#AskGaryVee on Entrepreneurship

Today we are pleased to bring you more on #AskGaryVee.  Gary Vaynerchuk is a successful entrepreneur who builds businesses. He helped grow his family business from $3 million to $45 million in just five years. He is the voice behind The #AskGaryVee show and we want to share a part of his Entrepreneurship transcription.  Take a look:

Ask Gary Vee Version 1.41 Entrepreneur’s Journey

Both here and on your Facebook posts, you have no links, no email signup. Do you just trust that with enough goodwill and trust, people will find your website/email when it's time to buy? If I need my content to drive bookings, should I not at least have a link for more info when people are ready for it?

Gary: Listen, spoken like a real salesman, and I'm a real salesman. I'm a real salesman, but you're not wrong. I'm all about the CTA, Right? The call to action. I'm into that. Right? But at the end of the day, you're talking about the difference between salesmanship and branding.

Anybody could be a good salesman, but being a great brander, that's where it gets going. The lift of being a brand, being a Nike, being a Puma, versus just selling a new sneaker, that's a big difference. So tactically you're correct, that I'm sure a lot of people who watch this think about those things, where, "Why didn't Gary create a call to action? Why does he have a popup when I land on his website to collect my email?" All these growth-hacking things many other people do.

The reason, at times, I don't do it, because at times I do, at times, I'm very comfortable throwing the right hook is because I do believe in the jab. I believe that branding matters. I believe that there's a time and a place. I believe there's context.

In this setting, yes, I do think that in a 2015 world, people watch this show. They see that I'm not trying to sell them anything. I'm bringing value. I'm sitting here during my favorite time in the world, which is Jets parking lot time, because I want to put out content, and I'm just trying to give the best business advice that I can.

I do believe that when somebody stumbles across this, yes, there'll be a call to action. They can click, and they could buy. But by me asking for something like, "Sign up for this and buy that," in this video or in this world of YouTube, I'm also leaving away the situation where that person can then look at my name, find this interesting, control-copy it, go to Google, search my name, go down a rabbit hole, and let me build brand because I asked, like everybody else out there, for the quick sale in this context.

It's kind of like relationships. Because I went to sleep with that person on the first night, maybe I took away the chance for us to get married. I, my friend, am playing the long game, the depth game, not the width game. So there's a time and a place for a call to action, a CTA, but that isn't every single at-bat, every single time, every single channel, because then you just become a sleazy salesman.


Question: So you've been in the influencer space for just over a year, specifically with Grape Story. With that business model, what are the biggest challenges you're facing in scaling that business model? And what is the brand that you would say is embracing that model for marketing with mobile in those channels, Twitter, Snapchat, and Instagram specifically?

Gary: Which brands are doing a good job in those channels, using influencers? I think a lot of brands are starting to do it well, right? Any brand that's not doing it well is losing, but I think our GE client was first to jump, did a really good job. Virgin Mobile has done a really good job. I think Hewlett-Packard right now, Samsung. There's a lot of brands, I think, that are getting the value of influencer.

The problem with scaling my businesses… We're a talent agency. Right? So these guys and gals get built up. We build up with them. Then they get too big, and they want to go to CAA or things of that nature. So unlike Niche, which is an investment one that's building technology and a platform, you guys… There are people that are doing it smarter than me.

The model issue, for me, is it's just client service. It's just people. You only have the leverage for so long, but it's no different than CAA or William Morris. If you're the best, and you're good at it, there's a real business there, but that is clearly the challenge.

To make this an overarching question for everybody, when you decide to build a model where you're not building an asset, which is technology or something of that nature, you're only vulnerable to your sources. It's like being an accountant or a lawyer or an agency. You're only as good as your last billing cycle. That's why those businesses don't look at the higher multiple. That's why people want to build technology companies.

For me, I love people. So I'm always going to have a competitive advantage, betting on my strength, which is people interaction. So I like building those businesses, but I’ve got to tell you something. It's really not for everybody, and there's definitely a huge vulnerability in it.


Question: How do you maintain having high standards with your team, making sure things get done, but still keeping the project on time and on budget?

Gary: I wish Aaron Behr was here from Vayner Media, because he's the head of all that at Vayner Media, and he's killing it. I think it takes humanity. I think the answer is humanity. I actually think the best way to be a great project manager or get things done is to be a great listener instead of talker, right? You go into this new role. I see it with a lot of my project management people. They're organized. They're good, but they want to talk it to success.

I actually think it's the drop-down, flip it, and reverse it. I think it's a Missy Elliot structure. I think the way you win is by listening to the people about why they're not doing well. Why are they two weeks behind? If you actually apply empathy and understand what's going on there, you become known to everybody as the project manager that gets it.

So I say you walk in with not your architecture and organization and, "I'm gonna guide this." You're gonna guide it with your ears more than your mouth, and that is something most project management-oriented people only learn later in life and realize is the key factor.


Question: So what do you think the biggest opportunities are there currently untapped?

Gary: In social media influencers?

Question: All that stuff. But where do you think the next big thing can be in the space?

