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Gary Vaynerchuk
When you lose and you have a big blow and you make a mistake, if you make a moral mistake, let alone like a business mistake, or you failed on trying even a moral mistake, like you stole something from a store and you feel bad about it, or you punch someone for no reason in the face, even a moral mistake, you have the opportunity to forgive yourself and the world has an opportunity to forgive you. But making a mistake or losing when you tried something like your business failed, your stand up comedy career failed, your rap career failed, your athletic career failed, like beating yourself up for failing when you tried something is fucking insanity.
Court
It only means that you're insecure and
Gary Vaynerchuk
you're overvaluing other people's opinions. They're worried about how they feel about your failure.
Court
You told everybody in the neighborhood that
Gary Vaynerchuk
you were gonna be the next Jay Z and now you're ashamed or embarrassed because you ended up being the next zj. Like you suck at rap.
Court
Well, okay, I get it.
Gary Vaynerchuk
You peacocked and now everyone's making fun of you. But who gives a fuck if people are making fun of you? This is the GaryVee audio experience. Good to see you. Good morning. Good morning, everyone. Welcome to tea with GaryVee. Do we have an episode number on this?
Court
108.
Gary Vaynerchuk
We've been rusty. I committed to being live a lot more.
Court
Another.
Gary Vaynerchuk
What's that?
Tech/Production Team Member
107.
Gary Vaynerchuk
No worries. 107. A nice little break here that I did not want, but I'm glad to be back on this gloomy Friday in New York City. Good to see everybody. All right, now let's get into the show.
Tech/Production Team Member
It's 1:08.
Gary Vaynerchuk
No worries. It's actually 1:08 again. All right, let's get into the show. Who's got the first question?
Audience Member/Caller
Hey, Gary. First question is kind of a fun one. Who do you think or which historical figure do you think would crush it on social media today?
Gary Vaynerchuk
That's a very good question. Which historical figure would crush it on social media today? I'm gonna go with Richard Pryor. I think Richard Pryor is the greatest modern day comedian. I think he's incredibly witty. And one of the great things about late Richard Pryor, even prime Richard Pryor, was he doesn't give a fuck. So between his comedic skills, his strategic and social skills, his business savvy, and his unparalleled humor, I think Richard Pryor would completely dominate social media today. And that's that Richard Pryor. Migo Cole agrees with me. I appreciate it.
Court
For all the youngsters watching, if you
Gary Vaynerchuk
don't know, get down the rabbit hole. I promise. Next question.
Audience Member/Caller
Gee, in Crush it in 0809, you talked about live shopping almost 20 years ago. What did you see then? Like, this is pre social media explosion.
Gary Vaynerchuk
Even at the time, social media was already real to me. And there was a platform, what I'm doing right now on TikTok Live, there was a platform called Ustream. Ustream was even before Twitch, which was Justin TV, I think. I think it was Ustream then. Justin TV. In that kind of 08 era, I was running live with 20 people watching me in my office in 2008. Usually when I was doing Wine Library TV and then I would come and join them. Cause I'd be off to the side and I would just talk like I'm gonna do right now, right. S lock. I see you, young Von. I see you. Hunter said, gary, you need to lock in Hunter. I was fucking born locked in Hunter. I've been locked in Hunter. I'm always locked in Hunter, you know, So I would interact back then, and I just saw the power of it. And then I have a commercial mind. And I was like, oh, my God, could you imagine? Because I was doing Wine Library TV and I was filming it, and then it would air and there would be links to winelibrary.com, but I had this ustream thing, ironically, on a computer right now. Like, I have the team. And I was like, oh, my God. If Ustream had shopping capabilities in real time. When I was like, oh, this wine is really awesome and epic and this and that, you know, like, for example, Cor, can we pin comic five or we don't have.
Tech/Production Team Member
We don't have comic five in here, but we have comic eight.
Gary Vaynerchuk
Comic eight, yes. Yeah. So, like, here's comic eight. This is the first appearance of Gary Vee. This is Vee Friends. This is my Marvel.
