Live From The HIBT Summit: Gary Vaynerchuk

We have another episode from the 2021 How I Built This Virtual Summit, and it's Guy's interview with internet content guru Gary Vaynerchuk. In this live conversation, Gary talks about his innovative approaches to marketing and branding, and his belief that you can make money from pretty much anything online, as long as you're passionate about it, and put in the work. We'll be releasing more episodes from the Summit throughout the month of August, so keep checking your podcast feed. See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

Speaker names marked ? are inferred from speaking time and the show’s known hosts — they are not voice-verified.

• 0:00Guy Raz?

  Our presenting sponsor today is Anthropic, the team behind Claude. Every founder on this show started with a hard question. Not the marketing plan, the 2 a.m. kind. Is this idea any good? Am I the one to build it? Should I quit my job? Anthropic got built the same way. A public benefit corporation founded on one hard question. How do we make sure AI goes well for people? So they asked over 100,000 people their hopes and their fears and are publishing what they find, even the uncomfortable parts. Me? I've got my own hard question about AI. Here it is. If everyone has access to something that can help them write the business plan,

• 0:46Guy Raz?

  build the prototype, analyze the market, maybe even come up with the idea, what separates the people who actually build something from everyone else? I don't have a clean answer yet, so I've been sitting with it with Claude. There's hope in hard questions. Ask yours at claude.ai/hibt. We get support from U.S. Bank. A question I love asking founders. What's the one decision you almost didn't make? The one that changed everything? Because it's never the obvious stuff. It's never, I decided to start a company. It's the small, boring, Tuesday afternoon decision you barely remember making until you realize it's the reason everything after it either worked or didn't.

• 1:32Guy Raz?

  Say you're 18 months in. Business is growing. You've got expenses coming from six directions. Gas for the van, office supplies, your phone bill, team lunches that are actually client meetings, and you're putting it all on whatever card you grabbed in year one. You're not thinking about it. Why would you? You've got bigger problems. But here's the thing. Path A, you keep going like that. End of the year, you're sorting through statements, trying to figure out what went where. You've left hundreds, maybe thousands on the table in rewards you never earned, money that could have gone back into the business. Path B, you pause and get The US Bank Triple Cash Rewards Visa Business Card.

• 2:14Guy Raz?

  Now you're earning 3% cash back on gas and EV charging, office supply stores, cellphone service, and restaurants. You pick up an extra $750 cash back as a bonus. And you've got a low APR on purchases and balance transfers for 12 months while you're scaling. Same business, same expenses, two completely different outcomes based on one small decision. Visit usbank.com/business to learn more. The creditor and issuer of this card is US Bank National Association pursuant to a license from Visa USA Inc. Some restrictions apply. If you travel often, you'll want to hear about this unprecedented offer.

• 2:58Guy Raz?

  For the first time ever, new Delta SkyMiles Reserve American Express Card members can earn two Delta Comfort round trip flights for travel within the 48 contiguous US states, Puerto Rico, or the US Virgin Islands. Plus, you can earn 50,000 bonus miles towards your next getaway. And who doesn't appreciate an elevated airport experience? Delta SkyMiles Reserve Card members get access to the Delta Sky Club, your pre-flight oasis to recharge with 15 visits and four one-time guest passes each medallion year when flying Delta together. That's up to $950 in annual value.

• 3:40Guy Raz?

  Value estimate based on $50 per visit rate to purchase additional visits or bring a guest to the Delta Sky Club. Make every trip feel more rewarding with the card that upgrades your travel. Apply today at delta.com/cardsocial. Offer ends November 4, 2026. Minimum spending requirements and terms apply. Flights are fulfilled as flight certificates valid for Delta Comfort or Delta Maine to select domestic destinations. Book 21-plus days in advance. Up to $80 per person and taxes and fees apply. Other restrictions apply. When I pull up to a gas pump to fill my car, I'm not thinking about chemistry or engineering. I'm thinking about getting in, filling up,

• 4:21Guy Raz?

  and getting on with my day. And it reminds me a little bit of the founders I talked to on this show, because the best ones obsess over things their customers will never see: tiny details, invisible improvements, relentless iteration. And not because anyone's watching, but because it makes the product better. That's what the mobile brand does. It engineers fuel the same way great founders engineer their products. Mobile Supreme Plus Premium Gas helps keep engines three times cleaner, which can mean better performance and improved gas mileage. It's for people who care about what's under the hood, even if they never see it. Three times cleaner compared to mobile regular

• 5:03Guy Raz?

