The #1 Way to "Make The Most Out Of It"

In this episode of The GaryVee Audio Experience, I sit down with Guy Kawasaki on his Remarkable People podcast to talk about the discipline of staying in your pocket and only speaking about what you know. I share why digital is now oxygen — and why I want to reboot nostalgic physical brands instead of buying digital companies. I also discuss why reputation is everything, why context beats aggregation on every platform, and why self-awareness is the most powerful force in the world. You'll learn about: • Why You Should Stay in Your Lane • How Context Beats Cross-Posting • Why Email Is Dented, Not Dead • Reputation as the Long Game • Self-Awareness as a Superpower

• 0:00Speaker 00

  This is the Gary Vee Audio Experience.

• 0:09Speaker 01

  I'm Guy Kawasaki and this is Remarkable People. This episode's guest is Gary Vaynerchuk, or more widely known as Gary Vee. He is an entrepreneur, social media influencer, speaker, author, and investor. He started in his father's liquor store business, but his goal is worldwide domination. At least buying the New York Jets. His current focus is VaynerMedia, a digital ad agency with large brands as customers. In fact, Gary's agency created three ads for the 2020 Super Bowl. Here's an interesting factoid you'll learn in this episode. Guess whose Facebook stock he bought?

• 0:50Speaker 01

  If you're interested in social media, entrepreneurship, marketing, and kicking butt, this is the episode of Remarkable People for you. I'm Guy Kawasaki and this is Remarkable People. And now, here's Gary Vee.

• 1:08Speaker 01

  Give me the Gary Vee elevator pitch.

• 1:10Speaker 00

  Well, it depends on what elevator I'm in, right? The main thing I do for a living is on the CEO of VaynerX, a holding company that owns VaynerMedia, owns PureWow and 137PM, owns VaynerSpeakers, Tracer. It's a marketing agency, infrastructure, where we do, we're really just Mad Men 2020, right? We're a advertising agency that is obviously very digital-led. We have a production facilities, publishers, and then about 800 people in an agency in Singapore, London, New York, LA. So mainly I'm the CEO and chairman of a communications service business.

• 1:54Speaker 01

  I like that. So in two words, you're Mad Men 2020?

• 1:58Speaker 00

  Yes, sir.

• 1:59Speaker 01

  I like that, two words.

• 2:02Speaker 00

  I need Mad Men to be back. And I'm only going to be able to use it for a couple more years because too many people aren't going to know what that show is anymore. I need to go viral on Netflix, like my two-word elevator pitch.

• 2:14Speaker 01

  So how did you make this transition from schlepping wine to becoming a thousand-person agency?

• 2:20Speaker 00

  You know, as you know, and some of the people in this audience that are listening know, I grew up in the wine business. The Wine Library TV thing on YouTube and Twitter in 2006, '07, '08 was probably when the tech world, or just this modern communication world, started to hear about me.

• 2:36Speaker 00

  I started investing in a lot of the startups. I did well. This is where you and I got to know each other. That whole Web 2.0 movement, shared my thoughts. Some of those thoughts around business became more obvious, more prevalent. My brother AJ, who's more than just a brother to me, we're just deeply close, 11 years younger than me, is coming out of school. It's '09, post, we're only seven, eight, nine months removed from the 2008 crash. And brands are starting to reach out to me and say, "Hey, why do you have 400,000 followers on Twitter and we don't have a Twitter account?" Real brands like Pepsi and Campbell's and Mondelez and ESPN, I mean, just big companies.

• 3:17Speaker 00

  And so, I knew I wanted to build bigger businesses than the one I built for my dad, for myself, in this next chapter of my life. And I knew that I didn't know anything about corporate America. And I thought, you know what? If I'm gonna try to build big companies, I might as well take a little period here and learn the context from some of the biggest companies in the world. And I'm not gonna work for anybody, so why don't I start a business to service those companies? I'll make a couple bucks while learning Fortune 5000 land, which was very foreign to me, because at that point, I understood small family business life. I understood Silicon Valley's social media, Web 2.0 dynamics, but I definitely didn't

• 4:01Speaker 00

  understand GE or Pepsi or Chase. So we started the company with the hope of eventually, my biggest hope was to buy nostalgic brands and reboot them. So, I thought I would start the company, and in five years, the economy would collapse again, and during that time, I would buy something on the cheap and shut down my agency, take some talent that I had, and be on my merry way. I thought that Netflix and Amazon and Facebook were gonna disrupt the world dramatically. And I thought Wall Street would continue to reward people for cost cutting, not growth of business. And everything that I thought in 2009 was right, except the economy still hasn't collapsed.

