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

5 Aug 2026 · 41 min · 18 chapters

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In short

Gary Vaynerchuk (Gary Vee) discusses how he built VaynerX/VaynerMedia into a global “Mad Men 2020” digital-led communications business, how he invests in startups and buys/“reboots” brands, and how to grow on social by staying in your lane. He also covers email vs newer channels, segmentation, and why reputation and conflict-of-interest disclosures matter.

Guest backgrounds

Gary Vee is an entrepreneur, social media influencer, speaker, author, and investor. He grew up in his family’s wine/liquor business, became known via Wine Library TV and early web/social (mid-2000s), then built marketing/production/publishing operations (about 800 people across Singapore, London, NY, LA).

Key claims

Stay in your lane; share hypotheses/observations not “advice”; digital is “oxygen” but he’d rather reboot physical brands using digital DNA; email isn’t dead but needs context/segmentation; engagement improves with “new” channels like texting/community; reputation beats short-term incentives.

Notable examples

Early investments in Tumblr and very early Facebook (he says he bought Facebook stock early); meeting Twitter figures (Blaine Cook, Chris Messina) and advising David Karp; VaynerMedia created three 2020 Super Bowl ads; he recommends segmenting email (e.g., sending the same message repeatedly with different titles/offers) and mentions his 25,000 MailChimp list; he created a “Clean Gary Vee” version due to parents requesting profanity-free content.

Written by AI. May contain mistakes. Listen to the episode to check what was said.

Chapters

Tap a time to open that second in VO

Gary Vee's Elevator Pitch

1:02 to 1:54

Gary discusses his role and the structure of VaynerX.

“Well, it depends on what elevator I'm in, right?”

Transition from Wine to Agency

1:54 to 5:04

Gary shares how he shifted from the wine business to a marketing agency.

“I need Mad Men to be back and I'm only going to be able to use it for a couple more years.”

Vision for Future Acquisitions

5:04 to 6:28

Gary talks about his ambitions for buying brands and market predictions.

“I think everything's overpriced guy now.”

Emphasis on Physical Products

6:28 to 8:10

Gary explains his focus on traditional companies over digital platforms.

“And so that's kind of how I'm thinking about it.”

Investing Journey and Key Decisions

8:10 to 14:00

Gary recounts his early investments in tech and the evolution of social media.

“I think I need to buy a traditional company and use digital DNA to reboot the arbitrage.”

Choosing the Right Social Media Platform

14:00 to 16:20

Gary discusses which social media platform he would prioritize and why.

“Hey everybody, I hope you're enjoying the podcast right now.”

The Secret to Instagram Success

16:20 to 16:50

Insights on what it takes to thrive on Instagram and engage your audience.

“This episode is brought to you by Accenture.”

Staying in Your Lane on Social Media

16:50 to 18:56

Gary emphasizes the importance of sharing knowledge in familiar subjects.

“I think it's very important to speak about things you know and evolve, right?”

Finding Balance in Inspirational Content

18:56 to 20:28

Discussion on how to balance inspiration with practical advice in social media posts.

“I think my lane is practical entrepreneurship.”

The Influence of Cursing in Communication

20:28 to 22:37

Gary shares his thoughts on using profanity and its impact on authenticity.

“You're not doing any switches with JLo or anything like that?”
Show all 18 chapters

Creating a Clean Version for Younger Audiences

22:37 to 24:55

Exploration of why Gary created a curse-free platform for younger listeners.

“I'm not going to necessarily change or censor myself because I don't want to.”

The Future of Email Marketing

24:55 to 28:01

Gary discusses the evolving relevance of email marketing in the digital age.

“I think you probably will agree with me with this.”

The Shifting Landscape of Email Marketing

28:01 to 29:50

Learn about the decline of traditional email marketing and the rise of texting as a more effective engagement tool.

“engagement like I had in 1996 are over, but I don't think it's dead.”

Segmentation Strategies for Effective Email

29:51 to 31:08

Discover how to segment your email list for better engagement and tailored messaging.

“I think on email, if you segmented the list, the different titles, the different offers, the different opportunities, that's how you maximize it.”

The Value of Authenticity in Recommendations

31:09 to 33:18

Understand the importance of maintaining authenticity and transparency when recommending products or services.

“I don't want to send you emails every day.”

The Importance of Reputation in Business

33:19 to 35:10

Explore how reputation impacts business decisions and the long-term effects of prioritizing short-term gains.

“That was something very obvious to me too as well years ago.”

The Importance of Reputation in Business

35:44 to 36:11

Explore how reputation impacts business decisions and the long-term effects of prioritizing short-term gains.

