How to Use AI as a Strategic Thinking Partner

7 Apr 2026 · 28 min · 15 chapters

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In short

Gary Vee discusses using AI as a “strategic thinking partner,” reframing failure and self-criticism, and answers audience questions during a live Q&A (plus giveaways and product drops). He claims beating yourself up after losing is “insanity” driven by insecurity and overvaluing others’ opinions; mistakes can be forgiven by yourself and the world. He also argues people should not blame systems like capitalism for their lives and insists individuals can leave or change circumstances.

Guests

No specific guests are interviewed; it’s primarily Gary Vee with occasional mentions of chat participants (e.g., Miko Cole, Denise Anthony, Raghav, Sammy, Tyler Barnes, Laxman) and a sponsor read.

Notable examples

Richard Pryor as a historical figure who’d crush social media; Ustream live shopping in 2008; VFriends comic pack giveaways (first appearance of Gary B); advice to a 20-year-old after being punched/falling—stop caring what others think and keep trying.

Written by AI. May contain mistakes. Listen to the episode to check what was said.

Chapters

Tap a time to open that second in VO

The Power of Forgiveness After Failure

0:00 to 0:15

Learn about the importance of forgiving yourself after making mistakes.

Embracing Failure as a Learning Opportunity

0:15 to 0:44

Understand why feeling ashamed of failure is irrational.

Historical Figures and Social Media

1:52 to 2:48

Discover which historical figure Gary believes would excel on social media.

“Who do you think, or which historical figure do you think would crush it on social media today?”

The Origins of Live Shopping

2:48 to 5:05

Explore Gary's early insights into live shopping and its potential.

“if you don't know, get down the rabbit hole, I promise.”

The Evolution of Buying in Real-Time

5:05 to 6:47

Discuss how buying capabilities in live settings have changed.

“And that I saw, I knew that would just be quote unquote a matter of time.”

Healing from Toxic Relationships

7:05 to 9:16

Receive advice on moving on from damaging relationships.

“In a classroom of sodas, most stay quiet.”

The Role of AI as a Thinking Partner

9:16 to 9:50

Understand how Gary uses AI for strategy and insights.

“Guy says, Gary, you dropping 30 points in your next game?”

Cultural Trends and Personal Insights

9:50 to 11:15

Explore how cultural trends inform personal and business strategies.

“I think I gave it a seed and so I hope that helps.”

Giveaway of Gary Vee's Comic

11:15 to 13:06

Get details on the giveaway and significance of the comic.

“I'm actually giving away, and I'm gonna sign it.”

Advice for Young Dreamers

13:06 to 13:55

Get motivational advice for young people facing setbacks.

“The Daily Shortlist, if you have a question, please ask it in the chat.”
Show all 15 chapters

The Burden of Others' Opinions

14:05 to 15:20

Learn how to forgive yourself and move past failures without worrying about judgment.

“Yeah, Tyler, I think you're just overvaluing other people's opinions.”

Life Beyond Judgment

15:20 to 17:19

Discover the importance of focusing on your own life rather than being hindered by others' opinions.

“You peacocked and now everyone's making fun of you.”

Living Authentically

17:19 to 19:50

Understand how to maintain your authenticity and simplicity in a judgmental world.

“Salty23 thank you for picking it up when is this giveaway done?”

The Challenge of Kindness

19:50 to 23:04

Explore the obstacles to being genuinely kind in today's self-centered society.

“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?”

Control and Choices in Life

23:04 to 26:51

Learn about taking ownership of your life choices and the concept of freedom in different systems.

“to unravel everyone's selfishness and envy.”
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Transcript

Automatic transcript. May contain errors.

0:00When 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 punched 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.

0:47It only means that you're insecure and you're overvaluing other people's opinions. You're worried about how they feel about your failure. You told everybody in the neighborhood that you were gonna be the next Jay-Z. And now you're ashamed or embarrassed because you ended up being the next ZJ. You suck at rap. Well, okay, I get it. 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 Gary Vee Audio Experience. Good to see you. Good morning, good morning, everyone. Welcome to Tea with Gary Vee. Do we have an episode number on this?

1:24108. 108. We've been rusty. I committed to being live a lot more. Another, another, what's that? 107. 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. It's 108. No worries. It's actually 108 again. All right. Let's get into the show. Who's got the first question? 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? That's a very good question. Which historical figure would crush it on social media today?

2:10I'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. Miko Cole agrees with me, I appreciate it. For all the youngsters watching, if you don't know, get down the rabbit hole, I promise. Next question. G and Crush It in 08, 09 you talked about live shopping almost 20 years ago.

3:01What did you see then? This is pre-social media explosion 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. What I was doing, 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 because I'd be off to the side and I would just talk like I'm going to do right now. Right? S-Lock, I see you.