Gary: To me, this is the biggest thing that people don't understand about the influencer space. Not only do influencers create content. They create distribution. So for the first time ever, in one entity, you get both things that people want. If you think about television, production companies, or movies, Steven Spielberg, but then you need distribution. Right?

So what I would say is the biggest opportunities for these guys, for you, for me, for everybody who's playing in this space, is to recognize that unique principle in today's Internet world, where they actually can drive two things, and then apply them.

The other place that I think there's a huge opportunity, to answer your question and to give everybody more information, go a little deeper as some have been trying to go, is product. I think that the infomercial space, the leveraging of celebrity into product… I, at one point, could have easily sold tens of thousands of glassware sets because of my wine influence. I think retail and product, call it QVC 3.0, is another place that people need to think about.


Question: You advise startups. You invest in startups. But when startups become inherently competitive with other companies, what's your biggest advice to stay ahead of the game? Is it just to give more value than the person behind you? I'm just interested on your thoughts on that.

Gary: I default, as an entrepreneur, thinking it's always going to be competitive. You know? I love when people are like, "Nobody is in our space." I'm like, "Great. Because if you're good, everybody is gonna be in your space." Right? If you figured something out, you're going to have plenty of competitors.

To me, it's the same old game. It's better execution. It's better product. It's better service. It's better everything that's going to actually drive your business. So I can't give a blanket answer here. This is why Vayner Media works in a world of Ask Gary V and me putting out content.

I can give you general stuff. I'm trying to go deeper and give you more stuff with this format, but I need to know who your competitors are. So for you, your business, are they bigger entities with more money? When you're David, you don't play Goliath's game.

When you're Goliath, destroy David. That matchup should have never gotten to the slingshot. Just squish that guy. Right? Here's an example, back to depth, something I'm trying to challenge myself on this show. Was anybody else surprised as hell that I barely talked about Vayner Media for three years? For somebody that's always out there promoting, you notice if you went to Vayner Media's website for the last two, three years, that it was like nothing there, because I was David. I needed to make sure that the bigger agencies didn't realize how big I was actually getting. That was my competitive play in a competitive landscape.

Now that I'm getting a little bit bigger, I'm getting a little bit more out there. I'm putting myself more out there because I have the leverage of having more money to hire the best talent or acquire the biggest clients. So the answer to your question is completely predicated on where you are in your life cycle versus your competitors' life cycle.

What I would tell you is, and here's where I can give the most tangible answer, though still theoretical, never play the other person's game.

That's where everybody gets, “Oh, that big guy or gal is now running ads. We're going to, too.” Problem. They have $10 million, you have $80,000, you lost.  So it's never play the other person's game.

Question: What's up, guys? Pretty quick question. What's your stance on investing in competitive companies?

Gary: For me as a fund?

Question: You as a fund, you individually.

Gary: So if I'm a fund and I, for example, when I was an investor in Gowalla, and there's a chance to invest in Four Square, I didn't, but I know people that have invested in similar companies. Are you asking me to put my VC hat on? An angel hat?

Question: Yeah.
Gary: Look. I think there are two answers. One, I think if you're investing in a company, and there's a chance to invest in somebody who's a direct competitor, and that company wants you to do that, that seems like, to me, like a little bit of a dick move. What I'm more worried about is the problem I'm facing now. To me, the bigger problem is the pivot. Right now, my biggest problem is I'm investing in companies that are a little bit different, but I can see, as an entrepreneur, how one move by each product gets them into a competitive space. My answer is you go in with the open eyes and honesty that you can, but you can't fight against the fact that people are competing with each other, as we now live in a world where the cost of entry to compete with each other is so much lower.

I think you should go in with the right intentions. By the way, the only reason I think you should be a good guy or gal and not invest in a competitor is because your reputation is your equity. It's selfish. It's because I want to be able to invest in things in the future. If I have a reputation for constantly investing in my competitive stuff just to win on short-term money, I'm not going be able to get into deals. So I think reputation management in a transparent world matters. I think that is a dick move if you're doing that.


Question: Andy asks, "Playing Monday morning quarterback, what is something you would do over? And why?"

Gary: I'm going to share something with you guys that I've never shared before. As you guys know, I don't talk a whole lot about losing or making mistakes, outside of passing on Uber in the first round. I don't like to talk about that that much, but I've made my share. By the way, not because I don't want you to think that I don't lose or that I'm so great, because honestly I prefer it to be the other way. I'd actually like you to continue to underestimate me. As a matter of fact, Vayner Nation, I think most of you are valuing me too high. I appreciate it, but I prefer being the underdog, hence my Jets fandom. Notice we're not even talking about that today.
The biggest mistake that I made or one of the biggest ones or one that I've never shared before, hence I want to share it here on the show today, is my key decision in 2009 to start Vayner Media because I believe that we were sitting in a bubble and that it was about to burst in 2010 or '11, that valuations were getting too high in Internet companies, that money was being thrown around too easy.

I've been proven now, over the last five years, to be remarkably incorrect. The market has exponentially grown. Money is being thrown around like candy now. We're very much more in a bubble today than we were in 2009. Because I had a lot of heart in teaching AJ, my brother who was coming out of school, to build a practical business, I didn't want to raise $10 million to do some sort of thing.

