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Gary Vaynerchuk
This is the Gary Vee Audio Experience. Hey, everybody. Welcome to a very special episode of the podcast. My friend Jimmy is here. We've met for a hundredth of a second. So we're going right into this. Because I'm excited about this, Jimmy. I think it's gonna be really fun for everybody. Please tell everybody why the fuck you are here. And more importantly, actually, what I'm actually asking, Jimmy, is how did you get here? Remind everybody on the opportunity.
Jimmy
I answered the. The giveaway that you had on the text platform, went on to Twitter, use the hashtag, explained. You know, I think there's a little bit about, like, you know, why do you want to be on the podcast? Yep. I got a question on the AskGaryVee show three years ago. Been doing a little bit of stuff, but not like really going hard at it, you know, like I should be. And I just put my story out there a little bit.
Gary Vaynerchuk
Let me frame it up, because I'm gonna let you take over from here. Everybody who's listening. The reason this podcast is fun for me is obviously I've started doing a lot of text messaging on this platform called Community that I'm using and couple things. One, yes, it's me. Every single text, every single time you get a reply, it's always me.
Jimmy
I believe you.
Gary Vaynerchuk
Thank you. That's why I'm using audio and video. So for everybody's wondering, it's always me. Obviously, I'm putting out stuff every day, every other day, every couple days. But what I'm obsessed with is if I'm gonna put out, hey, watch Drock's new movie, or hey, sign up for WineText, if I'm gonna be in the right hook on a text. I think unlike social, I need to be very careful there. It's a very special place. Your phone numbers. So I'm obsessed with bringing value. So I've decided that for everybody who signed up for my text messaging platform, it's gonna be the place where I create access 5 minute facetimes flying people in. We had the group. Have we aired the one with the three people that won the last thing? Not yet. So by the time you listen to this, you've already heard the podcast with the three people that were chosen. Now Jimmy's here. He was chosen. I'm gonna continue to use that platform as a way to get the ultimate thing in a world where I put out all my content for free. The only thing left is time with me. And I've decided to make my texting the most important Like a really important platform. I'm gonna use that platform as really the place to get to me. Dinner's with me, hanging out with me and Jimmy, getting the ultimate, which is being a guest on my podcast with me. So I pushed out a thing. I always like to put it on Twitter. Cause it's easy for me to find, it's fun to watch it get trending. And it's been a lot of fun. And I know a lot of you have done that. This one was to be a podcast guest. Tell me why you should. Many catch my eye. Many are worth it. And then serendipity and luck and life takes over. And that's how we got Jimmy here. So Jimmy. What? Tell us real before you tell us more about you. And then the rest of the floor is gonna be yours. You're gonna ask questions, I'm gonna answer them. But before we get that you're on my text platform A answer a couple questions. How long have you been consuming my content?
Sponsor/Ad Voice
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Gary Vaynerchuk
Let's go.
Jimmy
Almost as long as you've been putting it out from a bit so 0909
Gary Vaynerchuk
so when I kind of started first business first. When's the first time you saw me?
Jimmy
I went, I went into this for about 45 minutes the other day to try to figure it out. The first oldest video that I can remember seeing of you was a video that you did with Chris Pirillo around
Gary Vaynerchuk
2009 when I was live with him on ustream.
Jimmy
Yeah. So I remember I ready for this.
Gary Vaynerchuk
Talk about doing things for free for Expo. Chris Perlo had a huge ustream show. I believed in live.
Jimmy
Yeah.
Gary Vaynerchuk
And he was an awesome dude. Really. In the tech culture, I'd really gone head first. Dignation and Kevin Rose and those guys, Perillo, Leo Laporte, that whole scene.
Jimmy
And I struggled. I, I, I didn't struggle. I didn't struggle with you. My. It's funny because I laughed. Everyone else, everyone in my inner circle struggled with you. Like, you know my, a little bit of my family. My dad was like this guy's full of shit. He's trying to sell books. He's trying to, you know. You know. And I was like man, he a lot of sense, you know and, and I Was just getting out of a business that I was in for a long time. And so I was burnt out with that. So it wasn't using it for that, but I was doing it.
Gary Vaynerchuk
Just clicked for you, right?
Jimmy
Right. Like.
Gary Vaynerchuk
And you were a tech. You were into the tech scene because to know Perillo's. You stream back then, like, what?
Jimmy
People don't like Perillo. He's awesome.
Gary Vaynerchuk
He's super fun to like.
Jimmy
I just liked Chris.
Gary Vaynerchuk
But were you techy at that? Like, did you know what Twitter was like?
Jimmy
Yes.
Gary Vaynerchuk
You have to understand, Jimmy, you may take this for granted. A lot of people did it. People didn't know you existed. People didn't know Twitter existed.
Jimmy
Yeah, I was working for Texas Roadhouse in 2009, 2010. Went to the manager, said, hey, you know, if I could, I could run a little bit of social. The Twitter for the restaurant, they had to, like, email corporate and get approval and, like, what's Twitter? And, like, you know.
Interjecting Voice
Yeah.
Jimmy
And. And I ended up doing it. Long story short, if I could tell it for, like, 40 seconds, like, this was probably 2011, 2012. I was working. I don't want to mention any names because I don't want to throw. Throw the company under the bus. I was working at a shitty company. Shitty. The good company, but ran by shitty people.
Gary Vaynerchuk
Okay, got it.
Jimmy
Long story short, they serve coffee and donuts.
Gary Vaynerchuk
Jimmy, I like you already. Keep going.
Sponsor/Ad Voice
They.
