Living The Red Life - The Art of Branding: Lessons from Chubbies Success Story

Episode Date: August 18, 2025

Preston Rutherford is a renowned brand product owner, co-founder, and entrepreneurial expert known for his role in establishing Chubbies, a successful consumer brand famous for its colorful, casual men's shorts. With a strong background in brand development and digital marketing, Preston played a key role in growing Chubbies from a startup to a public company with a $100 million run rate. Today, he continues to influence the entrepreneurial landscape with new ventures and insights into brand-building strategies.With an emphasis on entrepreneurship, Preston and Rudy discuss the trials and triumphs faced during Chubbies' growth, from initial inception to a public company. Key topics include the importance of standing out in a crowded market, maintaining authenticity, and navigating the ever-evolving digital marketing landscape. The conversation also touches on personal insights about overcoming startup challenges, focusing on one's strengths, and making strategic business decisions. This dialogue is a must-listen for entrepreneurs seeking to build impactful brands with sustainable growth.Key Takeaways:Embrace differentiation to stand out in the marketplace; commoditized products can succeed with the right brand story and creative marketing.User-generated content can be a powerful tool for creating authentic brand engagement and fostering a sense of community with customers.The journey of entrepreneurship is fraught with challenges, but persistence and focusing on core strengths can lead to eventual success.Understanding the balance between generating demand and capturing demand is crucial for brand longevity.Collaboration and strategic partnerships, including offering equity, can be essential for acquiring the top talent needed to scale a growing business.Notable Quotes:"Everyone doesn't have to be exceptional at the best thing." — Preston Rutherford"You just have to be in the arena, constantly doing it and trying to learn." — Preston Rutherford"The opposite of apathy is memorable content; don't focus too much on pleasing everyone." — Preston Rutherford"If you're not good at it, hire, pay the money, and find the good people to do it." — Rudy Mawer"The true enemy in business is apathy, not people disliking what you do." — Preston RutherfordResources:marathondataco.comPreston Rutherford - Linkedin & XConnect with Rudy Mawer:LinkedInInstagramFacebookTwitter

Everyone doesn't have to be exceptional at the best thing. I say, you know, if you're not good at it, but you've got to then be willing to hire pay the money and find the good people to do it. Totally. And I think the other thing that might stop entrepreneurs is what you were doing back then now is what the econ playbook is, right, around content. But back then it was way more unique and, you know, you had much more organic potential too, right? I think we've gotten into maybe like a smaller sphere of maybe like what,

community or UTC content looks like where it's very focused like on the unboxing experience or like something shot in the home where it's like hey here's here's my problem here's my solution and here's the reason why you should believe me i think we get into these ruts where it's like okay everyone's doing this so we got to do this or here's what this company does so i'm gonna do this i guess the point maybe i would try to leave people with is my name's rudy more host of living the red life podcast and i'm here to change the way you see your life in your earpiece every single week. If you're ready to start living the Red Life, ditch the Blue Pill, take the Red Pill, join me in Wonderland and change your life. Hello and welcome back to another

episode of Living the Red Life. Joining me today is Preston. He's a brand product owner, a very successful one. It was one of the co-founders of a brand new maino called Chubbies. I've definitely owned a few pairs during college and all my college friends with big fans. So excited to dive in and talk about the brand and the entrepreneurial journey. So Preston, welcome to the show. Rudy, thank you for having me. Pump the beer. Yes, so let's talk about as an intro, like most people probably know the brand,

but you guys hit some pretty big benchmarks and achievements, right? Can you just talk us through, you know, how Chuby has grown, right, from where it started and some of the big achievements and journey? Sure. Yeah, so started the brand, one of four co-founders, started it in late 2011. and, you know, went through, I think, all of the journey of highs and lows of building a consumer brand. And just a small part of the team, but very fortunate that the business went through a great acquisition and was part of an IPO shortly thereafter and is now doing extremely well as a public company, 100 million plus run rate, very profitable, still growing, kind of a testament to building a strong brand. Yeah, and what I love and reason I wanted you to come on is I like to look at business.

is where it's like, hey, we sell socks or bottles of water, right? Like I always like to use liquid death as a great example because people think it's hard to sell and I'm like, no, you just lack creativity, right? And I think shorts and stuff is a good example of that. There was a lot of like when you started brands that sold shorts, right? So how did Chubby stand out and do so well and hit like, you know, that avatar, right? You did such a great job of like hitting the avatar of me and my friends when we were in grad school. Can you just explain that to the audience that don't really know the story behind Chubbies and why it was unique?

