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Inside A $100m Content Machine: How Top Entrepreneurs Build Million-Dollar Personal Brands w/ Caleb
Chris Do and Caleb Ralston reveal the unfiltered strategies behind the content machines of Gary Vaynerchuk and Alex Hormozi.
Chris Do
Founder, The Futur™ · March 5, 2025
The Audacity of Youth
It was audacious. A 15-year-old kid walking up to titans of the bodybuilding world, men like Ronnie Coleman and Jay Cutler, and delivering a pitch as brazen as it was simple. “I love your [stuff],” Chris Do paraphrases, summarizing the approach. “I'm a huge fan. I don't think your videos are very good and I think I can make a better one.”
This was the opening move for Caleb Ralston, long before he became the architect behind some of the most formidable content engines in business. With the unshakeable confidence that only youth and ignorance can provide, he made an offer these legends couldn’t easily refuse. “Can I vlog you backstage here? I'll make an edit, send it to you, and if you like it, maybe we can work together.”
That one move contains a masterclass in getting noticed. It was not a plea for a job. It was a demonstration of value, delivered directly and with no upfront risk to the client. This approach became a recurring theme in a career defined by proximity to power and an uncanny ability to be in the right room at the right time.
Ralston’s journey didn’t begin in a film school or a marketing program. It began in a church, where he was interning alongside Sean Cannell, now of Think Media fame. Cannell handed him a book that would change his trajectory: Gary Vaynerchuk’s Crush It!. Ralston says it was the only book he read cover-to-cover in high school. “I don't think I stopped reading the moment that I opened it,” he recalls. The message was clear: you could build a business online around your passions.
His passion was powerlifting, a world he knew intimately. His father was a bodybuilder, so the culture of gyms and backstage competitions was his normal. “I grew up like I remember I have this very vivid memory I was like seven years old and being backstage at a show,” Ralston says. He saw a gap. Fitness content was in its infancy, and frankly, “all the training videos kind of sucked.”
So he started filming. This wasn’t a casual hobby. His parents, in a move Do notes is culturally rare, actively supported his entrepreneurial drive. When he proposed dropping out of high school, they negotiated a homeschooling arrangement that allowed him to “work my face off.” They fronted him the money for a camera and computer, an investment he was to pay back. This wasn’t just permission; it was a real-world lesson in venture capital and accountability.
The bodybuilding world became his training ground. The gigs, while not lucrative, were validating. A $200 video for a 15-year-old living at home felt like a fortune. More importantly, it was proof of concept. The audacity worked.
This early run taught him a critical lesson about freelancing. “Freelancing is brutal,” he admits. The feast-or-famine cycle pushed him toward the stability of a full-time job at Logos Bible Software, where he honed his editing skills on documentaries and original content. But the entrepreneurial fire lit by Crush It! was only dormant.
Inside the School of Vaynerchuk
The call came via a friend’s text: a screenshot of Gary Vaynerchuk’s Instagram story. He was looking for creators. Ralston reached out to David Rock, better known as DRock, Vaynerchuk’s legendary personal videographer. After a sequence of follow-ups and sending video examples, he landed an interview and two offers: a role at VaynerTalent or one at PureWow, a women’s lifestyle publisher.
He chose the unexpected path. “I thought that was super interesting that's like the exact opposite of who I am and what my experience was,” Ralston explains. He was drawn to the challenge of a female-dominated organization targeting an audience he didn't belong to. After nine months, Vaynerchuk himself pulled Ralston onto his personal team. What followed was a trial by fire.
“Chris, the most insane time of my life,” Ralston says. “Day three I was told the night before, hey you need to purchase a flight… to go to London for 24 hours and you'll fly right back.”
Working as Vaynerchuk’s videographer was far more than pointing a camera. It was a masterclass in extreme multitasking and operational support. The philosophy was not about creating pristine, cinematic footage. It was about capturing the moment, no matter the cost to technical quality. This is the core of Vaynerchuk's content strategy: documentation over production.
Ralston paints a picture of controlled chaos. “The amount of times that I'm filming Gary and I'm like, this is so embarrassing that we're going to put this footage out… but what people don't realize is the reason why it's so shaky is because we're on the other end.”
The role of videographer was a trojan horse for a dozen other responsibilities. These were the ancillary skills essential for survival on Team Gary.
- Logistics Manager: “I would wheel his suitcase when somebody would come up to him and give them a gift at the airport.”
- Personal Assistant: “I would then hold that while I'm filming. I would also hold his latte and his croissant in the morning.”
- Communications Hub: “I would also be texting on my phone with the admins talking about, okay, we're walking to the event, he's going on stage at 30 minutes, he has a call in 5 minutes.”
- Executive liaison: “I remember there was one time where Gary was running late to a meeting with the CEO of AT&T Global and I had to go into the room and speak to him to stall basically.”
- Unofficial Security: “I always also thought of myself as like an unofficial bodyguard… I was always kind of cognizant of his safety too.”
It was a job that required all of him. Ralston, a formidable 6'7", would sometimes operate the camera with one hand, prop it on his elbow, while his other hand held luggage and a coffee. The priority was never the perfect shot. It was ensuring the engine kept running and that every valuable interaction, every impromptu Q&A, was captured.
The Real-Time Content Machine
The grueling days didn't end when the camera stopped rolling. The post-production process was just as intense, driven by a powerful strategic insight. “We would film all day… go back to the hotel, not only ingest, start cutting clips so you literally post [it] the next day,” Ralston says.
This wasn't just about speed for speed's sake. It was a real-time content loop. Vaynerchuk wasn’t just guessing what his audience wanted. He was actively listening. “He was consuming all the comments, the DMs, the tweets, everything. So he actually knew what people were thinking and wondering at that moment,” Ralston reveals. “He'd see five DMs about the same thing and be like, that means that there's a lot of people that need this. I'm going to hit on this right away, let's get it out tomorrow.”
This methodology explains the uncanny relevance of his content during his peak. It felt like he was reading minds because, in a very real sense, he was. He was using social media as the world's largest, real-time focus group and deploying his content team to serve the demand immediately. This is a strategy many attempt but few can execute with such discipline, a point central to understanding how to build content people react to.
Ralston confirms that the on-camera persona is authentic. Vaynerchuk is just as fast, just as high-energy, and just as intuitive in person. In many ways, Ralston argues, he’s even better. “He's way better off camera than on camera,” he states, citing a deep-seated business acumen and human decency that were often deliberately kept private.
“We would always push more of the business content, please put out more of the business content, and he always would say no,” Ralston explains. “He likes being underrated.” This desire to maintain The Underdog Chip is a key psychological driver. He filmed Vaynerchuk in boardrooms, breaking down billion-dollar strategies for Fortune 100 companies that would lead to viral Super Bowl ads, yet that footage rarely saw the light of day. Like a masterful poker player, Vaynerchuk preferred not to show his best cards to the public table.
“I think there's a lot of value to it,” Do observes, referencing Sun Tzu’s philosophy: “Appear strong when you are weak, appear weak when you are strong.”
The Changing of the Guard
But the digital landscape is not static. What works in one era may not dominate the next. Do poses a critical question: why has Vaynerchuk’s visibility on many social feeds seemingly declined in recent years, while others have risen to prominence?
Ralston suggests it's a matter of focus. Vaynerchuk is not just a content creator; he's the CEO of VaynerMedia, a global agency with thousands of employees, and the visionary behind VeeFriends, a massive IP universe. “I think that there's just been a shift in focus,” Ralston posits. “His attention has gone more so towards VaynerMedia and VeeFriends than the GaryVee brand in this season.”
There is also a platform-specific challenge. The raw, docu-style format of DailyVee, which was novel and groundbreaking, became harder to package for a YouTube algorithm that increasingly favors tightly themed, single-topic videos. “If you have 10 different things that occur, how do you package that in a way that YouTube prefers?” Ralston asks. The answer is, you often can't.
Do offers a complementary theory. As Vaynerchuk’s content evolved, a new player entered the arena to fill the void. “Whereas Gary was giving what I one of my criticisms… very rudimentary stuff which is good for broad audience, in comes this new guy… Alex Hormozi… and really gives high-level, really good business stuff that's highly actionable.”
The market, Do argues, can only sustain so many dominant players in one category at a time. “The universe can only have so many players in one category and so now Alex is just crushing and destroying.” This is a core concept for anyone trying to build a personal brand that stands out; you must find your unoccupied space.
Ralston refines this idea, suggesting it’s less about a direct replacement and more about a natural progression. He calls it the tactics-to-mindset evolution. Most creators, he argues, begin with tactical advice to build credibility. Vaynerchuk’s early content was far more tactical. Over time, as creators interact with thousands of people, they realize the ultimate bottleneck isn’t a lack of tactics, but a lack of belief.