• 4:43Speaker 00

  So I've been waiting for an economic downturn, not necessarily on the back of a pandemic, but just economic principles. And so what, everything's been in play the same way since. I think the thing that I didn't realize was I was going to be able to make a bigger impact on Madison Avenue than I thought, and I would be in it longer than I thought. And that's kind of where we're at now. That's how we got to 1,000 and global. I'm on my mission. I think everything's overpriced, Guy, now. Startup valuations on day one, publicly traded companies on multiples of EBITDA, Series D companies, private equity companies, just, there's a lot of money in the world. And so I'll wait till there's

• 5:23Speaker 00

  a correction. I'm patient. I'm a young man. I'm 44 years old, so I've got time. I think people are impatient when they're up to their missions in life, let alone business. And so that's kind of what I'm doing, mister.

• 5:36Speaker 01

  But when you say you're gonna buy a company, are you talking about a Pepsi, General Motors?

• 5:41Speaker 00

  I don't, yeah, I don't think I'm gonna get to that level. But at the time when I thought about it, I thought that I would buy like Blow Pop or K-Swiss, the sneaker company, like a small, nice 200, 150 million dollar business. Big. I was sitting on a lot of Facebook stock, very early Facebook stock. I was confident that that would work out. I believed in myself that I would save money. I've done a lot of things that I thought I would. Tumblr was a nice exit for me. I was in very early. So there was things brewing that made me confident that I would have some cash and then I would continue to build a reputation that would let me raise capital if I needed. What's happened, Guy, is that my ambitions for like something that would cost me 100 million are probably now sitting

• 6:25Speaker 00

  today at something that may cost me 500 million to a billion. Big percentage of my own money, big percentage of some outside monies. So I don't think it's as big as PepsiCo, but could it be buying Sierra Mist? It's not gonna be buying Unilever, but could it be buying, well, Swab's a big brand. Like, like, basically, ultimately now, can I buy, instead of something that trades on 4 or 5X revenue or 6X revenue, could I buy something that trades on 1X revenue at the tune of 300 million dollars now instead of 40 million dollars or 100 million dollars? Yeah. And so that's kind of how I'm thinking about it. But the truth is, if this goes another five to seven years... And I continue to grow in other areas.

• 7:06Speaker 00

  Maybe that becomes 2 billion and all of a sudden it goes from K-Swiss to Puma. And so I don't, I don't know. That, that's kind of out of my hands. That's when will the world do its correction? Where will I be sitting with liquid and relationships to capital?

• 7:22Speaker 01

  And of all the companies you've mentioned, none of them are digital platforms. Everything has a physical product.

• 7:29Speaker 00

  That's right. I'm not the inventor of Facebook and Uber and I'm, and I don't think I want to reboot MySpace or Friendster or, or anything like that. I want to reboot physical things. Like I'd rather buy Pete's Coffee Chain. I'd rather buy Blow Pops. I'd rather buy Ocean Pacific Timberland Boots.

• 7:53Speaker 01

  So that is, I don't know if it's ironic, it's surprising to me that you would think that Gary Vee, Mr. Digital Ninja would buy a digital company, not somebody making sneakers.

• 8:04Speaker 00

  For me, everything's digital, right? So to me, digital is now oxygen. So I don't think I have to buy a digital company. I think I need, I need to buy a traditional company and use digital DNA to reboot the arbitrage.

• 8:19Speaker 01

  You talked about investing in Tumblr and Facebook. How did you pick those investments?

• 8:26Speaker 00

  And so in 1996, for context for new listeners, I launched an e-commerce wine business. That really grew my family's business. I, email marketing and Google search SEM, SEO really was a big backdrop of my growth in the early 2000s. Then, and you'll appreciate this because you did it as good as anybody, then blogging hit the scene, right? In 2001, 2, 3, 4, and I was devastated because I wasn't capable of writing. And I, I knew that this blogging thing was going to be huge. And I watched very carefully as you and waxy.org and Neil Dash, Andy Bio and Slash Dot and Dig and all these written base internet things that were happening.

• 9:10Speaker 00

  I was like, man, that's next. And these guys and gals are going to win and they did. Many people built real things on it. And so that was like the one chapter of the tech revolution of the last 20 years that I kinda had to watch because I didn't have the ability to produce. Because I just really, still to this day, don't have the writing ability. My books, I record and then a ghostwriter structures it and transcribes and helps me structure it. So for me, when YouTube came out, it really changed my life. Like first it was Odeo. Ev Williams is one startup that probably didn't work. And then quickly after that, why it didn't work, the Apple podcasting. The podcasting thing seemed interesting to me, but it was YouTube.

• 9:54Speaker 00

  I started the wine show right away because I thought YouTube was the next thing. When YouTube established itself as the next thing, that also gave me double confidence that I was on to a bigger talent than being a wine retailer. I was right about e-comm, I was right about emails, I was right about Google AdWords. I'd been right about the blogging revolution, though I didn't participate. And now I was participating and right and winning on YouTube, which really gave me a lot of confidence going into social. I was watching Friendster, I started getting serious about doing a little bit on MySpace as a business, not as a human. And so when Twitter and Facebook started evolving from just college, but especially with Twitter, I was like, this is next, this is it. This is the next chapter of the internet.

