Why Staying Too Long at the Wrong Job Kills Your Career | Tea with GaryVee Ep #82

Summary

Podcast Summary: The GaryVee Audio Experience

Episode: Why Staying Too Long at the Wrong Job Kills Your Career | Tea with GaryVee Ep #82

Date: August 28, 2025
Host: Gary Vaynerchuk ("GaryVee")

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Episode Overview

In this "Tea with GaryVee" episode, Gary dives deep into career stagnation, modern work expectations, entrepreneurship, navigating difficult work environments, personal resilience during hardship, and the power of community—through passionate Q&A with callers and the live chat. With characteristic candor, empathy, and humor, he unpacks the real reasons people stay in the wrong jobs and why letting go—or moving on—is essential for growth both professionally and personally.

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Key Discussion Points & Insights

1. Cutting Your Losses in the Wrong Job (00:02–01:51)

• Andrew (question): After 3 years at Walmart with no promotion, is it time to move on?
• Gary’s Advice:
  • Staying too long at the wrong place kills your momentum; getting new experience elsewhere is how you know if it’s truly the employer—or your own performance.
  • Multiple data points (e.g., working at Target, Five Below) clarify whether it’s the system or you; if it’s always the same, perhaps it’s the wrong career.
• Memorable Quote:
  • “People think putting a couple years into a job is cutting the loss. It's not cutting loss. You had an experience.” (GaryVee, 00:16)
  • “If you're over four, and every store says you suck... maybe retail is not your career. Maybe you need to be in camp counseling or a chef.” (GaryVee, 00:45)

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2. Finding Flexible Work as a Parent & Embracing Entrepreneurship (01:51–05:48)

• Allie (question): Stay-at-home mom needing a flexible, impactful job, feeling stuck.
• Gary’s Advice:
  • Modern expectations are at odds with reality: we “want more” (flexibility, time with kids, money) than prior generations.
  • Reality check: Not all companies can be flexible, and “asking for too much” is an honest part of today’s labor challenges.
  • Alternative: Become entrepreneurial—flip items on eBay, Facebook Marketplace, Whatnot. Anyone can learn to make extra income this way given time and commitment.
• Notable Timestamps:
  • Gary’s “asking for too much” segment: 02:08–04:07
  • Flipping as a solution: 04:28–05:48
• Highlighted Quote:
  • “My actual answer… is to buy shit at thrift stores... post on Facebook… sell shit on ebay. You can make $1,000 a month easy flipping, after three to four months of learning.” (GaryVee, 04:28)

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3. Online vs. Brick and Mortar for New Products (06:04–07:06)

• Caller: Should new brands prioritize physical stores or digital sales?
• Gary’s Advice:
  • Start online for traction and leverage; brick-and-mortar stores want proof (heat) from social and live shopping before they’ll stock products.
• Quotes:
  • “Get your leverage online first… They [retail chains] are looking for momentum in sales and heat from social.” (GaryVee, 06:26)

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4. Most Underrated Growth Tactics for Small Businesses (07:10–08:50)

• Question: What are small businesses overlooking in 2025?
• Gary’s Tips:
  • Live social shopping and IRL streaming (e.g., Twitch, Kick).
  • AI-powered content creation to scale without huge teams.
  • Local influencer marketing: Use Instagram search for your town, DM micro-influencers, and offer free product/services for posts.
• Quote:
  • “Every local business… should go on Instagram, search their town… find local influencers and DM them to collaborate.” (GaryVee, 07:19)

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5. Navigating a Narcissistic Boss (08:50–11:19)

• Question: How to handle a narcissistic boss if you love the job?
• Gary’s Insight:
  • "You don't love the job, because his job includes the narcissistic boss."
  • No unique jobs; look elsewhere for the same tasks with a better boss.
  • Personal branding (posting your expertise on LinkedIn, social media) creates future opportunities.
• Highlighted Quote:
  • “You do not love a job if you don’t love the boss. And if you’re using the word narcissistic, you’ve now done enough homework to understand what that is. A narcissist is a very tough human to interact with. It’s a non-winning game.” (GaryVee, 09:11)

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6. Grief, Work Ethic, & Being Honest at Work (11:19–14:23)

• PK (caller): Dealing with family illness and declining work productivity.
• Gary’s Guidance:
  • Grant yourself grace during grief; communicate openly with your employer about your situation.
  • Some need work for escape, others need time off—it's highly personal.
• Notable Moments:
  • Empathy and validation for taking a productivity hit during hard times.
  • The importance of not compounding stress by hiding one’s struggles at work.

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7. Regret and Starting Over (14:27–17:28)

• Question: Advice on missing windows (didn’t sell company at its peak), now restarting at 36.
• Gary’s Philosophy:
  • Don’t dwell on regrets; avoid starting from a negative, cynical place.
  • He’s made “a million mistakes” — forward motion is everything.
  • Sports analogy: Too many compare life to a game where they’re “down 14-9 in the first quarter and already crying.”
• Quote:
  • “Looking backwards is not good for your neck or your soul... Yesterday’s over. Learn from it and forget about it.” (GaryVee, 14:37)

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8. Teachers, AI, and Monetization Beyond the Classroom (17:32–21:51)

• Darian (high school teacher): Loves teaching AI to students, wants to monetize his knowledge.
• Gary’s Playbook:
  • “Teachers come in all shapes”: Monetize by building a brand outside the school system—live social/video teaching, courses, speaking, books.
  • Give away a massive amount of valuable content for free to grow community before selling anything.
• Memorable Advice:
  • “The classroom… is not the place to monetize for teachers. … If you’re asking me about monetization, you must live elsewhere.” (GaryVee, 19:30)
• Practical Tip:
  • Repurpose classroom content for short-form videos on TikTok/Instagram/YT to draw attention and create future monetization paths.