I probably left an enormous amount of money on the table. For example, if I went and built a fund in 2009 and '10, I'd probably have early money in Snapchat and Uber and Airbnb and might be very much on my way to buying the New York Jets. So that is my Monday morning quarterback on a Monday morning, after my team got quarterback.

Question: Nassir asks, "Sometimes my passion is seen as aggression. How do I walk the line? Do I change to someone more passive?"

Gary: Nassir, first of all, don't change for anybody now. Finding that balance of grace and having that tack to be consumable is a process. I, somewhere around eighth grade into sophomore year, didn't hit the right tone anymore. I was too intense for my classmates, and I could taste it because I have empathy and self-awareness. It's an ongoing process.
For example, my keynotes are interesting. I'm actually evolving that cadence throughout the conversation of the tone because I'm reacting to the body language of everybody else. It's not about how do you become more passive, because I'd hate to suck the passion out of you, which is a huge variable to success. Controlling it and people saying, "You're just a little too much," I have a feeling that that's predicated on you caring too much for it to be valuable for you.

I'm going to say that again for everybody. The only reason I think that I'm able to pull off this is because there's a healthy balance of caring about you. When you care more about your audience than what you have to say, you start winning. Right? When you care more about your global audience listening or watching, and it's not about the 15 minutes of what am I going to get out of it. Sure, in a right-hook world, it's always there.

Let me actually use this question to find something that I don't think I talked about in the book. I live in a world of jab, jab, jab, right hook. Let me tell you two interesting things with that. I don't necessarily feel that I ever have to throw a right hook, and I don't expect to need to throw a right hook based on my jabs in micro levels. At the holistic level, I do.

Also, there's another part that we never talk about. Is there? Which is what happens when the right hook doesn't land. I'm actually not disappointed. What happens when I do all awesome stuff for these guys or anybody else? I don't have any expectation that they're going to do something awesome for me in return.

Eliminating that lack of expectation opens up a world where you can provide. So based on your question, based on my intuition, my vibe on this question, it has a whole lot to do with you caring more about them, the people that are judging you, that are telling you to chill out. They're telling you that because not about your passion. Take it from me and many other people. People love passion. They don't like selfish passion.


Question: Veronique asks, "You say to put out quality content daily. Can I add curated content to my own content? If yes, what's the right mix?"

Gary:  The answer to your question is absolutely. As a matter of fact, I think what I call DJ-ing, the ability to take content that's going on all around the world right now and bringing it into your voice and putting it out there, is an enormous skill set. I think it's mapping what's happening in the actual music world. Right? You look at what's happening in EDM and other places of that nature. DJs are people that are able to take a lot of different things and put them together. It's really like being a great chef. Isn't it?

So actually I think one of my biggest weaknesses is my lack of curation. Right? Because I take so much pride that the content is mine, I haven't gone out and taken articles from other people and then kind of jumped on top of that. I remember loving Tumblr. One of the reasons I invested in Tumblr way back when was the notion of re-blogging, tumbling something. You hit somebody else's blog post, and then you wrote your two cents on top of it.

The re-tweet functionality with a quote, and then you'd put your own two cents on Twitter, I think, still has a lot more potential. They limit you to room. I love the ability to re-tweet and then have 140 characters and let the whole thing be 250 characters. Twitter, you should steal that because I think that would make Twitter much better.

I think the adding of two cents has always been something that I think has been valuable. You look at somebody like Guy Kawasaki. If you go look at his Twitter feed, it's all curation. Right? He treats himself like a media company. It's almost not him. It's like the Guy Kawasaki network, and he's just putting out hundreds of tweets a day, it feels like, of just different articles, things of that nature, kind of like a human nuzzle or a human RSS feed.

So I think curation of other people's stuff or passing on other headlines is the biggest weakness in my social media content game, and I highly recommend all of you working on it and if it feels comfortable. For a lot of people, I would say here comes a humble brag, but I've been doing a lot of that lately.

So for me, I think the reason I don't do as much curation is I have the ability to do original content at scale. That's a struggle for a lot of people. So for a lot of people that don't know what to say, the curation of other content and being the news source for somebody and the rest of the world, under their context, within their genre, is if you're a yoga person or a health person or a pumpkin picker, your two cents on Apple Pay or George Clooney's wedding or things of that nature, under the context of being a pumpkin picker, matters.


Question: Cory asks, "What have you found is the best way to introduce non-wine drinkers to wine without it seeming overwhelming?"

Gary: Cory, I took this question because not only for the wine people listening, but for the business people that are trying to educate about social media or apps or tech culture. It's the same game. Why did I over-index in the wine world? Why do I think I over-index in the business, marketing, operation, social media, marketing world? I said marketing twice because it's so nice. It's because I talk to people, not down to them.

How do you get people into your thing? How do you do that? You talk to them, to them, not down to them. That's really the struggle for everybody who gets any level of expertise. They get this expertise, and they want to leverage it against their audience to establish, "I'm here. You're here."