Sure. I think the general idea is how can we be the opposite of what status quo was at the time, right? Think back 2011, so now what, 14 years ago, there was a very different vibe associated with men's fashion, right? It was very serious, too cool for school. You have to look a certain way in order to be the in crowd. And so our idea was, let's just try to be the opposite. it. Everyone can just do themselves. We had elastic way. That's probably why I liked it, because I've always been kind of outrageous and different. You know, I've seen see the red hair

and everyone knows me for this. So it's probably why I was a big, big customer of yours back in the day, too. Totally. Yeah. I mean, just, yeah, be yourself. That's great. Stand out. I mean, we did bright colors, right? They were obviously a shorter short, which was less common at the time. But to your point, still a commodity. I mean, it's just a pair of shorts, right? So, So we had to stand out and try to build an association with that commodity product to justify, right, the price point. So, yeah, it was basically the general idea of, hey, this is kind of like the vibe of a group of friends that is continually growing, that being the customer base. And so everything kind of laddered up to that, our communication. It was like, we're not a company talking to customers.

We're just a friend talking to another friend, right, treating you as a friend, like not some faceless customer. And then just trying to make the best possible content, like in the same way that you might share photos of your weekend with your buddies, trying to replicate the same thing rather than what was normal at the time, right? Which is like these highly produced, very expensive, you know, fancy models, posing. You know, we're just, again, tried to do the opposite. And then just like it was a time where, you know, you could get massive organic reach. So if you were just doing interesting things, you mentioned more creativity, you could just reach a lot of people and get them to care and pay attention. A lot of the basics, I guess, that seem a little bit more obvious today, but at the time, you know, a little less obvious. So just tried to like rise above the noise, but be consistent to this idea of you don't have to look a certain way to be sort of included.

Like elastic waistband meant if you ate a lot, your shorts still fit, right? It's not about like having a six-pack waist or whatever like that is. It's just, right, you are who you are. And then content, right? How can we just create things that are memorable, shareable, right? all of the basics, right, but we can so often forget, you know, when we're trying to hawk products online, right? We become very product off our urgency and we forget, like, that works maybe in the short term. You still have to do it, but it can't become the overwhelming majority of the things

that we're doing. So as much as possible, try to just remain focused on, okay, at the end of the day, we're going to try to put out one piece of content every day that could be in the running is the best piece of content any of our viewers see that day, regardless of who it's from a brand, a friend, an influencer never did that or it was very hard to do that right, but having that as a filter or standard, I think it's something that might be useful for the audience as like a reframe for like, what am I putting out into the world? Yeah, I love that. And I mean, let's talk about the content because, yeah, I mean, you did such a great job with that. I'm like trying to remember back 10 years, but like even 10 years ago when I was buying it and my friends were, it was like

you definitely understood the avatar, right? And you created content. and images that was relatable to the avatar, but then also shareable. You had some really cool, funny content. So can you talk about, you know, maybe one or two highlights or one of your favorite ads you ever made that broke the internet or did well? Because I know you had some that did very well. Yeah, there are some that did really well. I mean, I think two things.

One, it was about, maybe less about an individual piece of content, but more about just taking a lot of shots on goal sort of thing. And then the ones that you just, and I think maybe a lot of us who are listening to this podcast, I've experienced something like this, where the thing you just have no idea is going to be the thing just takes off, right? But it's, so it's about being in the arena, right? It's just about constantly doing it and trying to learn. And it was never the one that we spent the most money on, right?

