The GaryVee Audio Experience: "10 Ways to Have a Winner's Mindset"

Hosted by Gary Vaynerchuk | August 15, 2025

Episode Overview

In this passionate solo episode, Gary Vaynerchuk shares his ten core principles for developing a winner’s mindset in business and in life. Through candid storytelling and direct advice, Gary breaks down how self-awareness, optimism, and relentless action are key to long-term fulfillment, not just external success. True to his signature style, he challenges listeners to rethink conventional wisdom, take accountability, and define happiness on their own terms.

Key Themes & Discussion Points

1. Attack Mondays & Fully Realize Your Opportunity

• Gary challenges the accepted dread of Monday mornings:
  • "It breaks my heart…my friends live for Friday night…Monday morning's the worst." [00:03]
  • He argues the internet has created limitless opportunity, making excuses obsolete.
  • Highlights the randomness of existence ("could have ended up a bus, a tree") and the precious chance to be alive and pursue passions.
  • Memorable quote:
    • "I'm gonna make Monday morning my bitch. I'm gonna make you Saturday, Monday morning." [01:13]

2. Chase Happiness, Not External Markers of Success

• Pursuing what you love is paramount—even if it won’t make you rich.
• Reality check: Happiness might not be compatible with wealth for everyone.
• Speaker’s Personal Take:
  • "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." [02:07]
  • Stresses self-awareness over society’s or family’s definition of ‘success’: "Don't let me. Don't let your parents push you into what success is. It's different for all of us." [02:44]

3. Stay in Your Lane & Double Down on Strengths

• Self-awareness: Know who you are, focus on your strengths, and punt your weaknesses.
• Memorable quote:
  • "I've stayed very, very, very narrow. For me, it's lucky. The reason I've been able to grow is my narrow thing is consumer behavior, which I can play against anything." [04:08]

4. Embrace Failure & Take Action

• No dwelling: Gary hasn’t encountered a failure he didn’t overcome.
• Humankind is resilient by nature, but society profits by pushing insecurity.
• Memorable quote:
  • "We're really strong. We're just being sold that we're not because there's a lot of money in telling us that we're not pretty enough, thin enough, smart enough, good enough." [06:25]
• Calls out the money-driven market that thrives on self-doubt.

5. Play the Long Game

• Relentless focus on long-term over short-term gains.
• Cites his business strategy of sacrificing short-term profit for greater long-term rewards.
• Interesting insight:
  • "99% of the market is short term and the 1% that isn't and has the talent wins every time." [08:50]
• Critiques irrational market behavior, referencing a stat that "85% of what humans make decisions about is irrational." [09:45]

6. Figure Yourself Out (‘Do You’)

• The most important step: Define your own dreams and ambitions.
• Warning against copying others—even Gary himself.
• Clarification:
  • "The only advice I'd like to give to everybody is to do you, define what your North Star is, to understand yourself…" [11:00]
• Urges listeners to reject comparison and societal pressure.

7. Take Action Over Mere Motivation

• Points out that most people love feeling motivated more than actually acting.
• The goal of his content: Push people to act, then move on.
• Frustration:
  • "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." [14:22]

8. Find Optimism

• Core Belief: Optimism is the ultimate success-enabler.
• Recognizes it's partly innate, not always a choice, and references mental health.
• His mission: Share his optimism, “hand it” to others freely.
• Memorable quote:
  • "I refuse to accept the negative…if I was ever to say I'm lucky about something…it's lucky that optimism comes naturally to me." [16:21]

9. Stay Driven

• Being a human is winning the "lotto of the universe."
• Anything less than fully going for it is unfathomable.
• Vaynerchuk at his bluntest:
  • "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…You suck." [17:51]

10. Avoid Regret & Live Your Life

• Poison to avoid: Regret.
• Life and career should be about happiness, not complaining or excuses.
• The market doesn’t care; make yourself happy first.
• Impactful closing:
  • "How you make your money is more important than how much you make." [21:12]

Notable Quotes & Moments

• On Monday blues:
  • "What if I told you this was the last Monday morning of your life? Would you complain about your crap job or that test you don't want to take?" [00:45]
• On self-definition:
  • "Don't do DailyVee or all these videos for you to be like me. I don't think anybody should be like me..." [12:52]
• On perseverance:
  • "People have gotten through much worse…our grandparents and our great grandparents…People were persecuted and killed. We do not have real headaches." [06:03]
• On motivation vs. action:
  • "The reason there's gonna be a billion motivational views today on YouTube is that people love the feeling of being motivated. They don't like putting in the work to do something about the feeling." [14:38]
• On optimism and luck:
  • "If I was ever to say I'm lucky about something, forget about the business results, it's lucky that optimism comes naturally to me." [16:27]
• On drive:
  • "How do you stay driven? ... Because I couldn't even comprehend the alternative." [17:53]
• On meaning:
  • "One life. One life, my friends. One time." [21:05]
• Final advice:
  • "How you make your money is more important than how much you make." [21:12]

Timestamps for Essential Segments

• 00:01–01:40: Rethinking Mondays & the opportunity of modern life
• 01:41–03:45: Happiness vs. wealth; self-awareness
• 03:46–05:13: Staying true to yourself and your strengths
• 05:14–07:04: Handling failure; societal pressures
• 07:05–09:54: Playing long-term business strategy; rationality vs. irrationality
• 09:55–14:15: Defining goals for yourself; avoiding imitation
• 14:16–15:47: The necessity of taking action, not just consuming motivation
• 15:48–17:34: The scarcity and importance of optimism
• 17:35–18:40: Drive stemming from gratitude for existence
• 18:41–21:12: Regret, happiness, and focusing on fulfillment over money

Conclusion

Gary Vee’s "10 Ways to Have a Winner's Mindset" is a high-energy, no-excuses manifesto urging listeners to live authentically, lean into their strengths, be relentlessly optimistic, and avoid regret at all costs. His advice is tough, but grounded in deep self-reflection and genuine intention to help people win on their own terms.

Final takeaway:
"One life. One time. How you make your money is more important than how much you make." [21:12]