WEBVTT 00:00:00.000 --> 00:00:01.980 So here's a question for you. Did you know that 00:00:01.980 --> 00:00:04.919 the guy who, you know, seems to be on every social 00:00:04.919 --> 00:00:07.120 media feed screaming at you to stop watching 00:00:07.120 --> 00:00:09.640 Netflix and start hustling? Oh, I know exactly 00:00:09.640 --> 00:00:11.699 who you're talking about. Right. That guy actually 00:00:11.699 --> 00:00:15.220 started his career like dusting bottles of Pinot 00:00:15.220 --> 00:00:18.699 Noir in a pretty standard New Jersey liquor store. 00:00:18.839 --> 00:00:21.359 It's a jarring image when you put it that way, 00:00:21.420 --> 00:00:23.699 isn't it? It's a very strange trajectory. I mean, 00:00:23.699 --> 00:00:26.440 you go from selling booze in the suburbs to becoming 00:00:26.440 --> 00:00:30.059 this this global avatar for the grind. For hustle 00:00:30.059 --> 00:00:32.479 culture. Yeah. And now he's advising Fortune 00:00:32.479 --> 00:00:36.630 500 CEOs and, you know, selling NFTs for. millions 00:00:36.630 --> 00:00:38.789 of dollars. It doesn't quite track. Well, that's 00:00:38.789 --> 00:00:40.590 the paradox of Gary Vaynerchuk, right? Because 00:00:40.590 --> 00:00:44.170 if you only know him from, say, a 30 second Instagram 00:00:44.170 --> 00:00:46.530 reel where he's dropping F -bombs and telling 00:00:46.530 --> 00:00:48.869 you to wake up at 5 a .m. Which is how most people 00:00:48.869 --> 00:00:50.990 know. It is. And you get this caricature. You 00:00:50.990 --> 00:00:53.509 see the hustle guy. But if you actually ignore 00:00:53.509 --> 00:00:55.869 the volume and I mean the literal volume of his 00:00:55.869 --> 00:00:58.530 voice and look at the P &L statements, you see 00:00:58.530 --> 00:01:02.689 a very, very different operator. And that is 00:01:02.689 --> 00:01:04.989 exactly why I wanted to do this deep dive today. 00:01:05.599 --> 00:01:07.439 Because I'll be honest, sometimes I see his clips 00:01:07.439 --> 00:01:09.900 and I just feel tired. Right. I feel a little 00:01:09.900 --> 00:01:11.840 bit scolded. But then I look at the businesses, 00:01:12.099 --> 00:01:15.620 VaynerMedia, Resi, Empathy Wines, and I realize 00:01:15.620 --> 00:01:18.400 there's this massive engine under the hood. A 00:01:18.400 --> 00:01:21.459 huge one. So I want to know how that engine was 00:01:21.459 --> 00:01:23.829 built. I don't really want the motivational quotes 00:01:23.829 --> 00:01:26.290 today. I want the mechanics. How did he actually 00:01:26.290 --> 00:01:28.790 make the money before he started telling everyone 00:01:28.790 --> 00:01:30.969 else how to make theirs? That is absolutely the 00:01:30.969 --> 00:01:33.069 right question to ask because the whole motivational 00:01:33.069 --> 00:01:35.549 speaking thing, that didn't come first. That 00:01:35.549 --> 00:01:38.090 was, in a lot of ways, the victory lap. The byproduct. 00:01:38.250 --> 00:01:40.689 The byproduct, exactly. To really understand 00:01:40.689 --> 00:01:42.709 the Vaynerchuk machine, we have to strip away 00:01:42.709 --> 00:01:45.750 the Gary V persona and look at Gary Vaynerchuk, 00:01:45.810 --> 00:01:47.450 the merchant, the guy who sells stuff. Okay. 00:01:47.469 --> 00:01:50.769 So today we're going to track his path all the 00:01:50.769 --> 00:01:53.969 way from a Soviet. immigrant upbringing to building 00:01:53.969 --> 00:01:57.469 a $60 million wine empire and then pivoting to 00:01:57.469 --> 00:02:00.230 a media holding company that actually rivals 00:02:00.230 --> 00:02:03.469 the legacy agencies on Madison Avenue. And we 00:02:03.469 --> 00:02:05.310 have a ton of source material to get through. 00:02:05.370 --> 00:02:07.849 We've got the biographies, the financial reports 00:02:07.849 --> 00:02:10.729 from his big company exits, the timelines of 00:02:10.729 --> 00:02:13.129 all his media properties. It's a lot. It is. 00:02:13.250 --> 00:02:16.090 But before we get into the chronological story, 00:02:16.349 --> 00:02:19.449 what's the through line? Is there like a grand 00:02:19.449 --> 00:02:21.990 unified theory of Gary Vaynerchuk? What's the 00:02:21.990 --> 00:02:24.710 one idea that connects it all? There is. And 00:02:24.710 --> 00:02:27.229 it's surprisingly simple. If you look closely 00:02:27.229 --> 00:02:29.569 at every single venture, and I mean everything, 00:02:29.770 --> 00:02:32.330 from the liquor store to the ad agency to the 00:02:32.330 --> 00:02:35.490 NFTs, it all comes down to one single concept. 00:02:35.830 --> 00:02:38.330 Attention arbitrage. Okay, stop there. Attention 00:02:38.330 --> 00:02:41.949 arbitrage. That sounds like some marketing jargon 00:02:41.949 --> 00:02:44.009 that an agency invents so they can charge their 00:02:44.009 --> 00:02:46.189 clients double. What does that actually mean 00:02:46.189 --> 00:02:48.689 in the real world? It sounds fancy, I know. But 00:02:48.689 --> 00:02:51.080 it's actually dirt simple. It just means spotting 00:02:51.080 --> 00:02:52.979 where people are spending their time, their attention, 00:02:53.120 --> 00:02:55.620 before the rest of the market realizes it. And 00:02:55.620 --> 00:02:58.319 therefore, before the price of advertising on 00:02:58.319 --> 00:03:00.900 that platform goes through the roof, it's buying 00:03:00.900 --> 00:03:03.159 attention for pennies on the dollar. Can you 00:03:03.159 --> 00:03:06.319 give me an example? Sure. In 1996, that underpriced 00:03:06.319 --> 00:03:09.879 attention was email. In 2000, it was Google AdWords. 00:03:10.020 --> 00:03:13.960 In 2006, it was YouTube. More recently, in 2020, 00:03:14.240 --> 00:03:16.979 it was TikTok. He doesn't build the platforms 00:03:16.979 --> 00:03:19.620 himself. He just exploits the fact that big companies 00:03:19.620 --> 00:03:21.699 are always too slow to move their money to where 00:03:21.699 --> 00:03:23.919 the eyeballs actually are. So he's basically 00:03:23.919 --> 00:03:25.620 a day trader, but instead of trading stocks, 00:03:25.900 --> 00:03:29.139 he's trading. Eyeballs. That is literally the 00:03:29.139 --> 00:03:31.479 title of his 2024 book, Day Trading Attention. 00:03:31.800 --> 00:03:33.580 But yes, that is the mechanic. That's the whole 00:03:33.580 --> 00:03:36.060 game. And to see how he first learned that, we 00:03:36.060 --> 00:03:38.680 have to go way, way back. Before the internet, 00:03:38.800 --> 00:03:41.840 we have to go to Bobruisk. Which is in modern 00:03:41.840 --> 00:03:44.680 -day Belarus. Correct. Born Gennady Alexandrovich 00:03:44.680 --> 00:03:47.400 Vaynerchuk in 1975, Soviet Union. And this is 00:03:47.400 --> 00:03:49.300 really not a silver spoon story. Not at all. 00:03:49.379 --> 00:03:51.539 The family came to the U .S. in 1978 through 00:03:51.539 --> 00:03:53.840 a refugee resettlement program. He was only three 00:03:53.840 --> 00:03:56.199 years old. They arrived with basically nothing. 