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9. Loneliness, Community & Trust (22:04–37:43)

• Damon (caller): Struggles with loneliness when distancing from negative circles, and when hustling with side gigs.
• Gary’s Deep Dive:
  • Distilling the difference between “limiting contact” (not cutting off) and seeking new, positive communities—be they in sports, fandom, religion, or hobbies.
  • Trust Issues: Many struggle to find or accept new supportive communities due to past trauma and trust issues.
  • The journey:
    1. Slowly reduce time with negative people (don’t sever family completely).
    2. Increase time and courage to connect with interest-based communities, both online and offline.
    3. Recognize that building trust is a muscle; practice and incremental growth are necessary.
  • Powerful Quote:
    • “Once you realize that no one’s better than you and that no human should be put on a pedestal, even the ones you most admire… then it really gets going.” (GaryVee, 33:56)
  • Action Step:
    • Damon shares his Instagram & Whatnot handles; Gary encourages the supportive VeeFriends/Whatnot community to connect—but only those who are "at their ultimate great place."

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10. Year-Round Business & Content for a Seasonal Industry (37:49–43:25)

• George: Runs a Christmas lighting installation business, wants to grow off-season.
• Gary’s Answer:
  • Create helpful, themed content all year (“Christmas lights in July?”) to build brand and client pipeline; people plan year-round.
  • Leverage the universal affection for holidays to create shareable, engaging content—there’s always an audience.
• Notable Advice:
  • “People love to plan, bro. People love to plan... Start making Christmas lighting content 365 days a year.” (GaryVee, 41:11)

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Notable Quotes, Moments & Lessons

• On Career Stagnation:
  “You need multiple data points. Some people are not being seen, and some people stink at their job. You don't know until you try.” (GaryVee, 00:34)
• On Modern Expectations:
  “We just want more. Our parents were willing to take an L in certain categories. We want more.” (GaryVee, 02:31)
• On Toxic Bosses:
  “A narcissist is a very tough human to interact with. It’s a non-winning game.” (GaryVee, 09:11)
• On Regret:
  “Yesterday’s over. Learn from it and forget about it. You cannot give weight to yesterday.” (GaryVee, 14:37)
• On Trust and Community:
  “Notice how no one disappoints me? I don’t put anyone above me. We are only disappointed by the ones we put above ourselves.” (GaryVee, 34:04)
• On Building Community:
  “This is a community that’s built on this foundational truth: strangers become acquaintances, acquaintances become friends, and friends become family. VeeFriends.” (GaryVee, 37:33)

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Timestamps for Key Segments

• Cutting Losses & Job Hopping: 00:02–01:51
• Flexible Work for Parents / Flipping Hustle: 01:51–05:48
• Online vs Brick-and-Mortar Sales: 06:04–07:06
• Underrated Small Biz Tactics (AI, Local Influence): 07:10–08:50
• How to Handle a Narcissistic Boss: 08:50–11:19
• Grief & Work Ethic: 11:19–14:23
• Regret & Restarting Career: 14:27–17:28
• Teachers Monetizing AI Knowledge: 17:32–21:51
• Loneliness, Trust, and Community: 22:04–37:43
• Year-Round Seasonal Business Content: 37:49–43:25

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In Gary's Own Words

The episode is classic Gary: direct, practical, and deeply empathetic—urging listeners to face hard truths, break stagnation, leverage new platforms, and above all, relentlessly build community and self-awareness. Whether you’re stuck in a job you hate, struggling with expectations, or building your own tribe, every answer is peppered with actionable strategies and real talk.

Signature GaryVee Tone:
“Love you, bro. That was real fuckin’ shit. Damon's life is forever changed. Not just because of me, but because of this community.” (43:00)

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Final Takeaway

If you're feeling stuck—whether in career, life, or community—the solution is movement: try something new, experiment, build your online presence, seek out like-minded people, and don’t let regret or self-limiting stories hold you back. And above all, remember: community is everything, but only you can take the first step.

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Transcript

[Gary Vee]

Let's get into the show. Aaron, what do you got on the first question?

[Aaron]

Okay, question from Andrew, 22 years old. What would be your advice to a three year Walmart associate who's having trouble promoting and moving up? I have the capability and experience but not the opportunity. Should I cut my losses and find somewhere else?

[Gary Vee]

Yes. You know, cutting losses is like, like I think this is a humongous issue for the world. Notice how he asked the question, should I cut my losses? People think putting a couple years into a job is cutting the loss. It's not cutting loss. You had an experience. You also don't know if you're right or they're right. A lot of employees love to shit on their bosses and their bosses bosses and saying not getting the opportunity. Meanwhile they might just suck. And him going to Target. Good news when you're at Walmart, Target is interested. Target's interested, bro. What's his name? Andrew. Go to fucking Target. Now. If Target after a year or two also says you suck, you should go to five below. And if five below says you suck or blow, well then guess what? Now you're over three. Three strikes you're out. At the old ball game, you need to rethink your whole fucking sitch. But if he's not getting the at bat in a Walmart store, A, there's like thousands of Walmart stores, B, there's other retailers and he needs to figure out if he's good or he's right, that he's not being seen. Some people are not being seen and some people stink at their job. And you don't know until you have multiple data points, you know, but like look, you've got to, you've got to respect if you go over four and every store says you suck, like you're going to have to eat it a little bit. And maybe, maybe retail is not your career. Maybe you need to be in camp counseling or you know, a chef. Let's get into the next question.

[Aaron]

Erin, from you, this question is from Allie. I'm currently a stay at home mom who is feeling financial pressure to work. I'm overwhelmed trying to find a job that helps me be a present ish parent to my toddler, have a flexible schedule and support my family financially. What do I do? I search and search and feel like I'm hitting dead ends.

