is, I don’t have time. Time is the asset. So, I thought it was more five minutes on the website than three. But the truth is it’s been word. I did it for “Crush It!” Six of like the nine people that took the five minutes of it, I actually gave them something that made them a lot more money, exactly what they wanted. Three didn’t and then I felt bad and so I spent 15 more and so I fucked up my own game.

I think you give people what they want. So, one thing I think really works is access. People want access, man. Access works in a lot of ways. We have a relationship. So, I want to do this podcast. You have a great audience. I did stuff with you before you had this kind of audience. I like you and there’s room for that. I do stuff serendipitously, not quid pro quo. When I’m in the right hook mode, when I’m in sales mode, I don’t feel embarrassed to trade whatever I can trade, I want to sell books. I just want to sell books.

So, what works is what people want. Access is at the top of that. Exclusive content and information work. Experiences work. For me, I get paid a lot of money to publicly speak. So, I can trade lots of books for that. There are a lot of different things that could work.

Andrew: Okay. Finally, you seem to really get in people’s heads, in your customers’ heads. What do you do, besides reading what they write online, what do you do to understand what issues people like me are having so that you’re writing–actually, I can answer my own question. It’s the freaking questions that you get asked by people that lets you know where their problems are, that lets you know where their heads are.

Gary: Got it.

Andrew: Let me reframe the question. How do you come up with answers to every freaking thing? I saw you on stage once. You said, “I’m not going to do a talk. I’m just going to take questions.” You had a Wall Street Journal reporter sitting next to you moderating the questions from the audience. How do have the answers to whatever they come up with? Do you have a process that if you don’t know the answer, you can twist it into something do? What do you do?

Gary: Yes. The answer is, “I don’t know.” It blows people away. The other day, I was rolling on stage, rolling. I was sharp. The questions were coming in good. I’m a practitioner. I was at the top of my game. Then a question came and I said, “I don’t know.” It was a question about Stephen Hawkins and I just didn’t know. The crowd’s reaction was so goddamn interesting to me. It made all the other nine answers that I just gave so much more valuable.

You know, Andrew, people ask me questions around my genre. I’m out there. If you’re going to ask me about marketing or business, I’m going to have a good answer. Listen, the #AskGaryVee Show, DailyVee, the blog–have you seen any of the DailyVees yet?

Andrew: Yes, I did. That’s where you’re being followed around?

Gary: Yes. That’s been big for me because now people realize how hard I actually work. The 16 other hours that you’re not seeing me every day for the 42 minutes you are seeing me, I’m a practitioner. That’s it, man. Do you understand?

Andrew: I get what you’re saying. You’re saying you know the answers because you’ve been doing it.

Gary: Correct. I’m not reading shit. I don’t listen to anybody’s podcast. I don’t do anything. I just work. I watch consumer behavior. I do work. I do work on my brand. I do work for Vayner clients. I’m building an actual business as CEO of this company. I’m having conversations with the biggest and most important CEOs across Fortune 500 and startup land. I do work.

Andrew: Yeah. And you talk about that in the book in “#AskGaryVee.” You asked me before we started. You said you were curious what I thought about it. I was curious too. I thought, “I heard so much of this before. Why would I want to reread it?” I usually don’t like question/answer books because it doesn’t allow me to just flow through the book. I really enjoyed it. I loved it.

What I loved about it was your voices, as people are hearing it now and on the show, on paper. Yes, I heard some of these answers before. I think for me, I absorb information better when it’s written. I know that you absorb it better differently. I know other people are just going to flip through it looking for answers to the sections that they’re working on like how to hustle or about family. You’ve got a whole bunch. Everything is organized really well. I can see people saying, “This is like my encyclopedia. I’m going to go see the answer to my question.” For me, it was read it straight through question after question and just get absorbed in Gary’s mind in your thinking. I really liked it. I think it was actually my favorite of all your books. Go figure. I didn’t expect that.

Gary: Dude, I fucking have chills right now. My brand is no question at its strongest place because I’ve been very active for the last 18 months. I’m freaking out man because people like you, book four, after being around my ecosystem for a long time, you’re busy now, you’re like at a different place in your career. There’s no good reason on paper this should be your favorite.

People that don’t even like me that much in media that got it from the publisher, I’ve gotten three emails from people that literally it said literally in the headline the first one was, “I thought you were an asshole.” I open it. They’re like, “I thought you were an asshole. I think you think you’re cocky as shit. I’ve got to tell you. They send me the fucking galley. I was like fuck this guy. I’ve got to fucking cover it for my newspaper, for my website. Let me read two or three things so I can bash him.” This is literally what the person wrote me.

Andrew: I can imagine.

Gary: They’re like, “Son of a bitch, four hours later, now I love you. I’ve watched four of your keynotes. I didn’t get it.” That, to me, sometimes I wonder if I’m this personality because I’m the, “Aha, I told you so,” so much. I’ve got a shot with this one, bro. I’ve got a shot.

Andrew: I think so too. I wouldn’t have expected question and answers and so on. People have to know who Gary Vee is to some degree. It’s not offering me anything beyond Gary Vee’s opinions.

Gary: You know what’s funny? My publisher said I sabotaged this book by doing that. My publisher said if you call this what it is, which is the modern entrepreneurial blueprint or the 360 view from an operator–

Andrew: Yes.

Gary: If I called it back, it would be ten times bigger. She said, “You’re such a fucking son of a bitch.” She said, “You’re always aha’ing everybody.” She said, “You could have gotten your just due with this one and yet, after saying to me that you would never write a book with your picture on it or about you, that they’ve got to be called Crush It and this and that, you did that with this.” I said, “God dammit.”

Andrew, I think that I want to hold on to this thing because I love the title that says, “I thought you were an asshole and then…” There’s some shtick that I’m not letting go of yet. I need to be careful because maybe I could fuck that up and become angry about that.

Andrew: Like the proving the world wrong thing is what you’re talking about.

Gary: I’ve got to let go of this chip a little but because I think it’s holding me back. But I kind of like it because I like the struggle. It’s a whole thing. All that is okay. I don’t care about that one way or the other if the book is really good.

Andrew: That’s right. Frankly, I’ll tell you now. My goal for this interview was just use the book as an excuse, like, “Gary, I’m going to give you an intro with the book and talk about it at the end and screw the rest of it.” I ended up just highlighting stuff and bringing it up in conversation. It’s really good.

Anyone who’s listening to me knows I don’t have to compliment the book. I don’t get any sales from it. You’re not going to not show up next time because I didn’t give you ten minutes on the book. But I like it. I think you guys will enjoy it too. If you do, please let me know. If you don’t, let me know that too. I also want to hear that from you guys.

All right. “#AskGaryVee” is the name of the book. Gary, thank you so much for doing the interview. Thank you all for being a part of it. Thank you Toptal and HostGator for sponsoring. Bye, everyone.

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