00:03:56.810 --> 00:04:00.469 And I think we hear immigrant story so often 00:04:00.469 --> 00:04:03.650 that we kind of glaze over. It becomes a bit 00:04:03.650 --> 00:04:06.270 of a cliche in these business biographies. But 00:04:06.270 --> 00:04:09.050 we need to contextualize this. We're talking 00:04:09.050 --> 00:04:12.469 about a studio apartment in Queens with, what, 00:04:12.569 --> 00:04:14.789 eight family members? Something like that. Right. 00:04:14.870 --> 00:04:17.009 It was incredibly crowded. And then they moved 00:04:17.009 --> 00:04:20.060 to Edison, New Jersey. And this part is key because 00:04:20.060 --> 00:04:22.980 he wasn't insulated. He wasn't inside playing 00:04:22.980 --> 00:04:26.360 video games. He was on the streets selling things. 00:04:26.639 --> 00:04:29.180 The classic kid businesses. The classic cliches. 00:04:29.180 --> 00:04:32.139 Yeah. Baseball cards, lemonade stands. But he 00:04:32.139 --> 00:04:34.779 took them to an absolute extreme. There's a story 00:04:34.779 --> 00:04:36.459 that's often told about him running multiple 00:04:36.459 --> 00:04:39.540 lemonade stands at the same time across the neighborhood 00:04:39.540 --> 00:04:42.839 and managing his friends as employees. So he 00:04:42.839 --> 00:04:44.879 was franchising. He was franchising lemonade 00:04:44.879 --> 00:04:47.439 at seven years old. He was learning about profit 00:04:47.439 --> 00:04:49.319 margins and stuff. scaling before he was even 00:04:49.319 --> 00:04:51.879 10. But the real business education, the one 00:04:51.879 --> 00:04:53.459 that really sets the foundation, that starts 00:04:53.459 --> 00:04:55.740 when he's 14. That's when he gets dragged into 00:04:55.740 --> 00:04:57.720 the family business. Shoppers discount liquors. 00:04:57.839 --> 00:05:01.740 Not exactly a branding masterpiece, is it? No, 00:05:01.860 --> 00:05:04.360 it sounds like the place you go to buy the giant 00:05:04.360 --> 00:05:07.259 plastic jugs of vodka. Exactly. And it was a 00:05:07.259 --> 00:05:10.560 volume business. His dad, Sasha, ran a very tight 00:05:10.560 --> 00:05:13.209 ship. Gary started out, and this is true, by 00:05:13.209 --> 00:05:16.389 bagging ice in the basement for $2 an hour in 00:05:16.389 --> 00:05:19.250 tips. Bagging ice. Bagging ice. It's pure manual 00:05:19.250 --> 00:05:22.170 labor. But eventually, you know, he gets permeated. 00:05:22.170 --> 00:05:24.829 He moves up to the sales floor. And this is where 00:05:24.829 --> 00:05:27.129 that attention arbitrage instinct first kicks 00:05:27.129 --> 00:05:28.769 in, even though he didn't have a name for it 00:05:28.769 --> 00:05:32.089 yet. How so? Well, he started watching the customers. 00:05:32.839 --> 00:05:34.879 And he realized that people weren't just buying 00:05:34.879 --> 00:05:36.879 liquid in a bottle. They were buying a story. 00:05:37.160 --> 00:05:40.240 They were buying prestige or recommendation or 00:05:40.240 --> 00:05:43.120 feeling. So he started studying? He started devouring 00:05:43.120 --> 00:05:46.560 information. He read every issue of Wine Spectator 00:05:46.560 --> 00:05:49.519 magazine. He wasn't just reading it. He was memorizing 00:05:49.519 --> 00:05:52.259 the ratings, the reviews, the scores. Learning 00:05:52.259 --> 00:05:55.120 the data. Exactly, the data. So when a customer 00:05:55.120 --> 00:05:58.240 would walk in looking for some... you know, specific 00:05:58.240 --> 00:06:01.660 $100 bottle of Cabernet, he could walk up and 00:06:01.660 --> 00:06:03.879 say, hey, I know you like that profile, but this 00:06:03.879 --> 00:06:06.160 bottle over here got a 92 from Robert Parker 00:06:06.160 --> 00:06:09.300 and it's half the price. Ah, so he's building 00:06:09.300 --> 00:06:11.680 trust. He's not just upselling. He's building 00:06:11.680 --> 00:06:15.620 immense trust. He's providing value first. But 00:06:15.620 --> 00:06:17.779 the real explosion, the thing that changes everything, 00:06:17.920 --> 00:06:21.120 that happens in 1998. He graduates from College 00:06:21.120 --> 00:06:23.199 Mount Ida College with a management science degree, 00:06:23.360 --> 00:06:25.639 and he takes over the day -to -day operations 00:06:25.639 --> 00:06:29.170 of the store. And 1998. I mean, we have to put 00:06:29.170 --> 00:06:31.129 ourselves in that time. The Internet is basically 00:06:31.129 --> 00:06:34.290 a baby. Most people are still absolutely terrified 00:06:34.290 --> 00:06:36.730 to put their credit card information into a computer. 00:06:36.889 --> 00:06:39.550 And that right there is the arbitrage. That fear, 00:06:39.709 --> 00:06:41.790 that slowness from everyone else, that's the 00:06:41.790 --> 00:06:43.850 opportunity. He looked at that behavior and said, 00:06:43.949 --> 00:06:46.110 people are going to buy wine this way. I'm sure 00:06:46.110 --> 00:06:49.209 of it. So he made two big moves. Two huge moves. 00:06:49.529 --> 00:06:52.329 First, he rebranded the store. He changed it 00:06:52.329 --> 00:06:54.790 from Shoppers Discount Liquors to Wine Library. 00:06:55.089 --> 00:06:56.649 Which immediately sounds more authoritative, 00:06:56.670 --> 00:06:59.370 more premium. Instantly. And then he launched 00:06:59.370 --> 00:07:01.750 WineLibrary .com. He took the local liquor store 00:07:01.750 --> 00:07:03.829 online. Okay, let's unpack this growth here. 00:07:03.910 --> 00:07:06.230 Because the numbers, they're frankly absurd. 00:07:06.720 --> 00:07:08.899 The source notes all say he grew the business 00:07:08.899 --> 00:07:12.240 from $3 million a year to $60 million a year. 00:07:12.500 --> 00:07:16.279 60. A 20x return. Right. And you don't get that 00:07:16.279 --> 00:07:18.740 just by, you know, putting up a website. Plenty 00:07:18.740 --> 00:07:21.019 of people had websites in 1998 and went completely 00:07:21.019 --> 00:07:23.680 bust. What was he doing differently? Okay, this 00:07:23.680 --> 00:07:25.720 is where we get into the real weeds of the tactics. 00:07:25.959 --> 00:07:27.860 And the first one, the one that built the foundation. 00:07:28.560 --> 00:07:32.060 was email email yeah simple email back in 1998 00:07:32.060 --> 00:07:34.560 spam filters weren't really a big thing if you 00:07:34.560 --> 00:07:36.579 sent someone an email they almost always opened 00:07:36.579 --> 00:07:38.819 it your open rates were like 80 or 90 percent 00:07:38.819 --> 00:07:41.939 it was incredible unthinkable today completely 00:07:41.939 --> 00:07:44.439 so he collected email addresses at the checkout 00:07:44.439 --> 00:07:47.670 counter aggressively. And he started sending 00:07:47.670 --> 00:07:49.689 out daily emails with offers that were actually 00:07:49.689 --> 00:07:52.389 valuable, not just buy this, buy this. He'd write 00:07:52.389 --> 00:07:54.910 tasting notes, tell stories. He treated that 00:07:54.910 --> 00:07:57.730 email list like gold. So he had a direct line 00:07:57.730 --> 00:07:59.829 to his customer that cost him basically zero 00:07:59.829 --> 00:08:02.649 dollars to use. That's it. A free broadcast mechanism. 