Loading summary
A
Hey, before we jump into the show, I wanted to give you a heads up that my free YouTube strategy class is available right now on demand@thinkmasterclass.com on the class, I reveal the one YouTube strategy we use at Think Media to generate over 330,000 views every single day. So if you're new to YouTube, this will help you start right and avoid mistakes. And if you're a YouTube pro, this training will help you multiply your your growth. This class is 100% free and you can watch it now on demand at Think masterclass. Com. Now let's jump into today's show. Most creators are trying to go viral. They're jumping on trends, they're chasing views, but they're staying stuck. What does it actually take to build something that lasts? But this conversation is going to be different because we're going to be unpacking the journey of how both of us have actually built million dollar brands.
B
Before, anybody would have labeled me like the guy or whatever. I was applying branding internally within the organization I worked for.
A
What do you mean by that? Well, Caleb Ralston, he's the brand strategist behind Gary Vaynerchuk, Alex Hermosi, and he's helped build brands that have reached over 30 million followers over the years.
B
A trap a lot of creatives can fall into is they learn tactics. They don't ever step into principle based learning.
A
Take us back to 15 year old Caleb. Where did this all start for you?
B
You had mentioned the book Crush it by Gary Vaynerchuk. I remember when he talked about people being passionate about the Smurfs are gonna make money. Talking about The Smurfs on YouTube, I was like, well, I'm into bodybuilding and powerlifting. I could probably do that after the bodybuilding era. There's the photo that Gary posted on his story saying that he's looking for videographers. My name is Kayla Bralston and I wanted to make this quick video introducing myself. And I got paid $75,000 a year to Lear from Gary Vaynerchuk to learn. Yeah. Rest is history.
A
Fast forward a few years. You are number one@acquition.com on the content team. What is like two big insights from you getting to work with Gary and you getting to work with Alex. Let's start with Gary. Not only will you be getting actionable, real insights to build your brands, get views on social media, grow on YouTube right now, but some mindset and really evolutionary principles of what it really takes to build something that lasts over time. And so, Caleb, I do want to start off though, before we get into to, like, your backstory, some of the pivot moments and some huge insights that anybody can imply. What is like two big insights from you getting to work with Gary and you getting to work with Alex. Let's start with Gary that you learned being immersed in that environment that someone can apply today.
B
There's a lot. So it's always hard to choose from. But what I will say is I think the thing that I am trying to apply to my content creation journey is putting the audience first, even above my own selfish interests. I've seen not only heard Gary talk about it, but I've seen it time and time again where there are moments where he could be doing something that would be far better for his brand or one of the companies that he owns, one of the millions of companies that he's got, but he chooses to continue engaging with the nine year old that loves veefriends in a world where he could be taking a photo. I mean, we were just filming with him recently for like the comeback of DailyVee, and I was filming a moment where a really big name artist was like coming over and was gonna take a photo with Gary at the veefriends booth. And everyone was trying to get Gary to come over and get the photo because this person was gonna end up moving on and stuff like that. And Gary was talking to a young kid in a wheelchair. And I remember seeing the moment and being like, everybody else would have walked away for a second and then come back and still engaged. And there would be nothing wrong with that because they would want to serve their own selfish interest above their audience. And I've seen Gary hundreds of times do that over and over and over. And so I think, like, for me, it's figuring out what is my version of that. I don't think I'll ever be at that point in my career or anything like that. But how can I make sure that? A really great example is right now? We are now six months into creating content on YouTube and there are things that we haven't shared yet. And there are principles, there are frameworks, tools, things that we do that I think are a little bit of secret sauce. And there is a part of me that is constantly debating keeping some of that for us. And I just try to think about, like, what Gary does, which is he always puts the audience first. And by doing that, it's amazing what your audience then does for you.
A
That's a powerful principle. And Gary impacted me with that same principle worded this way. That the audience can take away. Because I've seen the video so many times. When Benji Travis was sitting in his office, were you there?
B
I was filming it.
A
So you were filming Benji Travis, the co author of YouTube Secrets, second edition. Now. Now the book is on the table and Gary says this. Do you think about the audience first or don't you? Because most creators are making selfish content. You wanted to go on the yacht, the island and travel. And so you're kind of forcing your audience into what you want. And so we actually kind of expanded that and said service content versus selfish content. And from the idea of even servant leadership and the model of like, are we here on YouTube to serve? Creating content to serve. And this idea, like, your income's always going to be correlated to the amount of value you add to the marketplace. So if you also just lead with service, not even worried about the money too, it comes. Of course, that's big philosophy. I mean, I know people want tactics, but this is a really good way to start off this podcast episode as far as crushing it in 2026 and beyond.
B
Yeah. If you put your audience first, you will win with that audience. Strong 100%.
A
Okay, so that's Gary, but how about Alex? You know, fast forward a few years and we'll get into some nuance of the story. But you are number one@acquisition.com on the content team.
B
On the content team. Mozy Media. Yep.
A
On Mozy Media. At the content team. And so you got to see the inside scoop. But what is something that anybody could apply that they do well or that we could get more views with and.
B
Impact with level of effort to make something really good that you don't have to force the spread of? Other people just naturally want to spread it.
A
Yeah.
B
You got to work really freaking hard on it. Really hard. I watched him write 19 versions of leads that changed my.
A
And what do you mean by watched him write?
B
Like he would write.
A
And what do you mean? Leads give the full title. So it's his second book.
B
Yes, his second book. He would write a version, have that as a draft, and then was like, that was not good enough.
A
Scrapped it or reworked it. Took it back to the drawing board.
B
Yeah. And that like, you know, I've been an editor the majority of my career. I've done version 2, 3, 4, 5, 6, 7 8, all the exports, Adobe.
A
Premiere in the file folder.
B
Yeah. V1, V2. And editors right now, as I'm going up, are dropping off on what they've experienced. V10, V11V. Maybe I've gotten to V12.
A
Yeah. 19 of a book.
B
Of a book?
A
Yeah.
B
That's insane. Right? And so I think what it did is changed my view of what hard work is and the level of effort it takes to create a product that sells itself strong.
A
Okay, so origin story, early lessons. You know, I'm kind of. You're the center of this conversation. And to be honest, the audience is the center because I want them to be thinking about principles and tact takeaways as we go through the.
B
That's what we talked about at the top. We're already implementing and.
A
But I, I want, I. I've got my questions framed for you to kind of take us through this narrative. So where did this all start for you? Take us back to 15 year old Caleb. What were you doing with video in Marysville, Washington? Describe the environment for us.
B
Well, it is nicknamed Smellysville by the locals. So that, that'll give you a little bit of context there. Yeah, I was 15 years old. I was really into powerlifting and I was attending a local church and there was this like, real interesting character, you know, kind of crazy, real creative, real interesting, forward thinking person named Sean who is the director of video.
A
That's a really big title to call me. Director of video. Like, how many kids are in this youth ministry at this time? Like, director of video. I think I'm making maybe $100, even if I'm even paid at this exact moment.
B
I mean, it was, it was the biggest youth group in the, in the city.
A
Fair enough.
B
In the, in the region.
