10 Ways to Have a Winner's Mindset

15 Aug 2025 · 18 min

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The GaryVee Audio Experience: Episode Summary

Episode Title

10 Ways to Have a Winner's Mindset Description In this episode, Gary Vaynerchuk discusses ten of his ideologies aimed at helping listeners become the best versions of themselves. Originally aired in 2019, this throwback episode emphasizes practical advice for personal and professional growth.

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Key Concepts

Introduction

  • Mindset Shift: Gary emphasizes the importance of changing one’s perspective on life and work, particularly on Monday mornings.
  1. Reframe Your Week
  2. Mindset on Mondays: Instead of dreading Mondays, view them as opportunities for new beginnings.
  3. The Internet Advantage: The digital age offers unprecedented opportunities to build businesses and pursue passions.
  1. Chase Happiness
  2. Passion vs. Financial Success: Prioritize what makes you happy, even if it doesn’t lead to wealth. Success is subjective.
  3. Self-Awareness: Acknowledge that your path to happiness may differ from societal expectations.
  1. Stay in Your Lane
  2. Understanding Strengths: Focus on what you are good at and avoid the pressure to fix weaknesses.
  3. Personal Example: Gary shares his journey from being labeled a “loser” to achieving success by focusing on his strengths.
  1. Take Action
  2. Overcoming Fear of Failure: Everyone experiences failure; the key is to learn and move forward.
  3. Optimism and Resilience: Embrace challenges and maintain a positive outlook.
  1. Play Long Term
  2. Invest in the Future: Short-term thinking leads to missed opportunities. Focus on long-term growth.
  3. Market Dynamics: Recognize that while most are short-sighted, those who think long-term will ultimately prevail.
  1. Figure Yourself Out
  2. Self-Discovery: Understand your desires and aspirations without the influence of societal pressures.
  3. The Importance of Authenticity: Be true to yourself rather than imitating others.
  1. Take Action
  2. Motivation vs. Action: Many seek motivation but fail to act on it. The real growth comes from doing.
  3. Tangible Steps: Gary encourages listeners to implement what they learn rather than remain passive.
  1. Find Optimism
  2. Optimism as a Trait: Recognize that optimism is not universal. Work on cultivating a positive mindset.
  3. Sharing Optimism: Gary aims to spread his optimistic outlook to inspire others.
  1. Stay Driven
  2. Value of Human Existence: Appreciate the rarity of being human and the potential to create.
  3. Avoiding Complacency: Challenge yourself instead of settling for mediocrity.
  1. Live Your Life
  2. Regret Management: Avoid living with regrets by seizing opportunities.
  3. Fulfillment: Strive for happiness in all aspects of life, which will reflect positively in business.

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Conclusion Gary concludes with a powerful message emphasizing that how you make money is more important than how much you make. He encourages listeners to take charge of their lives, challenge their mindsets, and pursue their passions to achieve both happiness and success.

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Key Takeaways

  • Mindset Matters: Your perspective can greatly impact your success and happiness.
  • Self-Awareness: Understanding your strengths and passions is crucial for personal and professional satisfaction.
  • Action-Oriented: Motivation is meaningless without action; implement what you learn immediately.
  • Embrace Optimism: A positive mindset can serve as a powerful tool in overcoming challenges.

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This episode serves as a motivational call to action, encouraging listeners to reflect on their lives, pursue their true passions, and adopt a winning mindset.

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Transcript

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0:00This is the Gary V Audio Experience. It breaks my heart. My friends live for Friday night. They know they get the week. Monday morning's the worst. It's just a huge percentage of one's life. I can't wrap my head around with the internet. This is not your grandpappy's life. We have the internet. You can make shit happen. You can build businesses or side hustles. I just don't understand why people relegate into losing mentality and just thinking they can't. You can't because you want to be on the bowling team or softball or play video games. That's why you can't. There's plenty of time. Get shit done.

0:35The level of complaining is unacceptable. Look, what if I told you this was the last Monday morning of your life? What if I told you you'd die this week? Would you complain about your crap job or that test you don't want to take? I doubt it. You would go much higher level thinking. Well, that's really what it takes. It takes understanding that if you're not pumped right now, if you're begrudging what you're about to do, if you're not looking forward, please recognize the world we're living in. We're living in a world where there's so much more opportunity. This internet thing created way more opportunity for all of us.

