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

Summary

Podcast Summary: The Habits of Winning Entrepreneurs / Why You Should Give Away More For Free | The GaryVee Audio Experience

Host: Gary Vaynerchuk
Guest(s): Unnamed guest, collaborative conversation
Release Date: August 17, 2025

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Episode Overview

In this direct, high-energy episode, Gary Vaynerchuk breaks down the traits that set winning entrepreneurs apart, focusing on relentless hustle, unorthodox thinking, and the radical idea that giving away your best advice for free is the real key to long-term impact and wealth. The conversation dives deep into mindset, business growth, personal branding, and why putting audience over immediate profit creates disproportionate returns. The mood is raw and unfiltered, with Gary dispensing actionable advice rooted in his own success story.

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Key Discussion Points & Insights

1. Entrepreneurs Are Built Different

• Gary shares anecdotes about his childhood, illustrating an obsessive entrepreneurial drive from an early age, including preferring business ventures over traditional teenage pursuits.

  • [00:00] “If you understood how off the fucking reservation I was as a kid... I wanted to go to Kmart and buy Shaquille O'Neal figures to sell at the flea market.”
  • The importance of not caring about others’ opinions as an entrepreneur.

• He highlights that real winners have an obsessive work ethic and unconventional focus—a willingness to sacrifice what’s easy in favor of chasing opportunity.

  “My big thing on that is … who gives a fuck what people's opinions are?... I'm a winner.” (Gary, 00:32)

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2. Winners Get Up Early (and Why That Matters)

• The value Gary places on discipline, noting that those up early (metaphorically and literally) are the types of people he wants to hire or work with.

  • [00:46] “I look, I'm like, winners, right?... those same kids that are getting up at 5 o'clock in the morning, I want to hire all of them.”

• Grades and formal education are discounted in favor of initiative, creativity, and real-world experience.

  • “If you got an A in science, like, I don't want to talk to you ... But if you woke up at 6:15 in the morning and you figured out how to pay off the guy at the front, that's the number one guy in the whole field.” (Gary, 01:21)

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3. Focusing on Impact > Money

• Gary pushes the guest—and listeners—to clarify whether their motivation is truly impact or monetary gain.

  • [01:37] “What do you want to happen? Macro, selfishly, not selflessly.”

• For those driven by impact, Gary advises maximizing reach by removing financial barriers.

  • “If it's free, more people are gonna come.” (Gary, 02:08)

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4. The “Give It Away For Free” Philosophy

• Gary lays out a fundamental law of his approach: Give away your best content for free and trust that the audience (and greater rewards) will follow.

  • “That's why I got excited ... I have to touch shit. The reason I was bad at school, like, I have to do. I have to touch it.” (Gary, 02:21)

• Charging up front puts up unnecessary barriers and boxes you in—especially if your true goal is scale and legacy.

  “The thing that's dangerous about me compared to all the other motivational, inspiring people is I don't want your money... Which means it's the reason I'm impacting the most people.” (Gary, 03:00–03:13)

• Money creates two big downsides for information products:

  1. Restricts access to those who can't afford.
  2. Makes the audience question your motives.

  “Money does two things for the course. One, it's a financial barrier ... Number two, for the rest of them, that can afford it ... it puts you in a box ... you're just doing this because you want my 250.” (Gary, 03:21–04:20)

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5. Long-Term Upside: Legacy over Short-Term Gains

• Gary illustrates with his own life: building an enormous audience by over-delivering for free leads to compounding advantages, bigger than simply making a few thousand per head.

  “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. Because you build the biggest audience, right?” (Gary, 06:05–06:31)

• Reputation and scale become the true assets, paving the way for business opportunities and authenticity with your audience.

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6. Abundance Mindset: There’s Always More

• Gary rebuffs scarcity tactics in personal branding (e.g., artificial supply and demand), emphasizing that greatness makes you indispensable and sought-after.

