Execution Monsters: True Classic’s Ryan Bartlett & Ben Diamond

29 Jan 2026 · 1 h 47 min · 52 chapters

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Podcast Summary: OPERATORS - Execution Monsters: True Classic’s Ryan Bartlett & Ben Diamond

Episode Overview In this episode of the OPERATORS podcast, hosts Matt Bertulli and Mike Beckham sit down with Ryan Bartlett and Ben Diamond, co-founders of True Classic, a successful apparel brand that has achieved approximately $300 million in sales. The duo discusses their journey from unconventional backgrounds to creating a formidable DTC (Direct-to-Consumer) brand focused on producing high-quality, affordable clothing, primarily white t-shirts.

Key Themes and Discussions

  1. Background of the Founders
  2. Ryan Bartlett: Former musician and professional poker player.
  3. Ben Diamond: Former executive at Meta, contributing strategic expertise.
  1. Rapid Growth of True Classic
  2. Achieved over $100 million in sales within two years and projected to reach $300 million.
  3. Emphasis on being bootstrapped and profitable from the start.
  1. Business Philosophy
  2. Execution-Driven: Described as "execution monsters," focusing on speed, fit, and customer satisfaction.
  3. Customer Value: Commitment to providing value rather than maximizing margins at the expense of customer satisfaction.
  1. Product Strategy
  2. Focused on simplifying product offerings by cutting 80% of their catalog to concentrate on what sells well (t-shirts).
  3. Importance of high-quality materials, fit, and customer feedback in product development.
  1. Marketing and Advertising
  2. Discusses the ineffectiveness of large brand activations and the need for genuine connections with customers.
  3. Highlights the shift towards leveraging AI-generated content and influencer partnerships for marketing.
  1. AI and Technology
  2. Excitement about using AI for creative processes and brand innovation.
  3. Potential for transforming marketing strategies through generative AI tools.
  1. Growth Challenges
  2. Navigating tariffs and market changes leading to significant profit boosts.
  3. Importance of finding a balance between scaling the business and managing complexity.
  1. Philosophy on Giving Back
  2. Emphasis on generosity as a core value; sharing wealth and resources with the community.
  3. Personal anecdotes about giving poker chips to Uber drivers as a means of spreading positivity.
  1. Future Vision
  2. Aspirations to grow True Classic into a family-wear brand.
  3. Plans for international expansion and increased presence in retail environments.

Key Takeaways

  • Execution and Speed: The importance of rapid execution in decision-making and operations is crucial in the eCommerce landscape.
  • Customer-Centric Approach: A relentless focus on customer satisfaction and product quality is fundamental for longevity and profitability.
  • Simplicity Over Complexity: Reducing product lines allows for a stronger focus on quality and customer needs.
  • Community and Giving: The founders believe that giving back to the community enhances brand loyalty and customer engagement.
  • Continuous Improvement: Constantly evaluating and revising strategies is key to sustaining growth and adapting to market dynamics.

Final Thoughts The episode reveals the synergistic relationship between Ryan Bartlett and Ben Diamond as they navigate the complexities of building a successful brand. Their focus on execution, customer value, and community engagement serves as a model for aspiring entrepreneurs aiming to thrive in the competitive world of eCommerce. They exemplify how a purpose-driven business can create significant impact while achieving financial success.

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

Chapters

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Achieving $100 Million in Sales

0:00 to 0:45

Learn how True Classic achieved over $100 million in sales profitably and quickly.

“We crossed$100 million in top line sales.”

Relentless Execution and Overcoming Challenges

0:45 to 2:40

Discover the importance of relentless execution in business and how friction leads to growth.

“But for the greater good, the number one value true classic, move the needle.”

The Unique Backgrounds of Founders

2:40 to 4:05

Explore how unconventional backgrounds contribute to success in e-commerce.

“you spend$5 ,000, but you have to use an invite only URL and you need a code to get access.”

Founders' Early Days and Risk Perception

6:50 to 8:25

Understand the risks and early challenges the founders faced while starting True Classic.

“We had a dinner with all of our ownership group a couple of weeks ago.”

The Synergy of Founders

8:25 to 10:00

Learn how Ryan and Ben's contrasting backgrounds and skills create a strong partnership.

“Ryan, did you know that you wanted to do this with like these people though?”

Market Insights and Customer Obsession

10:00 to 12:15

Explore how True Classic's focus on customer needs and market insights drives their success.

“How did it take you guys a while to figure that out?”

The Importance of Fit and Quality in Clothing

12:15 to 14:00

Discover how True Classic prioritizes the fit and quality of their products to stand out.

“And then when Ryan reached out, I actually had the same exact reaction that you had.”

The Essence of True Classic's Philosophy

14:00 to 14:40

Discover how True Classic's focus on fit, feel, and price sets them apart in the clothing industry.

“Because as simple as it sounds, really there was nobody in the market that really served the customers the way they wanted to be served.”

Creative Marketing Strategies

14:40 to 15:20

Learn about the innovative marketing tactics that made True Classic's shirts appealing.

“as in like half or less off than the equivalent, if you will, designer shirt or other premium shirt, you ultimately win.”

The Side-by-Side Comparison Strategy

15:20 to 16:40

Explore the effectiveness of using simple visuals to convey product quality and value.

“you're doing great marketing and the scale was just unbelievable.”
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Narrow Focus for Greater Impact

16:40 to 18:20

Understand the importance of focusing on a single product to drive brand identity and depth.

“So if you're just reverse engineering that every single time, it leads you to the right answer.”

Rapid Product Expansion

18:20 to 21:00

Hear how True Classic quickly expanded their product line while maintaining core values.

“Going wide just opens it up to too many possibilities.”

Driving Value Beyond Price

21:40 to 23:40

Discuss the strategy of providing value to consumers while keeping prices low.

“And we coined it for every single person who comes aboard, anybody we interview, is to empower everyone to look good and feel good with the brand.”

Lessons from Established Brands

23:40 to 26:40

Analyze how established brands like Kirkland optimize for quality and price.

“and that's what I see with your product.”

Execution and Entrepreneurial Conviction

26:40 to 28:00

Reflect on the entrepreneurial journey and defining moments of conviction in business success.

“I mean, like, I think that idea that you just said, it's so simple.”

Early Conviction in Entrepreneurship

28:00 to 29:00

Discover the moments of high conviction that entrepreneurs experience when launching their ventures.

“You know, like there, there is nothing fancier.”

The Importance of Speed in Business

29:00 to 30:10

Learn why speed is crucial in business operations and how it affects success.

“You know, and I think that like, but obviously early on you're pivoting around so you don't even know what the right direction is.”

Risk Management and Aggression

30:10 to 33:10

Explore the balance of being bold in business decisions while managing financial risks.

“Like we just talked about it and we look at each other.”

Inventory Management Strategies

33:10 to 36:10

Understand the strategies to manage inventory effectively while maintaining business growth.

“I haven't been through one, but that's exactly how they get there is that they take that same level of aggression and they just go risk on across every decision.”

Collaborative Dynamics in Partnerships

36:10 to 37:10

Learn how partners can amplify each other's strengths and creativity in business.

“And we're not really apparel in that way.”

Empowering Innovation through Ambition

37:10 to 42:02

Discover how ambition and collaboration can fuel innovation in business.

“okay, they're clearly, these guys are at just like a different speed level than I am.”

Revolutionizing Video Production

42:02 to 43:07

Explore how new technology enables high-quality video production at scale.

“and then I just need to check with their people before I go live with it.”

Preparing for Effective Content Generation

43:07 to 44:41

Learn the importance of preparation and iteration in content generation using AI tools.

“Like you're saying, I mean, you're going to want to go the comedy angle.”

Challenges of Entrepreneurship

44:41 to 46:46

Understand the daily challenges entrepreneurs face in balancing business and creativity.

“And all that is what you're talking about.”

Cultivating a Results-Driven Culture

46:46 to 49:21

Discover how to foster a culture focused on results and truth-seeking.

“Like we never get to do this kind of stuff, right?”

Evolving Decision-Making Dynamics

49:21 to 50:55

Learn about the importance of objective decision-making and rapid adaptability.

“Another component, just going back really quickly, I wanted to touch on this because this isn't like a sexy thing, but I just want to like give everybody the dirt.”

Navigating Growth and Inventory Challenges

50:55 to 54:26

Examine the impact of inventory management on business growth and operations.

“We have to do this a lot in CRO where we're riffing about a page and we're going, let's move this and let's take this down.”

Expanding True Classic's Market Reach

54:26 to 56:00

Explore the strategies used to expand True Classic's product offerings and market presence.

“I would probably say that it started getting a lot harder when we scaled people, because people take so much time to train and hire and learn.”

Expanding True Classic's Product Range

56:00 to 58:19

Learn how True Classic expanded its product offerings and geographical reach.

“And we coined, I think there's four main levers.”

Balancing Growth and Complexity

58:20 to 1:00:22

Discover the challenges of maintaining growth while managing business complexity.

“if you're thinking about any big CEO who's like turning around companies, what they typically do is they go into a company and say, that this is a complete chaos and I'm just going to cut the long tail.”

Impact of Simplicity on Revenue

1:00:23 to 1:02:41

Understand how simplifying product lines led to increased revenue.

“Comfort's like the stretchy softy version.”

Navigating Product Decisions

1:02:42 to 1:06:35

Explore the importance of making strategic product decisions for scaling.

“It's like you've already proven out that something works.”

Measuring Growth and Profitability

1:06:36 to 1:10:04

Learn about True Classic's journey in achieving consistent revenue growth and profitability.

“If you cannot articulate well enough how you made something better, faster, cheaper for the consumer, so they should care about it, it's going to always be harder to actually gain the product market fit.”

Ruthless Prioritization for Business Success

1:10:04 to 1:12:08

Learn how True Classic focuses on prioritization to improve their business performance.

“Every assumption that all of us are making on a day-to-day basis went to nothing.”

Defining Growth and Financial Health

1:12:08 to 1:14:08

Discover how True Classic balances growth goals with financial metrics.

“assumptions that you had about the business no longer hold.”

Learning from Product Feedback

1:14:08 to 1:16:37

Understand the iterative process True Classic employs for product improvement.

“It's a really important one because cash flow is what kills companies.”

The Importance of Generosity and Community

1:16:37 to 1:18:54

Explore how True Classic integrates generosity into its business model and community initiatives.

“And then there is another thing where it's like, maybe not.”

Aligning Business Goals with Personal Values

1:18:54 to 1:24:00

Learn how personal values influence business decisions and community impact.

“There is an organizing principle that's bigger than, hey, let's make a bunch of money.”

The Power of Generosity in Business

1:24:00 to 1:25:14

Learn how giving and generosity can transform company culture and personal mindsets.

“And if you come with that mind frame, you will do that in every part of the business, not just employees, but customers and everybody involved.”

Vision for the Future: Scaling with Purpose

1:25:14 to 1:26:43

Discover the long-term vision for the company and the importance of scaling for impact.

“either a poker chip or whatever the gesture was.”

Creating Value Beyond Apparel

1:26:43 to 1:27:49

Explore potential product expansions and the vision for a broader brand presence.

“Where do you see the company in five years then?”

The Importance of Personal Purpose Statements

1:27:49 to 1:29:20

Learn how developing a personal purpose can enhance motivation and success.

“But can it get there in 10 to 15 to 20 years?”

Impact of Generosity and Philanthropy

1:29:20 to 1:30:38

Understand how acts of giving can inspire others and create a culture of philanthropy.

“That's why I like to inspire others to really push themselves, sometimes in really meaningful ways.”

Future Brand Direction and Market Expansion

1:30:38 to 1:31:59

Discuss plans for the brand's growth in various markets and product categories.

“put it out there and let people reflect.”

Rapid Fire: The Titan 10 Questions

1:31:59 to 1:33:15

Engage in a fun, fast-paced segment answering questions about business metrics and personal insights.

“Exactly how and where and when, we are very opportunistic.”

Contrarian Beliefs in Business

1:33:15 to 1:35:08

Explore unconventional views on customer focus and the impact of giving.

“I'm so we've been incredibly focused on that number as a business since literally day one.”

The Essence of Effective Leadership

1:35:08 to 1:36:33

Identify key leadership qualities and the importance of clarity and objectivity.

“I got, this is like teasing up the next question so well.”