• 10:39Speaker 00

  And I decided that when YouTube sold to Google for 1.7 billion dollars, and guy, you were so in the mix at this time, so you know this, please tell these youngsters that are listening, that number seemed like a trillion dollars. Yeah. 1.7 billion in 2006 or '07, whenever that went down, that was like... Amazing, yeah. It was a huge number. And then I was reading about Ron Conway and others making some money on their angel investors, and I was like, what's an angel investor? And I Googled it, and I was like, wait a minute. Instead of being right and helping my dad build his business for him on these innovations, I'm gonna, I'm gonna invest. I've got a couple bucks saved up, I've spent no money on anything for the last 10 years, let me invest it.

• 11:24Speaker 00

  And I went to South by Southwest 2007 and met Blaine Cook, the original CTO of Twitter. And then I went to San Francisco and met up with Chris Messina, Factory Joe, at a coffee shop, and he took me to Twitter's office when they had eight employees, and I built some relationships there. And when Blaine... Either, you know, I don't know the story, I really actually don't. Whether he got forced out, because if you remember Twitter was always going down. Whether he got forced out or not, when he was moved along as CTO, he got very passionate about selling all his shares. I spent a lot of, I would say more than three phone calls in three hours convincing him not to do that. He didn't listen, and me, Kevin Rose and Fred Wilson bought all his equity.

• 12:10Speaker 00

  And then I was meeting with David Karp a lot in New York, because that was the big New York social network. And kind of advising him, from my part, advising, that's not fair, sharing with him thoughts that I was seeing. He was interested in it, because he was coming from a different perspective. I was really one of these, and you know this guy. I, I was a unique character in Web 2.0 and 0607, because I didn't come from hardcore tech. I didn't come from geek, geek tech TV. I didn't come from the blogosphere, talking about technology. I was coming out of complete left field, as a wine video blogger. But I was a businessman, and a marketer, and, and more of a social anthropologist than I realized at the time.

• 12:52Speaker 00

  Which led to a lot of people listening to me, at least, not that I was right or wrong, but I was creating thoughtful conversations. So Tumblr offered me equity in their, think about how different the world used to be. They allowed me into their B round at a $14 million valuation.

• 13:10Speaker 00

  And then I got very close with Facebook, and Mark Zuckerberg, and Dave Morin, and some of those men and women. And somewhere in 2008, Randy, Mark's sister, called me and said, "Mark and I are curious if you're interested in some equity. You've been such a good part of the family, we know you don't have any. Our parents are selling some equity, because they want to buy a house on the West Coast, to be closer to us when they can." I mean, she didn't even finish the first word of the sentence, "I wired the money." And that was the biggest investment I ever made, and the most confident I've ever been in an investment. And that's how I got into it.

• 14:07Speaker 00

  Hey everybody, I hope you're enjoying the podcast right now. Make sure you follow the podcast. That's why I'm interrupting. Let's keep going on this show, but follow the podcast. It'll make my mom super happy.

• 14:17Speaker 01

  If you were limited to one social media platform, which one would it be?

• 14:21Speaker 00

  That's a great question. If I was limited today to one social network, what would it be? I would probably still say Instagram at this moment. It just has too big of my audience there. I can direct message, so I can engage. I would say Instagram still.

• 14:37Speaker 01

  As opposed to TikTok?

• 14:39Speaker 00

  As opposed to TikTok. TikTok is the most important emerging platform, has the potential, if the product evolves over the next half decade, to take that spot. But if, to answer your question properly, like in truth, if this was the moment, that would be what I would hold on to.

• 14:55Speaker 01

  Okay, and do you have any?

• 14:57Speaker 00

  Twitter would be hard for me to let go of, because it is no question where I'm most native in my interaction. I replied or engaged with somebody on Twitter every single day for the last 13 years. So it's hard for me to give that one up, but no question, it would be Instagram, because what I would do is probably start replying to every comment in my Instagram.

• 15:16Speaker 01

  And are you, are you using some kind of social media tool to do this? Or you're just on the Instagram app?

• 15:23Speaker 00

  I'm native. If you look at my, I'll give you my phone, there you go. If you look, it's all native. If you look at my phone, I think phones are really a big tell on somebody's life.

• 15:32Speaker 01

  Yeah.

• 15:32Speaker 00

  If you look, Facebook, Twitter, TikTok, Community, which is my texting platform, Instagram, YouTube, LinkedIn, Snapchat. So you know,

• 15:42Speaker 01

  Okay.

• 15:43Speaker 00

  Really good insight to how deep I am, and it's all native.

• 15:46Speaker 01

  What's your advice for being an Instagram god? I mean, what does one do?

