5 Things You Need to Hear Before Going Back to School

21 Aug 2026 · 18 min · 7 chapters

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In short

Gary Vee’s “5 Things You Need to Hear Before Going Back to School” argues that school is not the only path to success, college can be a “racket” (especially debt), and students should use the next 5 years to explore and build self-awareness. He also stresses confronting parents’ expectations and stopping complaining/dwelling.

Guest backgrounds

No recurring guests are interviewed; the episode includes call-in clips with named participants: Nate (a 23-year-old discussing telling parents about an 18-month exploration plan) and Kiara (17, planning university options; parents pay). “Richard” is the caller asking Gary to advise Kiara.

Key claims

Don’t collect college debt to become a businessperson; entrepreneurship can’t be “taught” via a defined path; parents often respond to their upbringing, so have a direct, loving but firm conversation; dwelling/crying/complaining won’t change reality—own your fear and act.

Notable examples

Nate is coached to ask for 18 months, reassure parents, and promise to work if no traction; Kiara is advised to avoid high-cost debt, consume practical online marketing content, and treat university as a strategy rather than a guarantee.

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

Chapters

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Gary's School Experience and Perspective

0:25 to 2:15

Gary shares his challenging experience with school and societal expectations.

“Like I was a very happy kid but I hated school.”

The Racket of College Education

2:15 to 2:46

Gary discusses the pitfalls of college education and debt.

“I fully, fully, 100 ,000 % with no hedge do not believe that you can teach entrepreneurship.”

Navigating Parental Expectations

2:46 to 3:33

Gary offers advice on how to handle conversations with parents regarding life choices.

“not because it's the secret or because the world's so zen because it's fucking hard as shit out there.”

A Role-Playing Conversation

3:33 to 8:19

Gary role-plays a conversation to help a caller communicate with his parents about his future.

“How do I just, like, how do I tell my parents, like, I just want to go do for 18 months and I've been sketching out, like, all these of, like, just go do and explore.”

Advice for Kiara on University Choices

8:19 to 12:25

Gary provides guidance for a caller's daughter regarding her university decisions.

“Hey everybody, I hope you're enjoying the podcast right now.”

Mindset for Success During School Years

12:25 to 14:01

Gary emphasizes the importance of mindset and self-awareness during school.

“You forgot you don't want to deal in reality.”

Embracing Self-Awareness and Success

14:01 to 18:12

Learn how self-awareness and eliminating fear of failure can lead to success.

“People are asking all sorts of questions.”
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Transcript

Automatic transcript. May contain errors.

0:00Welcome to the Gary Vee Audio Experience. My name is Courtney Connect from Team Gary and in today's episode you'll be hearing Gary talk on five different topics that you need to hear before heading back to school this fall, including how to deal with parents' expectations, why school is just one path to success, and much more. If you enjoy this podcast episode, let him know your thoughts on Twitter, tag him at Gary Vee. We hope you enjoy it. This is the Gary Vee Audio Experience. Like I was a very happy kid but I hated school. Like on a different planet. I was getting D's and F's. And the world was telling me I was a loser.

0:38My teachers were telling me a loser. My friends' parents weren't saying to my face that I was a loser but I could see it in their eye that I didn't think I'd be successful because the game I played, unlike today's game, in the 80s, early 90s, was school was the way out. Going to Harvard was the great accomplishment. not building Facebook or Instagram or being a successful entrepreneur. It was a different landscape and so, you know, the why was to fucking stick it to everybody. Like I used to sit there as a 13, 14, 15, 16 year old and look at my class and my teachers and I'm like, I'm gonna show you.

1:10I'm gonna show all of you. You think I suck? I'm gonna be the biggest, best person on earth.

1:28What's the thing you did the most in your life? What's the thing you did the most that you hated? I, oh my God, I went to school for a fucking hour. Yeah! Forever. Yes, from six to 18 I hated life. College is the racket. It is the singular racket, college loans, that you can't even declare bankruptcy to get out of. That gives you a piece of paper that does not map to anything that's going on in the real world. Zero. Other than the jobs, lawyers, doctors. I know the cliche shit, but I'm talking business. And you're not watching this for lawyer shit. So business just does not map. If you are watching this and you are collecting debt to go to college to be a business person, quit.