“The tactics are very important, but if the individual doesn't have the correct mindset, they will never actually put those tactics into place,” Ralston says. “Gary occupied this space and then moved to a different space, and Alex came in and thunderously took over that space.” He predicts Hormozi’s content may follow a similar arc over the next decade, gradually incorporating more mindset as his audience matures.
Building the Acquisition.com Engine
In a twist of serendipity, Ralston became the person to help build that thunderous machine. After a stint at Constellation Brands following Vaynerchuk’s sale of Empathy Wines, Ralston moved to Las Vegas. A mutual friend, Ed Turny, connected him with Alex and Leila Hormozi, who were looking for their own “DRock.”
The initial conversation quickly escalated. “Our conversation immediately went from being let's bring you on as our DRock to like, no, we need to build a team,” Ralston explains. The Hormozis understood the investment required. They had the vision, and they were willing to commit the time, effort, and capital to build an in-house media empire from the ground up.
Ralston, who had never built a team from scratch, was nervous. But Leila Hormozi saw the potential. “I remember she was like, you have all the right character traits, you have all the hard skills, I can train you on how to do the team [stuff],” he recalls. This marked a pivotal shift in his career: the move from doer to empowerer.
His first task was to understand the existing system, which relied entirely on external vendors. From there, he began the systematic process of bringing all content functions in-house, scaling the team from zero to 18 people. This process of building an internal agency is a playbook for any entrepreneur looking to scale beyond themselves.
The transition was profound. “I was scared, but Chris, that's the most fulfilling thing I've ever done with my life,” he admits. “I realized I enjoy helping editors grow in their craft more than I enjoyed editing. And I thought when I was an editor, I was like, this is peak happiness… I realized I love this even more.” He had discovered the leverage of leadership.
The Art of the Graceful Exit
The relationship with the Hormozis blossomed into something deeper than a typical employer-employee dynamic. Ralston became family, spending holidays with them and feeling fully committed to their incredible mission. That’s why his eventual departure seemed surprising to many outsiders.
It wasn't a single event but a gradual realization. As the Acquisition.com brand exploded, so did Ralston’s own profile. “The opportunities were getting too crazy,” he says. Brands he had admired his entire life were reaching out. The pull to build something of his own, a dream he’d held since he was a kid, became too strong to ignore.
“I would regret in 5 to 10 years if I were to look back and be like, I wonder what would have happened if I would have tried this idea of going out on my own,” he explains.
His departure is a lesson in professional maturity and strategic foresight. It wasn't an abrupt decision. It was a sequence of open conversations with Alex and Leila. Crucially, he had been building the team for this eventuality all along. This is the concept of a graceful exit infrastructure.
“We were building everything for this to be able to happen,” Ralston says. He had hired and trained creative directors to run the individual teams for Alex and Leila. He had a successor in Michael G. Lynn, a “total beast” from the MrBeast ecosystem, ready to take the helm. The system was built to outlast any single individual, including its architect.
Ralston understood a fundamental truth about high-stakes performance: “I think the moment that [you have] one foot in, one foot out, you got to jump. Because all of a sudden your focus is no longer the same.” He owed it to his team and to the Hormozis to leave before his focus drifted.
Now, Ralston is on his own path, taking the lessons learned from inside two of the world's most effective content machines and applying them to his own venture. He is testing his own chops, documenting his own story. The 15-year-old kid who bluffed his way into the world of legends has become the entrepreneur proving his own value, turning years of observation into a life of action.
His journey is a testament to a simple idea. You don't need permission. You need a camera, a deep understanding of a niche, and the audacity to make an offer no one can ignore.
TRANSCRIPT
I just literally ignored all of these inbound messages it started getting to a point where was no longer making sense to ignore those the opportunities were getting too crazy I just felt like this was the next natural step in my career and I would regret in 5 to 10 years if I were
to look back and be like my name is Caleb Rolston and you are watching or listening to the Future the greatest podcast for creatives pursuing business in general my next guest is a person I don't know that much about but when I met him in person it was just like this big I
would call you like a friendly giant a big man bearded man it reminds me a lot of our chief operating officer Ben Burns and just the similarities there but the little bit that I know about you is you worked with some amazing accomplished people and what I want to do is peel away
some of your lessons what you've learned A View From the Inside strategies that the Regular Joe or Jane person can learn from and and with with the limited resources that they have and what they can learn from you so so Caleb for people who don't know who you are can you please just
introduce yourself and tell us a little bit of your story absolutely my name is Caleb Ralston um I have been in the I guess brand building and digital media space for about 16 years now a character who I think you are familiar with Sean candle I had the wild opportunity to be working
or volunteering in the same church that he was the director of media I was interning and helping with not only the church stuff but his own production company and he gave me a book and it was the only book and I hope that none of my teachers are listening but it was the
only book I actually read in high school and it was crushit by Gary vuk and I remember reading it and I honestly I don't think I stopped reading the moment that I opened it I read all the way through and I remember him talking about people are going to make money and a
full-time income online talking about the Smurfs and I didn't know anything about the Smurfs or anything like that but I remember thinking wow I have some some passions that I'm interested in maybe I could do this and so I read that book and immediately realized I'm into powerlifting my dad at the time
was a bodybuilder and I realized all the training videos at the Time Fitness is huge now but at the time it wasn't and all the training videos kind of sucked [ __ ] and I thought that I could make better ones and so I started filming with my dad uh filming with local
bodybuilders and then slowly started uh getting opportunities with some of the biggest names in the industry uh Ronnie Coleman Flex Lewis Jay Cutler Stan ordine a lot of different characters and I just would go up to them backstage at bodybuilding shows because the way it works is they come and guest pose and
I'd walk up to them the boldness of a 15-year-old and say like I love your [ __ ] I'm a huge fan I don't think your videos are very good and I think I can make a better one can I blog you backstage here I'll make an edit send it to you and
if you like it maybe we can work together and so that just kept snowballing and I got a lot of cool opportunities with that and then I hit the age of uh 18 or 19 and realized freelancing is brutal I have gigs and then I have a month where I have to find
the next gig and I want to move out and so I need some consistent income and so I got a job at a software company uh worked there for about two and a half three years and we were making being a lot of In-House creative uh for the marketing department but we also
created it was a faith-based uh organization Logos Bible Software we created our own Ott to serve that community and so we started creating original content documentaries and everything like that and I was the editor for that learned a lot there um and then from then I went into like a year of freelancing
and this is kind of like the pivotal point in my career here I uh had stopped consuming Gary's content cuz if you follow him he says you know stop watching my [ __ ] and go do execute and a friend of mine texted me a photo like a screenshot of Gary's story saying
that he was looking for creators and to reach out to David Rock and so I just I felt it I immediately reached out to David um through a sequence of follow-up interview like uh emails and everything like that I kept sending videos to him eventually got an interview and then got offered an
opportunity to ID work at Viner Talent OR purewell vayer Talent was kind of taking team Gary and those offers to external clients the other option was perw which was a women's lifestyle publisher kind of targeted towards women 30 to 45 in the midwest I thought that was super interesting that's like the exact
opposite of who I am and what my experience was right like previously I worked at a software company which is typically bro dominated right and this was an organization that was not only targeting and reaching women but also was like 90% women in the orc so I thought wow that just sounds like
an amazing opportunity in a lot of different Avenues I want to learn what it's like I want to have a female boss like I I was very curious what that was going to be like you know anyways I I do that for about nine months and um then Gary pulled me onto his
team and I had the opportunity to work for Gary Vayner for two and a half years as his videographer and that was Chris the most insane time of my life like it was absurd I'm talking like day three I was told the night before hey you need to purchase a flight you know
they were paying for it obviously but you need to book a flight to go to London uh we're going to go there for 24 hours and you'll fly right back like I mean it was just like right away thrown into the fire kind of thing that was incredible I got to run his
Tik Tok we had a lot of growth there I was the editor of Trash Talk kind of a hit series for him and just got the opportunity to learn a lot and then from there he actually sold empathy one wines his wine company to a company called constellation Brands and they were looking
to build out the direct consumer function of their organization they own like sedka Modell uh Corona you know Kim Crawford prisoner all these different uh wine spirit and beer brands and so I went over there to help build out the directing consumer team that was wild I have never worked in a Fortune
500 before you know this was during uh covid and everything and so I was working remotely I was living in Portland Oregon at the time got obsessed with my Harley-Davidson moved to Las Vegas so that I could ride more and then uh about a month after moving to Las Vegas Alex and Lea
reached out and we started talking about how they wanted to build their own team and and build something similar to what Gary had done but in their own way and um kind of the rest is history it was it was an incredible uh conversation that led to the biggest point in my career
which was building out their team helping scale their brand we went from zero people in house to 18 uh at the end there and it was incredible so yeah man that's a little bit of uh the the py statement on my uh Journey what I want to is retrace a couple of the
steps here I was taking notes but you're moving pretty quickly along the story what is it that compels Sean to say you you need to read this book man I me I'm I'm forever indebted and grateful to him for it I think uh I mean I think he read it and realized wow