Curiosity as a Business Driver

1:36:33 to 1:38:03

Understand the role of curiosity in business success and problem-solving.

“I would double down on what he just said.”

The Importance of Curiosity in Business

1:38:03 to 1:38:58

Explore how curiosity fuels innovation and decision-making in business.

“So then on that, what's the single most important word in business to you, Ryan?”

Intentionality: The Key to Effective Action

1:38:59 to 1:41:04

Learn about the significance of intentionality in achieving business success.

“or even the next product that could completely change the business.”

Lunch Breaks and Work Habits

1:41:05 to 1:43:08

Hear about the hosts' unique food preferences and work habits while discussing their busy lives.

“You could stick literally a shoe in front of him and he would just start eating it and be like, oh, this is a shoe.”

Overrated and Underrated Growth Tactics

1:43:09 to 1:45:48

Discover the hosts' opinions on overrated marketing tactics and the power of building creator communities.

“And I would say your dollars are much better allocated towards Facebook and creative.”
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Transcript

Automatic transcript. May contain errors.

0:00We crossed$100 million in top line sales. Profitably, within two years, completely bootstrapped The growth from zero to 100 million and beyond 150 million in three years True Classic is fitted in the arms and chest to show off all your training I didn't need to complicate my life and go through all this chaos of e-commerce I've got to do more with my life than just make money True Classic to me, it is probably chief amongst them Is like relentless in execution Like you guys are just execution monsters Selling t-shirts seems even crazier to me The fact that you guys were like, yes, we're going to sell t-shirts, white t-shirts on the internet, and we're going to make this a business sounds insane on its face.

0:40The only way you polish a diamond is with another diamond. And it's through the friction, and it's through the arguing, and it's through the fighting. But for the greater good, the number one value true classic, move the needle. We are obsessed with results. One of the things that I think is awesome, guys, is what you're saying is we want to drive more value to the customer and we want to win because we're helping more people to win and we're making it more accessible. They're clearly just like a different speed level than I am. What are all the reasons that they could go faster? Like what allows them to go faster than we could?

1:11What we ultimately want is the truth and we are truth seekers. And we don't let our egos get in the way of what we think or what we want to be right. There's like a discipline that then has to be built. And then really it's courage, like that ability to go back and cut anything, like a channel, a market, a product, even people. I always try to tell entrepreneurs and people that we're talking to to stop trying to do too many things and find one thing that people care about and just build your whole business around that one thing, whatever it is. Am I the only one who's noticed that most DDC founders have really strange backgrounds?

1:45In today's episode, you've got someone who's coming from gambling, and no, not meta ads, like actual gambling. You have yet another consumer founder with agency experience. And you've got a president-turned-CEO who worked at Meta on the now infamous Disruptors team. You've got what seems like one of the most competitive and saturated categories to compete in, and this is coming from a guy who sells phone cases. It's pretty competitive. This is the first time these two guys have actually done an interview together, ever. And today's episode does not disappoint. These guys are absolute legends. in the consumer brand space.

2:17For very good reasons, I have never not learned something from them. And I have yet to meet many operators like this that move with the conviction and the speed that they do. Welcome to another episode of Operators Titans brought to you by AppLovin. And today we are talking with Ryan and Ben from True Classic. Operators Titans is brought to you by AppLovin, the S &P 500 mobile gaming ad platform. Its self-service ad platform, Axon, is now open and they're offering you$5 ,000 in credit when you spend$5 ,000, but you have to use an invite only URL and you need a code to get access. So if you want a free$5 ,000, stay till the end of this ad, go to nine operators.com slash app loving, and you can get access to the$5 ,000.

2:59Ridge has been spending on app loving since day one. There was a private beta that we had access to back in 2024. And it was our number one new channel of 2024. I'm still spending millions of dollars a year with the same efficiency as meta. It's the only place for audio-only vertical videos that you cannot skip. It's unskippable, 100 % thumb stop rate with an average view time of 35 seconds. It is now 5%, 10 % of our budget. And in Q4, sometimes it might be as high as 20 % of our budget. We're going to ramp up throughout 2026. I hope you join me on that journey. You're probably saying, Sean, I don't have the capacity to do another ad channel right now.

3:37I'm maxed out on Meta. I'm maxed out on Google. How do I learn something new? Well, the operators have not let you down. We have a step-by-step playbook with 25 of the best operators in e-commerce history coming together to teach you how to set up AppLovin to be a profitable incremental channel to your digital marketing spend. Go to nineoperators.com slash AppLovin and you'll get the$5 ,000 in free credit and the step-by-step playbook to get set up immediately and start spending. The place I want to start is the two of you kind of don't make sense on paper together. Like you're, Ryan, I was reading your, I guess, like early years in life and all I got was a musician and degenerate gambler.

4:20And then I looked at like Ben. It's still true, by the way. By the way, we talked about this on an operator's pod today. Is e-com basically digital juvie? Is that like where society sends all of its degenerates? Yeah, it's where you go when you have nothing left. You've essentially failed and exhausted every career. And you're just like, well, time to sell products online. Yeah, nobody that goes. I haven't burned any bridges there yet. There's there's people in other parts of the world that don't know about me and why to avoid me. I don't know. I think it's interesting. There was a study that was done about entrepreneurship.

4:58And basically what they found is that credentialing is a huge negative indicator of entrepreneurship. Like the more credentialed you are, the less likely you are to be successful as an entrepreneur. And it kind of makes sense. Like, I mean, we're joking about it, but it's kind of this point that it's like the more that you look the part or you have the resume, you just would never do this. Right. You just know too much where you feel like the risk is not worth it. All you're fed with is like 90 plus percent of businesses fail. Why would I take the chance? Why me? So you're actually feeding yourself with more doubt, whereas you do need to be a bit crazy.

5:34People who are crazy enough to think that they can change their worlds are the one who do. And I think that's a lot of what you see in entrepreneurship. Yeah, I mean, like people thought that when we started Simple Modern, I tell the story all the time that like I'm at Thanksgiving. and one of my uncles is like, hey, how's your Yeti knockoff thing going? Is that still around? And it's like, oh man, like nobody believed in the idea and thought it was crazy. So I'm the guy that got into selling insulated drinkware when it seemed crazy. Selling t-shirts seems even crazier to me. I'm like, the fact that you guys were like, yes, we're just gonna, we're gonna sell t-shirts, white t-shirts on the internet and we're gonna make this a business sounds insane on its face.

6:15which ironically i was incredibly excited i was like the opposite of scared the more i looked into this space i'm telling you the more excited i got about it because i realized how everyone's just underdoing it like everything's a six out of ten even if i do an eight out of ten i'll crush everybody in this market so i really was just really underwhelmed it's incredible though like because there is this sense of the bigger the tam it almost i feel like the larger the market you almost have to have like more ignorance or more naivete going into it right because like it does seem like it's too simple you know like to mike to what mike's saying like t-shirts it's like that sounds too simple well there's there's the classic like oh if i can just take one percent of this market and it's like yeah you can't you get zero percent you know like i know the math seems to make sense.

7:11We had a dinner with all of our ownership group a couple of weeks ago. And I was like, guys, I need to say something. I always was like convinced this was going to work. And I thought it was a no brainer for you to join and for you to like give up your careers to come and do this. And it's really only been in like the last year to six months that I've realized like, oh man, this was incredibly risky. The chances were, you know, stacked way against us. And you all made huge sacrifices by being willing to do this thing. But like you were saying at the time, it was just like, oh, yeah, of course this is going to work.

7:48And maybe that's the little bit of insanity or craziness that you have to have as a founder. Not only was it going to work when I told Nick and Matt about it, they were like, I completely got them on board with the vision and the dream. Like they didn't think I was crazy at all. Well, what does that say? through everything. Like, is that just mean that they're crazier? Like, is it just like the blind following the blind? They're also gamblers. Like, they just, they saw that like. There we go. There's the degenerate gambler part. I mean, dude, we didn't have a lot to lose either. So what was the big deal?

8:19It was like, we were going to put a few thousand bucks into it. And if it doesn't work, then we'll just move on to another industry and try something else. Wasn't that big of a gamble. Ryan, did you know that you wanted to do this with like these people though? Like early on? No, not at the time. No. No, I kind of thought I was just going to do it by myself. And I went into it thinking it was just going to be me. But then when I was ready to do it, I'm just like, this is because I had been drop shipping stuff and I was already overwhelmed with that. And I'm like, this is just going to be drop shipping on steroids.

8:49I'm never going to be able to do this and run an agency. So that's when I started reaching out to people. That was the that's the thing, like what strikes me with your your background. That's again, why like when I look at you and Ben side by side, it's like you you actually couldn't be more opposite when you look at the history of the two of you like ryan you literally were like professional like poker player musician on paper you're like what am i gonna do with my life like you're that guy and then you got ben which is like assassin in career and is at meta and is in like probably one of the better places to be at meta and he's like nah this sounds fun i'm gonna go sling t-shirts on the internet so like you maybe you have that in common but when I look at no honestly though our skill set is very similar like Ben is more analytical and I'm more creative but like everything else we're very similar in we are jack of all trades guys we're dangerous enough in every single category of the company to where if we had to run it we could and we are very very similar in the way that we think about business the way we think about culture people um we're both incredibly fast movers in everything that we do we believe the speed is kind of the game, no matter what department we're talking about or initiative we're talking about.

10:05So even though our backgrounds are a little bit different, we are, we could not be more aligned on the fundamentals of business, what we care about, what moves the needle, what impact should look like, what the customer deserves, all of that good stuff. We are a thousand percent aligned. How did it take you guys a while to figure that out? Or did you know right from day one. You're like, oh, we are like we we work. Well, remember, we had already been working with each other like he was consulting with me early on for Facebook ads because I was running them and I was we are developing a friendship.

10:43And do the friendship. We realized we stopped even talking about meta ads. Eventually, we started talking about like an agency we would start together later. Or if like whatever happens with True Classic, we were like, let's crush it on a CRO agency or whatever. And we just realized how similar we were in that way. We both saw the value in the things that we were doing and what could be and how to drive value to customers or businesses. It was easy for us to get along because we had a lot of the same interests. This is fun because so far the episodes of Titans that we've done, we've not had like two business partners on.

11:19with the show. And we have a pretty interesting story if you want to unpack it. I do. I really want to hear this. Some more dirt there because it's a pretty interesting story there. I'd like you to go there because I do think it's actually worth telling Ben. Like you should Yes. Let's go there because I think how business partnerships form. Let me paint a picture for you if you're cool with that. I'll give you a little bit of context. So if you think about the world I was in at Meta, you get this interesting view because there is over three and a half billion users and there's over 200 million businesses, 10 million of which are advertisers.

11:50Because if you think about the business, right, you are in the business of businesses. And what we used to do is we used to look through this entire cohort, if you will, of companies and say, who have the highest potential, the highest ability to grow? Let's basically segment them. Let's invest in them resources, whether it's creative or measurement or solution engineering or product or whatnot, and then generate or manufacture our own TAM. And when you see that for over and over, for quite a few years, you get a sense of like what success could look like, who is really crushing it, who isn't, because it's all on the platform side.

12:25And then when Ryan reached out, I actually had the same exact reaction that you had. It was actually Ryan, it was Dink. And they were like, hey, we're just starting. And it was really early on, as in like Shopify was a few million dollars lifetime sales, super early on, super rough around the edges. just trying to figure stuff out and get traction. And think about it, it's 2019. And a buddy comes to you and said like, I am starting this t-shirt brand. I want to dominate in the t-shirt world. And you've seen a lot of people trying and you are naturally skeptical. Yeah, that can be a cool hobby.

12:59I don't know if that can be an insane business. That's cute. But let's see this through. And so really we just vibed on a personal level and that was the biggest thing. But then when we started doing it week after week, and we realized just like how insane the traction was, I have never seen anything like that. And to put this in perspective, we crossed$100 million in top line sales, profitably within two years, completely bootstrapped. And every single person is always asking, what is the X factor? What have you done? Have you reinvented the wheel? Have you launched some product that has never been seen before?

13:36Do you have this celebrity that backs the brand? Do you have some other unfair competitive advantage? And the answer is no. We just have grit. So it's all market. Is that what you're saying? It's just incredible market. Customer obsession, incredible product, incredible marketing. And we started really focused. Ryan's original vision, and we can go there too, was just to create the best T-shirt in the world in black and white. That's it. That was as classic as it gets. Because as simple as it sounds, really there was nobody in the market that really served the customers the way they wanted to be served.