Court
Are you pinning it?
Gary Vaynerchuk
It's pinning it. Beautiful. This is the Marvel and Disney and Pokemon I'm building. This will be an iconic collectible in years to come after I'm done with my mission. Right. The fact that somebody of the people that are watching right now could decide that. That's right. And they're a collector at heart. And like, literally click right now and buy it, like, that's profound. And that wasn't real back in Ustream, but it is real right now. People can do that right now. And that I saw, I knew that would just be, quote, unquote, a matter of time. And so, you know, that's what I always do. I look at every technology and I try to figure out what's just a matter of time. Right. And so I can see all these people viewing. And there it is. Miko Cole just bought a comic, maybe two actually. And there it is. Denise Anthony Alopecia just bought something. Like can you move it a little bit, Court? Like so I can see that part more to the left. Exactly. Yeah, I think you can actually cut. Yeah, I think you covered. Yeah, that's exactly right. Right. So I can see. So I can see what's happening here. Right. I can see that. Kay and Blaine just joined. Hadar just joined our. Thank you so much. James Nugget just joined. I can see it.
Court
So anybody ask your questions? Everybody. Everybody, bottom right corner. Yee haw. The cowboy hat. Thank you for that. Bottom right corner, hit the share button. Hit the share button. Everybody, bottom right corner. Hit that little gift box to join the fan club.
Gary Vaynerchuk
There it is. Look at that fanny right there.
Court
Join the fan club. Top left corner, hit my face and follow me.
Gary Vaynerchuk
Thank you so much. I saw Aaron in the chat saying he's been following me since 2013. I appreciate that. Actually, I had it wrong. Court, you can move it just a little bit over to the right. There we go. Alright, next question.
Court
Everybody, if you have a question for me.
Gary Vaynerchuk
Not Instagram. Everybody on Instagram, you have to go. You have to. This is real content crazy. But you have to go to my TikTok to be part of the show.
Court
Who in the chat right now came from my Instagram. You came from my Instagram live.
Gary Vaynerchuk
And you're here on TikTok. Who is that?
Court
Ask your questions. Use three question marks so my team can see it.
Gary Vaynerchuk
And then. Team, next question.
Audience Member/Caller
Hey you.
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Audience Member/Caller
Gee. Someone in the chat asks, what's the best way to move on from a relationship that was awful?
Gary Vaynerchuk
The best way is actually to give yourself grief.
Court
Grief.
Gary Vaynerchuk
Give yourself grace. To be able to grieve. It's okay. Like, it's okay to be heartbroken. It's okay to be like. But when you say this out loud to someone else like that, it's gonna just take a little time and it's gonna be okay. When they're in the storm, they don't want to hear it. You guys all know that. Like, when you're in the storm, right, gang? Sammy Raghav. Right? Like, Cor. Like, when you're in the storm and someone like, it's gonna be okay, you're not there.
Court
It doesn't mean that they're not right.
Gary Vaynerchuk
The answer to that person that just asked, my friend, you're gonna be okay. Especially if it was a bad relationship. Like, you're gonna be not only gonna
Court
be okay, you're gonna be grateful.
Gary Vaynerchuk
Years to come that that didn't end up being your forever relationship. Like when you're in a bad relationship, a toxic relationship, a relationship that the person's trying to hurt you, manipulate you, they're imposing their own insecurities of themselves onto you, and you become less confident. You don't even see it coming, right? It's seeping nice and slow. But, man, you will be so grateful when you're out of it and you're on the other side and you find a loving relationship, all of you, you need to make sure that you are not in relationships based on your own insecurities. So many of you are in bad relationships because you don't feel great about yourself. And what you don't realize is you're with someone who is either exploiting that or also doesn't feel great about themselves. And you've got two people that don't feel great about themselves beating each other up verbally and emotionally and intentionally or subconsciously. And you got a real fucking problem. Guy says, gary, you dropping 30 points in your next game? The answer is yes, Guy. Yes, Guy, I am. I'm shooting every shot, so don't yell at me when I take those shots.