  gas in port fuel-injected engines. Actual results may vary. Visit mobili fuels.com for details. Hello, everyone, and welcome to a very special edition of How I Built This from NPR. I'm Guy Raz. So, back in May, we held our first-ever live virtual How I Built This Summit. And most of the time, we do it in person, but for obvious reasons, we had to go virtual this year. But still, more than 3,000 people from around the world attended. So throughout this summer, we're going to release a bunch of our conversations from the summit right here on the podcast. And today, we've got my interview with entrepreneur, author, and social media guru Gary Vaynerchuk. And before we dive in, I should point out

• 5:47Guy Raz?

  that in your podcast queue right now is my other interview with Gary. It's a full studio interview, and it's his whole life story. And it's so interesting and amazing. And if you haven't listened to it already, you definitely should. And it'll make this conversation you're about to hear even better. And if you've already listened, and you're thinking, wait, aren't they just going to go over what they talked about in the other interview? I promise you, the answer is no. There is so much more great stuff I talked about with Gary at our virtual summit, all focused on his innovative approaches to marketing and branding. So I'm probably not the first person to describe Gary as a content-making

• 6:28Guy Raz?

  machine. Years ago, he saw the early potential of YouTube, and he launched a very funny and irreverent show about wine, which gained him a huge following and sparked dozens of other ventures. And today, he's got millions of followers on pretty much every possible platform. Gary built an industry around the idea that you can pretty much sell almost anything online, as long as you're passionate about it and you put in the work. Gary, to say the least, makes a ton of content, and not just content, but compelling content about how to, well, make compelling content. So here's my conversation with Gary

• 7:10Guy Raz?

  Vaynerchuk from the 2021 How I Built This virtual summit. Enjoy. Gary, normally I wouldn't take the time to ask you about the lemonade stand you ran as a kid. This was, I believe, in New Jersey. But apparently, yours wasn't just a stand, it was an entire franchise. How did you franchise your lemonade stand as a kid?

• 7:33Speaker 01

  By being so nice to my friends every other day of the week that they felt compelled that when I asked to stand behind the table, that they would say yes. So I learned very early on that it wasn't bribery or money. It was that my friends liked me for all the other variable things. So when I would go in for the ask, they felt compelled or guilted into doing it. And so I had multiple kids in the neighborhood that were pretty signed up for, hey, this is your location. This is not a joke. I would actually ride a big wheels. I didn't even have an actual bike yet. The old, like, big wheels.

• 8:09Guy Raz?

  Oh, yeah.

• 8:10Speaker 01

  And I would go around to my stands like I was Tony Soprano.

• 8:16Speaker 01

  For me to be that young, six, seven, eight, and for it to come so natural to me, you know, I think about sports or musicians. You see those videos of Beyonce or LeBron and you're just like, right, of course. That's me in business, you know, we didn't film those things. But, you know, I, I just kind of always knew what I loved and what was interesting to me and what came natural to me and what was, and I refined those skills in my youth and I think that gave me a head start in what I do today.

• 8:48Guy Raz?

  All right, I want to push back for a sec because I think that's true. I do think that you are a gifted and natural entrepreneur. But most of us aren't, most of us don't have those gifts and we have to build them up, right? You had, I remember in our conversation, you talked about working in your dad's liquor store. And your dad, and you were like, Dad, you gotta sell wine. And he's like, wine? And you're like, yeah, and you've got to, you've got to position it like this. So when people come in, you know, and you figured out how to get people to linger and chat and then buy wine. So you had an instinct, so this may be hard for you to deconstruct this.

• 9:22Speaker 01

  Well, well, but, but let me deconstruct it. I'm sorry to interrupt, but like, you know, by the time I was 15, saying that to my dad, I had done

• 9:32Speaker 01

  a hundred baseball card shows and me moving around my table and understanding locations in the mall. Or like, you know, it was, yes, I agree, but it was reps, right? It was shooting baskets, like some people are born with better hand eye coordination, but you shoot 10,000 baskets, you're going to be a little bit better than the one who's not. And so, yeah, I think for, you know, one of the things I'm fascinated by is I know right now I could be better at skiing, music, singing, tennis, and pretty much most things. Do I think I could be at a Hall of Fame level on a lot of those? Probably not. Do I think every one of those things could be dramatically better? I, I do.

• 10:17Speaker 01

  And then the question becomes, you know, why do people become much better at golf? Because they genuinely enjoy it. It's what they want to do for recreation and they get better at it. To me, I've always thought of that in the context of professionalism. You know, what if you didn't do what you were supposed to do or what your parents wanted you to do or what you thought you could make the most money with the quickest? What if you kind of focused on the things that were intriguing to you, which inherently would make you put in the reps? What would that look like in a 20-year window? I still am incredibly fascinated by that thesis.

• 10:54Guy Raz?

  Um, but I didn't know you sing. Do you sing, really?

• 10:57Speaker 01

  I can't sing for crap.

• 10:58Guy Raz?

  Okay, I was just, I was taken aback for a moment.