• 15:52Speaker 00

  I think they come, you know, goddesses come in many forms on Instagram. I think it comes down to staying in your pocket. I'm going to take advantage of giving you a compliment or two while I'm on your show because let's just get very basic on this. You are a legend in this industry of like technology and communication. I think something you've done remarkably well, which is what makes you relevant today as you were a decade ago, as you were a decade prior to that. I think people have to stay in their pocket.

• 16:20Speaker 02

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• 16:50Speaker 00

  Okay. I think it's very important to speak about things you know and evolve, right? So there's so many subject matters I'd like to talk about more. Cryptocurrency, cannabis, AI, 5G. There's a lot of things I'm dangerous in, right? I'm a headline reader. I know a little bit more than the average bear. But I think what has made me work on Instagram and every other platform for that matter is I'm very passionate of staying in my lane. And when I share my opinions and hypotheses, not when I'm thinking I'm right or giving advice. A, I don't think that I'm right or give advice ever. I think I'm sharing opinions, hypotheses and observations.

• 17:32Speaker 00

  And I think that's important because I think some people become audacious. And I think I speak in a way that may seem audacious, but I'm very careful with my wordsmithing and I do stay in those hypothesis, opinions and observation zone. Number two, I talk about things I know. Again, whenever I hit your radar back in that pocket, because it had to be in that era, I spoke about wine because I know about wine. And I spoke about business because I at that point already built a very big business. And I spoke about communication because I understood how social worked because I learned a lot on email marketing and watching blogging and that worked for me. And that's where I continue to stay. And I think what I'm good at is understanding context.

• 18:15Speaker 00

  So one thing that I think has also worked for me is I don't think about tools to aggregate my content across all different platforms because I think the context of the platform matters. So what I do well on Instagram is I understand the visuals and videos and written words that are more native to the consumer on an Instagram platform that may vary on LinkedIn, that may vary on TikTok, that may vary on Twitter, and that's really worked for me. So it's been the content and the context and staying in a lane of what I know and believe, and that's really worked for me. Staying consistent, caring about my community, being grateful for any level of attention I've ever had, from the first follower to where I am today, and I think those principles have really worked for me.

• 18:58Speaker 01

  And how do you define your lane?

• 19:00Speaker 00

  I think my lane is practical entrepreneurship.

• 19:03Speaker 01

  But practical entrepreneurship, that doesn't exactly parse to beautiful pictures on Instagram.

• 19:09Speaker 00

  Yeah, I don't think I'm doing beautiful pictures on Instagram. As a matter of fact, every time I try to take a higher quality res, ironically, my latest post is a high-quality res photo. It's me holding up sports cards. I don't, I don't, people, I'm not doing well with a high-quality picture. I'm doing well when I'm putting out a quote and then writing seven sentences of copy that, that add context to it not just being there for inspirational.

• 19:34Speaker 01

  Bullshit.

• 19:35Speaker 00

  Yeah, I mean, like, listen, I believe in inspirational stuff because inspirational stuff is the manifestation of, of practical optimism, right? I believe, I believe in it. However, if you just post it without the seven sentences to contextualize it, which is like, look, being optimistic is a good idea, but sitting on your couch and sleeping all day and being optimistic is a problem. And so, you know, you may want to do something about it. So I think finding that balance of, of, that helps. But to your point, as a matter of fact, Guy, when I started getting very serious about Instagram four or five years ago, I got a lot of pushback from photography friends who were like, that's not what you're supposed to be doing on Instagram, as if there's a supposed to be.

• 20:17Speaker 00

  What I'm doing on TikTok is, I'm not dancing on TikTok either. And I've amassed an enormous following and impact there, and I'm putting out what I know, and so that's what I focus on.

• 20:27Speaker 01

  You're, you're not doing any switches with J-Lo or anything like that?

• 20:31Speaker 00

  No, and I wish I could do switch, like J-Lo and A-Rod did a good switch, and I'd like, I was thinking about doing one with G-Rock, believe it or not. Actually, I still might, actually, could I?

• 20:39Speaker 01

  What's the first app you check in the morning?

• 20:44Speaker 00

  The first app I check in the morning is my calendar app, my email app, and my text app to make sure there's no fires because I'm an actual CEO. As a human, it's, right now, it's eBay because I'm looking up sports card prices. It's Instagram, it's Instagram DM, it's definitely Twitter. They're all happening pretty quickly, that group.

• 21:07Speaker 01

  This is why you're still in bed, or this is?

• 21:10Speaker 00

  This is while I'm in bed, grab my phone, pick it up, walk, brush my teeth, poop, shower, come back out, keep looking at it, start dressing, keep looking at it, run to the, you know, out the door, keep looking at it.

• 21:23Speaker 01

  Why do you drop so many F-bombs?