14:08And we were thinking about the lens of how do we empower people to look and feel their best. We say, look good, feel good. Look good is all about the fit. We obsessed over fit more than any other clothing company, probably in the history of time. We just are never satisfied with it. And we asked so many guys, what is it for them? What does that mean to have that perfect fit? And we obsessed over that problem more than any other company. So we really coined that component. And then the feel, the fabrication is really soft. It's breathable. It's comfortable. You can wear it every day and love it.

14:38And then the price. if you create an amazing shirt for a really fair price, as in like half or less off than the equivalent, if you will, designer shirt or other premium shirt, you ultimately win. And then Ryan touched upon this lightly, but he's legitimately maybe the single or one of the most creative people I've ever seen in this world. And I don't mean to pep talk him, but he just breathed so much creativity into this industry and found ways to talk about shirts in ways that nobody's ever talked about before. and made shirts incredibly cool. And we created just so many incredible stories and ads and just became a thing and where everybody was really interested in the company.

15:19So you create a great product, you're doing great marketing and the scale was just unbelievable. You know, Ben, hearing you talk and Ryan, I'm curious your take on, you know what I want you guys to do, by the way? I want you to like call, if there's anything the other guy's like kind of full of shit on, just tell them that I'd love to get to that. So I will tell you guys, like I still to this day and Ryan, this might be a you thing. I still point people on your site. You had this like this guy, this side by side sort of video in like a gif of like the t-shirt comparison thing. I still show people that because I think it's so brilliantly simple and it just gives people like that.

16:01It's the this or that. and you guys are it's like that to me was just beautiful execution very creative thank you i mean it listen dude i'm sitting here every single day in this incredibly boring industry and it's easy to come up with great ideas when all you're thinking about is how do i give the customer the best visual possible to me it was kind of a no-brainer the side by side because I'm good at kind of reverse engineering what the customer would want to see. And then that allows you to create the kind of content they care about, not just the kind of content you want to show them. So if you're just reverse engineering that every single time, it leads you to the right answer.

16:47So the side-by-side to me was kind of a no-brainer. It wasn't the first time it's ever been done. People have been doing it with, you know, uh, slim fast and all sorts of things for years, but just no one really brought it into the apparel market because no one built an entire brand around one single fit. And that was highly intentional because I wanted to go so narrow that I didn't leave any room for anyone to pigeonhole us into being some broader gap type brand where they just did everything for everyone across every style and every pattern. I wanted to just stand for really one thing. And I actually, that's to what Ben was saying about the black and white thing.

17:25it was going to be even more narrow but nick kind of talked me out of that early on because he's like dude you're just you're gonna leave so much on the table not doing colors like like every season that comes up you're not gonna have anything to really promote and i was like okay yeah you're right about that i think it's super smart like by creating reducing the number of things that you could do it really forced you to focus on fit on how do we tell the story the materials, all of that. And one of the things it feels like entrepreneurs get tripped up by all the time is A, trying to do too much or B, trying to grow by just going wider and wider.

18:07Whereas you really saw a huge market and reduced the scope of things that you could focus on. And that helped you to go way deeper than anybody could have expected. Yeah, because there's so much nuance to going deep versus broad. Going wide just opens it up to too many possibilities. When you go deep on one thing, the ideas all are centrally into one bucket. And then you can just go so much deeper on that one bucket. So I always try to tell entrepreneurs and people that we're talking to, to stop trying to do too many things and find one thing that people care about and just build your whole business around that one thing, whatever it is.

18:46Here at Pila, AppLovin is the most incremental in the new channel we tested in 2025. It's self-serve as manager, Axon, is now open and they're offering you$5 ,000 in credits when you spend$5 ,000. Every single one of us is looking for that next best place to put our ad dollars. It is just one of the laws of DTC. There are now brands spending six figures a day on AppLovin. That kind of blows my mind, but it is true. And there are brands that are running it as their number two and number three channel after Meta and Google. That is super impressive. You would be foolish to at least not try it out in 2026.

19:19Go to nineoperators.com slash applovin to give it a shot. Oh, you'll also get access to the live operators mastermind we ran with over 25 e-commerce heavyweights, plus our step-by-step playbook to channel expansion, nineoperators.com slash applovin. Let's get back to the show. How long did it take you guys before you started to expand out, not just colors, but categories? Because I feel like we've talked about this. It didn't take that long. It probably took, I mean, once we saw the success of the t-shirt within the first couple months, I mean, Nick and I started developing tech packs for the polos and long sleeves probably within three or four months.

20:01And then those came to fruition, I want to say, six to seven months from the first launch in August 2019. And then we were off and running. We started developing like wildfire, but it was all going back to the top. We didn't want to do tops and bottoms or activewear or anything too early. We were just like, what are the obvious next tops that you can build off of the T-shirt? So you went from like, I only want to do a black and white T-shirt to, we're going to build a whole brand and we're going to be a multi-category pretty quickly. Yeah. I just wanted to do the T-shirt. I wanted it to fit right.

20:38I wanted it to feel right. I wanted the price to be palatable for a premium. And then everything was going to build through that DNA. So whether it was the long sleeve t-shirts or the polos, they were also going to have the same fit in the tighters and arms, and they were going to have the same feel and they were going to be super premium at an affordable price. And that, that DNA carries into everything that we do product expansion wise. Yeah. I mean, you, you actually like true classic and simple modern definitely share this characteristic of like, we're going to make a really great product and we're going to have a, like a, of like a value price point.

21:11That's like, it's just so mass market that it almost, I like to describe true classic. I'm like, I tell people all the time, like you sort of have to actively choose not to buy the product because it is such good value in what you get that like to buy something else, you're saying like, no, I just don't want that one for whatever the reason is, right? Cause it is like, it's a great product and you can't, you can't knock that. Like most of my male friends wear your t-shirts. I love that. We appreciate the support. And yeah, and the price point is super important to us because our purpose is a brand.

21:43And we coined it for every single person who comes aboard, anybody we interview, is to empower everyone to look good and feel good with the brand. And we really truly mean it. It's not this like, hey, let's just say the thing. So if we are priced too high, we're by definition not going to serve millions of people. In fact, we constantly are trying to figure out how we continue to be even more affordable and what that needs to look like as we increase the volume. Even if you think about stuff like that happened with tariffs and duties, we're incredibly sensitive of not increasing the prices to the consumer as much as we possibly can fight the fight everywhere else because we want them to feel the way you just did and say, whoa, this is a real steal.

22:23I know what it costs to buy a quality shirt. You also just talk, I mean, you speak to a much broader, you know, TAM, the lower you get. So that's something I'm constantly struggling with, which is like, how do we get to Hanes price point, but still retain all the quality and consistency? And it's just near impossible to get there unless you own the manufacturing. And, you know, we're six years in, so we're a ways away. You know, Haynes has literally 60 years under their belt of making shirts before they got their own manufacturing. So eventually I think we can get there. But the unit economics just do not net out today for us to get anywhere near the price points they're at.

23:07One of the things that I think is awesome, guys, is what you're saying is we want to drive more value to the customer. And we want to win because we're helping more people to win and we're making it more accessible. And really, if there's a critique I have of e-commerce, D2C in particular, man, it feels like so much of the dialogue is how do we charge more? How do we get margins higher so we can pay meta a higher tax to go and get customers? And when you read the stories of great entrepreneurs, especially in consumer, especially in retail, a consumer facing retail, like it's this obsession with driving more value to the customer.

23:48and that's what I see with your product. And one of the things that I think is really clever, I mean, this is probably where simple, modern and true classic diverge is that you're able to do it through bundling because you sell a product that people can use five, six, seven of, then your per shirt value is amazing. Like I literally just went on there and got some more. It's a$16 per shirt cost, but you're able to sell six at a time And so because you're able to diffuse that shipping cost across several, you're able to make the economics work and favorable. And I think it's really admirable. I also think this is why so much of the e-com, especially D2C industry, is so fragile because they're not focused on these things.

24:37It's just like, no, you've got to get your gross margins to 70 % or you have no chance. And it's like, if you're at 70 % gross margins, you're not going to have any chance of hitting a wide swath of customers, which is, I feel like, what you were just saying. You know, let me ask you a question. What's the largest consumer brand in America? Largest consumer brand in America? Like individual brand? We're talking consumable or durable? Consumable. Or durable, it doesn't matter. But just like a brand that you're like, okay, how are they doing the highest volume? I mean, I don't know. I'm going to guess it's somebody like Coca-Cola or something.

25:09You know, it's like one of the... Yeah, I mean, yeah. I guess like where I'm going with this is it's Kirkland's signature. Yeah. Yeah. Think about Nike. Yeah. Think about Nike. They're doing like. A durable brand. Yeah. They're doing$84 billion. And then let's unpack this for a second. Okay. What does it mean? How does Kirkland do$84 billion worth of product? Yes. True. But, but think about it for a second. I would argue it's two things. It's quality and price. Oh yeah. They sell you really good quality products for a really good price. And they earn the trust of millions and millions and millions of people.

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25:43They're really good at curating. And they don't even make their own thing. But arguably, that's what all consumers care about. And when they buy a brand, what do they buy it for? Easy notice, we don't even put our logos on our stuff. They don't care to wear our logo. They care for the product to be really good. And they care to pay a fair price for that. And that's all we're trying to optimize for. So if you really reverse engineer back to Ryan's point, and you're truly obsessed with customers and actually understand what it is that they actually value and you build a whole brand around that, you are going to win because you are here to serve them.

26:16And you're not in your own head on where it should be priced, what should be the gross margin. They could give two s*** about our gross margins. They don't even know what it is. Yeah, the customer doesn't care. Yeah, they don't care. They don't care about goals. They don't care about our metrics. Similar to Kirkland, we are rolling out with chocolate-covered almonds next year. Our own line of soap and dishware is going to be fantastic. Well, you know what? I bet if you did it with great quality and affordable prices, you could sell. I mean, like, I think that idea that you just said, it's so simple.

26:49And yet people miss it all the time that every single person, almost every single person who makes purchasing decisions, they have a Venn diagram of a few circles and they're trying to optimize for those few circles. And in almost every single person in the world, one of those circles is lower price and one of those circles is high quality. Like now there might be a third one, which is like, you know, what it signals to other people socially or I want to be on trend. I want to have a lot of color choices or want it to be good for the environment. Like, you know, Matt, you've looked at that with some of your brands.

27:24But the quality and price ones, I think those two circles exist in everybody's Venn diagram of purchasing. yeah it's uh true classic to me i've done so many things that have fascinated me about you guys over the years it is the probably chief amongst them is like relentless in execution like you guys are just execution monsters you talk speed but i think your focus on the basics and then just like this discipline to stay focused on the basics and really like ben every time i talk to you you literally hit the same points over and over again. And I'm like, because they're right. You know, like there, there is nothing fancier.

28:04Like there's no better answer than the things you're talking about right now. What I want to know though, is like, you clearly, you guys started off this way, but was there a moment where, uh, when you guys were working together early on, where you were, where you were very high conviction that this was going to work? Like, Like, Ryan, there is a sense of like ignorance that we all have as entrepreneurs. Like when we go into something, we're just like optimists, right? We're ignorant optimists. This is going to work. But there's got to be a moment where you two are looking at each other like, holy crap.

28:35No, no, we got this. Like, this is a real thing. I hate to say it, but I honestly thought it was going to work or I wouldn't have started it. Like, I really did. Now, listen, I didn't think it would get to this level, but I have an incredible amount of conviction early on. and then you know i think with ben we were on the journey you know early on together he got to kind of watch from the meta seat and get more and more interested over time watching this thing scale and every time we got into a meeting he was even more in disbelief than the previous week like what is happening over there like we'd be on calls he'd be he'd be giving me some feedback i'd be implementing the feedback in real time and by the end of the call he'd be like okay i'm going to send you the notes i'd be like oh it's already done and he'd be like what's already done the work we just talked about is done remember those moments where i mean do i remember clicking for him he's like oh this is the different thing you guys are doing you're operating so quick it's a little scary can we talk about speed for a second yes absolutely we all just agree that speed is one if not the single most important one hundred percent important things in business and i like i like the distinction between speed and velocity, that it is speed plus the right direction.