2:11Right now. Send this email to mom. Sorry mom, fuck off. Let's start with this. I fully, fully, 100 ,000 % with no hedge do not believe that you can teach entrepreneurship. Right, so that's awkward. If there were a defined path to success, especially in any sort of creative endeavor, everyone would just follow that defined path. There is no defined path. And college can be a great way to help you find one of those paths, but it is certainly not the only way and it's certainly not a guarantee that you'll find that trajectory. I'm scared that you don't realize that you're entering the greatest five year window of your life.

2:45For you to attack the life that you want to win, not because it's the secret or because the world's so zen because it's fucking hard as shit out there. You get to live life one time. And this is the time right now to understand what's actually happening and actually map your behavior to something that will impact you for the next 80 years. Promise me that you understand that the land grab of happiness starts right now. If you're lucky enough to be graduating today with not a fucking idea of what you're gonna do with your future, nobody's ever been luckier than you. Please recognize. This next clip is an old moment from an Ask Gary Vee show where Gary dives deep into how to deal with expectations from your parents and how to approach having a tough conversation.

3:28So if you're a college student or getting ready to go to college, thinking of go to college, pay close attention. This moment's for you. How do I just, like, how do I tell my parents, like, I just want to go do for 18 months and I've been sketching out, like, all these of, like, just go do and explore. So what? They want you to get the safe job after college? Is that what you're saying? Just tell them, Nate. You're a big boy. It's time. Okay. Okay. I mean, really. Listen, listen. Easy for me to say because your dad might punch you in the mouth, right? Like, I get it. Yeah. But here's what's interesting about a lot of my advice.

4:02It's black and white. Like, you know your parents. Like, clearly your signals and your nuances haven't worked because they continue to want you to go down that path. They are not responding to you. They're responding to what they grew up with and what they believe religiously. Right? Yeah. Mm-hmm. So that means the soft way of like, hey, maybe or like them like that's not working, right? Am I right? I'm asking you. Yeah, yeah, that's totally right. I keep getting these lectures and all that. It's time for you to lecture your parents back. Okay. One of you is going to be right. Yeah. Let me promise you one thing.

4:43You really, really don't want to be 47 and hate your parents. Okay. Because I promise you, you're not actually hating your parents you're hating yourself for not having the balls to do it. Okay. You want me to come over and have that talk with you? That'd be great but, you know. You think you got this? Okay, yeah, I'll give them a call right after this. Dude, call them right now and tweet me how it went. Okay. I'm gonna literally have, since Chris isn't doing anything, I'm gonna have you, he's gonna bother you the rest of the day. I want, listen, while we're, let me pump you up a little bit more, I will be your corner man.

5:18Yeah. You start with mom and dad or mom or dad, whoever you get, I love you. I love you. Okay. Yeah. I'm 23 years old, 22 years old. Once I'm done with this, I did this for you. Now I have to do something for myself. It's high risk, high reward. But when you're 23, that's what you do because I'm not going to be able to do this when I'm 47 because it's not going to be practical. It is practical, mom and dad, for me for 18 months to just go and do and discover myself. I've been doing the thing for you my whole life. it's time that I do something for me. And if you can't support me in that, that's fine.

5:51I prefer you do but I've got to do this as a man. Okay, yeah. You don't sound pumped enough, Nate. What are you scared of? Talk to me, help me. I'm not letting, this is why I'm doing the call-in show because the old show, I would have done your tweet, I would have answered it, I would have felt great and then you wouldn't have done it. And I can feel like I almost got you there but I'm telling you right now, I don't think you're gonna do it. And if you're gonna do it, you're gonna do it half-assed. So help me here. Listen, I'm on your team so help me here understand what you're scared of. Tell me, tell me the truth.

6:22Okay, so for me like just because of the pedigree and how much education and they've sacrificed having a safe job so I can do what I want. I don't want to disappoint if that makes sense. Nate, Nate, Nate, Nate, let me help you here. Disappoint for 18 months and then make them feel good again. Okay. Just tell them, listen, I love you for that. It means you're appreciative and you love your parents. Tell them the truth. Start with that. I don't want to. Either your parents love you and will respond to you or they love you but they're so deep into structure and it's been their whole religion their whole life that they're incapable even though they love you to break through and see it a different way.