[Gary Vee]

More searching. I mean like that's a lot to ask, you know. Again, we're in this new era. We need to understand this new era. Everyone's like, it's so hard now. It was so much better for our parents. It wasn't better for our parents. Our parents were willing to sacrifice time with kids to get the finances done. We want more. It's just the truth. Like are we are gang, Can I get all 1000 of you across all platforms to agree that we just want more? Like our fucking parents and our grandparents generation really were willing to take an L in certain categories. We want more. And companies are like, sorry, like again I keep saying this about businesses. They don't have the luxury of being just your family. They don't have the luxury of being bullshit like school. Like where it doesn't fucking ma. Like there's ramifications. Companies go out of business. Companies are gonna use AI. Companies are going to pick who their best employees are and they're gonna decide. Best is time put in or impact while time put. Let me be very transparent as a boss. I don't need any of my employees to work 100 hours a week for me to be like they're the best if they work. Let's just be even more direct. There are employees in all my companies that work 42 hours a week. But they're incredibly impactful in those 42 hours and I'm good and there's other employees that work 67 hours and people know me like hard work and all of that. But if they're not impactful, they're not as good. It's just real life. It's either impact or like some version of less impact but more hours put in. Like not all of us get the same output or impact on the time amount we spend. I can do a 15 minute meeting and really have financial impact. Most of the people that work for me cannot. That's just real life and that's just the game. So you know, here's a problem. The problem is we're asking for too much. We just are. Read that again. Slow.

[Aaron]

Okay. From Allie. I'm currently a stay at home mom who's feeling financial pressure to work. I'm overwhelmed trying to find a job that helps me to be a present. Ish. Parent to my toddler.

[Gary Vee]

Ish. She's being fair. I give her a lot of credit.

[Aaron]

Have a flexible schedule.

[Gary Vee]

Flexible schedule and support.

[Aaron]

Be present and support my family financially. What do I.

[Gary Vee]

This is where I think entrepreneurship and live selling can come in. My actual answer to her is to buy shit at thrift stores and garage sales and flea markets and look around the house for random stuff and post on Facebook and look at Facebook Marketplace and sell shit on ebay. And whatnot. How about that? How about that curve ball when we're asking. The reason she's looking and looking and looking is companies don't want her. They're like, they're not. And by the way, there are hundreds of thousands of companies that would want someone. But it sounds like the schedule has to be a flexible way. That doesn't work for a lot of companies. It's just real life. Hopefully she can find something. And I hope, like, you know, but like, a lot of, like, my dad's liquor store can't be flexible with ours. It's retail. It's open. It, like, needs, like, you know, like, I don't know, like. So I like the idea of taking things in your own hand and buying and flipping. And I think she can make 1000 bucks a month easy flipping. I think everyone can make $1,000 a month easy, easy. After three to four months of really learning, right? Really being on ebay, understanding what's worth money, really going to the thrift store every day, you know, really, really, really, really going there. Garage selling, like, you know, like, really learning flipping, you know. So that's my answer to that. Gatsby Global. What's good?

[Caller 1]

Hey, Gary. How are you?

[Gary Vee]

I'm well, brother. Are you a Bears fan or is that just a hat?

[Caller 1]

It is a Cincinnati Reds hat.

[Gary Vee]

Oh, you're right. I'm getting rusty. Are you a Reds fan or big time? How old are you?

[Caller 1]

32.

[Gary Vee]

Love it. All right, brother, go ahead.

[Caller 1]

In a day where of course social shopping is on the rise and of course you're crushing it on whatnot, IG live you can utilize, of course, TikTok shop. Should we still try to utilize actual brick and mortar stores too, for new products and new ip, or should we try to lean in?

[Gary Vee]

Lean in on online first. Get your leverage online first. When you say lean into brick and mortar, are you saying you made a product and you're hoping Walmart or Albertsons or Marshalls will carry it? I would say the way those stores are making their decisions now is they are looking for momentum in sales and heat from social and live shops. And then they bring the stuff in. They're trying to guess less themselves. It's much better for Walmart and Claire's and 5 below and 711 to know already there's demand than to guess. So you'll have more leverage by building heat online. Cool. All right. You got you, brother. Good luck.

[Caller 1]

See ya.

[Gary Vee]

See ya. I like that shelf. All right, Aaron, you're up.

[Aaron]

Okay. This question is from Andreas Gary, what's on? What's one underrated platform or tactic that small businesses aren't using enough to grow in 2025?

[Gary Vee]

Live social shopping, IRL streaming, twitch kick. That whole game. AI learning to be able to make much more content easier without having a million dollar team. Small businesses, if you have a physical store starting to actually live sell from your store even during store hours so people can see you're doing it. Even shoppers coming in. Local influencer marketing. Every local business on earth, every local business on earth that sells something should go to Instagram, search their town at the top of the screen, right? Like let me. Here we go. Can you get my screen? Here we go. Every single business on earth should go to the top of their screen. And like if you're on Instagram and put Newton, Mass. Right, you're putting Newton, Massachusetts right. That's what I just did. It's a little hard to see. I but I just typed in Ace town and then results pop up, right? And you can put like, you know, literally results from that area. And so this photo's from there and you look at all of them and you figure out who influencers are locally, who live locally and do micro influencer deal with local celebrities. You know, if you're a pizza shop, you just DM13 people that post. You can look up the accounts that show up in your general area. You see somebody that lives lives in Newton, Mass. Has 13,000 followers, you DM that person be like, I want to give you free food, come in and post and tag because they're local and there's a little bit of a local element to that. So there's just so many things you can do, so many tactics. All right, next question here.

[Aaron]

Okay, this question is from Ryan. How do I navigate a narcissistic boss when I love the job?

