251 - He Failed for 20 Years, Then Built a $1B Brand in 6 with Ryan Bartlett

11 Nov 2025 · 1 h · 27 chapters

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In short

Ryan Bartlett’s path to building True Classic, a billion-dollar men’s t-shirt brand, after decades of “failed” careers (music and poker), emphasizing compounding skills, solving a clear product problem (fit/comfort/price), and using low-risk iteration.

Guest backgrounds

Ryan Bartlett (age 43) is founder/CEO of True Classic, known for Instagram ads. Before True Classic, he flunked/kicked out of college, studied music at Full Sail (Orlando), worked about a decade in studios as a session musician (about $35K/year), then tried professional poker in Vegas (burned ~$3K quickly), and later built a digital marketing/SEO + paid media agency (low seven figures/month).

Key claims

Failure isn’t final; life is long and setbacks compound. Creativity from music translates to scalable ad/website optimization. Entrepreneurship should target “white space” and a “fat pitch” opportunity with enough confidence to keep going. He also stresses hiring leverage (co-founders/CEO) as the company scales.

Notable examples

Homeless-shirt giveaway post for impact; True Classic’s “fit” focus (sleeves/bottom length), plus comfort and premium-at-reasonable-price positioning; scaling via Facebook ads and iterative testing.

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

Chapters

Tap a time to open that second in VO

The Turning Point of Entrepreneurship

0:00 to 0:38

Learn about the pivotal moment when Ryan decided to pursue entrepreneurship.

“What was the moment where you were like, I'm done?”

The Rise of True Classic

0:45 to 1:20

Explore the story of how True Classic became a billion-dollar brand.

“you have probably seen his ads on Instagram.”

The Journey Through Failure

1:20 to 2:26

Ryan shares his experiences of failure before achieving success in business.

“and a failed poker player for probably 20 years before he launched True Classic.”

Education and Music Career

2:26 to 4:20

Discussing Ryan’s educational background and initial career in music.

“Like that just did not feel impactful for me.”

Transitioning from Music to Marketing

4:20 to 6:40

Ryan explains his shift from the music industry to digital marketing.

“It was like my friends, my peers, other people that were like, you've got something.”

The Poker Experience

6:40 to 8:40

Ryan reflects on his time in poker and its impact on his life decisions.

“Once I got into LA, I finally did get a job with like a big music producer.”

Creativity in Business

8:40 to 13:00

How creativity from music influenced Ryan's approach to business.

“This is, I don't want to be that guy anymore.”

Finding Your Passion

13:00 to 14:01

Ryan discusses the importance of aligning passion with business opportunities.

“Like I've just always been in this I got to create, create, create mode since I was very young.”

Finding Passion and Purpose in Entrepreneurship

14:01 to 16:44

Learn how to align your interests with market opportunities for entrepreneurial success.

“if you're gonna get into entrepreneurship, pick something that you like and are interested in, something you're good at and something the world will pay you for, right?”

The Journey to True Classic

16:44 to 19:38

Explore the pivotal moments that led to the creation of True Classic.

“I thought that was the thing that was going to really make me happy.”
Show all 27 chapters

Call to Action for Listeners

19:38 to 20:14

Hear a personal request for support from the host to the audience.

“Hey, I don't know if you remember this, but when we started this podcast, we entered into a social contract.”

The Birth of True Classic's Idea

20:14 to 21:35

Discover the inspiration behind the True Classic brand and its early concept.

“Ironically, looking back, and I made a post about this a while back, the idea started when I was like in my, like 19-ish, but I had forgotten about it as, but I had told my brother about it.”

Identifying Problems in the Apparel Market

21:35 to 24:22

Learn how recognizing market gaps can lead to successful business opportunities.

“But were you actually looking at it that way or was it still, hey, this is kind of just where my curiosity is leading me and it just so happened it worked out.”

The Philosophy of Seizing Opportunities

24:22 to 27:58

Understand the importance of recognizing and acting on business opportunities.

“It definitely takes a certain amount of real confidence to execute on that vision.”

The Long Game of Entrepreneurship

28:00 to 29:48

Learn why passion and dedication are crucial for long-term success in business.

“So for anybody listening that is in that, like, I could do anything mode.”

Reflecting on Past Endeavors

29:48 to 31:46

Explore the value of past experiences and the importance of finding leverage points.

“I mean, you know, we take bets here on product inventory to the tune of tens of millions of dollars on a whim in a, in a boardroom in a 30 minute meeting.”

Building a Strong Team

31:46 to 34:26

Understand the significance of finding the right co-founders and building a strong team.

“So as much as I would have loved to be killing it, I just wouldn't have been killing it, which is hard to say sometimes.”

The Complexity of People Management

34:26 to 37:18

Discover the challenges of managing people and the importance of communication in business.

“Even to this day, we have a million fires, But it wasn't until I brought Ben on, who's our current CEO, that he created unbelievable leverage for me.”

Evolving Focus as a Business Grows

37:18 to 39:38

Learn about the necessity of shifting focus from operations to people as a business scales.

“There's just nothing, Ben and I always say that, there's just like nothing we can't figure out.”

Finding Your Native Genius

39:38 to 40:53

Explore the importance of focusing on what you do best in business.

“I ran a Facebook ad today and I got a, you know, three X row as right.”

Advice for Future Generations

40:53 to 42:04

Gain insights on how to navigate career paths and find fulfillment later in life.

“that you feel like is your native genius?”

Embracing Failure on the Path to Success

42:04 to 45:56

Learn how embracing failure can lead to breakthroughs in business.

“When I talk to people, sometimes they're like, I would have told myself to not be so hard on myself, you know, go easier.”

The Importance of Creativity in Business

45:56 to 48:26

Discover how creativity serves as a crucial advantage in the business landscape.

“If you have a way to develop creativity, I do think it's the ultimate hack in business.”

Leveraging New Technology for Content Creation

48:26 to 53:04

Explore how to effectively use new tools for creative content generation.

“either have or you don't, but you can develop the muscle.”

The Future of AI in Marketing and Advertising

53:04 to 56:00

Understand the evolving role of AI in marketing and how it can enhance creativity.

“They just rolled that out three days ago where you can storyboard the scene and then it'll break it down in increments of seconds.”

The Future of AI in Advertising

56:00 to 59:00

Explore how AI tools can enhance content creation and advertising strategies.

“How do you view this impacting the ability to run and generate ads?”

Building a Brand: True Classic

59:00 to 59:20

Learn about Ryan Bartlett's journey and strategies for building a billion-dollar brand.

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Transcript

Automatic transcript. May contain errors.

0:00What was the moment where you were like, I'm done? I was tired of being broke. I was tired of not having a family and being married. Like I wanted that life. It's such a long journey. And I just think that people need to be aware that everything they're going through is just a building block to something greater. Nothing you're dealing with today is forever. A lot of young entrepreneurs are so worried about failure and having failed so many times. It just did not feel risky. If it doesn't work, I just close shop and move on. If it wasn't true classic, it would have been a lab diamond. If it wasn't a lab diamond, it would have been matcha.

0:29I would have just kept going until I nailed something. It just so happens that True Classic worked.