A
And eventually it grew. It eventually grew to almost like 200 people.
B
Yeah, it was, it was big.
A
Yeah.
B
Especially considering our town. Yeah, yeah, it was wild.
A
Way outsizing the town, but maybe at the very beginnings, like 30 kids at junior high or something.
B
Yeah, yeah, yep. And I, I just remember on Sunday mornings there were these very cool, creative and entertaining video announcements, you know, saying, you know, we got the small group thing coming up, we got a potluck, whatever the hell we were doing that was being shared. And I remember thinking like, oh, that's so cool. And I had always been the kid that was messing around with cameras. Like, I remember my sister Victory and I would make funny little skits in our backyard when I was like 9 years old with like a little Canon power shot. You know, they could record like 20 seconds of video at a time. And I just always liked video. And so I remember I, I ended up asking you, or maybe it was somebody else that was also doing the video announcements, but I was like how do I get involved? How can I, like, do the same thing? But because you were doing it for Sunday morning, the main, you know, the adults, the big boys, and then also for the high school group. But there hadn't been anything, I think, established for the junior high, if I remember correctly. I think. Think maybe that was when I came in. It was like you were just starting to pick that up or something. And so I started getting involved with that shooting that Sunday mornings. I'd be sitting up on the platform behind the cameras, you know, or doing the live switcher or more like watching somebody else do the live switcher. But yeah, started that way from that early.
A
Give us any takeaways or lessons. You know, at some point I get. I discover Gary Vaynerchuk and read Crush it. And your recollection is, I told you to read it. Did I give you a copy? You bought a copy?
B
Yeah. What a questionable move for a youth group leader in a church to give a book that has more F bombs than most. No, but it was. Yeah, I remember, you know, you and Spencer were like the cool guys that we all looked up to. And we were like, whatever they do, we're gonna do. Right? And. And I remember you had mentioned the book and you just said, I think you should read this. I think you'll like it. And I started reading it, and I didn't put it down. I read it in, like, two days. And that doesn't sound impressive to most people. A lot of people read books in a day. I didn't read a single book in high school other than this book. Like, truly, like, I would pay kids online to write papers about the books. Hopefully this is not too incriminating. But, like, that was the only book. And so when I read that, I remember when he talked about people being passionate about the Smurfs are going to make money talking about The Smurfs on YouTube, I was like, well, I'm into bodybuilding and powerlifting. I could probably do that. And I remember then it was the same time when you were starting Clear Vision Media and you were doing gigs. I remember there was a Mercedes Benz dealership that sounds so gangster in Seattle that hired you. And I was like, I'll carry your lights and tripods, whatever I can do. And I just wanted to learn. And I remember on those drives, when we would go and do those shoots in your Ford Taurus, I think, yeah, gnarly vehicle. Yeah. We'd be driving down to Seattle, which is about an hour drive from where we were. And I just remember Going back and forth on like, hey, I have this idea of building this YouTube channel around powerlifting and bodybuilding. I'm going to interview powerlifters. I'm going to do it over Skype, which was super innovative at the time. Yeah.
A
Because I had very difficult. No Riverside, no Streamyard, no Zoom.
B
Yeah. None of that shit.
A
Yeah.
B
Like, and you had been doing it for Think Media and you had done a couple. And I remember being like, you know, asking you about it and you told me, vod burner. Yeah. Which I will say this. I downloaded that and definitely thought I was downloading like a virus onto my computer or something. Like it was a sketchy looking platform. Yeah, it was a little janky, but yeah, like very early. Very early. Like, read Gary's book and then I'd look for other resources. And there was like nothing out there. Yeah. Like, nobody. They were talking about traditional marketing shit. Nobody was talking about, like YouTube strategy or anything like that.
A
Yeah. So what are some takeaways before we kind of go to the next season? Because, you know, forecasting, you eventually end up working for Gary and we'll get there. That's crazy. But I do think about. I mean, it's also so inspiring to just see where you've come. We've known each other a long time to, like, see what you're doing now. It's. This is a nostalgic, like, full circle moment for us to be sitting, recording this episode. I'm just curious. Your takeaways though, for, like, everybody wants to blow up in five minutes. Everybody wants. And. And people are as well. People are, like, getting viral success. But what do you think? One of the ones I would highlight is your hunger to learn, your willingness to work for free, which people debate. Your willingness to jump in. Like, those early days clearly shaped your success today.
B
I am only here because of the mentors that I have had. And I've only been able to have really good mentors because unlike most people, and this will sound braggadocious, please hear it through a humble tone. When my mentors would tell me to do something, I actually did it very quickly and then gave them feedback on how it went. That sounds simple, but that is huge for the youngsters, especially listening. Like, if you are the rare human that has somebody speak into your life and you actually do it, they will. I'm speaking from experience. I got a couple of these characters in my life right now and the ones that every time we talk, I'm saying the same thing over and over. I don't want to talk to them anymore. But the ones who are like, literally, they're like, there's this one guy, he's the creative director for a dope brand out there, and literally, I'll get off of a call with him, and within two hours, he's already given me results. And I'm like, my God, you are a savage. And that creates so many. What it does is it. It takes them from just being a mentor to being a mentor who's in your corner. And that is a. That is a wildly different.
A
That's a big. You. You actually just spoke. That is a mentor's love language is somebody that implements. And you then build a bond with that person because actually, they don't really ultimately want your money. They don't want. What they want is your transformation. But they also are sometimes frustrated. To not also sound arrogant and even biblical, but it's like pearls before swine. Like, if I'm giving you my time and I put it out there and then what'd you do with it? I didn't see anything. But if I did it, and all of a sudden you're like, hey, yeah, I went and exit. What's next? Yeah, I finished the book in two days. What's next? Like, oh, everybody I recommend a book to doesn't actually read it. They might even buy it. Do they actually read it? So speed of implementation, actually following through. That's powerful.
B
Yeah. And being willing to work for free. Like, everyone has beaten this one, so I won't do it too much, but, like, your time isn't worth anything if people aren't willing to pay for it.
A
Yeah.
B
The market is. Who dictates your value? Not you. Your value as a human. Yeah. That is real. You are a valuable human. But as far as how you are compensated in the market, like, I hear people that'll complain about. This is a tangent, but I hear people complain about how much they're making right now. I'm like, cool. And how they should be making more. It's like, go out into the market. You'll find out if you should be making more or not. Like, that is the reality of how it works. So being willing to work for free when your time is worth free.
A
Yep.
B
Like, that's a huge one. And a lot of people on Twitter, especially right now, in the last couple years, have, like, demonized it because it does creep into a level where you can get taken advantage of.
A
Like California laws on internships.
B
Yeah. Yeah. But. But here's the thing. The best things in my life have.
A
Come from that Mm, Mine too. I got in the room. I got in the room because I had a camera.
B
Yeah.
A
And I started absorbing wisdom, making connections, networking. And you said in the last episode, one of your biggest lessons, what you'd say to yourself 10 years ago, is that when I'm taking massive action and doing stuff. So when you start getting in someone's four Taurus, hopefully somebody you trust, not.
B
Just a random four Taurus, never getting a random four Taurus.