29:52You know, and I think that like, but obviously early on you're pivoting around so you don't even know what the right direction is. And maybe it is just pure speed, but like, absolutely. Like even what you just said, how many of your clients applied learnings as quickly? I mean, nobody. And that's the whole thing. One thing that Ryan and I have a crazy common ground around is we lack any sense of patience. We want things done like yesterday. Like we just talked about it and we look at each other. How did we just talk about this right now? What do you mean it's not already done? Like we should have done this like last week, last month, last year.

30:25That is just how we roll. And it's intense. But I would argue that this is one of the things you ask me for. Always people ask about secret sauce and what you guys do. One of them is simply how we move. And by that, I mean really, really fast. As in like faster than anything you've ever seen. And Matt, if you remember our last call about, not call. It was a dinner in L.A. and we talked about like road shows. Dude, your speed was hilarious. And Costco and everything. Like we have like hundreds of them in the rear view mirror just because we are like this is good. Like we're just all in and they don't care.

30:59Our teams, when we first proposed to them that we were going to do a certain amount of number of road shows per month, they looked at us like we were absolutely insane. I thought you were nuts. And we looked at each other. Which you were. Which we were. but like we pushed through and figured it out and now it's all running very smoothly like it's only insane until you do it and then you look back and you're like wow i was the roadblock actually in my ability to think that we couldn't do it but we the whole time ben and i were convinced we could get to these crazy numbers even despite talking to you from that dinner i remember going back and we even like looked at each other like could you believe what he's how many he said like he thinks we're insane are we insane like we were like really i thought you were legit nuts.

31:42But we just bulldozed through. Yeah. We just did it. You know, you know, I mean, Elon famously, I think, has that gene as well. Like and and it's it's kind of like you have to find your fingerprint as an entrepreneur of, OK, I'm going to really over index on these things. And I know sometimes that I'm going to go too far and I need to do it in a way where it's nonfatal when I go too far. But you would much rather be the person that's like, I'm going to push a little too hard. I'm going to try and go a little bit too fast. Then I'm going to have a little bit too much urgency. I'm going to have a little bit bigger eyes than my stomach sometimes than the opposite.

32:19Almost everything is non-fatal though in business. I would say the only things that are, so you can really just go at warp speed and fail forward on just about everything. The only thing you can't do that with is the inventory component where you're just like, I want to expand into 50 new categories and I want it in a few months. And I just want to, you know, invest a million dollars into it and see what happens. Like that part, you got to chill out on because that is how you put the business into a crazy cash crunch. Yeah. You should really underline that point that like when it comes to managerial decisions, strategic decisions, all of that, you should be as bold and as fast as you possibly can.

32:58The place where you have to be careful is financially because that is the one place where being overly aggressive debt. You can absolutely blow yourself up. I mean, there's a reason why a lot, most of entrepreneurs, I think, go through a bankruptcy. I'm fortunate. I haven't been through one, but that's exactly how they get there is that they take that same level of aggression and they just go risk on across every decision. And so part of being able to do that well is being able to say, hey, I'm going to be full bore in everything except for these two or three areas. Yes. Because those can burn the house down.

33:31Anything with finance and cash involved has to be taken with. And look, we're not professionals in that realm either. We really rely on our finance team to be there to kind of say, listen, guys, slow down a little bit. I know you want to go because we'll get into a category. And my immediate thought is always, well, it's so much better to overbuy because we'll then we'll never run out. If we underbuy and leave all that demand on the table, it's going to absolutely kill me. And I will be thinking in And in product, you can't just develop it overnight. It takes three months sometimes. So we constantly get pushback from our site merchandising team who's like, are you sure you want to bet this big on this brand new category that you have unproven?

34:14And so they do rein us back a little bit for good reason. But I would say that what happens typically, and I think why we tend to run a little bit differently than most, is simply around this. People talk about the risk tolerance. But the idea when someone says there is risk, which there is a risk in everything, The natural tendency for most is to not take it. It doesn't sound like something you should do, right? Risk is something you should kind of mitigate, avoid, overcome, something else. And then what I like to do, and Ryan is very naturally just, I mean, we talked about the gambling part.

34:45He can tolerate any levels of risk better than anybody I've ever seen. Yes, thank you for saying it. But what I would say is that I try to unpack this, and I try to unpack it in two ways. One, what is the actual risk, as in like what is the worst case scenario? If everything went to shit, what is it? Let's quantify it. Let's talk about it. And two, how likely is that to actually occur? And what happens for us in the vast, vast majority of cases is that the worst case scenario is not that bad. And we know that we have the ability to figure things out in like 99 out of 100 cases and avoid the worst case scenario.

35:21In which case we go and say like, well, great. Let's just assert ourselves into things, knowing and believing in our ability to figure it out. And that's literally it. This is what's great about having a value-oriented approach and having product quality be a real focus. It is very difficult to get into inventory that you can't get out of when you're willing to be flexible on price and pass value to the customer and it's really high quality. Yeah. That where you get in trouble, and luxury brands will get into this, where it's like, well, we can't sell this for that price. And it's like, well, you got seven years of supply, so what's the other option?

36:00And that's how you get really crazy behavior, like people burying things in landfills or sitting on inventory for excessive periods of time. Because of the structure of your company and kind of the values that you've built it around, I actually think that helps you to mitigate even things like inventory more effectively than some companies. Yeah, I think so too. And we're not really apparel in that way. We're not fast fashion. We're not chasing trends. We're not going after crazy patterns or colors that may or may not go out of season or out of style. We're true classic. The idea here is that if you were to take this t-shirt out of your closet or wardrobe 10 years from now, it works just as fine as it is right now.

36:38And when you go after premium essentials, you mitigate a lot of that risk because people need t-shirts and they need sweatpants and they need underwear and they need socks. I mean, they just do. So if you do a great job at that and you do it for a good price. Worst thing is it's going to take you longer to sell. Okay, so let's talk about some financing solutions of how you float that. But you're not going to burn it. You're not going to bury it. It's good stuff. It just might be slower than we thought. Yeah, Mike, the dinner in LA they're referencing with the Costco thing. You guys went back and you were talking about me.

37:09I went back after that and I'm like, okay, they're clearly, these guys are at just like a different speed level than I am. But what I started to do, Ben, was I started to write down, I'm like, what are all the reasons that they could go faster? Like what allows them to go faster than we could? Like the mechanics of your business, right? Like Mike hit on one, like you have a different margin profile. Your supply chain is a little different. Like I'm doing hardware and firmware and software. Like it's just a, it's a slightly different beast that allows you guys to just move at a speed. And then you clearly have a risk, a risk calculation, like mental model or framework for your business that you like just quickly move through.

37:46And I think that's listening to you guys talk. It's like that is clearly a superpower for the brand risk tolerance component is is one that I was lucky enough to build. And I was lucky enough to have partners that also had incredibly high risk tolerance. And they didn't hold me back. And I and we were all on board with that. I would say Nick was probably out of the three founders. Nick was the most conservative. but we took wild bets early on. And if it wasn't for Matt being my co-founder, I just can't see anybody I know in our circle that comes even close to my level of risk tolerance. And putting two people like that together in business is either the worst idea in the world or in this case, the best.

38:32Yeah, it worked. It was insane, the kind of bets we were taking early on. I mean, we just believed in ourselves so wholeheartedly. Can I ask one of you guys? You guys amp each other up. Like one thing that's really clear to me, I've got it with some of the guys on my ownership team. Matt, you've mentioned your partner. I think Sean and Connor have that dynamic that there is something about having a partner that kind of is part of your own personal flywheel. Like they kind of amp you up and then you kind of give that energy back. And it reminds me of Paul Graham wrote an essay about ambitious people.

39:09But here's the key part that he said that I thought was so good. He said, ambitious people are rare. So if everyone is mixed together randomly as they tend to be early in people's lives, then the ambitious ones won't have many ambitious peers. When you take people like this, you put them together with other ambitious people, they bloom like dying plants give them water. Probably most ambitious people are starved for the sort of encouragement they get from ambitious peers, whatever their age. And I think like even just being on this pod, it's like, yes, Let's freaking go. Right. Like just even being around you guys, it's contagious.

39:43Oh, yeah. Being around other people that are like, let's freaking go. Let's get after it. Let's set ambitious goals. So I love that about you guys dynamic. But I think that this is also the reason why the Internet is so powerful is that each of us has so much like I live in the middle of Oklahoma. Right. Like each of us has so much more access to other ambitious people and their perspectives than we did 50 years ago. And that that helps to amp us up and help us become the version of ourself we want to become. Yeah. Oh, I love what you're saying. And I'm going to use a diamond analogy, not because of my last name, but because the only way you polish a diamond is with another diamond.

40:28And it's through the friction and it's through the arguing and it's through the fighting, but for the greater good. What Ryan and I ultimately care about is one thing and one thing only, which is getting it right. We don't really care about being right. We don't care to be wrong. We don't care about egos. We don't care about whose idea was that. The number one value, true classic, move the needle. Your outcome with results. Oh, absolutely. Call me an idiot on any other call. I don't care. That's fine. Prove me wrong. The opposite. I'll thank you for that. I just learned something new. But that is the only way for us.

41:00And so, yes, to your point, you need to find the diamonds who are ambitious, who have what it takes from a DNA standpoint to succeed. But then we wrap each other. Like I've learned so much about creativity and out of the box thinking from this guy more than like most just through osmosis and being next to him. Like he just inspired me. It's like Sora 2. I spent like three hours last night prompting videos and Sora because these guys are already like. I literally. He cannot go to sleep because of what he can do. Literally have created, I want to say around 90 assets from Sora 2 already. I am obsessed.

41:33Yeah. And if people aren't in there figuring out how unbelievable this is, they need to hurry up and get it together because everyone is suddenly becoming Steven Spielberg overnight. It's version one, but you can see where this is going and it is just mind blowing. Right. Like you can totally imagine like with the personas that, OK, I add an influencer to my brand and they give me the ability to now generate Sora videos with their avatar or whatever. and then I just need to check with their people before I go live with it. It's so much bigger than UGC. Yeah. I think what is unbelievable about it is that you can now produce studio quality scenarios.

42:13Like I can put Alex Trebek on a video for no money and the whole backdrop can literally be the studio that would cost hundreds of thousands of dollars to rent for a single day shoot. I can do it instantaneously in literally less than a minute with a prompt and I can even tell him to talk about True Classic and it just all does it all for you instantaneously. I mean, that has never existed. So forget, I'm over the UGC. I only care about doing high production, amazing comedy at scale with the snap of a finger. And it's going to be unbelievable. We're thinking about that with our brand videos. We worked with Jock and Raindrop to make a very good brand video.

42:54And in some of the testing, got really good performance with it when we went top of funnel, but it's like, you know what we need? We need 5 ,000 great brand videos, right? And that was like literally an impossible idea, but that doesn't sound impossible anymore. Like you're saying, I mean, you're going to want to go the comedy angle. We might want to go a different angle, but now all of a sudden, or you can do like another thing that's incredibly exciting for us is that we have all these different verticals like licensing. And it's like, I can spin up what would have been a$200 ,000 video that's contextualized to the University of Tennessee and I can do it in 30 seconds.

43:30And then I can do it for every other college before the half hour is up. And it's like, boom, stuff that was like completely off limits is now on the table. It's accessible and I can create it. I can iterate on it. There's just no excuses. There's no excuses anymore, dude. I came in here, guns blazing. And then Ben immediately wanted to know how and how did you do it? And now he's like completely hooked. We're up all night just sharing ideas. Because what I would say that I have learned from it already is that you have to kind of start in ChadGPT. You have to build some concepts, build some scripts, start flushing things out before you go to Sora.