Court
But that's it, everybody.
Gary Vaynerchuk
So please. I hope that advice helps someone. I hope for some reason somebody just landed on their for you page right here, right now. Heard that. And that became the seed of courage that they will need to break up with someone in the next three to six Months. It won't happen right now. Nobody just heard that. And it's like texting and being like, we're done or calling. I mean, I hope. But I don't think I gave it that. I think I gave it a seed, and so I hope that helps. Let's keep it going.
Audience Member/Caller
Gee. Someone asked, what's your biggest use of AI right now? I think you said a thinking partner.
Gary Vaynerchuk
Thinking partner. I use it for strategy. I use it. I use Claude and ChatGPT and Gemini to think like, I see this in culture. What's going on with this? I talk a lot about baggy pants or charm bracelets for dudes or anything that's happening in culture. Anything that's happening culture. Literally. I typed this in this week.
Court
What's going on with the hats that
Gary Vaynerchuk
have the string in the front? I'm not wearing one right now, but you can clearly see more people are wearing. I love fashion trends. I think they're interesting indicators what artists are doing this, those kind of things. Violeta, you know what's funny? I think rock is amazing for a lot of people. For some reason, I haven't fully gone there yet with Twitter. My Twitter consumption's down a little bit right now. I've just been so busy. Usually I use Twitter to engage and answer questions. Everybody, is this pinned? It's pinned, everybody.
Court
I'm gonna say this nice and slow. This is pinned in the store right now. This is the first appearance of Gary B. In the Veefriends comics. This is a pack.
Gary Vaynerchuk
Actually, you know what? I never open packs.
Court
You might get a rare cover.
Gary Vaynerchuk
Are you fucking kidding me?
Court
I just got a rare cover. I just got a fucking rare cover. Are you fucking kidding me? Cover to 199. Unbelievable. The cracked. Can we do a giveaway? I'm actually giving away and I'm gonna sign it. Friends. I'm giving away $203 right now. I think this would go.
Gary Vaynerchuk
This might actually go for more than 200 on eBay.
Court
Any V, friends? Collectors. Do you know what cracked ice? Do you know what cracked ice Gary B's go for on ebay? This is not Pre recorded.
Gary Vaynerchuk
Casino 26 LAX, man.
Court
What's up? We are giving this away right now. A giveaway right now. A giveaway. Also pinned down below if you want to pick one up. Adam Palmer, thank you for picking one up. Please grab a pack.
Gary Vaynerchuk
They're really fun.
Court
The comics are going to be huge.
Gary Vaynerchuk
I am building the next Pokemon, the next Marvel.
Court
It's called Veefriends.
Gary Vaynerchuk
Is the giveaway Up.
Tech/Production Team Member
Yes.
Court
What do they collect?
Tech/Production Team Member
Show me the pink shopping bag, top left corner.
Court
Everybody, there's a pink shopping bag, top left corner.
Gary Vaynerchuk
Now, pink shopping bag, top left corner.
Tech/Production Team Member
Where is. Where's the timer? It's not showing up. It's right here. The pink shopping bag is weirdly not there on my phone screen, but there
Audience Member/Caller
is a timer there, and you click
Gary Vaynerchuk
on it right there. All right, you guys see it?
Court
Top left corner. Top left corner, pink shopping bag. Click it.
Gary Vaynerchuk
I can't fucking believe I just pulled this.
Court
That is insane. To 199 crank friends. The reason I can't is it's super
Gary Vaynerchuk
hard to get these. FFMama. Good to see you. Time to tell stories is exploding in the comments. Did we get a raid or something?
Court
Here we go.
Gary Vaynerchuk
Next question. I know.
Court
Okay,
Gary Vaynerchuk
Court, I goaded you in. All right.
Court
What's up, G?
Audience Member/Caller
Best bottle of wine. If you're stranded on an island, is it still that champ? Is it champagne?