there's a mega opportunity here that I can take advantage of and him and I were very similar in the fact that like we weren't good students and I think we resonated not only with what Gary was sharing as an opportunity but also the fact that he was the same he was not a
good student he was able to be successful via this new world of the internet and social media that was coming and I think that it resonated with sea and I think he saw something similar in me okay so you have similar personalities similar ways of moving about the world you're in the same
church he sees that you're producing videos he's producing videos and he's like you got to check out this thing and then you're like you read it and it changes your life and it sends you on a path I'm going to jump around here I mean this is a unusual background you're into powerlifting
your dad's a bodybuilder so you're like there's not a lot of Fitness stuff now it's everywhere as you say it is kind of one of the most dominant types of content that's on social but back then in the Dark Ages I guess everything was new what gave you the confidence to approach these
like Ronnie Coleman is the name I know he is jacked you just walked up to him like you know love what you do what you do sucks I think I can help let me give you this offer and if I do it and you like it where where did any of that turn
into like money oh yeah yeah I mean not much right like $200 for like a p video or whatever but I mean for me at 15 living at home I was like I'm rich right I think my parents did an incredible job of investing in me and helping me understand that like like
I remember I read that book and I told my parents I was like I'm dropping out of high school and I'm going to work and they're like well okay maybe not that but then we negotiated and determined we can do homeschooling so then I can like work my face off and you know
barely do any schooling and just work I think that they gave me so many opportunities to build confidence in myself in that and when I showed interest in this they invested they were like we'll get you a computer and a camera like you'll earn the money to pay it back but we'll invest
in you kind of a thing so I think that's probably where it came also um I think a lot of ignorance I think I just didn't know any better and so I think that's the beauty of Youth is you're not really aware of your invincibility you think you're Invincible right it's kind of
like the whole thing when you learn how to drive that parents are so scared of I just I was audacious yeah I I think that's one of the the great things about being young you're not aware you don't know enough about the the problems the pitfalls and the challenges that you're bold enough
to go forward I think your parents did do something wonderful because this is a rare thing and I want to talk about cultural differences a little bit here most asian-americans or Asians who are listening to this like what I had to get my first degree and my second degree before my parents even
entertain the idea of me doing something weird and your parents like not only are they going to say we'll let you drop by to school sort of technically but we'll homeschool you so that you can get your I think High School diploma I think um and then they fronted you the money for
your camera and your computer so that's not just like we'll let it go but they actually put financial support and allowed you to do your thing I also have to imagine from overprotective parents point of view letting your kid hang around with adult men in like that are half naked there's a scary
thought there too but they're like just go for it we trust you and what what is it about you or your parents that that that's okay and and I want to see if I can listen for the dis inct differences between American culture culture versus Asian-American culture that's super interesting I I love
this by the way it's super cool uh I think one the fact that my dad was a bodybuilder for so long there was a deeper understanding of that culture I grew up like I remember I have this very vivid memory I was like seven years old and being backstage at a show and
uh my parents introducing me to this woman named Molly Molly was bigger than most men you've ever met and I remember her being like hello Caleb and I just you know I was like wow you are incredible and so I like that's something that a lot of my friends would make fun of
or thought was weird and I just that was normal to me right like I never thought anything of that now I mean there are some freaky [ __ ] with that like I like Universal Nutrition they own like animal pack and everything they used to host this event at the Mr Olympia called
the animal cage and they hired me when I was like 16 or 17 to fly out to Las Vegas and film that I went solo now Shawn at the time was living in Las Vegas so I stayed with him and stuff so I think they felt comfortable with that but yeah I mean
they they took some big risks I think maybe in the back of their heads they were like well Caleb [ __ ] up so much with school he's never going to go down that path this is his only shot so help him with it but yeah I think that was a little bit
of that but I think a lot of it was just they were more used to it so I think it would have been a completely different story if they had never had experience with it and I just all of a sudden started going to the gym and met these guys yeah did your
mom or dad ever say hey uh we need to go with you s because you're a 16-year-old kid and we got to look out for you did they help you with the money part or any was there safety or Security Financial concerns at all like you know what you're a big guy you
go out wild and you learn I think so I was also at the same time working at Adidas uh just as like a Salesman and I have always had a beard I mean like I basically was born with a beard I I looked like I was 30 when I was 16 so they
didn't this is technically illegal but I was working more hours than I legally should have been able to so I was working like 38 hours a week at Adidas living at home so I had a lot of at the time a lot of money so I would cover like I would front the
cost for things if I felt like it was a good opportunity for me now the one with Vegas for example they paid for everything so like that was a really good gig that I got um so I didn't ever really have too much concern on that um and no they they never really
needed to accompany me I think probably they I will say my dad did try to get to know like Stan eery was like the best client he was my first real client and unbelievable human and my dad definitely made an effort to get to know him just to make sure everything was good
okay there's a couple different things number one you're you're a power powerlifter your dad's into bodybuilding so this is like familiar culture to you so there's they they know the ins and outs so to speak the behind the scenes stuff so they don't have a lot to be scared of and this is
your world too it's not like you're being thrust into some other world that you're like right what's happening here I just had of curiosity anything sketchy happen where oh maybe this is the right place to be at right now honestly no I mean as far as like safety wise I was always a
big dude I mean these were like huge guys but I I never have had any fears on that to be honest with you um I you know I think that's the privilege of being a 67 uh bearded guy that's bald and looks kind of scary sometimes I'm not but uh I think I
give that impression sometimes I'm glad you threw in there that you're 67 that you look much older like if you don't know Caleb if he walks on the street you might think this is a big dude from a Hell's Angel kind of thing he's got that Vibe but then you instant you talk
to him like no he's just a really super friendly sweet person right so there there are certain kind of physical advantages that you have that allow you to move into the world of adults without you having to feel like oh my God I'm in danger right they're going to think twice try to
mess around with you first okay you get this opportunity to work with Gary did you have to move to New York cuz he's in New Jersey right and well he's in New York he's in New York okay so did you move to New York to work with him I did I literally got
the job offer for Pure wow and two weeks later I was living in Brooklyn okay how old are you I think I was 24 I believe okay so you're there you're making your way um many people know who David rock is by his other name dck who was I think an important figure
in Gary's Evolution as content creator Storyteller cuz he was there filming and probably one of the first few entrepreneurs who were successful had had a crew or a guy at least following him around documenting those stories what was your your role like when you were working with him David's the goat and I
learned a lot from him um basically I was the number two to David so I did a lot of the traveling with Gary for a significant portion of the time that I was there um and helped with a lot of like the technical lead stuff so um when it came to uh any
sort of technicalities on an edit for example I would jump in and help with that um if we needed help I would always make sure to lend a hand to David with filming and stuff like that but there was definitely an effort to try and get David for a season out of traveling
so much so that he could start working more on the strategy and everything like that um cuz there is nobody out there that understands Gary and Gary's brand more than D I'm talking like you could mention a random moment from any daily V and he'll be like oh I remember what day it
was I know where we were like he's an encyclopedia our effort was like let's give him more space to be able to utilize that power that he has so that's when I started to transition more into the traveling and stuff I see so drock becomes like this human archivist who understands all the
stories cuz he was there and has a brain to remember it uh and then you start filling in the role of like primary shooter you're out there shooting take us through for we're going to nerd that everybody so those of you guys are super non-technical go get a coffee or something you'll be
all right so I'm I'm curious because to be a fly in the wall to see how y all work would probably be a thing managing media the equipment that you're using what tell me a little bit about the tools and the workflow because it's got to be insane well I I can't speak
to how they operate now but I'll tell you when I was on the team and I love this it was chaos mhm but we got so much done in the chaos and I thrived in it so um we didn't have like some crazy system for ingesting footage right like what we I started
working on towards the end was building out a dam for us to be able to utilize and tag footage right like he's got years worth decade worth of footage right basically we would film we used Sony's so at the time it was Sony A7 S2s you know um using whatever the equivalent is
now um we did that we used the saniser lavs and um always zoom lenses and everything like that for versatility and really the main priority was not the way that we filmed it but what we were capturing right so like you can see there's so many times where the footage is like super
shaky right and like the amount of times that I'm filming Gary and I'm like this is I know people are going to know that I filmed this because he mentioned my name or whatever and this is so embarrassing that we're going to put this footage out but what people don't realize is the
reason why it's so shaky is because we're on the other end and he never asked us to do this but this is how I like to operate when we would be traveling I would wheel his suitcase when somebody would come up to him and give them a gift at the airport cuz they're
so grateful or whatever or at an event I would then hold that while I'm filming I would also hold his latte and his croissant in the morning right I would also be texting on my [ __ ] phone with the admins talking about okay we're walking to the event the event he's going
