The Habits of Winning Entrepreneurs / Why You Should Give Away More For Free | 2018

17 Aug 2025 · 10 min

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Podcast Notes: The GaryVee Audio Experience - The Habits of Winning Entrepreneurs / Why You Should Give Away More For Free (2018)

Episode Overview

  • Host: Gary Vaynerchuk (GaryVee)
  • Guest: Hip Hop artist Racks
  • Focus: The significance of giving away valuable content for free as a strategic business move and the habits of successful entrepreneurs.
  • Key Theme: Free offerings as a pathway to greater exposure and audience growth.

Key Concepts and Ideas

Gary's Background and Entrepreneurial Mindset

  • Unconventional Youth: Gary reflects on his childhood, highlighting his unique interests over social norms (i.e., selling Shaquille O'Neal figures instead of dating).
  • Winners vs. Non-Winners: He associates early morning efforts with a winning mentality, emphasizing the importance of hustle and hard work over traditional accolades.

The Power of Free

  • Giving Away Value: Gary argues that offering valuable content for free is a gateway to reaching a larger audience.
  • It creates exposure without financial barriers.
  • Successful entrepreneurs often prioritize impact over immediate monetary gain.
  • Psychological Perspective:
  • Charging for content can create a barrier and lead to skepticism among potential customers.
  • People are more likely to engage when there's no financial commitment.

Business Strategy Insights

  • Long-Term Gains vs. Short-Term Profit:
  • Providing free content can lead to a larger and more loyal following, which outweighs the short-term financial benefits of charging for content.
  • Example: Gary mentions that more people will be willing to engage with your content if there’s no cost involved, which can ultimately lead to greater financial success.

Importance of Content Formats

  • Diverse Content Delivery: Gary emphasizes the necessity to reach audiences through multiple channels (audio, video, social media).
  • He discusses how having a large team dedicated to content creation allows him to deliver information in various formats.
  • Adaptation to Changes: He stresses the importance of not being reliant on a single platform for audience engagement, as trends in social media fluctuate.

Discussions with Racks

  • Desire to Impact: Racks expresses a strong desire to make a difference, indicating that he values creating a broader impact over direct financial gain.
  • Navigating Monetization: The conversation shifts to the challenges of monetizing content and how Racks can still achieve his goals without charging directly.

Key Takeaways

  • Mindset of Giving: The mentality of giving away your best content for free can lead to personal and professional success.
  • Focus on Creation: Successful entrepreneurs focus on creating content that resonates with their audience rather than limiting access through payment.
  • Audience Engagement: To truly engage with your audience, it’s essential to provide your content in accessible formats and remove any financial barriers.

Conclusion

  • The episode encapsulates the philosophy that in business, true success is achieved through generosity and a focus on impact, rather than immediate financial gain. Gary Vaynerchuk’s insights encourage entrepreneurs to rethink traditional models of monetization and consider how giving away valuable content can serve as a powerful business strategy.

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Transcript

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0:00If you understood how off the fucking reservation I was as a kid. like I'm like a normal guy so I had friends and everything but I was so different like to the extreme like pretty girls liked me in high school and I didn't want to talk to them because I wanted to go to Kmart and buy Shaquille O 'Neal figures to sell on the flea market on Saturday. Like you know so my big thing on that is on that is like who gives a fuck what people's opinions are. It's so funny. I'm a winner, and when I drive to the airport at like 5.30 in the morning, and I'm like, and I look outside, I see a line, I'm like, winners.

0:43I swear on my fucking children. That's what goes right through my head. I look, I'm like, winners. Right? Like, remember, what year did you, AJ, start college, 05? Yeah, 05. Before yourgrills.com, do you remember remember we had a site called thebathingape.com? Yeah. Remember that? Didn't you and AJ come down to the first BAPE store in Soho when it opened? That's where it opened first, I remembered it when it opened. Yeah, I'm with you. Yeah, so, but because at the end of the day, like you said, winners, those same kids that are getting up at five o 'clock in the morning. I want to hire all of them.