Jimmy
So basically, I'm sorry, I'm just kind of nervous.
Gary Vaynerchuk
Don't be nervous.
Jimmy
Basically, I had a customer come in. I was running social for the company, and I knew about the location. This was 2010.
Gary Vaynerchuk
Keep going.
Jimmy
And I knew about location search on Twitter. Used to search our location for Dunkin Donuts. Literally found a customer that had a bad experience. That's exactly what you said. I mean, when I was learning your stuff, when I was learning your stuff, it was. I drove the wine to the customer from Wine Library. Reached out to this lady on Twitter that said she had a really bad experience. I said, I'm the manager at the store where you came. Come in. Your breakfast is on me tomorrow. I just want to show we're sorry. Yeah, I literally gave this lady a sandwich and a coffee, and I thought the owners were gonna fire me. Like, they were. They were so pissed that I gave this lady something for free.
Gary Vaynerchuk
That's wild.
Jimmy
Like, and, you know, and. And long story short, I didn't run social anymore for the.
Interjecting Voice
For the.
Jimmy
For the restaurant. And it was just, you know, silly. I just knew of it. I just knew it was a thing. It was y. I think a little bit after that you came out. It may have been around that time. Thank you. Economy. And it was like, man, this just makes sense. Like. Like, this is how a business should be ran. 100,000, you know, and we're still not there. I don't think the world had the infrastructure to even really understand it, run it like that, at scale, you know, and so let's bounce.
Gary Vaynerchuk
Let's bounce around. This is fun. Let's go back to the present real quick. You see the text. You. You do your thing. How do you find out that you won?
Jimmy
Oh, yeah. So I literally fell asleep.
Gary Vaynerchuk
This is better than I could have imagined. That was literally my dream beginning to.
Jimmy
It was one of those things, like, I mean, you guys know, like, when you enter a contest, you know, five minutes goes by and you're like, I'm gonna freaking win. There's like 104,000 people entered, you know, And I'm sitting there, and I'm just on, like, Instagram and Twitter and went back to Twitter. I was looking at, you know, and, you know, all the tweets are like, oh, Gary fell asleep on us and this and that, you know, And I'm sitting there watching, like, I don't know.
Gary Vaynerchuk
Right. That one. I think I had to go to, like, some meetings, right? So I was a little behind. Yeah, Yeah, I think it was a little like. One of them was.
Jimmy
I was literally. Anyway, I was literally laying in bed. I was watching.
Gary Vaynerchuk
Where do you live?
Jimmy
Alabama.
Gary Vaynerchuk
Go ahead, keep going.
Jimmy
I was watching, like, Leon Lush or something on YouTube, and I fell asleep, and I did the math. The next morning, when I figured out when you announced it, I woke up, looked at my phone, and I had, like, 100 at replies on Twitter. And I'm like, what the hell is with my Twitter account? And I looked, and it was some random chick. The first one I saw was some random girl. And she was like, you realize you won, right? And I'm like, that was the first tweet you saw? Yeah. You realize you won, right? So I woke up, my girlfriend told her, and she was like, no, you didn't. And I'm like, I swear to God, you know? And so, you know, of course, the entire morning, you know, we're at the apartment and Twitter's going off and replies, and I'm at replying to everyone. And, you know, and she's like, okay, okay, I get it. You won. Whatever. I still gotta go to work. She's like, I didn't win. I Gotta go to work. So. Yeah, you know. And so that was it.
Gary Vaynerchuk
Yeah, I love it. A couple things and then let's go into some questions and let's banter a little bit.
Jimmy
Okay.
Gary Vaynerchuk
Does your whole inner circle still hate me or have some thought out over the last decade? Damn it.
Jimmy
Most. No, no, no, no. Most. Most of them are cool. Most of them.
Gary Vaynerchuk
Most have thought out.
Jimmy
I have a few friends in Alabama that are a little on the religious side that don't, you know, is the cursing. Yeah, I respect that. I don't care. I mean, I grew up in the northeast, so, um, the. But most of my family, I think, is. Is on board. I think my dad understands, but my dad has a cynical under. He just likes giving me, like, if I. If. Honestly, no matter what, if I bring up Gary Vee, it's like, you know,
Gary Vaynerchuk
what's your dad's name?
Jimmy
James.
Gary Vaynerchuk
James. I think we have to get James on the podcast next. There's a substantial chance that James will be in the podest in a year. Jimmy. So what are you up to now?
Jimmy
I work full time as an Uber and Lyft driver.
Gary Vaynerchuk
Love it.
Jimmy
Yeah.
Gary Vaynerchuk
How's it going?
Jimmy
It's. It's okay. It's. It's.
Gary Vaynerchuk
Has it gotten tougher as supply and demand has shaked out?
Jimmy
Yeah. Summer comes in, teachers do it, teachers fall off, students come back on it.
Gary Vaynerchuk
Do you love it? Do you love the autonomy?
Jimmy
I. I love the flexibility. It's. It's a struggle at times. It can be a struggle.
Gary Vaynerchuk
Like any job.
Jimmy
You're putting. Yep. Wear and tear in the car.
Gary Vaynerchuk
What are you doing? What do you listen? Are you listening to podcasts?
Jimmy
Not really.
Gary Vaynerchuk
You're trying to put music for the guest.
Jimmy
The. No.
Gary Vaynerchuk
Okay.
Jimmy
The only reason, honestly, is because I don't have, like, what do you call it? Spotify or whatever in my car.
Gary Vaynerchuk
Got it.
Jimmy
So sometimes I'll listen to Apple music, but like on podcast, but every time something comes in.