A
But when you. When you get on a plane, when you get moving, when you. You get a few dollars, but you also get your expenses paid to be flown to the event. And you know what's interesting too? I'm curious. Like, you eventually start Mass Muscle TV, a YouTube channel, but what you. You also. My recollection would be you started the video announcements for the junior high by yourself. I'm. You're modeling and you're getting mentored. But you. That's an entrepreneurial move.
B
Yeah. I mean, you. I. I didn't know how to turn the camera on.
A
Understood. But I'm just saying. But. But you ran with the whole thing at the small level, and then you started a whole YouTube channel at 15 years old that you were the creative director and the CEO of. I mean, that's. That's exaggerated, but it's true.
B
Yeah.
A
It's a very entrepreneurial initiative level of thing.
B
Yeah.
A
Did you always know you were entrepreneurial?
B
I had a dad who was entrepreneurial. He started his own businesses and everything like that. And so I think that was. That was normal to me. I think is actually if I really think about it, like, the people that I was around as a kid, more than half of them had their own business. So I think it was more just like, this is what you do. For me, as a young kid, I was the highly anxious, thinking about my future. You know, at 12 years old, being like, when I'm 18, I'm gonna have a wife and kids and need to support them immediately. So, like, panicking. And I think I always felt like, I. I will have a business. I just don't know what it's going to be. And I remember reading Crush it and being like, oh, this is what it could be.
A
That's what it could be.
B
Yeah. And thank God, because I didn't. I was D's and F's in school.
A
So if we hit Mass Muscle tv, you start it. I mean, you might. You could take us into a narrative where eventually I moved to Vegas with my family. I'm working at a church as a. At a Bigger church as a communications which the only reason I jumped and qualified. I remember Benny Perez said what qualifications do you have to go from a couple hundred person church to a multi thousand TV show multi channel. He has a personal brand. And I was like, well we started this thing called Think International and that got some subscribers a and I been putting in the work and I've been putting in the work underpaid, you know, overworked. But I had those reps and it did lead me to a decent now salary in healthcare to take care of my family. But it led me to a whole level up to a whole nother life. My world got bigger exposure to other people. The move to Vegas location is an interesting thing. Like I think changing locations can be incredibly life changing and sometimes almost essential to reach certain goals that you might have.
B
The two biggest jumps in my career both came on the back of me moving across country. I could not agree more.
A
And for some it might be you literally can't do that because of grandparents and your current situation. However, I think there's others listening where you actually could do it. You're just too afraid.
B
Yeah. And I think there's versions of this like I don't think you have to move across the country. It might look like hopping in your car and drive like I just think like different spaces provide different thinking. And again I'm not a big woo woo guy so I won't go too much further down that I don't know why.
A
No, it's, it's for real.
B
I know that it happens.
A
Get getting out of your environment, certain environments. So give us like the, the Cliff Notes of you start Mass Muscle TV. You're filming interviews with bodybuilders. You're 15 and at one point you actually do come to my house in Vegas.
B
Yeah.
A
And you get on a plane at what age?
B
I think I was like 16 or 17.
A
Did you have a driver's license?
B
Oh yeah. Oh yeah.
A
So did you. How did you rent a car or something?
B
Do you remember we rented a car for you?
A
Okay.
B
And then you let me borrow your Honda Civic. So the Honda Civic.
A
So I'm like, you could drive the Civic, which is my risk or whatever and then I'll drive the rental.
B
Yeah, you did me a huge. Because turns out companies don't want to rent cars to 16 year olds.
A
Yeah, they would not have done that. So your parents let you get on a plane at 16 and fly to Las Vegas to film a bodybuilding show.
B
Yeah. And what's so funny, I had the opportunity to do an interview a while ago with Chris do. And he, you know, as far as I know, he hasn't come from a bodybuilding or powerlifting background. And so I do. That's my whole world.
A
Yeah.
B
But to hear his reaction to it was so interesting. He was like, your parents weren't worried about like you being around all these like, you know, huge roided up, half naked dudes? What? Yeah, but it was, it was my, my whole life. I was backstage at bodybuilding shows my whole childhood. And so it was very normal for me. And actually a funny byproduct of it is anybody who's worked in corporate America or any job knows that like, you know, sometimes you have to deal with your boss being frustrated. Right. And I've worked for some pretty incredibly powerful entrepreneurs who have big audiences, are really well known and are gangsters at what they do. And it'd be very easy to be intimidated in those kind of environments. But what's actually funny is I came up having guys that I was filming squatting a thousand pounds right in front of me. There's nothing that's gonna be more intimidating to me than somebody who's been. Their blood is like shooting through their nose as they're squatting a thousand pounds and they're like, get out of the way.
A
You know, like, it's max alpha.
B
Yeah. Oh, hardcore. And so like, as far as like, you know, ever, like with any job, I never felt like I was like overly intimidated by any managers or anything like that because I had that experience. I also think that because those were the individuals that I was walking up to at 16 and being like, I don't think your videos are all that great. I could probably film a better one. I also was going up to the most intimidating looking characters and pitching. I was selling myself, which is crazy.
A
Yeah, because you're going up to bodybuilding shows, huge guys, you're 16 and you're saying like, can I interview you for my YouTube channel?
B
Well, even crazier on some of them, it wasn't even that, like Flex Lewis, who's local here, he was guest posing at the Washington State ironman in like 2010, 2011. And he was backstage about to go on stage and I just was like, hey, I really admire what you've done and what you've accomplished. You have a crazy physique. I would love to film a video. I think I can make it really good if I film you backstage here, when you go to dinner afterwards, you're going to leave. I'll edit a vlog and if you like it, maybe we can work together. Did it. And then ended up getting hired to work with him for a while.
A
And so then he hired you to make YouTube videos for him?
B
Well, actually even crazier. Weeder Ami American Media Incorporated, they owned. I don't know if they still do, if it's even a thing, but Flex Magazine, Flex Online hired me. They were a publisher to go out to at the time, Murfreesboro, Tennessee where he lived and film Flex Lewis week. So again, 17 years old, flying to friggin, you know, Murfreesboro, Tennessee and filming with like these two dudes that I don't know. Him and his training partner, you know, crazy.
A
Would you call these sales skills? Have these sales skills translated in serving you today? At least the boldness or the raw audacity to step out pitch.
B
I probably have a weird belief around being good at sales. And I as a creative, I think probably somewhere within me I feel kind of like squirmy when you say that. And I also. There's so many people that are actually really good at sales that I wouldn't lump myself into that. I think what it is is probably out of ignorance. I've been fairly confident not in myself as a human, but in the product I deliver. Like, you know, anybody listening to this doesn't realize most of you fitness is huge now. It's like one of the biggest industries out there. But back when I was doing this, it was tiny. Nobody gave a shit about bodybuilders or powerlifters. Not at all. C Bum is huge. Phil Heath, when he won the Olympia, was a big, big name in like the broader fitness world. Like nobody knew who Dennis Wolf was, right? Like nobody knew.
A
I don't know who any of these people are, but I get your point.