  “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.” (Gary, 07:56)

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7. Notable Quotes on Giving Value

• “Every day 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 gonna do anything about it. And there's an abundance.” (Gary, 07:09)

• “Music should be free. That's how you make real money ... I'm fucking yelling on people online. BitTorrent my book if you can't afford it, yo.” (Gary, 08:18–08:40)

• “I didn't write the book because I'm gonna make the fucking bullshit $4 per book. I wrote it because some people learn better reading a book than watching my fucking videos.” (Gary, 09:02)

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8. Omni-Channel Content Mindset

• Gary shares that true impact and audience-building now require being everywhere, not just on one platform:

  • “How many people we got? 20. I got 20 people on my team helping me make content. Why? Cause I'm gonna give it to you in every fucking format.” (Gary, 09:45)

• He emphasizes that many stop at one platform (like Instagram) and lose out when trends shift.

  “What's everybody else doing? They get a little bit of a fan base on Instagram ... what are you gonna do when Instagram's not relevant?” (Gary, thread 09:45+)

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Notable Moments (with Timestamps)

• [00:00–01:21] – Gary’s origin stories & philosophy on being an outlier.
• [01:35–02:17] – The impact vs. money crossroads.
• [03:00–04:20] – The two big problems with monetizing education up front.
• [06:05–06:31] – How giving value leads to legacy and real wealth.
• [07:56] – The “secret” to entrepreneurial win: “Give it all away for free. Get it all back.”
• [09:45+] – Multi-platform presence and relentless content production.

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Final Takeaways

• Give more than you ask: The greatest leverage today is providing real value for free—impact and audience are the new currency.
• Don’t gatekeep: Money creates unnecessary obstacles and erodes trust, especially when your goal is impact.
• Be Everywhere: The modern entrepreneur must diversify content across platforms to remain relevant and accessible.
• Abundance Always Wins: There are unlimited opportunities if you focus on value and service, not restriction and scarcity.
• Authenticity Rules: Gary’s unapologetic delivery underlines every lesson: be real, be generous, and outwork everyone.

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Memorable Quote for Entrepreneurs

“The biggest mistake smart people are making right now is charging their audience ... The secret is the reverse of what people think. Just give it all away for free. Get it all back.”
— Gary Vaynerchuk ([07:54–07:56])

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For Listeners

This episode delivers straight fire on why generosity and hustle have never been more critical—or rewarding—for entrepreneurs. Gary’s seasoned, practical advice challenges conventional thinking about money and value while providing a tactical blueprint for anyone looking to build authentic influence and lasting success.

Transcript

[A]

If 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. I didn't. Pretty girls liked me in high school and I didn't want to talk to them. Cause I wanted to go to Kmart and buy Shaquille o' Neal figures to sell on the flea market on Saturday, 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 like. And I look outside and see a line, I'm like, winners. I swear, my fucking children, that's what goes right through my head.

[B]

Early risers.

[A]

I look, I'm like, winners, right? Like remember, Remember. What year did you AJ start college? 05. Yeah, 05 before your grills dot com. Yeah. Do you remember we had a site called bapethebathingape dot com? Yeah, remember that? Didn't you and AJ come down the first bape store in Soho when it opened. That's where it opened first. I remembered it when it opened. Like, yeah, I'm with you.

[B]

Like, yeah, so but because at the end of the day, like you said, winners, those same kids that are getting up at 5 o' clock in the.

[A]

Morning, I want to hire all of them.

[B]

Yeah, that's what I'm saying. So like those are the only ones.

[A]

I want to talk to. Like, like if you got an A in like science, like I don't want.

[B]

To talk to you, I don't care about that shit.

[A]

But if you like Woke up at 6:15 in the morning and you figured out how to pay off the guy at the fucking front, there's the number one guy in the whole field. Let me ask you a question.

[B]

Go ahead.

[A]

What do you want to happen?

[B]

I want to.

[A]

No, no, I'm talking macro for you. Selfishly, not selflessly.

[B]

Selfishly, I want to.

[A]

Yeah, selfishly.

[B]

I want to impact as many people as I possibly can and basically be like that guy Rex was. He dictated law on research.

[A]

Don't sell you.

[B]

Don't think.

[A]

Not when you just told me that's what you want.

[B]

I mean, but I'm also looking at, uh huh.

[A]

So let's keep playing.

[B]

Okay.

[A]

That's why I got excited.

[B]

Yeah. But I'm also looking at it from the standpoint of impact is more important to me than like having the monetary value.