I can guarantee the comments coming right now, that one of the reasons people watch and listen to this show and have followed me for the last seven years when I was educating about wine, intimidating subject, or social media, new intimidating subject to a lot of people, is I'm talking level-set. Right? I'm not imposing my expertise. I'm not making anybody feel bad that they don't know as much as me, snickering like, "How could you ask me this question, rookie?" I don't do that. Right?

I understand that there's 99% of the world that I know jack crap about. I know my couple of little things. When I'm trying to learn about other things from other people that know, it's nice to be talked to at that level, which is respect as a human being, not being imposed on something you learned a little bit more about.

So you want to get people into wine or anything else, for all of you that are watching. I say a lot of you who are watching, trying to impose your expertise on food or pets or anything of that nature. I highly recommend you start realizing you're talking to somebody, not down to them.


Question: I run the Personal Development YouTube channel. My question to you is: what would you do if you were starting over and building your personal brand all over again, basically getting the name Gary V out there all over again, in this day and age? What would you do to go out there and really spread the word and to get yourself known?

Gary: I love this question. Boy, I'm going set it up. Do I have a really good answer for this, because you and every other youngster needs to hear this really, really loud and clear. This is not being disrespectful, because I was a 22-year-old genius businessperson in my mind because of what I did, but I would do exactly what I did, which is for the first 10 years of my professional career, I didn't say a damn thing.

At 30, I started Wine Library TV. One would argue that I was really doing business since 14, but I'll just say 22 because it was all in, no school, fine. From 22 to 32, my friend, I did nothing in building the Gary Vaynerchuck brand. You know what I did? I did the work that allowed me to have the audacity to build the Gary Vaynerchuck brand.

This notion that you can just come out great and build your brand by growth hacking and putting yourself out there and getting on some podcasts and leveraging other people's brands to get on and build yourself as an expert in what? When are we going to start asking all these people that are experts what did they do? Here's what I did and why I think you should listen to me in business.

I am now in the midst of building my second $50 million-plus business within a five-year window. That's good execution at a speed that most people can't calibrate, at a high volume. Is it $50 billion? No, but it's a life for a lot of people. It's business. I invested in companies early on and made a lot of money because I saw where the market was going, hence the video I popped up earlier before that's linked below, of what I saw with Apple Pay.

I did things that allowed me to start having a shot to be worthy of people buying a $15 book or spending 15 minutes and watching his or her show. So I did things. So my friend, to you and everybody else, I promise you. Before you get your name out there, it'd be really nice that you can go do the accomplishments.

Because when I ask you, "Hey, bro. Awesome that you're a branding or health or personal coach or whatever the hell you are. But what did you do to become good enough to do this?" I'd like to know. I love when people argue with me on this issue. They're like, "Well, look at all the football coaches." These coaches, a lot of times, are not real players. You don't have to be a great football player to be a great football coach.

Guys, have you looked at every football coach? There is no football coach that comes out of nowhere at 23 years old and is then an NFL coach and wins Super Bowls. They've been a bowl boy since they were seven and worked within the organization for 20 years, 15 years. Eric Mangini, when he was a Jets coach at 36, had been a ball boy since he was 18. They're in it forever. They're kids. They're sons and daughters of coaches. They've been in it their whole lives. That's how you get there.

So this quick move of using good modern technology to build up your brand, siphoning and doing JVs with other people to siphon their brand equity that you're passing on that, "I'm an expert," and then coming out the gate and saying, "I'm an expert, building a brand." It's ludicrous. I laugh at it in my soul, in my stomach, and so does everybody who's got chops.

I'll say it one more time. I laugh at it, and so does everybody that's got chops. I need you to pay attention to that. You have to earn your opportunity to be a personal brand, and the only way to do that is to actually execute. So when somebody asks me, "Well, what makes you a social media expert," I show them things I've sold in sales, business, put money in the pocket, predicated on marketing within that channel. That's a way to do it. That, I believe in.


Question: East County Today says, "Gary, love the iTunes Touch. What was the moment you knew you'd be okay when starting your company?"

Gary: East County, the moment that I knew that I was going to make it was the first day I walked into my dad's liquor store. The reason I decided to answer this question and trying to find value for everybody watching, other than me bragging about that I had the bravado from day one, was the notion of not even worrying about that moment.

One of the things I'm trying to teach all my management here at Vayner Media and all my founders in my startup investments and my co-founders in companies is to not worry about the things that don't matter. Worrying about or trying to figure out this is the moment when I made it is something that I think cripples people. I just don't even think about those things.

I could answer this question two ways. One, the moment I walked into my dad's store because I had that confidence, or I could answer the other way that's equally as true, pulling on both sides like a bridge, which is I haven't made it yet. They both are right.

The truth is, outside of this question, I don't think about it at all, ever, period. The reason I'm answering the question is because I'm trying to get as many of you who are watching this show right now to not worry about those things. Worry about executing. Worry about feeling good about your life. Don't worry about making it, because making it is an outside force. The inside force of you just doing it is what you should be focused on.


