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AI, Fear, Opportunity — and When to Go All In on Your Side Hustle

The GaryVee Audio Experience

Wed Nov 26 2025

Summary

Podcast Summary: The GaryVee Audio Experience

Episode: AI, Fear, Opportunity — and When to Go All In on Your Side Hustle
Date: November 26, 2025
Host: Gary Vaynerchuk

Overview

In this dynamic, high-energy "Tea with GaryVee" episode, Gary Vaynerchuk tackles the major themes of artificial intelligence (AI), confronting fear, embracing new opportunities, and knowing when to fully commit to your side hustle. The episode blends community Q&A, motivational calls, and unfiltered practical advice on leveraging passion and knowledge—especially in today's rapidly evolving AI-driven world. Gary repeatedly returns to the core message: the only way forward is action rooted in self-awareness, accountability, and ceaseless execution.

Key Discussion Points & Insights

1. Making Money Online: Passion & Authenticity Over Trends

[01:17–03:18]

Gary stresses that the real secret to online income is combining what you’re passionate about and what you actually know.
He warns against chasing the latest trend (crypto, cannabis, real estate) if it doesn't genuinely excite you or fit your expertise.
Quote:

"My friends, it is passion and knowledge. It is passion and knowledge. Say it with me, everybody." — Gary Vaynerchuk [01:43]
Gary encourages listeners to build around true interests (e.g., if 14 again, he’d focus on Knicks, Jets, Fantastic Four, or Madden).
Bottom line: The formula is simple—passion + knowledge = long-term success.

2. AI: Fear, Opportunity, and the Future of Work

[03:26–05:36 | 28:24–29:30 | 30:53–32:24]

Gary is "fully bullish" on new AI tools like Soro2, emphasizing their power for both creators and broader users.
Key perspective: AI won’t take all office jobs—people adept at using AI will. It will redistribute labor and create new opportunities (e.g., increased leisure fueling service and experience economies).
Quote:

“AI will not replace all office jobs. Humans that know how to use AI will replace.” — Gary Vaynerchuk [03:34]
He draws parallels with “the tractor” in the industrial revolution, which opened new opportunities, not just replaced farm jobs.
Addresses concerns about deepfakes and identity, reassuring that humanity—and tech like blockchain—will adapt and solve these challenges in time.
Quote:

"I believe in humanity. I believe in us." — Gary Vaynerchuk [29:23]
Takeaway: Don’t demonize AI. Learn and use it daily to stay relevant.

3. Overcoming Fear and Excuses: Caller Stories

a. The Aspiring Chef: When Is It Time to Go All In?

[05:36–20:51]

Aspiring chef struggles to create content due to family, fear, and feeling "too old" at 39.
Gary’s blunt advice: Stop dwelling on the past, focus all available energy on execution, and leverage AI tools for content.
Quote:

"Your interest in dwelling about yesterday is stopping you from attacking today, which is keeping you away from being happy tomorrow." — Gary Vaynerchuk [13:56]
He demystifies the idea that it's “too late” and offers a practical routine: Work, care for family, then spend evenings creating content—repeatedly for years.
Sets an accountability challenge:

"If you do 100 TikTok posts in a row, when you get to 101, you email me. I will give you crazy love and awareness. I will get your first gig in Vegas for you." — Gary Vaynerchuk [19:44]
Lesson: Age is not a barrier; excuses are.

b. Amanda’s Story: Career Loss, Divorce, and Re-Invention

[25:10–27:45]

Amanda shares losing her job and facing divorce, expressing hope rooted in purpose and connection.
Gary gives emotional support and offers access to a Vayner event, reinforcing the power of community and self-belief.