0:38Ryan Bartlett, I am really excited to talk to you today. So for those who don't know, Ryan Bartlett is the founder and CEO of True Classic. If you are a male between the ages of 20 and 50, you have probably seen his ads on Instagram. For these shirts, I'm actually wearing a True Classic shirt right now. Well, thank you for putting that on right before this show. Bro, they're the best fitting shirts. I appreciate it. In the course of like six years, Ryan built a brand that has sold over 30 million t-shirts. It's a billion dollar brand, more than a billion dollar brand. They've sold millions of dollars worth of merchandise.

1:09They've become a household name. He basically spoke a new product into existence. But that can feel kind of unattainable for a new entrepreneur or for just anybody who's just like trying to get started. And I think what I would love to talk to you about in particular is what people don't talk about much is he was also a failed musician. and a failed poker player for probably 20 years before he launched True Classic. It's not like he was a 21-year-old sitting in his Harvard dorm room and decided, I'm going to go ahead and start an app where we rate people's faces. And it turns into the next Facebook.

1:39You saw some stuff. And I think that conversation about compounding experience, compounding interests leads you to where you are today. And it's never too late to jump into entrepreneurship. So here's my first question. What did I miss with that introduction? What did I get right? You got it all right. It's a crazy story and life is long is what I'll say. I think I thought that after failing in music, failing in poker, getting into marketing agency and having a little bit of success that that was probably going to be it for me. And I didn't need to create all this chaos of a life that I have now.

2:17I was making good money. I was totally fine and comfortable. I think I was just – I was missing something. I was missing impact. I was missing like, what am I actually doing for humans out here aside from just making their dentist office grow a little bit more through my agency? Like that just did not feel impactful for me. So like we made a post today. You'll see there was a post where an influencer gave a bunch of shirts out to the homeless at scale. And for me, like that's why I did this stuff. ultimately. It was like for those moments where you can make an impact on someone's life or like even now you and me are talking and the audience is going to hear this and it sparks something in somebody to try something.

3:02And maybe they had failed most of their life as well. And then finally get the itch to try something because, you know, we, we made it sound like it was possible for them. So that's what this is all about. How old are you? I'm 43, 43 years old today. easy to look at you and be like, oh my gosh, billion dollar brand selling millions of teas a year. Just, I can't even fathom that. Take me back 20 years. Like what was 23 year old Ryan doing? Oh my gosh. I was a little bit of a wreck. I mean, I, I failed out of college because I was just a party animal. I just, I loved partying. I love being out. I love being social.

3:43I was not focused on school in my early 20s. I was focused on music and making it as a music producer. That was kind of like, that's just what I wanted to do. That was what I was best at at the time. And then you dropped out to just do music? Flunked out. Didn't drop out. Got kicked out more specifically. I went back into community college because my parents were like, well, just take a semester off and go to community and then go back to Michigan State. And ironically, they were telling me my whole life, I should do business. And, you know, parents are always right in the end. It was everyone else around me that was telling me to do music.

4:22It was like my friends, my peers, other people that were like, you've got something. You got to go out there and make something. And my parents were like, yeah, music industry is not a great business. Like, I think you are talented, they would say to me. But like, I just think you're more built for business. So I think you should go into Michigan State and get a business degree. And so that's what I was on my path to do. I just, I started taking these like hard math classes and science classes. I got so uninterested. I'm like, this has nothing to do with business guys. So just to foreshadow, did you ever go back to school or did you, did you?

4:56I did. Yeah. Eventually. So I flunked out and then my parents were like, well, now you're on your own. Now you got to figure it out. You wasted our money. You wasted our time. And now you got to go make something of yourself. And I was like, well, I'm passionate about music. I have talent in music. Why don't I go get an audio engineering degree? And why don't I figure that? Let me start there. And so that was great. And I did end up graduating. I got an associate's, a bachelor's and a master's in music. So where'd you go to school? Was that Michigan State you went back to? No, it was a school, a trade school in Orlando, Florida called Full Sail.

5:30And it was very much about the arts. It was a music, film, and everything in between post-production where you were basically just in a recording studio all day, learning how to run a board, learning how to edit audio, learning how to produce music, learning how to really run top to bottom Pro Tools and all those other systems. So it was fun. So many people who are about to hear this don't know this about me. I went to a performing arts high school. So from grade seven through 12, I went to a performing arts high school and much to my dad's chagrin, you know, he'd be like, Nicolai, are you not going to try out for the sports teams?

6:05I'm like, well, jazz dance is the sports dad. He's like, why would you go to such school? But it wasn't college, obviously, but very similar type of classes, right? Recording, music, dance, theater, et cetera. Did not prepare me for the real world, that's for sure. But you probably actually got prepared for the real world. How long did you stay in the music industry? Because like, okay, you cool, you got those skills. You decide you're going to go be in the music industry. Was it a quick burn or was it like, no, man, I'm going to do this thing for the next 10 years? It was about a decade. Unfortunately, looking back, I burned about a decade working at recording studios, working as a session musician, working with artists.

6:46Once I got into LA, I finally did get a job with like a big music producer. But like he just he was not a great guy. He didn't treat anyone really well on his team. And we all kind of suffered for it. And it turned me off the music industry. And, you know, luckily, I needed to be turned off to like finally look at like, what are my other options? you know, because I just don't think the business of music is going to be it for me, even though I love making it. It doesn't mean I need to actually make money from it. And that took me a long time to like come to, you know, terms with, but how much money were you making?

7:22Oh God, dude, this is like, this was a while ago. So like 35 K a year. What year was that? This was 2009. I was like a taxi driver. I literally would just like pick them up and drive around all day, go to recording studios, sit in there, hate my life, go get food for people. And it was not a fun job and not glamorous at all. What was the moment where you were like, I'm done? How old were you? Do you remember? Was it a moment or was it a like progression? No, it was like 2010 ish. I had, I had just burned through so many years of doing it. I was finally just in a place where I was growing up and I'm like, I have got to get my shit together like i cannot be this living with three guys in a house musician guy anymore you know partying in the week like i was just tired of it dude i was tired of being broke i was tired of not having a family and being married like i wanted that life where did you live culver city culver city you heard a musician musicians institute yeah right there in north hollywood when i moved down to la this is like 18 years ago 2007 i worked with this kid who had special needs but he went to musicians institute he was like rain man i would like i would literally just play a chord for him or i would turn on a song and i'd be like what chord is that he's like f minor seventh suspended night and i'm like what the freak dude that's insane he had perfect pitch perfect pitch and he could hear one song one time and sit down and just he's just start playing it at the piano dude my stepmom is that way she's a professional harpist she was in the pittsburgh symphony and like unbelievable musician and she could literally you would you would play a note and she could play it on the piano like she had she has perfect pitch as well and could just sit down and play it out like even though she's not really a piano player she would just hear it and just instantly go down and just start being able to play the whole song from just top of her head it was insane i do want to come back to this to the musician point in your life because i think that there's going to be a nice thread that we can pull on but you're 30 and you're like i'm done dude.

9:21This is, I don't want to be that guy anymore. It's funny to hear you say that. Cause you're like, I wanted a wife. I wanted a family. I wanted to be about that life. But then you got into poker. No. So I went music, poker, and then back to music. So poker was like sandwiched in between music. So that was like the, so my early twenties kind of like, you know, after I graduated from Florida, I went to Atlanta, tried to do it in the music scene out there and then got into poker through that. So I was kind of juggling both in a way, but I started making money playing poker. So I was like, Oh, I'm just going to follow the money.