on stage at 30 minutes he has a call in 5 minutes that's a five minute call and then right after that he has a 10-minute call and then after that another five minute and then he has 5 minutes to decompress before he goes on stage all of that occurring at the same time
while filming right and I only have two hits so there is a so much more like David and I Jason Marina Tyler Babin we all talk about this like one day I think it'd be cool for us to all sit around and kind of do like a round table and talk about it
cuz nobody realizes the level of effort that a videographer and like Dustin Lee who's doing it now I love Dustin to death That's my boy like people have no idea what he's actually doing behind the scenes there's so much more than just filming you're literally like some trips there wouldn't be an EA
that would join right they'd be back at Hy Hudson yards and so like we were the EA right if Gary is running late I remember there was one time where Gary was running late to a meeting with the CEO of atnt global and I had to go in to the room and speak
to him to stall basically and make sure that Gary didn't look you know like he was being bad or anything like that right like try and smooth it over or whatever and entertain him for a second cuz Gary literally is like 5 minute increments on his calendar all back Tob backs there's no
buffer no break nothing and so like I think the the thing that people can can understand maybe from me sharing this is like if you're a videographer for Gary you pick up so many Anor skills to the actual thing of filming and the priority wasn't the lensing right the framing the the white
balance the lighting being proper it was like are we making sure that we're capturing the moment where somebody at an airport walks up to Gary and talks about how this moment changed their life asks him a question blah blah blah kind of thing I'm trying to visualize this so let's paint a picture
because this is the podcast it's a YouTube episode here's 6 foot7 Caleb Cameron hand is there some kind of rig a shoulder rig or it's just all hand just like this little cage always I always use the strength so that if I needed to I could use my elbow uh cuz my offs
are long enough that I could extend the camera out and hold it like this while I was holding something else literally like there' be times where I was operating the camera like I see strap her on your neck push up with elbow hit record one hand holding the luggage the other hand coughing
and croissant and elbow propping the camera and that's why it is shaky it might not be framed correctly and phone in in your ear probably on on your shoulder and your neck like talking to a coordinator producer EA saying hey he's late you got to get him to hear this is what's going
on right and all all the while shielding Gary from the nonsense that he can do what he does and only he can do yeah s about right yeah and like this was never an official thing but I always also thought of myself as like an unofficial bodyguard like you know I I love
G I love him to death and like I would do anything for him right and so I was always like I was always kind of like cognizant of his safety too right so that's like another element and you can ask all the other video like they were all thinking the same thing too
like there's so many things going youre yeah so you're like multitasking at a very high level and you're doing your thing I'm I'm also guessing that because anything can happen at any time memory cards Galore a system for New Media and safe media so you can transfer at some point and fresh batteries
charge all the time what people don't know is and I want to share this maybe you have a workaround is after the shooting that's just the beginning of the work day cuz now it's offloading the media double-checking to see if it's was good because you want to clear those m cards did you
buy all new memory cards or did you repurpose memory cards cuz some some people have different systems for that like they like they treat it like film they don't they don't use the cards again just in case we would repurpose so we would ingest and and Chris it was crazy SSD with me
I would ingest to the SSD and that was it no other backups not like I yeah nothing like that like it was it was crazy and you're 100% right like we would film all day I'm talk like Gary would do late meetings we'd be down at 11: or midnight go back to the
hotel not only ingest start cutting Clips so you literally post [ __ ] the next [ __ ] day cuz we were especially at that time we were really big on Real Time content and the reason why and I think this is a cool Insight actually that I'll share is Gary like so
many people would comment be like you somehow read my mind and the situation I'm in right now and the reality is is he did because he was consuming all the comments the DMS the tweets everything so he actually knew what people were thinking and wondering at that moment and then he would talk
about it during the day so when we would clip it the reason why we tried to do it really fast is cuz we were literally reading the audience and actually putting [ __ ] out in real time that they were wondering right like he'd see 5 DMS about the same thing and be
like that means that there's a lot of people that need this I'm going to hit on this right away let's get it out tomorrow so like the speed of everything was just on a completely different level you know when I first uh bumped into a piece of um Gary's content I think he
would speak at USC and the the speed of which his mind works and his recall ability was something that was to behold and I remember thinking to myself before I made any content like God how does a person do that is the real life Gary like the one that I see on camera
where he's like I'm ready and goes and just starts talking off the top of his said and he knows how to hit his points he knows the references and he's able to with relative accuracy refer to very specific things Chris what I'll say is he's way better off camera than on camera in
in a lot of different ways so there was so many different things that he did that I just thought were like wow you're a really good human that we would fil and he would turn to me right after it happened and be like never put that out like I'm talking if he was
going to let someone go he'd have like five opportunities lined up for them already I knew that was happening he be like we're never going to put that up I don't need to do that um his business Acumen like people who actually sit down for a business meeting with him to talk about
like private Equity are like holy [ __ ] this dude knows way more we would always push more of the business content please put out more of the business content and he always would say no he likes being underrated uh he likes people thinking that he's just the happiness guy kind of a
thing that dude is 100% like that all the time 100 like he literally when he talks about it and You' probably heard him say it like he walks up on stage and he says hey what's up I'm Gary vaynerchuk and today I'm gonna talk about and that's the moment that he figures out
what he's going to talk about on stage like he he's not preparing or anything like that he just he looking at the tweets of all the people that are at the event what they're talking about he's asking the person backstage hey what has the buzz been at this conference or whatever right yeah
that is 100% how he operates I I I think he's one of those people who is able to make ADHD his superpower because uh the ADH brain as far as I know works much faster and if you can tame it you can literally do that I imagine a couple things number one he
doesn't have time because five minute meeting 10 minute he only had five minutes to like get there and then he's on to the next thing right I remember one time hearing about him in Las Vegas for Sean's event he goes I have to leave I have another event and I'm doing another event
the day after it's like three speaking engagements back to back to back it's like this guy never stops and a few people who have this ability who can harness it are named Gary vuk and I don't know who the other people are so it's kind of very impressive to behold okay and you're
there and you're witnessing all this and you get to see the all the behind the scenes I have to ask you this question why did he not want to show his business side in his human side because it seems like he's very transparent by everything well maybe not everything there's a couple things
he keeps private but why would he want to show that I I genuinely think that he likes being underrated and I think that he always wants to kind of have a little bit of an underdog chip on his shoulder um and so I think like I think that's the the main reason honestly
CU my favorite content that I filmed with him was like the 4ds right I don't know if you've ever seen any of those that is that is Gary and Peak form right like that is just and then there'd be I mean I filmed I won't name the companies but like the biggest brands
in the [ __ ] world I'd be filming him breaking down what their strategy was going to be for the year and be like no you need to do this they' go execute it and it would lead to you know the the most viral Super Bowl ads right like I'm talking really crazy
[ __ ] and yeah he always kept that a little bit more private and I think it's mainly just because he likes being underrated he would always say that he wants to have that chip on his shoulder and he would always talk about how like remember mentioning like being almost concerned about a
day where he's viewed as top and like not wanting that always wanting to you know have something to kind of like build up to almost hm that's an interesting perspective he does say that a lot but unless you know the other side you're never sure as to why he says that and how
much of it is true it's like I like to be underrated I like to be underestimated and I was thinking that's usual position I mean sunzo right like uh appear strong when you are weak appear weak when you are strong right like I I think there's a lot of value to it like
that dude is a [ __ ] business gangster and I'll tell you I know a lot of individuals are also known as business gangsters that have met with him and walked away speechless I want you to put on your content strategist hat right now yeah and be as objective as you can clearly
have a lot of admiration and affection for him but tell us what you think is happening cuz there was a moment when Gary was the only talk in town everything he did was exploding and popping on whatever social platform I've noticed some strange phenomenon the last couple of years I barely see him
on any of my social feeds anymore and his despite his large following some of his videos get less views than ours and we only have 2.6 million followers ourselves what is happening so why did it work and what do you think the challenges are with your strategies at like you have no relationship
with him it's totally objective what's your take I think one it's a sequence of things people don't realize like a lot of people know Gary is the content creator but he runs a massive agency right they have I think they're up to like 12 locations worldwide a couple thousand employees they execute on
multiple Super Bowl campaigns every year for clients working with the biggest Fortune 100s they're the fastest growing independent agency in the world so he has a massive company that he's building he also has this brand called vriends that is the culmination of I think so many different passions and skills that he's had
over his whole life that all I mean let's just call it what it is he got lucky that that came to be like the nft thing at the time that like gave him the ability to build this it's not about nfts in my opinion from my point of view it's about you know
the universe that he's trying to build and everything and he was talking about that [ __ ] way back in like 2012 2013 like he's been talking about this for a while so I think what you're experiencing is and you know this is just my point of view externally this is not anything