4. How AI Is Shaping Future Status & Community

[21:04–25:10 | 30:46–32:24]

With knowledge commoditized by AI, status will come from unique IRL (in real life) experiences and human connection—organizing communities, clubs, and leadership roles (e.g., run clubs, supper clubs, group dating).
Quote:

“I think in the rise of AI everyone, I really believe the rise of humanity and human traits. Emotional intelligence, doing physical things. I think physical things will rise in value.” — Gary Vaynerchuk [23:51]
Advocates exploring non-digital forms of connection; expects new trends to emerge from “fighting the matrix.”

5. Navigating Side Hustles & When to Go “All In”

[39:19–42:52]

Responding to a question about quitting a job to focus on a side hustle, Gary is unequivocal:
Quote:

“They're wrong because they're scared. Why would you take their fear? Take my optimism. … Jump. The end.” — Gary Vaynerchuk [39:38]
He underscores the importance of self-accountability and recognizes jobs will always be available if it doesn’t work out.

6. Happiness, Mistakes, and Accountability

[29:55–30:46 | 35:22–39:07]

Mistakes and distractions are a given; what matters is not dwelling on them.
Quote:

“What do I do? I don't cry about it and I'm excited about the experience and I make fun of myself if I did the wrong thing or I proud of myself because I learned something through the mistake and I just move forward.” — Gary Vaynerchuk [30:05]
Reiterates that happiness is the true metric—not monetary success.

Memorable Moments & Quotes

On Passion vs. Trend-Chasing:
“You’re not gonna make money on crypto if you’re not passionate about crypto.” [01:36]
On the Toxicity of ‘I Wish’:
“I never say I wish. You cannot say I wish, brother.” [16:02]
On Age as an Excuse:
“You’re 39. I’d punch my pee pee to be 39. And you’re crying about being 39.” [15:17]
On Fear & Action:
“The greatest illness … is your infatuation with yesterday that you have no control about.” [14:13]
On Self-Worth:
“You are amazing. I need all of you to understand you’re amazing.” [59:03]
On Excuses and Accountability:
"No more complaining, no more crying. Stop it. No one's listening to you. Complaining and excuses are poison...it's your fault. And the second you realize it’s your fault, life gets good. And the second you think it’s their fault, life gets bad." [41:39, 44:44]

Timestamps for Key Segments

| Segment | Timestamps | |---------------------------------------------|--------------------| | The secret to making money online | 01:17–03:18 | | Gary on AI’s impact and Soro2 | 03:26–05:36 | | Caller: Aspiring Chef (side hustle debate) | 05:36–20:51 | | On future status in an AI world | 21:04–25:10 | | Amanda’s story, personal breakthroughs | 25:10–27:45 | | AI, fear and trust in humanity | 28:24–29:30 | | Mistakes, happiness, and learning | 29:55–30:46 | | Local vs. global culture | 30:46–32:24 | | Accountability, “NO MORE WaWa” rant | 39:19–44:44 | | Scaling, hiring, and business questions | 33:22–39:07, 47:58–53:19 | | Caller: Landscaping Business & AI | 53:22–56:56 | | Relationships & self-esteem intervention | 57:04–59:17 |

Tone & Style

Gary is as trademark blunt, energetic, and motivational as ever. He cracks jokes, isn’t afraid to curse for emphasis, challenges entitlement, and fiercely campaigns for personal accountability and optimism. The show’s high engagement and rapid-fire Q&A keep it lively and accessible.

Conclusion

This episode is a masterclass in marrying tough love with actionable advice. Gary tackles AI’s opportunities and threats, dismantles excuses around starting late or fearing failure, and shows—through both his own stories and live caller coaching—how to convert adversity into forward momentum. Whether you’re pondering when to leap into your side hustle or how to navigate AI’s impact, Gary hammers home that the ultimate unlock is self-belief, practical execution, and ruthlessly honest self-reflection.

Notable Challenge:

“If you do 100 TikTok posts in a row, when you get to 101, you email me. I will get your first gig in Vegas for you.” — Gary Vaynerchuk [19:44]

Final Thought:
"You are in control, comma, got it?" — Gary Vaynerchuk [41:19]

For more actionable insights and Gary’s signature brand of inspiration, replay this episode or join the community live on TikTok for upcoming Tea with GaryVee shows.