Gary Vaynerchuk
What do you listen to? I've actually been really fascinated by this.
Jimmy
What do you mean?
Gary Vaynerchuk
Well, I always think about, like, music. Yeah, I always think about, like, what I listen.
Jimmy
I listen to everything. I mean, I grew up a deal.
Gary Vaynerchuk
Are you listening to music while you're driving or sports radio or usually.
Jimmy
Usually terrestrial radio.
Gary Vaynerchuk
Yeah.
Jimmy
Yeah, because I don't. I don't have XM or anything. Believe it or not. I still listen to CDs sometimes in my car.
Gary Vaynerchuk
I believe you. Yeah, it's very easy to believe. It's content consumption is completely predicated on
Jimmy
the distribution But I mean, I listen. I listen.
Gary Vaynerchuk
If you have a CD player in your car.
Jimmy
Yeah.
Gary Vaynerchuk
Do you garage? Actually, this is a really funny question. Have you thought about garage sailing and then, like, buying CDs for your car? This is one of the things I've been thinking a lot about is, like, I'm being serious, like, arbitrage.
Jimmy
I.
Gary Vaynerchuk
You can buy a fuckload, you can buy. I pass on them because it's a lot of, like, there's not enough margin. But, like, over the last couple trash talks, like, there's like, massive CD collections you can buy for, like.
Jimmy
Yeah.
Gary Vaynerchuk
10 bucks.
Jimmy
Yeah.
Gary Vaynerchuk
And, like, you could sell it for 100 on the Bay if you had those kind of hours, which is why it's a good buy. But specifically for your life. That's like a real arb.
Jimmy
Yeah, but I don't like them enough, though.
Gary Vaynerchuk
You don't like music enough?
Jimmy
I mean, I like music. I love music, but I. I like.
Gary Vaynerchuk
You have your six things you like,
Jimmy
and why that I probably wouldn't.
Gary Vaynerchuk
You don't need to buy a Lionel Richie cd, right?
Jimmy
Yeah, Yeah, I do like Lionel Richie, though.
Gary Vaynerchuk
I love.
Jimmy
I know.
Gary Vaynerchuk
That's so awesome, man. No wonder we're friends.
Jimmy
Yeah, I used to be a dj.
Gary Vaynerchuk
What? I heard that.
Jimmy
Yeah. Yeah. So, I mean, I grew up with tons of music.
Gary Vaynerchuk
Like, have you flipped?
Jimmy
I know I've been pushing that. I flipped a little bit. How's that?
Gary Vaynerchuk
Like, tell me about that. I thought that's it. Because I love places like Bama and other places where I think there's real arbitrage.
Jimmy
So the. The best I've had small ones, but the best flip I have because I know you like hearing these stories.
Gary Vaynerchuk
Dude, you know me so well. You look right to what I wanted. I love you, Jimmy. Go ahead.
Jimmy
The best flip I had was one of those scientific calculators.
Gary Vaynerchuk
Yeah.
Jimmy
I got at. I don't know, it wasn't a Goodwill, but it was some, like, thrift store. Yeah. Like a thrift store. And, like, somewhere in the hood in Birmingham. And. And it was literally. There was no batteries in it, it was greasy, it was dirty, and they were selling it for, like, a buck. And, like, I don't think they knew what it was. And I was like, well, I'll pick it up for a dollar.
Gary Vaynerchuk
Did you know there was value in
Jimmy
it or you were going to hunch? I knew if it worked, it was worth more than a dollar, you know, and so I was like, well, I'll buy it for a dollar. So, you know, if. If Anything. I can sell it as broken for five bucks, you know, So I was like, I'll buy it for a buck. And it sold. I cleaned it up, washed it, you know, put new batteries in. It worked perfectly. I sold it for like, 70 bucks on eBay.
Gary Vaynerchuk
Love.
Jimmy
Yeah.
Gary Vaynerchuk
Why don't you do more flipping when you follow careful? Like, I always thought the Uber Lyft driver and flip combo combo was a monster. Was a monster because you're naturally driving around anyway.
Jimmy
Like, plus, you could pitch to your passengers if they have anything they want to get rid of.
Gary Vaynerchuk
Well, that's, that's taking it a little far, Jimmy.
Jimmy
But.
Gary Vaynerchuk
But just being on the road at all times puts you in play to finding random closeouts for stores rolling up on a garage sale. Do you just not like it, or is it hard? Like, why don't you do more flipping, is my question. In a world where I think you could clean up because you have the knowledge.
Jimmy
I don't know. I don't know exactly why it is. I, I, I mean, I'm ashamed to say I think a little bit of it might be laziness, but actually, let's.
Gary Vaynerchuk
Can we stand?
Jimmy
I don't know. I mean, I'm not.
Sponsor/Ad Voice
Jimmy.
Gary Vaynerchuk
I'm going to lean into this because I want to bring value to everybody listening.
Jimmy
Yeah. I.
Gary Vaynerchuk
This is going to actually probably confuse some people. I actually don't spend a lot of time on laziness. Right. Actually, think about it. I don't talk about it. Right.
Jimmy
You mean in your content?
Gary Vaynerchuk
Yeah. By the way, my content is a manifestation of what's in my mind. So not even in my own mind when I hear that. I appreciate why you say it, but it's so funny. It's funny how that just went through my mind. I actually think being lazy is a good thing. Let me explain. This is gonna be an interesting moment. Yeah. No, you're freaking out, right?
Jimmy
I was gonna say, isn't, like, stop watching Netflix kind of, like, related to laziness?