00:08:03.149 --> 00:08:05.730 But the bigger play, the one that really scaled 00:08:05.730 --> 00:08:08.449 the business nationally, was Google AdWords. 00:08:08.649 --> 00:08:11.769 Ah, the early days of search ads. The very early 00:08:11.769 --> 00:08:14.810 days. When Google first launched their ad platform, 00:08:15.129 --> 00:08:17.689 basically nobody was bidding on keywords for 00:08:17.689 --> 00:08:20.569 wine. The big established wine retailers were 00:08:20.569 --> 00:08:23.129 still spending millions of dollars on full -page 00:08:23.129 --> 00:08:25.329 ads in the New York Times and on billboards. 00:08:25.629 --> 00:08:28.389 And Gary realized he could buy search terms. 00:08:28.569 --> 00:08:31.910 He realized he could buy the term wine, or Cabernet 00:08:31.910 --> 00:08:35.769 Sauvignon, for pennies a click. Pennies? Literal 00:08:35.769 --> 00:08:40.460 pennies. For a nickel, maybe a dime. he could 00:08:40.460 --> 00:08:43.840 get a highly qualified buyer, someone who was 00:08:43.840 --> 00:08:46.580 actively at that very moment searching for wine 00:08:46.580 --> 00:08:49.480 to land directly on his website. That's an incredible 00:08:49.480 --> 00:08:52.419 arbitrage. He spent every single dollar he had 00:08:52.419 --> 00:08:55.179 on it. He milked that margin for years until 00:08:55.179 --> 00:08:57.360 the big guys, the big retailers finally caught 00:08:57.360 --> 00:08:59.600 on and started bidding the price up. But by the 00:08:59.600 --> 00:09:01.480 time they finally showed up to the party, he 00:09:01.480 --> 00:09:04.240 had already built a loyal customer base of tens 00:09:04.240 --> 00:09:06.299 of thousands of people from all over the country. 00:09:06.539 --> 00:09:08.820 It's fascinating. It wasn't that he was necessarily 00:09:08.820 --> 00:09:11.139 a better sommelier, though he was good. It was 00:09:11.139 --> 00:09:12.820 that he was a better media buyer. That's it. 00:09:13.019 --> 00:09:14.940 He just understood the plumbing of the Internet 00:09:14.940 --> 00:09:18.429 better and earlier than his competitors. Precisely. 00:09:18.429 --> 00:09:22.029 He was using the wine to fund his real education, 00:09:22.350 --> 00:09:24.730 which was learning how the Internet worked. And 00:09:24.730 --> 00:09:26.730 that, of course, naturally leads us to 2006. 00:09:27.269 --> 00:09:30.210 YouTube. YouTube launches. It's new. It's weird. 00:09:30.330 --> 00:09:32.470 Nobody knows what to make of it. And we get Wine 00:09:32.470 --> 00:09:35.259 Library TV. Or as he always called it, the Thunder 00:09:35.259 --> 00:09:37.580 Show. The Thunder Show, that's right. He starts 00:09:37.580 --> 00:09:39.720 filming these episodes in the back of the store. 00:09:39.899 --> 00:09:42.279 He's wearing a New York Jets jersey. He's got 00:09:42.279 --> 00:09:45.019 a big plastic spit bucket. And he's just screaming 00:09:45.019 --> 00:09:47.740 about tannins and tasting notes. It was completely, 00:09:47.860 --> 00:09:50.460 totally unpolished. And that was the whole point, 00:09:50.519 --> 00:09:53.399 right? Because wine culture before this was... 00:09:53.740 --> 00:09:56.200 you know, ascots and classical music in the background. 00:09:56.419 --> 00:09:59.500 It was designed to be exclusionary. It was incredibly 00:09:59.500 --> 00:10:02.600 stuffy. He completely democratized it. He made 00:10:02.600 --> 00:10:05.019 it okay to not know everything as long as you're 00:10:05.019 --> 00:10:07.480 willing to taste and learn. He'd taste a wine 00:10:07.480 --> 00:10:10.080 and say it tasted like grass clippings or a dirt 00:10:10.080 --> 00:10:12.500 clod. Things people can actually relate to. Yes. 00:10:12.960 --> 00:10:15.600 But look at the work ethic here. This is what's 00:10:15.600 --> 00:10:18.379 really key. He didn't do, you know, a season 00:10:18.379 --> 00:10:20.779 of 10 episodes and take a break. He did a thousand 00:10:20.779 --> 00:10:25.029 episodes. Thousand. One thousand. Daily. For 00:10:25.029 --> 00:10:28.309 five straight years. Before he finally retired 00:10:28.309 --> 00:10:30.750 the show in 2011 to start a new one called The 00:10:30.750 --> 00:10:33.909 Daily Grape. That level of consistency is just 00:10:33.909 --> 00:10:36.809 it's staggering. It is. And that's what he means 00:10:36.809 --> 00:10:38.789 when he talks about hustle. It wasn't just about 00:10:38.789 --> 00:10:41.549 working late. It was the relentless consistency 00:10:41.549 --> 00:10:44.210 of the output. He was building a relationship 00:10:44.210 --> 00:10:47.330 with his audience every single day. And he was 00:10:47.330 --> 00:10:49.389 in the comments. He was in every comment section 00:10:49.389 --> 00:10:51.529 replying to everyone. This is really the community 00:10:51.529 --> 00:10:55.059 manager phase of his career. He realized. way 00:10:55.059 --> 00:10:57.840 before anyone else, that the brand wasn't your 00:10:57.840 --> 00:11:01.320 logo or your slogan. The brand was the conversation 00:11:01.320 --> 00:11:03.259 that was happening in the comments section. OK, 00:11:03.360 --> 00:11:05.320 so he builds this absolute beast. He's the king 00:11:05.320 --> 00:11:07.440 of wine on the Internet. The business is doing 00:11:07.440 --> 00:11:10.659 $60 million a year. The family is set for life. 00:11:11.100 --> 00:11:14.659 Most people, I mean, 99 .9 % of people would 00:11:14.659 --> 00:11:16.440 just ride that wave until retirement. Right. 00:11:16.580 --> 00:11:19.259 They'd buy a boat, maybe open a second location 00:11:19.259 --> 00:11:21.600 in a different town and just, you know, chill 00:11:21.600 --> 00:11:24.009 out. But Gary isn't driven by the wine. I think 00:11:24.009 --> 00:11:26.230 that's what becomes clear. He's driven by the 00:11:26.230 --> 00:11:29.330 game. He saw that selling wine was just one application 00:11:29.330 --> 00:11:32.710 of his actual skill set. His real skill was generating 00:11:32.710 --> 00:11:37.190 and monetizing attention. So in August of 2011 00:11:37.190 --> 00:11:39.250 he does something incredible. He walks away. 00:11:39.389 --> 00:11:42.159 That is a genuinely terrifying move. to walk 00:11:42.159 --> 00:11:44.440 away from the cash cow that you personally built 00:11:44.440 --> 00:11:46.240 from the ground up. He stepped away from the 00:11:46.240 --> 00:11:48.879 day -to -day of the wine business to start VaynerMedia 00:11:48.879 --> 00:11:51.860 with his brother, AJ. And he did it because he 00:11:51.860 --> 00:11:54.500 saw the next great arbitrage opportunity. Which 00:11:54.500 --> 00:11:57.200 was? Social media for corporations. Okay, let's 00:11:57.200 --> 00:11:59.820 look at VaynerMedia. Because back in, what, 2009, 00:12:00.059 --> 00:12:04.019 2011, the idea of a social media agency usually 00:12:04.019 --> 00:12:05.779 just meant a couple of the 20 -year -old interns 00:12:05.779 --> 00:12:08.059 posting on a company's Facebook page. It wasn't 00:12:08.059 --> 00:12:09.879 a serious industry. How did he turn that into 00:12:09.879 --> 00:12:12.600 a powerhouse? Well, he essentially applied the 00:12:12.600 --> 00:12:15.519 Wine Library TV model to Fortune 500 brands. 