7:03The problem is it's your fucking life and it's going to end up one way or the other. Wow, yeah. That just broke through. Yeah. Like it's not that they're, right? You just gotta tell them like I don't want to let you down and just remind them it's only 18 months. Tell them for the next fucking 60 years you can do the same thing that makes them feel great. You need 18 months. Can they give you 18 months? All you want is 18 months. Yeah, yeah, yeah. And I wrote down the date, November 12th, 2018. Sign a fucking bullshit contract. Give yourself 18 months and then show them. Okay. Are you gonna do it now?

7:40Yep, I'm gonna hang up and call right now. Help me understand who is gonna be more critical. Who do you think's more scared of this move? My mom. Okay, just go there, man. Just say, mom, I love you with all my heart. I'm so thankful for your sacrifices. All I need is 18 months. I can't live with this regret in my 30s, 40s, or 50s because I'm gonna crack and I'm gonna be a broken man. I need 18 months and I promise you if I can't get traction, I'll go wherever the hell you want me to work. Yep. Yep, that's good. I'll give them a call right now and I'll tweet you in 20 minutes. Give it to me. Make me a video.

8:17I want the video. I want to see your face. I don't want the words. Okay. Alright, I love you. Good luck. Do it. Thanks. Alright. Bye. Hey everybody, I 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. Hey Gary, my name is Richard. Hey Richard. My daughter's 17. She's going to a meeting tonight with my wife. Yes. to discuss with her school, her university options, what she wants to do. She's incredibly courageous, marketing mind, communications mind. I'm taping you right now, and I'd like you to talk to her like she was your 17-year-old daughter in terms of how she should consider her university career, how she should maximize that experience to prepare her for the world that you see she may be entering into.

9:02Oof. So. Her name is Kiara. Kiara. I have no idea what's about to happen, but it's about to get interesting, Kiara. Here's what I would say, Kiara. I would tell you that there's not a school on earth, not a university or college that exists that isn't even remotely equipped to educate you properly on communications and marketing in the world we live in today. So, I have no interest, Kiara, to get your mom and dad mad at me, but I would tell you that here would be my four-year strategy. I would go to university, especially, is she going here in Canada? She's talking about NYU. She's talking about San Fran.

9:48Is she collecting debt or are you guys paying for it? I think she's just enamored by big brands. But is she gonna pay for college? Yeah, we're paying for it. So she's not collecting debt? No, well, yeah, I apologize. We're paying for it and yeah, she's gonna have to collect debt along the way. All right, Kiara, you're gonna have to have a weird conversation with your mom and dad. because the first thing I'm passionate about is for you to not have any debt because if you're gonna go to a business that is gonna sell you a shit product that you are then gonna pay compounded interest in that you can't even declare bankruptcy to get out of, that's called extortion, fucked up, fucking crazy ass shit.

10:31But, but Kira, if that number's not that high and you can get some other things that drives down that cost. The second move would be to take your last four-year vacation of your life, hook up a whole bunch, or not, you know, depending on your own radar, Kira, that might be one dude, seven. That's on you. Don't let them judge. She's a nice, good Christian girl now. I'm sure she is.

10:59And if you want to learn about marketing and communications, spend a lot of time online and consume relevant 2017 content from people that are actually doing it, not professors that are so not practical and so romantic of how it used to be that I've traveled the best universities in the world and have literally thrown up all over myself while I've been prepped to talk, listening to the horseshit that those professors are shoving down these kids' throats.

11:34Thanks, Gary. You're welcome, brother. Love you.

12:16This last moment that you need to hear before heading back to school this fall is one I chose to put at the end because at 26 years old, I think if I would have listened to this clip on repeat every single day throughout my high school and college years, I think it would have greatly improved my mindset especially because that time period of your life is a time period where you're trying new things figuring out what you don't like figuring out what you do like and really how you work and operate as a human being the last thing anyone should be worried about during that time period of trying new things is what another person thinks so i think this clip would have helped me learn start the process of learning that a lot sooner at a younger age so Without further ado, here's Gary V.