Gary Vaynerchuk
Stop watching Netflix is under the context of stop using something to escape your real life. If you don't realize you're trying to escape your real life, don't use Netflix or watching the New York. Let's get very much into clarification on this episode. I watch the jets for four hours on Sundays. I do that because it allows me to escape and, like, it gives me balance to my insanity. But I don't watch the jets on Sunday to get away from the fact that I hate my job. And instead of doing something, like, for My job, I'm gonna use this because Netflix is a seven day a week thing, 2K and Fortnite is a seven day a week thing. And even sports people that watch the Yankees and the Mets and the Knicks and the jets, the way I watch the jets, that's why football worked for me one day a week. You know, some people use entertainment as a reset and a balance to their other life, which is work, family. And then other people use escapism as a way to just get by because they hate their life and it's the way for them not to have to think about it. Right? Laziness has my attention because I think if you're lazy, you're actually giving yourself an indication that you don't like it. So I think laziness, you don't like what? Whatever the task at hand for you, you just prop I, you'll appreciate this. And I think you can see it in trash talk. I mean I'm never. Drock will tell you who hangs out with me a lot that between trash talk and the baseball card show in Chicago, he's never seen me happier. I get an incredible thrill, deep inherent happiness from getting into a car on a 6am on a Saturday and going to find something to buy for 3 bucks and sell for 100. This is not about the cliche shit that people say in my comments of like, you didn't make that much money. It was the gas. You know, it's not all those things. I love it. School, I hate it. I am lazy around housework, around logistics. I think quote unquote, laziness can have a more thoughtful conversation of actually, is it laziness or are you showing yourself that you don't like that thing and and it becomes a mechanism to self awareness.
Jimmy
I think it's that, I think it's that you don't like that thing.
Gary Vaynerchuk
I think me too. Yeah, I don't think you're lazy and
Jimmy
I think a little bit of the.
Gary Vaynerchuk
You're not lazy.
Jimmy
I think a little you're fucking.
Gary Vaynerchuk
I apologize, but I want to give you a compliment. You're driving around hardcore, grinding, lifting. You're not lazy. You just don't get the same thrill or enjoyment.
Jimmy
And I think a little bit of
Gary Vaynerchuk
it is, hey everybody, hope you're enjoying the podcast right now. Make sure you follow the podcast. That's why I'm interrupting. Let's keep going on this show, but follow the podcast. It'll make my mom super happy. What it is, Drock is I think we need to stop apologizing for being lazy, all of us, which is probably subconsciously why I don't talk about it. And we need to use it as an indicator of I don't like that thing, this job, this relationship, this school, this startup. And then use it as a starting point to try something else on the side that eventually can become your thing and you can stop doing that thing that you're, quote, unquote, lazy about.
Jimmy
So this may sound weird to you, but I was just thinking of it as you were saying, talking. I think a little bit of it, too, for me, like, because I do like the flip stuff on ebay. Like, I do enjoy it when I do it. I think a little bit of it for me is also the economics of it. You know, where I'm thinking, like, okay, if I'm out doing this, it's taking away from me. Doing that analytical side of me. I like, that prevents me from doing anything for four years. Like, the analytical side of me thinks, like, well, if I'm garage sailing from 6 to 8, like, how much could I have made with Uber and lift?
Gary Vaynerchuk
No, no, that's. You know, by the way, that's exactly right.
Jimmy
Right.
Gary Vaynerchuk
And then in the comments of this, wherever that may be.
Jimmy
And I'm one of those cynical people, when you. When. When you first got onto garage sailing, I was like, yeah, but the gas and the ebay fees and this, the boxes and, you know, and then my girlfriend said, you ain't gonna store the here. Like, you know that. Not that. Not that she would say, say that,
Gary Vaynerchuk
Jimmy, I think you'll like this. And that makes sense.
Jimmy
My dad did, though, when I was living at home. When I was living at home, my dad was like, you ain't keeping that. James is.
Gary Vaynerchuk
I mean, this guy, I can't wait to meet him. Is he a Bama guy?
Jimmy
Are you both you Bama guys he rooted for? So 22nd story. My parents moved to Alabama. My dad got a job offer down there. He owned his own from Massachusetts.
Gary Vaynerchuk
Okay. Are you a Patriots fan, Jimmy?
Jimmy
I'm borderline. Like, I'm a Pats fan because I grew up. But like, a Pats fan.
Gary Vaynerchuk
Right?
Jimmy
Honestly, don't. What are you.
Gary Vaynerchuk
Are you a real fan of anything?
Jimmy
Probably the Red Sox and Bruins.
Gary Vaynerchuk
Okay.
Jimmy
Yeah. Yeah. But like, Pats, I mean, it's not your passion. Yeah.
Gary Vaynerchuk
You're more of a baseball.
Jimmy
Like, I'll catch a game if it's on, but it's not. Like, Right. I don't care if they lose.
Gary Vaynerchuk
I understand.
Jimmy
Yeah. Like, I was probably like, the Game
Gary Vaynerchuk
7, the Stanley cup this year broke your heart. Yeah, but the Patriots losing the Eagles, not so much.
Jimmy
Yeah, like I was actually. It's so funny because like I have this thing with like Gary buying the jets literally every time the jets are playing. Like I have this innate like. Yeah, I'm kind of a Jets fan.
Gary Vaynerchuk
Like, well Jimmy, this is the masterful thing I'm doing.
Jimmy
I know.
Gary Vaynerchuk
I'm literally going to turn America into a collective monster Jet fandom by the time I buy it. So when I buy it on day one, they become the most popular team in the league.
Jimmy
I could see that.