3:43Young 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.

4:26For example, Cora, can we pin Comic 5? We don't have Comic 5 in there, but we have... Comic 8? Comic 8, yes. Yeah? So here's Comic 8. This is the first appearance of Gary Vee. This is Vee Friends. This is my Marvel. Are you pinning it? It's pinning. 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.

5:03And 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, yeah, exactly. Yeah, I think, you can actually, yeah, I think you covered it.

5:44Yeah, that's exactly right, right? So I can see what's happening here, right? I can see that Kay and Blaine just joined. Hadar just joined. Thank you so much. James Nugget just joined. I can see it. So anybody, ask your questions, everybody. Everybody, bottom right corner. Yeehaw, 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. There it is. Look at that fanny right there. Join the fan club. Top left corner. Hit my face and follow me. Thank you so much. I saw Aaron in the chat saying he's been following me since 2013.

6:18I appreciate that actually I had it wrong you can move it just a little bit over to the right there we go alright next question everybody if you have a question for me 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 who in the chat right now came from my Instagram you came from my Instagram live and you're here on TikTok who is that ask your questions use three question marks so my team can see it and then team next question We're the Hartford, with decades of experience insuring millions of unique small businesses.

6:52When it comes to your small business insurance, one size absolutely does not fit all. Get a quote or find an agent today at thehartford.com slash small business. In a classroom of sodas, most stay quiet. Then there's Mr. Pibb, sweet cherry, bold outbursts, the kind of flavor that gets attention.

7:19gee someone in the chat asks what's the best way to move on from a relationship that was awful by the best way is actually to give yourself great grief uh 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 wanna hear it. You guys all know that. Like, when you're in the storm, right, gang? Sammy, Raghav, right? When you're in the storm and someone's like, it's gonna be okay, you're not there.

7:59It doesn't mean that they're not right. 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 be okay you're gonna be grateful 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.

8:41All 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.

9:23So don't yell at me when I take those shots. But that's it, everybody. 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 is 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. Gee, someone asked, what's your biggest use of AI right now?

10:01I think you said a thinking partner. Thinking partner. I use it for strategy. I use it, I use Claude and ChatGBT 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 in culture. Literally, I typed this in this week. What's going on with the hats that have the string in the front? I'm not wearing one right now, but you can clearly see more people are wearing, like I love fashion trends. I think they're interesting indicators. What artists are doing this?

10:36Like those kind of things. Violetta, 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. God, it's just been so busy. Usually I use Twitter to engage and answer questions. Everybody, is this pinned? Everybody, 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 V Friends comics. This is a pack. Actually, you know what? I never open packs. You might get a rare cover. Are you fucking kidding me? I just got a rare cover.

11:11I just got a fucking rare cover. Are you fucking kidding me? Covered a 199. Unbelievable. The crap. 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, this might actually go for more than$200 on eBay. Any VFriends 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 Casino 26 Laxman 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 they're really fun the comics are going to be huge I am building the next Pokemon the next Marvel it's called VFriends is the giveaway up?

11:57what do they collect? show me everybody there's a pink shopping bag top left corner now pink shopping bag top left corner

12:19all right you guys see it top left corner top left corner pink shopping bag click it I can't fucking believe I just pulled this. That is insane. To$199. Friends, the reason I can't is it's super hard to get these. FF Mama, good to see you. Time to tell stories is exploding in the comments. Did we get a raid or something? Here we go. Next question. I know. Okay, okay.

12:45I goaded you in. All right. What's up? Gee, best bottle of wine if you're stranded on an island. Is it still that champagne? 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 other people, it's a big red wine. Other people, it's a white wine. Some people like rosé. 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 Naray, you got anything to contribute here?

13:17Sammy, Matty, what do we got? We are giving this away. Everybody, top left corner. Top left corner. just click it just click it get in here get into the giveaway top left corner get into the giveaway click it 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 well bees thank you so much for picking up a comic 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 Hey Gary, we have someone, it's Eyeless, 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?

14:04I haven't, didn't heal yet, and my inner self is killing me and telling me I don't even deserve to do anything. Yeah, Tyler, 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 like beating yourself up for failing when you tried something is fucking insanity it only means that you're insecure and you're overvaluing other people's opinions you're worried about how they feel about your failure You told everybody in the neighborhood that you were gonna be the next Jay-Z.

15:17And now you're ashamed or embarrassed because you ended up being the next ZJ. Like you suck at rap. Well, okay, I get it. You peacocked and now everyone's making fun of you. But who gives a fuck if people are making fun of you? Like friends, 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. Garrett's right. Garrett Wiltham's like, ZJ is dope though. You know, like, happy birthday, Josh-O. LM, I know. He said we can't grow up.