he's told me I think that there's just been a shift in Focus so his attention has gone more so towards Viner media and V friends than the Gary ve brand in this scen and I remember when I was on the team there was different seasons where there was different focuses right um there
would be times where it was like hey I got to focus more on vayer so we're going to have a little bit less involvement from me on stuff and then there'd be Seasons where he's like no I have more time to dedicate towards the Gary ve brand so I think it's a combination
of that um and that I I would apply more to like the Instagrams the Tik toks the short form content right then when you go to the long form like on YouTube for example uh and this is I'm not saying anything that she hasn't already acknowledged and said way back when I was
on the team YouTube as you know is a tough platform to package Vlog style content for right if you have 10 different things that occur how do you package that in a way that YouTube prefers right YouTube prefers you talk more narrowly about one theme right for for the best practices obviously there's
podcasts and that's a different story but in this world I think that the way that Gary created daily V I think it was very novel in the beginning and I think that that got a lot of traction we were able to capture some incredible moments but as the platforms evolved that style of
content became very difficult to get any sort of traction with because you know in in an episode he might be meeting with a CEO then a rapper then he's going to an event and then he's doing you know maybe book signing or something like that and it's all over the place and so
I think that the way that YouTube has evolved is not super conducive for the style of content that he is able to produce given the amount of time that he has he's not able to like sit down and record like there was never a time where we were like let's sit down and
record a YouTube video that never happened not once because he's operating his businesses and then he's building Gary ve as a documentation of that and he stayed consistent with that you know you know do I think that it'd be awesome one day for him to sit down and do a direct CER video
yes I think it would [ __ ] smash like I think that really it's just a matter of priorities right now he's in a season where he's focusing on his business and not so much on Gary vaynerchuk or daily V so that's kind of why it is what it is that's what I
think um but I'll be honest with you I feel like I noticed around five months ago maybe like three or four months ago I started noticing the content was hitting again a little bit more like I started not like there was a couple of IM that he did image posts that went like
fired hundreds of thousands of likes and stuff so I I know that there's Seasons where he puts a little bit more emphasis on it so I'm going to offer you The Outsiders perspective which is a probably a good bridge for our next part of the conversation so I think Gary is a first
mover in many different things and being a professional person who is an entrepreneur who's successful creating content on YouTube before it was kind of invogue to do so created all the space and when there's no competition you can Dominate and he was crushing like crazy but as he was speaking to a very
specific I think mostly male oriented demographic like these young Hustlers who are going to grind all the time because you would see the audience and it's mostly young men who is like I'll swap me I go and sell and I'll flip this and I'll make some money him doing the garage sales he
I don't think he does that right now but seeing that I'm like okay well your audience eventually grows up and you grow out of it but him providing business advice was taken over by somebody else so the space is dominated and then someone else does it better or different and then draws that
audience in and that person is Alex Heros so whereas Gary was giving what I one of my criticisms of Gary despite all like uh what we've just been talking about is he was giving more or less similar advice to someone who was kind of at a certain level in their life and it
wasn't like I as a multi-millionaire business person am going to learn from unless maybe I did the 4ds with him but it was kind of very rudimentary stuff which is good for broad audience and then comes in this new guy with a crazy handlebar mustache the um what do we call this the
it's not a wife be Tech the tank top with his plaid shirt and his cut off jeans the craziest style comes in and really gives highle really good business stuff that's highly actionable for people anywhere from the 100,000 to maybe 1010 million range where they can learn a lot from so then he
starts to dominate and I think maybe the universe can only have so many players in one category and so now Alex is just crushing and destroying and it's kind of wild that you're moving from person to person coincidentally I think but like you seem to have your finger on the pulse or maybe
the pulse finds you I don't know what the deal is but what do you think about that theory that there's space and someone else is going to take it and someone one day somebody else will take it from Alex the next version the next iteration of it I will give kind of an
interesting Theory um that I have on this which is if you were to go back to really early Gary content it is far more tactical and as he evolved he got out of the tactics and more into the mindset and I think what a lot of people who create content and give advice
and and all of that online especially if they engage with a lot of different people is you do start to realize that the tactics are very important but if the individual doesn't have the correct mindset mindset they will never actually put those tactics into place right so like you can talk all you
want about like social media strategy but if you're terrified about ever showing up on video it doesn't [ __ ] matter right you got to get over that [ __ ] you know I wasn't with Gary in the very beginning by any means but I consumed his cont so the evolution I saw
there is he went from more in the dirt tactical to more in the clouds mindset I think that's typic the journey that these individuals go on is they start more tactical right like even if you look at Alex's Burly videos like the webcam days that [ __ ] is in the weeds right
like and I think that as a I know for anybody watching the 20 to build their brand that's where you should start you build your base off of that you build credibility and a strong Foundation off of people going [ __ ] this dude knows what the [ __ ] he's talking about
she knows what she's talking about right like that's what you want to build in my opinion and so I I do I totally hear what you're saying and I think you're right I would almost say it's like Gary occupied this space and then moved to a different space and Alex came in and
thunderously took over that space for sure and I think what you probably have maybe even observed in Alex's content and maybe over the next 10 years we'll see is there is a little bit more that he speaks to the mindset right because that that is kind of the variable that it comes down
to even with like CEOs right like taking action there's a lot that comes with that and a lot of it comes down to helping walk them through some sort of mental blockage that they have or whatever yeah so I I think um right now we're in that season with you know horoi with
Alex and I'm curious to see what the next five years look like on that FR I I I like your take on that that we grow we evolve and we start to understand and I agree with you and them that you can talk tactics into your blue in the face but if somebody
doesn't believe it's going to work they'll never take action so the bigger play is to understand what the mindset the limiting beliefs are help them overcome that but then what happens is you s to drift away from this core audience of young entrepreneurs who want to who want more tactics because they they
have the right mindset let's just say and so you have to choose and so Alex comes in he does this and then this is kind of interesting because it's a crossover part you you I guess they reach out to you they're in Vegas you're in Vegas and you're talking and then you wind
up being their content director and you're managing teams and you're building teams and what is that transition like for you because now you're not like the the second to dck you're the first to Alex and Lea yeah so different roles different responsibilities tell me a little bit about that what's what that's like
and I have a lot more questions for you there I kind of brushed over the the way that we got put in contact so I want to give credit where credit is due they um there's a character by the name of Ed turny uh that worked at Prestige labs and Ed was um
really into the Gary world big fan of Gary and he actually was one of my best friends Jason Marina his first client and kind of Mentor Jason did kind of the Gary ve stuff with Ed Jason ended up coming over on the team Gary and him and I became like best homies Ed
had for years been like Alex you got to make content like you got to do what der's doing like you got so much up here and the way that you are able to distill highlevel Concepts into a way that like a lay person would understand you'll dominate in content so he just kept
pushing that and stuff and uh Alex and Lela were like yeah we agree I think this makes sense we want to find our dck and Ed reached out to Jason and was like do you know anybody and Jason was like holy [ __ ] Caleb moved to V a month ago this is
insane so Jason reached out to me and he was like dude there's this couple they are very interesting and I think that this is a legitimate opportunity because and the reason why he said that is and I'm sure you can imagine as somebody on team Gary you get a ton of people that
reach out like I mean my inbox was like flooded with people being like I want to do the Gary ve thing but they never meant it they didn't realize what the actual investment was when I talked to Alex and Lea I realized oh [ __ ] they get it cuz our conversation immediately
went from being let's bring you on as our drock to like no we need to build a team we need to build something that is going to have the infrastructure to be able to scale this thing the way that we want they had a really big vision for it right off the G
and they were willing to invest the time the effort and the money that it takes to build a team like that right so yeah that was that was just Serendipity like that was just crazy and yeah it was insane when I started everything was out of house it was all vendors that they
were working with and so my first task was to meet with all the vendors and get a deep understanding of what they were already doing right and to work with them help get them more ammo get them more media right like be that bridge but then ultimately we wanted to bring everything in
house Chris the the thing that was super interesting and my fear going into it cuz you called it out I had never built a team I had maned people before but I had never built a team and I had never managed more than like two individuals at a time and I remember talking
TOA about that and being concerned and and and just being honest with them of like you know I'm down and I have taken a lot of notes over the last you know at the time like 13 14 years of managers creative directors I've worked for things that they did that I loved and
things that they did that I did not love that I would do differently so I had my theories but I was I was nervous about it and she I remember she was like you have all the right character traits you have all the hard skills I can train you on how to do