• 21:26Speaker 00

  Why do I drop so many F-bombs? My intuition on that, my belief is because I cursed a lot as a kid because I grew up in a pretty diverse kind of lower to middle-class New Jersey neighborhood. And it's pretty much been embedded, it's how I've communicated my whole life. There's a lot of times where people get mad at me, or sad, or don't want to consume my content, that I think about it. There's been times early on in my career in 2009, 10, when I took the stage, where I tried not to, but I did. Anytime somebody reaches out and says, "Look, in this interview, or in this speech, or in this meeting, we'd prefer you not curse."

• 22:07Speaker 00

  That's very easy for me, I always take off my shoes if that's the rules of the house. But if I'm left to my being, I like communicating the way I communicate.

• 22:16Speaker 01

  Then, why did you create the Clean Gary Vee Podcast?

• 22:20Speaker 00

  So there's a curse-free YouTube channel, like your point, and podcast, because there was a lot of parents reaching out to me and saying that my message was really helping their children, and they were noticing that their kids were listening to me, and they started seeing good behavior. But they were noticing that the kids were hearing it either in the car when they thought they weren't paying attention. One guy wrote me a very long email. His kid would have headphones on, and he thought he was playing video games. But he found out about a month or two later, because the kid started getting better grades, and started dealing with a bully issue. And he was like, "How is this happening?" And he's like, "I listen to Gary Vee on the way to work with you." And he was stunned because the kid wasn't playing music. He was listening. But the kid was like nine, and he was like, "Gary, listen, that's been great, by the way, I also heard him drop an F-bomb the other day outside,

• 23:05Speaker 00

  and I'm not ready for all that. I'm a pretty good Christian boy, and we don't do that." And I'm like, and so like, I kept, you know, I always listen to feedback. I'm not gonna necessarily change or censor myself because I don't want to. There's no other real reason. But I wanted to give a platform for people who did enjoy my message, but not some of the words that I chose, the option to consume it. And a lot of teachers and educators and parents and counselors have been very grateful for that channel and been able to use it. And there's just a lot of general people who prefer to hear it beeped out. But you know, and so I don't think it's a good idea to create friction to the end consumer. I also don't think it's a good idea to change yourself for a small group of consumers. And so I think I've tried to find the happy medium.

• 23:50Speaker 01

  What about people who say Gary Vee is open and transparent and authentic and real? Because he swears. They seem to make this connection that profanity equals all those good things.

• 24:04Speaker 00

  I try to correct, you know. A lot of times you'll see people say that when they're defending me. Like, we really analyzed that data a little bit to see, are people saying I'm real, keeping it real, out of just left field? Or are they doing it normally? Or in response to take somebody shitting on me for saying it? And a far percentage was in response to when people get at me. So occasionally, if I feel like there's a little bit of that too much going on, I will, I have DM'd probably in the last decade, hundreds of people. And say, hey, there's an ungodly amount of people who don't curse that are as real as me, maybe more real than me. So let's not just be lazy. In the same way that some people are lazy that Gary's not intelligent because he curses.

• 24:49Speaker 00

  Let's not be lazy that I'm so authentic because I curse. The end. I think you probably will agree with me with this. You and I have seen many communicators and executives and humans that we know that don't curse, that are authentic and not authentic. And we've seen many communicators, executives, presenters, who you can tell they're forcing their cursing and other people it comes easy to them because it is their authentic self. And I think one thing I fear of is as my profile has grown, that there's some youngsters coming up the ranks who are forcing cursing because they think that's what's working, not that I know what I'm talking about. And so I think it's important for me to communicate that. That what you need to do is be, what you need to be good at is being really you,

• 25:33Speaker 00

  the way that I'm really me, not be like me.

• 25:37Speaker 01

  TikTok, don't you swear a lot? And isn't that a youthful platform?

• 25:41Speaker 00

  Uh, my TikTok audience is skewing well over 18 by average. So yes, do I think there's 12 and 13 year olds that catch me cursing on TikTok? Yes. Do I think there's a single 13 year old in America? That hasn't heard that word 43 times a day in their school? Let alone what they're doing on their computer? I mean, I think it's laughable. I mean, I literally have parents. This is real now. I've had parents tweet me being mad at me for cursing. And then I'm a funny guy. You know, I'm a little bit of a weird character in this way. I then go into their Twitter account and literally, literally see them sharing Beyonce songs with cursing in it.

• 26:18Speaker 01

  Yeah.

• 26:18Speaker 00

  Non-explicit, the explicit version, I'm like, hey, hypocrisy much?

• 26:24Speaker 01

  Well, maybe they're writing to Beyonce.

• 26:26Speaker 00

  Maybe they are writing to Beyonce.

• 26:28Speaker 01

  Did you like when Joe Biden told that guy, you're full of shit? When he?

• 26:33Speaker 00

  Yeah, that didn't bother me at all. Like to me, like whatever your politics are, like both left, right, and indifferent. To me, I don't, I am not struggling with somebody communicating one way or the other. I also think it's funny. The hypocrisy runs so deep on these conversations. I've had friends who are on both sides of the aisle, who get super bent out of shape. Especially because I'm the cursed guy. I guess I get dragged into these conversations. And I'm always telling them, your guy and gal did the same thing yesterday. So let's like, let's be very thoughtful here.