B
Like it, there was nothing in there, there was no money and all of the content sucked. I was a consumer of it. I was a powerlifter. And I watched all the training videos. They were great and entertaining, but the quality was like bleh. And I thought I could do something better. So I had like a high level of confidence in the product that I was delivering.
A
Got it. And, and, and that's what it is. I think a big opportunity for listeners is okay, you get in, you get mentored, you start getting some experience with the camera. Then you also immerse in the world you're already in and that, you know, you also studied. You studied that world because you're living in it. You saw difference that you could add to the world. You had built up enough skills so you just knew what you could offer. You had also developed a level of confidence. And you don't call it sales, but at least a level of boldness to just pitch, give them a sample and give out even free content. Give something free. And then that translated to business even before you were 20.
B
Yeah. And as you were saying, all of that, the thing that just kept hammering in my head, because it's what I do now is like, I just feel very confident in the product. And so I think for anybody who is like me, that has an aversion to sales and feeling salesy, if you make a really good product, you're not going to be salesy. In fact, when I do a discovery call, my whole goal is to unsell you. Here's all the reasons why this doesn't make sense for you. Because I'm just wildly confident in the product and it takes away any sort of weird. So, yeah, I think that would be the answer.
A
So bridge us to Gary Vee. There's a lesson there. You do move, you do some other stuff. There's a couple building blocks.
B
There's a big lesson that we'll hit real quick.
A
Okay. And then. And then that'll lead us to you moving to New York.
B
Yeah.
A
Okay, so. But what happened next? One of our Secret weapons for YouTube success here at Think Media is Vid IQ. They make it super easy to come up with video ideas that get views, optimize your videos. And the new suite of AI tools has been a total game changer. And if you haven't tried Vidiq's AI Coach or video idea generator yet, you've got to check it out. The truth is, creators that have better tools have an unfair advantage. So if you want to accelerate your channel's growth for just $1, hit the link in the description down below and start using Vidiq today. Now let's jump back into the video.
B
So after the bodybuilding era, I actually hit 18 and was like, wow, this whole doing your own thing is wonderful some months and really awful some months. And I'm a big boy now and I got to move out on my own, and I need consistent income. At the same time, there was an opening at Logos Bible Software, and I went and worked there. I worked there for about three years, and I learned a ton. Took the same approach that I did with you, and I just applied it there. Zero ego. Ask all the questions. I'll carry lights. I remember Josh Gray. I went up to him and I was like, dude, I'm an editor on the team. I'll edit after hours. If I can join you on shoots and just hold the lenses for you. Just tell me why you're changing from a 35 to an 85 every time you do it.
A
What was happening in your mind was that tracked to an ambition that you had to just advance or eventually be on those shoots?
B
I think at some level, I knew early on that one day I wanted to lead a creative team, and I didn't want to be that creative leader that thought they knew the language, but was speaking a completely different language. I wanted to know what everything took. I'm not going to be the expert at everything, but I want to speak the language and know, like, if I ask you to make this graphic edit the night before we're shipping, I actually know what I'm asking you for, you know? So I think I was just trying to acquire all those skills because I knew it would come in handy later. I was also just interested, like, something that we didn't hit on. We started with video, but I was the weird kid that, at 10 years old, was trying to figure out what I was gonna do for the rest of my life. And I just tried a lot of shit. A lot of shit. And once I figured out video was the thing within video, I tried a lot of shit. At Logos, I was a text editor, an assistant editor, a motion graphics artist, a grip, a dp. I did a bunch of different roles there to figure out what I liked. And I determined that I liked editing. And then a crazy thing happened. Logos had a really significant layoff. They laid off. I think it was like 30 or 40% of the company, and I was part of that.
A
Wow.
B
And I remember being like, oh, shit, this is what big boy life is like. Oh, my God. Now, I was living in my van at the time because. And we don't have to go into this, but I was really into hiking and Instagram photos and all that shit. So I chose the van life. I was looking around at, like, people that have, like, families and mortgages. So it wasn't like that big of a deal. I was like, cool. I have no expenses. I live in my van. I'll be fine. But what happened out of that was that's when I learned the lesson about being in constant motion, because that's when I was 21. So the question that you asked on the previous podcast, the 10 Years Ago, that was that the moment this happened, all my friends were like, hey, you should just, like, take a second, figure out what you want to do next. Don't rush into the next thing. And I was like, sorry, but that, like, I'm rushing into the next thing immediately.
A
Yeah.
B
And I didn't know what that was going to be. I didn't have any clients, so I was like, I'm going to create a podcast. In creating the podcast that I never ended up releasing, the second guest I had on ended up introducing me to, who ended up being my client. For the rest of that year, I worked with two i502 cannabis companies in Washington state. The year that cannabis was legalized, we did the first Facebook campaign, paid campaign for cannabis that was wildly difficult to get around. But again, another day. And then in being in this action, my best friend, who, you know, Jordan Villamorph, texts me and says, hey, there's the photo that Gary posted on his story saying that he's looking for videographers. And I at the time had done what Gary tells people to do. Stop watching my shit and go do.
A
Yeah.
B
So I wasn't consuming anything, so I didn't see it. Jordan, you know, there has never been a time in our relationship where he's been like, you should go do blank.
A
He saw that message, you, you got to do this.
B
Yeah. And I just was like, what on earth? He's not that kind of character. You know, I'm the friend that tells my friends what you should do or whatever. Because I think I. He never does that. So I was like, cool. Immediately took action. Within five minutes, I had already recorded a video and sent it to Drock. And so I just, through the process of following up over and over, went through that and then eventually got the opportunity to work at Purewow, not Team Gary. So I started at his publishing company called Purewow.
A
That required you to move, correct?
B
Yeah, Like I had two weeks.
A
So you get hired, you moved to New York? Yes, New Jersey.
B
New York, Queens.
A
How much was your apartment?
B
Great question. I lived in a three bedroom apartment that was probably, I'd say 1,000 square feet. And I paid 1850 for my bedroom.
A
For your bedroom?
B
For my bedroom. We were all paying 1850.
A
Bang sharing. So three roommates total?
B
Yep.
A
Did everybody work at Vayner something?
B
No, no, no, no. I didn't know these people. Like, so what I did is even when I was severely broke, it worked out. I wouldn't recommend it. I always chose convenience and time over whatever was cheapest. So, like, I could have found a cheaper scenario. But what I did, I don't know if they're still around, but the Company was called Common and they just. You could sign up for a room if you pass the background check. Cool. You're in with two other strangers.
A
So that's what I did. And you also wanted to be close. Did it put you really close?
B
No, it was. It was an hour and ten minutes away. Geez. Yeah, that's all I could afford. Like any. Every 10 minutes you get in, you could add another $200 to the rent, basically.
A
That's wild.
B
And that's actually probably fairly accurate that I think about it. But yeah, I did that. Did a six month lease, ended up renewing because it was also furnished and everything. So it was just like I got rid of literally everything I owned, which wasn't much because I was living in a van, but. And I just shipped two boxes of clothes out there and then moved.
A
So how long until then you transition over to Team Gary? And how did you make that transition? Why'd you get noticed? Why'd you get the opportunity?