Question: Hey, Gary. I'm a realtor, and our team puts out a lot of video. In episode eight, you said it was important to put out daily content. So my question to you is: if you are a realtor, what kind of daily video content would you produce?

Gary: My answer is very simple. If I was a realtor, the thing that I would do more than anything is actually review the area around the places where I sell homes. Let me explain. If I'm selling homes in Millburn, New Jersey, I'm putting out a daily piece of content reviewing the school. Then I'm interviewing the individual teachers if I can get access to them. Then I'm reviewing every local business, the Subway shop, the wine shop.

Then I'm interviewing, literally, people that have lived in the neighborhood for 50 years. I'm putting out content to make you romantic around the stories in the area, because people pick them for utility. What I mean by that is convenience of transportation, how quickly from the office, but they also pick because of the school systems. There's a lot of data out there on that. But how about making it a little warmer and interviewing Miss Robinson, the third-grade teacher?

Then obviously kind of the amenities around it, right? The playground, the best stores. I remember a realtor telling me that people moved to Short Hills because of Wine Library. I thought that was cool. It felt like such an anchor to that area.

So what I would do is daily content on the 20-mile radius or the 10-mile radius around the area where you sell the homes, the stories that are tucked away in the businesses and the school system, and the iconic neighbors that have been around forever. Those stories are the narrative that will create emotion, which will be on a tipping point scale, on a 50/50, maybe the thing that tips someone to buying your home.


Question: Shawn asks, "Gary, most big successes have a huge turning point where things really take off. What was that turning point for Wine Library?"

Gary: Shawn, great question. I guess there were some turning points when the Wine Spectator ad that we ran, the first New York Times full-page ad, the time I reset the store and took 50% of the beer off the floor and added more wine, when I started Winelibrary.com, the day I started the email service, the day I jumped into Robert Parker's forums in '97 and became part of the Internet community around wine, the 2000 bordeaux vintage, when we bought heavy, when I first started promoting wines nobody ever heard of on email, Richard Partridge Cabernet comes to mind, when I hired Brandon.

As you can tell, there are many moments that we made it, but it was just trucking along, building on top of each other, step-by-step. My friends, if you listen to two of my answers on this show, you understand one very interesting thing about me, which is I may have the energy of the hare, but I am the tortoise. You know what I'm putting up there. For everybody listening, I'm pointing to the tortoise and hare image I put out on Instagram. Go check me out on Instagram/garyv-e-e.

Anyway, when I made it, the turning point moment, everybody who's watching and asking these questions are looking for this sign, like I saw the sign, like this sign. It's not that. It's head-down. You love and believe in what you do, and you just never think about those moments. You just keep trucking along. It's lunchpail mentality. It's old-school, eastern European, put in the work mentality.

I don't think about these things, guys. The Fortune 40 under 40 that just happened. Is that a turning point in my career? Sure. Some people now think of me differently because I'm in the context of those people, but it's not. It's just chug and chug and chug and chug and chug and chug and chug and chug. So chug.


Question: Joe asks, "Can anyone create good micro content? How can you make sure your team consistently creates good content?"

Gary: Joe, great question. First, for everybody who's watching and/or listening, I want to talk about the term micro content. It's something I started using three, four years ago. It hasn't really caught on. I, myself, don't know how often I'm going to use it going forward, but the notion was content made specifically for the platform, the videos and the pictures, the quotes, the written words that worked on Facebook, Twitter, Tumblr, Pinterest, Instagram, Snapchat, Vine. It was the context of the book "Jab, Jab, Jab, Right Hook."

So how do you make good micro content? How do you consistently get your team to do it? First of all, content is subjective. Right? Steve likes "Game of Thrones" shows. I don't. Not that I don't like it. I just haven't even seen it yet. Some people watch "Game of Thrones" and don't like it, very few, I think, because it's very popular, but it is still clearly subjective. That's number one.

Number two, how do you get a team to be good at anything when you're scaling your kind of POV on the world and marketing to a 400-person organization? It's about education, but I would actually say that, for me, scaling and getting my team to get there has a lot to do more with osmosis. Right? Putting it into the water stream versus having a class that teaches it. Sure. You can write a book. Sure. We have lunch-and-learns and learn-ups within the organization, but they're not attended that well. We need to talk about that, by the way.

What's happening more here is people are doing, and people are smart. It starts with hiring good people, smart people. Then when you realize you've hired somebody who's not capable of learning through that process, then you've got to make some decisions. But to me, making good content takes a couple of core pillars.

Number one, you've got to respect your audience. Meaning, you've got to respect the psychology of what they're doing when they're on the platform. I know a 40-year-old woman is in a different mindset when she's on Facebook versus when she's on Pinterest. That is how I try to story-tell to her, because I know on Pinterest, she has intent to shop, aspiration to shop. On Facebook, she's keeping up with her world or consuming information. So I strategize around that, the psychology and the platform itself.

Number two, when I say respect, I put out content that I think she will like versus what I'd like to accomplish. Yes, I'd like to, give me a bottle of wine, yes, I'd like to sell this. But if I put it in a way that is more interesting to her, five under-$10 bottles of wine that help you get through the day when you have eight-year-old kids, and then you target eight-year-old kid moms, you're gonna start getting into a game that gives you a better chance.

