Gary Vaynerchuk: Investor, Serial Entrepreneur, and Author

Guy Kawasaki:
I'm Guy Kawasaki, and this is Remarkable People. This episode's guest is Gary Vaynerchuk, or more widely known as GaryVee.
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. I'm Guy Kawasaki, and this is Remarkable People. And now, here's GaryVee.
Guy Kawasaki:
Give me the GaryVee elevator pitch.
GaryVee:
Well, it depends on what elevator I'm in, right?
The main thing I do for a living is I'm the CEO of VaynerX, a holding company that owns VaynerMedia, PureWow, ONE37pm, VaynerSpeakers, and Tracer. It's a marketing agency infrastructure where we do…We're really just Mad Men 2020. We're an advertising agency that is obviously very digital led. We have production facilities, publishers, and then about 800 people in an agency in Singapore, London, New York, and LA. So mainly I'm the CEO and chairman of a communications service business.
Guy Kawasaki:
I like that. So in two words, you're Mad Men 2020.
GaryVee:
Yes sir.
Guy Kawasaki:
I like that. Two words.
GaryVee:
I need Man 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 it to be back on Netflix to keep my two-word elevator pitch.
Guy Kawasaki:
So how did you make this transition from schlepping wine to becoming a 1000-person agency?
GaryVee:
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, 2007, and 2008 was probably when the tech world, or just this modern communications world started to hear about me.
I started investing in a lot of startups, and 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, 11 years younger than me, he's coming out of school, it's 2009. We're only 7, 8, 9 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 Campbells, and Mendeley, ESPN. Just big companies.
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. 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? 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 understand GE, or Pepsi, or Chase.
We started the company with the hope of eventually, my biggest hope was to buy nostalgic brands and reboot them.
I thought I would start the company, and then 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.
Everything that I thought in 2009 was right, except the economy still hasn't collapsed. So, I've been waiting for an economic downturn. Not necessarily on the back of a pandemic, but just economic principles.
Everything has 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. That I would be in it longer than I thought.
That's where we're at now. That's how we got to 1000 in global.
I'm on my mission. I think everything is overpriced Guy, now. Startup valuations on day one, publicly traded companies on multiples of EBITDA, Series D companies, and private equity companies.
There's a lot of money in the world, and so I'll wait until there's a correction. I'm patient. I'm a young man. I'm forty-four 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.
Guy Kawasaki:
When you say you're going to buy a company, are you talking about Pepsi? General Motors? Comcast?
GaryVee:
I don't think I'm going to get to that level, but at the time, what I thought about it, I thought that I would buy like Blow Pop, or K-Swiss, the sneaker company. A small, nice $150 million business… big.
I was sitting on a lot of Facebook stock, very early Facebook stock, and 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 were things brewing that made me confident that I would have some cash. And then, I would continue to build reputation that would let me raise capital if I needed it.
What's happened, Guy, is that my ambitions for something that would cost me $100 million, is probably now sitting today at something that may cost me $500 million to $1 billion. Big percentage of my own money, big percentage of some outside money.
I don't think it's as big as PepsiCo, but could it be buying Sierra Mist? It's not going to be buying Unilever, but could it be buying Suave... Well, Suave's a big brand.
Basically, ultimately now, can I buy, instead of something that trades on 4.0-5.0x revenue, or 6.0x revenue, could I buy something that trades on 1.0x revenue at the tune of 300-million-dollars now? Instead of $40 million or $100 million? Yeah. And so that's how I'm thinking about it.
The truth is, if this goes another 5-7 years, and I continue to grow in other areas, maybe that becomes $2 billion. And then all of a sudden it goes from K-Swiss to Puma.
And so, I don't know, that's out of my hands, that's when will the world do its correction, where will I be sitting with liquid and relationships to capital.
Guy Kawasaki:
And of all the companies you've mentioned, none of them are digital platforms. Everything has a physical product.
GaryVee:
That's right. I'm not the inventor of Facebook and Uber, and I don't think I want to reboot MySpace, or Friendster, or anything like that. I want to reboot physical things.
I'd rather buy Peet's Coffee chain, I'd rather buy Blow Pops, I'd rather buy Ocean Pacific, and give them reboots.
Guy Kawasaki:
I don't know if it's ironic, it's surprising to me. You would think that GaryVee, Mr. Digital Ninja, would buy a digital company, not somebody making sneakers.
GaryVee:
For me, everything is digital, right? For 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.