1:18Yeah, that's what I'm saying. Those are the only ones I want to talk to. Like, if you got an A in science, like, I don't want to talk to you. I don't care about that shit. But if you woke up at 6, 15 in the morning and you figured out how to pay off the guy at the fucking front? There's a number one guy in the whole field. Let me ask you a question. What do you want to happen? I want to... No, no, I'm talking macro for you selfishly, not selflessly. Selfishly? Yeah, selfishly. I want to impact as many people as I possibly can and basically be like, that guy Rex was deep dictated law. Don't sell it then.

1:51You don't think? Not when you just told me that's what you want. I mean, but I'm also looking at... Uh-huh. So let's keep playing. Okay. That's why I got excited. Yeah, but I'm also looking at it from the standpoint of impact is more important to me than having the monetary value. So don't sell it. But how will I get it out then? If it's free, more people are going to come. Okay, that makes sense. That makes sense. Because I can get an investment from, okay, I see where you're going with that. I know where I'm going. I see where you're going with that, okay. Let's play, right? Yep. Like, I understand, but what I need to know is what you want to happen, right?

2:26So the thing that's interesting about you and why I stood up and got excited and just did my little thing is because I think we have a lot of similarities. I already knew and I knew a little something, but I can smell. The reason I mean is I need to touch. The reason I do what I do is I have to touch shit. The reason I was bad at school, like I have to touch it. This whole company, you know, like sucks. Like I built a$200 million company, but I had to do it and do all the shit that comes along with it because I got to touch shit. Right. You have the ability to make money. That's the point of the course itself.

2:59Correct. That means you're dangerous when it comes to content. See, the thing that's dangerous about me compared to all the other motivational, inspiring people is I don't want your money. Because I know how to make money elsewhere. Yeah, yeah. Which means it's the reason I'm impacting the most people. Makes sense. Because money does two things for the course. One, it's a financial barrier. The people we're talking about, there's a lot of people that 250 is real money. Number one. Especially if the attraction is, this is a game that's great to start that process. This is not for millionaires. It's not for my employees.

3:42No, it is, but you know what I mean. Especially because you have a great point there, which is time arbitrage. This is a great game. One thing I was always bad at, and I'm still bad at it, and it turned it into my strength, is I don't manage my time well. Which weirdly worked out for me in the end because I still continue to give love when I shouldn't be.

4:06But what's really interesting to me about you is money does two things. One, it's a restriction twice. One, it's money, and that's a percentage of people. Especially with your flavor, it's going to be a restriction to a good percentage of your audience. Okay. Right? Number two, for the rest of them that can afford it, for more than half of them, it puts you in a box.

4:32The box where you're full of shit, I don't believe you, you're just doing this because you want my 250. And that just leaves you with 20 % of the 100 % that you're trying to reach. Right. The end. Mm-hmm.

4:49So in terms of, so then. And you know what's been so fun? I was a whiz kid my whole life, right? Right. $3 ,000 selling baseball cards when I was 12. Went into my daddy's liquor store and fucking blew it up. I'm, you know, I'm starting to make that transition where I get to be like the old guy, right? Right. It's fucking rewarding as fuck. You know, because like that moment, that double smile for me, it's the best. Because I know I'm right. And I know you know I'm right. Right. Now, if you now backtrack and say, listen, Gary, cool, but like honestly, on a real kick, of course I want to inspire, but I feel great about selling for$250 ,000 because what I'm doing is, that's a deal.

5:22It's worth$5 ,000. You can tell me anything. Nothing makes me upset, nothing. People can tell me anything, really. I don't think, who the fuck am I to judge anybody about anything? I mean that for real. It's why I like everybody, because I don't like anybody, and I love everybody. It's the same shit. My opinion doesn't matter. Like kind of, you know what I mean? It's just humility. Like who am I to judge? But this is why in these, like this is what we really need to think about. So let me explain. If, you know, what the other part that comes along with the advice I'm giving you is a totally different upside.