Twelve wines somebody who's 38 will like, and then you target people that were born in 1975. These are all strategies that will work. Again, very heavy Facebook or Instagram, taking a glamour shot of it in an angle, and it's just cool and nice. It's all that kind of stuff, respecting the audience, respecting the platform, taking your agenda, and making it third.


Question: James asks, "What are your thoughts on podcasters and YouTubers building a business model around donations?"

Gary: James, great question. It's a trend we've seen for a long time. I saw bloggers do this back in 2003, using PayPal as a tip jar. Right? This has been a thing that's been around for a while. I think, though, as the evolution of the Internet is happening, much like the resurgence of podcasts, I see this model in a world of post-Kickstarter becoming more of a trend.

I definitely see it as something that I won't do for myself because I'm just using my content as a global jab, but I could see myself then if it was the only thing I did. If I was only this, if I was only the character that I am when I put on the podcast and the show, meaning, when I say character, I want to define that for you, meaning this is what I do for a living. Right?

I put out my marketing thoughts. I've had my career. I don't want to be a practitioner anymore. I don't want to run this company, and I just want to write books, speak, and put out the show.

More importantly, you start realizing, this is a great piece of advice for all of you, no matter what you do, sell cheese, put out shows, whatever you do. A lot of you do a lot of different things, real estate. You know? That 5% to 10% that most give a crap about you, boy, the Vayner Nation, boy, that stuff really matters. A lot of times, you can rely on them because they're getting value.

I have been blown away, humbled even, by the amount of people who've commented over the last seven to 10 episodes, saying things like, "Man, come to realize I'm really into this show," or, "This is my best part of my day," or, "This is when I get motivated." It starts becoming valuable.

Then I can see the kind of, it's a hedge against, I'm charging for this. It's kind of like a guilt move, but it's also a support-me move. I think it's a very viable kind of attack. If you're considering it or anybody here is considering it, if you have enough mass of loyaltists, you can actually make it valuable. If you only have seven people that give a crap about you, and they give you $10 a month, you got $70 a month. Not going to necessarily crush it that way. But if you've got a real big audience, and you can get that 5% to 10% to really support, there's some dollars behind it.


Question: Roberto asks, "What do you feel is a bigger obstacle to success? A lack of time or a lack of capital?"

Gary: Roberto, this is a tremendous question. I think the biggest obstacle to success is a lack of optimism. That question in itself is the problem, my friend. Right? You're looking at two things that are both negatives. Guess what? Both of them are obstacles. When I started Winelibrary.com, transformation from my business, I had time. I worked my face off every minute, but we didn't have a whole lot of money in our profit center. So it took more time. Right? It's just the way it is.

Today, I have more money. Boy, don't I have time. But neither ever, ever will be an excuse for me. So just to drill this through the throat of the Vayner Nation. That's right. I went that graphic. Don't smile, D-Rock. Here's the bottom line. I refuse to allow you to get an answer to that question, because both of them are firmly square in the excuse column, and I have no patience for that.

There will always be problems. Let's talk about a million other things that are a way to stop success, the health and well-being of your family members. So it takes your mind away from execution. The country you live ins government and political concepts at these moments, a la startups in China that I've invested in that got traction, but then people that were wired into the government decided to not allow it to happen. Then the startup disappeared. Not as easy to be an entrepreneur there. It's still a communist country. Sorry. It just is.

So all these things can be problems. Right? There's a competitor with $1 billion, who's also skilled and punches you in the mouth and knocks you out in the first round. Right? The world is changing. There's just a million obstacles. Right? The media, one bad coverage of you, a moment in time. You know what I think about a lot? Let's get really real. This is why we did this show.

I'm a human being, and I always think about a moment in time. What if I just say the wrong thing at the wrong time? Right? What if I call out China for being a communist country in an episode, while I'm on a rant, and somebody who's watching doesn't like the way that tastes, and it takes away a business opportunity for me in China in seven years? Even though I'm not trying to zing, it's just things that I saw.

What if? What if I look down on my phone while I'm driving, even though I've really not done that, and I hit somebody, and I kill them? That becomes the story. Forget about the story about what you think of me. I will never recover from that because killed somebody because I needed to check a tweet. These are moments in time.

So there are so many things that can keep you from being successful. Right? The people that you invested in, having something bad happen to them, so it slows you down. My friends, there are a million reasons why not, but there's one great reason why, which is you've just got to persevere, no matter what it is. It's just the way it is. It's hard being an entrepreneur. It's hard building a business. Everybody thinks it's so easy, that there's an entitlement. There's a disaster. Zinging China? Here comes my US zing right now.

There is an insane generation of 18 to 25-year-olds right now that think they're entitled to having a business because they saw The Social Network movie. Everybody has decided if you're a kid, and you know what tech is because you used Instagram early on, you're entitled to actually build a business. Building a business is hard. You know what makes it really hard? Everything that happens every day of every moment.