[A]

So don't sell it.

[B]

But how I get it out then.

[A]

If it's free, more people are gonna come.

[B]

Okay, that makes sense. Makes sense. Because I can get investment from. Okay, I see where you going with that.

[A]

I know where I'm going.

[B]

I see where you going with that.

[A]

Okay, let's play. Right?

[B]

Yeah.

[A]

Like, I understand, but what I need to know is what you want to happen, right? So the thing that's interesting about you and why I stood up and got excited and just did my little thing is. Cause I think we have a lot of similarities. I already knew and I knew a little something, but I can smell the reason I meet 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 do. 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. Cause I gotta touch shit.

[B]

Right?

[A]

You have the ability to make money. That's the point of the course in itself.

[B]

Correct.

[A]

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. Cause I know how to make money elsewhere.

[B]

Yeah.

[A]

Yeah. Which means it's the reason I'm impacting the most people.

[B]

Makes sense.

[A]

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, like, you know, if the attraction is, you know, this is a game that's great to, like, start that process. This is not for millionaires, you know, like, it's not for my employees. No, it is, but you know what I mean, right? Especially. Cause, like, you have a great point there, which is time arbitrage. Right? 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. But what's really interesting to me about you is money does two things. 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 gonna be a restriction to a good percentage of your audience. Right. Number two, for the rest of them, that can Afford it for more than half of them. It puts you in a box. The box. Well, 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 the end.

[B]

So in terms of.

[A]

And you know what's been so fun? I was a whiz kid my whole life, right? $3,000 selling baseball cards when I was 12. Went into my daddy's liquor store and fucking blew it up. I'm starting to make that transition where I get to be like the old guy, right?

[B]

Right.

[A]

It's fucking rewarding as fuck. Because that moment, that double smile, for me, it's the best. Cause 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 wanna inspire. But I feel great about selling for 250. Cause what I'm doing is that's a deal. It'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. That's why I like everybody. Cuz 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 the other part that comes along with the advice I'm giving you is a totally different upside. $250 ahead. Even if it becomes 2000 ahead 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.

[B]

Okay?

[A]

Because you build the biggest audience, right?

[B]

I mean, that's kind of what's happening right now. Like, right? Like 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. Like I don't. And it's just based off of my association and how hard work with whom. Like Supreme Bape, any of these streetwear.

[A]

Brands that Basically have they think they're feeding you. Basically, yeah.

[B]

It's me feeding myself because I'm just that dedicated to what I do.

[A]

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?

[B]

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.

[A]

Of the people that do what I do. So here's what I would say. Every day 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 gonna 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.

[B]

I kinda wanna move up, right?

[A]

I'm telling you, the move up is to get as many people on as possible and create no friction. There's always gonna be something else. I'm about to make K Swiss hard to get.

[B]

Oh, no. That's literally what I just said about the coat. It's always gonna be something. That's literally. Yes, I agree with that.

[A]

The end.

[B]

Yeah. Me with events.

[A]

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.

[B]

Yeah. Nah. So you think I should go? You think I should focus more?

[A]

I think the biggest mistake that smart people are making right now is charging their audience.

[B]

Okay, so.

[A]

And that's what's coming to everybody naturally. I 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. BitTorrent my book if you can't afford it, yo.

[B]

Nah.

[A]

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. Are there some people that don't even know what that is and they just googled it and like. Oh, shit. Like. Like, yes. But, like, I mean it, right?

[B]

Because you want people to have that information.

[A]

I didn't write the book because I'm gonna make the fucking bullshit $4 per book or wherever fuck is my cut with the publisher. I wrote it because some people learn better reading a book than watching my fucking videos. I fucking hated recording my audiobook. I didn't record it for the fucking couple more sales I recorded 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.

[B]

Ride home from work.

[A]

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 ebooks out there.

[B]

See, that's what I'm on.

[A]

Okay, well, then you better fucking listen.

[B]

I'm listening. All ears.

[A]

You got it?

[B]

Yep.

[A]

How? They want it in every format. I'm taking on all the costs. How many people we got? 20. I got 20 people on my team helping me make content. Why? Cause I'm gonna 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. 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 gonna do when Instagram's not relevant?