[Gary Vee]

That's hard. You don't love the job cause his job includes the narcissistic boss. You love the tangible parts of the job. There's no job on earth that there isn't other jobs like that. With at least a more neutral or remarkable boss, people have to quit more. I don't know. People need to spend time on LinkedIn posting content and creating opportunities. Again, I mentioned it yesterday. Cause I'm really just giving her love. Court Courtney's posting all this good content on how to help beginners start live streaming obs all that potentially leads to opportunities. I want Courtney to like her job because I want her here. But I get excited when people do content because I know it opens up opportunities. And by the way, she might be dreaming of living in Barcelona. She's a young woman once in her life and she could get an actual message from somebody in Barcelona saying, hey, I've seen your videos on this. I want to start doing live streaming. I want to do this right. We all remember Dustin used to work here. Dustin Lee used to work here. Remember Dustin Braden? Remember that dude? Like, he's. He's not here anymore. Right? Because him being associated and building brand through me led to a very high net worth boss in Arizona who wants to have similar outcomes to my career. Like whether you get it through the shine of association with a person or you create it for yourself like Courtney's doing, or a combination of the two. Two people need to start putting out more content about their skills and knowledge and passion to lead to opportunity. Or if they don't want to do that because they're weird and nervous about it, they're weird about it. They're not weird. They need to start dming and applying to more jobs if they're unhappy. You do not love a job if you don't love the boss. And if you're using the word narcissistic, you've now done enough homework to understand what that is. A narcissist is a. A very tough human to interact with. It's a very substantial human flaw. It's a really tough thing to navigate. It's a non winning game. It's like all four walls are blocked in. And that person needs a lot of therapy and like a lot of work. So if she or he. What was it, Ryan? If he's figured out that truth. That's rough. Man like that to me is really worth looking for some other opportunities. So.

[PK]

Paul, Gary, how are you?

[Gary Vee]

I'm quite well. It's lovely to see you, PK here. It's great to see you, pk.

[PK]

I have a personal question. It's tough to ask. My mother's recently been diagnosed with kind of between stage three and four lung cancer, unfortunately.

[Gary Vee]

I'm so sorry, pk.

[PK]

No, that's okay. Thank you. My question is I feel like my work ethic at work is struggling as.

[Gary Vee]

It should, like grieving. Grieving. I can tell you right now, brother, you know where I sit on work ethic. Because, you know, I know you've been around these parts for a bit, brother. I'm on the record that when those unfortunate days happen in my life, I will be a shell of myself from a productivity standpoint.

[Damon]

Right.

[Gary Vee]

We must become much more gracious to ourselves of times of grief.

[PK]

It's a little ironic because I have the gracious grizzly bear, right?

[Gary Vee]

You've got to be gracious to yourself, your brother. Like you're. You're allowed that now. Now I own my own businesses and when I, when I'm less productive during those devastating chapters in my life, my business is just going to feel the effects. But no one can quote, unquote, fire me, right? You've got to balance a little bit of like making sure you're over communicating with your place of work to make sure you're not putting it. Because I've had unbelievable amounts of people DM me unfortunately who've been let go in this situation because it's been too prolonged for their boss's subjective opinion of what they're willing to be gracious about. And so you don't want to double compound your worries. So make sure you're a good communicator and honest with your job.

[PK]

That's the thing. I've kind of been keeping it close to my chest. I haven't really divulged much to my work yet. Just because there's a lot of unknown right now, just kind of going through treatment. Do you think I should be more.

[Gary Vee]

How do you. How do you. Let's talk it through. I want to make this valuable for everyone. How good do you feel about the humanity and kindness and graciousness of your organization or bosses or managers? Or bosses. Boss.

[PK]

Yeah. I mean they are very understanding. I know that they.

[Gary Vee]

How long have you worked there?

[PK]

10 years this year.

[Gary Vee]

Okay. I think you're in a great spot, brother. I think you go have a real combo and again, you only know if you like. Look, there's a lot of people who grief who actually need to be at work. It's escape, of course. Of course. There's been people who I've given time to that have come back three days later and said, Gary, you're the best. But I'm back because like these last three days were actually the worst and I actually need, even though I might be running at 65%, I need to be here. So, you know, you just gotta figure out, you know, what works for you. But 10 years, the way you just responded to me, you've built equity, you seem to feel like it's not a cold hearted organization. I think you need to go and have a proper combo, brother.

[PK]

Okay. I appreciate you, Gary, as always.

[Gary Vee]

I'm sending you a lot of love and prayers. Pk. Love having you part of this community. Love you, bro.

[PK]

Appreciate it, Gary.

[Gary Vee]

Love you. Take care. My man. All right, Aaron, let's keep this rocking and rolling.

[Aaron]

Okay? This is a question from the chat. Actually. I was successful with my company, but didn't sell when things were good. Now I'm 36 and starting over. Any advice on regrets and starting again?

[Gary Vee]

Looking backwards is not good for your neck or your soul. That is my advice. Aaron, I've made a million mistakes. Not 10, not 40. I've made so many mistakes, it's like laughable because I have so much opportunity in the last 10 years. Last night I was in dinner with some people and the kid is the founder of Mad Happy, the brand, you know, that ripping hot, iconically epic fashion brand that makes a fuckload of money. He reminded me nicely that I passed on investing, you know, like, like, like I only make mistakes. In fact, I would argue that my life up to this point is predominantly massive amounts of mistakes with a couple of occasional good decisions. And I love it. I don't know what else is I do not understand on the collecting capacity of especially youth right now. Youth has gotten so good at being critical on themselves. Five seconds into the game, using a sports analogy, the amount of children under the age of 37 on this earth that have started to dwell in a game of life similar to a game of basketball where the score is 14 to 9 in a four quarter NBA game and they're crying because they're down 14 to 9 is staggering. So if you follow basketball and you understand my analogy right now, you need to wake the fuck up and understand how real what I just said is. I don't give a fuck that he missed it. I missed everything. What are you gonna do? What's he gonna do, cry? What's he gonna do? Go on a random live stream and ask some guy he admires what he should do? It's over, Sid. That's it. There's no fucking time machines. Get over it. Because, and here's why. Not because I'm a dick or like trying to give tough love. Because we have no because, bro. We have no choice. You have no choice. Why? How? Coming from a place of regret, cynicism, disappointment is such a bad way to start a sentence. Coming from a place of offense where you want to learn and build on top of why and how are remarkable. Using why and how from a place of regret is the poison in society. Yesterday's over. Learn from it and forget about it. You cannot give weight to yesterday. Yesterday. You, yesterday. Yo, yesterday. Go yourself, Alan K. What's good, bro?