So you can pick time. You can pick money as the one or two things that you think stop you from winning your game, but the truth is there's a million reasons. 99% of businesses go out of business for a reason. That reason is it's hard. So if you're watching this show, I've got a sense of who you are. You need to start creating layers and layers and layers and layers of skin to be able to get through, because the glamour of being an entrepreneur.

You get very confused by my optimism because it's my optimism. I can't help it. It's just how I roll. It's probably one of the variable 1% reasons why I'm successful. But please, don't get it twisted. This is hard. Every day is hard. If you don't have the stomach to weather the storm, you will not be successful. By the way, let me throw you a real weird curveball, and that's okay.

People have to look themselves in the mirror and understand if they're a number two, three, four, five, six, seven in an organization that has differences of being a number one, but maybe that's where your skill set sits. Maybe that's how you make your fortunes and happiness and all the things that you're looking for.

So that question got me going a little bit, Steve, because it's under the context of excuses. I will never make an excuse. Everything that's a problem with me, everything I don't achieve, everything that's a problem with Vayner Media, everything is my fault. I succumb to that, and I respect that. I actually think that's the way it should be. So no excuses, my friends.

Question: When it comes to new platforms, emerging tech, you've always promoted the idea of being a first-mover. Some brands are usually very receptive to that. When it comes to campaigns though, some brands tend to focus on the idea of own-ability. My question is this. How ownable is that campaign to said brand? When does it become, at what point, a campaign ownable by being the first brand to do something, as in being the first mover to do that type of campaign?

Gary: I think we've seen it in our space. Right? Oreo kind of took control of the real-time content, and people keep bringing it up over and over. Here I am, two years later, bringing it up. So I think you can get first-mover advantage in that way.
Listen. This is going to get me in trouble. I think that's a bunch of marketing [beep] talk. When brands think they can own something, it just speaks to their naivety of the heavy fragmentation of the world we now live in. Right? You can own something for a moment, but to own it, there's no brand that's going to own, what brand owns what? Right?
I guess over 30 years of iconic marketing, Nike could own the sports space. But do they? Last time I checked, Under Armor is growing very quickly, and a million other things are happening in a world of Soul Cycle and Cross-Fit. There is no own-able. This is the naivety, the audacity, and just the lack of contextual understanding that brand managers and CMOs in corporate America think that they have the right to be able to own these things.
I think here's what you need to do as a brand, from an own-able standpoint. Can you, at this moment, own it, that it matters enough to your customer to make them buy your shit? Right? That's all you could ever ask for. I think people are way too romantic in marketing and thinking that they're gonna create the "Just Do It" or the Mastercard "Priceless," and it's gonna be this thing that they can put on their resume and kind of can live off of for the rest of their lives.
To me, it's much more about fragmentation. It's much more about being great at your last at-bat every time. I always say you're only as good as your last at-bat. Right? This show is doing well. If this episode sucks crap, it's heading in the wrong direction.
So I think that's how marketers need to think about that, which is do the best you can for what you need to do at that moment, on the platforms that you decide to story-tell, that actually drive business results, not this romantic feeling of, "Let's own it, marketing 360, fully integrated," all this jargon.

Question: What's the most important thing you've learned while growing your company at Vayner Media, from east coast to west coast? And how does a company successfully scale?

Gary: It's funny. I never opened a second Wine Library. So opening a second office in San Francisco and a third in LA has been a new phenomenon for me. Quite honestly there are challenges in it. Obviously I want to be everywhere. Right? That matters so much. But look. Even at Vayner Media, I'm not sure the last time I was on the 15th floor. Everybody is asking for an episode of the 15th floor. I haven't been on the 15th floor in a week, in a month. Excuse me.
It's a challenge when you're one human being. So for me, so much of it is high touch and the way I want to scale. To answer your second part, how do you scale a company? I actually think you scale a company by doing unscalable things, because I really believe you have to know your business. So at Wine Library, I didn't need a lot of people, and it was about selling wine. Thus, it was a different company.

Here, we sell people. We sell our hours against the scope and our thinking. So all I've got is people. So for me, scaling this company has been doing everything that's unscalable, which is sitting down and mentoring one-by-one and spending as much time as I can and trying to empower people to feel comfortable with coming to me, now starting to build out an HR department after a nine-month search, finding Minnie and saying, "Okay. This is a person I'm willing to build and think has the natural nuances to build the culture and the HR and EQ that I want for this organization," and then having people that have been with you for three and a half years.
The way for me to really scale it has been deeply entrenching myself into the people that work with me, for me, alongside me. That's very important to me. Communication is the backbone of this whole execution.

So more time, more physical time, something Lizzy and I are speaking about, of how much time I'm gonna spend on the west coast in '15 and '16 as a big commitment to me. So just hacking, hacking away at the thing that matters the most, which is: do I have a relationship with all 400 people? When it's 4000 people, do I have a relationship with all 4000 people?
I understand the cynicism that one could have, listening to that answer, of, "How could you possibly have that?" The way you have it is by having a relationship with the first 40 people, and then having it with the next 400 people, because the stunning amount of some of the people in this room and outside this room and in San Francisco and LA, stunning amount of people that now helped me scale, because when somebody is struggling or, "Screw this place," or, "I don't believe Gary," they're quick to jump in and tell 400 stories about why it's the other way, which then gives that person the ammo to maybe jump in and re-look at the situation a different way.