“You sent a message, and it turned out the seller was super chatty, kind of funny, and an avid cyclist.”

The Balance of Influence and Authenticity

36:12 to 40:51

Discuss the delicate balance between influence and authenticity in marketing and personal branding.

“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.”
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Transcript

Automatic transcript. May contain errors.

0:00This is the Gary Vee Audio Experience.

0:08I'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. If you're interested in social media, entrepreneurship, marketing, and kicking butt, this is the episode of Remarkable People for You.

0:58I'm Guy Kawasaki, and this is Remarkable People. And now, here's Gary V.

1:08Give me the Gary V. elevator pitch. Well, it depends on what elevator I'm in, right? The main thing I do for a living is I'm the CEO 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 an 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. I like that. So in two words, you're Mad Men 2020.

1:58Yes, sir. I like that. Two words. I need Mad Men to be back and I'm only going to be able to use it for a couple more years. You're not going to know what that show is anymore. I need to go viral on Netflix. Like a two word elevator pitch. So how did you make this transition from flipping wine to becoming a thousand person agency? 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, 7, 8 was probably when the tech world or just this modern communication world started to hear about me.

2:35I 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 like deeply close, you know, 11 years younger than me. He's 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.

3:15I mean, just big companies. 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 going to 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 going to work for anybody. So why don't I start a business to service those companies? I'll make a couple bucks while learning fortune 5 ,000 land, which was very foreign to me because at that point I understood small family business life.

3:54I understood Silicon Valley, social media, web 2.0 dynamics, but I definitely didn't 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 going to 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.

4:43So I've been waiting for an economic downturn, not necessarily on the back of a pandemic, but just economic principles. And so 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 trade companies on multiples of EBITDA, Series D companies, private equity companies, just there's a lot of money in the world.

5:21And so I'll wait till there's 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. But when you say you're going to buy a company, are you talking about a Pepsi, General Motors? I don't think I'm going to get to that level. But at the time when I thought about it, I thought that I would buy like Blowpop or K-Swiss, the sneaker, like a small, nice$200, $150 million business. Big. I was sitting on a lot of Facebook stock, very early Facebook stock.

6:01I 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 reputation. I would let me raise capital if I needed. What's happened, guy, is that my ambitions for like something that would cost me a hundred million are probably now sitting 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 pepsi co but could it be buying sierra mist it's not gonna be buying unilever but could it be buying small swabs a big brand like like basically ultimately now can i buy instead of something that trades on four or five x revenue or six x revenue could i buy something that trades on one x revenue at the tune of 300 million dollars now instead of 40 million dollars or $100 billion?

6:57Yeah. 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, maybe that becomes$2 billion. And all of a sudden, it goes from K-Swiss to Puma. And so I don't know. 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. And of all the companies you've mentioned, none of them are digital platforms. Everything has a physical product. That's right. I'm not the inventor of Facebook and Uber. And I'm, and I don't think I want to reboot my space or friendster or, or anything like that.

7:40I 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. 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. 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 to buy a traditional company and use digital DNA to reboot the arbitrage. You talked about investing in Tumblr and Facebook. How did you pick those investments?

8:26And 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 SEMSEO 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, two, three, four. And I was devastated because I wasn't capable of writing. And I knew that this blogging thing was gonna be huge. And I watched very carefully as you and Waxy.org and Neil Dash, Andy Bio and Slashdot and Dig and all these written base internet things that were happening.

9:09I was like, man, that's next. And these guys and gals are gonna 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 kind of 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.

9:50The podcasting thing seemed interesting to me, but it was YouTube. 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 onto a bigger talent than being a wine retailer. I was right about e-com. I was right about email. I was right about Google AdWords. I've been right about the blogging revolution, though I didn't participate. and now I was participating and write and winning on YouTube, which really gave me a lot of confidence going into social. I was watching Friendster.

10:23I started getting serious about doing a little bit on MySpace as a business, not as a human. And so when Twitter and Facebook, and when 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. And I decided that when YouTube sold to Google for$1.7 billion, and 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.

10:551.7 billion in 2006 or seven, whenever that went down, that was like, 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 going to, I'm going to 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. And, uh, I went to South by Southwest 2007 and met Blaine Cook, the original CTO of Twitter.

11:32And 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 I 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 at 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.

12:06And me, Kevin Rose and Fred Wilson bought all his equity. And then I was meeting with David Karp a lot in New York because that was the big New York social network. It kind of advising him from my, 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 was a unique character in Web 2.0 and 06, 07 because I didn't come from hardcore tech. I didn't come from geek tech TV. I didn't come from the blogosphere talking about technology. I was coming at a complete left field as a wine video blogger, but I was a businessman and a marketer and more of a social anthropologist than I realized at the time, 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.