1:09Way more. I mean look, you might not even be alive. Like your mom and dad could have had sex like three minutes later and you wouldn't even exist. And you're complaining. You could have ended up being a bus, a tree. I just don't get the mentality of being head down sad on a Monday morning. I'm going to make Monday morning my bitch. I'm going to make you Saturday Monday morning. That's what I want to do every morning. And that's what I want from you. Please take a step back and think about how awesome it actually is. And then recognize that you can attack the world in a totally different way because you were lucky enough to be born during this era.

1:46Number two, chase happiness. If you're not great at it, but you love it more than life, should you go after it? To me, the answer is yes. The problem is, please also recognize you're probably not gonna get rich. Like, if you love basketball more than life, it's just what you always loved, you might just make$49 ,000 a year being a basketball coach and having a lot of time on your hand to play basketball. It's just, you gotta understand, you can't have everything all the time always. It's just life. I think happiness trumps everything. easy for me to say because it really worked out for me because happiness coincides with financial upside I have friends who make $74 ,000 a year that are just happier people than friends that are making $18 million a year that are not you've got to do you but please don't let the entrepreneurial society, don't let me, don't let your parents push you into what success is, it's different for all of us but and this is the big but you've got to be self-aware about it number three stay in your lane i just stay in my lane like this is back to self-awareness i stay in my lane i'm a salesman i'm a business builder i've done it my whole life i was an f student at 13 and 14 my friend's parents told my friends not to hang out with me because i was a loser i'm more successful than my entire graduating class combined like like this is because the market doesn't understand that people don't get it you have to double down on your strengths and you have to punt your weaknesses.

3:28In America, there's billions of dollars made on selling you how to fix the things that you're not good at. It's a huge mistake. You need to figure out who you are and go all in. That's what I did. And so when you talk about business or marketing, when you talk about the New York Jets, and when you talk about wine, I've got nothing but bravado. Everything else, you should see me sitting around dinner tables right now talking about politics. The level of humility and the level of listening, you wouldn't expect from me because that's not how you're used to consuming me. I'm loud and proud because I only stay in my lane.

3:59Pay very close attention. I've got nine years of content on the internet now, maybe a little bit more. I've stayed very, very, very narrow. For me, it's lucky.

4:15The reason I've been able to kind of grow is my narrow thing is consumer behavior, which I can deploy against anything. So my narrow thing happens to be quite wide, which allows me to play, It allows me to be a good investor. It allows me to run businesses. It allows me to be a personal... It allows me to do things. But I don't revert from that. Number four. Go do shit. And it was you regularly say that failure propelled you. Are there any instances in your past truly where you couldn't get over it and why? Nope.

4:49I mean, but, but, but, but, but, by the way, by the way, that's the same answer for everybody in this room. That's what humans are good at. We all fail. We've all failed. Like, there are, I, my parents haven't been killed. My child, I mean, there's people that have their children die. Like, could you imagine? Like, the shit idea, like, I'm, like, listen, unfortunately or fortunately, depends on how one wants to look at it, I'm a pretty optimistic guy. I lost three of my four grandparents before I was really, before I knew them. two before I was born and one very early on. So, you know, it's easy for me to be happy.

5:27I have my shit in the right order. The health and well-being of my family. And there's nothing even remotely close to that. Not even remotely. People have gotten through much worse. This is why I'm trying to recall our grandparents and our great-grandparents. People were persecuted and killed. Like, I just, we do not have real headaches. Yikes. You know, I don't know why I have this highly emotional and then completely unemotional part of me, but I mix them together to create the balance and that's what works for me. So, of course there's nothing that I couldn't get up from. Like every other human ever besides somebody who now lives in some weird cave that we don't know about.

6:09You know what I mean? We are strong as. We're really strong. We're just being sold that we're not because there's a lot of money, a lot of money in telling us that we're not pretty enough, thin enough, smart enough, good enough. Fuck that. I want to tell you, you're the best. Go do shit. Number five, play long term. We're going to make less money this year at 100 million than we made last year at 67. Net. I don't mean percentage. Net. Meaning, they're in trouble. Them. I see it. Which means I overinvested. More people. More capabilities. Because I'm going to take the whole pie. So, you know what I mean?

