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Why Most People Never Quit Their Job & Start Their Business (and How To Finally Do It)

The GaryVee Audio Experience

Wed Oct 15 2025

Summary

Podcast Summary: The GaryVee Audio Experience

Episode: Why Most People Never Quit Their Job & Start Their Business (and How To Finally Do It)
Host: Gary Vaynerchuk
Date: October 15, 2025

Episode Overview

In this energetic and wide-ranging episode, Gary Vaynerchuk (GaryVee) tackles the central question of why most people never quit their jobs to start their own businesses—and precisely what needs to change for them to finally make the leap. Via live audience Q&A and personal coaching moments, Gary delivers unfiltered advice on overcoming trauma, building content strategies, busting through mental blocks, and dealing with the fears and practical hurdles of entrepreneurship. The heart of the episode is a memorable, candid exchange with Paul from Texas, whose struggles encapsulate the fears and opportunities facing would-be entrepreneurs everywhere.

Key Discussion Points & Insights

1. Overcoming Trauma Without Money for Therapy

[02:00] Gary advises a listener battling trauma that “exercising, changing the people you hang out with, and consuming optimistic, practical, positive content” can be powerful alternatives to costly professional help.
He emphasizes separating your identity from the abuse or negativity inflicted by others:

“You must learn to love yourself and you must not take on other people's negativity towards you as an indication that it's you.” – GaryVee, [04:29]
Gary bemoans the omnipresence of fear-based media, urging listeners to tune it out entirely.

2. Content Strategy for Local Businesses

[06:18] When asked about marketing a used clothing store in a high-poverty area, Gary cuts through the overthinking:

“It's just fucking content…if you sell shit, you should never have a problem making content. You sell shit, literally.” – GaryVee, [06:56]
He suggests 4–5 daily posts across multiple platforms, always aligned with the store's actual values and community needs.

3. How to Bust Through Professional Plateaus (With Noel, the Photographer)

[07:48–21:43] In a revealing back-and-forth, Gary coaches Noel on breaking into high-level fashion campaigns via relentless networking and outreach.
He demystifies “networking”: it’s not about sending a few DMs—it's about thousands of personalized outreach messages and building actual relationships.

“When people want big goals, they have to do big things…I’m talking about you sending a message to somewhere between 3 to 4,000 people on LinkedIn…” – GaryVee, [09:45]
Gary stresses humility and the willingness to do “small shows” now to get big later:

“Having humility against your action is always a competitive advantage.” – GaryVee, [16:21]
“Nobody gives a fuck. The only people that care about fancy are other insecure, fancy people.” – GaryVee, [18:40]
Ultimately, Gary advises doubling down on the behaviors that got Noel initial success, not "getting fancy" and waiting for opportunities to just show up.

4. Coping With Overwhelm and Maintaining Positivity

[26:43] On staying positive in survival mode, Gary’s answer is blunt and rooted in perspective:

“You have no fucking choice…Life doesn’t give a fuck about your feelings. Some days it's easy, some days it's harder.” – GaryVee, [26:50]
He urges listeners to use gratitude, comparison (to worse cases, not better), and to give themselves grace on tough days:

“Even the best fighters of all time get knocked down…” – GaryVee, [28:34]

5. When a Business Partner Is Only Willing to Work 10 Hours/Week

[30:42] Gary’s answer is swift:

“I would not be business partners with that person…there’s no business on earth that is going to get anywhere with 10 hours a week. Promise.” – GaryVee, [31:06]
He distinguishes having priorities (like parenting) from having expectations about business results.