Guy Kawasaki:
You talked about investing in Tumblr and Facebook. How did you pick those investments?
GaryVee:
In 1996, for context for new listeners, I launched an e-commerce wine business that really grew my family's business.
Email marketing and Google search SEM, SEO really was a big backdrop of my growth in the early 2000s.
Then, you'll appreciate this because you did it as good as anybody, then blogging hit the scene in 2001, 2002, 2003, 2004. And I was devastated, because I wasn't capable of writing.
I knew that this blogging thing was going to be huge. And I watched as carefully as you, and Waxy.org, and Neill Dash, Andy Baio, and Slashdot, and Digg, and all these written-based internet things that were happening.
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 the one chapter of the tech revolution of the last twenty years that I 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.
First it was Odeo, Evan Williams' 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.
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-comm, 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 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... 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 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 $1 trillion. $1.7 billion in 2006 or 2007, whenever that went down, that was like...
Guy Kawasaki:
Amazing, yeah.
GaryVee:
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 invest. I've got a couple bucks saved up. I've spent no money on anything for the last ten years, let me invest it."
I went to SXSW 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, 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.
Guy Kawasaki:
Mm-hmm (affirmative).
GaryVee:
Whether he got forced out or not, when he was moved along at ETO, he got very passionate about selling all his shares. I spent a lot of, I would say more than three phone calls, and three hours convincing him not to do that. He didn't listen. And me, Kevin Rose, and Fred Wilson bought all his equity.
And then I was meeting with David Karp a lot in New York, because the big New York social network, and advising him from my point... 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 in 2006 and 2007. Because I didn't come from hardcore tech. I didn't come from geek TechTV, 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 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.
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.
And then I got very close with Facebook and Mark Zuckerberg, and Dave Morren, and some of those men and women.
Somewhere in 2008, Randi, Mark's sister called me and said, "Mark and I are curious is 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.
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.
Guy Kawasaki:
Can I just follow you around and invest in what you invest in?
GaryVee:
Well Guy, you can follow me around. If you want to invest in right now... I highly recommend investing in sports cards, and I'm not even kidding.
Guy Kawasaki:
Sports cars?
GaryVee:
Cards.
Guy Kawasaki:
Oh, cards. You mean like Joe DiMaggio?
GaryVee:
Yes, but more modern day, like limited edition Lamar Jacksons.
Guy Kawasaki:
How does one invest in it? Go buy some?
GaryVee:
I know it's funny, and I know it's completely left field, but I promise you, when I was in the wine business, going to San Francisco to do computer stuff was left field too.
Let me just give you one comp: LeBron James rookie cards in April were $1000 apiece. And now they are $7000.
Guy Kawasaki:
Where does one even buy such things?
GaryVee:
eBay and StockX, and COMC, C-O-M-C, are three major platforms. I think the sneaker kids, the fathers of a generation with their sons and daughters... And gamblers, because of the way that sports cards are now...
And I think that for my generation, look, I'm a forty-four-year-old successful businessman. Look what I'm wearing right now. As you and I know, the "me" thirty-five to forty years ago was wearing a suit and tie.
I believe that sports cards, and comic books, and Pokémon cards are going to be the "art" found in the homes of a lot of these people, not something from the 1920s from Europe in painting form.
So, there's a lot of macrotrends that led me to believe two years ago the sports card market was going to go up. It's gone up more than I've predicted, and I think we're still 66 percent of the way there. So yes is the answer.
Guy Kawasaki:
Let’s just end it right here, I'll go to eBay.
If you were limited to one social media platform, which one would it be?
GaryVee:
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.
Guy Kawasaki:
As opposed to TikTok?
GaryVee:
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 to answer your question properly, in truth, if this was the moment, that would be what I would hold on to.
Guy Kawasaki:
Okay. And do you have any…
GaryVee:
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, what's that, 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.
Guy Kawasaki:
And are you using some kind of social media tool to do this?

GaryVee:
No.

Guy Kawasaki:
Or you're just on the Instagram app?
GaryVee:
I'm native. If you look at my… I'll give you my phone. Here 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, a really good insight to how deep I am, and it's all native.
Guy Kawasaki:
What's your advice for being an Instagram god? What does one do?
GaryVee:
I think they come, gods and 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 you, let’s just get very basic on this, you are a legend in this industry of 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. I think it's very important to speak about things you know, and evolve.
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. 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 my very passion 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.
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 observations zone.