12:59So 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. and then i got very close with facebook and mark zuckerberg and dave morin and some of those men and women and uh 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.

13:43That 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.

14:07Hey 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. If you were limited to one social media platform, which one would it be? 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. As opposed to TikTok? 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.

14:49But to answer your question properly, like in truth, if this was the moment, that would be what I would hold on to. Okay. And do you have any - 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. And are you, are you using some kind of social media tool to do this or you're just on the Instagram app?

15:23I'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. If you look, Facebook, Twitter, TikTok, community, which is my texting platform, Instagram, YouTube, LinkedIn, Snapchat. So, you know, really good insight to how deep I am and it's all native. What's your advice for being an Instagram god? I mean, what does one do? 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 too while I'm on your show, because let's just get very basic on this.

16:04You 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. This episode is brought to you by Accenture. When your advertising operations fall out of sync, Everything else follows. Spotify and Accenture are working together to reinvent the rhythm of ad sales, using automation, analytics, and smarter workflows to simplify campaign delivery and access better data across the business. The result?

16:40Less time spent on operations, more time connecting brands with the moments and fandoms that matter most. Learn more at Accenture.com slash Spotify. 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.

17:25A, I don't think that I'm right or give advice ever. I think I'm sharing opinions, hypotheses, and observations. 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.

18:00And 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. 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.

18:39And 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. And how do you define your lane? I think my lane is practical entrepreneurship. But practical entrepreneurship, that doesn't exactly parse two beautiful pictures on Instagram. Yeah, I don't think I'm doing beautiful pictures on this film. 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.

19:18It's me holding up sports cards. 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 add context to it, not just being there for inspirational posts. 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's 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.

20:17What 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. You're not doing any switches with JLo or anything like that? No. And I wish I could do switch like JLo 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 what's the first app you check in the morning 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.

21:00It's Instagram. It's Instagram DM. It's definitely Twitter. They're all happening pretty quickly. That group. This is while you're still in bed or this is? 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. Why do you drop so many F-bombs? 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.

21:43It'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 prefer you not curse. 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. Then why did you create the Clean Gary Vee podcast?

22:20So 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 kids started getting better grades and started dealing with a bully issue and he was like how is this happening and he's like I listened to Gary V 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 but by the way I also heard him drop an f-bomb the other day outside 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.

23:13I'm not going to 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 or, 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.

23:48And so I think I've tried to find a happy medium. 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. I try to correct, you know, I, I, a lot of times you'll see people say that when they're defending me. Like we really analyze 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.

24:28so 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 let's not be lazy that I'm so authentic because I curse, the end. Okay. 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.

25:05And we've seen many communicators, executives, presenters who you can tell they're forcing, they're 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 the way that I'm really me, not be like me. But on your TikTok, don't you swear a lot?

25:39And isn't that a youthful platform? 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 And literally, literally see them sharing Beyonce songs with cursing in it.

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26:18Yeah. Non-explicit, the explicit version. I'm like, hey, hypocrisy much? Well, maybe they're writing to Beyonce. Maybe they are writing to Beyonce. Did you like when Joe Biden told that guy you're full of shit? Yeah, that didn't bother me at all. To me, whatever your politics are, both left, right, and indifferent, to me 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 curse 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

27:20let's talk about email so is email dead or is email the best method yet 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 enabled AR VR environment, much like the written letter, it took a long time for smoke signals to be dead. I think it's going to take a long time for email to be dead.

27:59And 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, 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. 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 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.

28:37Yeah. So Gary, what am I missing? I mean, 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 am I missing? How do you move the needle? Okay. The question is, besides that rant, how do you move the needle anymore? 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 super phone 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.

29:24I 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. Well, they weren't Russian bots yet. No, they weren't. Or 1996, 97, 98 email where I was truly getting 90 % open rates and 53 % add to cart buttons to winelibrary.com and just crazy shit. So A, new, right? New stuff, text. B, context. What do 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.

30:16One of the things that you were very historically right about at the time that I was not doing seven, eight, nine years ago 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? 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.

30:49I think on email, if you segmented the list, the different titles, the different offers, the different opportunities, that's how you maximize it. So I have 25 ,000 people in a MailChimp email list. How the hell do I segment that? I think you start by sending an email to create segmentation. You, I would probably send fifth, 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, cause you're so great on video.

31:20I 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 one 25 ,000 or what I would probably do in that scenario is have one 25 ,000, which is kind of like the, you know, guy weekly, right? That you just kind of do your general thing. And then you've got your Apple enthusiasts, surfing enthusiasts, marketing enthusiasts, authors.