[Darian]

Hey, I'm just calling up. Glad to be on here, finally get to talk to you.

[Gary Vee]

It's a pleasure, man. First, the. The beard mustache combo is epic, bro. The Raleigh fingers is coming in, my man.

[Darian]

Right, right. I'm bringing it back. I'm bringing it back.

[Gary Vee]

I love it.

[Darian]

I'm a high school teacher and I have a new social media marketing class that I'm putting together and you know, I'm getting the best information.

[Gary Vee]

I love it. Thank you.

[Darian]

Get the kids updated.

[Gary Vee]

Thank you.

[Darian]

And I'm, you know, so I'm using your info. I love AI. I'm all about it. Once it came out, I'm doing everything with AI. I even wrote a book for teachers on how to use AI Love. And they. The problem is a lot of teachers don't want to use AI. Right. They don't want their kids to use the students. And I'm the opposite. I'm against the American education system even though I'm in it.

[Gary Vee]

Yep.

[Darian]

I tried to try making like chatbots for my students and you know, to help them study and do everything. And I love doing, you know, AI engineering. Right. The prompt engineering. The problem I have now is I'm a teacher. I'm passionate about it. I love helping, you know, teenage kids find their passion and do what they need to do. I just don't know how to turn that into another income where, you know, it's hard to keep kids attention while they're in my forced to be in my classroom, let alone get them interested in what I have to say, you know, on their own. I would like to like to turn it into my own like way of making extra income.

[Gary Vee]

I got it, brother. I'm a teacher too. I just don't do it in a classroom in an archaic system. I do it in the entrepreneurial arena of live social and social media content. You should do that at scale and that will lead to income opportunities of speaking, book writing to get paid on that courses and many other things. The classroom in the academic, corporate structure of government is not the place to monetize for teachers. It's a place to scratch an itch. I admire the fuck out of teachers. It's a destiny and a home for a lot of people. My sister taught first grade for a long time. I believe teachers are massive, but teachers come in all shapes and sizes. Some are in classrooms and some live in other places. If you're asking me a question of monetization, you must live elsewhere.

[Darian]

Okay, so see, I was looking at the whatnot, right? And I was like okay, what if I did something like you're doing right now, but what the hell am I gonna sell? Like, there's also a book, but I'm saying if my attention would be more to, like, the student and kids ain't reading no books today.

[Gary Vee]

I understand.

[Darian]

So I hate reading books too. I mean, to be honest with you, but.

[Gary Vee]

But why should a kid buy anything from you, whether it's a book or an online course, when there's 8 trillion things of information for free?

[Darian]

Exactly. That's what I'm saying. So, like, I don't.

[Gary Vee]

So rule number one, sell something people want.

[Damon]

Okay.

[Gary Vee]

Well, how do you get people to want your book? Because I sell millions of books, even though I put out the information for free, it's by putting out so much content for free and bringing so much value, brother. Do you know why so many people collect v friends like they collect vee friends now? Because they want to really support me on this journey. And then they fall in love with genuine giraffe and patient pig. And so, Alan, that's the punchline. You got to figure out what you can actually sell. But I think that before you worry about, like, what, I think you putting out a ton of information for free about what you know about AI on social media and live stream sessions will start to build a community which then will have monetizable value.

[Darian]

I put the videos I'm making for my social media class. I actually put them on YouTube. So hopefully.

[Gary Vee]

Yeah, but that's not a read day. Trading attention, you know, in that purple book you just hung, literally just held up, you know, that I would on you if you just put it up the video on YouTube. I need you. What I'm saying is I put it.

[Darian]

On there because I want teachers to.

[Gary Vee]

I get it.

[Darian]

To make their life easier just to use my.

[Gary Vee]

My video that I love that you're watching wonderful for. But if you want to actually turn your world into monetization, you got to clip the out of that. Put it on Tick tock, Instagram, Snapchat, YouTube, LinkedIn, Facebook, Twitter. Like, read the book and live the book.

[Darian]

I know. Okay. All right, man.

[Gary Vee]

All right, man. Love you, man. Stay well. Darian.

[Damon]

Yep.

[Gary Vee]

How are you, brother? Pleasure.

[Damon]

Well, thanks. How are you?

[Gary Vee]

Good, man. Where are you from?

[Damon]

Pennsylvania.

[Gary Vee]

Nice. Great to see you.

[Damon]

Yeah, you as well, man. Thank you for taking the call.

[Gary Vee]

Of course.

[Damon]

Wanted to connect on more of a human level.

[Gary Vee]

Please.

[Damon]

So there's a lot of messaging out there that if your circle isn't energizing you, motivating you Supporting you, making you a victim or playing the victim themselves. You should shorten that circle.

[Gary Vee]

Yes.

[Damon]

And make your network the people that are really energizing you and giving you the support you need.

[Gary Vee]

Yes.

[Damon]

Then there's a lot of messaging out there that sounds to take your grind into your own hands and, and make your own pathway and blaze your own path, pathway in the world. Both of those scenarios bring a lot of loneliness and you yourself find yourself alone many nights.

[Gary Vee]

Let's, let's talk. Let's, let's talk it out. The first part, the first part that you brought out, brother. There's often when it's well said, there's a second part to that sentence that has a comma in it that says and then go find people who bring you good vibes and good energy.

[Damon]

Right.