the team [ __ ] I remember wondering what is it going to be like going from being the doer to empowering and overseeing the doers and I was scared but Chris that's the most fulfilling thing I've ever done with my life I realized I enjoy helping editors grow in their craft more than
I enjoyed editing and I thought when I was an editor I was like this is Peak happiness there's nothing I could ever do that I'll enjoy more I used to I would sit for 12 hours straight and edit and it felt like it was like 2 minutes like I loved editing and I
realized I love this even more than editing it was it was a wild transition lots to kind of figure out here yeah when when I saw Alex speak and I've seen him speak at a couple different events sometimes with Leila and she did her thing and he did his thing they speak very
fondly and affectionately of and I feel like somewhere along the way maybe I'm misreading or or reading too much into this that you guys transcended just like hey he works for us he runs our team and like you're having dinner together and it's not not work rated and so you're part of the
fam so he if that's true I thought you were a lifer and then I I hear from our mutual friend like oh Caleb's not there anymore I'm like what what okay so what what's going on you're 100% right like I think think there was a much deeper connection than just like uh kind
of like an employee Dynamic I we did we did holidays together and everything like that um and we were building and they're still building something absolutely incredible that I believe in 100 [ __ ] percent to be honest with you it kind of just came to this point where I was ignoring too
many incredible opportunities um over the last two and a half years I haven't been super public and done like content and stuff I've done like three podcasts and one of those podcasts kind of blew up um or at least for me right like I'm a nobody nobody knows who Caleb is it had
like 200,000 views and the characters that were reaching out to me were insane brands that are like you know I I mentioned my obsession around Harley like brands that I love were reaching out to me and I was ignoring it all I uh I really agree with what Alex talks about about like
extreme Focus on the opportunity I handed and I really believed and still believe they're the most prolific in business it started getting to a point where was no longer making sense to ignore those um the opportunities were getting too crazy and I just felt like this was the next natural step in my
career and I would regret in 5 to 10 years if I were to look back and be like I wonder what would have happened if I would have tried this idea of going out on my own like I kind of I mean since I was like a little kid I mean like nine
eight nine I always thought I would have a business of my own then I worked for Gary And I was like there's no [ __ ] way I'm G to do that this is insane I worked for Alex and Leela I was like there's no [ __ ] way I'm going to do
this this is insane and then I realized I'm not trying to build a billion dooll company I don't need to operate the way that they have but I do have some things that I really want to accomplish in different sectors that I want to work in not just with entrepreneurs right I'm really
passionate about musicians and entertainers I think cpg is a very interesting space and I do have experience in it and so I had just kind of been testing the waters I reached out to a few people and opportunities started turning into realities and so we just kind of had a conversation where it
was like it was the next natural step and what was so great was we were building everything for this to be able to happen now I was moving up in the OR and so we were building in infrastructure to come in behind me right like I had hired creative directors that I was
training to be able to run team Alex team Lea they were running the teams right um and Michael Lyn absolute gangster like now he's the director of media there and he's overseeing the team like an absolute Savage as a side not like total Beast uh comes from the Beast World actually but yeah
we we had built that out so that it was n like I just was like Deuces run with it kind of a thing there was already the infrastructure in place for that since I've gone out on my own I've been blown away at how I can't put it in any other way things
have just fallen into place in absurd ways with brands that I've dreamed of working with and um yeah I I think like you know it's freaky I I've always wondered if I had the chops and so I'm going to spend this next year seeing and documenting if I do have the chops to
do my own thing you know how do they take it that this information that you're going to go do your own thing you said the infrastructure setup it was ready to go it wasn't you leave them in a weird bind so you have this conver conversation and everybody like I'm talking about from
the employer perspective like oh my God I love working with this person I can't see not working with them then one day they come it's like it's time for me to go boss I got my own thing how was the conversation how did it go it wasn't just one conversation it was a
sequence of conversations so I think we just over time started realizing that we were getting to the point where this was the next stab the other thing that I would say is I think there's a lot of individuals out there that are running or on teams like this that kind of have and
you know no judgment but one foot in one foot out I think the moment that that occurs you got to jump because all of a sudden your focus is no longer the same I've chosen my my whole career the 16 years I've been doing this I've always focused on the brand I'm working
for inh house at the time like there was times in New York you know it was [ __ ] expensive and I was broke as [ __ ] so I had to do side projects here and there just to pay rent but other than that like I really believed in focusing solely on
this and when I started seeing that my focus was maybe starting to go towards what could be next I think that's when we started having conversations around this is the next logical step makes sense so what what I'm hearing from you is once you realize uh maybe your your focus is drifting ever
so slightly and you got wandering eyes it was time to have like a real conversation with yourself and your your bosses at that time to say hey at some point this may happen and so everybody's getting prepared for that moment right yeah absolutely and the thing is is like the team like I
you know again I didn't make a lot of content but I did some podcasts I got credit but it's the [ __ ] team like mosy media was what built it right I empowered the team but like it wasn't me that was doing it right like I wasn't the one that was editing
all these amazing hits that was my editors that were doing that you know and so the infrastructure was in place that that we could do something like that and I think that's I think you know ultimately and I don't mean this to sound like a humble brag or something like that but I
think that's a sign of building a good team like all businesses it has to be a able to survive without the key person otherwise it's a very fragile vulnerable business to begin with you had the opportunity to work with arguably the two biggest content creators on the planet at the point of Peak
Interest I think it gives you a very rare position to to to see things that no one can see I would love for you to do this and they're all they're both like also throw breed entrepreneurs I would love to hear your top five or three or whatever strategies from content like what
you've learned if you want to establish a media Empire and then also your top five business lessons you glean from them because it's like there's Caleb the Creator and helping to build media and Empire and then there's like they're saying things that are just like this is like a master's degree in business
right Tak to business school so paid to get my and Bally like absurd yes so I would love to hear your top three to five takeaways from the content strategy side yeah pause and then switch to business side go ahead the first one is going to be around Leila um I I think
that Vlogs are a very interesting medium to create content around um and to utilize online and I think that right now we're kind of in a weird spot with Vlogs where I think that a lot of people are operating in like a 2012 2014 environment with them there's a show that she does
on YouTube called the hor mosis and it's it's a vlog we created that because unfortunately the way our world works is people assume that it's only Alex running everything and that Lila doesn't do [ __ ] because she's a woman uh the reality is quite the opposite she runs [ __ ] right
she's an UT talk her she's an absolute gangster like a Savage and so we wanted to create a series and content that document her excellence and showed her expertise in action up to that point there had only been videos where she was talking about what she did or Alex was referencing what she
had did but nobody had actually seen it in action so I think what we discovered with that cuz that changed the trajectory of her brand in my opinion massively is it allowed people to see her expertise in action and so I think for a lot of people they have an incorrect desire in
making a vlog it is not a width play it is a depth play we built extreme depth with the audience through her Vlog so I think that's a big one on the content side that that we learned was like if you are an individual who is sitting in front of a camera on
a couch talking about what you do there is going to be a natural amount of skepticism and now more than ever because there's a bunch of huers that are talking mad [ __ ] online that don't actually do anything and don't know what the [ __ ] they're talking about and they're just
just regurgitating [ __ ] that they hear from you and they're like trying to add their own spinto it or some weird [ __ ] like that we wanted to show that she was actually doing this day in and day out so I think that is a good utilization of like the Vlog
format I actually think that that's going to be a big thing over the next two years uh in in content online I think you we're going to see more of that I think another one is and this is really I would say a lesson that I got from Alex which is being able
to take really indepth information and highlevel Concepts and truly like people talk about think about your audience you know always make content for your audience I think a lot of people say it don't actually do it he really [ __ ] does it right he is so so passionate about figuring out how
to define terms in a way that will make things operational that you can actually execute on I remember when he you know started defining like anxiety and sadness in these ways that I looked at it and I was like oh [ __ ] this gives me what I can do about so I
think if you whatever industry you're in if you're making content taking the very indepth uh knowledge that you have and boiling it down to I mean he would always talk about trying to get things down to a third grade level to be able to communicate right um I think that's a big one
I I'll dive deeper on that actually when you make educational content uh like if you're a professor right and you're teaching a class or whatever you're operating under the assumption that all your students are at a similar Baseline of knowledge there's going to be outliers and stuff like that but they're all operating
off of a similar amount of knowledge when you're a content creator online it becomes very difficult to do that right because you have no idea who's going to [ __ ] watch your videos right you might have somebody who is ultra experienced in business and has been in it for 11 years and
somebody who has been into it for 11 seconds right like the moment they clicked on the video they're like oh I like business you that becomes very difficult to create true educational content off of because you're having to make massive assumptions about where the audience is Opera off I think what Alex does