16:03Friends, why do we think we're in fucking seventh grade?

16:10Like no one gives a fuck about your life and that's a good thing. And the people that love you care about you but not about your life. What I mean by that is your failures, your missteps, your successes. They may gas you up, I get unlimited gas up. But they still can't really care like that. They have their own lives. When somebody gives me huge daps in the airport, you're a legend. How many people here feel like I've contributed positively to their life? how many of you feel like I've contributed positively to your life? Say added to my life. Robert Giselle, thank you so much. Miriam, thank you for being here.

16:50Delta Boy, Simius, Mustafa, Kyle, thank you for checking out the store. I told you. Hugo, simply her. Look, all these people said added to your life. They're giving me flowers. 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 squish mellow Tango Kilo thank you for getting the squish mellow Tyler got the comic Salty23 thank you for picking it up when is this giveaway done? Clark?

17:29Clarky207 Clarky207 with a huge win Clarky207 Clarky So congratulations, that's a huge win, Clarky. Huge, I might open another pack. I'm feeling, we're gonna do another one. I gotta do this. Here we go, let's see if I can get another hit. I did not. Ooh, but I got an alt cover. I did get an alt cover. I got the Jay Lee cover. How many people here are comic fans and know the Jay 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 I'm gonna sign this this is also an all cover I did pretty good there 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 that?

18:23it's up? alright 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 thank you for being here Big L just joined Jessica just joined, Bray just joined, Triz just joined, Jack Plays, Dua, Simi Doctor. Good to see you everybody. Thank you for entering. If you don't see it, it's top left corner, it's a pink bag. Top left corner, it's a pink bag. Everybody ask your questions, just keep it moving. G, when during the day do you feel most like yourself? Every second I breathe. 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, Raghav.

19:10And Sammy, right before I go to sleep, I feel like my fucking self. Who do you think I am?

19:23I'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?

20:10How about that? How about that? Ali, good to see you. Really good to see you. Tina, 9 to 5 dropout, good to see you. Dustin Phillips in the building. Sheeta in the building. The Cunningham Standard in the building. Rudy C in the building. I am fearless. Charlie, I'm good. I am Swift. Lambo Rambo 95. Uncle Jimmy's in the fucking building. Rutherford Park, Ed B says. I am trying to inspire the next generation, Lax. 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.

21:06We can keep it real here. All right, next question. Two minutes and you will. Great. Go ahead Sam. Hey Harry, why are we made to believe that nice guys finish last, in your opinion?

21:22because there's just a lot of subconscious human elements that try to suppress people with fear. That's why I say it. Like, do you know how hard it is to be nice?

21:42I don't think, I don't know, not very. 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.

22:07We'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.

23:02So now Sammy, help me with my content to unravel everyone's selfishness and envy. You know why people have envy and jealousy? because 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 Yammery saying that. Are we lagging? What do you say to people who are hurt by capitalism and just can't find it in themselves to care like you do?

23:44I 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? That they're allowed to leave capitalism.

23:57That everybody in life is in control of their lives.

24:03That, 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.

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24:34Like I guess, are we talking about political systems? runoff. So 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,

25:12you know, like, and there's, I guess there's levels of communism, of capitalism. 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 gonna save lots of people's lives.

26:00He 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 fine 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?

26:44Come to America. Don't like America? Go to Peru. Don't like Peru? Go to Shanghai. Don't like China? Go to Afghanistan. Don't like Afghanistan? Go.

26:56Well, Gary, that's hard. Everything in life that's good is hard.

27:04everything in life that is good is hard. And oh, by the way, here's a big one. I have no interest in imposing my points of view on anyone. I'm just contributing out here because 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.

27:38That's where I'm at. Good to see all of you.

27:44Yeah, 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. Everybody, top left corner, hit my face and follow. when I sign off right now. You'll see me in the middle. Hit notifications and follow. I can't wait to be back. I'll be back more often. Love you. See ya. Bye. Hey everybody, 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.

28:20See you later.

From the publisher

In this episode of Tea with GaryVee, I dive deep into why you need to stop overvaluing other people’s opinions and start forgiving yourself for your failures. Whether it’s a business that didn’t take off or a personal mistake, I explain why "peacocking" and worrying about your neighbors' judgment is stalling your growth. I also discuss my early predictions for live shopping and how I’m currently using AI tools as strategic thinking partners to stay ahead of cultural trends.

You’ll learn about:

  • The "Insanity" of Beating Yourself Up After Failure

  • Why Richard Pryor Would Have Crushed Social Media

  • Using AI (Claude, Gemini, ChatGPT) for Strategy

  • How to Heal from Toxic, Insecure Relationships

  • The Reality of Accountability in any Economic System


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