Gary Vaynerchuk
I do like champagne. Best bottle of wine on a stranded island. I mean, look, what's great about wine is it's like life. It's a personal choice, right? For me, it's champagne. For. For other people, it's a big red wine. Other people, it's a white wine. Some people like rose. The daily Shortlist. If you have a question, please ask it in the chat. Anyone who has a question, ask your questions. Use a bunch of question marks. The team is literally looking for questions. Raghav, Nurey, you got anything to contribute here? Sammy, Matty, what do we got?
Court
We are giving this away. Everybody. Top left corner. Top left corner. Just click it. Just click it.
Gary Vaynerchuk
Get in here.
Court
Get into the giveaway. Top left corner. Get into the giveaway. Click it.
Gary Vaynerchuk
We are giving away a $200 comic book. This is the first appearance of Gary B. And this comic is no fucking joke, y'. All. This comic is no fucking joke. I am absolutely building something massive.
Court
Wellbees, thank you so much for picking up a comic.
Gary Vaynerchuk
It is pinned to the bottom. If you want to buy a pack of it. If you want to buy a pack like this. On it. Next question.
Audience Member/Caller
Hey, Gary. We have someone named Ilus and his question is, as a 20 year old, feeling like after a big punch in the face and falling big time, what should I do to keep trying? I haven't. Didn't heal yet, and my inner self is killing me and telling me I don't even deserve to do anything.
Gary Vaynerchuk
Yeah, Tylus, I think you're just overvaluing other people's opinions. Like when you lose and you have a big blow and you make a mistake. If you make a moral mistake, let alone like a business mistake, or you failed on trying even a moral mistake, like you stole something from a store and you feel bad about it, or you punch someone for no reason in the face, even a moral mistake, you have the opportunity to forgive yourself and the world has an opportunity to forgive you. But making a mistake or losing when you tried something like your business failed, your stand up comedy career failed, your rap career failed, your athletic career failed.
Court
Like beating yourself up for failing when
Gary Vaynerchuk
you tried something is fucking insanity.
Court
It only means that you're insecure and
Gary Vaynerchuk
you're overvaluing other people's opinions. You're worried about how they feel about your failure.
Court
You told everybody in the neighborhood that
Gary Vaynerchuk
you were going to be the next Jay Z and now you're ashamed or embarrassed because you ended up being the next zj. Like, you suck at rap.
Court
Well, okay, I get it.
Gary Vaynerchuk
You peacocked and now everyone's making fun of you. But who gives a fuck if people are making fun of you like friends?
Court
Why the fuck do you still think it's seventh grade? Yo, I need all fucking 1,000 of you to answer me right now. I need 930 of you to answer me right now. Why the fuck do you still think we live in seventh grade? I love you back, Lax.
Gary Vaynerchuk
Garrett's right. Garrett Wiltham's like, ZJ is dope though.
Court
You know, like, happy birthday, Josho. Lm.
Gary Vaynerchuk
I know he said we can't grow up friends.
Court
Why do we think we're in fucking seventh grade?
Gary Vaynerchuk
Like, no one gives a fuck about
Court
your life, and that's a good thing.
Gary Vaynerchuk
And the people that love you care about you, but not about your life.
Court
What I mean by that is your
Gary Vaynerchuk
failures, your missteps, your successes.
Court
They may gas you up. I get unlimited gas up.
Gary Vaynerchuk
But they still can't really care like that. They have their own lives.
Court
When somebody gives me huge daps in
Gary Vaynerchuk
the airport, you're a legend.
Court
How many people here feel like I've
Gary Vaynerchuk
contributed positively to their life?
Court
How many of you feel like I've
Gary Vaynerchuk
contributed positively to your life? Say, added to my life. Robert, Giselle, thank you so much. Miriam, thank you for being here. Delta Boy, Simeos, Mustafa, Kyle. Thank you for checking out the store. I told you, Hugo, simply her look.
Court
All these people said, added to your life. They're giving me flowers.