Number 2, 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 had at that point already built a very big business. And I spoke about communication, because I understood how socials work, 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.
One thing that I think has also worked for me, is I don't think about tools to aggregate my contents 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.
Guy Kawasaki:
And how do you define your lane?
GaryVee:
I think my lane is practical entrepreneurship.
Guy Kawasaki:
But practical entrepreneurship, that doesn't exactly parse to beautiful pictures on Instagram.
GaryVee:
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'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...
Guy Kawasaki:
Bullshit?
GaryVee:
Yeah.
Listen, I believe in inspirational stuff because inspirational stuff is the manifestation of practical optimism. Right? 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 helps, but to a 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".
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.
Guy Kawasaki:
You're not doing any switches with J.Lo or anything like that?
GaryVee:
No. And I wish I could do switches... J.Lo and A-Rod did a good switch. I was thinking about doing one with C-Rock believe it or not. I still might, actually, today.
Guy Kawasaki:
What's the first app you check in the morning?
GaryVee:
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, 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.
Guy Kawasaki:
This is while you're still in bed, or this is...
GaryVee:
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 out the door, keep looking at it.
Guy Kawasaki:
Why do you drop so many f-bombs?
GaryVee:
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 2009-2010 when I took the stage where I tried not to, but I did.
Any time somebody reaches out and says, "Look, in this interview, or in this speech, or in this meeting, we'd 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.
Guy Kawasaki:
Then why did you create the clean GaryVee podcast?
GaryVee:
So there's a curse-free YouTube channel like your point. And podcast.
Because there's 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 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 their bully issues. And he was like, "How is this happening?", and he's like "I listen to GaryVee on the way to work with you," and they're 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, and I'm not ready for all that. I'm a pretty good Christian boy and we don't do that."
And I always listen to feedback. I'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 beeped out.
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.
Guy Kawasaki:
What about people who say "GaryVee is open, and transparent, and authentic, and real, because he swears."
They seem to have made this connection that profanity equals all those good things. That's not truth.
GaryVee:
I try to correct them.
A lot of times you'll see people say that when they're defending me. 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 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 have direct messaged probably in the last decade, 100s of people and said, "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."
Guy Kawasaki:
Okay.
GaryVee:
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 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 what you need to be good at, is being really you, the way that I'm really me. Not be like me.
Guy Kawasaki:
But, on your TikTok, don't you swear a lot? And isn't that a youthful platform?
GaryVee:
My TikTok audience is skewing well over eighteen by average.
So yes, do I think there's twelve- and thirteen-year-olds that catch me cursing on TikTok? Yes.
Do I think there's a single thirteen-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 literally have parents, this is real now, I've had parents tweet me being mad at me for cursing, and that 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 see them sharing Beyonce songs with cursing in it. The explicit version. I'm like, "Hey, hypocrisy much?"
Guy Kawasaki:
Well maybe they're writing to Beyonce.
GaryVee:
Maybe they are writing to Beyonce.
Guy Kawasaki:
Did you like when Joe Biden told that guy, "You're full of shit." When he...
GaryVee:
Yeah that didn't bother me at all. For me whenever 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 in these conversations. I've had friends who are 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 be very thoughtful here."
Guy Kawasaki:
Let's talk about email. So is email dead? Or is email the best method yet? Still.
GaryVee:
Email is an evolving product that, I don't know if it's the best method yet, and if you're trying to reach all your eighteen-year-old employees, audience, you're not going to crush that.
I mean look, writing a letter isn't dead. It'd 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.
You know, I think it's going to 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 percent 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 nice part of the equation.
Guy Kawasaki:
So I have done marketing in email programs, I've done advertising programs, etc. etc. 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. And they were celebrating. They were telling me, "Oh my God, you do X what our usual is."
So Gary, what am I missing? In what sport, in what human endeavor do you say to somebody, "You're crushing it. You're getting one out of 200." That's like, Shaquille O'Neal's a better free throw shooter.
What am I missing? How do you move the needle? The question is, besides that rant, how do you move the needle anymore?
GaryVee:
You move the needle by two ways. One, finding the quote, unquote "new email". Which I think is texting.
I don't know if you've seen Community, the app, or SuperPhone, or all these other platforms. But, I've 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.
Guy Kawasaki:
Well they weren't Russian bots yet.
GaryVee:
No, they weren't.
Or 1996, 1997, 1998 email, where I was truly getting ninety percent open rates. And fifty three percent "Add to cart" buttons to winelibrary.com. And just crazy shit. So A, new. 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 would 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, 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.