00:12:15.779 --> 00:12:18.700 He looked at the traditional agencies, the Ogilvys, 00:12:18.960 --> 00:12:21.159 the McCanns, and saw that they were all built 00:12:21.159 --> 00:12:23.159 on the TV commercial model. A Mad Men model. 00:12:23.259 --> 00:12:25.440 The Mad Men model, exactly. They would spend 00:12:25.440 --> 00:12:29.419 six months and $2 million. to create one single 00:12:29.419 --> 00:12:33.200 perfect 30 -second video. And Gary looked at 00:12:33.200 --> 00:12:35.340 that and just said, that's completely stupid. 00:12:35.500 --> 00:12:37.460 Stupid. I mean, that's how the entire industry 00:12:37.460 --> 00:12:39.340 had worked for 50 years. It's a proven model. 00:12:39.559 --> 00:12:41.940 It was proven for a different medium. He argued 00:12:41.940 --> 00:12:44.320 that on a scrolling Facebook feed, nobody cares 00:12:44.320 --> 00:12:46.399 about your cinematic production value if the 00:12:46.399 --> 00:12:48.399 content isn't relevant right now. He pushed for 00:12:48.399 --> 00:12:51.539 volume and speed over perfection. So instead 00:12:51.539 --> 00:12:56.149 of one $2 million video. Let's make $1 ,000 videos 00:12:56.149 --> 00:12:59.830 or $210 ,000 videos. Let's test them all. Let's 00:12:59.830 --> 00:13:01.330 see what people actually click on, what they 00:13:01.330 --> 00:13:03.529 share, and then let's put the real money behind 00:13:03.529 --> 00:13:05.590 the winner. It's the Google AdWords strategy 00:13:05.590 --> 00:13:08.190 all over again. Test cheap, find the winner, 00:13:08.350 --> 00:13:10.870 and then scale it. That's all it is. It was a 00:13:10.870 --> 00:13:13.570 newsroom approach to advertising. If something 00:13:13.570 --> 00:13:16.190 happened in pop culture that morning, say an 00:13:16.190 --> 00:13:18.570 awards show or a big sports game, VaynerMedia 00:13:18.570 --> 00:13:20.629 wanted their clients tweeting and posting about 00:13:20.629 --> 00:13:23.419 it by noon. And the big agencies just couldn't 00:13:23.419 --> 00:13:25.899 move that fast. They were buried in legal approvals 00:13:25.899 --> 00:13:28.779 and endless meetings. VaynerMedia was built for 00:13:28.779 --> 00:13:31.159 speed, for the pace of the Internet, not the 00:13:31.159 --> 00:13:34.179 pace of television. And the growth was, again, 00:13:34.299 --> 00:13:37.360 just massive. By 2016, what are the numbers? 00:13:37.440 --> 00:13:39.820 They're grossing $100 million in revenue. $100 00:13:39.820 --> 00:13:43.799 million. And they have 600 employees. Ad Age, 00:13:44.059 --> 00:13:46.519 which is the industry bible, puts them on their 00:13:46.519 --> 00:13:50.120 coveted A -list of top agencies. He had proven 00:13:50.120 --> 00:13:53.320 that tweets and posts were actually a nine -figure 00:13:53.320 --> 00:13:55.620 industry. Here's where it gets really interesting 00:13:55.620 --> 00:13:58.379 for me, though. Beyond just the agency's success. 00:13:58.909 --> 00:14:00.870 It's the structure he built around it. You're 00:14:00.870 --> 00:14:03.490 talking about VaynerX. Exactly. VaynerMedia is 00:14:03.490 --> 00:14:05.830 just the agency. It sits under this bigger holding 00:14:05.830 --> 00:14:08.250 company called VaynerX. And this is where you 00:14:08.250 --> 00:14:11.230 see his ambition to be more than just a guy who 00:14:11.230 --> 00:14:13.070 provides a service. Right. Because at the end 00:14:13.070 --> 00:14:15.110 of the day, an agency is a service business. 00:14:15.309 --> 00:14:17.629 You have clients and clients can fire you. It's 00:14:17.629 --> 00:14:19.950 a constant grind for a new business. So he started 00:14:19.950 --> 00:14:22.299 building his own media properties. He didn't 00:14:22.299 --> 00:14:24.320 want to just buy ads on other people's platforms. 00:14:24.480 --> 00:14:26.460 He wanted to own the platforms. That's where 00:14:26.460 --> 00:14:29.080 the gallery comes in, which later became Gallery 00:14:29.080 --> 00:14:31.340 Media Group. And this is the part of the company 00:14:31.340 --> 00:14:33.659 that houses publishers like PureWow. Which is 00:14:33.659 --> 00:14:38.200 a huge women's lifestyle site. Huge. And 1E37PM, 00:14:38.340 --> 00:14:40.659 which is more of a men's lifestyle and culture 00:14:40.659 --> 00:14:44.299 brand focused on, you know, crypto sports cards, 00:14:44.399 --> 00:14:47.029 that sort of thing. So why do that? why own the 00:14:47.029 --> 00:14:49.509 magazine and the ad agency it seems like two 00:14:49.509 --> 00:14:52.690 different businesses it's all about control And 00:14:52.690 --> 00:14:55.009 data. If you own the media company like PureWow, 00:14:55.210 --> 00:14:58.350 you own the audience data. You know exactly what 00:14:58.350 --> 00:15:01.850 articles women age 25 to 45 are reading, what 00:15:01.850 --> 00:15:04.090 products they are clicking on, what content they 00:15:04.090 --> 00:15:06.070 are sharing with their friends. So you can then 00:15:06.070 --> 00:15:08.269 take that real time data, walk it over to the 00:15:08.269 --> 00:15:10.289 VaynerMedia side of the office and tell your 00:15:10.289 --> 00:15:13.490 client, Pepsi or Toyota or whoever, hey, we know 00:15:13.490 --> 00:15:15.490 with certainty what content works right now because 00:15:15.490 --> 00:15:18.250 we see it performing on our own platform. It 00:15:18.250 --> 00:15:20.509 creates this incredible feedback loop that other 00:15:20.509 --> 00:15:22.940 agencies just didn't have. That is actually brilliant. 00:15:23.080 --> 00:15:25.120 It's a vertical integration for the attention 00:15:25.120 --> 00:15:27.379 economy. That's a perfect way to put it. And 00:15:27.379 --> 00:15:29.940 having that machine, that confidence, it gave 00:15:29.940 --> 00:15:32.320 him the platform to start spinning out other 00:15:32.320 --> 00:15:35.039 businesses. This is where we get into the full 00:15:35.039 --> 00:15:37.860 -blown serial entrepreneur phase of his career. 