5:57$250 a head, even if it becomes 2 ,000 a head because everybody's winning and you know, you can rate, right? Times 10 ,000 people, still 100 ,000, real money, wealth, mansions, life, right? Still fall short if you're good enough, if you give it all away for free because then where your life ends up when you're 52 is you actually own Supreme or Puma. Okay. Because you build the biggest audience. Right. I mean, that's kind of what's happening right now. Right. At the end of the day, people come up to me, they think that I work for those people. They think that I work for these. And it's just based off of my association and how hard I work.

6:41Work with who? like Supreme, uh, Bape, any of the streetwear brands that basically have, they think they're feeding you. Basically. Yeah. It's me feeding myself because I'm just that dedicated to what I do. I couldn't agree more. Yeah. I would, I never even crossed my mind that you were with them like that. You can win if you're the best at what you do. Right. And I think that at the end of the day, I'm one of, if not the best at what I do. I'm definitely the most notable of all the people that do what I do. And so here's what I would say. everyday people tell me why the fuck do you tell everybody the best shit for free and I'm like because 99 % of people aren't going to do anything about it and there's an abundance one of the reasons psychologically it would make sense for you to charge is you know you're also creating a supply and demand issue that takes away your own advantage I kind of want to move up right I'm telling you the move up is to get as many people on as possible and create no friction.

7:43There's always going to be something else. I'm about to make K-Swiss hard to get. Oh no, that's literally what I just said about the coat. It's always going to be something. Literally, yes. I agree with that. The end. Yeah. The end. Got it? That's it. The secret is the reverse of what people think. It's some Bible shit. They were right. Just give it all away for free. Get it all back. Yeah, nah. So you think I should go, you think I should focus more? I think the biggest mistake that smart people are making right now is charging their audience. Okay, so. And that's what's coming to everybody, naturally.

8:21I don't think, you know, I think it's, because it's like music. The music should be free. That's how you make real money. I would fucking, I'm fucking yelling on people online. I'll yell, bit torrent my book if you can't afford it.

8:39I'm not for the facts. Yo. No, I don't. Like I'm happy that some kid just heard me say that and you're gonna keep it in the edit and like I want them to hear that because what? I want him to win. I want her to win. Do I lose money because I just said that? Yep. Or there's some people that don't even know what that is and they just Googled it and they're like oh shit. Like yes, but like I mean it. Right, because you want people to have that information. I didn't write the book because I'm gonna make the fucking bullshit$4 per book or whatever the fuck is my cut with the publisher. I wrote it because some people learn better reading a book than watching my fucking videos.

9:13I fucking hated recording my audio book. I didn't record it for the fucking couple more sales. I recorded it because some people don't want to read a fucking bullshit book, but they'll audio the fuck out of me in two fucking gym sessions and walk in their fucking dog. The content is the magic. It's the gateway drug. I get 150 ,000 racks a talk because I gave away my shit for free while fuckers are trying to sell$400 e-books out there. See, that's what I'm on. Okay, well then you better fucking listen. I'm listening all ears. You got it? Yep. How they want it, in every format. I'm taking on all the costs.

9:48How many people we got? 20. I got 20 people on my team helping me make content. Why? Because I'm going to give it to you in every fucking format. Audio, vlog, vlog on YouTube, vlog on Facebook, Podcast, Google, Apple, Samsung. Instagram, cool. Snapchat, good. LinkedIn, yep. Medium, good. My blog, yep. Twitter, yes. One interesting thing about that. What's everybody else doing? They get a little bit of a fan base on Instagram. They're like, good, I'm good here. I'm good here. Okay. That's it, that's fine. What are you going to do when Instagram's not relevant?

From the publisher

This is one of the top 10 throwback episodes, originally from 2018.This section out of a business meeting I had with Hip Hop artist Racks really shows the value you get in return for giving away your best shit for free - pure exposure. I dive into why free is the gateway to reaching an even broader audience & why it makes up the habits of true winning entrepreneurs. 

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