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Transcript

Gary Vaynerchuk (0:00)

Before you go to the podcast, I've got a big announcement. I know several years ago a lot of you bought 12 books of 12 and a half to get the NFT, the book games. NFT. I also know that a lot of people have dropped off on their journey with Veefriends, which is a massive mistake because what we're doing on Burn island and what we're doing on base with book games is remarkable. So you need to go to veefriends.comoldbooks with an S. You will go to that landing page and we will help you explain if you are trying to figure out where your NFTs are, how to bring them over to the website and how to start activating them so that you can start using them for all the incredible exchanges and draws and raffles and experiences that we're doing for people that actually own the book games. So please go to vfriends.comoldbooks where you can start your journey on reactivating your book games.

Ben (0:48)

Journey.

Gary Vaynerchuk (0:49)

This is the GaryVee audio experience. Good morning everyone. Welcome to Tea with Gary Vee. Episode 95. Big shout out to Quinn and Williams. Number 95 from from the jets, now Cowboys. Hope everybody is super well. All right pops, what do you got for me?

Community Questioners (1:06)

Paul is asking. My 13 year old son recently started a faceless YouTube shorts channel. Do you believe in the faceless YouTube trend? And if you were 13 today, what would you be doing to make money online?

Gary Vaynerchuk (1:17)

Listen, if you want to make money online, who here wants to make money online? Please put five dollar signs in the chat. Let me give you the secret. Who wants a secret? If I was 14 today, I'd make money doing something around Knicks, Jets, Fantastic Four. I was reading Fantastic Four at 14. Madden, John Madden Football on Sega Genesis. What you need to understand, everybody is the reason most of you can't make money online is that you're trying to follow a trend that you're not passionate about or you don't know about. If you don't know crap about crypto and you're not passionate about crypto, but you heard there's money to be made on crypto. You're not going to make money on crypto if you're not passionate about cannabis and you're not knowledgeable about cannabis, but you heard there's money in cannabis. You're not going to make money on cannabis if you're not passionate about real estate. If you don't know dick about real estate, but you heard there's money on real estate, you, you're not gonna make money. My friends, it is passion and knowledge. It is passion and knowledge. Say it with me, everybody. All four of you. Passion, knowledge. Passion, knowledge. All of you in the chat, why'd you guys give up after two Sid, Come on. Passion, knowledge, passion, knowledge. Passion, knowledge, passion, knowledge. Everybody on Instagram. You're missing it. We're going crazy on TikTok. Gary b.comt we're. We're having an incredible show. Tea with Gary Vee here, everybody. If you want tea with Gary Vee and live TikTok sessions. I'm gonna be live all of 26. I am gonna be live all of 20. Did you see what I just. I did a spit. I am gonna be live all of 2026. At parties on my head. My friends, we are doing nothing but positivity and practicality, optimism. I'm gonna teach you how to make money and I'm gonna teach you more importantly, how to be happy. And that is my mission, that is my goal. And I'm gonna dominate it in 2026. All right, let's do more questions from the community.

Gary Vaynerchuk (3:26)