00:15:38.100 --> 00:15:40.740 And let's start with Rezzy because I, like a 00:15:40.740 --> 00:15:43.179 lot of people, use Rezzy to book dinner reservations 00:15:43.179 --> 00:15:45.919 all the time. I remember when it launched, it 00:15:45.919 --> 00:15:48.840 felt like this cool niche app for foodies in 00:15:48.840 --> 00:15:51.919 New York and L .A. I had absolutely no idea. 00:15:52.440 --> 00:15:54.799 Gary Vaynerchuk was a co -founder. It doesn't 00:15:54.799 --> 00:15:57.080 seem like his world. He co -founded it with Ben 00:15:57.080 --> 00:15:59.779 Leventhal, who was a founder of Eater. And again, 00:15:59.840 --> 00:16:02.659 you have to ask the question, why? Why does a 00:16:02.659 --> 00:16:04.840 social media guy care about the restaurant reservation 00:16:04.840 --> 00:16:07.740 business? I'm going to guess it's about data. 00:16:07.860 --> 00:16:10.860 It's always about data. And friction. He saw 00:16:10.860 --> 00:16:13.139 that the simple act of booking a table at a good 00:16:13.139 --> 00:16:15.519 restaurant was a major friction point for consumers. 00:16:15.820 --> 00:16:17.720 You had to call, they'd put you on hold, they'd 00:16:17.720 --> 00:16:20.480 say we're booked. OpenTable was the big giant 00:16:20.480 --> 00:16:22.860 in the space, but their software felt clunky 00:16:22.860 --> 00:16:25.080 and old. It was built for desktops, not phones. 00:16:25.320 --> 00:16:28.279 Right. Resi was mobile first, it was slick, and 00:16:28.279 --> 00:16:31.340 it specifically catered to the cool, high -demand 00:16:31.340 --> 00:16:33.299 restaurants that didn't want to be on OpenTable. 00:16:33.500 --> 00:16:35.519 So it was another arbitrage. It was an arbitrage 00:16:35.519 --> 00:16:37.740 on the dining experience itself. And it paid 00:16:37.740 --> 00:16:41.049 off. Big time. American Express acquired Rezzy 00:16:41.049 --> 00:16:44.750 in 2019. The exact terms weren't disclosed, but 00:16:44.750 --> 00:16:46.950 the deal was significant enough to really validate 00:16:46.950 --> 00:16:49.490 him in the tech world. He wasn't just a marketer 00:16:49.490 --> 00:16:52.669 anymore. He was a legitimate tech founder with 00:16:52.669 --> 00:16:55.870 a major successful exit to a blue chip company. 00:16:56.090 --> 00:16:59.289 And then almost immediately after that, he goes 00:16:59.289 --> 00:17:01.190 full circle. He goes back to the bottle. Back 00:17:01.190 --> 00:17:03.690 to wine. Yeah. With empathy wines. But this time 00:17:03.690 --> 00:17:06.289 it was a totally different model. Totally different. 00:17:06.450 --> 00:17:08.650 He looked at the wine industry and saw that the 00:17:08.650 --> 00:17:11.390 core problem was still distribution. In the United 00:17:11.390 --> 00:17:14.210 States, wine distribution is a complete nightmare. 00:17:14.670 --> 00:17:17.509 It's a mandatory three -tier system that was 00:17:17.509 --> 00:17:19.869 set up after Prohibition. Right. It goes from 00:17:19.869 --> 00:17:22.450 the winery to a distributor to a retailer, and 00:17:22.450 --> 00:17:25.009 then finally to you, the customer. And every 00:17:25.009 --> 00:17:27.410 single one of them takes a big cut, a big margin. 00:17:27.670 --> 00:17:30.829 Which is why a decent bottle of wine costs $20, 00:17:30.849 --> 00:17:33.529 but often tastes like it should have cost $5. 00:17:33.529 --> 00:17:36.710 That is exactly why. Empathy Wines was designed 00:17:36.710 --> 00:17:39.789 to break that model. It was direct to consumer, 00:17:39.990 --> 00:17:43.750 DTC. He sourced high quality grapes from top 00:17:43.750 --> 00:17:46.930 farmers in California who often had excess supply 00:17:46.930 --> 00:17:49.869 arbitrage again, and he sold the finished wine 00:17:49.869 --> 00:17:52.500 directly to his followers online. Cutting out 00:17:52.500 --> 00:17:54.099 the distributor and the retailer. Completely. 00:17:54.119 --> 00:17:57.339 So he could sell what was essentially a $50 quality 00:17:57.339 --> 00:18:00.880 wine for $20 and still make a better profit margin 00:18:00.880 --> 00:18:03.059 than the traditional wineries. And the brilliant 00:18:03.059 --> 00:18:05.980 part is because he already had this massive audience 00:18:05.980 --> 00:18:08.400 from his social media presence, he didn't have 00:18:08.400 --> 00:18:10.720 to pay for advertising. He just posted a video 00:18:10.720 --> 00:18:12.960 saying, hey, guys, I made a new wine. And his 00:18:12.960 --> 00:18:14.839 followers bought it. His customer acquisition 00:18:14.839 --> 00:18:17.720 cost was basically zero. That is the absolute 00:18:17.720 --> 00:18:20.619 holy grail for any DTC business. And, of course, 00:18:20.680 --> 00:18:22.759 the big guys noticed. Constellation Brands, one 00:18:22.759 --> 00:18:24.440 of the largest alcohol companies in the entire 00:18:24.440 --> 00:18:27.059 world, they saw this incredibly efficient model 00:18:27.059 --> 00:18:28.880 and they just bought the whole company in 2020. 00:18:29.299 --> 00:18:32.799 Okay, so just to recap, he's conquered wine twice. 00:18:33.240 --> 00:18:36.160 He's conquered the ad world. He's conquered restaurant 00:18:36.160 --> 00:18:39.400 tech. So now we have to talk about the elephant 00:18:39.400 --> 00:18:44.400 in the room, the JPEGs. Web 3. I'm going to play 00:18:44.400 --> 00:18:46.299 the skeptic here for our listeners, because when 00:18:46.299 --> 00:18:49.140 the whole NFT craze hit, it really felt like 00:18:49.140 --> 00:18:52.220 a lot of smoke and mirrors, a lot of hype. And 00:18:52.220 --> 00:18:54.740 then suddenly there's Gary drawing these little 00:18:54.740 --> 00:18:57.420 stick figures, calling them V friends and selling 00:18:57.420 --> 00:19:00.019 them for thousands, sometimes tens of thousands 00:19:00.019 --> 00:19:03.559 of dollars. So was this just a cash grab? Because 00:19:03.559 --> 00:19:06.039 from the outside, it looked like he was monetizing 00:19:06.039 --> 00:19:09.339 his fan base's loyalty in a very, very aggressive 00:19:09.339 --> 00:19:11.930 way. And that is a very fair criticism. A lot 00:19:11.930 --> 00:19:13.869 of people made that exact point at the time. 00:19:14.130 --> 00:19:16.130 But if you look at the actual structure of the 00:19:16.130 --> 00:19:17.869 VFriends project, he was trying to do something 00:19:17.869 --> 00:19:19.549 fundamentally different than just selling digital 00:19:19.549 --> 00:19:22.990 art. He attached utility to every single token. 00:19:23.150 --> 00:19:25.529 OK, explain utility in this context, because 00:19:25.529 --> 00:19:27.789 that word was thrown around a lot. So if you 00:19:27.789 --> 00:19:30.369 bought a VFriend NFT, it wasn't just a digital 00:19:30.369 --> 00:19:32.609 picture of, say, an empathetic elephant. It was 00:19:32.609 --> 00:19:34.990 a smart contract that also acted as a ticket. 