• 11:01Speaker 01

  But if I did go to singing lessons, I have a funny feeling I'd be much better than I am today in four years. I have a funny feeling I'm not Beyonce. Um, but I, but I, but I definitely think it would be better than I am today.

• 11:19Guy Raz?

  All right. You were very early on with your, your dad's liquor business. You got into Google AdWords and I mean, and in a website where nobody was doing it and, um, and then eventually, you know, YouTube, using YouTube as a, as a marketing tool for Wine Library TV, um, which really kind of transformed you into a brand. Gary Vee became a brand through this and you began to write books and, um, and talk about how people could make money on the internet in part by making content.

• 11:52Speaker 01

  Yes.

• 11:53Guy Raz?

  Is that still part of your message today?

• 11:55Speaker 01

  Yes. I mean, I think the right, if you read Crush It today, 13 years after I wrote it, um...

• 12:05Speaker 01

  You know, I'm talking about influencer marketing. I'm talking about podcasts. I'm talking about everything that ended up happening. You know, the book, when you deconstruct it is, you know, if you're, if you're not knowledgeable about wine or jujitsu or, you know, harvesting honey, you know, that's going to hurt you. If you're not deeply interested in the community around those interests, you're not going to be able to cultivate lifetime value. It's very hard to put in that community time and that, and have content that hits unless that layer of making content money comes from a place where you're bringing so much value

• 12:47Speaker 01

  to the audience that things start to happen, right? People want to do things with you. Your audience wants to buy things from you. So it's a really interesting game of selflessness that drives selfishness. But yes, I don't think 13 years ago, people realized how much democracy would be coming to content consumption, that it was not relegated to television, print, radio, NPR, ABC, and that the internet was going to be distribution. And if you found your way of communication, whether through video, audio, written word, there was going to be opportunity on the other side of it.

• 13:24Guy Raz?

  Gary, there are people who are attending the summit who are many startup, startup founders, who are, you know, doing things from like a flower business to people who, who are providing services for, you know, consulting services, to people who are creating products. Do you believe that anything can be turned into an interesting content story? Do you think that if somebody cares enough about their thing, even if it, if it might seem a little boring on the face of it, you can turn it into something interesting through content?

• 14:00Speaker 01

  I think that niches are a much longer tail than people think.

• 14:06Speaker 01

  But I don't believe all of them have the size of macro intrigue that make it something that we would all who are listening say, oh, that's like a very lucrative opportunity. You know, Frisbee, right? Do I think that you can amass 150,000, 500,000, 4 million people into a group on Facebook? And I'd start a podcast and I do, I really do Frisbee golf, like I really, really do. And I continue to believe this. A person who's obsessed with Frisbee golf or Frisbee or what have you. Is she or he more excited about the notion of making $86,000 a year and living that lifestyle?

• 14:51Speaker 01

  Doing Frisbee every day because they were able to get a $25,000 sponsorship from the biggest thing? Frisbee person and YouTube apps, this and this and that. Versus a buck 30 being a director at a company that makes the miserable. That to me is the centerpiece of this argument because if, if it's wine, you could build a multi-million dollar company because there's enough interest in wine. Yeah. Even as a niche. If it's professional basketball, you could go on to create a seven-figure business easily for yourself. If it's the Red Power Ranger, not even Power Rangers, the Red Power Ranger.

• 15:31Speaker 01

  You know, you're now starting to look at a five-figure monetization at scale strategy. Or maybe six, if you know, Comic Con this and this and that. So, you know, I wanted to break that down since we had time together. Yeah. There's a, I do think almost everything, it's stunning what people collect are interested in. To sit and say, you can then make a career out of it. Believe it or not, I, I probably go way further down the long tail than most people. Because I know about affiliate deals on eBay. I know that if you really grind it and work hard and reach out to certain companies, there's, there's branding deals to be had. But obviously, if you're talking about music, there's going to be a lot more general.

• 16:15Speaker 01

  Intrigued as you go down, if you go to Christian Rock, it might even be more lucrative because it's narrow, but it's still big enough. So those are the things I think through when I think about that question.

• 16:25Guy Raz?

  All right, you're so so some of this obviously applies to creators or content creators or. But what about somebody who has a product or a service that they're offering? Let's say, you know, somebody watching now who has a business. How central in your view is creating a content strategy around their business if they want to scale and grow?