6. Paid Media for Music Artists versus Organic Content

[32:50] Gary prescribes patience:

“You need to post organic first. When you have something that pops, then you spend media dollars on it.” – GaryVee, [32:55]

7. The Main Event: Coaching Paul on When to Quit His Job

[33:27–56:51]
This extended segment crystallizes the episode’s purpose. Paul, a marketing director, wants to know when to make his successful garage clean-out side business his full-time gig. The conversation is raw, hilarious, and deeply practical.
Gary discovers Paul is already charging $699 per job and has consistent demand.
Gary’s repeated, urgent refrain:

“You need to quit your fucking job. Are you out of your fucking mind?...You can always get another job.” – GaryVee, [36:01, 38:03]
Gary diagnoses Paul's hesitation as rooted not in family needs or real risk, but in fear from a business failure during COVID and his own psyche:

“You took a macro…L and you've allowed it to consume you…It's not baby mama. It's definitely not the three munchkins. It's fucking you.” – GaryVee, [49:30]
Paul’s wife is supportive; the kids are too young to notice any potential lifestyle change. Gary bluntly says Paul’s attaching grown-up psychological stories to his kids to give himself an excuse.
On practicalities:

“Book all those extra meetings up front. It'll give you the courage to do it.” – GaryVee, [56:42]
The exchange is peppered with humor, mock insults, and love. Gary presses Paul—and listeners—to recognize that security isn’t binary, risks can be reversed, and most limitations are self-imposed.

Notable Quotes & Memorable Moments

On Overcoming Trauma:
“Consuming content and information that is optimistic, practical and positive is dramatically better than hanging around with negative people…” – GaryVee, [02:14]
On Content Creation:
“Wine Library, my dad's store, can post 93,000 pieces of content a day because they have 93,000 different wines.” – GaryVee, [07:06]
On Outreach:
“A lot of people now, that I know how to work out properly… It's form, not the pizzazz…the nuance within the action.” – GaryVee, [13:00]
On Humility & Success:
“Having humility against your action is always a competitive advantage.” – GaryVee, [16:21]
On Facing Fears:
“You can get another job if this fails…For some reason, when people see good, they’re like, Oh, this can't be. But when they see bad, they're like, That’s true.” – GaryVee, [38:06, 42:47]
On Paul's “Loser Makeup”:
“You're the best version of a loser. You're a winner…putting on loser makeup.” – GaryVee, [48:04]
On Entitlement & Parenting:
“The only people that care about fancy are other insecure, fancy people.” – GaryVee, [18:40] “For me, I'm okay eating shit… I could move back into a cardboard box if I wanted to.” – Paul, [46:10]
On Moving Past Past Business Failures:
“You got fucked…by a once in a century pandemic…not because you were taking your money and going to Vegas and putting it on black…” – GaryVee, [53:02]

Timestamps for Important Segments

[02:00] Overcoming trauma and negativity without therapy
[06:18] Content marketing for affordable stores
[07:48–21:43] Coaching Noel (photographer) on career growth and humility
[26:43] How to stay positive in tough times
[30:42] Answer on business partners with minimal commitment
[32:50] Paid vs. organic social for music industry discovery
[33:27–56:51] Deep-dive with Paul: When to quit your job & go all-in
[54:06] Moving past business failures, learning from losses

Summary Tone & Style

GaryVee’s trademark candor, empathy, and rowdy humor run through the episode. He mixes motivational truth bombs with hard business logic and pull-no-punches coaching, all in his energetic, sometimes profane, yet always supportive style.

Takeaways for Listeners

Don’t wait for permission or perfect timing—start taking relentless action, and double what’s already working.
Recognize when fear and past failures are holding you back and challenge those narratives directly.
Humility and willingness to start small are superpowers in today’s economy.
“Security” is often an illusion—real opportunity requires some risk, but most risks are reversible.
Your biggest limitations are usually in your own head, not your circumstances.

If you only have time for one section, listen to the exchange with Paul ([33:27–56:51]), as Gary’s live diagnosis and rapid-fire advice capture the episode’s heart—helping all listeners get unstuck and start building what they really want.