Gary Vaynerchuk
I love you for that. I'm so humbled. I love you, comma. You can only care about my life. So much. You have your life to live, and I respect that. Tyler Barnes, thank you so much for getting the Squishmallow. Tango Kilo, thank you for getting the Squishmallow.
Court
Tyler got the comic salty 23. Thank you for picking it up. When is this giveaway done?
Tech/Production Team Member
It ended.
Gary Vaynerchuk
Only missed court.
Audience Member/Caller
Clarky. 207.
Court
Clarky. 207. With a huge win. Clarky. 207. ClarkY. Congratulations. That's a huge win, Clarky. Huge.
Gary Vaynerchuk
I might open. I might open another pack.
Court
I'm feeling. I'm feeling we're gonna do another one.
Gary Vaynerchuk
I gotta do this.
Court
Here we go. Let's see if I can get another hit.
Gary Vaynerchuk
I did not. Ooh.
Court
But I got an altcover.
Tech/Production Team Member
Let's go.
Court
I did get an alt cover. I got the J. Lee cover. How many people here are comic fans and know the J. Lee cover? Only 3,000, actually. I did get a nice hit here. How many of you know who Jay Lee is in comic land? This is the Jay Lee cover.
Gary Vaynerchuk
I'm gonna sign this.
Court
This is also an all cover. I did pretty good there.
Gary Vaynerchuk
There's 11,000 of the main cover, as you can see here. There's 11,000 of the main cover, but only 3,000 of the Jay Lee cover. How many of you know Jay Lee? What's up?
Court
It's up. All right, everybody, if you want to enter the giveaway, it's in the same spot, top left corner. Hit the little pink bag. Get into the giveaway. Get into the giveaway. Get into the giveaway.
Gary Vaynerchuk
Thank you for being here. Big L just joined. Jessica just joined.
Court
Bray just joined. Triz just joined. Jackplays.
Gary Vaynerchuk
Dua. Simmy.
Court
Doctor. Good to see you, everybody.
Gary Vaynerchuk
Thank you for entering.
Court
If you don't see it, it's top left corner, it's a pink bag. Top left corner, it's a pink bag.
Gary Vaynerchuk
Everybody ask your questions. Let's keep it moving,
Audience Member/Caller
G. When during the day do you feel most like yourself?
Gary Vaynerchuk
Every second I breathe.
Court
In the fucking morning, I feel like myself. At lunchtime, I feel like myself. In the afternoon, I feel like myself. At dinner, I feel like myself. Late evening, I feel like myself.
Gary Vaynerchuk
Raghav and Sammy, right before I go to sleep, I feel like my fucking self. Who do you think I am? I'm a very simple boy. I keep it super simple out here. I love my fam. I try to do good stuff. I deploy very little judgment on the world at a time that all you motherfuckers think you need to deploy all your judgment to everyone. About everything. About always about everything. Every day. About everything and everyone and everything. I keep it humble. I say to myself every single day, who the fuck do you think you are? In a world where I've done some stuff and a bunch of people that have done nothing in their fucking life think they're fucking God. How about that? How about that?
Court
Allie, good to see you.
Gary Vaynerchuk
Relink.
Court
Good to see you. Tina, nine to five dropout. Good to see you.
Gary Vaynerchuk
Dustin Phillips in the building. Sheeta in the building. The Cunningham Standard in the building.
Court
Rudy C in the building.
Gary Vaynerchuk
I am fearless. Charlie. I'm good.
Court
I am Swift. Lamborambo95.
Gary Vaynerchuk
Uncle Jimmy's in the fucking building. Rutherford Park. Ed B. Says, I am trying to inspire the next generation. Lacks. I have deep passion to leave a positive deposit on the next gen. Because I'm a big fan of youth culture. Huge fan. I'm a massive believer in everyone 15 to 35. I just think they need to get simpler and happier, Less envious and jealous. More confident and calm. Less materialistic, more simplistic. We can keep it real here. All right, next question. Great. Go ahead, Sam.