• 27:20Speaker 01

  Let's talk about email. So is email dead or is email the best method yet?

• 27:24Speaker 00

  Email is an evolving product that I don't know if it's best method yet. And if you're trying to reach all your 18 year old employees, audience, you're not going to crush that. But you know, I mean, look, writing a letter isn't dead. It's dented, but it's not dead. So I don't think email being dead is ever going to happen in our lifetime. It may get dented, but even if we have a voice in AR VR environment, much like the written letter. It took a long time for smoke signals to be dead. It, you know, it's, I think it's gonna take a long time for email to be dead. And I think it's a meaningful communication portal. I think for people that market on it, the days of 90% open rates and engagement like I had in 1996 are over.

• 28:07Speaker 00

  But I don't think it's dead and I don't think it's the killer app. I think it's a really nice part of the equation.

• 28:14Speaker 01

  So I have done marketing, email programs, I've done advertising programs, et cetera, et cetera. And to my utter amazement, in a recent advertising program, the, the people who ran my ads said that I have a half percent click through rate. Okay. And they were celebrating, they were telling me, oh my God, you're 2X what our usual is. Yeah. So Gary, what am I missing? I mean, in, in what sport, in what human endeavor do you say to somebody, you're crushing it? You're getting one out of 200. I mean, that's like, you know, Shaquille O'Neal is a better free throw shooter. Like, what, what am I missing? How do you move the needle? Okay, the question is, besides that rant, how do you move the needle anymore?

• 28:59Speaker 00

  You move the needle by two ways. One, finding the quote unquote new email, which I think is texting. So I don't know if you've seen Community, the app, or Superphone, or all these other platforms. But I have not seen engagement and results like I see on my community list, which is a texting platform where I text inspirational, random thoughts, insights, things that I think are important, links to something that might be important to me. I haven't seen these kind of engagement numbers since very early Twitter, when I had 8,000 followers and 7,000 of them did something with what I posted.

• 29:34Speaker 01

  Well, they weren't Russian bots yet.

• 29:36Speaker 00

  No, they weren't. Or 1996, 97, 98 email, where I was truly getting 90% open rates and 53% add to cart buttons to wine library.com and just crazy shit. So A, new, right? New stuff, text. B, context. What I mean by that? I bet you if you didn't just email the entire list, but you emailed the list in 437 different ways and sliced and diced with different offers, different opportunities, because you knew your list better and you actually sent them something that was more interesting to them, it'd be less dropping a bomb and hoping it lands on some people and more very hand-to-hand combat. One of the things that you were very historically right about at the time that I was not doing seven, eight, nine years ago

• 30:21Speaker 00

  was you would tweet the same thing over and over because you were smart enough to realize that not everybody sees it every time, right?

• 30:28Speaker 01

  Yeah.

• 30:29Speaker 00

  I agree with that. One of the things that I think I did really well was I understood that using something like Hootsuite or something else to post the same thing everywhere didn't maximize the upside of each of those platforms and contextual creative per platform, taking in the psychology of the end user, the nuances of it and the functionality of that platform would maximize. I think on email, if you segmented the list, the different titles, the different offers, the different opportunities, that's how you maximize it.

• 30:56Speaker 01

  So I have 25,000 people in a MailChimp email list. How the hell do I segment that?

• 31:01Speaker 00

  I think you start by sending an email to create segmentation.

• 31:06Speaker 01

  Okay.

• 31:06Speaker 00

  I would probably send, I would send the same email 10 days in a row of saying, hey, I don't want to send you emails every day. I want to send you emails that bring you value. That's what I would title it. And then you would have an email and they're written and then, because you're so great on video, I would probably embed a video there and be like, hey, everyone, like, hey, I don't want you to get email from me that you don't want. So here's a link with a survey and I'm going to put you into different email lists. And you maybe start a Google form with 11 different questions and maybe you create 10, 2,500 email lists instead of 125,000. Or what I would probably do in that scenario is have 125,000, which is kind of like the, you know, Guy Weekly, right? That you just kind of do your general thing.

• 31:49Speaker 00

  And then you've got your Apple enthusiasts, surfing enthusiasts, marketing enthusiasts, authors. I think you'd be very effective with that strategy, Guy.

• 31:58Speaker 01

  Okay, thank you. Not to pay you for that?

• 32:00Speaker 00

  Nope, free, free friend.

• 32:03Speaker 01

  How about a little speed round to wrap up?

• 32:05Speaker 00

  I do. I prefer these. This is how I wish all of life worked. I like fast.

• 32:10Speaker 01

  No kidding, huh? It's like Tinder. Mac or Windows?

• 32:15Speaker 00

  Mac.

• 32:16Speaker 01

  iOS or Android?

• 32:17Speaker 00

  iOS.