Gary Vaynerchuk
Dustin, you haven't been noticing. I love your face right now. You think I'm fooling around around here, Dustin? I've got everything figured out.
Jimmy
Let's say the jets just started winning all the time.
Gary Vaynerchuk
I won't care. I'll pivot to the Knicks. If the jets won back to back Super Bowls in four years, I probably will change the narrative to the Knicks. I'm about the thrill of the hunt and I think them winning and becoming the kind of. That's if you listen to Patriots during Jimmy's dad's years for sure. And how old are you, Jimmy?
Jimmy
37.
Gary Vaynerchuk
So even a little bit of Jimmy, a little bit like he's right on the cusp. Like the Pats were real bad.
Jimmy
I understand though your underdog thing, it's
Gary Vaynerchuk
like the Red Sox especially.
Jimmy
I mean I, I understand that.
Gary Vaynerchuk
37. So you, you.
Jimmy
Oh, I watched what year I was bit. No, forget about born.
Gary Vaynerchuk
Yeah. What year?
Jimmy
82.
Gary Vaynerchuk
Right. So you don't remember 86.
Jimmy
No. Jimmy, no.
Gary Vaynerchuk
You can't imagine.
Jimmy
Oh, I know.
Gary Vaynerchuk
I don't know if you know this. Like you probably don't. And I mean all you non sport, you three guys, you non sports fans, for everybody listening, the Red Sox were winning by two runs or I'm trying to remember, I think it was two runs.
Jimmy
One or two runs in game six
Gary Vaynerchuk
of the World Series. Up three games to two here in New York in the bottom of the ninth, two outs, nobody on. They're one out away from winning the World Series. The game is so over that the Mets in their stadium put on the Jumbotron. Congratulations. Boston Red Sox, 1986 world champions. And they lost that game a single, another single, then another hit. And then this famous play for Bill Buckner went under his. You know that play that happened in that game.
Jimmy
I actually. Wild pitch. I actually joke with people that Buckner didn't really like lose the game, but
Gary Vaynerchuk
it was because of the, you know.
Jimmy
Yeah.
Gary Vaynerchuk
You know. So it's, it's crazy. It was tied by then because of the wild pitch. Nonetheless, it is the most ridiculous thing that I've ever seen in sports to this day. It was over. Over. I mean I was. Listen, the Jets, Monday night miracle. They were down 30 to 7 with 10 minutes left in a football game
Jimmy
and came back and won 04 against the Yanks. That was pretty big though.
Gary Vaynerchuk
Yeah, that was amazing. Three games to none for like by the way, I always think that the jets moment will happen through New England because it's like that's what the Red Sox did to the Yankees. I'm looking for the reverse. Nonetheless, Jimmy, to bring value to the audience. What apps are you into right now? Like what content are you consuming? What platforms?
Jimmy
I've always liked Twitter. I don't get on Facebook a lot. Even for family and friends. I don't get on it a lot. YouTube a little bit. A little bit. YouTube, Twitter. I'm trying to get into TikTok. Yep. Been playing with it a little bit. Yeah. A little bit of Instagram. Not. Not too, too much.
Gary Vaynerchuk
What can I answer for you? Let's wrap up this show with two or three questions.
Jimmy
So God man, I have like 100 Rattle Way.
Gary Vaynerchuk
I'll go.
Jimmy
The first question that comes to mind is I love your message of like 100 pieces of content a day. You know that, that theory I'm my. My question on the the first call in show that we had was about travel blogging which was for me a little bit related to photography, travel, writing, video. I try to do video but it's not really my thing where my thing is like if you're working and you're doing your life stuff, if you put out so much content it would literally be like the same content every day.
Interjecting Voice
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Gary Vaynerchuk
I think it's a really good question. Couple things.
Jimmy
Especially if you're wanting to do something like travel, this is tremendous.
Gary Vaynerchuk
This is where creativity and ideas has to be something I talk more about. So for example, when I think about 100 pieces of content a day and this is Great, because it seems like you're grounded in Twitter most, more than many, because you were part of that era with me. Yeah, I think Twitter is an incredibly important part of the hundred piece concept. You know, obviously this is catching and I'm getting asked about it more. So this is a great opportunity to create some clarity. Hopefully the team clicks this. Let's get Raghov to write a piece. You know, the 100 piece concept 2.0. I think we're working on something. But Twitter's incredibly important. As you know, one of the great things about Twitter is its trending topics and the ability to reply to it with retweeting and adding your $0.02 or typing original thoughts. So for me, one of the things that really stands out is if I was asking the normal quote unquote person to produce 100 pieces of content a day, I guarantee you that I'm probably subconsciously thinking that 50 of those are Twitter. You can write, you can retweet and add your two cents. All of a sudden you're kind of there. Right. The other thing is I don't think people understand document versus create. I think people think you need Drock or Jason following you or Dustin following you around. I think it's just taking a picture. Like, I see content right here. Like, I see content in maybe I have. This is probably my strength. I see content in everything. I think you should take a photo of us talking right now and tweet it and be like, holy shit, I'm doing this with Gary Vee right now.
Jimmy
Yeah, yeah, I did. I took right before you came in.
Gary Vaynerchuk
But like, there's Madison Square Garden.
Jimmy
Yeah.
Gary Vaynerchuk
And you know, like, this is New York. You know, like, I think there's a lot more content. And by the way, I think that could be done 15 to 20 times on Twitter, Instagram stories and TikTok without any cost to the preciousness. That is the main reason that Everybody can't make 100 pieces of content.
Jimmy
Okay.