Audience Member/Caller
Gary, why are we made to believe that nice guys finish last in your opinion?
Gary Vaynerchuk
Because there's just a lot of subconscious human elements that try to suppress people with fear. That's why. Sam, like, do you know how hard it is to be nice? I don't think.
Audience Member/Caller
I don't know.
Gary Vaynerchuk
Not very. I actually think.
Audience Member/Caller
Does it have to be.
Gary Vaynerchuk
I actually think it's the reverse. I actually think it is hard to be nice. I'll explain. To be actually purely nice at all times, you have to be in such a good place within yourself that you have extra energy to be the bigger person to everyone around you. We're, unfortunately, in a very rare era where most people have become so selfish, so self absorbed, so lacking community and loving thy neighbor. So everything is about me and I care about nothing else. So individual that when you go into that place, you are psychoanalyzing every part of your life. You are riding on such ego that you become cynical that you become anxious. Everybody has become so in belief that the world revolves around them that they don't have the capacity for the level of joy and lightness that is required to have consistent kindness come out of them. So now, Sammy, help me with my content to unravel everyone's selfishness and envy. Do you know why people have envy and jealousy? Cause they don't feel good about themselves. I root for everyone. I want every single person that's watching right now to make more money than me and to be happier than me. On the record. That came out so easy. I have no idea how to explain that to you. That came out so easy. I have everybody. I'm lagging. Am I lagging, guys? Am I lagging? I see Yamorie saying that. Are we lagging?
Audience Member/Caller
What do you say to people who are hurt by capitalism and just can't find it in themselves to care like you do? I admire your message, but know a lot of people who are just in pain and can't be bothered to play the game. What would you say to them?
Gary Vaynerchuk
That they're allowed to leave capitalism. That everybody in life is in control of their lives. That, you know, like, you could do anything. Like, I don't understand this concept of thinking you can't. Like, the concept of blaming capitalism for your problems is insanity. It's not communism where you can't leave. Like Cuba and the Soviet Union and North Korea. Like, leave, Like, I guess. Are we talking about political systems? Radov? So, like, this person wants to live in a monarchy, or they want to live in socialism, or do they want to live in communism? I'm trying to think of dictatorship. Like, do they want dictatorship? Like, I'm being serious. Like, I'm not trying to, you know. You know, like, maybe they want a different form. I'm lagging super bad. It looks like we'll figure that out next time. You know, like, you know, like, and there's, I guess there's levels of communist, of capitalism. Maybe. Maybe they're just mad at the USA right now because some people think that's cool. So I guess they can go to Sweden. I think Sweden is, I guess, Sweden's democracy. Right? With an undertone of. I mean, you have capitalism in Sweden. Like, Sweden created Spotify. Daniel Elk is a billionaire. He's also now doing a startup with his billions that he built a gadrillion dollar machine that for $500 scans your entire body and has preventive opportunities for cancers and other things and heart disease. He's going to save lots of people's lives. He would have not been able to do that if he didn't execute his capitalism execution in Sweden. But good news, I don't get to judge. I swear when I say this, I don't think I'm right. You know, they said they admire my optimism. My optimism is grounded in the reality of the world. There's been people that have been happy in dictatorships. They found their way. They had kickbacks to the secret police. Their friend was A friend of the cousin of the dictator. And they had a nice life.
Court
Fine.
Gary Vaynerchuk
Like, I don't get to. I don't get to. I don't get to judge. All I care about is that every person that's watching right now realizes they're in control. Don't like Sweden, come to America.
Court
Don't like America, go to Peru.
Gary Vaynerchuk
Don't like Peru, go to Shanghai. Don't like China, go to Afghanistan. Don't like Afghanistan. Like, no.
Court
Well, Gary, you know,
Gary Vaynerchuk
that's hard. Everything in life that's good is hard. Everything in life that is good is hard.
Court
And, oh, by the way, here's a big one.