6:58I'm not worried about how much cash I'm going to take home in 2016. Because I can take a lot more in 2020 than I, you know. It's much more fun to take home 44 million in 2020 than 3 million in 2017, 18, and 19. Instead of 4 million in 2018. like people are, 99 % of the market is short term. And the 1 % that isn't and has the talent wins every time. Which makes no sense because unless you're gonna die, you should only play long term. There was a stat that some dude in Mexico City said, one of these like futurist type of characters, I'm sure he's smart, I have no idea who, so I just, but he was right before me as I was mic'd up and he says, it's been scientifically proven, so I don't know if it has or not because I've learned to take that with a grain of salt, but that 85 % of what humans make decisions about is irrational.

7:50And that spoke to me. Because A, I think it's higher. And B, it's why I think all my success is happening. I am stunningly the most rational and the most practical of all. Yet I don't seem it. And when he said it, I'm like, right, that's why. Because the rest of the market is irrational. Number six, figure yourself out.

8:41is, right? Maybe I'm your flavor of the month right now. Maybe your consistent flavor of the life is your mom's point of view, is your older brother who's guided you with good wisdom but wants you to be a lawyer. But you don't want to be a lawyer. You want to be a street artist. You want to take the chance of being an entrepreneur or the reverse or the reverse. Nobody preaches and loves entrepreneurship more than me but I think you see me all the time talking about self-awareness. Are you one? This is the golden era for entrepreneurship. People ask me for selfies. This will go away. It may not go away from me, but it's going to go away.

9:15Like, you know, it's entrepreneurship, like a rap artist, like a baseball player, like the heavyweight. Nobody cares who the heavyweight champion of the world is right now. Nobody cares who's an active astronaut, but they surely did in 1969 and 19, you know, 54 for the heavyweight champ or, you know, they, they change, they change and it will always change and it will continuously change. And right now, entrepreneurship is in this pedestal. It's having its moment. And what I'm fearful of is that you watch my videos, you see my Instagram quotes. And what I want to clarify for everybody is, I hope you understand, I am not giving advice to everybody.

9:56The only advice I'd like to give to everybody is to do you, to find what your North Star is, to understand yourself, to understand what your work-life balance ambitions are, what your financial ambitions are, what your life challenges are, the problems that you want to try to solve and cure as we all do as humans trying to climb those different mountains in our lives. What makes you tick? That is all that matters. Don't do, you know, I don't do Daily Vee or all these videos for you to be like me. I don't think anybody should be like me. Boy, are there enormous amounts of pressures and sacrifices that I recognize are just not healthy or valuable to anybody else but it's also not healthy or valuable to me to do some of the things that you want me to do.

10:39Like it's not fun for me to work nine to five. Like I will break. I will be as equally devastated as you would be to work till midnight every day. And so we just need a call to action for everybody to recognize we have to stop judging everybody else. I'm not judging you. I'm creating content for you to use as a barometer to try to figure out what you like and what you don't like. And I'm trying to provide value through my words, my actions, and my content to bring to people to amplify their worlds. And that's really it. That's the clarification. Like, I don't want people to be like me. I don't want people to do me.

11:19I want people to do themselves. And they just have to start with understanding themselves and not trying to be like me in this moment or that person in the next moment or that person in the next moment. The people that most win are in tune with themselves and figure themselves out. Number seven, take action. There's a reason that guys and gals like me continue to have audiences because people want to be motivated to go and do things or they want to learn tactics to go and do things. but whether I'm giving you tactical advice like filters on Snapchat or Facebook ads or Instagram story collaborations or I'm motivating you through my words because I communicate that way or through my actions seeing this wake up at five if everybody who's watching this actually did something about it and then went on the course of their version of it then they wouldn't be watching this and I genuinely know at the bottom of my heart out of all the people that want to build audiences that I'm the complete opposite of almost all of them because 99 % of people that produce content like this that are out there like I am the business of being that is what they are.