9:54And then I moved to Vegas to try to play professionally. Tell me how you crashed and burned. I want to hear this story. Didn't take long, buddy. I went to Vegas with like three grand and I was like, Oh, this is going to last me three years at least. And I burned through that in like a few months and I didn't want to borrow money from anybody. So I was just like, let me go. The girl I was dating at the time, I was, she's like, you need to work in the nightclub industry. You would be good for that. And so I went broke and then, you know, still did music on the side, but gave up poker forever and, uh, got in the nightclub industry for a while.

10:28How did you decide what you were going to do next? Like as you did that inventory, like what was the thing that you decided to do after that? You know, it was really, I just kept moving out of necessity. I was like, how do I make a dollar? Basically, let me go in the nightclub thing. Let me try that for a little bit. Ironically, I had been developing digital marketing skills just out of pure curiosity over the years. And I didn't really realize at the time that I had accumulated a good amount of talent in that area. And so as I was kind of poking my head up above water with the poker and the music, I started thinking about starting like a marketing agency and working with businesses.

11:05And that is when my life really started turning around very quickly. And it was as if like, I just needed to turn that switch on. And then everything just got so much better. It was like, all my skills came together and just started working in unison, the sales, the creativity, the, um, the risk tolerance, the hard work ethic, like it all just kind of worked together very, very organically. How do you think that the music helped you with those skills? How do you think that the poker helped you with like, why did creativity help with, you know, does that make Yeah, it wasn't so obvious right away in the service industry.

11:41It wasn't really apparent until I got into e-com. And that's when I realized, oh, creativity is scalable in this form of business versus like the service base. You can really only do so much. And they just the creativity hits a ceiling pretty quick. But like creating a winning ad that crushes and is really creative and thoughtful can in theory scale to the moon and drive a huge business. So it wasn't until I really started wielding my creativity in True Classic that I started seeing it really work for me. And then I was like, oh, wow, all that work I did is actually becoming useful now in this business.

12:18And it really paid massive dividends. That's a really interesting application because basically when you look at many businesses now, there's product and distribution. And distribution is really king. In doing music, all you're trying to do is figure out, at least when you're commercializing it, All you're trying to do is figure out how do I capture someone's attention? How do I get them to like this song? So you're like just constantly iterating, constantly trying to figure out was the hook right? Does that note hit just right? Should there be anything in the background? And so things that seem insignificant or nuanced to somebody else make or break a song to somebody like you.

12:54Do you think like that part of the analysis is really what has carried over? It's partly that. It's also just partly when you work that muscle as long as I have, I just don't really know any other way to think. Like I've just always been in this I got to create, create, create mode since I was very young. So coming into True Classic, it was very easy for me to go back into what I had always been doing just in a different application, right? Like I wasn't writing a song. I was writing an ad. I wasn't writing a song, but I was writing a script. or I was doing conversion rate optimization on the website and using my imagination to picture this cart to be a little bit different and more usable in the user experience.

13:36And when you couple all of that together, it's just a different application where you're wielding that creativity. But it's still, even emails, like email design, you can be super creative. Dealing with customers, you can be super creative. The product offering, you can be super creative. There isn't a part of the business that creativity doesn't touch, to be honest with you. I talk to people about this sometimes because in entrepreneurship, I think, if you're gonna get into entrepreneurship, pick something that you like and are interested in, something you're good at and something the world will pay you for, right?

14:07And so like, what are you passionate about? And sometimes we poo-poo that. We're like, well, what are you passionate about? I'm passionate about whatever, X, Y, and Z. But my opinion is like, I love music. Was I passionate about music? If I really drilled down to it, I'm probably passionate about collaborating with other people, being creative, of figuring out a way to communicate something that resonates with another individual in a way that nobody's ever done before. Those are the attributes that I'm really interested in. So it's not so much, oh, I got to figure out how to make money with music.

14:35No, it's I got to figure out how to make money with the attributes that I really enjoyed within music and apply them in a space that nobody else is doing this stuff in. But that is a very hard conclusion to come to for most people. So what you just said is a lifelong journey, I've realized. It's so easy to say that now where we are sitting, but like when you look back at when you're young, you're just trying to do what you like. And everyone tells you to follow your dreams and follow what you're good at. And you try to do that. Right. But like what you don't realize in the moment is that you're just setting yourself up for what is actually next and what you're actually supposed to be doing.

15:13So everything in your twenties, largely for most people is a complete waste. Like almost nobody I know that was doing stuff in their twenties is now doing that as an adult. Like they just, They went through a phase. They did a thing. It's like the guys I know who got law degrees got in the field and then got out of it almost immediately because they realized they didn't really want that. Right. Like every but then later in life, they were a general counsel somewhere or they use that lawyer skills to help negotiate contracts for somewhere else. And then that led him to the next thing. So it's such a long journey.

15:42And I just think that people need to be aware that everything they're going through is just a building block to something greater. and that nothing you're kind of dealing with today is forever. Like you just got to know that you're building something and you may not, it may not be super obvious right now, but just keep building whatever it is that feels right to you and just keep developing. And eventually it'll all make sense in the big scheme of things. I think it might be similar in the sense that you were kind of just head down, building, building, building. One thing led to another, led to another.

16:14You watch the agency. Was there a moment though where you finally had some breathing room? Maybe you were making enough money to pick your head up and say, huh, these are the things I like. This is what I'm good at. What do I wanna do next? How can I apply these skills? That's after you get all the things. So I got the house, I got the family, I got the kids, I got the cars. I got the whole thing after about, you know, six or seven years of true classic, low seven figures a year business. I mean, I finally got all the things I wanted. And then to your point, you start looking around going, well, what now?

16:47I thought that was the thing that was going to really make me happy. And listen, my kids and my family ultimately do make me the happiest, but I still was missing that impact component. And that's when I started thinking about e-commerce and True Classic just happened to be kind of the vehicle to get me there. Your agency, what was it exactly? Just digital marketing? It was digital marketing, but it was really SEO first and paid media and AdWords. So were you doing any of the creative or were you just doing? Yeah. We were doing a lot of web development, creative. We were doing everything because all the clients needed everything.

17:22So like a dentist in LA would need creative or they would need content or they would need their website tweaked or whatever. Like we were kind of a catch-all agency. You started True Classic in 2019. What was the agency doing in 2018? Like how much money was it generating? What were you taking home? Like low seven figures a year. Like probably, you know, like 100 grand a month. like in retainers so like you were crushing it by most standards right it was like life was good you had the family of the house you had the cars you were making good money what was the moment where you felt like i think i should do something else like i need to take another big swing honestly it was just like this feeling of it's just like i'm not doing enough for the world i don't know what that is and i don't know why it was very much just like i never felt satisfied i I never felt like what I was doing was enough.

18:15You know, it just, I had this emptiness of like, yeah, I'm making money and yeah, my kids are growing up and yeah, I'm building these other people's businesses to be a little bit bigger. But like something was just insatiable within me. Like it was just, I could not deny it. It was just something I had to like get out of my system. I was just like, I gotta do this e-com thing. I gotta see where it goes. I gotta build something. And then let's see what happens and how I feel on the other end of that. Looking back, like, do you know what was driving that? Was it, you know, you just felt like relative to your capacity, you were underperforming or is it still kind of a mystery to you?