Gary Vaynerchuk
You know, taking a photo of what you see and adding one sentence is allowing people into your world. And you start creating around common interests. A lot of people are like, gary, should I separate my business and life? I'm like, I put my jets content in all my content. I put my garage sales stuff there. That has nothing to do with the marketing or the business running. I think it's there. But I do think it's a strategy mindset. And I think everybody thinks this is useless and nobody would care. And I think you should let them decide. I think when you Think something like, I think when you think, you know what? I wish I was closer with my sister. And I'm gonna start working on that. That. That should be a tweet. That one should tweet. Like, you know what? I've been underestimating sibling relationships. And I'm gonna work on that in 2020. That's a piece of content. And then you're walking into a restaurant, a fast, casual place, and there's 23 people lined up to the hottest place in downtown Alabama or New York. And you take a photo and be like, I guess cronuts are hot. That's a piece of content. And if you're more visually artistic than I love when the sunset hits, like, some avenue in fucking New York and everybody's taking a photo of that. And I have no interest, even though I'm into this content thing, I'm like, fuck that. First of all, I don't get it. Cause I don't give a fuck about a sunset. But I know that people do.
Jimmy
Or mountains or mountains.
Gary Vaynerchuk
Or. I'm looking at the creative guys in front of me here, gals. I know that they see beauty in a puddle catching a mini rainbow in it. That I'm not that kind of artist, but I'm an artist in a different way. Where somebody having a funny name on their taxi thing or like. Or what? You know, like, everything is. Do you. Do you.
Jimmy
And I mean, I know there's 100 other people that do it, but I'm most familiar with Drock. Like, do you struggle with that, with your video people? Because they want everything to be very artistic?
Gary Vaynerchuk
No, I fucking made them succumb. I beat Drock down and reframed him, and then he became the blueprint. Right? I mean, no, I don't. And by the way, this is Bing Ying and Yang. And we're sitting here. And we're sitting here on the day that we released a nice piece of film. That's 5 minutes and 50 seconds. And I value that as well. I'd rather go all in on that side once a quarter than every day spending four days on post production on a vlog, you know? So, like, you know, I like. I'm like a barbell. I like the extremes to the left and the right. And I think most people are in the middle. So that's how I see that. What else you got there? See? Notes.
Jimmy
Yeah. So a little bit related to the question I asked before. If you were wanting to get into, like, photography five minutes.
Gary Vaynerchuk
Drock.
Jimmy
Like, photography five minutes.
Gary Vaynerchuk
Go ahead.
Jimmy
If you want to get into like photography, travel, that sort of thing. Like, I own my name pretty much across social. I don't have the.com but I have the.co domain. Pinterest, Twitter, Instagram. Yeah. Should you, should you build more of your name as a person in your area or. I know this is gonna sound identical. Identical.
Interjecting Voice
Go ahead.
Jimmy
Because whenever I think about doing that, I think like, well, if you did it under whatever, like Birmingham something, people would instinctively be more. Understand it more because it's in the name.
Gary Vaynerchuk
The execution will make the name. Let me explain. I understand the literal interpretation of Birmingham photography. If you call it at Birmingham Photography or if you call it Jimmy.
Jimmy
Yeah.
Gary Vaynerchuk
The execution of the photos will become the end result. Whether McDonald's called itself McDonald's or McDonald's, whether Google called itself Google or Schmoogle, whether Facebook called itself Facebook or Base Book, and whether Nike called itself Nike or Schmikey. You got it?
Jimmy
I got you.
Gary Vaynerchuk
My name's fucking Gary Vaynerchuk. My username is Gary V with two silent E's. That's stupid. Yeah, that's stupid. It was the execution that made it okay.
Jimmy
So my follow up question is if you're building your personal brand like I'm wanting to do through photography, travel, writing, that sort of thing, one of the pieces of content that you had that I remember that I loved was, I think it was one of the. One of the guys you were interviewing. You mentioned about having different burgers where you have something else. Is that a different what? Yeah, beside like side thing. Having like a burger, you know, something you rely on.
Gary Vaynerchuk
Yes.
Jimmy
You know, is it a good strategy to completely focus on you or to build some other stuff up so that you don't have to monetize an audience in the future as much?
Gary Vaynerchuk
That's a really good question. So first of all, one never has to monetize an audience if they build themselves up. They just have to be capable of building something around it. Like the reason I get to be a hero and not monetize my audience is I was capable of building VaynerMedia. Right. You don't have to monetize. Now, let me give you an example. You putting out great photography for free, you by nature and the service you provide have the potential to monetize the audience in a way that's good. Let me explain. I am a strategist. I'm actually a thinker. I don't position myself that way. But what people want to pay me for, or would want to pay me for is to sit down with me and do this for hours. I give that away for free, and then I don't monetize that way. But if I was a photographer and they wanted me to shoot their wedding, I have no choice but to charge them for that. I got lucky that my output was thoughts, and I could give that away for free if. If my output was photography and I'm
Jimmy
not wanting to do client work, that's like. I just love shooting photos when I'm out. Like, I just. I've done it.
Gary Vaynerchuk
You just. You just won.
Jimmy
Yeah.
Gary Vaynerchuk
I mean, obviously you have to maintain a living.
Jimmy
Yeah.
Gary Vaynerchuk
But this is actually my favorite thing. You're like, almost my favorite person. If you have a life where you. Let's say you. I don't know how much you love shooting photos, but it seems like pretty solid.
Jimmy
I'd say 80%, 90%. I mean, it's.
Gary Vaynerchuk
It's like your thing.
Jimmy
It's my thing.