• 32:19Speaker 01

  Chrome, Fox, or Safari?

• 32:21Speaker 00

  Now Safari.

• 32:23Speaker 01

  Safari?

• 32:24Speaker 00

  I'm only on my iPhone. And even on that, I mean, I know.

• 32:28Speaker 01

  Chrome is on your iPhone.

• 32:28Speaker 00

  I know. You're right. Notice how I answered? I know everybody uses Chrome on their iPhone. I don't. That's the truth.

• 32:36Speaker 01

  Wow, you're the only person I know who uses Safari. Okay.

• 32:38Speaker 00

  Oh, we're good.

• 32:40Speaker 01

  You and Tim Cook.

• 32:42Speaker 00

  Big shout out to Tim, he's gonna like you.

• 32:44Speaker 01

  Maybe only you, Tim Cook, and Warren Buffett. Barbecue or sushi?

• 32:48Speaker 00

  Sushi.

• 32:50Speaker 01

  Podcast or blog?

• 32:51Speaker 00

  Podcast.

• 32:54Speaker 01

  Daniel Craig or Sean Connery?

• 32:56Speaker 00

  Sean Connery.

• 32:57Speaker 01

  Avocado toast or croissant?

• 32:59Speaker 00

  Avocado toast.

• 33:01Speaker 01

  Canva or Photoshop?

• 33:02Speaker 00

  Canva. Full disclosure, I'm an investor in Canva.

• 33:06Speaker 01

  Well, full disclosure, I'm chief advisor of Canva.

• 33:09Speaker 00

  I gotta be authentic there.

• 33:13Speaker 01

  Well, the FTC would have pulled this podcast.

• 33:16Speaker 00

  You know, it's really funny. We're just talking about that. Like, that was something very obvious to me too as well, years ago. I was always scared there'd be a tweet where I was promoting something that I had vested interest in, and it would ruin my reputation. So, from 2006 on, I've always been very thoughtful of disclosures and making sure there's context.

• 33:38Speaker 00

  Reputation is everything. I remember, here's a good story for you guys. I was an investor in a big one. I put some real money in for me at the time in Gowala.

• 33:46Speaker 01

  What?

• 33:47Speaker 00

  Remember Gowala?

• 33:48Speaker 01

  Is that the fruit juice?

• 33:50Speaker 00

  No, Gowala was the...

• 33:51Speaker 01

  That's Oddwalla.

• 33:52Speaker 00

  Remember Gowala, the Foursquare competitor?

• 33:55Speaker 01

  Never heard of it.

• 33:56Speaker 00

  When Foursquare came out, there was a competitor that was really design-heavy and really great product called Gowala. It got very hot in Web 2.0 there for like a year. It was right when we started VaynerMedia. And at that, it was a year earlier. And then a year later, we started VaynerMedia, and the location-based check-in marketing game was exploding because of Foursquare. And I remember going to... Clients and promoting that they should consider it. And we would always recommend Foursquare. And then we would spend two seconds on the landscape and we'd show Guala and others. And they would always say, Guala, full disclosure, Gary's a personal investor. And once, you know, once every two times, the client would be like, hey, like, you're an investor in Guala? I'm like, yeah. They're like, so why are you recommending Foursquare?

• 34:39Speaker 00

  I'm like, because you're paying me for advice. And like, sure, I prefer Guala to get their shit together and win. You know, I'm not going to push you on something that's inferior. And I always remember thinking back then how weird it was that they thought it was weird that I wasn't put. And I was like, man, fucked up. You know, like, why would anybody choose short term economics versus ruining their name in perpetuity? I'll never understand it. And so a lot of cynicism in business world makes me laugh because I'm like, people don't understand how important reputation is.

• 35:10Speaker 02

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• 36:10Speaker 01

  Isn't that the beauty of Canva that you and I can recommend that all day long, knowing that it truly is the best?

• 36:16Speaker 00

  Well, that's what I, you know, Canva was one of the last investments I made. I've tried to only invest in things like that. Like, you know, to me at this point, I mean, it's, believe it or not, it's weirdly why I'm in sports cards. I like recommending the things I do and I like doing them because I like having friends along the way to win with me. It's my kind of state. I've always been that guy. That's my DNA. So it's very hard to recommend startups these days because the inflection points of just complete, I mean, everyone's a startup founder, the valuations are through the roof, 99% will fail. It's not what it was in 06, 07 when you had, in my opinion, more true entrepreneurs doing more innovative stuff.

• 36:55Speaker 01

  You know, before we get off topic about this disclosure of, of conflicts of interest, my, my experience has been that the FTC is trying to prevent this situation like, oh, Gary Vee and Guy recommend Canva and they didn't tell us why. My experience is when Gary Vee or Guy recommends Canva, it creates more interest in Canva, not less, because people are saying, well, why are they involved in Canva? It must be good.

• 37:22Speaker 00

  100%, 100%.