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Transcript

A (0:00)

Podcast nation. Before I get you into today's podcast, big announcement. As you probably heard at this point, because I had John from Stan on the show, I am an investor advisor to an incredible startup called Stan. Stan Store. I'm sending you right now to GaryVee.com, garyVee.com Stan, go check this out. We've done a GaryVee Stan store challenge, which actually has a weekly call with me. This is built for everyone who's been affected honestly by my overall content. The tech stack, all these features, and the minimal costs per month that Stan Store has built is really the tool that was needed for this world that I envisioned when I wrote Crush it, when I wrote Crushing It. And this overall thing I'm thinking a lot about lately, which is the individual empire, right? This creator entrepreneur slash entrepreneur creator economy that I think is gonna eat up the oxygen. Very honestly. The thing that so many of you want in your life and the reason so many of you are not there yet is you've got the strategy for me. You've got the ambition within yourself, but you don't have the tools for you to fully maximize it. And I believe you can find that at Stan Store. Stan Store. But specifically, I want you to sign up for it through my challenge because I want to get access with you. And plus there's a bunch of cool things. So if you want to go see those cool things, go to garyvee.com Stan S T A N Now to the podcast. This is the Garyvee Audio Experience. Welcome to another episode of Tea with Garyvee. I am Garyvee. Episode 89. Everybody, great to see you all. Great to see everybody on Instagram, everybody who's on whatnot. Good morning. Nice and great to see everybody. Let's get into this show. Pablo, we'll go with you.

B (1:46)

First, Juju asks, what advice would he give to someone who is battling with trauma with little to no money to seek professional help and it affects their day to day interactions. Yet I try to achieve goals in my daily life. What should I do?

A (2:00)

Well, look, I mean, I think at the end of the day, not everybody's gonna be able to afford therapy, but there's a lot of ways to break out of trauma or unhappiness that don't require paying a therapist hundreds of dollars. Exercise, there's changing the people you hang out with. And then my favorite one, which is I genuinely believe they're doing it right now. You know, consuming content and information that is optimistic, practical and positive is dramatically better than hanging around with negative people and consuming content that is negative. Fear based. Wheezy world. Thank you so much for the raid. That's the answer. Pablo. Like, you got to really face truth. You've also got to accept a very important thing that people struggle with in life, which is they think is their fault when it's not. When you have an abusive parent, when you have, you know, a teacher or a coach that does something wrong, these are not indications of you, they're indications on others. I have had plenty of things that have not been awesome in my life. I've had the capacity to understand that they're not my fault. Like I didn't deserve it. I think that's the real issue at hand, right? Like, I just don't understand why people. No, no. 3 Lawn said Bill Belichick isn't a bad coach. UNC is just bad. That's wrong. Bill Belichick is a shit coach. I'm going to end up being historically correct on this. I've stood on this business that the motherfucker is like terrible in his 11 seasons without the great player of all time and miraculously great when he has the greatest player. And by the way, that greatest player of all time left went to Tampa Bay and won a fucking super bowl in his fucking 40s. So you know, I don't love the guy in football life, Tom Brady, but fuck, man, he must be smiling hard as shit. I couldn't have been happier last night watching TCU dismantle unc. And that will continue because he's overrated. I otherwise. So that is his fault. He's the head coach though. I'll give him a pass. Let's see what he does over three years. Cause I know he didn't recruit those kids. That is the answer to the question, you must learn to love yourself and you must not take on other people's negativity towards you as an indication that it's you. And then finally you must, and I mean must stop consuming negativity. Going through your feed, laying in bed at 9:45pm for an hour and 20 minutes before you go to sleep, just going through your feed about negative shit of why America is going to collapse and why everything is bad and why this generation has it the worst. And all that shit is doing nothing for you. And then on top of that, you have fucking CNN and Fox News on the background. Two places that also sell fear. The whole fucking world is selling fear. Don't consume it. You don't need therapy. You know, E3 Mike says CNN consistently Negative news. True. And guess what? Fox News is scaring y' all as well. Everything's scaring you. FOX is scaring you. CNN scaring you. MSNBC scaring you. ABC scaring you. Cba, like everything's scaring you, period. Left, right, scaring you. They got all of you on lock. You are all bunched up. You're unlocked. You're on Reavis Island. You guys are all on lock. You think you're not. You think you're on one side or the other? I'm telling you right now, you're all getting fucking hoodwinkled. You're all being told the same shit in a different angle. Be scared. Be scared of the immigrants. Be scared of George Soros. You're just being all they're telling you is the same shit. Pablo, give me another questions. Oh, we got another giveaway. It's staying. Just popped again. The winner is Drew Connor, 1992. I'm gonna assume Drew was born in 92, so that's a nice little win for the youngst. All right, Pablo, get back to it.