I think it could be both or neither. But I'm fully, fully bullish on it. And we'll be using it heavily. AI will not replace all office jobs. Jamie B. Humans that know how to use AI will replace. Some are gonna replace humans like Courtney and Pablo will have the power of four to five employees at their fingertips that they're great at AI and that will create a reset. Courtney and Pablo in that scenario would make more money. One or two people that would work at VaynerMedia no longer work at VaynerMedia. That is true. But the overall economy gets expanded dramatically by AI, thus allowing those two people that don't work at Vayner to work at Live Nation. Cause live events now work. Cause now we're on a four day work week. Now we have three days of leisure. Because of the ramifications people don't get. This is what people don't understand. Hey everybody. Hope you're enjoying the podcast right now. Make sure you follow the podcast. That's why I'm interrupting. Let's keep going on this show, but follow the podcast. It'll make my mom super happy. What people don't understand is the ramifications of the thing they're scared of. AI takes over. We work three days a week. We work three Days a week. Companies pay more taxes to subsidize us because we all lost our jobs. We now have four days of leisure. We have four days of leisure. We drink more beer. We go to more concerts. We go. We join more clubs. Those people need marketing employees. So two. So two people that don't work at Vayner now because Pablo and Courtney are. Are able to be the workers of three people. Those two people now work at Miller Light and do activations. Like, people don't get it. This is what the tractor did. Oh, the tractor. Everyone's working on a farm. We're all going to be out of jobs. We built corporations on the back of it. We built the future. We're going to build the future because of AI. That's my answer there. But all of you need to, like, start using AI. Everybody here should be using ChatGPT and everything else every day. All right, let's get somebody on screen. Sammy, what's good, bro?

Gary Vaynerchuk (21:09)

Well, I assume that he thinks that knowledge was status. And I would argue memorizing things and doing good at tests and going to a college was not necessarily knowledge. I know that. It was modern knowledge. New status is already, you know, been established in this new world. New status now is, you know, literally 10 years ago, nobody thought about the concept of how many people follow you. For normal citizens, that wasn't even a thing. Wasn't even a thing. And that became status. I think the new status in an AI world is the people that are dominating in real life experiences. I think people that have a 10,000 person run club and are the organizers of that, and 10,000 people show up literally to like a stadium parking lot or like a grassy knoll. And these human leaders, I think, you know, guidance counselors and coaches and human humanity, I think, gotta sip that coffee. Anything you put on my face in the stuff, I'm gonna act. There's Elvis. I'm like, there's a cowboy. I do yeehaw. And also if you've been hanging with me in lives, you know, the ao and there's a good morning right there. So much fun. For everybody who normally watches tea with GaryVee and other platforms, we're gonna find our way here. Cause there's a lot more stimulation on TikTok. But I wanna focus on the questions. I think in the rise of AI everyone, I really believe the rise of humanity and human traits. Emotional intelligence, doing physical things. I think physical things will rise in value. Supper clubs, dating clubs, group dating. I'm very big on group dating. I'm very hot on this. This was huge in India. During the early dating stuff, there was. I don't remember the name. Maybe somebody here is watching from India. There was that Indian dating app that was group dating. It was like an app when everyone was like doing Tinder and Match here. There was an app in India that was crushing. That would be like four and six people having a date. So I think group dating is gonna explode a little bit as people get more introverted and even more and then start to go to human. But they were like in the. Look at this thing that they just gave me. You know, right now, men have a lot of courage. Dming and swiping. As we start to counter the digital age in the next decade and we go back oh, my God. Vroom, vroom. I got a lot of yee haw. I'm gonna have to think of a. As we go into post AI scaled human activities, I think dating non digital is gonna be a big deal. And I think that a lot of kids in Gen Alpha and young, you know, older gen zers, it's already funny to say that we're gonna blink and we're gonna be in this older Gen Z. I mean, remember Millennials, not about those characters. All of you are like, they're like, you guys are starting to feel like us, Gen X. No one ever knew who Gen X was. We never get talked about. There's people in here. Who here has never heard of Gen X? It's boomers, millennials, Gen Z. There's people literally have never heard of Gen X. I'm in Gen X. Like, anyway, older gen zers, Gen Alpha, I think are going to fall in love with group dating. So I'm looking at a lot of businesses right now. Festivals, you know, Spartan races and marathons and cooking clubs and basketball pickup businesses. And, you know, I think there's just a lot coming on that. So anyway, I think status is going to grow in people that are fighting the matrix, the most human. Yeah. All right. Amanda, how are you? Hey.