• 16:45Speaker 01

  For me, it's top three things in 2021 because I think about growth, Guy. Do I think that there's millions of businesses that are chugging along, doing just fine without content? Of course I do, but I just know them to be true. Do I look at every one of those businesses and say to myself, if she knew that if she put $55,000 into an employee and some ads, that her top line revenue would go up by 200K, thus paying like, I believe that. So the answer is for me, I have no idea why somebody would leave the growth on the table

• 17:22Speaker 01

  in a world now where the cost of creative and ad arbitrage on Facebook, TikTok, LinkedIn is so extreme that there's a land grab of opportunity. I don't know why somebody would leave that on the table. What I see is some people are philosophically just against it because they're content, which is incredible. I'm thrilled for them. And then there's another group that tried it, failed because of lack of patience or because they weren't educated enough of how to judge the people that were doing it for them and have decided this doesn't work without realizing it was they that were the reason it didn't work. It's kind of like exercising for two weeks, not getting a six pack and being like, well, this doesn't work.

• 18:05Guy Raz?

  Yeah.

• 18:06Speaker 01

  So that's how I would answer that question.

• 18:08Guy Raz?

  You know, it's interesting because we have an episode of How I Built This about Policy Genius, the insurance marketplace, it's like Kayak or Expedia for insurance. And Jennifer Fitzgerald, she tried to raise a million dollars, she couldn't. They ended up raising under $700,000 to start this business, which today has 30 million users. But they couldn't raise a whole lot of money. It was it was Jennifer and her co-founder Francois. Their third hire was a content person to write articles about the insurance industry on their website.

• 18:40Guy Raz?

  And I said to her, how were you able to measure success in that first year? And she said, we weren't. We didn't know if anybody was reading these articles. But eventually, they started to rise up in search engine queries. And today, most people go to Policy Genius to learn about insurance. Some of them buy insurance, some of them don't. But that's been central to their strategy.

• 19:02Speaker 01

  It's, everything you just said is biggest things I believe in the world. And that is intent-based marketing. Because you're writing articles to win the arbitrage of SEM, where people are typing things in in Google with intent, and then you show up. Which I love, intent-based marketing. I also, what I love about social media, is that is more classic brand awareness marketing that used to be left for the biggest brands in the world. Coca-Cola, Disney, Delta. Because the way those society worked was television, print, and radio were the places we were consuming information.

• 19:42Speaker 01

  The costs of full-page ads in the New York Times and running commercials on television were so extraordinary that the attention sat at the top, and that's why you got the Procter and Gables, and the Coca-Colas, and the Deltas. Now, we have awareness, discovery, happening in Instagram and in TikTok, which has completely democratized the ability to brand. And so, you could have something like, I'll give you a great example. The Ocean Spray viral video, right?

• 20:15Guy Raz?

  Oh, yeah.

• 20:15Speaker 01

  Right? That is the single most impactful ad in the history of Ocean Spray Cranberry.

• 20:21Guy Raz?

  Yes.

• 20:21Speaker 01

  Done by a man that wasn't in the company, nor hired by an agent, as an agency.

• 20:27Guy Raz?

  Right.

• 20:28Speaker 01

  There are things going on now, because TikTok's virality, that are just extraordinary. And, um, and most of the world has not caught up to that. People are transactional in digital marketing. So they look for the CAC and the LTV, the customer acquisition cost, the lifetime value. They're salespeople. The branding people still live in television and kind of like, business school, how to build a brand, and aren't contemporary in where they do create a brand building. And so what you have is this vacuum, this incredible...

• 21:04Speaker 01

  Situation currently guy in the world where very few people actually understand that you can build brand, brand on social at very low costs. And I believe that that is where the opportunity sits today.

• 21:17Guy Raz?

  So Gary, if somebody watching today and most, most of the attendees that are in our community, you know, they're not, they don't have million dollar ad budgets or marketing budgets. They can't, you know, with all due respect, they can't afford VaynerMedia, you know, which is a, right? You work with Fortune 500, but if you were to say to somebody, look, if somebody says, said to you, well, Gary, how do I start? How do I create content with limited resources and limited time? Where do I even begin? What do you, what do you say?

• 21:47Speaker 01

  I say a couple of things. I say, look, if you want to grow and you have limited resources, your actual resources, your ability to be educated and you allocating the time. When people say to me, well, I don't have time. You know, when I audit and I do that for my best friends, my acquaintances, distant relatives randomly because I'm in the mood sometimes. Guy, what people realize is they waste an extraordinary amount of time every day. If you talk to somebody who has six employees and has a business, she or he often is micromanaging that they have no reason to be micromanaging. They have hour meetings that can be 15 minute meetings. And miraculously, every time I've done a CAT scan, an MRI, an

• 22:28Speaker 01

  audit, we have found three hours a day miraculously from people that have no time. Then what I say is now that we found three a day, a day, and that gives me 15 for the week, I want the first two weeks to be completely education. Give me 30 hours of education. Watch these YouTube videos. Read these tutorials that are free on the internet. Here, you know, here, you know, Google away. How do I make a LinkedIn post for a lawyer? How to, you know, make a podcast? How to write articles that succeed on LinkedIn? It's all there.

• 22:58Guy Raz?

  Yeah.