A (10:10)

It's the same thing. It's Kind of like anything. Like when you took your first photo, were you as good as the photos you're taking now? Of course not. It was experience. Right? When I did my first push ups with Mike 11 years ago, when I started getting my health done, I did eight bad push ups. That's how weak I was. Truly. I did eight bad push ups. I had never worked out in my life. I didn't have muscles, I was overweight, it was hard, they were bad. I didn't know the form. My left shoulder didn't even know how to like close its fucking, you know, like shoulder blade. Like it was fucked up. Today I bang them out all day long. Proper form, like a fucking real player. Why? Because I did 11 years of the work every day, every day, every day. I didn't want to wake up at 6:13 this morning. I didn't want to. But I'm trying to make sure I'm in physical shape. Same thing for business. Like, I just think it's a. My biggest observation, especially as I'm bringing back tea with Gary Vee is, is people don't realize the sheer volume of the act. They're like, gary, I do do it. I do post. I'm like, no, you don't. I have 25 employees and testing and posting all day long. That's different than posting one on your grid every four days because you aesthetically want it to look good. It's just a different game. And I just think that if you want to get bigger jobs, it's called networking. The easiest way to network is digitally. You're allowed to go to cocktail parties. You're allowed to show up to places where there's PR people that might invite you to PR parties where you can literally network and rub elbows. But in the 70s and 80s, it took seven years because someone had to go out every night to trendy spots and meet people and hope and pray. Now we could just take that shit on social media, right? You can go to chatgpt and say, give me the Instagram of the 50 biggest creative directors in the world. Give me a link to it that gives you links. You click it, you direct message them. Here's some of my work. But then there's 4,000 people sending direct messages to these people with their work. So can you actually spend eight minutes looking at their profile, realizing that they like champagne or race cars or Bravo reality tv so that you could send them a different kind of message? You understand? You understand where I'm going?

A (23:33)

Loved one just by overly, you know, trying as many different things to be sympathetic and empathetic? Like, honestly, there's no right answer. Grief is devastating. I say this all the time, and it's important for all of you to hear. When I lose my mom and dad, like, there's going to be really no move other than, like, honestly, just don't bother me. You know what I mean? Just don't give me shit to think about because I'm out anyway. One of the biggest mistakes that people make in the world for others is they would like to help people the way they want to help people, not the way the person wants to be helped. I'll give you an example. This is lightweight. I turned 50 on November 14th. Everybody, real quick, please put into your Google calendar right now. November 14th, I turned 50. I expect all of you to buy 50 Vee Friends items on my 50th birthday, but we'll get to that later. I'm kidding. I'm kidding. I might. Anyway, my wife, my family, my best friends, everyone is all over me. Nick, Dio, Rodolitz, all. Everyone's all over me. Like, you got to do something. I'm like, I don't want to do anything. I want to have dinner with my family. High five. Go to sleep. See you tomorrow. Like, I don't. Like, I don't want to have a huge party. I don't give a fuck. I don't need to be celebrated. I'm celebrated every day. I don't need anyone to celebrate me. I celebrate myself. Oh, I like that. Right? Like, I don't need. I don't need it. I don't want 500 people there. I definitely don't want some bullshit gifts. You want to get me a gift on my 50th birthday? Fucking donate to Pencils of Promise or Charity Water. Oh, big, big win for Dig Dogs. Dig Dogs with a huge win. The spiffy salmon. That makes me happy. An og. All right, I'm going with a big one. Everybody. Actually, if you're new to whatnot right now, and you're kind of a nerd, you know, like, meaning Comic Con, you love Marvel, you love the Joker, you love dc, you like Comic Con, Pokemon, Yu Gi. Oh, manga, anime, you're into that shit. But you don't know anything about veefriends yet. You don't know my universe. You don't know this world. Say that's me, because I got a crazy product for you right now. The manga stickers featuring Steph Curry. Okay, first of all, that's a lot of. That's me. Holy shit. Okay, we got a bunch of new people. All right, I really exciting right now for everyone. That said, that's me. Top left corner, you'll see the logo of veefriends. In the top left corner, you'll see the logo of veefriends. This little thing right here, this little red button. Hit that. When you hit that, the third thing on the menu. The third thing on the menu is message us. I have dozens of employees in the chat in the messages to help people onboard the befriends and learn how to take the quiz. Adrian, pin the quiz. Befriends.com quiz. Everybody should take it right now and figure out which bfriend they are. All right, Pablo, let's ask Tea with Gary Vee. It's back and it's better than ever.