B
Yeah, the interesting thing is I was hired at the same time as this other character who also loved and admired Gary and loved and admired a lot of the characters on Team Gary and this individual. And I chose two completely different paths. I love them. I think they are awesome. They're a killer at what they do. So this is not a reflection on them in any way. We both were hired at Purewow and I actually on my Instagram, there's literally footage of my meeting with Gary, my first meeting. He offers. He has an open door policy and I was like, like, screw it, I'm gonna take him up on this five minute meeting. And in the meeting he tells me, you know, I know you're working up here. Well, but like after 5pm, my team is still here. A lot of people leave the building. My team's still here. You can come up, hang with us, we'll give you some edits and you can work on that in your aftertime. I'm sure you don't know a lot.
A
Of people here and would that be for free?
B
Yeah. Oh yeah, totally. Yeah. And I remember leaving and being so fired up to do that. And then I was on the subway and I was like. And I respect Christianity and everything. I don't personally practice, but this Bible verse that I will probably butcher was just like flashing in my head. It's something to the effect of like being a good steward with what you're given. And I was given a job at Purewow, not Team Gary. And so I actually on that ride was like my free time is not going to go to Team Gary. It's going to go to making better.
A
Purewow content or without being paid overtime. You thought, I just want to steward this, max everything out.
B
Yeah. Literally the words paid overtime have never come across my eyes or brain. I've literally like you saying that is maybe the second time somebody's ever said that towards me. I've never thought about being paid overtime or whatever, maybe to my own detriment, whatever. But yeah, I just chose to do that. Now I will say living in New York City, coming from a small town when you don't know anybody and are working really hard is difficult and emotionally volatile. So I did take some time to do like passion projects to, as Gary says, get my creative nut off so that I could still exist as a human because that's what I need to do in order to get myself out there. But other than that, my free time went towards PureWow. The other individual spent every moment after 5pm and I would argue a lot of moments before 5pm hanging out on Team Gary. They would ship their projects for Purewow last minute or late and they were doing a ton of stuff with Team Gary.
A
The main thing suffered for the side thing, basically.
B
Yeah. And in theory you'd think that's the right path. But that person did not get pulled onto Team Gary and I did within nine months because I kept pushing into Purewow and was trying to build the brand of like Caleb can do it. So that when Ryan Harwood or Mary Kate McGrath when they would think about like we have this weird unique video project that it doesn't really fit for the brand team and it doesn't fit for the social team who could.
A
Caleb could do it like a Swiss army knife.
B
Exactly.
A
Which is the exact character that needs to pull off a show like trash talk later or something.
B
Yeah.
A
Like somebody who's a shredder, producer, shooter, editor, storyteller.
B
Yeah.
A
And that was a skill set you had developed. So what's interesting is man, this thing of like creatives being pulled in so many directions, having a little bit of a side hustle. But this is a big epiphany of on the journey really identifying your priorities. And the thing that like, like the no lose the no fail list, like who, what, what thing do you need to steward really? Well.
B
Yeah.
A
And the extra might not be, you know, maybe should not be divided focus from that thing in your case. That was a big lesson.
B
Yeah. It's weird too because I never would have called myself a really focused person, but Looking back in hindsight, I think I was there. You know, there were times in New York where due to my poor financial planning and not crazy high income, I was broke. And so I needed to do a side gig in order to be able to pay rent or eat. So I would do that. But other than that, I really kept pouring my. In a world where if you're on Team gary, you're getting DMs for really premium consulting calls for a one hour call where you just tell them what you're thinking and that's it. I was getting a lot of those requests.
A
Does he care if people do that?
B
I doubt it. I never have even asked him. Like, I personally just never needed to do that. I did two side gigs when I lived in New York. One of them was with SLT strength and length and tone. But yeah, I, I don't think he would care. I think as long as it didn't interfere with the work, you wouldn't give a shit. I just always felt like, okay, I could do that and make a little bit of money right now, or I could do this, make no extra money, but build my reputation further. And I think early on, before anybody would have labeled me like the brand guy or whatever, I understood, I never could have articulated it, but I understood brand at a really high level and was applying branding not externally but internally within the organization I worked for.
A
What do you mean by that?
B
I believe that all of the elements of personal branding that people do publicly, employees should be doing privately within their own company. The content you put out within the company is the slack message or the emails that you're sending.
A
So are you talking about you were just intuitively building your own personal brand? And are you talking about your reputation, your character, your consistency, your trustworthiness? Caleb has a brand that what you had done at Purewow was why your name came up and it was like, yeah, we can bet on him.
B
Yeah, I mean, I would argue it was probably like, you know, oh, Caleb came through on this, Caleb came through on this. And an equal amount of. Caleb is really obsessed with Gary and Team Gary and continues to deliver on this. And I think it was, I mean, I don't know, I wasn't in the room, but I'm sure those things had played a role in it. Yeah.
A
So if you, if you recap some of the lessons then and you think about, I mean, if we stay on mission here and we talk about how we built million dollar brands from a small town and you're going through these stages, you're learning lessons along the way. What are practical takeaways that anyone could apply from being in New York working with Gary that, you know, become the building blocks of any career that a listener wants to build.
B
I'll give you kind of a unique one. Doing the right thing is always the right thing with your employees. We're in an interesting time right now where. And I reference him a lot because I learned a ton from him. Where Gary has been in business for long enough that there are characters way cooler and doing way bigger shit than me that are out there doing their own thing that have such positive feelings towards Gary and they're going out and being gangsters and killing it in the world and pointing back, back to him. And I think that is like a, you know, this whole creator world is very new. Right. Like YouTube's been. They just celebrated 20 years, right? They're about to.
A
Yep.
B
20 years. 20 year anniversary this year, right? Yes. Yeah. Like, that's not like YouTube can't even drink.
A
Yeah.
B
You know, so the amount of companies that have been built in this public YouTube world are very few. And the amount that are at a mature level to where the people that have worked in that organization then go on and build their own thing and can point back positively. It's small. But another person that has that is you.
A
Yeah.
B
You've had gangsters on your team that have gone out and they're building their own thing.
A
Yep.
B
And doing it very well.
A
And so you're. Is it true to say how you treat people?
B
Yeah. Doing the right thing is always the right thing. Like that's the Gary quote that, like, that sticks with me so hard. And I try to think about that towards the audience, towards my team, towards my partners, like everything. And I think that if you operate that way, you're good, human. But also a byproduct of that is there's a lot of good reputation to be gained by having. If you believe in brand the way I do, that's just pairing in reverse. Right. Like I'm not doing that much of a dent by any means. But the fact that I go around talking about how great Gary is doesn't hurt him.
A
Sure. And it's this one conversation that some individuals are listening to. It's the ripple effects. You know, someone that just had him, Neil Dhingra, who had him speak it Forward conference said, he said he basically was like, a lot of people have followers on social. A lot of people have maybe even bigger. Not many people have bigger numbers than Gary in the entrepreneur space, but they've got big numbers. They also have a lot of people fake the funk and have purchased things or their engagement's not there. But even if they built the following. He said, but when it comes to actually being an event, a lot of times people are not as excited. The line to meet them is not very long, if it even exists at all. But Gary Vee has real depth, real super fans and the depth of the super fans. And there's something there, you know, people might think, like, we're, you know, over. What is the Gen Z word for, like, riding on someone's.