18:47What, like what was pushing you? I think that I just knew that building other people's businesses was actually not what I was trying to accomplish in life. I think what I was actually trying to accomplish was to build a big enough business to where I could employ people and feel good about growing a huge team and then doing all this philanthropy work that, you know, I grew up having been around, you know, my parents said a lot of that growing up. And I think deep down, I felt like I owed it to them and I owed it to my family to show them kind of like how I was raised. And I need to be doing good for a lot of the homeless, a lot of the veterans.

19:20A lot of the things that we do now is driven by just me pushing and going, guys, what's next? Who else can we help? Like who lost everything? How do we show up for them? And just living in that kind of impact mind frame just always kind of kept me going and searching for a way to be super impactful for people. Hey, I don't know if you remember this, but when we started this podcast, we entered into a social contract. I would spend time, energy, and money producing this podcast, interviewing these individuals and giving you insights into how to build, buy, start, grow your business. And you would like, subscribe, and leave me a five-star review.

19:56Now, out of that, we both get to talk to really cool people and hear really cool insights. We both get a ton of value. But I just want to help you keep your word. So would you do me a favor? Will you go leave a five-star review for me? on Apple or Spotify. It would really help. And if you want, even share this with a friend. When did the idea for True Classics come? Like, was it in 2018? I know it launched in 2019. Ironically, looking back, and I made a post about this a while back, the idea started when I was like in my, like 19-ish, but I had forgotten about it as, but I had told my brother about it.

20:29And he reminded my mom like a couple of years ago, cause he had seen on the sidelines, True Classic, he's like, remember, I remember when Ryan told me that, when we went into Caraloja and they didn't have his black shirt that he was going to start a t-shirt company someday so that he could always have the t-shirt he wanted. And I was like, oh my gosh, I forgot that I had told him that. It was insane full circle moment. But when did I actually take it serious? It wasn't until about, I would say, 2018 where I was toying around with a few e-commerce ideas. I wanted to do Lab Diamonds was an industry I was really interested in.

21:07It was like incredible value for people. There was a couple of things I wanted to do, but the t-shirt thing, I just, the more I looked at the competition, the more excited I got about how boring the space was and how much I could make an impact in this particular space. Like I didn't feel that anyone was doing anything amazing in apparel. Well, and that's what I want to drill in on is because I think that maybe for the first time, you're old enough, you're mature enough to kind of look back and assess the state of the field. Okay, these are my skills. This is kind of what's going on. But were you actually looking at it that way or was it still, hey, this is kind of just where my curiosity is leading me and it just so happened it worked out.

21:48Like how calculated was it and how just it happened because water flows downhill? With the t-shirt thing, I mean, look, I would say that part of it was just, I was facing, I knew I needed to solve a problem. Like that was like the first and foremost, right? So any business I was going to get into, it was not going to be a lifestyle brand. It was going to be a problem solving brand. And so the t-shirt thing just kept staring me in the face. Like I just kept going into my closet, being underwhelmed, asking myself why, going looking up online, not really finding any good solutions and then going like, why is everyone doing it wrong?

22:23Why aren't they trying this? Why am I not seeing any great marketers in this space? Like I bet you if I enter this space, I'll make such an impact so quick because it's so boring. and so archaic. These brands that have been doing it for 50, 60 years are not enormous because they're wildly creative and they've graded DTC. They just have unbelievable distribution and they're in every big box retailer and they've been doing it forever. And I'm just like, where are the talented creatives in this space? Why haven't they lashed onto this space yet? And so that's kind of where it started. Okay, I love that framing of it because it's like you identified a problem, which is these shirts don't fit very well.

23:02I think I heard you talking about it. You're 6 '2 and like 175? Yeah, yeah. Okay. I'm a little heavier than you. I'm like 185, but I'm 6 '2 as well. And like, I just always had a problem with shirts. Either the sleeves were too short or like the bottoms wasn't long enough for, you know, for the top. When you were doing the research, were there really no companies or were they just not marked? Okay. They just, okay. So I'll tell you where they were missing. What you just described wasn't being talked about. and now there's like a million companies who try to do a version of true classic but when i started this no one was talking about fit like that like nobody so i was basically just like yes it's underwhelming yes people are creating solutions but they're definitely not talking about the way i want to talk about it and they're not getting super narrow and precise which i think was really the key to getting people to focus on who we are and what we are and what we stand for so like solving the three problems of number one, fit being like the biggest problem, feel the comfortability of just everyday clothing.

24:03And then price being this, like, I want to make a premium garment at a reasonable price. Instead of charging a hundred dollars a shirt, I want to charge like 15 bucks or whatever it was. And that was really the three things that I was trying to solve in the market. And no one was nailing it. Like as a consumer, you knew that there was a problem. You did a little bit of research. You saw some of these companies and then as the business guy who literally had had a digital agency obviously you have the music experience as well you're like nobody is marketing this oh it just was kind of the night like the meeting of the two isolating the actual problems and talking about it which actually is really good news for literally anyone starting any product was if you look at an industry and you look at a vertical and you feel very underwhelmed that means there is unbelievable white space for you to go off and do something amazing.

24:51Now that takes vision. It definitely takes a certain amount of real confidence to execute on that vision. And that was what I had built into me from all those years of doing so many things. So it's just the perfect storm of vision, opportunity, seeing a white space, and then me having enough confidence and a little bit of crazy to go like, am I really going to start a t-shirt brand in this day and age? I told my wife this idea and she was just like there's got to be something else like you're not really gonna try to sell like plain t-shirts right like this isn't and i'm just like no no no you don't understand like these guys are dinosaurs like they're just they're underdoing it i'm telling you i'm gonna make head i'm gonna make a lot of i'm gonna make a lot of um swings at this and it's and it's gonna make waves and i'm gonna show you and that's just that's exactly what happened that's funny my wife would have been like uh do are we still making 100 grand a month with the agency yeah yeah okay whatever do whatever you want to have you heard i'm sure you've heard of the like the fat pitch philosophy from warren buffett he got it from ted williams ted williams is one of the greatest hitters of all time are you a big baseball fan or not so much i used to be when i was young yeah okay so the crazy thing about baseball is that for to be a hall of famer basically you got to hit the ball 30 of the time 30 three times out of 10 and all of a sudden you're a hall of famer that's how hard it is to hit a ball in baseball well ted williams he played probably 80 years ago, he had a couple of seasons where he hit the ball 40 % of the time, four times out of 10.

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26:19It's crazy. And he would talk about this thing where he broke down the strike zone into 27 different sections and he knew exactly where his fat pitches were. Yes, the ball would be in the strike zone and it was technically hittable for him, but it wasn't his, his fat pitch. There was a certain area where he had a much higher percentage chance of, of hitting the ball. And so we'd wit, he'd sit and he'd wait on those pitches until it entered the head zone. And obviously he'd take a hit. Warren Buffett has taken that and he's like we at berkshire wait for our fat pitches we're not just like placing a million bets on a million things we know what we know and when we see an opportunity we go big and i i love that philosophy because i think that for many of us there's a couple times in our life where there's a fat pitch and we got to make a decision knowing everything that i know i have an unfair advantage i think i see the future i'm gonna go ahead and make a bet on this and the question is just whether or not you're willing to bet big.

27:11And for you, it sounds like you were like, I think this is a fat pitch. It was, but I also felt like even if it doesn't work, so what? And I think that a lot of people I talked to, a lot of young entrepreneurs are so worried about failure and having failed so many times, it just did not feel like it was such a risky thing for me to try to build a t-shirt brand. If it doesn't work, I just close shop and move on. Like I didn't care. I was just like, I'll move to the next thing, right? It would have been, if it wasn't true classic, it would have been a lab diamond. If it wasn't lab diamond, it would have been matcha.