[Gary Vee]

Let me explain to you veefriends, my little universe. One of the reasons it's going so well doesn't have to do with how good of an entrepreneur I am and how well I'm operating. It's that a lot of people in the veefriends community have literally found their best friends in the world by being joint collectors of this. If you go look at Comic Con, if you go look at a sporting event, if you go look at like, you know, all these things, people find things around circumstances, similar interests that have a more. And what I'm trying to do with be friends is bring a more positive vibe. I take what you're saying and it is valid. You're right. I do think the first thing, which is limit your interactions, not cut completely out. Because a lot of times, as you know, these are your best friends or your parents or your siblings. I'm not a big advocate of like never talk to your mom or brother again, but I am a big advocate of protecting your sanity when you have deep negativity around you. And maybe you don't talk three times a day, maybe you talk once every three days. Right? Right. And I do believe it is on all of us that we have the ability to get out of our loneliness. But we must find our communities, whether in interest, in discord, in fortnite groups, what you know, chess clubs, book clubs, you know, I will say please.

[Damon]

Whatnot itself a little plug for whatnot. I have met several individuals that I met through the app and then went and visited them and we hung out, we grabbed drinks and had dinner. And it is a very connective community and you can find long term friends in communities like the hobby and virtual communities like whatnot. So 100% agree.

[Gary Vee]

Do you feel like there's an opportunity for you brother to double down and quadruple down? Like, hearing your question, sensing your energy, really excited about this conversation. I appreciate the vulnerability and the thoughtfulness because it's an important conversation. Do you believe that there's an opportunity for you to quadruple down on some of the things you're finding in whatnot or other places that are showing you previews or are flirting with the ability to create a network of a dozen or so really positive friends? Do you think there's an opportunity there?

[Damon]

There absolutely is. And there absolutely is an opportunity to connect more with individuals.

[Gary Vee]

Robbie, Rob, congrats on your streams as well.

[Damon]

100%. Everyone has that opportunity. The second part of the coin, I think, is, you know, when you have a 9 to 5 and then a 5 to 12, you know, you don't have the opportunity to make space in the physical world with your friends that are here. And so that, that in and of itself also creates a space of loneliness where, yes, the, the digital community can feel part of that, but doesn't fill the whole.

[Gary Vee]

Yeah, I mean, I think if you're personally feeling that, my brother, I would say that you are not allowed then Monday through Friday to do 5 to 12. And you're going to have to force yourself to give up one of those 5-12s on every Tuesday or every other Thursday. Right. Like, I think that's going to be, again, really doubling down, really attacking. Like when you have this level of thoughtfulness and self awareness and clarity that you're communicating with me on, I think it becomes the game of jumping into the pool. Right. Meaning when I hear that that's also valid. That sounds very clear to me. And if you were my best friend in the world and we were having, which is kind of how I'm treating this conversation right now, I would say to you, brother, you've got to pick every Wednesday and fuck 5 to 12. And you're going to have to join the Bull Bowling Club, the pool club. You need to keep pounding and finding more people in the general Pennsylvania area within an hour drive. Whatever you're missing that it's clear that you're searching for.

[Damon]

Yeah, yeah, makes sense.

[Gary Vee]

Keep going because I'm enjoying. I actually think you're bringing a lot of value. What of what we've talked about right now feels right or feels like. Yes, Gary, I get that logically, but in my tummy right now, I don't feel like that's right.

[Damon]

No, I think your perspective of taking a Day off and using that day to be social and to go out and find something in the local community that is physical and something that you can create, you know, in person networks with. I think that's completely valid. One of the things I've tried to do more is try to get more connected with my church. And so that's.

[Gary Vee]

That's. By the way, brother, you're going down a very good path. I think for a people of lot in the last 40 years, the loss of community, as people started to go to their place of choice of worship on every Sunday, was such a grounding, such a great community that a lot of people have lost. In fact, you know, it's funny, I go to church on Sundays in the fall and winter as well. It's called MetLife Stadium. Right. I genuinely. And I mean, this. My community of JET friends, right. Of New York. JET friends is a real community for me. In fact, it's very church like. We go there and we talk about our sins of ever picking this team as our favorite team. We talk about the adversities of life, you know, like rooting for the Jets. Here's a great jets fan walking by me right now, Alan Harker, part of that community. Like, this is why I'm such a big fan of sports, by the way. Especially when you're a fanatic, it starts to you be. And you are religious about it. You build an incredible sense of community. And so a actual religious, like institutions, I'm pumped that you're leaning into that. And I think a lot of people, synagogue, church, mausoleums, like, you know, you know, whatever their place of preference and religion is, is a great thing to do. And in general, I think also finding, you know, that's obviously one form of community I really do think interests, you know, like, actually, let's go a little bit deeper. What are some. Are you into movies? Are you into sports? Are you into cooking? Golf? Like, what are some of your interests or things you're into or watch on TV or like, give me. Give me a little more color commentary here.

[Damon]

Yeah, I don't watch a lot of actual series on tv. I am big into anime. I do play a little bit of video games. Golf, I do.

[Gary Vee]

It's great.

[Damon]

Also, I sell sports cards here on whatnot and also in local card shows. So also, let me ask you.

[Gary Vee]

Let me ask you a deep question. Let me ask you a deep question.

[Damon]

Yeah.

[Gary Vee]

Do you trust people? Not always. Yeah, that's why I'm enjoying this right now. I'm really excited about this brother. I'm really happy you and I are together. Notice how that like that was a maybe for some people watching right now in my team, that was like a left field question. But notice how I went there and how good this feels for me right now. And I would have bet all of it on you answering that way. I'm very fortunate. I have two very opposite parents. One of them trusts everyone until they give them a reason not to. And usually it takes her a lot of reasons for her to lose that trust. I was fortunate enough to get that DNA and also be fundamental mentally parented by that person. The other parent trusts no one. And even when someone gives them years of good reason to fully trust, he is not capable of trusting them and is always waiting for the other shoe to fall and is actually searching almost often manifesting and creating some weird non truthful justification to lose the trust. I would tell you that this is the path I want you to look through because you are doing a lot of great things in the first part of how we address the issue that we're talking about. It's the second part that's actually the punchline of the conversation you and I are having. Your DNA and your circumstances of growing up and the things that happen in life have put you in a place where it's a little harder to trust. And that is leaning and leading to why we're in this predicament. And I will tell you if this is any solace and you're gonna have to go on your journey and I'd love for you to hang out more with us. And good news, you're catching me at a great time in my career. Starting in October, I'm gonna be doing tea with Gary Vee and a night version of this.