• 22:59Speaker 01

  Guy, it's all there. 30 hours. Then the next 30 hours, which is now obviously the first month's formula. So the next two weeks, 30 hours belongs to you. You, the proprietor, you make content for 30 hours. Let me tell you why. Whether it's writing, whether it's recording an audio clip on your iPhone, or whether you're comfortable in video, which is smaller, but obviously high impact. You can't, as a business owner, judge when you can finally afford to hire someone or use an agency, the work, if you don't understand it. The greatest vacuum in the last decade, guys, is that people have been hiring people to do social media work,

• 23:44Speaker 01

  and they have no idea how to judge a jury. They have no clue.

• 23:48Guy Raz?

  Yeah.

• 23:48Speaker 01

  So they're like, how is this? It's just a black box. And so I believe that if you audit your days, everybody's listening right now. I don't have those three hours. You really do. It's stunning how much time people spend on things that they're just accustomed to doing. It's, this is what I do. Well, couldn't you have that person do it? Like, this is what I like. And so, once I get those 60 hours in that month and use that formula of 30 and 30, then you make decisions. And then, you know, what I've heard from people, and I've been doing this a long time, some people fall in love with it, and they become the content producer that they never, ever dreamed of. And so, that's a very practical answer. Like, you have that level of control as a small business owner, and that's what I think you should do.

• 24:33Guy Raz?

  Gary, you, and we talk about this.

• 24:34Speaker 01

  And Guy, I apologize. This is final thought.

• 24:36Guy Raz?

  Yeah, please.

• 24:37Speaker 01

  Everything I just said, I did for seven years.

• 24:40Guy Raz?

  Yeah.

• 24:40Speaker 01

  For seven years before I hired anyone. Seven years I did my own content, all of it.

• 24:48Guy Raz?

  When we come back in just a moment, more of my conversation with Gary Vaynerchuk about which brands he thinks are doing some excellent marketing right now, and why. Stay with us. I'm Guy Raz, and you're listening to How I Built This from NPR.

• 25:08Guy Raz?

  Does your team want a website that looks and feels handcrafted, but is still fast to ship? Well, Framer is built exactly for that. With Framer, you design on a visual canvas with responsive layouts, hosting, and a CMS built in, so the work is production-ready from day one. And you can Get it done with help from Framer's AI Agents. Framer is the AI website builder that helps creators, teams, and businesses ship production-ready sites faster than ever while getting every detail right. Prompt, inspect, edit, and publish in one place at a whole new pace. AI agents and humans work together.

• 25:50Guy Raz?

  The agents bring speed and scale, and people bring taste, judgment, and control. Learn how you can get more out of your site from a Framer specialist or get started building for free today at framer.com/built for 30% off a Framer Pro Annual Plan. That's framer.com/built. Rules and restrictions may apply. AI isn't just opening new business opportunities, it's changing the way businesses get work done. The questions they ask, the decisions they make, the routine tasks they can hand off, that's the idea behind NetSuite Next, the next generation of NetSuite with AI woven into the tools your business already relies on.

• 26:35Guy Raz?

  NetSuite Next surfaces insights exactly when you need them, puts agents to work on routine tasks and problems, and lets you ask complex questions in plain language, like talking to a knowledgeable colleague. But technology is only part of the story. AI is also reshaping how people and teams work together, and that shift is already underway. That's why NetSuite wants to put a new expert-created business guide in your hands today. It's called Aligning for the Agentic Era: How AI is Changing Everyday Work. And right now, it's yours, absolutely free. Inside, you'll discover how AI could reshape work across your entire organization, and how to position your business to prosper from it.

• 27:20Guy Raz?

  If your revenues are at least in the seven figures, get NetSuite's free business guide, Aligning for the Agentic Era: How AI is Changing Everyday Work, at netsuite.com/built. The guide is free to you at netsuite.com/built. netsuite.com/built.

• 27:39Guy Raz?

  Stripe is built for whatever comes next because the pace of change has never been faster than it is right now. New business models, new currencies, and new expectations for speed, reliability, and scale. Stripe builds financial infrastructure that helps businesses start, grow, and operate globally. From payments and billing to fraud protection and cross-border payouts, Stripe is built to support the new pace of commerce. They're trusted by the companies building at the frontier, from 86% of the Forbes AI 50 to global leaders like Salesforce and OpenAI.

• 28:18Guy Raz?

  In fact, more than 1.6% of global GDP flows through Stripe, with Stripe's users processing a combined $1.9 trillion last year. So if you're already thinking about what's next for your business, see what's possible at stripe.com.

• 28:45Guy Raz?

  Hey, welcome back to How I Built This. I'm Guy Raz. So as part of this year's How I Built This Summit back in May, I spoke with social media expert Gary Vaynerchuk, and the topic was branding and marketing. Here's more of that conversation.