27:43I would have just kept going until I nailed something. It just so happens that true classic work. There is a component of business to where it's like, you can go into a million things, but knowing what to focus on is, is truly very important. And I was, I was passionate about this particular space. I was, I also did my homework, right? So for anybody listening that is in that, like, I could do anything mode. Yes, you can technically, but you have to do something that you actually want to bleed your eyes out doing every day for years and years and years, or you will absolutely not make it. You have to love providing real value in the form of some product that you can stand behind.

28:26It can't just be like, I saw Mr. Beast make chocolate bars. I want to make chocolate bars. It just can't be that because you'll get so tired of chocolate after six months that you'll never want to look at it again because it'll be such a difficult business. So like I was willing to play the long game on clothing to try to make it work because I loved it that much. But a lot of it, again, goes back to like when you say the 40 percent doing my homework got me to that 40 % where I knew I was, it was higher than 40. It was like 80 to 90. That was what I was swinging on to get there because I did so much work and research and research and just every night on my phone, talking to apparel people or going into Facebook groups or going onto Amazon and validating product options.

29:16And like, I was obsessed with learning. And I think that is, that is a big part that people don't talk a lot about. yeah i think the curiosity of pieces is massive it's huge i'm just curious did you ever struggle with like man what am i doing i wasted so much time because you could easily look back on 10 years wasted music poker whatever absolutely dude i feel like music and poker were a huge waste on a lot of levels but i i do derive a lot of skills from those industries that i have been able to pass on through business music, but the creative poker with the incredible risk tolerance. I mean, you know, we take bets here on product inventory to the tune of tens of millions of dollars on a whim in a, in a boardroom in a 30 minute meeting.

30:01So like if I didn't have so much at stake in poker in the early days, and I was able to put my rent on the line today, I would not feel comfortable making those bets, but it's just, you know, I have a lot of grit and determination and will to bet on myself and the upside that it just feels normal for me to take bets at this point. Looking back though, do you look at it now and you're like, okay, yep. It's a good thing that I had those experiences. It is now. That's what I was going to say is like close to it or even like during it, were you beating yourself up? Were you like, I'm such a moron or did you move on pretty quickly?

30:39I did move on, but like, I think at the time you reflect on how much time wasted there was. And man, I wish, like when I talk to guys that are young and they're crushing it, I'm just like, so jealous. I'm like, Oh my God. Like, cause I punted my twenties. So I'm just like, you're already this far along in your mid twenties, dude. You're going to absolutely crush it by your mid thirties. Like it wasn't until my like early to mid thirties that I started crushing it. So, but I also didn't beat myself off about it too much. I was just like, I was always an eternal optimist so i'm just like yeah you know chalk it up to a few failures but we'll figure it out eventually i don't know maybe this is me just making myself feel better i think life's about finding leverage points where you can you can bet really big and some people find those leverage points in their 20s and some people find them you know when they're 40 and they launch a business and the timing sucks yeah i'd love to have found those leverage points earlier but also frankly for me i wouldn't have been able to take advantage of some of those leverage points in my 20s because I didn't have the maturity.

31:43I didn't have the dexterity or the knowledge to actually take advantage of them. So as much as I would have loved to be killing it, I just wouldn't have been killing it, which is hard to say sometimes. You know, I wish I could say that differently. I think leverage is an interesting game that you bring up because even at this level, six years in, I am constantly trying to create leverage for myself. And so has Ben, like we're one of my executives, like that is the full game at our level is like, How do you create leverage and get your time back so that you can focus on the things that really matter?

32:14I want to focus more on philanthropy. I want to focus more on making people feel good, making people look good, helping with initiatives that help the company or help homeless people or whatever it is. I want to do the stuff that I want to do, not the stuff that the business demands of me because, man, does it really demand every second of my attention. Let me step back. How quickly did you get to hundreds of millions of dollars in revenue a year? Two years. okay i'm gonna say that's because of your genius is that fair it's partly i hate giving myself all the credit but no i what i would say is like part of it is i had amazing co-founders that is that truly is part of the luck factor here is like i had great co-founders that believed in me who were willing to not step on my toes and just let me be me and do what i do and not fight back on things, but actually be real leverage for me in spots that I'm deficient in.

33:11So like Matt, for instance, was like the CFO finance M &A guy. Nick was like the apparel manufacturing, knows how to talk to that world and bring my apparel vision to life guy. And the three of our trifecta DNA just played the absolute perfect full circle picture of what it took to really build this business. So - Yeah, said a different way, I would say. you played your role to perfection right it's like you were steph curry on the warrior you needed to just shoot freeze and you yes but i need to dream on and i needed i needed clay thompson like i had to have those guys to make it all work when did you get to the point where you're like you know what i know that my native genius got us here but now i need to kind of pivot out yeah right after we hit 100 million so basically year right after year two we hit 100 million and I was like, okay, it's getting too big now.

34:05And I don't, I'm uncomfortable managing this size of a team. I've never dealt with like HR and like all this other bullshit that came along with business. I had to just like figure out on the fly. And also just like scalability issues that I had never encountered or dealt with and 3PLs going out of business. And I mean, you name it, dude, there was like a million fires. Even to this day, we have a million fires, But it wasn't until I brought Ben on, who's our current CEO, that he created unbelievable leverage for me. And he was a version of me, but even more intelligent and just like could figure any.

34:43He was like a UCLA grad, business grad. Like the guy just he worked at Meta, like uber smart. Like, you know, he's always the smartest guy in the room. And that is what it takes to create leverage. You got to find those people. And then you have to also convince them to come aboard and see the vision that you see. Because he had a really cushy life. He didn't need to come to this, you know, fire startup where everything's just chaotic. It's like a zoo here, man. It's just wild animals running around in the office like every day. It's just nuts. Oh, my gosh. Dude, I mean, that's the thing. Whether it's a$100 million company or a$5 million business, as you grow, you hit new inflection points.

35:21And it's like, okay, at$250 ,000 in revenue, my skillset was amazing. And a million dollars in revenue. I don't know what the freak I'm doing. I got to bring other people in. Was it hard for you to recognize that? Or was it pretty obvious? No, it wasn't hard because I was drowning. And I was just like, I'm very, I have super high awareness of what my capacity is and what my ceiling is talent wise. I knew that I would always be good for this company in the creative aspect. Like I still, to this day, I can have creative just about anybody. It's just like my thing. Like I'm just, that's what I'm really good at.

35:54Not so good at ops, not so good at finance, not so good at many parts of this business. But what I am good at, I'm the best at. And that is why I'm still kind of useful to this company. But I would say that like in the early days, we had just a lot of scrappy entrepreneurs. Like everyone that worked for us was like a multifaceted jack of all trades kind of guy. And that worked really well in the early years because everyone was doing the job of like five to 10 people. now there you need like absolute specialists in everything that you do like you need a real cfo not like a guy who knows finance and accounting a little bit right like it needs to be really focused so that's a big transition everyone's got to make though have you found that transition hard because what i've noticed i've done it a couple times with businesses that have scaled the people that you hire to go from let's say zero to 50 or zero to 100 million they're not the same people who i would hire completely different completely hard sometimes because either they leave because they're not happy anymore or you've got to let them go because like the team is suffering but that's freaking hard because they were there in the beginning it's the hardest part of it it's there's no question and i think you know this that the people component to business is always the harder part of business i actually think business is wildly easy.