an incredible job of is understanding that if he were to take these Concepts at a third grade level he's making it accessible to the Mass and he's not making assumptions about people understanding what CAC means right what LTV is so I think for anybody watching or listening it's really important to be able
to Think Through the lens not only of the advanced viewer but the lay viewer right and something that we did that we created I think is super helpful is we created two different avatars nothing like complex but we had Advanced atom and simple Sam and if you're making really in-depth content you're making
it for advanced adom but when we're making the more wide content you're thinking about simple sanm this is somebody who maybe hasn't made even 100K in their business yet right I think that taking that and applying it to your content is extremely useful so that's a big one there I think another one
is oh this is a huge one Chris utilizing customer wins as your source of content if you take a look at Alex and YouTube channel 95% of the content is just case studies it's just made in an entertaining way platform native they're not the boring case study that exists on that one tab
on your website that nobody [ __ ] watches they're engaging but they're all they are is just case studies so over and over and over they are just hammering with the audience success after success after success that they've had right or that their customers partners had and I think that if you do
that over time I I truly believe that brand is just deliberate pairing of two different things multiple things together through repetition and eventually the audience starts to create the association so if you over repetition show success with your advice or your tactics over time your audience Associates you with that success that business
success those outcomes and so I think some of what they're doing is training Their audience to trust them they're giving the tactic that worked for a previous uh partner or a business that they had then they're sharing how you can put it into place then you put it into place you find success
with it and then you associate that success with them AKA scaling trust and so I think that is something that they have done in an excellent way that a lot of people do struggle with I think Leila the most incredible interpretation of Gary's document don't create I can't remember if you guys talked
about this or not but when she said I was like I can't believe I didn't think of this like this killed me she was like it doesn't necessarily mean that you have a videographer follow you around all the time it means that you talk about things that have occurred so you can look
at your calendar for the last week or month and talk about those items right success stories of like a tough conversation she had with an executive and then she can share that and five other stories that she has so I think sharing wins and success stories is something that a lot more businesses
should be doing but just not in a boring you know customer testimonial [ __ ] way uh that would be a third one I think for a fourth one um it would probably be and this is something that I've always believed but we started to see success with it and so it verified
kind of a belief um is the best version of content in 2025 is making it for each platform specifically now in the beginning we didn't have the infrastructure in place to do that know when it's just me and I'm editing everything I can't make unique content for Instagram Tik Tok you know YouTube
LinkedIn Etc but final form I think that is the best version of 2025 content right it's you have somebody who is maybe clipping from a podcast maybe you're still using that that you know OG Gary V method where you have your pillar content you're clipping from it but you should have somebody that's
clipping with Tik Tok in mind with YouTube shorts in mind with Instagram in mind two years ago you know this Chris like if you had success with a clip on Tik Tok you knew it was going to slap on Instagram and YouTube shorts now they're completely fragmented they behave completely differently and so
um I think I would say that was more of a learning of us as a team operating in action and realizing like okay we now have the bandwidth and the bodies to be able to do this let's start to assign different platforms to different individuals and have them own it now you know
we didn't have a team of like 50 people so the way that we would operate on that is you define your top four platforms that you prioritize and you give those out and then the remaining for you give them as a secondary platform right 80% of their energy goes towards creating for the
top priority and then 20% goes to the secondary you know priority I think that's a big one I think the other one is and this this is so basic and used a lot but I'll just hammer it home again be the same [ __ ] person you are online offline who you are
in your content is who you should be when people meet you in person the discrepancy between the two is what creates a lot of brand problems and trust issues and I think that right now we're in a season of of a culture where everyone's showing up in a completely different way online than
they actually are behaving in real life and that creates a real issue when your audience fans whatever you want to call them meet you right like I remember when we were at that dinner and I met you I was like Chris is exactly who he is online like he's just a cool thoughtful
kind human right very intelligent very very knowledgeable there's no difference from what I had seen and that for me was confirming of your brand right I trusted you more in that moment so I think those would be a couple of different takeaways okay that's wonderful let me quickly recap for everybody when it
comes to long form content you're you're you're making this call that what you want to do is go deep show the people versus talk about what it is that you do that's how you build credibility plus it's way more entertaining to watch because everyone can talk about something and I think you call
them husters there's a lot of them out there there's tons there's more of them out there than there are the real ones who are actually doing it you talked about going uh uh how how Alex and I wish I had an opportunity to interview him but he has a gift not everybody has
this and some people throw this kind of gift on me but I'm like I've seen a master at work when he's able to take super complicated Concepts that you don't care about and make him so digestible if you not seen his book before and he says in his book I write this for
like a gym rat who doesn't want to read books and it's using large Point type phrases things simply kind of Sharpie marker cartoon kind of drawings so that you can read it and and it's there's a genius in that approach you talk about sharing customer success stories it's just a large driver of
proof that you can do it and it kind of builds upon itself and connecting and associating the success with the person who brings it to you then therefore that person is successful and you just keep doing this over and over again you talk about doing native content for specific platforms yes you know
versus the cop uh produce ones and push out to all platforms we know that it doesn't work I'm not even sure it worked in the beginning because they all behave a little bit differently and if you if that's the only thing you can do then do that but it's like if you want
to grow on specific platforms and they're important to you you have to spend the time and energy to do it in the way that the the platform and the people who show up understand it last one is be the same person be you whether you like you or not just be you because
eventually the the world will find out and it's it's really weird it's super fractured of a brand experience and here's the sad part as I'm in more Creator circles like oh my God that person is nothing like how they appear they talk one game they play a different game they have one personality
they have a different personality and it's really jarring hence that phrase be careful of meeting your Heroes because they're bound to let you down yeah like I'm trying the best to be me and sometimes me on camera is not somebody you like and I don't want you to come up to me in
real life it's like no you're a prick well I was a prick on camera too so there you go I'm just going to be consistent all the way through and like you said when people connect the dots they they're going to make a decision about you and they're going to tell other people
here's the thing you think oh only one person you know I always tell my wife it's like I got to be the best me the meest me I can be because sometimes I go out and it's like I look like a scrub and somebody's like oh yeah yeah didn't shower and shave today
did you you're right I didn't and I'm going to hide for a little bit you know even people want things like people want you to show up the way that you've been showing up those are excellent I'm sure people can say you know we want the rest of that and that's another conversation
for another day but I do want Before Time runs out to talk about the business insights now you're in business for yourself yes I'm curious if you could do the same thing share with us what you think the big business ideas are the top five I think the biggest lesson I learned from
Alex fosi was the level of effort that you need to put into making something great um he's talked about it but I think you know he maybe even underplays it a little bit um of humility but he wrote leagues 19 times 19 times he spent eight hours minimum a day almost the whole
time I've known it working on that book like Relentless focus and effort on making one single product incredible and I think that's why offers did what it did without him promoting it or having any sort of campaigns or anything right like it's just an incredible product and so I witnessed firsthand a different
level of effort that goes into creating a high quality product and it really set the bar for me on how I view projects that I'm going to work on for myself right and and how I show up for partners of mine I want to bring that level of Excellence you know so I
think that's a big one another one that I think is really important and I think this will resonate with your audience hardcore is never discount I think I in my early days when I was freelancing I would do anything to get a gig I now you know I since I've made my announcement
I've had a lot of different Discovery calls um I've been blessed to have a lot of different Discovery calls that is an amazing thing um and on some of them you know we discover that my rates are too high for the individual at the current place that they're at in business and old
Caleb would be like all right cool I got to figure out a way to get up now I'm like what an amazing brand position to be in that they can strive to eventually work with me and that's what a lot of them are saying is like okay cool I now know what my
goal is I need to be able to afford this rate monthly I want to work with you next year that is the goal what an incredible brand position so I think you know that's that kind of an offsho from it but I also think that um it massively devalues the product that you
have you talk about this so much right like that's a big one for me so I I want to always like if I going to Discount I'm just going to do it for [ __ ] free like I'll just do it as a favor right like if if I'm going to do that
cool otherwise it's full price um and I think that's a really important one especially and I know we as creatives all think that we're so unique but I think we are I think we tend to struggle with that hardcore right for various reasons uh a lot of different reasons but and you've touched
on all of them but I really think that that's a big one for creatives and so like if I could tell my younger self that I wish I would have known that earlier but now I really do so I think that's a big one I think another one uh is the experience you