44:08Because what you'll inevitably do on Sora is you'll have to create 15 iterations before you get to one great one. right so you kind of learn the hard way that you have to set it up correctly on the prompting side before you go in there to deploy it into a a system like sora that allows you to get the output you're honestly looking for so it does take a little bit of know-how and prep work and even chat gpt you have to kind of flush it out a little bit you can't take the first script you might end up taking the 27th script that they give you because you just have to keep getting the most out of it and finding the gold nuggets because it's not great at scripting i will say chad gbt it it takes a bit of nuance and i still end up having to put a bit of my own flavor into it to make it funny because it's just super corny i use i use when you ask it to be funny i use claude for the scripting ryan um it from a writing and copy and scripting i actually find it's better you're 100 right if you think of like creativity and creative output uh like and you took take that and you just apply it to like film or something that takes like a lot of production you could actually shrink the whole process if somebody creative could just describe in detail what they actually want and creative people typically have they've historically not they don't do that they just do the work right like a director or somebody can sit down and just like they can piece it together but they could never they would never take the time to like write it out this is exactly what i want here's how i want the lighting and the shot and the transitions and and like all that stuff.

45:40I want you to breathe on this cue. And all that is what you're talking about. And that is actually now the work is like, I really do think we're in this idea economy. And I, and I, the thing that comes up for me though, with a company like yours is, what is the thing then that holds you back? Right? Like you guys are just like balls of energy and you have this massive market and you have vision for it. There's gotta be something that is like the limiter on you. That you're like - for us on a daily basis is just like, how many fires do we have to put out today before we can get to the good stuff and the fun stuff and the stuff that we're best at?

46:16Because the stuff that we're best at does not occupy our time traditionally and unfortunately. And I wish it did. But the reality is, is you got to put the business ahead of absolutely everything and the people as well. If the people have problems, they become your problems and you have to go to bat and you have to figure that out and you have to do it in the best possible way that's amicable for everybody. and that takes a lot of time and energy and it's a huge suck, but it just is necessary for the greater good. And so we don't get to do all the fun stuff every day. Like we never get to do this kind of stuff, right?

46:48Like I wish we could just come in here and riff with like-minded entrepreneurs. This would be amazing. Yeah, and think of what comes out of it too. Yeah, but after this, we're gonna have to go back to work. Like we're gonna have to literally just sit down and put our heads down and start fighting fires again. That's another thing that's really important. And I think it's a really important point for what success looks like, any entrepreneur or operator that think that they can operate somewhere here and everybody do their parts and everything will fall in place is completely delusional. You need to be able to operate at all levels.

47:18And by that, I mean, do every single person's job probably better than they can. And if not, you're going to miss stuff and you're going to miss really important stuff, some stuff that can flip you upside down. And so a lot of what we do in the day-to-day is not just lead by inspiring, empowering people to think big and be bold and take risks and help them think through stuff maybe in a better way, but actually doing the work. That's how we spend time doing the actual videos because we try to lead by example. And hopefully then you find a few creators that can take that and move on. Same goes with any other part you sit in the company, whether you want to do roadshows, you want to do Amazon, you want to go international, you want to launch women and kids, which we're doing next.

47:59There's always net new stuff. And so I would say that the other two values I told you about moving the needle, one of them is crush the challenge. I like to use challenges versus problem because problems, issues are things that people don't want to have. But a challenge is something you want to rise up to. So trying to view those as challenges that you want to crush. And as you get better, if you think about it, someone mentioned Elon, I think, earlier. Elon is the single best challenge crusher in the world. He crashes challenges that people thought were impossible because he's at that level. Whereas my daughter might learn how to tie her shoes or try and be a$2 challenge.

48:36And then on the build leverage component, and you mentioned what are we constrained by, it's always come back to leverage in my view. How much leverage can you actually produce? And it doesn't have to be just with the internal people. It can be external partners. It can be technology. It can be AI. It can be content. It can be lots of different things. But ultimately, you need your time back so you can keep multiplying and compound the impact. And so in areas where we don't have good leverage or we have negative leverage, it actually constrains us from being able to push further and grow faster.

49:12But then we go in there, cross some challenges, rebuild the leverage, be able to pull back out and go think bigger, like bolder, et cetera. Another component, just going back really quickly, I wanted to touch on this because this isn't like a sexy thing, but I just want to like give everybody the dirt. You know, Ben and I don't agree on everything, but what we do agree on is that when we go to battle on something, what we ultimately want is the truth and we are truth seekers and we don't let our egos get in the way of what we think or what we want to be right. And if, oh, I happen to be wrong and this is going to make me look so bad, we don't give two about that, which allows us to get to the solution insanely fast.

49:57We'll just like fight about something. It'll take seven minutes and then we'll like both agree that it was the right answer either side. And then we'll instantaneously move on to the next thing and never think about it again. And no one cares. And it's on to the next. And what else can we get to? But what I traditionally see with a lot of other leaders has been that they take it very personal when their idea doesn't get pushed through or you disagree with their idea or their stance and they will fight to the death because they see it as a defeat and they see it as a weakness from them. But actually, I see it as an incredible sign of intelligence and strength when you can admit, I see what you're saying there.

50:37That actually makes a lot of sense. And the quicker that you get to that confirmation, the better you are. Right. Like we can I can be so convinced of an idea. And I will almost instantaneously within less than five seconds, be able to pivot. If I see what they're trying to get to, and that it actually makes a lot of sense. We have to do this a lot in CRO where we're riffing about a page and we're going, let's move this and let's take this down. And I don't like this because it clutters up the page too much. And then someone will go, yeah, but we need that because of this. And then I'll just be like, yeah, you're right.

51:08Let's just do it that way. Like it has to happen literally that fast, or you will slow down the execution to a screeching halt while you battle out why you think you're right and why you think you're wrong. And it just eats up so much energy that, you know, I think people need to find ways to constructively argue and just be so objective about what they're saying and leave it there. It doesn't matter if I'm right or wrong. Just let's get to the truth and move on. That's cultural though, Ryan, like the, the, we don't care about who's right. We care about what's right. That is so cultural in an organization.

51:40Like we're very similar. It's another value for us, by the way, seek the truth is a value. Yeah. And it has to be though, like what you're describing, it needs to be that core to the company. Like when people come in, they, they, it's not something you could just explain to somebody. They kind of need to see it in action every day and feel it. And it starts from you guys, right? Like all the partners in the business have to tell you where in our CRO testing, that group is so tight knit now that we have developed such an unbelievable flow state of brainstorming slash crushing your ideas at the same time, like where one person will be speaking with so much conviction and you literally just go completely the opposite way against what they're saying.

52:23And literally in real time, they can see it processing and they can start to see it and they start shaking their head and you see them overcoming all their ego almost in that one second. And we have gotten there on CRO specifically because you have to be in this brainstorming slash innovation mindset the whole time. And it is magical, the team that we have there now. It's so different than how it was in the earlier days where we have to explain things and here's why and here's what I think. And like, we're done with that. Now we just know how we roll. And we move so fast and innovate so quickly because of it.

52:57Has there been a moment in the business? Like if you look at the last several years, like let's think like, let me know this in. Has there been a screw up, like a near fatal, like, holy moment in the business where like this idea of move fast, challenge all ideas, like where you're really having to stress test this? Like the we don't care who's right. We just care about what's right. Has there been like one where there's like tens of millions of dollars? Yeah, it's always the inventory thing, dude. I mean, there's just every consumer brand. bigger yeah because there's nothing bigger and more cash intensive than over betting on inventory and if you know anything about how we roll we are betters and we are over betters because we always bet on the upside we believe in ourself and to ben's point what he said earlier is like if you over bet you better damn well know how to get out of that quickly and find a way and we just have so many ways of figuring that out.

53:59As they're in that, I mean, it's always inventory. Every good consumer operator will tell you, like mine, I've told Mike this, like my near-death experiences are always inventory. Like always like, oh, yep, that's way too much of that. Or lots of something and it's broken. I've got that one too. Was there a stage of like, when you look at the growth from 2019 to now, because it's been pretty meteoric. Was there a stage of growth that you found particularly challenging for everybody? Was there one? Yeah. I would probably say that it started getting a lot harder when we scaled people, because people take so much time to train and hire and learn.

54:43And you throw them into a business like this, and it's very chaotic. And a lot of them just don't know what to make of the chaos and they sink or swim type vibe. And so you waste all this time hiring people that you think are going to be great. And then within a couple of weeks, you're just like this, just they're not of this cloth. Like they're just going to have to go back to corporate world and hide there and make your moves years ahead of time like they do and not fly by the seat of their pants. So I would say when we started scaling from 20 to 50 people, it was a lot to handle. And we've gotten much better at it over the years on the hiring front.

55:25We've learned what works here and what doesn't DNA wise. So we really look for entrepreneurs, people that can multitask, people that are scrappy, people that have great attitudes, people that want to learn, people that are curious. Basically, all the values we coined are the things we care about, you know? And I would say in a nutshell, Matt, if you think about the brand, we started super focused. And I spoke about it earlier. Jazz at T-shirt, Jazz in the United States, Jazz on the Shopify website. Like literally textbook kind of focused proposition. And there came a time where we decided, you know what?

56:02It's time to expand. And we coined, I think there's four main levers. we prioritized the first three. Product, market, channel, M &A. We did prioritize M &A. Just did product, country, by market, I mean country, and then channel. And we were like, okay, we dropped the T's, we moved to true classic. We really expanded the assortment for him. Active wear, jeans, underwear, socks, jackets, etc. With the belief that if we are here to empower them to look good and feel good, and we did such a phenomenal job with a t-shirt, there is more we can offer for him to truly own the wardrobe, if you will. On the country side, we literally turned it on and made ourselves available in 190 countries worldwide.

56:42And then on the channel side, we moved truly omnichannel. We build our own retail locations. We're doing marketplaces on Amazon and others.coms, TikTok shop, Instagram shop, et cetera. We do wholesale, Costco, Target, others. And really what becomes super challenging, and I would say I'm still struggling with this on a daily basis, is how do we keep growing, but at the same time, bus complexity that raises its head at any given day, just non-stop. And this constant push between signal and noise. And how do you prioritize that? Because you need to test and learn and try and do other things to find more opportunities.

57:21But at the same time, complexity is so detrimental to the business. People think that simple is easy because it sounds simple, but simple is the hardest thing ever. By the time you got it to a super simple state, you've gone through a whole host of pain and truth seeking and trials and errors and you name it. And now you truly figured out what it is that the customer cares about and you can go back to simplicity. So what we've gone through is a lot of like, let's touch a bunch of things and then go back to the court and then go back to expansion and then back to simple. And it's with everything.

57:56It's with the products, It's with the offers. It's with the website. I mean, if you put our website through the time machine, you saw it on every single day, dude. The amount of change is just like, it's like mind-blowing because we're so relentless about, but what if? And what about this? And what about that? And it's just an area we just obsess over so much, but it's not the only thing. And then what you go back to is if you're like, you know, if you're thinking about any big CEO who's like turning around companies, what they typically do is they go into a company and say, that this is a complete chaos and I'm just going to cut the long tail.

58:29I'm going to cut the long tail of products that don't matter. I'm going to cut the long tail of countries that don't matter. I'm going to cut the long tail of customers that are like, you know, poor LTV. I'm just going to cut and cut and cut. And then they create this clarity and simplicity to regain traction and get the business back on track. And you don't have to go through a bankruptcy to do that. You just have to constantly play this offense and not defense, but clean up in a very regular cadence to keep the trend on track. But you have to stress how hard that is though, Ben, because it's so difficult to do that.

59:05Because number one, I mean, I think entrepreneurs are really good at exploration. Like that is quite literally your DNA is like, hey, that looks fun. I'm going to go over there. So there's like a discipline that then has to be built. And then really it's courage. Like that ability to go back and cut anything, right? like a channel, a market, a product, even people. You know, it's like, hey, we've, every time you add any of these things, products, markets, channels, people to your organization, you increase complexity just by adding them. Even if you don't think you are, that is like brain damage that you're adding to your company.

59:41So there's just an incredible amount of courage to have that like, we're going to advance and I'm willing to like look back and trim as I go. It is so counterintuitive. Like, I love that you brought that up. I think not enough founders, operators, whatever, understand that that is just as important of a job. It is so important. People also think that cutting means less revenue. when in actuality, simplicity and focus and getting a narrow assortment increases CVR because you are forcing them to less decisions for the customer. We did this test the other day with denim where we have authentic denim and we have comfort denim.

1:00:23Comfort's like the stretchy softy version. That was the original OG. And then someone came into the business and was like, oh, we need more structure. We need a Levi's competitor. Let's do authentic. And we're like, fine, let's do it. It generated a little bit of money. But with tests we ran recently, I was convinced, like Ben and I were both convinced that like, if you just remove it, it's, it's not going to matter at all. And actually that money won't just go to zero. It'll shift all the way to comfort. Right. And so we ran this test where let's just remove authentic from the denim and let's see where the money flows.