00:19:35.309 --> 00:19:37.630 A ticket to what? Holding that specific token 00:19:37.630 --> 00:19:39.990 gave you a three -year admission pass to his 00:19:39.990 --> 00:19:43.490 big super conference, VCon. So the art was a 00:19:43.490 --> 00:19:45.930 collectible, but the token itself unlocked a 00:19:45.930 --> 00:19:48.710 real -world experience. So it's basically a conference 00:19:48.710 --> 00:19:50.990 ticket that you can hold as an asset and then 00:19:50.990 --> 00:19:53.910 resell on an open market. Precisely. And because 00:19:53.910 --> 00:19:55.829 it's all in the blockchain, if you sell your 00:19:55.829 --> 00:19:59.329 NFT to someone else for a profit, the original 00:19:59.329 --> 00:20:02.269 creator, in this case Gary, automatically gets 00:20:02.269 --> 00:20:04.329 a small royalty percentage of that secondary 00:20:04.329 --> 00:20:11.859 sale. Okay, so the argument is... Don't just 00:20:11.859 --> 00:20:14.099 look at the cute drawing. Look at the mechanics 00:20:14.099 --> 00:20:16.259 of the smart contract underneath it. Right. His 00:20:16.259 --> 00:20:18.960 big bet was that smart contracts are the next 00:20:18.960 --> 00:20:21.559 email, the next AdWords, the next big platform 00:20:21.559 --> 00:20:24.019 shift. And he wanted to be first. He wanted to 00:20:24.019 --> 00:20:26.599 learn by doing. And the market, at least for 00:20:26.599 --> 00:20:29.579 a time, responded in a huge way. He did a collaboration 00:20:29.579 --> 00:20:32.079 with another project called Doodles that ended 00:20:32.079 --> 00:20:34.559 up selling at a Christie's auction. A real world 00:20:34.559 --> 00:20:37.700 established auction house. Yes. we're talking 00:20:37.700 --> 00:20:40.279 about serious institutional money coming in and 00:20:40.279 --> 00:20:43.960 validating this new space but let's be honest 00:20:43.960 --> 00:20:46.759 the market crashed hard a lot of people who bought 00:20:46.759 --> 00:20:49.200 nfts maybe even v friends lost a lot of money 00:20:49.200 --> 00:20:51.859 they absolutely did and that is the inherent 00:20:51.859 --> 00:20:55.240 risk of following a futurist if you buy into 00:20:55.240 --> 00:20:58.140 the arbitrage too early Or more likely, you buy 00:20:58.140 --> 00:21:00.960 in at the absolute peak of the hype cycle, you 00:21:00.960 --> 00:21:04.220 can get badly burned. Now, to his credit, Gary 00:21:04.220 --> 00:21:06.519 has always been very vocal about this. He's on 00:21:06.519 --> 00:21:08.859 record saying 99 % of all NFT projects are going 00:21:08.859 --> 00:21:11.039 to go to zero. But that doesn't really comfort 00:21:11.039 --> 00:21:12.940 the person who bought a token at the top of the 00:21:12.940 --> 00:21:15.819 market and saw its value collapse. No. And this 00:21:15.819 --> 00:21:18.240 is where that guru status he has gets really 00:21:18.240 --> 00:21:20.430 tricky. Because when people start to follow your 00:21:20.430 --> 00:21:22.650 financial moves, they share in your wins, but 00:21:22.650 --> 00:21:24.710 they also have to share in your losses. That 00:21:24.710 --> 00:21:26.950 transitions us perfectly then to the content 00:21:26.950 --> 00:21:29.529 machine. Because none of these businesses, not 00:21:29.529 --> 00:21:32.329 the wine, not the agency, not the NFTs, none 00:21:32.329 --> 00:21:34.450 of it works without his unbelievable ability 00:21:34.450 --> 00:21:37.240 to command attention. The man is everywhere. 00:21:37.500 --> 00:21:40.539 I open LinkedIn. He's there. I open TikTok. He's 00:21:40.539 --> 00:21:43.680 there. YouTube, Twitter. It's endless. How does 00:21:43.680 --> 00:21:47.160 one human being produce this much stuff? He doesn't. 00:21:47.160 --> 00:21:49.880 He has a big team. And more importantly, he has 00:21:49.880 --> 00:21:52.400 a system. It's a system he calls the content 00:21:52.400 --> 00:21:54.640 pyramid. And it's actually something that's really 00:21:54.640 --> 00:21:56.859 actionable for anyone listening right now. OK, 00:21:56.940 --> 00:21:59.480 please break it down for me, because I struggle 00:21:59.480 --> 00:22:03.119 to post like one good tweet a week. It's pretty 00:22:03.119 --> 00:22:06.019 simple conceptually. It all starts with one piece 00:22:06.019 --> 00:22:08.519 of pillar content. Pillar content. Yeah, that's 00:22:08.519 --> 00:22:10.839 the big thing at the top of the pyramid. It could 00:22:10.839 --> 00:22:14.119 be a long -form keynote speech he gives or a 00:22:14.119 --> 00:22:16.220 podcast interview he does or one of his long 00:22:16.220 --> 00:22:18.819 vlogs. Let's say he gives a one -hour speech 00:22:18.819 --> 00:22:22.079 on the future of marketing. That speech is the 00:22:22.079 --> 00:22:24.359 pillar. Okay, so he does the heavy lifting just 00:22:24.359 --> 00:22:27.240 once. Right. Then his content team takes that 00:22:27.240 --> 00:22:29.779 one -hour video and they just chop it up. They'll 00:22:29.779 --> 00:22:31.779 go through it and find the five funniest jokes 00:22:31.779 --> 00:22:34.700 he told, the 10 smartest business insights, the 00:22:34.700 --> 00:22:37.359 three most controversial statements. Then they 00:22:37.359 --> 00:22:40.539 turn those little moments into 30 or 40 short 00:22:40.539 --> 00:22:44.099 vertical clips for TikTok, Instagram reels and 00:22:44.099 --> 00:22:47.119 YouTube shorts. Wow. So one hour of work becomes 00:22:47.119 --> 00:22:50.000 what, 40 or 50 individual pieces of content? 00:22:50.279 --> 00:22:53.019 Easily. And that's just the video. Then they 00:22:53.019 --> 00:22:55.160 take the audio from the speech and they release 00:22:55.160 --> 00:22:57.660 it as a podcast episode. Then they get the entire 00:22:57.660 --> 00:23:00.200 speech transcribed and they turn the best parts 00:23:00.200 --> 00:23:03.279 into LinkedIn articles or long form tweets. And 00:23:03.279 --> 00:23:05.940 I've seen them take a single quote, put it over 00:23:05.940 --> 00:23:08.440 a picture of his face and post that on Instagram. 00:23:08.859 --> 00:23:13.200 Exactly. One single keynote speech can fuel all 00:23:13.200 --> 00:23:15.779 of his social media channels for an entire week. 00:23:15.900 --> 00:23:18.779 It's just maximum efficiency. It's the volume 00:23:18.779 --> 00:23:21.240 strategy we talked about with VaynerMedia. He's 00:23:21.240 --> 00:23:23.039 just applying it to his own personal brand. He 00:23:23.039 --> 00:23:25.440 is practicing exactly what he preaches. And you 00:23:25.440 --> 00:23:27.619 should notice, too, the distinct flavors of his 00:23:27.619 --> 00:23:30.019 different content shows over the years. They 00:23:30.019 --> 00:23:32.359 each served a purpose. DailyVee, for example, 00:23:32.500 --> 00:23:34.500 was a documentary series. It was like reality 00:23:34.500 --> 00:23:38.019 TV for entrepreneurs. It was. It showed the grinds, 00:23:38.019 --> 00:23:40.400 sleeping on planes, eating bad airport food, 00:23:40.480 --> 00:23:43.180 having stressful meetings at VaynerMedia. It 00:23:43.180 --> 00:23:45.220 was specifically designed to show his audience 00:23:45.220 --> 00:23:47.339 that he wasn't just some talking head who gives 00:23:47.339 --> 00:23:50.299 advice. It showed the work. And then you had 00:23:50.299 --> 00:23:52.849 hashtag AskGaryVee. Right. And that was a pure 00:23:52.849 --> 00:23:55.730 Q &A show. That was all about community engagement. 00:23:55.869 --> 00:23:58.990 He would source questions directly from his followers 00:23:58.990 --> 00:24:01.309 on Twitter and Instagram and answer them on video. 