provide for customers um something that's really cool that I learned from Lea is I'm gonna give you four so this is number three I have one more from her after this but the level of attention that she put towards the experience for people who came came through for workshops that we were running
I'm talking unbelievable like training the team to like memorize names and greet people by their name right like following kind of like the way that RIT Carlton operates like when when somebody says you know thank you for doing this my pleasure right like if you see somebody walking around maybe looking confused hey
do you need help finding something hey can I go grab you a water do you need a snack do you need a coffee right like uh literally there'd be times where people maybe would uh have worn heels or something like that and they were super uncomfortable we would literally order them shoes and
have the shoes show up within an hour so that they could be comfortable for the rest of the event and that all came from Lea like she really prioritized that so I think customer experience you know and it kind of ties into the first point of like the level of effort for a
great product I think it's just like that's the back end this is the front end side of things they put a lot of attention towards that and so observing that and being a part of it was powerful for me I think the fourth one and the one that I'm probably most passionate about
is it's all about the team it's all about who you bring on how you bring them on and then how you invest in them and train them and your honestly retention strategy for top talent to retain them so one one I had never ever been a part of such a robust hiring process
like I mean it's incredible right like we would do a screening call then it goes to a technical interview right then a culturefit interview then a final interview right and in there somewhere typically there was a technical assessment that occurred super in-depth process in order to weed out incorrect candidates and find the
right one right cuz we both know it's highly expensive to hire somebody that is not the right fit that then you have to move out within a couple of months right um I think so seeing on the hiring side like the way that we operated on that changed my view and my bar
for how I measure a hiring process in an or moving forward also onboarding I remember I knew what was expected of me before I even started right like a novel concept that I had literally never experienced at any org I've ever been at was a 306090 she said me a 30s 30-day 60-day
90-day plan of what I was going to be prioritizing so like unlike previous roles where it's like the first week you're twing your thumbs being like what the [ __ ] am I supposed to do here anxiety goes through the roof I knew day one exactly what my priorities are and what I
would execute on and so then I was able to do that for everybody that came into the team um I think that was incredible the training right investing in the team always pouring into improving their skill sets right like if you improve the people on your team and invest in them they're going
to grow your business I I believed even with the media team in a similar way I was getting to the point where the team was so mature and Powerful I was like I don't want to top down strategy I want to invest in them and have a bottom up strategy like they can
inform what we do on Instagram not me right and so I think just the level of investment and Trust being placed in the team huge lesson for me a lot of people skimp on hiring they don't pay well and so they don't they're not able to get a players [ __ ] worth
it it's [ __ ] worth it I would trade one a editor for 10 B minuses and C's all day like you will get so much more value out of it and so I think a real focus and emphasis on your team who you surround yourself with um and then ensuring that you
build out a to retain them now more than ever creatives and people that understand social have more opportunities than ever right they can go off and work for anybody they can go do their own thing how are you going to retain Talent right and so I I always wanted to think about how
do I ensure that this is an opportunity for the team that they always see themselves continually growing getting new opportunities learning being challenged and being trusted right like I gave Instagram I gave YouTube over to people that they would run cuz I trusted them and I think that if if you build that
infrastructure you can have a team that grows your brand grows your business for you alongside you rather than you being you know the dri of the ship you're right you could probably do a whole episode on just team building management hiring firing on boarding that was a very high level and impactful uh
kind of Insight that you shared with us so let me quickly recap for everybody uh to make something great requires a lot of effort it's a lot harder than you think and a lot of us can get to pretty good but to get it past the greatness it requires a level focus and
dedication that's a thematic thing that you're seeing both herois uh number two is you're like free or full price don't discount yourself don't discount your value set your bar and one day the clients will aspire to work with you and they want to work with you I have always said this they will
find the money somehow it's never about the price it's because they didn't want to work with you yes you talked about the designing a beautiful customer experience from beginning to end looking out for and planning for all the little things to make sure that end to end the experience is Sublime and there
and I think everybody understands the Ritz Carlton fication of your business and how they're all trained to like to put the customer experience ahead of everything else and to look out for the wellness and the well-being of their customers you talked about team uh and and one to hire for the very best
investing in them because they will make your company much much better there's too much to unpack in that moment but I just like how you said this has been such a thorough process that not everybody gets to enter in the kingdom and if you're good enough to enter in the Kingdom you'll be
compensated well you'll be treated well and you can be assured that they'll always invest in you because like if you like I thought you were going to say this like if your team improves by 20% multiply it across every person that works for you that's those are gigantic numbers and it's not always
linear sometimes it's exponential because there's some compounded effect that's happening across multiple teams right that was awesome absolutely and I mean to be honest with you I you nailed it I there's so much that I I think about and I think that you know this year I'm going to be putting out content
for myself for the first time ever and what I'm going to talk a lot about is training creatives right like how I think I have some very unique perspectives on uh training giving feedback to editors to designers that is not what a lot of my counterparts do but I think FASTT trcks a
lot of creatives to go from maybe a seven to a nine I'll put it this way I've been managed by some incredible people but there's a lot of [ __ ] up [ __ ] that creative directors and managers do in leading a creative team that stifles creativity and limits the amount of
growth that not only the individual can have but the team collectively can have together and it's really my hope to be able to share that with a lot of people and hopefully shift kind of how creative teams are run because I think there's a much better way to do it well I'm looking
forward to hearing that uh I've managed a creative company for 20 some OD years doing Production Services and it's different when you're dealing with left brainers uh they understand rules on how to move forward it's a lot easier to deal with them when you're dealing with individual creative spirits and beings a lot
harder to manage you want to challenge them you want to be clear but you also don't want to be Draconian how you manage them because then they stop functioning as creative people and they start turning in work instead Caleb I want to ask you this really quickly before we run out of time
what is next for you before I wish you well on on your future endeav thanks Chris um well I am building out a consulting firm called Rolston and we are partnering with a select few Brands to help them scale their brand online half of our partners fall into the camp of we have
a team and infrastructure in place we've gotten to 50 60% and we just we've hit a ceiling that we can't crack and we need somebody to come in and help lead the direction on how to get through that I've cracked that ceiling multiple times so that's the uh one half the other half
is there are individuals who recognize that their personal brand is the biggest advantage they have in 2025 moving forward but they don't know where to start and they want to do it correct from the beginning and so they're bringing me on to help build out their team recruit Place everything train them um
and so that's what I'm doing and building this here and you know I I think 2025 will kind of be I the internal model I have is it's my Proving Grounds do I have what it takes to do this um for others at this scale I'm [ __ ] amped so no thing
I'm going to try and Doc minute too and share it hopefully with a slightly unique perspective I have a real passion for I hope this comes across correctly like younger versions of myself and wanting to help guide them and maybe FastTrack and avoid some of the the waste of time that I had
you know coming up and stuff it's awesome I can't wait to consume that content and to share it with others so how do people track you down what are the contact info yeah uh my website is my name Kaleb bron.com I'm on Instagram Kaleb Bron LinkedIn Caleb Ron uh I'm GNA start making
YouTube content which is going to be wild so my YouTube channel Caleb Ron if you go there right now it's like old interviews I did with like hardcore bands because I'm really into that world that's what thr there right now but eventually there'll be some some [ __ ] around this stuff so
yeah I mean anywhere if you want to DM me whatever I would love to chat I also real quick want to say thank you Chris for everything that you've done man like the amount of creatives that I know that mentioned this the direct impact that you've had and how you've paved the way
unbelievable man like truly you've done something really impactful for a community that has always been thrown in the cage in the corner right like creatives don't feed the wild animals and you brought such an amazing light to us so thanks man like you are you're the goat man so thank you and thanks
for having me on Caleb thanks so much for saying that that means a lot and and we we all do what we do and we never know who it hits and so it's always wonderful when we find someone in the wild and like hey you did that thing and it helped me and
to me it's like the spice of life you know I'm a big Dune fan it's like the spice milange this is my spice it's what keeps me going it's what allows me to to jump and travel space and time and so it's it's always lovely to hear that so best of luck to
you you've done so much for others now I'm rooting for you to do so much for yourself and it's about darn time and uh we'll link all the websites and the socials in the in the show notes so make sure you guys all check that out it's been a real pleasure talking to
Caleb thanks for sharing so openly and honestly and like I'm saying I'm going to be looking forward to hearing what you've learned seeing it from the inside for operations way way bigger than where we're at how they hire how they do things and and the impact that you're going to make awesome job
I appreciate you brother okay man take care
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