• 29:02Guy Raz?

  You have a massive following today, and you built that up over time, very methodically and very slowly. But if you are starting a business today and you want to do a version of the same thing, it may not be quite the same. How do you advise people to create content that is meaningful and not just a bunch of noise? Because earlier you mentioned passion and devotion, but passion and devotion is one thing. How do you actually create content that's half decent?

• 29:31Speaker 01

  The audience will decide, and I think if you look at it, value comes in a couple places. I think about two Es a lot, Guy. Expertise or escapism?

• 29:45Speaker 01

  So if somebody's listening right now, two things that have always worked to Guy's question is, do you have expertise in what you're talking about? And you have to have humility here and self-awareness. Like, you know, some people are like, "I'm an expert," and really, you're just an enthusiast. Do you have expertise? Or can you create escapism? Escapism comes in many shapes and forms. It's really entertainment, or something that's of interest, right? For example, being funny is an incredible tool of escapism.

• 30:21Guy Raz?

  Yeah.

• 30:21Speaker 01

  You made somebody laugh, they stopped thinking about their day. But I think it requires someone saying, "Okay, I'm passionate about video games. How am I gonna build a big Twitch channel?" It's gonna come from that you're epic at Fortnite, and people are just watching you out of awe of your skill set, expertise, or you might just be solid, but you're so damn compelling while you're playing, and you're storytelling, you're making people laugh, you've got a personality trait, charisma. You know, I tell everybody I meet in real life that just oozes charisma. I'm like, "Hey, have you considered this content thing?"

• 30:58Guy Raz?

  Uh huh.

• 30:58Speaker 01

  Like, if you translate the way you do in this room right now to that medium, it's gonna be something that may lead to something. So I, I think the answer is, you know, for me, I think the reason I've been able to build to where I've been able to build to is, I ended up having both without even truly understanding I had either when I started. I think I took for granted how much I knew about wine, because it was my cocoon when I started the show. I definitely, Guy, didn't ever think of myself as a pro. I was 30 years old when I did my first episode. I never thought I would be known or have notoriety. I knew that I was a class clown and had a level of charisma that people were attracted to me, but I never anticipated me popping on video the way I ended up popping a video.

• 31:43Guy Raz?

  Well, to this point about charisma, right? Some people have it naturally. Some people, many people, by the way, I believe, can develop charisma. Charisma can come with things like leadership or responsibility, but some people don't, they just don't have it, or they're, they don't, you know, they're more introverted or shy.

• 32:01Speaker 01

  Which I think leads to podcasting and writing. I have a lot of friends and a lot of people who've sent me incredible emails that are very emotional to me. Because, you know, I am so over the top, but I would argue that so much of the feedback I get are from people that are very different than me. Because they hear me saying what I'm about to say, which is like, look, don't force the medium. If you are incredibly awkward or non-charismatic in your own judgment and the judgment of others, this is not like a self-esteem issue. Well, then don't force trying to like carry a one-hour show on video. You know, I'll be very frank with you, I'm devastated that I'm not a better writer or have that skill set.

• 32:42Speaker 01

  I would love to not have like kind of the on-pressure that audio and video create. And then sometimes just being, sometimes, guy, I'll give you a great example. I'm on flights sometimes where I just have massive ideas. But because of the, you know, I'm on a plane and it's not conducive to putting out a video. I wish I could bang out an incredible 16-sentence manifesto and post it on LinkedIn. It doesn't flow for me that way. My book writing is, you should see what's going on with my latest book, it's hilarious. I audio the whole thing with a ghostwriter and now we're going through it. And I'm literally, it's being read back to me because I'm audio and I'm adjusting to it.

• 33:26Speaker 01

  And then sometimes I'm making edits and then the original time I just said it two lines later. It's like an inefficient process. So just to not be too long-winded, find your medium. If you're not incredibly charismatic, you might have the luxury of being a compelling writer. And that's okay. You don't have to be on video and audio. Writing is still crushing on the internet.

• 33:50Guy Raz?

  But if it sounds to me that, I mean, I think this is sort of self-evident, that if you have ambitions to scale, to create something much bigger than where you are right now. It's hard work. You have to be in all of these places or in some or in many of these.

