The GaryVee Audio Experience

Episode: UNPOPULAR OPINION: Losing Actually Turns You into a WINNER

Date: February 25, 2026
Host: Gary Vaynerchuk
Format: 20-minute keynote + 40-minute live Q&A (Brisbane audience)

Overview

In this energetic, no-nonsense episode, Gary Vaynerchuk (“GaryVee”) challenges the conventional fear of failure by celebrating losing as the key to long-term success and fulfillment. Addressing an Australian audience, Gary combines stories from his immigrant experience, hard-won business lessons, and a rapid-fire Q&A to hammer home his core beliefs: losing builds resilience, self-awareness trumps trends, content is the currency of our age, patience outpaces hacks, and happiness—not money—should be the metric for success. The episode’s practical, tough-love advice is woven with memorable quotes and actionable tactics for entrepreneurs and anyone seeking meaning in their work.

Key Discussion Points & Insights

1. Losing Builds Winners

• Gary opens with his “unpopular opinion”:

  “I love fucking losing. I do.” (00:00)

• He credits his childhood adversity—immigrating from the Soviet Union, struggling in school, and never being “the winner”—for his resilience, lack of fear, and drive.
• Main point: Early losses immunize you to future fear and build the foundation for eventual big wins.

2. Redefining Success: Downplay Money, Elevate Happiness

• Gary calls for a societal shift:

  “As a society, we have to redefine success and dramatically start downplaying money and start playing up happiness.” (03:00)

• Chasing money to impress others leads to dissatisfaction:

  “A lot of people are chasing money because they want to buy shit, to conceal insecurities and unhappiness, because we're so worried about judgment from everybody else... and it's completely fucked.”

3. The Power and Necessity of Content Creation

• Gary demands relentless content output:

  “You need to put out pictures, video and written word on the Internet on this device at scale.” (06:20)
  “It's fucking free.”

• He likens success in today’s world to commanding attention across platforms (Facebook, Twitter, LinkedIn, TikTok, YouTube) with contextually relevant content.
• Tactical tip:

  “If you are not producing an enormous amount of content for LinkedIn, you are missing out on Facebook 2011.” (36:10)
  “Influencer marketing is a remarkable arbitrage.” (37:00)

4. Patience Over Hacks

• Many want shortcuts—he delivers hard truth:

  “There is no fucking shortcut. It's a fucking marathon. I fucking worked every day for 15 years before I put out a piece of content in my life.” (14:00)
  “Of course I can be patient with when I think 43 is young as fuck.” (18:10)

• Comparison to fitness:

  “Business is no different than fitness. You want to get more fit, eat healthy and work out, but nobody wants to fucking do it.” (15:40)

5. Self-Awareness & Doing It Your Own Way

• Gary emphasizes self-awareness in both tactics and business choices.

  “Are you comfortable in front of a camera? No big deal. Audio, clip it. Great. You’re not good at that, write. Right?... Do it your way.”

• Happiness and success stem from knowing and expressing your real self—regardless of external expectations.

6. Overcoming Fear of Judgment

• Fear—especially of others’ opinions—paralyzes action:

  “There’s a stunning amount of fear in this room about putting out content… because of the fear of people's opinions that you don't even know. And even worse, opinions of the people you love the most.” (47:35)

7. Advice for Entrepreneurs & Leaders

• True leadership means serving your employees:

  “I have a thousand employees and that means I work for a thousand people versus they work for me.” (32:45)

• On motivating staff:

  “You want your employees to care like you? Give them equal equity like you have.”

• Build businesses around what you love, not just to flip for money, to avoid burnout.

8. Quickfire Practical Tactics

• Platform-specific content:

  “When somebody's on LinkedIn… they're in a business mindset. When they're on Instagram, they're in an entertainment mindset.” (51:40)

• On TikTok:

  “If you're a 67-year-old lawyer, I want to know what the fuck your TikTok strategy is.” (39:40)

• Document vs. create:

  “When I created… ‘document, don’t create’… it unlocked for so many people.” (1:23:15)

Notable Quotes & Memorable Moments

• On loving the process:

  “To me, one of the reasons I think I'm a successful entrepreneur is because I love the game, not the trophies that come from winning the game.” (03:20)

• On building credibility:

  “So many of the things I say at first are pushed against… When you're innovating… If I am right, over time, it builds reputation.” (59:25)

• On leveraging expertise:

  “Always pay attention to who's giving you the advice... the people that were telling you to not call it Shades haven't built a business.” (1:17:35)

• On time:

  “If there's been any breakthrough in my mind over the last half decade, it's: Oh, shit. My ability to contextualize time slightly better than the masses is why I'm so happy.” (17:45)

• On fast-tracking success:

  [How do I fast-track learning about the new world?] “First of all, fuck fast track. But there's definitely a place…G-O-O-G-L-E.” (1:39:10)

Q&A Highlights with Timestamps

1. The One Post for All Facebook Users (52:40)

• Question: What would you post on Facebook if you could reach everyone?
• Gary:

  “How can I help you and why? Cause I want to help. I didn't have to fucking think.” (53:10)
  “When your framework is selfless, the answer is easy. When your framework is selfish, it's hard.”

2. Making a Selfish Product Valuable (55:55)

• Michelle: How do I make selling party frames “unselfish”?
• Gary: “What else can I give you within the framework of my ecosystem?... Ask your audience, ‘What do you want from me?’” (56:40)

3. Balancing Multiple Interests (58:45)

• Ethan: How do I give my all to different projects?
• Gary:

  “You can play both. You can try to go five times, 20%. See what that does.” “Reverse it and don't give a fuck about what people think about your loss, and shit gets real fun. I love fucking losing.” (1:02:16)

4. Family Expectations vs. Personal Dreams (1:04:00)

• Alex: How do I pursue my own path with old-school parents?
• Gary:

  “When you succeed on your own terms, parents always fall into line after you're successful… Limit how much you listen to them.” (1:06:30)

5. Tactic: Content Output Audit (1:11:30)

• Michael: Wants to attract young people to aged care, but not posting enough content.
• Gary:

  “Make content. You’re one video away from striking a chord and having 20 million Australians know what you think about death.” (1:14:00)

6. Getting Started When You’re Young (1:28:20)

• Peter (14 y/o): How to make the most of limited time for a Shopify business.
• Gary: “Don't stress… Enjoy the extracurricular activities… learn your craft, get good, but also enjoy this part.” (1:29:40)

7. When You Hate the Process (1:36:25)

• Arj: "How do I stay in love with the process?"
• Gary: “Either you adjust what you do day to day or you sell the company… This is why I'm so passionate about people building a business around what they love.” (1:37:15)

Timestamps for Key Segments

| Time | Topic / Segment | |---------|-----------------------------------------------------------------------------------------------| | 00:00 | Gary opens on loving “fucking losing” | | 03:00 | Redefining success: money vs. happiness | | 06:20 | The importance of producing content at scale | | 15:40 | No hacks: Business and fitness analogy | | 17:45 | The value of contextualizing time | | 32:45 | Leadership: “I work for a thousand people” | | 36:10 | LinkedIn’s organic reach and influencer marketing trends | | 39:40 | TikTok: massive opportunity, regardless of age | | 47:35 | Overcoming fear of judgment in creating content | | 51:40 | Being contextual with content on different platforms | | 53:10 | The one post Gary would share if he ran Facebook | | 56:40 | How to make selling party frames a value-driven, unselfish act | | 1:02:16 | Embracing failure, letting go of fear | | 1:06:30 | Navigating parental expectations vs personal ambition | | 1:14:00 | “Make content” as the universal answer | | 1:28:20 | Advice for young entrepreneurs balancing school and side hustles | | 1:37:15 | What to do if you fall out of love with your business | | 1:39:10 | The only “fast track” is Google—get educated, put in the work |

Conclusion & Big Picture Takeaways

Gary finishes with a call to action:

• Do. Don’t just think. Fear of judgment is your biggest enemy.
• “You can’t read about pushups. You have to do them.” (48:50)
• The tools are free. The timing is right. But you need to act for yourself and for the long-game, not validation.

If you want a template for fulfillment in today’s business and creative landscape, GaryVee’s prescription is blunt, actionable, and equal parts inspiration and challenge.

For more tactical Q&A, platform advice, and energetic motivation, replay the audience questions from 52:40 onward.
(Episode skips over all mid-rolls/ads by design.)