Gary Vaynerchuk
I have no interest in imposing my points of view on anyone. I'm just contributing out here. Cause it's fun for me to talk about this shit. I probably have some crazy level of guilt and gratitude of having the best mom in the world so I don't have to learn this shit when I'm 20, 30, 40, 50, 60. This was instilled in me young. So I'm out here spitting it. That's where I'm at. Good to see all of you. Yeah, cheesiest. Not true at all, but that's fine. Mike, how are you? Great to see you. Sorry it's laggy for everybody. I think I'm gonna actually sign off. I have another meeting in six minutes. The lag is something we'll address on the next one. I'll see you guys soon.
Court
Everybody, top left corner. Hit my face and follow when I sign off.
Gary Vaynerchuk
Right now. You'll see me in the middle. Hit notifications and follow. I can't wait to be back.
Court
I'll be back more often.
Gary Vaynerchuk
Love you.
Court
See ya.
Gary Vaynerchuk
Bye.
Court
Hey, everybody.
Gary Vaynerchuk
If you enjoyed this podcast, please go back and look at the prior episodes. They're loaded. I appreciate your attention and thanks for being part of this journey. See you later.
Episode Title: How to Use AI as a Strategic Thinking Partner
Host: Gary Vaynerchuk
Guests/Co-hosts: Court, Tech Team, Audience Callers
Release Date: April 7, 2026
This episode of The GaryVee Audio Experience is a high-energy, interactive “Tea with GaryVee” session, blending rapid-fire Q&A with Gary's unfiltered takes on technology, personal growth, social pressures, and how he leverages AI as a thinking partner. Alongside co-host Court and his production team, Gary fields live audience questions—ranging from harnessing AI tools in business, moving on from failure, cultivating self-forgiveness, and navigating toxic relationships, to classic GaryVee real talk on judgment, self-worth, and cultural trends.
On forgiveness and failure:
“But making a mistake or losing when you tried something… Like beating yourself up for failing when you tried something is fucking insanity.” ([00:00], [14:40])
On AI as strategic partner:
“I use Claude and ChatGPT and Gemini to think … not for replacing work, but to augment strategic decision-making.” ([10:31])
On judgment and self-worth:
“No one gives a fuck about your life, and that's a good thing.” ([16:39])
On personal philosophy:
“I try to do good stuff. I deploy very little judgment on the world at a time that all you motherfuckers think you need to deploy all your judgment to everyone.” ([19:37])
On nice guys/optimism:
“To be actually purely nice at all times, you have to be in such a good place within yourself that you have extra energy to be the bigger person to everyone around you.” ([22:13])
On personal control:
“All I care about is that every person that's watching right now realizes they're in control.” ([27:02])
| Timestamp | Segment / Topic | |------------|-------------------------------------------------------------------| | 00:00 | Opening: Self-forgiveness, failure, and judgment | | 02:02 | Richard Pryor would “crush” social media today | | 03:06 | Gary’s early vision of live shopping from Ustream to TikTok | | 07:47 | How to heal and move on from toxic relationships | | 10:25 | Gary’s main use of AI: strategic thinking partner | | 14:21 | Advice for struggling young people: forgiving oneself, pushing past shame| | 19:19 | When does Gary feel most himself? (“Every second I breathe”) | | 21:41 | Why do people say “nice guys finish last”? | | 24:06 | Capitalism, pain, and personal agency—Gary’s perspective | | 27:37 | Gary's closing philosophy: no one right answer, just contribution |
In this episode, Gary Vee blends tactical business foresight—especially around AI and digital commerce—with emotional intelligence and direct confrontation of modern anxieties about self-worth, failure, and outside opinion. He connects the new (AI as collaborator; live shopping) with timeless GaryVee life-advice: forgive yourself, stop living for others’ approval, deploy kindness, leverage technology authentically, and make agency over your fate the centerpiece of your personal philosophy.
For listeners looking for both actionable insights (especially on using AI in life and business) and emotional encouragement, this episode delivers Gary’s trademark mix of tactical wisdom and motivational straight talk.