1:00:50Sure enough, lo and behold, it made no impact and all the money just flowed to the next option. So again, you know, eliminating that skew for us was almost like 700 grand a year in savings straight to the bottom line, not to mention the complexity and the shipping and the inseams and all the chaos that comes along with denim. But dude, we are now in this state of like, well, what else are we missing? If that was so easily achievable, we need to rethink site merchandising in general and what that means to the overall business. And while it might sound small, for those of you who not in apparel, just think about it for a second.

1:01:27You have a fabrication. Then you have a wash or a color, depends on what you do. Then you have the waist sizes. Then you have the instins. And when you start adding that up, killing one fabric, let's just say you have two, it can translate to like hundreds, sometimes thousands of SKUs. Because you have like 45 waist instin combinations, five washes, this, like you add it up, you multiply it. It's crazy. And that's like one. And then you go back and it's like, whoa, not only did that help, it actually hurt the business. If you think about the, you know, cheesecake factory menu versus in and out, or you go to Sugarfish and you go, just trust me.

1:02:03And that's it. People love that. People are so tired of making decisions. They want a recommendation. They want simplicity in their lives. Our guys, they're simple. They don't even know what they want. They just want us to tell them what they want and make it really simple and easy on them to get what they need. And so it's interesting, but that's a product example. It's not the only example. But you could do this with your own business. I would say that like an actionable takeaway right now is to look at your 80-20, look at what drives most of the business, kill off everything else product-wise, and then go so much deeper on what's already working and expand things in that ecosystem.

1:02:40Not just going left or right across different verticals and going, well, this guy does this, so I should do it. It's like you've already proven out that something works. Why don't you just keep going deeper on what works so that you can make your decisions so much easier? Going deeper instead of wider is a really good piece of advice. And I think another way that we've thought about it internally is just what is the return on complexity? Complexity is really hard to measure, but it has a million costs that are hidden. And so the off-income statement costs of things are harder to measure. And so therefore organizations are usually worse at optimizing for them.

1:03:22And there are what we have found in our businesses. There's a lot of things where it looks like, yeah, you generated a couple hundred thousand dollars worth of gross profit with, you know, a ton of organizational complexity to do it. It just doesn't make any sense. And that organizational complexity, what you're not able to see is the opportunity cost. If you weren't taking on that complexity, what else could you be doing? How much better could you be doing in your core lines? And so I think this is actually one of the places where it's the hardest to lead people because you really have to be deliberate at finding how you've had complexity creep and allowed complexity creep in your organization.

1:04:05And it's very hard for people that aren't in an owner mentality to understand why you would ever say, well, it's like, well, this thing makes money. Why would we, you know, why would we cut this thing? People, I got some customer support emails that said they really loved it or that, you know, it's producing gross profit and you have to really help them understand. Yeah, but what's the cost of that internally? Like, what are all. You have to scale it or kill it, in my opinion. Like if you've given it a fair shake on the creative side and the marketing side and the email side and you've done all your work there, you have to really just look back and go, did it scale?

1:04:40Because if it's a winning product, in theory, you should scale with the right creative. So if it didn't, what's the real reason? It just might not be the right product market fit. And it might not be that we think it's our creative or that we're not doing something right. It actually is just the product. I think that's hard for people to see. If I'm looking back at the products that have scaled, still to this day, they are a huge percentage of the business, like denim, activewear, like all the things that we know are great. And that's why those will live on and will never kill those things. But in my opinion, if you can't scale it on paid media or Facebook in this day and age, it's the same thing with like people that drop ship.

1:05:16What they know is that if it doesn't get traction early on, they kill it and they move to the next thing. And they go to the next thing until they find a winner. and then they ride that winner till the cows come home, right? And they keep coming up with new creative around it. But yeah, and the point to that is like, you're absolutely right about the measurement, but I call this the complexity tax. It's not something that we have a tax return on and see the percent we're paying, but it's absolutely there. But that's a good example of like an easy win because you can measure and prove to people that not only does it not help the business, it hurts the business.

1:05:50And therefore, why would we take that on? So to your point, it shows gross profit, but is that incremental or does that cannibalize the next color, the next wash, the next fabric? And once you prove it to them, then everybody's like, aha, that makes a lot of sense. And then you kind of put everybody at bay. And the other thing I would say, Mike, which is really, I don't know, I would argue I'm probably one of the most rational people in this world. I literally don't make any decisions based on feelings. I just want to get it right. And I don't care. and if people are very emotionally attached because it's their baby and it's their product and it's their idea and it's their fill in the blank it makes it very hard to untangle because they have feelings about it whereas and that's one thing I absolutely love about Ryan even though he's the creative he's not attached even though he created a lot of the products and a lot of the ads a lot of kill my baby he's not attached though which is really cool last thing I would say is that it always comes back to problem solving.

1:06:52If you cannot articulate well enough how you made something better, faster, cheaper for the consumer, so they should care about it, it's going to always be harder to actually gain the product market fit. And the products that we see we have an easier time letting go of is frankly, where the value proposition might not be as strong as the other one. What made the comfort so popular is that it gives you the great look, but it's comfortable. It's stretchy. You can literally like go to the gym in it. I'm not even kidding. It's that level of comfort but it looks like a great structured pair of denim whereas the other one might not have enough juice in it to carry its weight.

1:07:32Can I ask you guys then like this idea of cutting as you've built the business up and you've like you get rid of products, right? Have you guys been like a sort of straight shot growth every year like from a revenue milestones or have you actually had to like advance, retreat, advance some more like the typical Everest up and down? Could you maybe even give like everybody listening like the revenue milestones that you've hit like 2019 through to today? We have grown every single year on top line revenue, but it wasn't to say that every single category, every single channel, every single country has been up and to the right.

1:08:09The focus has shifted, but as a company, we have grown every single year. I mean, rough milestones without, I don't even know if I remember the exact number, but last year we did over 200. Year one, we did, what was it, 15. Year two, I think it was when we crossed the 100, like 90 or something along those lines. So it's been pretty consistent. And this year we're hoping to get closer to three. This is a big growth year for us. Just really because of wholesale and not just wholesale, but also cutting a lot of things and getting back to creating winners around the t-shirt. Like we're rolling out, you know, we rolled out the curved hem.

1:08:49We rolled out the Pima. We rolled out the heavyweight tee. And it all goes back to like, what was our winner, guys? If the t-shirt is 80 % of the business, why are we creating flannel shirts? Get rid of the flannel shirts. Go back to the t-shirt and create iterations of the winning hero product, the end. And that we just know we can buy into and feel super confident that we're not going to have a bunch of inventory sitting on the books for the next 18 years. Yeah, and equally important, Matt, because I know everybody likes to size up companies based on their revenue figures, and I think it's an okay focus, but it's truly not the main conversation, right?

1:09:25We've done that profitably. And first of all, we have always had to do it. We did not raise money to begin with. So you cannot make ends meet without being profitable. So we've always been profit-minded since day one. And there has not been a single year where we did not make a profit. And even more so in 2025, despite all the headwinds, Q3 of this year has been our single most by far and away profitable quarter ever. Because what I just told you that we have been focused on, it's never been truer than what we've done over the past quarter. Where we were forced, and it's all actually thanks to tariffs that forced us to be even that much more diligent.

1:10:04And zero-based everything we're doing down to even like, do we need to spend on Meta? Do we need to spend on Google? Do we need to fill in the blank? Every assumption that all of us are making on a day-to-day basis went to nothing. And let's reprove to ourselves in the current state what we actually need to do. What is the return? What should or shouldn't exist? And through that lens of just ruthless, and I mean ruthless prioritization, we've actually turned around the best quarter on the bottom line and still grew double digit over last year, which is kind of remarkable. You can still do that.

1:10:39purely by going line by line, literally line by line, every individual, every tech partner, every product, every single thing that exists. And I would highly recommend it to everybody. It's kind of tedious. It's a lot of hard work. But man, again, the complexity attacks, like it creeps up and you can't sit there and review everything all over again, every single time. So it's moments like that that just force you to really hit the reset button and you need that periodically. but those are the moments where if you saw pre-Q3 and to Q3 like it's a stark difference in how this business is trending and it's really from regaining the focus and killing a lot of the noise there's still plenty of noise to be killed in every organization ours included but that's one thing I would tell you that you can kind of see the more aggressive we are about that the more you see the business that kind of reacts positively to you so you re-baseline your business I mean, I think, Mike, we've talked about this earlier this year with tariffs.

1:11:36Like, what do you do when your company just doesn't work in a financial model level? Like, just pure model. You're like, well, how do I do this? And the answer is that you start from zero and you rebuild the whole thing. Rosa Meyer has a quote about Google that she said, you know, every time we grew an order of magnitude, all of our processes broke. I think there's a similar idea here that anytime there's a shock of a significant magnitude that happens to your business or the business environment, you pretty much have to rebuild the P &L because the previous kind of environment instead of assumptions that you had about the business no longer hold.

1:12:11And I think the Liberation Day was pretty much that. It's like, hey, you need to just start back from zero and say, okay, how does the P &L come together in a way that makes sense? And one of the questions I had is, as you guys were talking about your growth, you're obviously a scaled business now. I mean, You're probably still in SMB, but you're a very large one relatively. And I'm really curious how you think about goals when it comes to growth. Are you more profitability focused? Are you still in we want to get in as many homes as possible? How are you optimizing your growth? Yeah, I'll take that one.

1:12:49So first and foremost, we try to ground ourselves in what we're here to do. And I know it's going to sound cheesy, but it's the truth. we're here to empower everyone to look and feel good. And so the 10-year target is not a revenue target, it's not a profit target, it's not a cash flow target. It's to inspire and empower over 100 million people to look and feel their best with True Classic by 2034. And so we're just inching towards that. Now, reality from running the business and getting towards that, we care a lot about top line, a lot about bottom line. And we don't look at this on an annual basis, we look at it on a trailing basis.

1:13:23So at the end of every month, We look at the last, let's keep trailing 12 months. And how is that looking period over period? So we're constantly monitoring that. Topline, bottom line are the two North Stars. That's how we bonus the team. That's how we think about the success of the company. For me, top line allows us to see how many people we're able to attract into the brand with and actually deliver on that promise of empowering them to look good and feel good. When we do, they vote with their dollars and they come back to us. And then on the bottom line is like, we're running this responsibly And we can take that and reinvest it and make sure we continue to fuel the growth on that journey.

1:13:59And we are just about six plus million customers. So we're 6 % done on that journey to 100 million. Now, if you think about the third, it's cash. It's a really important one because cash flow is what kills companies. And we are basically using that as like a bumper, if you will, to not get too far over our skis in either way. So that's the triangle for me, top-line revenue, bottom-line profitability, and cash just to keep us in check. And that's really the short of this. And then if you think about micrometrics, Mike, everything will probably be at net revenue or profit as low as possible, whether it's gross profit, contribution profit, as low as you can per.

1:14:43So if it's the website, it's the net revenue per session and the gross profit per session. If it's the product, it's the net revenue per product and the gross profit per product. If it's a channel, you get the idea. per order, per customer, per something, to constantly keep the eye on those top line, bottom line metrics in every part of the organization. And that's ultimately the metrics we care about, go people against and try to track towards. When we see things that don't look good, we question like, can we fix that? Or do we need to kill it? Is it viable? Is it not? And sometimes it's like we have high conviction.

1:15:17I'll give you a perfect recent example. We really have high conviction on kids because we know that we have so many women that buy for their significant others and women buy for their entire families. And we have a really great kids' clothing. But what I think we potentially underestimated is how price sensitive women are when it comes to buying clothes for their kids. We created a really highest quality product for those little ones. That doesn't mean they're willing to pay the same amount they're willing to pay for the adults one because kids were in their clothes and fill in the blank. So we might end up thinking again, do we need to maybe change the quality altogether so we can lower the price even more?

1:15:55Or do we need to change some other stuff or just focus more on her versus the little ones? Or how should we think about it as a whole? And we're evaluating it as we speak through those two lenses. But I would argue that maybe we're still priced too high at the same time from a cog standpoint, it's the same as for him. So we can't really cut the model in a way that makes sense. And we have to like maybe find other ways to justify that. Perhaps it's an LTV driver that keeps her coming back. And when she buys for the kids because they size up, they buy it for the rest of the family. We have different ways to think about it.