I always say the truth is undefeated. Right? So for me, scaling it is by delivering for your teammates.

Question: Hello, Vayner Nation. I work on new business and all things. I'm an account director here. I've been here about, I don't know, eight months now. It feels like a year almost. I'm real excited for my anniversary. So I wanted to ask a question which I think is going to help some of the entrepreneur viewers, but also just the future leaders of Vayner Media. When you're transitioning from that doer to a leader, knowing what your priorities are and where to put your focus so that it counts. Can you talk a little bit about that?

Gary: Yeah, I can. To put a little more color for everybody listening, at Vayner and a lot of other places, you get into a place where… I think you said it right. You're in execution mode. Then all of a sudden, you're managing a team. Those are two very different things. It's the thing that I most fear, any organization, period, end of story, because you have incredible executors who yearn for the financial upside and the title to then lead a team. Boy, are those two very, very, very, very, very, very, very, very, very, very, very, very, very, very, very different skill sets.
There's so many things people struggle with, with the transition. Number one, the thing I hate more than anything in the world, which is micro management. I want to kick micro management in the face. I hate it. It's something I just despise, and it's a major struggle because if you're a great executer, you know how to cross those Ts and dot those Is. When you see the person on your team who's not as strong at executing, you can't help it. Right? It goes against the grain. So that's number one thing.

Facing yourself in the mirror and understanding, I've talked to you about this, and I've talked to so many leaders in this company about this. This is where people get pissed at me. Most things don't matter, and that's a very tough mental transition to somebody that manages a team.  The other thing that a lot of people struggle with, and I talk about this quite a bit in the organization as well, is when you're a leader, you have to be the bigger man and woman in every situation. A lot of times, people, especially when they make that first transition that it's the first time they're the leader, they look at it wrongfully because of society, as, "I'm the boss." They try to impose their will instead of what I think the real skill set is, which is become a full-time listener, a full-time empowerer, a full-time "eat crap and have humility and empathy and self-awareness."  So you go from what I believe is IQ to EQ, and a lot of people can't make that transition. I think the reason this organization has grown so much is that's all I focus on when that transition happens. Don't try to put pressure on people for new business and client services and all the normal things one has to worry about. Now I'm the leader. Now this client has to respect me. I need to make Steve happy. I don't care about that. I can take care of that at the highest levels.

It's about really empowering people to become leaders. I love this. This is obviously a subject matter I love. We talked about it even in yesterday's episode. It takes so much more motherly, historically, stereotypical motherly skills to be a leader. I think people are confused. I think by default, people think it's fatherly stuff, and I think it's motherly stuff.  It's emotional skills that allow somebody to make that transition. Really one of the biggest factors in this whole thing is self-esteem. If you're not able to believe in yourself, nobody else is going believe in you. So I think one of the things is . . . Look. I got fortunate. I got a mother that instilled so much self-esteem in me that I'm still trying to get some of it out of me, so that I don't come across as an egotistical crap head.
But I think a lot of people don't have that, and a lot of people in my family don't have that. I see it. One of the weird little tidbits that I think could make this episode valuable is if you get into a leadership spot, and if you're self-aware enough to know that your mom or dad put you down your whole life, or society did, or you grew up as a minority, or whatever took self-esteem out of your body, or if it was never instilled in the first place, I think you need to find an outlet to create it.
I think you need to find an outlet to create it. I think one of the things that I focus on here is I instill it. You know? I instill it. I do talk 90% of the time about the positives. I just can't help it. I'm optimistic, and I just see it. I do see the good. It's what I do. There's always bad, but I think you need to seek it out. That may come in the form of extracurricular activities. You might be a great soccer player or an improv actor, or maybe the person you date, maybe you look for somebody who instills that. I think that's a very attractive characteristic.

I can tell you the reason I married Lizzy so quickly. It was because she was my mom. So I like coming home and having a cheerleader like, "You're great." I love that. I want that. So I think that those are things that come top to mind.

Question: Otto asks, "I like how you talk about execution in business. How do you prioritize which projects to execute first?"

Gary: Otto, great question. By the way, real quick, thank you, everybody, for getting me to 40. Also, all the people watching, I need you to get into the podcast. Podcast people, watch. I want people listening and watching every episode. Is that too much to ask? I think it's double consumption. That's a hashtag. I want to see if any of you use it on Twitter.

Otto, the way I prioritize is to equally, with my intuition, so it's a judgement call, equally take care of the things that are most on fire, the biggest problems, balanced with going on the offense on the biggest upside things and the biggest things, the culture, a new client. So take care of these three employees that are fighting, and they're not getting along, really on fire or a client that's really upset.  Then over here, strike the vision. What are we doing with the video department? Where are we going? What am I doing? Where's this all going? How do I buy the jets? Nothing in the middle. Otto, Vayner Nation, the middle is dangerous.


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