31:55I think you'd be very effective with that strategy guy. Okay. Thank you. Do I have to pay you for that? Nope, free. Free friend. How about a little speed round to wrap up? I do. I prefer these. This is how I wish all of life worked. I like that. No kidding, huh? It's like Tinder. Mac or Windows? Mac. iOS or Android? iOS. Chrome, Fox or Safari? Now Safari. Safari? I'm only on my iPhone. And even on that. Chrome is on your iPhone. I know. You're right. Notice how I answered? I know everybody uses Chrome on their iPhone. I don't. That's the truth. Wow. You're the only person I know who uses Safari.

32:38Okay. Oh, we're good. You and Tim Cook. Big shout out to Tim. We're going to like you. Maybe only you, Tim Cook, and Warren Buffett. Barbecue or sushi? Sushi. Podcast or blog? Podcast. Daniel Craig or Sean Connery? Sean Connery. Avocado toast or croissant? Avocado toast. Canva or Photoshop? Canva. Full disclosure, I'm an investor in Canva. Well, full disclosure, I'm chief evangelist. I gotta be authentic there. Well, the FTC would have pulled this podcast. You know, that's really funny. We were just talking about that. 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.

33:29So from 2006 on, I've always been very thoughtful of like disclosures and making sure there's context. 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 Gawala. What? Remember Gawala? Is that the fruit juice? No, Gawala was the four square. That's Oddwala. Remember Gawala, the Foursquare competitor? Never heard of it. When Foursquare came out, there was a competitor that was really design heavy and really great product called Gawala. It got very hot in Web 2.0 there for like a year. It was right when we started VaynerMedia.

34:08And 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 Gawala and others. And it would always say, Gawala, full disclosure, Gary's a personal investor. And once every two times, the client would be like, hey, you're an investor in Gawala? I'm like, yeah, they're like, so why are you recommending Foursquare? I'm like, because you're paying me for advice.

34:42And like, sure, I prefer Gawala 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 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 this episode is brought to you by Accenture when your advertising operations fall out of sync Everything else follows.

35:18Spotify and Accenture are working together to reinvent the rhythm of ad sales, using automation, analytics, and smarter workflows to simplify campaign delivery and access better data across the business. The result? Less time spent on operations, more time connecting brands with the moments and fandoms that matter most. Learn more at Accenture.com slash Spotify. This episode is brought to you by Facebook. So you were scrolling on Marketplace, and there it was, the bike you'd been searching for. You sent a message, and it turned out the seller was super chatty, kind of funny, and an avid cyclist.

35:55The next thing you know, you're in a cycling crew. Well, a community cycling group. The thing about Facebook, you might find more than what you're looking for. From a browse to a bike ride, this summer, find more on Facebook. isn't that the beauty of canva that you and i can recommend that all day long knowing that it truly is the best well that's that's what i you know cam 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.

36:35I'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. Before we get off topic about this disclosure of conflicts of interest. 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?

37:22It must be good. A hundred percent. Yeah. I mean, I've always told these influencers five years ago, like when it was a really emerging smaller you know we're like professional professional like you know uh 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 reputation i'm sure a lot of people have asked you to be the chief evangelist of their company through the last 20 years.

37:56And 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, 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. Do you think that Matthew McConaughey really drives a Lincoln Mercury? Right. That's a good point. Actors and actresses with what they do on commercials.

38:30I 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, I've only, 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.

39:06And 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. Well, I'm waiting for the Gary V hot and cold ice pack. I'm going to work on it. Okay. Yeah. I will be your first customer, Gary. Starting now. Any closing words? First of all, if you're a listener of Guy's podcast, I've had the plumberage of really watching him for the last 15, 20 years. So I'm, I'm very aware of the thoughtfulness and like well-rounded nature of the listener of this.

39:52So A, thank you for listening. B, I really think self-awareness is a big game. I think about guys, you know, both guys 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 our, 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 is we may be very different in the way we communicate energy wise articulation, but that's right.

40:35But 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, and then deploying that, not trying to be like guy, 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, uh, in both of our communities, cause 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.

41:05Just 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 those are my two cents of wisdom on the way out. That's more like$2 million worth. Thank you for telling you that. In a sense, there's some irony there, right? In a sense, you're saying, don't be a parrot. And we're, quote, thought leaders that people want a parrot. So we're telling you not to do that. That's where I think I brought the most value to my audience. I think 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.

41:39And I think 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 40K 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.

42:10And thanks for being part of this journey. See you later.

From the publisher

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

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