00:24:01.789 --> 00:24:04.150 That show actually became so popular that it 00:24:04.150 --> 00:24:05.950 was turned into one of his bestselling books. 00:24:06.190 --> 00:24:08.470 Let's talk about the books, because he's written 00:24:08.470 --> 00:24:10.970 a whole shelf full of them. And I think the titles 00:24:10.970 --> 00:24:13.109 themselves, if you look at them in order, they 00:24:13.109 --> 00:24:15.069 tell a really interesting story about how his 00:24:15.069 --> 00:24:17.799 own philosophy has shifted over time. They absolutely 00:24:17.799 --> 00:24:21.099 do. The timeline of his books perfectly mirrors 00:24:21.099 --> 00:24:23.720 the maturity of the Internet economy itself. 00:24:24.059 --> 00:24:27.160 OK, so you start in 2009 with Crush It. Crush 00:24:27.160 --> 00:24:29.859 It. That was the original manifesto. The subtitle 00:24:29.859 --> 00:24:33.039 was Why Now Be Is the Time to Cash In on Your 00:24:33.039 --> 00:24:35.500 Passion. And you have to remember the context. 00:24:35.619 --> 00:24:37.759 It came out in 2009 right on the heels of the 00:24:37.759 --> 00:24:39.960 massive financial crash. People were desperate. 00:24:40.059 --> 00:24:41.759 They were losing their jobs. They were desperate. 00:24:41.839 --> 00:24:43.660 And he was coming in with this message saying 00:24:43.660 --> 00:24:46.059 the gatekeepers are gone. The Internet is here. 00:24:46.589 --> 00:24:49.250 Start a blog about what you love, work harder 00:24:49.250 --> 00:24:52.269 than everyone else, and you will win. It was 00:24:52.269 --> 00:24:55.950 pure, raw, unapologetic aggression. Then you 00:24:55.950 --> 00:24:59.329 get into the more tactical stuff, like Jab, Jab, 00:24:59.390 --> 00:25:02.509 Jab, Right Hook. Which is still, in my personal 00:25:02.509 --> 00:25:05.710 opinion, his best pure business book. The entire 00:25:05.710 --> 00:25:08.109 thesis is right there in the title. Give value, 00:25:08.250 --> 00:25:10.289 give value, give value. Those are the jab. And 00:25:10.289 --> 00:25:12.670 only then do you ask for the sale, which is the 00:25:12.670 --> 00:25:15.460 right hook. Most businesses just throw right 00:25:15.460 --> 00:25:17.680 hooks all day. Buy my stuff, buy my stuff, here's 00:25:17.680 --> 00:25:20.900 a coupon. He explained very clearly that on social 00:25:20.900 --> 00:25:23.380 media you have to earn the right to sell to somebody. 00:25:23.640 --> 00:25:26.099 But then more recently, the whole tone of the 00:25:26.099 --> 00:25:30.099 books changed. It got softer. In 2021, he released 00:25:30.099 --> 00:25:32.779 a book called Twelve and a Half. This was a massive 00:25:32.779 --> 00:25:35.819 pivot, a huge one. The subtitle is Leveraging 00:25:35.819 --> 00:25:37.940 the Emotional Ingredients Necessary for Business 00:25:37.940 --> 00:25:40.500 Success. We are not talking about crushing it 00:25:40.500 --> 00:25:42.319 anymore. We're talking about empathy, kindness, 00:25:42.599 --> 00:25:45.420 self -awareness, curiosity, gratitude. So what 00:25:45.420 --> 00:25:47.420 prompted the shift? Did he just get soft in his 00:25:47.420 --> 00:25:50.349 older age? Or did he realize that hustle culture, 00:25:50.450 --> 00:25:52.650 the very thing he helped create, was becoming 00:25:52.650 --> 00:25:55.210 toxic? I think he absolutely read the room. The 00:25:55.210 --> 00:25:57.589 whole hustle porn era, you know, where founders 00:25:57.589 --> 00:25:59.829 would brag about sleeping only four hours a night, 00:25:59.910 --> 00:26:02.490 that was facing a massive cultural backlash. 00:26:02.829 --> 00:26:04.410 People were burning out. People were burning 00:26:04.410 --> 00:26:06.509 out. And the Gary Vee character was, frankly, 00:26:06.609 --> 00:26:08.309 becoming a bit of a villain in that narrative. 00:26:09.049 --> 00:26:11.789 Twelve and a half was his direct attempt to add 00:26:11.789 --> 00:26:14.900 nuance to his own message. He started arguing 00:26:14.900 --> 00:26:16.859 that you can work incredibly hard without being 00:26:16.859 --> 00:26:20.000 miserable or being a terrible boss. He started 00:26:20.000 --> 00:26:23.619 talking about things like kind candor. Kind candor. 00:26:23.619 --> 00:26:26.099 I like that phrase. It's a great phrase. It basically 00:26:26.099 --> 00:26:28.359 means you have to be able to tell people the 00:26:28.359 --> 00:26:31.769 hard truth Firing someone, giving critical feedback, 00:26:32.130 --> 00:26:34.369 but you have to learn how to do it from a place 00:26:34.369 --> 00:26:36.690 of kindness and respect without being a jerk. 00:26:36.970 --> 00:26:39.910 It was an attempt to merge that hard -nosed businessman 00:26:39.910 --> 00:26:43.029 persona with a more modern, emotionally intelligent 00:26:43.029 --> 00:26:45.990 leader. But let's be real. The criticism has 00:26:45.990 --> 00:26:48.369 not gone away. There are plenty of people, as 00:26:48.369 --> 00:26:50.549 noted in our sources, who still view him as a 00:26:50.549 --> 00:26:53.809 snake oil salesman. Yes. And it's important that 00:26:53.809 --> 00:26:56.089 we really apply some critical thinking here and 00:26:56.089 --> 00:26:59.490 analyze why. The term snake oil implies you're 00:26:59.490 --> 00:27:01.930 selling a cure that doesn't actually work. Right. 00:27:02.329 --> 00:27:04.490 The criticism of Gary usually fall into two main 00:27:04.490 --> 00:27:07.730 buckets. The first one is what's called survivorship 00:27:07.730 --> 00:27:10.650 bias. Okay, explain that. The critics will say, 00:27:10.789 --> 00:27:13.109 okay, Gary, you made it. That's great for you. 00:27:13.210 --> 00:27:16.950 But for every one of you, there are 10 ,000 kids 00:27:16.950 --> 00:27:19.950 who listened to your advice, dropped out of college 00:27:19.950 --> 00:27:23.230 to build their personal brand, and ended up completely 00:27:23.230 --> 00:27:26.109 broke. That's a very valid point. The odds are 00:27:26.109 --> 00:27:28.430 not in your favor. Not everyone can be a media 00:27:28.430 --> 00:27:31.339 mogul. It's a totally fair point. The second 00:27:31.339 --> 00:27:33.680 main criticism is about the productization of 00:27:33.680 --> 00:27:36.700 self. And the question is this. Is he selling 00:27:36.700 --> 00:27:40.039 actionable business advice or is he selling the 00:27:40.039 --> 00:27:42.500 feeling of being successful? That's a good distinction. 00:27:42.720 --> 00:27:44.799 Think about it. When you watch a Gary Vee video, 00:27:44.980 --> 00:27:47.259 you get a little dopamine hit. You feel motivated. 00:27:47.359 --> 00:27:49.839 You feel energized. But after that 10 minutes, 00:27:49.920 --> 00:27:51.859 did you actually learn how to read a balance 00:27:51.859 --> 00:27:54.079 sheet or did you just feel good for a little 00:27:54.079 --> 00:27:57.220 while? It's the idea of entrepreneurship. People 00:27:57.220 --> 00:27:59.680 who are addicted to consuming content about business 00:27:59.680 --> 00:28:02.240 instead of actually doing the business. Exactly. 