Gary Vaynerchuk
Right. You know, to me, the fact that you have your core hustle around Lyft and Uber, which allows you, you know, you know, I got you.
Jimmy
Oh, I know. I know where you're going. I know.
Gary Vaynerchuk
To do that. You're actually. You're actually the fucking poster child of what I'm trying to get people to understand if you're happy you've won now, if you're telling me. Well, Gary, actually. Which would make sense, by the way.
Jimmy
Yeah.
Gary Vaynerchuk
I would love to just do photography all day long and I'd love to get paid four times as much to photography.
Jimmy
Yeah.
Gary Vaynerchuk
Like, I still think it's the same strategy, which is put out the best photography you can, and over time, serendipitously, you know, people are going to reach out to you and offer you gigs.
Jimmy
Yeah.
Gary Vaynerchuk
Not super complicated.
Jimmy
Yeah, I mean, I'm. I'm. What I'm doing right now is like, I've actually been doing this on my YouTube channel, just kind of for fun. I've been documenting. It is part of my, like, photography and U. S. Travel thing. There's a. A travel group online that I'm a part of that I'm trying to actually visit every U. S. County.
Gary Vaynerchuk
Excuse me?
Jimmy
I'm trying to visit every county in
Gary Vaynerchuk
the US isn't there like a.
Jimmy
There's like 6, 000. It's a thing. There's like 51 people that have done it.
Gary Vaynerchuk
Hold on. How many counties are there, do you know roughly?
Jimmy
Or the range of 3140. 3142. Something like that.
Gary Vaynerchuk
3000 plus.
Jimmy
Yeah.
Gary Vaynerchuk
30 fucking cool.
Jimmy
Yeah.
Gary Vaynerchuk
Anybody listening who can help Jimmy with this county thing? Maybe there's some map company that wants to pay him to, like, travel the. You know, Babin's doing some bullshit like that. Like, so why can't.
Jimmy
I love what Babin's been doing, by
Gary Vaynerchuk
the way, I'm sure Babin's super creative and, you know, Adobe's letting him do it. And so I think for you, like, AAA Car services CEO could be listening right now and said, fuck it, I'm gonna take Jimmy and I'm gonna, like, pay for his year. And he's gonna go to every county because the awareness of the GaryVee, you know, podcast, is probably work. Like, I. Basically, you're just a mini Babbin. We're gonna get you this gig. Somebody listening right now is gonna hit up AAA or some map company or some other fucking travel infrastructure, and they're gonna reach out to you cold and they're gonna pay you for a year to go every county. I believe that to be true. That will happen.
Jimmy
3242 County.
Gary Vaynerchuk
Jimmy, this is what you want to do with your life. Like, you would like it.
Jimmy
Yeah.
Gary Vaynerchuk
I would not take that in a negative way.
Jimmy
It would take me at least 10 to 15 years to do it.
Gary Vaynerchuk
You're a young.
Jimmy
Yeah.
Gary Vaynerchuk
Who are these 50 people? And, like, do you, like.
Jimmy
You know what's so funny?
Gary Vaynerchuk
What?
Jimmy
So I'm gonna tell you something because you're gonna love this, because I know the business part of you.
Gary Vaynerchuk
Yeah.
Jimmy
I've looked up. I've googled every. Every single one of their names because I'm like, if 50 something people have done this, one of them.
Gary Vaynerchuk
What's the. What's the common denominator of the 50 people?
Jimmy
What do you mean when you looked
Gary Vaynerchuk
up these 50 people, they're old. That's solid. It takes a lot of time.
Jimmy
No, I mean, I mean, I think, you know, they were doing it over, you know, 30 years, but nobody has documented it. There hasn't been a single person that has done it, that has documented. It's sort of like a word of faith type thing. You know what I mean?
Gary Vaynerchuk
You want to document it?
Jimmy
Yeah.
Gary Vaynerchuk
How many are you in?
Jimmy
So I visited in my life, technically, because I figured this out, probably 180.
Gary Vaynerchuk
But you haven't documented.
Jimmy
But I have a document, so I'm. I'm redoing it.
Gary Vaynerchuk
Right.
Jimmy
I've been like seven, eight.
Gary Vaynerchuk
Great.
Jimmy
Yeah.
Gary Vaynerchuk
You have a big journey in front of you, just like I do, which makes it the most fun.
Jimmy
So can I ask you like a couple more questions real quick. Real, real quick. Okay.
Gary Vaynerchuk
My team kills.
Jimmy
So you know, because I love this platform and I'm hoping it's not. Not bullshit. You know that Flickr was bought by SmugMug.
Gary Vaynerchuk
I did see that.
Jimmy
What are your thoughts on Flickr as a platform for photographers? Flickr, Honestly. Honestly, Honestly.
Gary Vaynerchuk
Flickr owns my heart. There's like I have like six photos on Flickr. What is it? G Nuts. What is the username? Because that's what I used to use back in the day. Flickr was. Flickr means the world to me because it was one of the sites that got me into tech.
Jimmy
Were you glad that it was bought by SmugMug?
Gary Vaynerchuk
I don't know what SmugMug's gonna be, but I definitely remember Flickr super well. Stuart Butterfield, right. Who went on to be the co founder of Slack.
Jimmy
Yep.
Gary Vaynerchuk
They sold it to Yahoo. It was one of the big exits. I remember it like yesterday. And I still think that Instagram really is what Flickr could have become if it was in the mobile age. And my heart is huge for Flickr. It was the first time I saw photography that way. It was a preview to the current state of the Internet.