[Damon]

Okay.

[Gary Vee]

I'm actually contemplating cutting out alcohol permanently. So the winding down with Gary Vee things a little tough. Though I might do a non alcoholic wine brand deal that could be a whole thing in itself. I might start a brand again. Anyway, nonetheless, I really like you to hang out a little bit with us, brother. Because let me say one thing about this crew. There's a lot of people in here that I've gotten to know over the last four or five years that are incredibly worthy of your trust. And I already feel like I have a good sense that they quote unquote, let you down. And like anything in life, it becomes practice once you get three to four relationships where you get sustained two years where you it maybe was uncomfortable to trust, but they've done nothing to break that trust. And you're starting to get more. And you're starting to get more comfortable. You'll then become stronger in being able to open up and trust. And then you'll become so strong that even when someone does fuck you up, right. And breaks your trust, it won't be a devastating knockout blow. It will just be a tough punch and you'll, like, wipe the blood off and move forward. That's what we need to build up.

[Damon]

Yeah, absolutely. Absolutely. And that makes total sense. I think you're spot on in terms of your analysis where I do have trust issues from trauma in the past, and everyone does.

[Gary Vee]

And by the way, it's good news, brother. It's incredibly valid. It's appropriate because there's me not having trust issues, and you having trust issues does not not make me better or more capable or more awesome. It's literally circumstantial. The fact that you have the strength to go on here, publicly talk about this, put yourself out, means your brother. You're 90% of the way there. People that are able to do what you're doing right now, which is incredibly rare when they're feeling it. Most people that are in the exact predicament you're in are deflecting, blaming, and definitely not putting it out there.

[Damon]

Yeah.

[Gary Vee]

Right. And so I'm incredibly proud of you. I'm. I'm very. I admire it quite a bit, to be honest. I'm glad I went with my intuition and kept this call because I think not only are you starting to help yourself, I genuinely believe in the thousands of people that are watching right now. Like, literally, there's somebody who's literally you right now on whatnot, who's literally benefited from these 7 to 10 minutes and are on their way. And, man, I think it's. I think you. I think you can do this, man. I've watched people. I've watched some people not be able to get there. Ones that I love deeply and I wish they could get further, but I've seen some of those people, including my father, get much further along. And I've watched people who actually. It's time, brother. Yes.

[Damon]

And getting into the. The groove of meeting people and then finding that they are supportive and then finding that you can trust and let me.

[Gary Vee]

And like. And let me take it. Let me take you to step three.

[Damon]

Yeah.

[Gary Vee]

Once you realize that no one's better than you and that no human should be put on a pedestal, even the ones you most admire.

[Damon]

Yeah.

[Gary Vee]

Then it really gets going. The reason no one disappoints me is that I don't put anyone above me. We are only disappointed by ones that we put above ourselves.

[Damon]

Yeah. Yeah. I mean, and that's, that's, you know, a life of service. You know, you put people in front of yourself.

[Gary Vee]

By the way. By the way, I'm obsessed with life of service. I would argue that I give more than I take to everybody I ever meet. That has nothing to do with my ability to not put their subjective opinions about me at a higher pedestal than the subjective opinions I have about my own self.

[Damon]

Correct? Correct. Absolutely. Absolutely no. Appreciate this conversation, Gary. I thank you for all your advice and support as always. I really do hope there are others on the line.

[Gary Vee]

Oh, I got a couple good ones for you. There's a. There's a guy in the chat named the Dalton Tice that you absolutely immediately have to get connected with, who's very much leaned into his faith and is a great kid and also has ripped off a bunch of people at the National Sports Card Collection a couple years ago to own a tremendous rare robot first sticker rookie card collection. And I appreciate, even though he loves God very much, his entrepreneurial spirit shined through so heavy and he dominated and fucking ripped off the faces of, of children and the unknowing at Chicago a couple years ago to build a dominant financial force of opportunity for himself.

[Damon]

Oh my gosh. Love it.

[Gary Vee]

And I will say there's a lot of people. Michelle, everybody. Brother, what is your Instagram and what is your. Can people see his what? No, they can't see his whatnot here because he's not on his whatnot. What's your whatnot? Instagram. I want to. But if you were a great person in the veefriends community and a lot of you are, are not. So please do not DM this nice man because that is not what we're doing. A lot of you are not at your ultimate great place. Some people are work in progress. Unless you are at your ultimate great place where you are 100% well intended in your outreach to this wonderful gentleman. Please do not DM him. If you are fully there. Hi. Anthony would be at the top of my list. Please DM this person, this great friend, Damian. Damian. Where can people find you on Instagram and whatnot so they can DM you?

[Damon]

Hobbycast, H O B B Y underscore C A S T on whatnot. Hobbycast sports. All one word on Instagram.

[Gary Vee]

All right, so for everybody in West West West Jersey or that General Allentown, Bethlehem, Pennsylvania, there's a Lot of people in the general area. A lot of people are hitting you up. You are about to get a really good community of friends, my friend. But you. This is not them stepping up for you. This is. This is you stepping up and having the courage to be disappointed and really working on. Do not put them on a pedestal. No one. No one.

[Damon]

Yeah, absolutely. Absolutely. Thank you so much, Gary.

[Gary Vee]

Very much.

[Damon]

Appreciate the time.

[Gary Vee]

Of course, my friend. Have the best day.

[Damon]

You too.