A (26:43)

Listen, you're allowed to have, like, bad moments. And you're allowed to have. It's too much at once. At the same token, stick with me here, Pablo. You have no fucking choice. Do you know what's funny about life, Pablo? You know, life. Let me tell you a little bit about life. Life doesn't give a fuck about your feelings. Some days it's easy, some days it's harder. But it's always good if you realize, like, you could be dead, you could have never been born. Whatever you're upset about, there's a worse version of that. Like, whatever you're upset about. How many people here have children? Say children in the chat. Every person, Courtney, that just said children in the chat. God forbid, no matter what they're upset about, got fired today, have no idea how they're getting their next check. Still better than God forbid, losing their child this morning. You know, that's just life. Like, how do I deal with it? Perspective, Pablo. Putting things in perspective. Deciding to be grateful for what I have versus dwelling on what I don't have or what's not going well. And just like living that life and realizing that you can go backwards, like, that's the key. Realizing you can always go backwards. This is what's killing people. Keeping up with the Joneses, other people's opinions. Like, whatever you're worried about, you can go backwards. You know, toxic job, quit. But Gary, fuck you. You don't get it. Yeah, I do get it, actually. By the way, on the record, none of my answers in my life have anything to do with my own personal. I do not come from a focus group of one. I couldn't answer any question that way. I only have one life. I only have my realities and perspectives. This is the cumulation of reading 1 trillion messages over the last 20 years and then watching how it plays out. Pablo Court. Do you know many people email me nine years later and be like, now I get it. Nine years later. Watch this. How many people in the chat right now hated me at one point, but now understand me and are thankful? Put thankful in the chat. Hated me, not disliked me. Like, look at this. Like, the chat went so many on one. These are. Now, let me tell you why there's so many people that say thankful. Like, why there's so many people. It's because when I talk, I poke. That person just asked me like, yo, bro, I'm struggling. What's up? And I'm like, you, that's not the normal answer. So no shit. Like, you know, like, no shit. So, man, I don't know. Like, I just want this so bad for all of you. Like, how do you deal with it? And this person Pablo, by the way, sounds like they're gonna win because they're normally upbeat, they're just dinged a little bit. Even the best fighters of all time get knocked down, right? Like, I watched Joe Frazier throw a left. I mean, I wasn't alive at the time, or I might have been alive, but I watched the video. I saw Joe Frazier throw a left hook that dropped Muhammad Ali. Dropped him right there, a couple blocks away, Madison Square Garden. But he's the greatest. But obviously, in that moment when he took that left hook, he wasn't better than Joe Frazier, let alone the greatest. That's life. Do you know that you know Brandon Warnicke? You know him? You know who runs Wine Library? Him and I did 60 card shows together. And we set up next to each other. And do you know that 59 of those 60 card shows, I made more money than him? But this one miraculous day in the Holiday Inn in Clinton, New Jersey, for whatever reason, the fucking gods decided to smile down on Brandon. And he just sold card after card after card. Brandon beat me. That's it.