B
Yeah, I have no idea. I don't Gen Z lingo. Like, I don't. I don't know it and I'll never.
A
But we, we just communicated the point. But I mean, we're just. I mean, it's this. This individual crush it 2009, you know, and. And his subsequent influence. And so the, the principle is you want to be that kind of person, and you want to be that kind of person, how you treat people, but you also want to build that kind of brand. Like, how do you build that kind of brand where you are that meaningful to individuals?
B
Yeah. And. And the other thing that, you know, people that run events, like Neil, for example, probably wouldn't say, but I know they all experience it, is there's people with half the audience size that are way less considerate backstage to the crew, to the fans or audience or whatever you want to call them to the promoter.
A
Like, they got ego.
B
Yeah.
A
They think they're.
B
Meanwhile, like, when I worked for Gary and this even happened when we went back and filmed with him for the return of DailyVee. Like, I'm like, gee, we gotta go. We're gonna miss the flight. And he's like, yeah, but like one more selfie. Like, he actually, he doesn't. He's not faking it. He actually cares about the audience on a wild level.
A
Okay, so we're kind of coming into this last phase. You know, fast forward to today. You're. You've built this company, you're out on your own, but you have a big shift. And there's some steps towards that shift. But eventually you end up in Las Vegas working for Mozy Media. But what were the steps to get there?
B
So the lesser talked about season was after Vayner because I was on Team Gary. Then I transitioned onto the Vayner side of things, agency side. Then I went and worked at Constellation Brands. Crazy timing. We were building out. I was part of the team building out the direct consumer division. In a company that owned Svedka, Modelo, Corona, all Kim Crawford, Robert Mondavi, all of these liquor, wine and beer brands. Right before COVID it was crazy time. Like, it was absurd. So I did that for two years. And back to the point that I told 21 year old Caleb, I got to a point where it was. I mean, Constellation is a massive corporation. They have over 11,000 employees internationally. Like, they're huge, right? They're a Fortune 500. Like, they're publicly traded. They're huge. They own Corona Beer. They're massive. And because of that, the way that they're structured is like I was mainly for two years shooting bottle shots, like photography and editing clips, because this was during COVID So, like, I couldn't film with any talent or anything like that. We weren't allowed to do any shoots. So I had to use like stock video combined with like trying to create similar looking environments in my home and filming like little bottle shots that I'd intercut. Like, it was. It was so weird. And I got to a point where I just. I learned a ton for the first chunk. And then I just started feeling like I was stalling out and not growing. And a lot of people in this position, they end up blaming their boss and the company they work for. And don't get me wrong, I had moments like that where I was like, you know, getting frustrated or whatever. But the reality is, is my boss was awesome. Like, I love Stu. It was not his fault. It was my fault. And so I took ownership over that. And this is when I am in Marysville, Washington, on a random trip.
A
Yeah.
B
Sitting on your front porch, you, Kyle and I, and we're sitting there talking. We're talking about a conference that you're going to put on and everything that you had Gary come out to. And then we're also sitting there talking about my newfound passion around Harley Davidson's and riding motorcycles. And you were like, you know, I mean, it's probably a pretty hefty payment you got on that. You could probably like, you know, write that off if you had a business making content around it.
A
Yep.
B
And my $330 payment a month, I was like, oh my God, that's interesting. That is fascinating because in addition to a very expensive payment, I am six, seven. So I can't ride a stock. I mean, I can, but it's not comfortable. I have to modify it a lot. So I was like, man, with all the parts, I could probably do like bartering in exchange for content. So I ended up Doing that with my best friend Jordan, the one who recommended that I do the Team Gary route. I ended up moving to Portland and living with him and him and I built this little side project called Wild Media. And again, very similar to the fitness era. I looked and I was really into Harleys and I didn't see any content that served me. Like, I love Harleys. Sport bikes are cool too. And sport bike culture, I kind of like dig a little bit more. The Harley culture that I was aware of was like, and I love these guys to death, but like the hell yeah, brother. Like, you know, old school guy with the half cap on, you know, rolling down with the fishtails in the back. That was not my vibe. And so I saw an opportunity to create content in the Harley world that was not geared towards the 40 and 50 year old Harley Rider, but was the 20 to mid 30s writer. And we just started making somewhat of a little bit of a splash. Nothing crazy, but I probably did about $60,000 worth of modifications to my Road King special and probably spent maybe two grand to get all that done.
A
Because you started an Instagram account?
B
Yeah, we made an Instagram account. We were making content and we would make content and post it on ours, but then we would also make like ads that they could use or whatever. And it was working really well. And I just started meeting a lot of people in the industry.
A
And how were you paying your bills?
B
How was I paying my bills? I was still working at Constellation.
A
Okay, so you're working at Constellation.
B
Yes.
A
Got a big principle here, is always kind of main hustle, side hustle, and always kind of building skills up. You're scratching your creative itch. Not that everybody has to do that, but this is your path to eventually becoming who you are today.
B
I would say the side hustle is actually not always the right move. What it was, in one man's opinion is I always want to be working on something I'm very passionate about. And if my 9 to 5 is no longer that, I need to build something on the side that could eventually become my 9 to 5. And that was the idea was like, maybe we could build Wild Media into this thing that we do full time.
A
Yeah.
B
And that's, that's what we are. And I started learning that the best, not the best, but a good concentration. Especially at the time of Harley Davidson, stunt writers were in Las Vegas, Nevada. One by the name of C Bear stunts on Instagram. As a side note, everyone should go watch. He'll take like a, you know, 850 pound bagger Harley bagger and go like 90 miles an hour down the 15 here in Vegas. It's absurd. Dangerous too. Don't do it at home. But I was like, well, shit, it would probably make sense, Jordan, if I move there and start filming with those characters. And so I did. That was the only reason I wanted to ride my Harley more and film people doing wheelies.
A
And could you work remote for Constellation?
B
Yes. And this is where Stu Karns went to bat for me. You know, it's a large organization. They're like, why are you moving? Like, well, to ride my heart. That doesn't really make sense. And they have a lot of, you know, HR stuff and whatever. Stu advocated for me hardcore and came through for me and I was able to move so, like, huge shout to him. But, like, the reason, and this is why this podcast is so wild to me is like a huge reason why I'm in Vegas is because of that conversation we had on the porch. Yeah, that's so. It's like multiple instances in my life where you've been like a. A firestarter, you know? Yeah.
A
So you move to Vegas and then how. How does Mozy Media hit your radar?
B
Yeah. So there was just a mutual connection that we had. And Alex and Layla were starting to take content even more seriously than they already were, which was pretty serious. And they were like, we need a drock. And I remember hearing from my buddy Jason, long story, they were connected, all this stuff. Anyways, Jason finds out that they're looking for somebody to do this in Vegas and he's like, oh my God, Caleb just moved there like a month ago. What on earth. This would be perfect. We meet and everything went wildly good. We had a conversation around the idea of having a videographer, a drock. I love that. That's a thing. Like, it's crazy.
A
Yeah.