• 34:07Speaker 01

  Or, or, or, I don't think of it as hard work. I genuinely think of it as fitness. Right? So Seth, uh, who's part of my team right now came in to set up this, I, I, when he walked in, he said, Seth, you look great. He's just like in really good shape. He's always been in great shape, but I know that Seth puts in the work. Of course he has some natural, you know, DNA gifts. I have put in a lot of work over the last seven years. Physically, and I look at my old videos and now I'm like, man, I'm really, I'm really proud, but I'm not Mr. Olympia. Right? And I also am now 45. If I did this at 27, it might've been interesting, but like this 45 year old little gut is never gonna, and, and that's how I think about what we're talking about here. Look, you don't have to go to the Hall of Fame like Kobe

• 34:52Speaker 01

  and be in the gym every minute of your life. Yes, this is not about like, if you dream it, it will come. This is about, look, if you put in reps in the gym, you will start gaining muscle. But don't get to the place in the gym where you start hurting yourself and getting burnt out, or you go so hard in the gym for three months. But then you eat like crap for a month because you, it wasn't sustainable. The way the gym and health and fitness is, that's how I think about business. For me, a lot of effort on work has been very easy. It is my hobby.

• 35:28Guy Raz?

  Yep.

• 35:28Speaker 01

  Business is my golf, is my skiing, is my painting. It's my hobby. I also know for a lot of people it is not, and it's beautiful to have a nine to five business.

• 35:40Guy Raz?

  Sure.

• 35:40Speaker 01

  That, you know, you stay within your means of what that does. But hey, if you go nine to six and you have your same talent, yes, you're gonna be eking out results.

• 35:49Guy Raz?

  So here's my question, and this is a bit of a digression because we're talking about marketing, but, and I, I asked you a version of this in the podcast, but I, I'm really curious. What motivates you? I mean, if it's not, I mean, you're very wealthy. You've made a lot of smart investments. You've sold businesses. You go to garage sales on the weekend looking for bargains. What, you know, I, I mean, I love that, I love that, but, but what, what motivates you? Is it money? Is it, is it?

• 36:14Speaker 01

  It's, it's three, it's three things. Let's break down garage selling. So I'm living life, putting out all this marketing stuff and I'm, I listen for all my talking. So I get a lot of DMs and emails saying, "Cool, Gary, but I can't put $1,000 into Netflix stock. I can't put $5,000 into YouTube ads." I'm like, "Okay, that makes sense. I'm gonna show people what I did when I was 17 to 24 to make some side money. I'm gonna show them how I garage sale. You wanna start with $11? I got something for you. And let me show you how you go from $11 to $4,000 in a summer by going to town sales and getting educated." The other part of that... So that's legacy, guys. To answer your question, three things.

• 36:59Speaker 01

  I want legacy. I'm attracted to legacy. I'm genuinely curious, which is number one for me. When you said, "What drives you?" Curiosity. I'm wildly curious where I sit in my profession. I love sports. Sports has it epic. There's a lot of data that supports a LeBron James versus a Dominique Wilkins conversation. In business, it's a little trickier because what's interesting is my relationship with money. I have a little bit of a different take with entrepreneurship. I think innovation matters. I also think how much you give back to, you know, it's how I'm living my life. How much you give back to entrepreneurship

• 37:41Speaker 01

  is to the game is interesting. But I am curious. How strategic am I? How much can I squeeze out of the gifts I was given? So I think curiosity, legacy, the thrill of the hunt... You know, the best part about garage selling is you pull up to a house at 7:30 in the morning and you don't know if you're gonna find a rare Nintendo game for a dollar. It's fun.

• 38:04Guy Raz?

  You know, I've said this before. I've said it before publicly. I think curiosity is much more important than raw intelligence. I think actually people who are curious, because I think curiosity is a, can be a developed, it's a choice. You could choose to be curious, and it's as simple as that. And it's actually much, much more important than raw intelligence because in my experience, every founder who's been on How I Built This is a person who follows their curiosity. So I think it's a, it's a super important point. I wanna, I wanna ask you about a brand, and you may not, you may not have one off the top of your head, but maybe you do. Which brand right now do you think is, is doing marketing very well right now?

• 38:50Speaker 01

  You know, believe it or not, we work with TikTok, Vayner, but it's not the work we're doing with them that's gonna make me say TikTok. It's gonna be the fact that I think Nick Tran is a very good operator as their CMO. I love what they're doing with their television commercials, using content that, like, it's my favorite concept. It's you're getting affirmation that human beings think this is interesting, and then you're taking it to another platform and giving it even more awareness. So I think TikTok has done a very solid job of, it's really funny, I think TikTok and Facebook, believe it or not, building awareness around groups.

• 39:29Speaker 01

  I'm blown away by how much under thirty-year-olds are signing up for Facebook groups that scale right now. I think it's an effective marketing job by them. Elf Cosmetics, I think, has been very native to TikTok, to a demo that they need to win there. That, those are some things, like, you know, my brain went very fast when you said that.

• 39:49Guy Raz?

  Yeah.

• 39:49Speaker 01

  You know, the truth is, it's always a tough question for me because I'm, because unless I know the business results.

• 39:55Guy Raz?

  Yeah.

• 39:55Speaker 01

  I think that marketing is very good at cheering for itself in a silo without asking if it's doing what it's supposed to be doing. You know, the ad world loves to clap and celebrate itself around work that isn't actually driving business results, which I've always found fascinating.