[Gary Vee]

That's gonna be a nice message for this crew and a good clip for a lot of people. I hope millions of people watch that over the next 10 years. Cause I think there was a lot there. Everybody, how do we feel about that? That felt like that's. We're gonna get some of the. Those. That's what the fall and winter of 25, we're gonna get. That's what. That's. That right. There was real fucking shit that. Right? Like, I genuinely believe Damon's life's forever changed. And by the way, not because I did a nice job there, because I think I did do a nice job, but because of this incredible everybody. If you're new to veefriends, this is not just a Pokemon marvel thing. This is not just a big business that I'm trying to build. Both are true. This is a community that is built on this foundational truth, which is strangers become acquaintances. Acquaintances become friends, and friends become family. Be friends. And if you're in the whatnot chat right now and you've become part of that family, if you're in that journey or if you can communicate to everyone. Delgado. What's good, George?

[George]

Gary.

[Gary Vee]

Vee. What's up, bro? What's up, my man?

[George]

Oh, man, thank you so much for. For your time, man. And I appreciate everything that you've done. And, you know, I've been following you for, like, 10 years.

[Gary Vee]

Thank you, brother.

[George]

Oh, my gosh. And I just started recently following you again back to back for two months. And thank you.

[Gary Vee]

You missed me, right? I'm good. When people. I've been around for so long that people lapsed. Do you know I fucked up years ago when I was like, stop listening to me. Like, never listen to me again and go do your shit every day, people are like, I don't listen to you anymore. I'm like, did you do this shit? They're like, no. I'm like, wait, so you didn't do the shit and you stopped listening to the one positive fucking voice in your head? What the fuck? Anyway, I love when people come back after they Lapse for a while because they're like, oh, okay, I got it, Gary. Or this is annoying or whatever, you know, NFTs or be friends or garage sales or whatever. The. They're out. But when they come back, they remember what the truth is.

[George]

Oh, yeah. Hell yeah. But I appreciate you, man. So real quick. So I do multiple things. I. I love the thrill of selling, providing quality for customers and, and customer service products, all that. So currently I do. I do Christmas lighting during the off season. Christmas Christmas lighting installation. I'm kind of curious on how to build a Christmas lighting business on the.

[Gary Vee]

Off season by making content around it. Now, I would literally make videos of you talking about tips and tricks, how you think about it, things you've seen while you're literally in the summer putting up Christmas lights on your own home. That is the video you are literally. Because that in itself is going to capture people in their feed. If I see right now a thumbnail or the screen preview of you hanging Christmas lights and it says Christmas lights in July, question mark, like that's going to get. Do you know, brother, people with Christmas heavy.

[George]

Oh, yeah.

[Gary Vee]

People love themselves some. There's people that live for just Christmas. Like their, their super bowl is Christmas. Yes. And Dalton says hi. I wonder why. Dalton, I'm not saying for the right reasons, like, you. Where it's like, you know, the fucking Christ shit, the good stuff. I'm talking, they just love the holidays and presents and fucking Rudolph the fucking Reindeer and they fucking love Frosty the fucking Snowman and they can't wait to go to New York and see the fucking tree. And like, you know, they're fucking about Christmas. They fucking like the food and like, they like kind of not working for two weeks at the end of the year. And they like Christmas, the commercial shit, the bad stuff and good stuff. So, bro, Christmas works 24. 7.

[George]

Gotcha. So continuously put on content, just like you always say.

[Gary Vee]

Correct. Because when someone sees it on August 9th and they love your beard and they love your spirit and you've got a warm spirit, they're going to DM you and be like, yo, can you? Can I? Can. I like, people don't just. Of course there's people that buy when it's timely and then there's people that buy ahead of times. People love to plan. I don't. But some people get off. Like, do you know that people are playing planning right now their vacation next summer? There are people right now in the world doing research and shit on hotels.com and being like, I'm gonna go to Ibiza next summer. People love, bro. People love to plan, bro.

[George]

That's awesome.

[Gary Vee]

And like planning for who's gonna install their Christmas lights. Now you're doing a fucking. You're giving a fucking gift to people, Stefan. No, it is not possible to tip me. I do not accept tips here. The way you can tip me is by becoming a collector of vee friends. I am building the next Pokemon marvel. Go into the shop and buy v friends thing and learn this world. Go to ebay, type in veefriends, go to completed items. You will be blown away. What we're building here, George, that's what you need to do. You need to start making Christmas content. Christmas lighting content 365 days a year.

[George]

Got it?

[Gary Vee]

I mean, I would post on New Year's Day 2026 and be like, book your Christmas lights insta. You motherfuckers haven't even taken down your Christmas lights. And I want you to book me for next year. And there's somebody who will book you. Right on. Do you take Christmas light lights down? Yes. Oh, that during January, brother. All day you should pound. I mean, that's the. That's the good right there. That's the business. That's the business, people. Because some people love the spirit of like, you know, like I talked about yesterday. I don't know if you're watching like the guy who loves to drink some bud light and lawn. Do the lawnmower. There's the same people really like the Christmas lights thing. They're not Chevy Chase. They like it or they are Chubby Chase. Depends how you analyze that scene. But like, you know, like. But taking it down. Nobody wants to do that.

[George]

Yeah, it's. It's. And I've had calls, people saying, hey, my company never called back. And things like that. And I'm like, I'd be happy to be out there. And I've. I've even helped some people for free. Like right next door.

[Gary Vee]

Like, of course, cuz.

[Damon]

You're a good dude.

[George]

Might as well take it down, bro.

[Gary Vee]

I know people who keep Christmas lights up 12 months a year because they don't want to take them down. I'm. I'm being dead serious. I know two people. Literally, it's our second homes, so there's a little bit of that.

[George]

But hey, so. So I still have one Christmas light piece in my house that I. That I still have lit up. So no joke on that.

[Gary Vee]

Hey, Chad, who's a sicko and loves to take down Christmas lights, put sicko in the chat. Say sicko. You're a sicko. You like, Love it. Like you can't wait to take down the Christmas light lights. There we go. There's a couple. George. 24 7, bro.

[George]

You got it.

[Gary Vee]

All right, everybody, I am out of here. I love you. I hope you enjoyed love. You all have the best day.