37:12I think it's complex, but the challenges are always wildly easy to solve in the big scheme of things. There's just nothing, Ben and I always say that, there's just like nothing we can't figure out. And we always do. Even when things seem stacked up against us and there doesn't seem to be a way out, we find a way out. But I would say people are so unbelievably complex and they're going through their own journeys that you have known nothing about. And then one day they just up and quit. And then you find out later that they were so in their head about something and that wasn't even reality. They just were in their head about it.

37:45They didn't bother to reach out and they were stewing on it and then they just gave up and quit. And so, you know, I guess you learn to touch base more with people and find out where they are in their current journey. And that helps you get to the truth of where they're actually at versus where you think they're at because people play a game, right? They, they act like everything's fine. And then one day they're just gone. And then you look back and you're like, damn, what could I have done? Like they didn't actually need to go anywhere. I would have actually promoted them. I would have given them more money, more opportunity.

38:16I would have given them everything, but they were just like, Oh, there's no more upside here. So I'm, I'm capped on the ceiling here. So I got to go find something else, but it's very difficult. I've done it a couple of times and I hate it where like, I find out somebody was like, Oh, I thought you didn't want me here, but you know, like, we'll like reconnect a year later or something. And I'll be like, dude, no, I hurt my feelings. Like I, I really, and you were here from the beginning and I enjoy working with you. What did I do wrong? Like, I feel like I screwed up a relationship that I had actually found really valuable, but you don't have time to like sit and stew and figure that out.

38:50You got to move on to the next thing. Cause there's another fire the next day. It's kind of, it's a hard part about scaling hyper fast. Yeah. And if you have a lot of people, how can you possibly sit there and talk to every single one of them every single day? Like it's just, it's quite literally almost impossible. You can touch base very quickly, but like if you don't sit there for real extended time periods, you're never gonna get to the actual root of where they're at. And that takes really detailed questions. It takes a lot of them opening up and no one's gonna just sit on a five minute huddle and open up like really quickly off the top of their head about what's really happening deep down.

39:27Like it just doesn't work that way, right? So you're right. It's a difficult journey though. So it's hard though. It's hard to make the switch because you, at least when you're building businesses, you feel productive when you're doing something. I ran a Facebook ad today and I got a, you know, three X row as right. Money hit the bank. I immediately see it. There's immediate feedback when you start growing and you realize, Oh, people are the ones who are executing on my vision. I got to go build relationships with them. There is not that immediacy with the feedback. Did you find it hard to make the switch of like, okay, I got to be more people focused than necessarily ops focused or did that just come over time?

40:03I would say it came over time. I also learned the hard way like you, where like people would leave and then you'd find out why you need to realize in hindsight that you, that like, I just didn't do enough to communicate. And there's so much of my job really needs to be that, even though I do need to actually solve problems for the business because there's so many problems. So it's just this constant juggling of people's feelings, what you can help them do in life. But then also like the business is a machine that I just have to adhere to. I have to give it my attention as well. So you need to find other really great managers that can do that job for you, I think is really the punchline.

40:42And now we do have those people who can help soften and figure out where that person is without me actually having to be the one to get it out of them. Are you continuing to focus on the stuff that you feel like is your native genius? Like, are you focusing a lot on the marketing, creative branding? Yeah, I would say that it changes. Like there's some weeks where I am heads down trying to solve a really tough problem. And there's other weeks where I'm just like making content all week. And it's like amazing. So it just ebbs and flows with the state of the business. If you could go back to you, 20-year-old Ryan, or let's say 25-year-old Ryan, who's just like in the middle of it, what advice would you give yourself?

41:20I would have told myself that I don't need to make music. I don't need to make money from music. And I don't need to make money from poker. I can do both of those things and just have them be fun hobbies. And I don't have to do it for a living to actually make a living. I can be completely fulfilled doing something else, making money, something being an entrepreneur or a business. And I would have just, it would have started me a lot sooner than later. You know, it would have saved a lot of time and energy. but then in hindsight, you know, it did help develop those muscles that got me here in the first place.

41:54So it's hard to say like, would I've changed anything? Probably not. Would it have been nice to maybe take a few years off of each of those industries and give back to the business? Probably. Yeah. When I talk to people, sometimes they're like, I would have told myself to not be so hard on myself, you know, go easier. You're going to be fine. I'm always like, well, did you end up being fine because you were hard on yourself? You know, I'm not saying sit in your closet and be like, you stupid idiot. You're the worst person I've ever like, yeah, don't do that stuff. But you kind of needed that fire to get to the next level.

42:25What advice would you give to a 30 year old, 35 year old, 40 year old who is sitting there thinking, gosh, what have I done? I got, okay, I have some skills. I didn't really leave my dent in the universe. I didn't really leave my mark. What am I going to do? I think that there is, listen, there's a couple of things going for people that are in that age range with what we have in our day and age, which is like this unbelievable technology and AI and all these things that are evolving very quickly to help businesses get more visibility and do a lot better, a lot easier. I mean, just to live in a time where we have the ability to leverage Facebook ads is one in a trillion.

43:04Like there's no true classic without Facebook ads. I'll just, I'm, I'm, I'm happy to admit that, that like there is a certain amount of luck that I lived through the years of Zuckerberg and a lot of businesses, you know, from the nineties and below just didn't, and they didn't have that luxury. So, you know, that I'm very thankful for, but what I would say is that, you know, you don't need a lot of money to start something these days. That's a, that's the great news. You have an unbelievable distribution engine like Facebook that you can test things on at a very small scale for not a lot of money.

43:35I mean, you can start drop shipping items and flip a few products for a few hundred bucks very quickly and easily and turn a profit on little to no effort on literally a few hundred bucks on literally just some elbow grease, getting some products in a Shopify store, connecting the right apps, having everything kind of working for you. That's provided you've done the research to know how to set it all up correctly. The white space is endless for starting something. I think people just get in their heads about, I got to have the perfect plan in place to get it, or it's going to fail. And it's like, yeah, so what?

44:12Then what? Then you do it again and you try something else and then you fail again. So what? Then you move on again and you just keep going and going and going. But people are stuck in this mindset of like, I got to get it right the first time or I'm dead. And then I just instantly die. The end. I can never do anything again. It's like, dude, life is long. You have a long time to figure this out and you don't have to do a product for like 50 years. You can try it for like two or three months. See how it goes. What did you learn? Did it grow at all? If not, kill it. Try something else, right? So like nothing is final.

44:45I get this like attitude from people that like, if I do this thing, it's the end of me if it doesn't work. And it's like, my God, dude, it's not that serious. Yeah, and it's almost like the failure. Let's say you do do something and you fail. It kind of sets you free because you realize, oh, that's what I was worried about. The world didn't come crashing down on me. It just went away. Dude, I love that. I love that. That's what dropshipping is good for. Honestly, if there's one thing I would leave people with, it's that if you learn dropshipping and you learn that a product doesn't work, you move on to the next product.