12:36I have businesses. I have Wine Library and VaynerMedia. I don't need your 14 bucks for my book or to be in my course or this and that. So I don't need to monetize you. So I then genuinely want you to never watch me again. The problem is every time you guys are posting, do you know how many times I see on my Instagram, oh, I needed this today? And do you know how many times I see that person nine months later still hanging around? If you needed it, then take it and do something about it. The reason there's gonna be a billion motivational views today on YouTube is that people love the feeling of being motivated.

13:13They don't like putting in the work to do something about the feeling. Number eight, find optimism. I think the biggest obstacle to success is a lack of optimism. I think the world lacks optimism. I think everyone's like, your energy, your energy. I've come to realize it's just optimism. Just happy, just positive. It's what it is. Just like whatever chemicals are in my body, that just allow me to see the bright side. And I just don't think I've realized how few people have that. Like, very few people have it as black and white, 100, zero. Like, I just think everything's good. But like, it doesn't come naturally to a lot of people.

13:58I think that's like, you know, if I was ever to say I'm lucky about something, forget about the business results, it's lucky that that optimism comes naturally to me. Like, I'm just optimistic. Like, I just think that so much works for me because I refuse to accept the negative. Like, you know, and I don't think, I hate when people say it's, you know, it's an option or it's a choice. I agree with you, Susan. I don't think it comes natural to everybody. I think we are just starting on the early stages of really looking at mental health, the brain, meditation. What I want to do with my attention is allow the 2 ,000 of you to the tens of thousands of you to take it.

14:40I want to hand you my optimism, my happiness, my view of the world, my opportunities that I see in the white space. And I want to give it to you for free. And then I want you to win. Number nine, stay driven. How do you stay driven? I'm going to ask you a question. How don't you stay driven? Well, let me get this right. You won the lotto of the universe, which is you are a human being on earth. You, I'm just gonna say this, I mean, I don't think people think about this, you won the lotto. You, in the universe, you're not some weird specimen in Mars that does nothing. You're not, you know, a bird.

15:22You know, you're not a sunflower. Like, you are a human being on Earth. You won the ultimate, ultimate lottery and you're not driven and you're not fired up and you're not going for it and you're willing to sit like a lump and just wait till you die, you suck. Like, I don't know, you suck. Like, how do I stay driven? Because I couldn't even comprehend the alternative. Number 10, last but not least, live your life. The biggest poison in us is regret. It's poison. And I push so hard, so hard, and will, through my vehicle, which isn't meditation, which isn't health and wellness, which isn't non-profit, my vehicle's business.

16:18I can't help it. It's what I love. I love building businesses. I love competing with you. I want to beat you. I love that game. But through that vehicle, I will always push a lack of regret and awareness to how good it really is. You're more than welcome to tell me about how bad it is or why you can't, because or what, but it's just not true. Because if anybody ever did it, then you can too. Stop making excuses. Stop complaining. Nobody's listening. They may make pretend they're listening. The market doesn't care. What you need to do is make one person happy. You. Then you can make everybody else happy.

17:00You know why I like making people happy? Because I'm already happy. and so I implore you to take this last little rant and really look at your face and understand are you doing the things that are putting you in a position to succeed not just in the business world but in life because it's super important because boy when you're happy in life your business can roll and so I'm just trying to figure it out and I've been trying to figure it out in front of you for the last seven, eight years trying to figure out the unlocks EQ, IQ, self-awareness I don't know what they are you know why? because like I told my man it's 330 different unlocks and so I'll go to all of them they're all tried and true and one might hit you yeah it was hard work because I'm actually lazy I talk a good game but I'm full of shit or it might be something else but one and so

17:58I'm back here you decided to sit? you're in for this right? it's good right? This is good shit. You're gonna remember this? Good. One life. One life, my friends. One time. And honestly, I'll leave you with this because a lot of you need it. How you make your money is more important than how much you make.

From the publisher

I want to help all of you guys be the best version of yourself ... this episode is a mash-up of 10 of my "ideologies". Please listen closely as I really think these next 20 minutes can help you take that next step.


This is one of the top 10 throwback episodes, originally from 2019.


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