I think on email, if you segmented the list, did different titles, did different offers, did different opportunities, that's how you maximize it.
Guy Kawasaki:
So I have 25,000 people in a Mail Chimp email list. How the hell do I segment that?
GaryVee:
I think you start by sending an email to create segmentation.

Guy Kawasaki:
Okay.

GaryVee:
I would probably send the same email ten 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 then written, and then because you're so great on video, I'd probably embed a video there, be like, "Hey everyone, 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 eleven different questions and maybe you create ten 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 like the "Guy Weekly", that you do your general thing, and then you've got your Apple enthusiasts, surfing enthusiasts, marketing enthusiasts, and authors. I think you'd be very effective with that strategy, Guy.
Guy Kawasaki:
Okay. Thank you. Do I have to pay you for that?
GaryVee:
Nope. Free. Free, friend.
Guy Kawasaki:
How about so little speed round, to wrap up?
GaryVee:
I do. I prefer these. This is how I wish all of life worked. I like that.
Guy Kawasaki:
No kidding. That's like Tinder. Mac or Windows?
GaryVee:
Mac.
Guy Kawasaki:
iOS or Android?
GaryVee:
iOS.
Guy Kawasaki:
Chrome, Fox or Safari?
GaryVee:
Now, Safari.
Guy Kawasaki:
Safari?
GaryVee:
I'm only on my iPhone. And even on that-
Guy Kawasaki:
Chrome is on your iPhone.
GaryVee:
I know. You're right. Notice how I answered? I know everybody uses Chrome on their iPhone. I don't. That's the truth.
Guy Kawasaki:
Wow. You're the only person I know who uses Safari.
GaryVee:
So we're good.
Guy Kawasaki:
You and Tim Cook.
GaryVee:
Big shout out to Tim, they're going to like me.
Guy Kawasaki:
You, Tim Cook and Warren Buffett.
Barbecue or sushi?
GaryVee:
Sushi.
Guy Kawasaki:
Podcast or blog?
GaryVee:
Podcast.
Guy Kawasaki:
Daniel Craig or Sean Connery?
GaryVee:
Sean Connery.
Guy Kawasaki:
Avocado toast or croissant?
GaryVee:
Avocado toast.
Guy Kawasaki:
Canva or photoshop?
GaryVee:
Canva. Full disclosure. I'm an investor in Canva.
Guy Kawasaki:
Well, full disclosure, I'm chief evangelist.
GaryVee:
I've got to be authentic there.
Guy Kawasaki:
Wow. The FTC would have pulled this podcast.
GaryVee:
That's so true. That really funny, we're just talking about that. That was something very obvious to me too, 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. Reputation is everything.
I remember, here a good story for you, Guy, I was an investor, and a big one, I put some real money in for me at the time in Gowalla.
Guy Kawasaki:
What?
GaryVee:
Remember Gowalla?
Guy Kawasaki:
Is that the fruit juice? That's Odwalla.
GaryVee:
No, Gowalla was the Foursquare competitor.
Guy Kawasaki:
Never heard of it.
GaryVee:
When Foursquare came out, there was a competitor that was really design-heavy and really great product, called Gowalla. It got very hot on Web 2.0 there for like a year.
It was right when we started VaynerMedia. 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 Gowalla, and others, and they would always say, "Gowalla, full disclosure, Gary's a personal investor."
Once every two times the client would be like, "Hey, you're an investor in Gowalla?" I'm like, "Yeah." They're like, "So why are you recommending Foursquare?" I'm like, "Because you're paying me for advice. And sure, I'd prefer Gowalla to get their shit together and win, you know I'm not going to push you on something that's inferior.”
I always remember thinking back then, how weird it was, that they thought it was weird, that I wasn't putting... And I was like, "Man, that's fucked up." 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 people don't understand how important reputation is.
Guy Kawasaki:
Isn't that the beauty of Canva? That you and I can recommend that all day long, knowing that it truly is the best.
GaryVee:
Canva was one of the last investments that I made. I've tried to only invest in things like that.
Believe it or not, that's why I'm in sports cards. I like recommending the things that 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.
It's very hard to recommend startups these days, because the inflection points are just completely... Everyone's a startup founder, the valuations are through the roof, ninety-nine percent will fail. It's not what I was in 2006 or 2007, when you had, in my opinion, more true entrepreneurs doing more innovative stuff.