• 40:14Guy Raz?

  What do you think about sort of, you know, kind of unusual approaches to content marketing? Like, I think of Steakums. You know Steakums?

• 40:20Speaker 01

  Yeah.

• 40:21Guy Raz?

  Steakums has a Twitter account that's gotten a lot of attention because it's just, the person writing the tweets is just really quirky and weighing in on all kinds of things that have nothing to do with Steakums. But it's, but you go to their website, it's actually kind of funny and interesting. And they sell T-shirts and hats and it's, you know, who's, I haven't thought of Steakums since the eighties.

• 40:42Speaker 01

  I'm a, I'm a huge fan of breaking patterns. If you think of, you know, it's funny, I have been willing, as a human being, to take on a little crow, a little judgment, out of my subconscious bias towards breaking patterns.

• 40:57Speaker 01

  I wouldn't call it shock jock, but I think, you know, when I, when I communicate, a lot of times I look at myself, I'm like, it took me a long time. I'm like, oh, this is me being affected by Randy the Macho Man Savage and Eddie Murphy and Chris Rock. Like, I'm affected by that. And when I think about those three, they broke patterns in their craft in delivery. And I think what you're talking about with Steakhouse or what Wendy's does very well, or other brands, Popeyes, is breaking patterns. I mean, it's what we did with Planters, right? We killed Mr. Peanut. That stopped everybody. Guy, before Vayner won the Planters business, when we started doing the work, we realized nobody cared about Mr. Peanut.

• 41:41Speaker 01

  That was a 1960s phenomenon. So how do you break the pattern? You kill him. All of a sudden, miraculously, America really cared about it. And so, yeah, I mean, how do you break patterns? Like, that's what commercials were when they first hit television. What's unusual, that isn't annoying or disruptive? That's what commercials became. So, yeah, I'm a big fan of marketing that is different, catches you quote unquote off guard, but values the other person's time. And that's where I think we've lost our way in marketing. A lot of marketing is disrupting people instead of catching them off guard.

• 42:22Guy Raz?

  The content has to be worthwhile.

• 42:25Speaker 01

  It goes back to that escapism. Like, if, instead of a pre-roll podcast ad, if out of nowhere, guy, you started singing, let's use you. One of the great, one of the great shows.

• 42:36Guy Raz?

  I have sung before.

• 42:37Speaker 01

  But I mean, the ad.

• 42:38Guy Raz?

  Oh, yeah.

• 42:39Speaker 01

  Right? Like, if somebody, if I came to you and said, guy, I really want wine text to explode, and I think your audience, so would you sing?

• 42:47Guy Raz?

  Yeah.

• 42:47Speaker 01

  I don't want to do a live read. I don't want to do a pre-roll. I don't want to do a mid-roll. I want to pay you that in the middle of an interview, out of nowhere, for no reason, you start going wine text dot com. You know, like, like, that would completely stop your entire audience. That's how my brain thinks. I think in creative ways that will completely get everybody to quote unquote pay attention, but not. Be something that is bothering them because they want to actually hear the rest of it. There's a level of surprise, delight, integration. It's why I fell in love with social media. It was in the feed. It wasn't like you just got, "I'm watching a show and it gets to the cliffhanger and that crap. Now I gotta

• 43:29Speaker 01

  watch a Spindrift ad. Big shout out to Spindrift. I'm drinking one right now." It's more integrated in a different silly way. You singing a wine text ad will make people chuckle more so than when you start reading it, "Hey, let's stop real quick this. I gotta give a shout out to one of our sponsors." It's already dead because it's intrusive instead of in addition to.

• 43:52Guy Raz?

  Gary, I am going to explore that. And I hope our audience watching right now will forgive me if I break out in song in the middle of your podcast episode, just in the middle of it randomly.

• 44:01Speaker 01

  I love it. I'm in.

• 44:04Guy Raz?

  That's Gary Vaynerchuk. We talked back in May as part of the How I Built This 2021 virtual summit. More conversations like this one from the How I Built This summit will be in your feed soon, including my live interviews with Brene Brown, Adam Grant, and Rashad Robinson. You will not want to miss those. So please keep an eye on your podcast feed. This episode was edited by Casey Herman with music composed by Rameen Arablouei. Our production staff for the summit includes Neva Grant, J.C. Howard, Julia Carney, Farah Safari, Liz Metzger, Janet O'Jung Lee, Annalise Ober, Gianna Capadona, John Isabella, Ali Prescott, Joanna Palowska, and Jessica Goldstein. Our intern is Harrison

• 44:46Guy Raz?

  Vijay Choi. Jeff Rogers is our executive producer. I'm Guy Raz, and you've been listening to How I Built This from NPR.