45:17And then if that doesn't work, you move on to the next, and you just keep going till you find a winner, and then you scale a winner, and it makes you realize that I actually had to fail 12 times to get to the 13th winner, right? And business is exactly the same way. Now, hopefully you don't have to fail 12 businesses to get to the 13th business, but you may have to eat a few businesses, three or four or even five before you get to your scalable e-com company that gets you to where you want to be well it's building the muscle it's just you're building like muscle memory on identifying oh this product works this doesn't work oh this this marketing creative works this marketing creative doesn't work that how i treat people this way works how i treat people that way doesn't work like every single experience can be a muscle building experience and it's easy to say looking back on that right but i i'm just like encouraging you that if you're in the thick of it right now and you feel like what the frick am i even doing everything is compounding and there will be a point in your life where there is a you can take a fat swing and you're not only just gonna get one fat swing you'll get multiple fat swings the trick is don't die yeah exactly don't kill yourself over one mistake i would also say that like if you have a way and i don't know if there is a way.

46:29I'm sure there is. If you have a way to develop creativity, I do think it's the ultimate hack in business. I think without it, we are just another t-shirt company putting out average content like everybody else. And we're not getting this surge and through line that puts us above everybody else. If you have a way to develop that creativity, I think you'll look back and realize how unbelievable of a superpower it actually is in business, not just with product innovation or creativity, but how you deal with people, how you show up in meetings, how you find solutions in a room of people that, you know, I sit in these rooms sometime with these people who are all smarter than me and somehow, some way I'm able to navigate out of a situation quicker than all of them because creativity leads you to the real answer, not what the smartest answer in the room actually is.

47:20Right. And I know my strengths, but I also know that creativity breaks through all the noise and all the intelligence hands down and it has gotten me some unbelievable solutions that none of these smart people could have thought of because they were so stuck in what they thought the answer was they weren't able to paint outside the lines and man that painting outside the lines is truly the real intelligence you need to seek i absolutely think creativity can be developed jerry seinfeld talks about this a lot where he sits and writes every single day that's a part of his process he writes whether he feels like it he writes whether he doesn't feel like it it's every single day and so yeah is there probably some level or some degree of innate creativity that some people have more than others sure just like there's going to be people like lebron james who can just jump out of the gym freaks yeah that are just freaks but then there's going to be other guys who are like i'm going like way in my sports bag here bruce bowen they're not freaks they just worked at their craft every single day and they they tried and they got in and they figured out how to do something that was replicable.

48:23I think that creativity is very similar to that. There is definitely some innate creativity that you just either have or you don't, but you can develop the muscle. You can understand what is it about this phrasing that people like, how do I, how do I say something that captures attention, but doesn't close the loop so that someone is actually willing to click to figure out what's on the other end of that ad creative. There are definitely ticks, tricks, and tactics that you can do. It just takes work it's just work by the way have you been playing with sora at all oh yeah i am obsessed it's ridiculous dude i think i have 700 soras in my in my draft folder like i just sit in my bed at night now and i don't scroll anymore i just create sora videos non-stop for like are they in your draft folder because you're like because you're like i can't i can't like be that guy who's releasing no i don't care about that i don't care about that you know what it is is like Like Sora is one of those things where you have to do 10 to 15 iterations before you get a really good one.

49:20So I'll prompt it. I'll get like a B - version. And then I'll prompt it again, and I'll get to a B. And I'll have to keep prompting it until I get to the A because it's not a perfect system. It's wildly better than VO3, though. I will say that. But it has been such a game changer. I just don't think people really realize what's happening with Sora just yet. but it is mind-blowingly amazing. Okay, what are you using it for? Like, what do you have 700 drafts for? So right now, I'm just using it for organic content on Instagram. Like, I'm just creating posts that are funny and I just put them out.

49:54And I just put them out on Instagram and people laugh and say, this is hilarious. And that's it, that's it. I'm just, it's just purely entertainment purposes. I don't need to make an ad. Yeah, I don't need to sell anything. I don't care about that. But yes, you can build ads with them. You can sell things with them. but I don't treat it like that personally. I just like to be creative and funny. Well, I mean, again, you're building the muscle because I'll do the same thing, but you learn over time, you're like, oh, I need to prompt it this way. Oh, I actually need to tell it explicitly to do this or not say anything about this.

50:25So it's actually getting better in that respect than ever before. So that is where VO3 came short. You used to have to prompt in like JSON language or some sort of arbitrary code language to really like nail the scene the way you wanted it to look. Whereas Sora, you can go as basic as one single sentence and it gets you like 90 % of the way there, which is the advancement from where Vio was to where Sora is. And that's what makes it so much better because it levels the playing field with creators where you don't have to be an engineer to write a prompt anymore. You can just literally write a sentence that's funny and say, you know, I want to make a like have a guy win true classic and a price is right scenario.

51:16And boom, Bob Barker comes out and he's like, the price is right. And he opens the curtain and there's a pack of true classic sitting there. And you're just like, oh, my God, I did that in 30 seconds with no effort. but that's what i'm saying is even understanding how to put the the simple sentence in place in order to get that version of sore that even looks good is still a skill like how to prompt chat gpt to give me the answer that i want is so you can do that in chat gpt a little bit like you can say hey i got sometimes i'll go to chat gpt and go i want to create sora videos and i want to do it in a 10 second framework right and it's going to be in portrait mode so i want to do it around this concept.

51:58Can you give me some ideas that fit within 10 seconds, make them super short and punchy, make it dramatic, make it a thriller style, whatever it is, like whatever you're going for. And it'll give you like 10 versions. And then you can kind of look at the 10 and go, this one's kind of good. Ah, this one's what I do is I'll take one that's kind of good. And then I'll put my sauce on it. And then it'll get me to the better version. So it doesn't come out perfect on ChadGBT. And then you just copy that little excerpt, throw it back in Sora and unless Sora try to create it. Have you ever done a series?

52:29That's the only thing that I can't quite figure out is the continuity. No, not yet. That's my thing. It's like, I'd love to do six of these 10 second videos and stitch them together. But you won't need to because pretty soon, like they just advanced it to 25 seconds. They were at 10 seconds. Then they were at 15. Now the web version has 25. So pretty soon it's going to be up to a minute and then two minutes. And then you're just going to be able to do one prompt and have a two minute long piece of creative that you won't even need to storyboard at all. You'll just tell it what to do and it'll do the whole thing.

53:00It does have a storyboarding component now on the web application, by the way. They just rolled that out three days ago where you can storyboard the scene and then it'll break it down in increments of seconds. So it'll say like, if you want to do a sentence long prompt, it'll show you how to break it down. So in this part of the sentence, I want this to be about three seconds. And then in the next three seconds, I wanted to do this. And then the last four seconds, I wanted to end with this. And so it gives you kind of a play by play. Yeah. Yeah. I see it. There's a storyboard on. Holy crap. They're already doing it.

53:36It's happening so fast. Dude, what do you think about the way that they released Sora? I'm curious to hear as a product person. Like the invite only thing? Any of it. Before I give you my color, I'm just curious on what you think of how they did Sora. I don't know really the background i just i just know that they did it super privately and it was part of chad gpt and i have an unlimited account because i create way more than 30 a day now i'm just i'm just on fire with it but yeah i i really have no context so the invite only was cool whatever because it creates scarcity but i i think i don't know that he thought of this but releasing it as a social platform could turn out to be one of the most genius tactics ever because what it does is it makes the product stickier.

54:22It's not just some guy sitting, for most of us, most people who aren't you, what am I going to create a Sora for? I don't need to have a branding thing. But if you're on Sora and I'm on Sora and we're friends, dude, I'm sending you videos all the time. Hey, look, this is us on the top of the Eiffel Tower in 1870. Dude, listen to this. Last night, I'm sure your wife loves this show, but last night, I had my wife create an account and do a cameo just so I could create a love is blind between me and her on Sora. It was amazing, dude. And literally we both come out and we're like, oh my God, wow, you look great.