• 37:23Speaker 01

  Right?

• 37:23Speaker 00

  Yeah, I mean, I've always told these influencers five years ago, like when it was really emerging smaller, you know, we're, we're like professional, professional, like, you know, communicator more than evangelist, in my opinion. I, I, I agree with you, but that we're like, to me, when it's a, I think what they're trying to do is a different thing, which is, um, you know, you've always had that evangelist title. That's been very clear and to your point, because you've always been behind real shit. You have real reputa-, I'm, I'm sure a lot of people have asked you to be the chief evangelist of their company through the last 20 years, and you've been smart enough, which is why you're still Guy, to say that sucks. You know, like, and so that's easy for us. I think what they're worried about is going on at scale on these influencers,

• 38:06Speaker 00

  which is like people are just hawking any product in the world for a $5,000 check. And I kept telling all these influencers five years ago, it's like, first of all, disclose it. Second of all, by the fifth thing that you promote that sucks, you're going to lose your audience.

• 38:21Speaker 01

  Do you think that Matthew McConaughey really drives a Lincoln Mercury?

• 38:25Speaker 00

  Right, that's a good point. Actors and actresses with what they do on commercials. I saw Tom Selleck last night, like promoting something like retirement shit. And I was just like laughing and I was like, I was like really trying to understand like, do I think Tom Selleck really believes in this shit? Or is he like super pumped about the million dollar bag that he's getting? Yeah, no, I don't know if Matthew McConaughey loves his thing. I like him, so I'm hoping he does like do the same thing you and I would do, which is like, I don't know. I've only done two business development deals in the history of my life with brands. One was with Tops for $25,000, which luckily for me at this point in my career is an afterthought because I got to have a baseball card.

• 39:06Speaker 00

  And one was with K-Swiss where I made an actual sneaker with my signature on it because I wanted to test my theory of turning around a nostalgic brand, which we did wildly successful. So I've never done an endorsement deal, but I've done these biz dev deals. And so it's been, I like learning from those.

• 39:23Speaker 01

  Well, I'm waiting for the Gary Vee hot and cold ice pack.

• 39:30Speaker 00

  I'm gonna work on it.

• 39:31Speaker 01

  Okay, yeah, I will be your first customer, Gary.

• 39:34Speaker 00

  Pre-orders, starting now.

• 39:37Speaker 01

  Any closing words?

• 39:38Speaker 00

  First of all, if you're a listener of Guy's podcast,

• 39:42Speaker 00

  I've had the privilege of really watching him for the last 15, 20 years. So I'm very aware of the thoughtfulness and like well-rounded nature of the listener of this. So A, thank you for listening. B, I really think self-awareness is a big game. I think about guys, you know, both Guy and I are very busy, but like we ran into each other very recently in Minnesota. We reach out to each other at times, we've done co-book signings, things. I think our fondness in what I would call our acquaintance slash friendship, we're just busy to like ever get enough time to go hardcore. But like the warm feelings I have for him and why he's here today. And the reason I'd like to think he respects and has warm feelings towards me and why I'm still around in a world where I think a lot of people 15 years ago thought I wouldn't be,

• 40:27Speaker 00

  is we may be very different in the way we communicate. Y wise articulation, but

• 40:33Speaker 01

  Death bombs?

• 40:33Speaker 00

  That's right. But I think the self-awareness matters. And I think if you're listening right now, really knowing yourself and feeling comfortable within your own skin and and then deploying that, not trying to be like I, not trying to be like me, just trying to be yourself for real, for real. And dealing with the collateral damage or upside that comes along with you authentically being you is a really big deal. I see a lot of you in both of our communities, because I've watched it for almost two decades now. Try to parrot too much of things that come natural to us that don't come to you. And that's why you're not getting the returns. Just really go, self-awareness is super powerful. It also leads to self-esteem, which I think is the most powerful force in the world. So that those are my two cents of wisdom on the way out.

• 41:14Speaker 01

  That's that's more like two million bucks worth, but

• 41:17Speaker 00

  Thank you for telling that.

• 41:18Speaker 01

  In a sense, there's some irony there, right? In a sense, you're saying, don't be a parrot. And we're thought, we're quote thought leaders that people want to parrot. So we're telling you not to do that.

• 41:30Speaker 00

  That's where I think I brought the most value to my audience. I think a lot of people, a lot of people are into my stuff, and I think a lot of people are not and have a lot of misconceptions around me. And I think it's, it's when you look under the hood, the deeper conversation around this specific issue. I think really has been something that I've been able to bring value, including things that I think I was branded in around like hustle and hard work and like burning out, that has never been my message. My message has been going hard at your one at bat at life and being self-aware. Even at my earliest content, I talked about working nine to five and making 40 K and being happy. Everybody, if you enjoyed this podcast, please go back and look at the prior episodes. They're loaded. I appreciate your attention and thanks for being part of this journey. See you later.