Jimmy
If you're doing Instagram right now as a photographer, should you still be using Instagram as a photographer does, or should you be posting most of your story on your post?
Gary Vaynerchuk
There is no should. And can you use Instagram as a pure play photographer at scale? Yes.
Jimmy
Are people still searching hashtags?
Gary Vaynerchuk
Not as much, but.
Jimmy
But a lot.
Gary Vaynerchuk
Yes.
Jimmy
Yeah,
Gary Vaynerchuk
it was Gary B. With. With no double E. Right. Did we change it? Go ahead.
Jimmy
And my last question. I'm hoping it's a decent one for photographers.
Gary Vaynerchuk
This couldn't have gone back. When you play the game of I think somebody.
Jimmy
I think this couldn't have gone better. I think an industry that needs to be massively disrupted, that hasn't really been disrupted yet is stock photography.
Gary Vaynerchuk
Okay. I tried to. I, I was an investor in a company called Fope F O A P where everybody's photos on their phones would be uploaded and it was a marketplace against Getty Images and things of that nature. And I thought it was a super good idea.
Jimmy
So what about what would a. What would it look like from a business person standpoint like yourself for a photographer down the road to do that
Gary Vaynerchuk
themselves to build a platform?
Jimmy
Yeah.
Gary Vaynerchuk
Well, to understand it's a super difficult business to build.
Jimmy
Okay.
Gary Vaynerchuk
It's a two way marketplace. It's like ebay and Uber and those are the toughest ones to build. You want the world to upload photos, right? Because they have it.
Jimmy
No, I'm saying. I'm saying your own iPad.
Gary Vaynerchuk
Well, your own ip. I think you need to build your personal brand and demand and create demand for you. You want to get my creative directors at Vayner, production people, brands to be like, we need Jim.
Jimmy
See, I've always thought stock photography should work the other way. Where right now, if you go on to, like, you know, Getty or Istock or whatever, it's like, I mean, you guys probably know this as content creators that you go on stock photos and you, you know, upload whatever and they pay you 38 cents for a photo.
Gary Vaynerchuk
It's like it's supply and demand, right? The reason you pay 38 cents is because 8,000 other fuckers are putting up a photo of a Robin.
Jimmy
But it's like, I'm wondering why a company hasn't come out that have approached some of the top stock photographers and say, pay us $400 a month or $800 a month and you get 100% of the royalties.
Gary Vaynerchuk
Because the business model in the other way is better and the leverage sits with the platform, not with the photographers. You're thinking about it from a selfish standpoint of the photographer, because that's what you want to be, which is right. The answer to your question is the photographer doesn't have the leverage.
Jimmy
But if a photographer built themselves up
Gary Vaynerchuk
big enough, they would, then they wouldn't need the platform.
Jimmy
Or they could have leverage to create the platform with someone else.
Gary Vaynerchuk
They could, if they know how to build a platform. Just because you're Shaq doesn't mean you can build the NBA.
Jimmy
Right?
Gary Vaynerchuk
Got it.
Jimmy
Got it.
Gary Vaynerchuk
That's a really good way to end this. Thank you, Jimmy, everybody. If you enjoyed this podcast, please go back and look at the prior episodes. They're loaded. I appreciate your attention, and thanks for being part of this journey. See you later.
Date: July 15, 2026
Host: Gary Vaynerchuk
Guest: Jimmy
This episode features Gary Vaynerchuk in a candid, fan-driven fireside chat with Jimmy, a listener who won the chance to appear on the show via Gary’s text platform giveaway. The conversation explores Jimmy’s journey, the evolution of technology and social media, the realities of life as an Uber/Lyft driver, and—centrally—the real meaning behind “laziness.” Gary challenges conventional ideas around lack of motivation, reframing it as a signpost for self-awareness and true interests, while giving actionable advice on content creation, personal branding, and the value of happiness over “hustle.” The episode is rich in practical insights, personal anecdotes, and trademark GaryVee energy.
“I actually think being lazy is a good thing. Let me explain…If you’re lazy, you’re actually giving yourself an indication that you don’t like it.” — Gary [14:28]
“Whether Google called itself Google or Schmoogle...it was the execution that made it okay.” — Gary [30:12]
“If you’re happy, you’ve won.” — Gary [33:08]
On Laziness:
“I actually think being lazy is a good thing...laziness can be a mechanism for self-awareness.”
— Gary Vaynerchuk [14:28]
On Content Creation:
“Content is...taking a picture. Like, I see content right here. Like, I see content in everything.”
— Gary Vaynerchuk [25:39]
On Personal Branding:
“Whether Google called itself Google or Schmoogle...it was the execution that made it okay.”
— Gary Vaynerchuk [30:12]
On Winning at Life:
“If you’re happy, you’ve won.”
— Gary Vaynerchuk [33:08]
On Documenting Unique Journeys:
“Maybe there’s some map company that wants to pay him to, like, travel...maybe AAA or some other travel infrastructure, and they're gonna reach out to you cold and...pay you for a year to go to every county. I believe that to be true.”
— Gary Vaynerchuk [34:24]
Gary is at his most practical and philosophical, blending actionable guidance with energetic, direct engagement. The discussion is affable and relatable—constantly circling back to the idea of leveraging self-awareness, finding real joy, and not overthinking how others perceive your path or output. The conversation with Jimmy stands as a real-world case study in transitioning from passive fandom to active creation, using humility and personal curiosity as rocket fuel.
This episode is essential listening for anyone who feels “lazy,” is uncertain about their side hustle, or is overthinking their “niche” or “brand.” As Gary sums up:
“If you’re happy, you’ve won.”