12:56You forgot you don't want to deal in reality. All my friends talking about all these changes in Brexit and presidential, you have to deal with the reality of the situation. Dwelling and pondering and crying doesn't do shit, and it especially doesn't do shit in this eco-chamber. In this arena, there is no crying. You can cry, you're just gonna lose. And I have bad news about complaining and crying. Let me tell you something about complaining and crying that's really, really gonna hurt for all you complainers out there. Nobody gives a shit.

13:35And let me give you a preview who gives a shit. The following people give a shit when you complain. The other losers around you. Your sick, broken parent that secretly wants to hold you down so that you're not more successful than them. And let me remind you one more time, the other fucking losers around you. So, here we are, heading into 2017. People are asking all sorts of questions. We still clearly are close, or it has to happen sooner than later, economic crush. Many people here, rich on paper. Go talk to a lot of 40 to 50 year olds that were rich on paper during Web 1.0 back in 99, 2000, 2001.

14:24It's sitting, it's flustering, it's here, it's upon us and now we have to, more than ever, we have to start deploying self-awareness. If you leave here and start your process of really knowing what makes you happy, of who are you really, if you could stop chipping away the voices from the outside, if you could start figuring out what you're scared of, If you want to actually do something, even in the light of the picture that I'm painting right now, who are you scared to fail in front of? The reason so many of you are not doing what you want to do is you're scared to fail in some, you're scared that your brother will judge you, your wife, your girlfriend, your husband, and most scary, your mom or your dad.

15:09You need to eliminate that and or own that fear and put yourself in a position to succeed because with all of this, with all of this, we are now in the greatest era. For the first time ever, with no fucking money, with no goddamn connections, this can put you on the map. If you're good enough, if you are good enough to be up here, to make bling bling, if you are good enough, nobody's stopping you. Not fucking Donald Trump, not the fucking Russians, nobody. If you are a minority, if you are a female, if you are transgender, if you're a fucking alien, the market doesn't give a fuck. If you make the best shit, you will win.

15:56Do you know how sucky it was to be a nerd 20 years ago? But now the market is rewarding fucking nerds and now they're rock stars. Clap it up if you're a fucking nerd.

16:15The best part about that was some dude was clapping for you and I said, clap it up and I'm fucking hurt. He was like. That's awesome.

16:26I don't know. I don't know. I'm so grateful. I was born in the Soviet Union. Both of my grandfathers spent 10 years in jail for being Jewish. as somebody who aspires to be one of the great brander and marketers of his generation, I refuse for hate and horseshit and negativity to out-market me. I will sit here today. I will sit here on the slides on every one of those platforms when they put it up. I hope they do. Follow me back there. You told me you would. Thank you very much. On stage, on those platforms, every day, 24-7, 365, I will remind you that life is phenomenal. That nobody gives a shit.

17:15So the government or your mommy's not gonna help you. You gotta do it. Own your shit. But it's never been better. We've got a bigger chance than ever. We can do our thing. And so I flew from London. I just flew in. I barely fucking made it to this talk. All the fucking guards here are fucking gangsters. right? Fuck those guards. I barely made it here and I don't know I've got some other talk now for 45 minutes about marketing on another stage and then I'm flying home and the only reason I wanted to be here the only reason I wanted to be in Lisbon for four hours today is because I knew there was a lot of you I knew there was a lot of youngsters and we are choosing what to listen to on social media now so we're going into what we want to hear and a lot of people need to hear one of two things today, which is, this is the greatest era to ever be alive and be an entrepreneur or executive if you want it.

18:11And stop complaining and dwelling, because nobody gives a fuck. Thank you.

18:31everybody if you enjoyed this podcast please go back and look at the prior episodes they're loaded i appreciate your attention and uh thanks for being part of this journey see you later

From the publisher

In this episode of the GaryVee Audio Experience, I talk about hating school, college as the singular racket, and why you can't teach entrepreneurship. I share the exact script for a 22-year-old to ask their parents for 18 months to explore, and why you really, really don't want to be 47 and hating your parents because you didn't have the balls to try. I also discuss self-awareness, who you're scared to fail in front of, and why this is the greatest era to ever be alive if you're willing to stop complaining and go.


You'll learn about:

• Why College Is The Racket

• The Greatest Five-Year Window

• Asking Parents For 18 Months to Try

• Self-Awareness Over Fear

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