B
David Rock. And what we realized is it's not just that, like, you guys aren't just wanting to make like, you know, vlog style content. You guys want to build a media team. And we need to do this in a way where it's going to scale. And that's what they were looking for. And so, yeah, rest is history.
A
So you printed a million dollar business that's you're running right now. It did not happen overnight.
B
Yeah.
A
And all of these, I think this also just speaks to, I mean, similar people. People that have worked for think media have done the same now. And but what's cool about that is also it didn't happen overnight. Like that story with Omar is Like over a decade and it's stuff he's school, church projects, different things, collaboration. And so as we're pulling out these different lessons, you know, for the sake of time takeaways and some takeaways from Mozy media takeaways. You had a lot from Gary. Different things. But what are those bigger principles for people at all the different stages in their journey? Like when is it my time to jump out? Do I jump out now and go on my own? Do I stay planted here? Do I need more skills for a while? I think there could be a time where it could have been too early. You maybe could have done it earlier but there was personal desire to really follow through. What are your thoughts for somebody else that wants to start their own thing or build a six figure multi, six seven figure business?
B
Well, I will tell you the joke amongst a lot of the characters who are behind the scenes of these bigger personal brands is when I don't want to, like you said, go too early and then like the biggest thing with the brand happens two months after I leave. Yeah, it's like investing. You don't want to invest. Trying to predict where the market is going to go. You will lose. I think what you need to do is figure out am I still learning? Is this an environment where I'm still learning? And the moment that you feel like you're no longer learning at the rate that you want or being given the opportunities or challenges that you seek, that I believe is the moment when you should move on.
A
It's called a lid. Right. It's actually you hit a lid in that organization and so you maybe you're finding some place that could expand. And it's also maybe a self awareness question. You also might be like, I love this. I'm happy. It's a good thing. The season of life I'm in. So what are your ambitions? What are your goals?
B
Real quick too. One thing that I will also throw out there is I would be very careful about how you time when you go out. If you go out on your own and within the first three months you really need money, you're going to build something wildly different than if you don't. Like I was fortunate enough to be in a position where I had a good amount of expenses saved up. So like I could have not signed a client for over a year and then totally fine. Not stressing. I mean it would have not been ideal. You know, we'd be burning through the oh shit fund. But I had, I had put myself in a position to where if I wanted to try something that could be a reality and I could build it in the way that I'm gonna be proud of in 10 years, not in the way that allowed me to eat today.
A
People have a tension between confidence. You're completely confident in the product you deliver now.
B
I mean, very. I would say maybe not completely. Yeah, yeah, yeah. 99.9%.
A
99.9.
B
Yeah.
A
Okay. There's always. But you said it earlier, you knew the quality of the product you could deliver to the bodybuilder, and now you're selling clients and you're doing great work for people. I mean, your experience led to that. The trenches you were in, the things you had done, the wins you had gotten. I'm just trying to extrapolate some principles. Is that one of the big building blocks? How is your portfolio full enough? Do you have enough reps under your belt? Do you have enough different environments under your belt? Or could you have launched this consultancy maybe earlier and you. You could have, you know. Do you think it was a half organic or half. Like, when you're ready, you do it, or is ready a lie?
B
I'm not that person. I'm not that person. I think that there is a time when you're ready and there's a time when you're not. I think what it was for me, and then maybe I can try to extrapolate a principle that would apply to anybody. For me, it was after working for Gary, sure, I had ran the TikTok account, sure, I had been the editor of Trash Talk, but I'm not the guy behind Gary, you know, like podcasts. And I understand. Have me on and they'll title these podcasts like the man behind Gary Vee. I joined Team Gary 3 1/2 years into it being a thing. Yeah, Like Andy Cranack, David Rock, Tyler Babin, Sid. Like all these Iris, like all these other characters came before me. If I would have gone off to do my own thing after that, I think there'd be success. But back to the example that I gave with Billie Eilish. I think on our previous episode of if she hasn't given me reason to believe that she's a good educator, why would I pay for her to teach me how to be a good singer? I had not proven that I could build something right. I had proven that I can come into an incredibly flourishing brand that was already killing. It already had insane momentum, and no matter who was running his TikTok, it would have done well. That's the reality.
A
There it is. And so when you join mozy media as creative number one and then built a team, it was a whole nother set of skill set.
B
Yeah. And proof to show like not only team building, audience building, audience building in a way that actually converts. Right. Like all of the things that I talk about now are things that I can point to how I did it.
A
So if you're going to build a seven figure business in an ethical way, because there are shiesty people who like hack numbers like that and as high as they rise they also fall because they do it unethically. But if you're going to do it in an ethical way, what I'm actually envisioning. Envisioning is a skill tree in gaming, in cyberpunk, a lot of different games. Sometimes it maps in different directions. It's like how good are you at arms? How fast are you? How you know in some games, how much magic skill do you have? And the character needed to sustain a seven figure business is no joke. There's something like overnight success takes 15 years. And so to me that's sort of how I see your, your you, you, you did. You parachuted into a team, learned a lot there. Faithful appear. Wow. Did a lot there stewardship over here all the way Back to Marysville, WA180 like cutting videos and then over time and we don't know the exact moment but you could have done it too soon. I do have kind of like one final question. We'll give a shout out and we'll land the plane. You're not name dropping anybody here but you've gotten to work with other people that have been on these teams, mistakes they've made that you've learned that maybe they left, they did it wrong. So we wouldn't even know who the person is. But I'm just curious, you know it's like they left too early or they tried to. They kind of did it wrong. Stealing the credit a little bit. Is there any stories like that like that'd be like the anti mistake of like they thought they could launch a business or they also thought because like sometimes when you're in proximity to the. Gary already had the momentum. You did TikTok stuff but he had team and he had some other things. And sometimes when you're in an environment you think you can jump out and do it on your own. Can you really? And you step away from the force that is that individual, that brand or that organization.
B
I have an incredible answer for you.
A
Here we go.
B
This is something that not one individual but many individuals have done. So I can feel good saying it. If you are working in house for a media team and you have a fairly high tenure in this company, a trap a lot of creatives can fall into is becoming the best creative, best videographer, best editor, best strategist, whatever for that brand. And what they don't do is learn how. They learn tactics. They don't ever step into principle based learning, meaning they have great success at their current org and they step into another brand, another company to try and do the same thing and are completely incapable of replicating any sort of even remotely close results. If you want to know if somebody is actually really, really good at something, they've done it in multiple different scenarios. So for me, I'm a verbal processor. So another thing that I would add to the answer of the previous question is that if I would have stepped out from Gary, I didn't show. Obviously I mentioned the ownership and building it, whatever, but I wouldn't have been able to show you that I've done this in multiple scenarios with different types of people in different ways.
A
So at that point it was too early. You know, Neil Patel told me this quote, if you wanted to hire the right executive, that basically would be guaranteed to make the thing you're going to put them over a success. He summarized it in one quote. He said, it's super easy. Just hire somebody who's been successful twice. And that challenged me too, because as I even think about our team, like many of us, we have a lot of background, but as we pioneer our current executive team, like Brian's a director of coaching, I go, how many coaching programs have you built? He goes, none. I go, me too. I haven't built any million dollar companies. This is my first one, you know, and so there is a tension between. You're just like right there on the bleeding edge wondering where your leadership is. But there's also the tension of like, how many wins do you have under your belt? And a mistake from a leadership perspective is of course you could take a risk on somebody, but you got to know it's a risk.