1:16:28But those are the lessons we look through. And then we're ruthless at the end of the day. If we get to the conclusion, works, doesn't work, we move on. And we'll change our minds. Like there were years where we're like, let's go open as many retail locations as possible. And then there is another thing where it's like, maybe not. Let's go lean into wholesale. Or maybe let's do more marketplace. And we evolve with the business based on where we see performance trending. Wherever performance goes, energy flows, and that's just how we operate. We f***ed up to say it nice and concisely, okay? We thought this was going to be a slam dunk, so easy.

1:17:00Let's just do a smaller version of everything. Who's not going to buy this? Everybody. So we are trying to figure it out. We're making some price cuts, I think, to help get it more palatable. But we don't do everything right. you know we've up the sizing a little bit it's not perfect it's better and it'll continue to get better we've got a lot of things on the first go ahead too when it comes to product like we don't they're subtle things either the hem is too long or the the point to point on the shoulder is too wide or you name it like we do things the wrong way first a lot of times and then we go oh here's how to make it better here's how to iterate here's how we should have done it the v2 the 2.0 is coming.

1:17:45So we're just used to that. That's just kind of how we roll with product. It's really understated how often big companies screw up. It just gets hidden by the fact that they're successful and that they have really strong product lines in other places. Like Google can do incredibly stupid things and nobody notices because they've got such an amazing... Yeah, like GA4 for all of us so that we have to go use Triple Whale and keep analytics. Thanks for reminding us. just like Google Analytics. Guys, not a single UI UX person in that entire department, by the way, in GA4. I just want to say, can we stop having engineers build analytical software that gets used by people?

1:18:25Not other engineers, human beings that have to run businesses and make things easy to look at. It might be one of the biggest own goals that we've seen in e-commerce. Just being like, hey, this product that everybody uses has 100 % adoption. What if we just killed it Insane. And gave me something way crappier instead. So one of the things that comes through talking to the two of you that I really appreciate is that you're clearly actually a mission and values driven business. And I think the best businesses always are. There is an organizing principle that's bigger than, hey, let's make a bunch of money.

1:18:59And you clearly have that. What I'm curious about is how do you balance your personal financial goals with also chasing after the mission and values of the business. I'm going to start this one because I want to start talking about Ryan again. He is the single most generous person I've ever come across. So I told you how we have complementary skill sets and at the same time, we're very similar in other ways, but there are certain things where everybody has just a spike. So one thing about Ryan is that he's just legitimately and genuinely a very generous person. He truly is a giver and he gives without conditions.

1:19:35He's not waiting for you to, if he gave you a poker chip for$100, for those of you who don't know, we created those poker chips because he's a poker player. And we basically put store credit and we give it to random people. Right here, Ben. It's not meant to be. That's right. Yeah, I have it too. I use it as a fidget. It's got so much value to me, guys. So you know what's interesting is, Matt, it's not meant to be this marketing tactic and here, take 10 % off, so you give us some money and what's the LTV and how fast do we get paid back? It's truly meant to surprise and delight. and it goes to the people who don't expect it.

1:20:08It can be the Uber driver who just dropped some food here and gets$100 for True Classic. He didn't expect that. It can be a cashier. It can be a doorman. It can be whoever. And it's amazing what it does to people when you actually just give for the sake of giving. And I think, Mike, the best answer I can give to you is like people are actually, what I've learned from Ryan a lot too, in a way are over-calculating the give and take and how to balance the equation. Whereas the reality still stands that if you are a true giver and you're here to create value, your share of the value created will always be there.

1:20:48You're not going to starve for money. You're not going to starve for financial success, for freedom, because you created such an exaggerated, if you will, value in this world that your share will be fine. And I almost feel like we're not necessarily calculating the approach, We just have this deeply rooted belief that we need to give and we need to do right by people. An example for that, and Ryan truly, I think it's how he was raised with a lot of charitable work and just deep rooted values. You know, if the fires happen in LA, we literally turn everything upside down and made the office a donation center because people needed clothes.

1:21:25They lost everything. And that wasn't like, hey, is this within our budget? Do we have time for that? What happens to this? This is how we not do it. It's like, dude, what's more important than showing up to our community in a moment where everybody suffers so much? And those were some of the most moving moments I've had in this company. People came into this office in tears and they were like, how much can you take? As much as you want. We literally just kept shipping here pallets. It's like, take whatever you can and send it to your friends. Who cares? We're not keeping tabs. We're not counting how much we can donate.

1:21:57We're not trying to make a PR release around that. We're just here to show up to people. and it's interesting how actually underrated, in my view, generosity and giving actually is, but it's for people who do that genuinely and not for the return. It's not for, hey, here, you do this, then you're going to get a headline or an article or fill in the blank. And I think one thing that Ryan is really rooted in this culture, and I'm really giving him all the credit because it's not me. I would say I think I'm okay on the generosity side, but I'm not him, is that he encourages everybody to come up with ideas.

1:22:33So if you learn about a crisis in the world, like Ryan wants you to raise your hand and say, here are people, they're suffering here, something bad happened. Okay, how do we show up? Or it doesn't have to be a crisis. Like another person, I'll give that example, which I think is beautiful. Her name is Tiffany and she raised her hand and she gave this idea of like, you know, teachers struggle every year to get the supplies that they need for their kids. And what's most important, I mean, for all of us, we're all parents, like make sure these kids have what they need. And so she brought up this idea of like, what if we help them?

1:23:00So Ryan literally just started like clearing teachers wishlists on Amazon. Just like find all the wishlists and just like clean them, just pay for all of them, just send it to whatever they need. And it was like, it made such a moment of like, hey, this clothing brand that has nothing to do with teachers, this goes out there and clears teachers wishlists. Why? Because why not? And you probably have a whole lot more stories around that. But I really don't think it's a calculated strategy so much, Mike. No, not at all. It comes from a genuine place. It's the soul of this brand. And it's honestly why I created it to begin with was just to provide value at scale.

1:23:37Because remember, when I started True Classic, I had already made money. I was good. I didn't need to complicate my life and go through all this chaos of e-commerce and have all these people working for me. And like, I didn't need any of that. but it came from this place of like I've got to do more with my life than just make money I have to be able to make enough at scale to where I can deploy it into the world however I see fit push it into initiatives push it into people push it into helping whatever that looks like and so when you start a business with all of that in mind from the get-go you build everything around just giving and love and listen I am not good for the P &L probably on the surface because I over give but I just think if you can't legitimately give away your product and have someone love it, you should really go back to the drawing board of what you're doing in business because it has to be something people love and you have to be doing it for the right reasons if you want to scale it.

1:24:33And if you come with that mind frame, you will do that in every part of the business, not just employees, but customers and everybody involved. Like I truly think that one of the things that I try to do with all this giving is show people what it's supposed to look like. so that they can look at themselves and go, am I doing enough in the world, right? Like this guy's over here doing this. What should I be doing around my circle? Who can I give to? And so a lot of times I would gift poker chips, like stacks of them to people and be like, look, now you're the giver. Go be a giver for a while. Tell me how that feels.

1:25:07And they come back like, you have no idea. It changed my life. I didn't realize how much people needed something small, either a poker chip or whatever the gesture was. And I think once you take a piece of that or a little bit of a taste of what generosity truly looks like, you become absolutely addicted because it is the greatest drug in the world. And I truly feel it's what we're all really meant here to do on some level. I mean, all you guys are creating immense value for people at scale. Right. That's truly what your calling is. And that's why you're here. Now it's just a question of what else can you do outside of just business to create value for the world outside of product, right?

1:25:49Like I know we all have different initiatives that we're involved with and ways that we help other entrepreneurs. And we do stuff like this because we know there's a little kid sitting in another country that's going to listen to this someday and go on to build the next Gymshark and be totally inspired by all of us sitting here and talking. So it's just really foundational to the business. it's a big part of why it continues to win and why people gravitate towards the brand because it's not lost on them that we lead with love and that it's not just about making a shirt or making it fit right it's like we try to create value in everything we do with the ads the service the product you name it you're going to find a component of love in every part of this business and it is truly the through line and what we care about i gotta i gotta ask then like that was awesome, by the way.

1:26:36And I think that we like I know I do. And I know Mike definitely shares that philosophy very deeply. Right. So I love that you guys went there. Where do you see the company in five years then? Like if you're starting from this place, like you're so mission driven and so purpose driven and even like right down to how you think about value creation versus capture. You know, if you look out five years from now, like what does this company look like if in an ideal world. I want it to scale simply for the selfish reason that I can do more with that cash and I can wield it better than I feel anybody else can.

1:27:11When I look at, you know, the way our money gets deployed in the States with our taxes, I'm just, I'm exhausted. And I just feel like I wish some scrappy entrepreneur could just get in there and balance this budget correctly and get the money to be. And it's, and it's like, that's really my dream is like, let's get this to Kirkland levels. Let's come out with the chocolate covered almonds. Let's scale a crazy category and start building towards something bigger than just apparel. Like I really think we can tap into luggage and watches and all sorts of other things that can get us beyond what the apparel companies are doing.

1:27:48Like the bigger guys are all doing somewhere in that five to seven billion range. But if they were to crack another few categories beyond that, if they had that entrepreneurial mindset, they would be doing 20, 30, 40 billion potentially and get to the Kirklands of the world who have figured out product expansion and innovation. So that's where I see it going. Is it going to be there in five years? That's going to take a lot of work. Probably not. But can it get there in 10 to 15 to 20 years? Absolutely. And then what do we do with all that money? We deploy it into the world and solve a lot of problems for people and create goodness and hopefully, you know, just create a lot of value for very large amounts of people that need it.

1:28:24One observation I would chime in here with is that because you're driven by values and it sounds like a big part of the quality of life that you get from the business is actually impacting other people's lives. Your runway as entrepreneurs and as leaders is going to be basically your entire adult life. And I think when you get consumption minded of like, I'm trying to get to a number I'm trying to get so that I can buy this thing for me, I can have this lifestyle for me. You you burn out quick, even if you're really gifted, because that's not a motivation that's going to sustain you for 10, 20, 30 years.

1:28:59And that's what it takes to build a great company. Yeah, because it's not about the money. Not anymore. I actually would say I would encourage everybody to do that. I told you about the company's purpose, but I would encourage everybody to come up with their personal purpose statement. Hell yes. For me, it's to inspire and empower others to become their best selves. That's literally it. That's what gets me energy. That's why I love sharing knowledge. That's why I like to inspire others to really push themselves, sometimes in really meaningful ways. But it's just across the board. So if we're doing it with product, let's put them...

1:29:33When we say look good, feel good, that feel good is a sense of confidence. And what happens to guys when they feel the best version of themselves is they're ready to crush no matter what it is that they're doing. It can be work. It can be a relationship. It can be just how they show up in the world. And if you are giving to somebody something that they didn't expect, what happens next? They want to match that. There is givers, there's takers, and there's matchers. But matchers in the world are the vast, vast, vast majority of the population. And they will match whatever they see. So if they see givers, they become givers.

1:30:07I've had so many comments. You know, in the early days, we didn't show a lot of the philanthropy because I just thought it was totally cheesy and I didn't want people to feel cringy about it. But what I realized is the more videos I created around the giving, I would have people in the comments be like, you know, I saw this video a couple of weeks ago and it inspired me to pay for a guy's gas the other day who just couldn't afford it. And it breeds this philanthropy amongst all of us. And I think that is just truly an amazing gift to give people through this type of content, which is just like create goodness, put it out there and let people reflect.

1:30:42And hopefully they take something away about what they could be doing for at least one or two people in their lives. Yeah, and just to chime very briefly on the tactical of what this brand is about and where we're likely going to be. Product-wise, we're going to move from a menswear brand to a familywear brand. Women is going to probably be a way bigger chunk of the business than it currently does not exist. Kids will probably figure something out as well. So that's one thing. But I would say primarily still clothing, if I were to guess. although I don't know, there could be either adjacent categories because again, the purpose is to - Clearly you're going into chocolate covered almonds, Ben.