Gary Vaynerchuk (35:29)

You already know your problem. You're working remote. Working remote sucks for a lot of people. It was good in theory. Like, I don't like traffic, I hate to commute, I like hiding. Working remote really hurt a lot of people who need other human beings. Friends, there's unequivocal data that people live longer when they're in a community. Friends, you're sitting at home and all this miraculous time that you've saved, you're doom scrolling. Yay. I've saved two hours from commuting so I can scroll in my phone and scare myself and build envy and jealousy because I see other people are happier than me. Yay. You did it. You're super progressive. Congrats. You fought the man. You did it. You beat the man. Congrats. You beat the man. You found that 75 extra minutes so you could blow it and have no sense of community. Humans, interaction. You lost. Now other people. 33 years old, two kids, have a couple friends in the neighborhood, work from home. When there's no absolutes in life, friends, there's just your circumstance. There's no absolutes in life, there's just your circumstance. Big shout out to everyone who works from home and found more happiness. But a lot of you, especially single under 30, you lost the osmosis of the things you learn in an office. You lost the serendipity of meeting a new friend. You lost the serendipity of going out with your bar mates at night and then getting a little tipsy and hooking up with a co worker. You lost your buddies that sit next to you that are really into anime. You've never been into anime. While you're working, you're like, why are they talking about anime? And then all of a sudden, three weeks later, you're at Comic Con dressed up as a super awesome person. I don't know. Like, God damn it, I hope that really helps someone. How many people just heard me answer that question and it really helped them. They really understood that maybe working from remote has actually stunted them. How many people did that help, but helped? You may want to start looking for a job in office, you know, like, you just might, you know, like, I don't know, like, follow me here on this. Like, here's our office, right? Like, you know, like, here it is, you know. Oh, what happened? Is it. Oh, we're good. Okay. Yeah, yeah, we're good. You know, so, like, hey, guys, how are you? What's up with people? You know, like, there's Nick. Look, Nick and JT are going and like, right. Like, people are just, you know, in it. And like, I feel. You did lost audio, but it's still video. But video still. Lost audio. Oh, I did have audio. It's. There's a range, though. All right. Nonetheless, I think point was made, right? I think the point was made, right? Did everybody get the point? Did we get the point? Was the point made? You know, like, was a point made? Pablo, back to you.

Gary Vaynerchuk (39:38)

She's wrong. They're wrong. She's right. Jump. The end. No more. No more being around the bush. I need a bush here, guys. I'm gonna need a bush. They're wrong because they're scared. Why would you take their fear? Take my optimism. And here's the dirty little secret, everyone. Jobs will be there if you fail. And I know they're telling you that AI is going to take all the jobs. AI is not going to take all the jobs. People that know how to use AI are going to take all the jobs. So jump. And then work on learning AI and then that's that. What are five words that can change someone's life? You're in control, comma, got it? That's it, my friends. You are in control. You're in control. Not the new mayor, not the old governor, not this president, not the last president, not the next president, not your mommy, not your daddy, not your spouse, not your husband, not your wife, not your brother, not your boss, not the Illuminati. You are in control, comma, got it? Five words that will fundamentally change your life. No more Wa Wa. No more Wah Wah. Let's be honest in here with each other. Who here is a Wa Wa? I want you to own it and say it publicly. It will help you get it out. Get out. Get out your fucking bitches. You fucking crybaby. Who's a Wawa? If you're a Wawa, say I'm a Wawa. I'm a wow. Own it. No more complaining, no more crying. Stop it. No one's listening to you. Complaining and excuses are poison. And they're addicting. They're the heroine of emotions. They're bad. It's bad. Don't be a Wawa. No more Wawa. You are in control. You got a crappy job. That's on you. You took it, you're staying it. But Gary, I got bills. Figure out how to make money elsewhere. Get another job. Notice that, gentlemen, I said, what are you doing at night? Hanging and talking with my family. Great to have family time. But like, he's got little kids. They go to sleep. What are you doing ten to midnight? I know what I'm doing ten to midnight. I'm working a lot of times because I'm trying To build something. And then if I wake up and I'm like, wait a minute, I should spend more time with Mona or my kids or things of that nature. I'm not going to Wa Wa. I'm gonna change. Beautiful. I don't understand. What do you want from me? What, do you want me to enable you like your mom does? I'm not gonna enable you. It's 100% your fault. Everything you're upset about is 100% your fault. 100%. Is there systematic sexism and racism?