00:28:02.299 --> 00:28:05.180 And to be fair, Gary would argue that he puts 00:28:05.180 --> 00:28:07.579 out thousands of hours of free tactical content 00:28:07.579 --> 00:28:09.940 so you can do the business. He would say, I gave 00:28:09.940 --> 00:28:12.079 you the entire blueprint for free. Don't blame 00:28:12.079 --> 00:28:15.059 me if you didn't build the house. But that critique 00:28:15.059 --> 00:28:18.599 remains. Does his high energy style accidentally 00:28:18.599 --> 00:28:21.339 attract people who are looking for a magic bullet, 00:28:21.380 --> 00:28:24.019 even though he explicitly says over and over 00:28:24.019 --> 00:28:26.819 that there are no shortcuts? And yet. Despite 00:28:26.819 --> 00:28:29.559 the critics, his ambition hasn't slowed down 00:28:29.559 --> 00:28:33.920 one bit. He still talks constantly about his 00:28:33.920 --> 00:28:36.960 ultimate goal, buying the New York Jets. That 00:28:36.960 --> 00:28:39.380 is the North Star. That's the end goal of all 00:28:39.380 --> 00:28:42.519 of this. He's a diehard, lifelong Jets fan, and 00:28:42.519 --> 00:28:44.500 he has said publicly for years that his entire 00:28:44.500 --> 00:28:47.000 career, all of these businesses, they are just 00:28:47.000 --> 00:28:49.480 a mechanism to accumulate enough capital to one 00:28:49.480 --> 00:28:51.880 day buy the team. You know, it's almost a protective 00:28:51.880 --> 00:28:54.119 mechanism, isn't it? As long as he hasn't bought 00:28:54.119 --> 00:28:56.210 the Jets yet, he's still... on the journey. He 00:28:56.210 --> 00:28:58.250 hasn't truly won the game yet. That's a great 00:28:58.250 --> 00:28:59.730 psychological insight. I think you're right. 00:28:59.809 --> 00:29:02.390 If he actually buys the Jets tomorrow, what's 00:29:02.390 --> 00:29:04.769 left? The game is over. By keeping that goal 00:29:04.769 --> 00:29:07.829 so impossibly high, he ensures that the hunger 00:29:07.829 --> 00:29:10.390 never goes away. So we've covered a lot of ground. 00:29:10.490 --> 00:29:12.609 The immigrant hustle, the wine empire, the ad 00:29:12.609 --> 00:29:15.630 agency dominance, the tech exits, the NFTs, the 00:29:15.630 --> 00:29:18.299 books, the philosophy. For the listener who is 00:29:18.299 --> 00:29:20.220 maybe sitting in a cubicle right now or maybe 00:29:20.220 --> 00:29:22.740 trying to run a small business, what is the actual 00:29:22.740 --> 00:29:25.200 practical takeaway here beyond just the you can 00:29:25.200 --> 00:29:27.559 do it cheerleading? If you strip everything else 00:29:27.559 --> 00:29:29.559 away, the single biggest takeaway is adaptation. 00:29:29.920 --> 00:29:31.740 Just look at the timeline one last time. Okay. 00:29:32.119 --> 00:29:36.039 1998. Email is the new undervalued asset he goes 00:29:36.039 --> 00:29:39.369 all in. 2006. YouTube is the new undervalued 00:29:39.369 --> 00:29:42.029 asset. He goes all in. 2011, corporate social 00:29:42.029 --> 00:29:44.210 media is the asset. He builds an entire agency 00:29:44.210 --> 00:29:48.450 around it. 2021, Web3 and NFTs are the new frontier. 00:29:48.769 --> 00:29:50.910 He builds VFriends. He never fell in love with 00:29:50.910 --> 00:29:52.930 the medium. Never. He didn't say, I'm a newsletter 00:29:52.930 --> 00:29:56.150 guy or I'm a YouTuber. He said, I am a trader 00:29:56.150 --> 00:29:58.710 of attention. That's the key. Don't fall in love 00:29:58.710 --> 00:30:01.190 with your tools because the tools always, always 00:30:01.190 --> 00:30:04.569 change. The tools always change. The consumer 00:30:04.569 --> 00:30:08.250 behavior changes. The platforms change. The only 00:30:08.250 --> 00:30:10.390 thing that stays the same is that people are 00:30:10.390 --> 00:30:12.890 paying attention to something. And your job, 00:30:12.890 --> 00:30:15.349 whether you are selling wine or widgets or just 00:30:15.349 --> 00:30:17.990 yourself, is to find out where those eyes are 00:30:17.990 --> 00:30:19.930 going before the price of admission goes up. 00:30:19.990 --> 00:30:22.109 And to not be afraid to look a little bit stupid 00:30:22.109 --> 00:30:24.230 while you're doing it. I mean, he looked ridiculous 00:30:24.230 --> 00:30:27.049 spitting wine into a bucket in 2006. He looked 00:30:27.049 --> 00:30:28.789 ridiculous to a lot of people talking about cartoon 00:30:28.789 --> 00:30:32.059 NFTs in 2020. Being willing to be misunderstood 00:30:32.059 --> 00:30:35.799 for long periods of time is an absolute superpower 00:30:35.799 --> 00:30:38.619 in business. He was willing to be the crazy wine 00:30:38.619 --> 00:30:42.220 guy for years until suddenly he was the genius 00:30:42.220 --> 00:30:44.680 marketing guy. Before we wrap this up, I want 00:30:44.680 --> 00:30:46.000 to leave the listeners with a final thought. 00:30:46.410 --> 00:30:48.170 Something for them to chew on that maybe isn't 00:30:48.170 --> 00:30:50.430 in the books or the speeches. I have one. It's 00:30:50.430 --> 00:30:52.750 a question really for you to consider. We've 00:30:52.750 --> 00:30:55.130 established that Gary Vaynerchuk is an absolute 00:30:55.130 --> 00:30:57.509 master of content. He meticulously documents 00:30:57.509 --> 00:30:59.829 his life in order to sell his businesses and 00:30:59.829 --> 00:31:02.390 his philosophy. But at this point in his career, 00:31:02.470 --> 00:31:05.990 you have to ask yourself, is the business driving 00:31:05.990 --> 00:31:09.210 the content or is the content now the actual 00:31:09.210 --> 00:31:11.779 business? Wait, what do you mean by that? I mean, 00:31:11.819 --> 00:31:14.700 does VaynerMedia primarily exist to serve clients 00:31:14.700 --> 00:31:17.299 like PepsiCo? Or does it exist to provide the 00:31:17.299 --> 00:31:19.779 perfect backdrop for Gary's content about being 00:31:19.779 --> 00:31:24.359 a CEO? Has he productized his own life so effectively 00:31:24.359 --> 00:31:27.180 that the story of him doing business has become 00:31:27.180 --> 00:31:29.500 more valuable than the business itself? That 00:31:29.500 --> 00:31:32.759 is a real inception level thought. Is he a businessman 00:31:32.759 --> 00:31:35.289 who is playing a character on the Internet? Or 00:31:35.289 --> 00:31:36.829 is he a character on the internet who is playing 00:31:36.829 --> 00:31:39.650 a businessman? Or perhaps in the modern attention 00:31:39.650 --> 00:31:41.970 economy, there really is no difference between 00:31:41.970 --> 00:31:44.670 the two anymore. On that bombshell, we are going 00:31:44.670 --> 00:31:47.049 to sign off. Thank you for taking this deep dive 00:31:47.049 --> 00:31:49.450 with us. Now stop watching us and go spot some 00:31:49.450 --> 00:31:50.750 arbitrage. See you next time.