B
Yeah.
A
You go, how many times have you done this? Never. All right, well then the future is totally unpredictable. Once you might have got lucky. If you've done it twice, it's probably really likely you could do it a third time.
B
And that's what I'm aiming for in this next season of my life is that third one.
A
Yeah.
B
And in order, I think it may have been, on the first episode we did, we talked about the brand journey framework My desired outcome is to work with anybody I want, whenever I want, on whatever I want. In order to do that. Yes, two wins. But I would argue they need to be two wins in different industries.
A
Yeah.
B
I have two wins in the same industry. I need another one. And so that'll be what, the next.
A
Five years and you're still on the journey. All right, Shout out to your stuff. If people want to connect with you, where can they find you? And also the part one totally different conversation, all about tactics, building brand. We'll link that up in the show notes. My conversation with Kayla Bralston. But where could people connect with you?
B
The platforms that I am most active on are Instagram, LinkedIn and YouTube. The other ones, you're probably like, you can go there. But I will probably not be posting anything for a little while.
A
And then, final question. We started in a small town. For anybody who made it this far and didn't just jump off because of the way we didn't transition, that there would be a final question. But they're still here. So they're really ride or die gangsters. They're living in a small town. What advice would you give to someone who's just starting and that's in a small town or in a small environment, isolated, alone, in some kind of apartment, listening to a podcast like this, a young Sean, a young Caleb, as they're looking ahead at the future, what comes to your mind as far as the advice you'd give them?
B
I could be wrong, but I don't think I am. The majority of you listening to this are probably making more than $32,000 a year. Probably just by averages, in the US I was making $32,000 a year when I lived in Bellingham, Washington, and moved to New York City. I think you need to move and you need to figure out how to do it financially whatever way you can. I didn't have money. I did not have money. Like, I was barely scraping by right when I lived. I'll share it. I think it's good to share. I was making $75,000 a year in New York City the whole time I lived there.
A
Yeah. Which is nothing. It might sound like a lot to somebody, but not in New York City.
B
Yeah.
A
You had one bedroom. I'll put it this hour, 10 minutes away.
B
I was richer. I was doing better financially on 32 grand a year in Bellingham than $75,000 a year in New York City.
A
Yeah.
B
But I figured it out. Yeah. And the greatest shit in my life came from that. Yeah. And so I think a million dollar.
A
Business came from that.
B
Yeah. Yeah. Like, more importantly, some of the best relationships in my life, some of the biggest impact I've been able to have on other people's lives because of that. The million dollar, you know, whatever. That, that's a, that's a cool side, Benny, but that never would have happened. Said differently, I meet up with a lot of homies from Bellingham that are still running their agency in Bellingham, still doing the same shit. And they all ask me the same question. And I'll give you the way more tactical version of this. You go work for somebody, make them bigger in some meaningful way, in a way that you can talk about, and that's how you'll get there. The reason why a lot of people that we both know and a lot of my day one homies are still in the same spot they were 15 years ago is because they went immediately to agency life and they built their own thing. But the majority of agencies know a lot of the best clients don't want you talking about the fact that you worked with them. Right. And so you can't build your proof off of that. And so I think a fast track for a lot of people is, I mean, now more than ever, every person wants their personal brand to be big. Right. And so the amount of opportunity to go and do this for somebody, learn from them. To your point earlier, I got paid $75,000 a year to learn from Gary Vaynerchuk, to learn what on earth like. And that opportunity is available for all of the people listening. The key is, is everyone pauses right there and they end it. The opportunity to do that for Gary Vaynerchuk is not available for everybody. Like, I worked my face off and got lucky with that. But there are many opportunities with people that are two, three, four rungs up the ladder from you that you can do that for.
A
I'd say endless opportunities. Like the creator economy is so big, brands are so big, the world is so big. If you're living in a small town right now, don't let your small town make you small minded. It's just kind of sometimes hard to see. Oh, there's just not enough out there. There's more than you could ever imagine.
B
Or on the complete opposite end, back to what I said in the previous episode of Use, things that you would call as disadvantages as your greatest advantage, lean into the fact that you're in a small town because of the way TikTok, because of the way YouTube and Instagram are these days. You could Blow up yourself by being the small town person.
A
Yeah.
B
I mean, the amount of famous people that are not in major metropolitan cities, is that the highest it's ever been?
A
It's unreal. Yeah.
B
It's crazy. I mean, I'm not famous. You are famous. But I'm not. But like, look at how many people have come from Marysville. Yeah, that's crazy.
A
Yeah. And hopefully this is an encouraging message. All kinds of different roads we took, but it's possible. And in a 20, 26 and beyond world, it's pretty cool to see what is possible. If you put in the work, you're willing to work, not just one or even five years, but really stick with something and what can happen over even a decade in terms of what you could build. And Caleb, super grateful for your friendship, for the journey, for this conversation, and really thankful that you came on the Think Media podcast.
B
I'm grateful for all that you have taught me and thousands, hundreds of thousands of other people. Like, you're not just the firestarter with me, you're the firestarter with so many people. So, like, I'm not going to cry, but this is a wild moment for me. You were my mentor in high school and you've been helping me all and supporting me all along the way. I remember when we met up in New York City, like. Or. No, it was la. I was with Gary. Great. Yeah, it's weird, man. So I'm grateful to you. Thanks for having me on.
A
Well, thanks for being on the podcast.
Release Date: November 13, 2025
Host: Sean Cannell
Guest: Caleb Ralston
This episode features an in-depth conversation between Sean Cannell and branding/content strategist Caleb Ralston, renowned for his work with Gary Vaynerchuk, Alex Hormozi, and more. Together, they unpack the real journey from small-town beginnings to building million-dollar brands, pulling practical lessons for aspiring content creators who want to make content creation a full-time business in 2026 and beyond. The discussion focuses less on hype/tactics and more on core principles, behind-the-scenes stories, and actionable strategies rooted in experience.
Timestamp: 00:57 – 05:05
Timestamp: 02:48 – 08:07
From Gary Vaynerchuk:
From Alex Hormozi:
Timestamp: 08:17 – 14:28
Timestamp: 16:25 – 21:05
Timestamp: 23:41 – 28:14
Timestamp: 29:03 – 39:09
Timestamp: 39:09 – 44:07
Timestamp: 46:42 – 53:47
Timestamp: 55:38 – 60:23
Timestamp: 62:18 – 65:19
Timestamp: 66:23 – End
"The platforms that I am most active on are Instagram, LinkedIn, and YouTube. The other ones, you can go there, but I will probably not be posting anything for a little while." (65:37)
This episode is filled with rich storytelling, honest reflection, and practical wisdom for anyone serious about turning content creation into a sustainable, growth-driven business over the next decade. If you want principles, mindset, and real-world frameworks (not just viral hacks), this is a must-listen—or a must-read summary.