Gary Vaynerchuk (57:13)

Break up with the relationship today, right now. Break up with the relationship right now, right now. The breakup. That's the easiest one to move out. Your parents are enabling you. Move out. Live even more humbly and more crappy. Break up and get out. Break up and get out. Break up and get out. Break up and get out. Break up and get out. Break up and get out. Break up and get out. Break up and get out. That is a hundred percent what's right. When you're not happy, you have to change. We have tons of jobs available. Damien, go to vaynermedia.com, go to LinkedIn and look at Vayner. X Break up and get out. Break up. Yeah, I'm very bullish. General on esports. Break up and get out. Break up and get out. Break up and get out. I mean, if you know that you're in a dead end relationship, you gotta get out. Who's in a very bad relationship? Say bad relationship in the chat. Who's in a very bad relationship? Trains in love. Trains in love. Who's in a very bad relationship? Say bad relationship. Look at that whale. Toxic. I'm an enabler. I was for 10 years. Just got out. I got out. Sister needs to get out. You know, that's it, man. Get out. You can do it. The reason you're not getting out is you don't value yourself. You have low self esteem. I can tell you right now, you're amazing. I need everyone to understand this. This is a wild concept. This is sad. This is actually the saddest moment of the show. Ready, everyone? You are amazing. You're actually amazing. I need all of you to understand you're amazing. Yusuf says bad, but got kids. Your kids are getting more affected by you being in a bad relationship than you breaking up. It is very clear to many people at this point that people that stay in a bad relationship toxic are fighting or not showing love towards each other, are showing their kids more damage than if you got separated the old way. That you stay until they go to college actually showed that it screwed those kids up more. So you're either using the kids as an excuse or you didn't know. This is very important. All of you are amazing and most of you think you're not real. Talk. And I need like, please don't bull crap me. Just give me the number. If 10 is the greatest human on Earth and 0 is the worst, what, what do you judge yourself right now? Give me your number. Don't bullcrap me. Don't bull crap me. Give me the real, real number. Your real number. Your real number. Don't gaslight me. Don't. You know I need you to. I need your answers. You know, When I see that three, when I see that six. When I see that five. When I see that three, I see a lot of sevens, eights, nines. That makes me happy. But I need the people that put a three on themselves. That five. Deer thugs. You're not a five. Natalie, you're not a six. I'm telling you, you're not. You're a ten. Courtney in there, you're not a five. Dale, you're not a six. I'm telling you. You're not. Even if you're doing something horrible, even if you're beating your spouse, even if you're doing drugs, even if you're doing infidelity, even if you're stealing money from your job, you're just hurting right now. Show yourself, Grace. You're just hurting. And you've got to audit who you're spending time with and what you're listening to. And you've got to look at the patterns of your life and you've got to understand that you're able to get out of this. And if you hang out here for a long time and I'm going to be doing this a lot, who's excited that I'm going to be doing this a lot in 26? Put the number 26 in the chat if you're excited that I'm doing this a lot in 26. Yeah. Gene Darusha, I want to make you cry. I want to make you feel. Yeah. I'm telling you, we're gonna hang out here heavy in 2026. I'm gonna be on Tick Tock Live a lot in 2026. T with GaryVee Live pop up sessions. And I'm gonna be live on the road. Luckily, Train's a big dog. He's gonna have a backpack. Courtney will come out once in a while too, because she's excited about that crap. Listen to me. We're going to fix this for free.