1:31:14That's the next thing, right? So that's on that. I would say international, I would expect to grow a lot bigger and for us to truly double, triple down on large markets, growing the presence in the UK, in Canada, in Australia, in Germany, in Mexico, things like that. And then on the channel side, I would say we're going to probably be a whole lot bigger from a physical presence standpoint. I foresee that becoming just absolutely huge. And if anything, just for the reality of the market, it still, it tends to be the case that over 60, 70 % of clothing is being purchased in a physical retail environment.

1:31:47And so from a business standpoint, I would expect to find true classic in almost every big department store or retailer, having more of our own stores as well, and continuing to double down on online with D2C and marketplaces. So those are still the avenues. Exactly how and where and when, we are very opportunistic. And we just move with speed and continue to develop. As I mentioned, where performance goes, energy flows. We do this thing at the end of every show. I'm glad you went there, Ben, where we do what we call the Titan 10. It's basically like we've got 10 questions. And since there's two of you, I think this is going to be kind of fun.

1:32:28So what I'm going to do is, if you're cool with it, I'm going to start asking the questions. I'm going to tee one of you up, and I would like the other person. So if I ask Ben, if I ask you, Ryan, I'm curious to see if you agree or if you have a different answer. Okay? And we'll just flip-flop. Okay, so I'm going to start with question one. The first is you guys get to a desert island, right? And you get one little dashboard, and on that dashboard are three numbers that tell you how the business is doing. Ben, since you're the analytical one, you start. What are the three numbers? Net revenue, net income, cash flow.

1:33:05Ryan, any change? I would just add blended ROAS because I'm taking into account just the sheer profitability on any given day across all channels. I just love that number. I'm so we've been incredibly focused on that number as a business since literally day one. We built the whole business basically on a Facebook row as early on because it was such a big part of the spend. And today, obviously, we have to blend everything because we have so many different other channels. But I agree with those numbers as well. I mean, I think at the core what it matters. OK, you guys also get to bring a book, but it can't be a business book.

1:33:51Ryan, what book do you bring?

1:33:55I mean, I have to say the Bible, but business-wise, I would say - No, it can't be business. No. Can't be business. Oh, it can't be business.

1:34:07It's hard, isn't it? I don't read anything other than business. Ben, what about you, man? You got a non-business book that you would bring with you. I really am not. I don't read. Frankly, I listen to pods. I catch up on reels I would take a book I would throw it into chat GBT and summarize the key takeaways and go to the next book I don't know if I have like one that's just a go-to one that I got recently that I like is the Elon Musk photography business and yeah but it's a person thing I like that I find it so inspiring how he can be just the absolute and you know maybe it's controversial some people like some people hate I don't really care but from an ultimate value maker, problem solver, first principle thinker.

1:34:54Have we ever seen anything like that? I don't think so. And so as an aspiring Elon person, like I find him to just be such an inspiration. So like learning more about the guy and how he goes, about carrying himself in life, I think is something I would always find. Oh, I love that. Interesting to me. Okay, so then here's my fault. I got, this is like teasing up the next question so well. What's, so you're talking about like contrarian, but like is there ryan do you have a contrarian belief about business that you think like most other people like the point of being contrary is like they just don't agree with you on it yeah it always goes back to the giving part because everyone sees it as a loss and what they don't see is how things come full circle and what that actually meant to that person that you did albeit a small little thing like a poker chip or whatever it is no one ever gets to see the full picture of what that looks like as it manifests in their life later.

1:35:47And we get lucky enough since we deal with the same Uber drivers that are in the area, you know, when they deliver food, it's largely the same area. So I get to see what it looks like when you give something and then you see him again in a week from then. And if you could feel the gratitude and the thankfulness and how much something so small impacted their life, it would force you to change as a human and you would completely start moving differently in the world. So I would just say that giving is so much bigger than we realize and it affects people on such a deeper level than we realize. And it wasn't until I started really doing the poker chips that I got to see it firsthand.

1:36:24I always knew it was special and people loved it. But when you get to feel it really face to face, it's addicting. Ben, what about you? Do you have a contrarian belief? I would double down on what he just said. And I don't know if it's a contrarian view. it might have been heard by many, but I find it to not be practiced enough, is true consumer and customer obsession and centricity. And by that, I mean, and I'll give you like one particular example. We let customers make all decisions. I touched on it earlier today, but if you notice all our clothes, unlike any other clothing brand, do not have the logos on them.

1:37:02And this is not a mistake. This is us asking people what it is that they value and they tell you we do not want logos and we say fine, even though commercially that might be a dumb idea, not turn them into walking advertisement for the brand. Yeah. And most people say that they're customer-centric, but they obsess over what other people are doing and what are the latest, greatest trends and fill in the blank what their body just said and they forget that there's only one person or even what they think or what they believe or what they value, what they like. And there's only one person that matters, which is the customer.

1:37:39Love it. So like true consumer centricity, not said, but done, I think is completely, completely underrated. Super cool. I guess, I mean, okay. So then my next question has to be, if you have to pick one word to describe leadership, like your style of leadership, maybe Ben, you go first. What is that one word? What's the single most important word in leadership? Clarity. Ooh, Ryan. for me it always goes back to getting out of your own way and being incredibly the most objective person in the room because if you are the truth lies in that not what you think or what i think or what she thinks or he thinks or i can't wait to tell everyone my great idea it's just like what is the best for everybody involved and just get out of your own head and what and what it is that you think is the right way.

1:38:34And let's just be objective. Okay. So then on that, what's the single most important word in business to you, Ryan? I think that if I had to distill down to what I care most about is this component of curiosity, because the curiosity leads you to the right solutions. Ultimately, if you're very stuck in your ways and you don't believe there's any other way, you'll never truly get to the best possible piece of software or whatever it may be, or even the next product that could completely change the business. But if you're constantly pressure testing what you have around you and what could be better, this is something Ben does a really good job at.

1:39:12It was just like being infinitely curious will always lead you to the right path. As long as you're being objective, once you get there about what it is and what you're seeing, but cause you have to be able to pivot off of your original source of truth of call it, you know, we have a lot, we all have a big tech stack, but like every year you should be reimagining what that looks like across literally every single thing that you do and going who's the newest ai guy who's out here crushing even though this could be scary i want to take a leap of faith and see what what everyone's talking about love it ben what's the most important word of business to you Ibitda?

1:39:53Jokes aside.

1:39:59That's a bunch of words. I know, right? That's the acronym. A single most important in business?

1:40:09I'll go with intentionality. I feel like if you move with intention, intention, which is in many cases, a summary of you explored for the truth. You gathered some insights. You were curious. You asked the hard questions and ultimately bubbled all of that to like, I make intentional moves versus, and it's a little bit of what Mike touched on earlier today. It's not just speed, but it's kind of in the right direction. The outcome is typically going to be a whole lot better than if you just make moves. So being incredibly intentional is so important in business. Love it. Okay. So I got a fun one then.

1:40:44What is your favorite meal of the day and why? We're like very, we're trying to be very light eaters these days because, well, I'm getting old. So like, I just can't handle chicken parm at 12 like I used to. No kidding. Our favorite food. I mean, Ben doesn't even barely eat food. You could stick literally a shoe in front of him and he would just start eating it and be like, oh, this is a shoe. I didn't even know. And he's halfway done. I probably I think Mendocino I'm loving Mendocinos lately Ben doesn't even know what he eats I would say middle of the day is lunch I don't eat breakfast I typically make it to about noon and then get really hungry unless it's right there and then I really try to eat healthy now so we have Irwan which is completely overpriced but it's healthy food salmon, rice, cauliflower $40 for salmon Most irrational purchase you make of your whole day is Erwan.

1:41:47But it feels good. I know. But it's like we really just do not leave our desks. We work like athletes. Yeah, we don't take lunch breaks. We've not taken a lunch break in four years. A whole day. On the same way. I sit at this desk and, I mean, it's a mess in here. We just don't move. This is also my lunch table. Yeah, exactly. So that's it. Very cool. Okay, so last two questions. I want the most overrated growth tactic right now in consumer. Oh, my God. Ben or Ryan, I don't care who goes. Just like that's an easy one for me. The most overrated, in my opinion, are these big splashy brand activations that people do and spend all this money on.

1:42:26Having lived through many of them now and spent big splashy money, it is really tough to make sense of it. You know, if it doesn't show up on the post purchase, it might as well not exist. and you know i'm really reeling back this year on that front um i am cutting a lot of budgets because if it doesn't make sense it doesn't make sense and i'm not just going to do things just to do things even if it's a cool opportunity where we got our logo on the the scoreboard like i'm just not moved by that anymore so like unless it has something to do with giving back to the community or giving back to fans and taking a fan from the top of the raptors to the front seats or something amazing for somebody and creating a real experience.

1:43:06I don't want to do it. So that is really overrated. And I would say your dollars are much better allocated towards Facebook and creative. The end. Don't think about anything else. Tunnel vision. Make your stuff great. Show it to people on their phones. And that's where you should allocate the dollars. That's great. OK, then, Ben, what's the most underrated tactic?

1:43:33I think right now, building an army of creators, affiliates, influencers to be your digital sales force is perhaps the single biggest thing that anybody can do for their brands. And listen, it's not new, but what you see these days on TikTok shop and what happens after with the halo effect, it's un-freaking-believable. and I believe that if you do that right, as in like not check the box and some automated robotechs and DMs, but legitimately go and self-curate creators that want to drink the Kool-Aid with us, sell people on the dream, tell them what this brand is all about and really increase and grow the fan base.

1:44:21I legitimately think the sky is the limit and then you can take those creators and they can actually start recruiting additional creators and really roll that social snowball. I love that you said that. It's at the top of my list for 2026. Is that exact thing? By the way, this thing right now. Very, very difficult to actually execute versus just say, do TikTok shops. That's why it's so exciting. I see a lot of people doing, you know, a three out of 10. To get to a 10 out of 10 takes an unbelievable amount of time and execution on the leadership's part. Not the affiliate manager, not the agency that you hired to run TikTok shops, from the people at the very top, building connections with the influencers and the creators, taking the time, putting your effort into really making it great like you did everything else in the business.

1:45:11You know what I mean? Like building community is not easy. You have to be incredibly intentional and you have to think about it and you have to offer people incredible value. That's so good. And if you just build transactional relationships with these creators, then you're not going to get the kind of results you want. Like, I think this is one of the things that I've noticed. You have to find some way to create a relationship that is more than, hey, what are you charging a CPM? Okay, I'll pay that. Otherwise, there's no way to sustain momentum, I guess. There's no way to kind of build it into a point of leverage for your business.

1:45:44So we're constantly trying to figure out how to do that, not just how do you build it. I mean, you guys said it. It's almost like an external sales force. Well, how do you do that where there's a group of people that are actually believers in the brand? They want to push the brand, not just you're the checkbook. that's willing to write them the check, but that they believe in your mission and your values and that they're willing to do it over a period of time. That's the thing that is really rare and takes hard work and very few people are doing. That's so good. Well, Brian, Ben, that brings us to the top of the hour.

1:46:16Brian, I know you got to go. I got to go. This was fun, guys. We got to do this again. I just like doing it, man. I'm going to be in LA at the end of the month. I'm going to find a time. We're going to hang out. Bye. We're going to make a poker night out of it. I don't gamble. That's the problem. I'm not. I don't know how to do that. You do now, buddy. I'm just going to lose. I think playing poker with you guys would be a great way to donate a bunch of money. Low stakes. We'll keep it friendly. I was going to say. Oh, it's so good. I'm notorious for losing all my money to this guy, and he loves it.

1:46:49Well, he shoves on me with a subpar hand. He wants me not to call. I mean, what do you want from me?

From the publisher

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What does it take to build a ~$300M apparel brand from scratch?


Matt Bertulli and Mike Beckham sit down with Ryan Bartlett, Co-Founder, and Ben Diamond, CEO of True Classic, for their first-ever joint interview. Together, they unpack how a professional poker player and a Meta executive became one of the most formidable partnerships in DTC + built a men’s and women’s wear empire on the back of white t-shirts.


From the early days of consulting on Facebook ads to their obsessive focus on fit, speed, and customer value, Ryan and Ben reveal why they cut 80% of their product catalog, how tariffs forced their most profitable quarter ever, and what it really means to “seek the truth” instead of being right.


Plus, they get into AI-generated creative, why big brand activations are overrated, and the surprising power of giving away $100 poker chips to Uber drivers.

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