Guy Kawasaki:
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, GaryVee and Guy recommend Canva, and they didn't tell us why."
My experience is, when GaryVee 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."
GaryVee:
One hundred percent. I've always told these influencers five years ago, when it was really emerging, smaller...We're professional communicators, more than evangelists, in my opinion.
I agree with you. I think what they're trying to do is a different thing, which is, 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've real reputation.
I'm sure a lot of people have asked you to be the chief evangelist of their company for the last twenty years, and you've been smart enough, which is why you're still Guy, to say, "That sucks." And so that's easy for us.
I think what they're worried about, is going on at scale on these influencers, which is people just hawking any product in the world for a 5,000-dollar check. And I kept telling all these influencers five years ago, first of all, disclose it. Second of all, by the fifth thing that you promote that sucks, you're going to lose your audience.
Guy Kawasaki:
Do you think that Matthew McConaughey really drives a Lincoln-Mercury?
GaryVee:
Right? That's a good point. Actors and actresses, with what they do on commercials.
I saw Tom Selleck last night promoting something like retirement shit, and I was laughing. And I was really trying to understand, do I think Tom Selleck really believes in this shit? Or is he super pumped about the one-million-dollar bag that he's getting.
I don't know if Matthew McConaughey loves his thing. I like him. So I'm hoping he does do the same thing you and I would do.
I've only done two business development deals in the history of my life with brands. One was with Topps for $25,000, which luckily for me at this point in my career is an afterthought, because I got to have a baseball card. 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 successfully.
So I've never done an endorsement deal. But I've done these biz dev deals. I like learning from those.
Guy Kawasaki:
Well I'm waiting for the GaryVee hot and cold ice pack.
GaryVee:
I'm going to work on it.
Guy Kawasaki:
Okay. I will be your first customer, Gary.
GaryVee:
Put in your orders. Starting now.
Guy Kawasaki:
Any closing words?
GaryVee:
First of all, if you're a listener of Guy's podcast, I've had the privilege of really watching him for the last fifteen to twenty years. So, I'm very aware of the thoughtfulness and well-rounded nature of the listeners of this. So A, thank you for listening. B, I really think self-awareness is a big gain.
Both Guy and I are very busy, but we ran into each other very recently in Minnesota. We’ve reached out to each other at times. We've done co-book signings. I think our fondness in what I would call our acquaintance/friendship, we're just busy to ever get enough time to go hardcore.
But 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 fifteen years ago thought I wouldn't be, is, we may be very different in the way we communicate energy-wise, articulation, but...
Guy Kawasaki:
F-bombs.
GaryVee:
That's right.
But I think the self-awareness matters. I think if you're listening right now, really knowing yourself and feeling comfortable within your own skin, 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 in both of our communities, because I 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.
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.
Guy Kawasaki:
That's more like $2 million worth, but-
GaryVee:
Thank you for saying that.
Guy Kawasaki:
In a sense there's some irony there. In a sense you're saying, "Don't be a parrot." And we're quote "thought leaders" that people want to parrot. So we're telling you not to do that.
GaryVee:
That's where I think I've 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. They have a lot of misconceptions around me.
And I think when you look under the hood, deeper conversation around this specific issue, I think it's been something I've been able to bring value, including things that I think I was branded in around. Like hustle, and hard work, and burning out.
But it's never been my message. My message has been, going hard at your one at-bat-a-life, and being self-aware. Even at my earliest content I talked about working 9am-5pm and making $40,000 and being happy.
Guy Kawasaki:
I hope that listening to GaryVee has helped you understand how to succeed in business.
Also, I hope you developed an appreciation of the sophistication, depth, and long-term nature of Gary's game. He is one of the most interesting influencers in the world today. And, he got to buy some of Mark Zuckerberg's parents' Facebook stock. That's a pretty good claim to fame, too.
I'm Guy Kawasaki and this is Remarkable People.
Thanks to Jeff Sieh and Peg Fitzpatrick for helping me, in the words of GaryVee, to crush it.
One more thing. I've been recording bonus content in which I explain topics such as how to be a remarkable speaker, how to create remarkable emails, how to be a remarkable evangelist, and how to be a remarkable innovator. These episodes are bonus content for people who subscribe to my podcast. If you are a subscriber, they will appear automatically on your device.
Be healthy, be safe, wash your hands, maintain a six-foot distance from people, take care of yourselves, and I'll talk to you again soon.
This is Remarkable People.