55:03And she's like, yeah, you're taller than I thought. And like it's this whole like it was she was dying. She's like, this is the greatest thing I've ever seen. Yeah. Yeah. And so now they've created this product. And how do they get people to use it? They create the social aspect to it. And so now they're sharing stuff back and forth. I just think that that's so smart because it's not just this niche product that's kind of stand like nano banana standalone VO three stand like what else? Very smart. Yeah, you're right. And the component of the remix is what makes it so easy to go. Oh, I love that creative.

55:34Let me remix it and do my own prop. So if you see like, you know, some monkey or some like Donkey Kong swinging from building to building, you can just be like, put my grandma swinging building to building. And then it instantly changes it to your grandma. And then it's just this old lady swinging and you can just do iterations of everyone else's creative. And it helps the creativity just flow unlimited, man. It's, it's amazing. How do you view that? Like you're a creative person. You like you, you do this stuff for a living. How do you view this impacting the ability to run and generate ads? Is it, I think it's a future job.

56:09No, no. I think it's all upside for us. I I think that as long as you're not using it in a way where you are trying to kind of like we're an apparel company and we and we're focused on fit. We don't want to use fake AI models for to show off our fake digital clothing. Like that's the component I don't like about AI. But everything else is fair game, in my opinion. Like everything like entertaining content wise. That's why I'm playing in that space more than anything, because I see more of the upside there. It's just another tool in the tool belt. Yeah, dude. And it's so easy to use. And you don't have to know anything about anything to create content to use this and wield it well.

56:49Do you have any advice? How do you make your cameo look like you more? Like when I create stuff, sometimes it looks exactly like me. And other times I'm like, who the freak did they think I was? I think it'll get better over time. I just don't think it's all the way there yet. I'm with you. Like I've tried to do different angles, different shots. I've recreated the cameo a few times, but a lot of it is lighting. lighting i've realized like you really got to have the lighting dialed in to get every contour of your face and piece of it because that's all it's using is is really what it can see in the camera lens so you got to make the most of the lighting to get the best picture you can and even my wife last night like because she took the cameo without makeup on and then in the love is blind she was wearing a dress but she didn't have makeup on so she was like oh i don't like it it doesn't show i need makeup on or whatever so i'm like oh you have to recreate the cameo with makeup on Like, that's it.

57:42Because like you and I have hours of high definition video that we could upload. Like it could look really, really close to the way that we actually look. Dude, the Sora is the future. It's only getting better. You know, this Atlas just came out with where it's like a web browser, the OpenAI web browser. I'm using it right now. It's unbelievable. I just think Sora is the future. Yeah. And it's a chat GPT is built into the browser. so any page you go to you can just ask it questions and it does all the work for you instantly it's amazing but on the Sora front dude I am so bullish on it I think it's just I think it's changing the game and people just gotta you know start creating fun stuff and treat it for what it is just you know use it for entertainment value would you use Sora to create creatives for like Facebook if you were starting out again to do like drop shipping or something I would do a hybrid probably i would probably always use studios and things but like from a production standpoint dude it's next to impossible to get anything even close to sora for what it costs i mean it's just pennies on the dollar compared to because we do big shoots now and they're very expensive so um i love that all right ryan it's amazing where's the best place for people to come find you twitter instagram website yeah yeah any of them i mean it's just my name you can pretty much find me anywhere go check out true classic.com we have women's dropping in a week so now we have everything men women kids boys girls everything in between so next it'll be dogs and cats i'm sure i don't know what let's go yeah 10 billion dollar brand two years from now 10 billion dollar brand let's do this thing we'll see dude we'll see i love it all right man all right hopefully you like that episode and if you've made it this far you're either really committed or you're stuck doing yard work and you can't actually skip on your phone.

59:29So while I have you, the show is growing, but I have a favor to ask of you. Will you please help me grow the show? I want to reach more people. There's a couple of things that you can do. Like and subscribe is the simplest thing. Obviously you want to get notifications for when the next episode is coming out. But if you go the next step, will you leave me a review five star on Spotify or Apple? What that does is it tells the algorithm that, Oh, Hey, this is a high value podcast because more people are leaving reviews for it and it then pushes it out to more people. So that's why when people are like, will you like and subscribe and put the five-star rating?

1:00:03It's not just to make themselves feel better. It's actually to get more exposure for the show. So if you do that for me, I would greatly appreciate it. And I'll see you next time.

From the publisher

MY NEWSLETTER - https://nikolas-newsletter-241a64.beehiiv.com/subscribe


Join me, Nik (https://x.com/CoFoundersNik), as I interview Ryan Bartlett, founder and CEO of True Classic (https://x.com/@RyanBartlett)


From failed musician and poker player to billion-dollar t-shirt brand founder, Ryan Bartlett's entrepreneurial journey is proof it's never too late to start a business. In this episode, we explore how Ryan built True Classic from zero to over $100 million in revenue in just two years, selling 30+ million t-shirts and becoming one of the fastest-growing e-commerce brands in the apparel industry.


Questions This Episode Answers:

Is it too late to start a business in your 30s or 40s?

How do you pivot from a failed career into successful entrepreneurship?

What skills from music and poker translate to building a billion-dollar business?

How did True Classic grow from $0 to $100M in just two years?

What is the "white space opportunity" strategy for finding winning business ideas?

How do you identify which business idea to pursue (the "fat pitch" method)?

When should you transition from founder-operator to hiring a CEO?

How do you scale a team from scrappy generalists to specialized experts?

What role does creativity play in winning at e-commerce and digital marketing?

How do you build risk tolerance for making big inventory and business bets?

What are the three core problems True Classic solved in the t-shirt market?

How do you compete in a "boring" or saturated industry like apparel?

How important are co-founders vs. going solo as an entrepreneur?

What's the best way to test products cheaply using drop shipping?

How do Facebook ads and paid media drive D2C brand growth?

Why do employees quit without warning and how do you prevent it?

How will AI tools like Sora change marketing and ad creative production?

Should entrepreneurs use AI video generation for Facebook advertising now?

What's True Classic's expansion strategy (women's line, new products)?

How do you balance profit with purpose and philanthropic impact?


__________________________

Love it or hate it, I'd love your feedback.

Please fill out this brief survey with your opinion or email me at nik@cofounders.com with your thoughts.

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__________________________

This week we covered:

00:00 – Intro: Who is Ryan Bartlett / True Classic story

03:05 – Failing in music & poker for a decade

10:08 – Moving from poker to digital marketing

12:25 – Creativity becomes a business advantage

14:49 – Compounding skills over 10+ years

17:14 – Running a $1M/year marketing agency

22:01 – Solving fit, feel, and price in clothing

24:19 – Why boring industries have big opportunity

26:44 – The bet that launched True Classic

31:33 – Leveraging experience & risk tolerance

33:57 – Scaling to $100M and needing a real team

36:12 – Creatives vs Operators

38:33 – Why people management is the hardest part

40:45 – Staying in your area of strength

43:12 – You don’t need perfect planning to start

45:33 – Failure builds the muscle

47:57 – Creativity is the real advantage

50:20 – AI + Sora + creativity for content

55:02 – Sora is changing marketing

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