It was never the one that we hoped would be the thing that really just kind of like took off. And then even if you try to like reverse engineer it, you know, it kind of would work, but not really necessarily. So I think the lesson there is just a feedback loop, constantly. trying things. And I think the second thing was having built an expectation with our audience that they could, I mean, UGC is so obvious now, blah, blah, blah. But at the time, right, it was like new that people would like be part of the marketing from a brand. But having built the expectation over years and years and years, we would feature our customers. Like that was

relatively novel at the time. But it ended up being this massive content engine for us, just organic content coming in and then people just like loved being featured being called out right they felt like a hero so i think those two things like just from a process perspective really kind of i don't know stood out not that it was ever perfect right um but it was just yeah those are maybe the two takeaways of just like you know process and building this expectation this association this association over a long long period of time yeah i mean i think it's funny because what what you were doing back then now is what the ecom playbook is right around content but back then it was it was way more unique and you know you had much more

organic potential too right so when you hit hit those good notes that it just takes off and i always teach as i say you know social content's like a dart board you just got to throw a lot lot of dots right and you know we've spent five 10 15 grand on an ad 30 second ad where we're like oh this is going to break the internet and it doesn't then this like random selfie you shoot like goes viral and it's always frustrating but it's always the way so it's great to hear that from you too yeah yeah absolutely and maybe the one nuance from today is like i think we've gotten into maybe like a smaller sphere of maybe like what community or uc content looks like where it's very focused like on the unboxing experience or like something shot in the home where it's like hey here's here's

my problem here's my solution and here's the reason why you should believe me whereas i think there's an opportunity to just from the perspective of cultivating like real community like treating these people as your friends and then just like fueling the fullest life that they could possibly live and then the output of that I think tends to be content that can be difference making where it can be inflection point making that I think today what I see is most needed is just not enough content rises about the noise right and it's because I think we get into these ruts where it's like okay everyone's doing this so we got to do this or here's what this company does, so I'm going to do this, or is there, I think there's just a broader

aperture of what's possible. Yeah, yeah. And I mean, even, again, my memory may serve me wrong, but like I feel 10 years ago, your ads were kind of represented as actually what my college friends would be doing, you know, slamming a beer, jumping off the back of a boat or jumping in the pool with these brightly colored swim shores, right? And that's why it did well, because it was real life, you know, just turned into an ad. Yeah. And I think the other thing It was just sort of like treating your customer as an adult, right, where they can see, can I say bullshit, where they can see through the bullshit, right, of just bad advertising or advertising that is just like checking the box where we could just like, hey, I know you know what I'm doing, right? We all know what's going on here. And that kind of treating your customer as an adult or that you have an inside joke with them.

I mean, those sorts of filters I think always drove what we were doing to where when you look at something, it's just harder to just blindly scroll by. Not that everything we did did that, but there was just this notion of like on the marginal basis, right, engendering a deeper connection, where it's just like, come on, we're buddies, we're friends. I got to sell stuff. You want to buy stuff just like we're doing something together here. And just, I think that tone that you take that is behind everything you do can, I think, differentiate you over time. Yeah, I like that.

So let's talk a little about the business side now, right? You had a lot of fun, I'm sure, doing this brand with your friends. and these cool ads and, you know, building this. Surprisingly hard. I mean, you know this. You make great content, right? It's hard to make it look like you're having a great time. Well, that's where I'm going.

Right. And then, you know, I built a company over 100 staff and multiple eight figures. And there's a lot behind the scenes, right? You know, someone, someone sues you because you use a pattern. You shouldn't have used and you had no clue or whatever, right? Give me a couple of the horror stories where you're like, oh, my God, this is the end of the well, they've been able to pull apart, you know. Sure.

Well, that, your exact example, multiple times. Okay. You know, I think, yeah, people coming at you from a variety of perspectives, right? I mean, just like trying to take the things that you're building and, you know, they, even, even if you know, it's just like a ridiculous thing and it's going to end up being a time suck. And, you know, there's just. Well, most of them are, right? Once you get successful, most of them are just like, oh, but here's this BS. Okay.

Yeah, totally. And it does take time and it's just part of it, right? And or they hate, you know, like I think part of building a brand is that there has to be something that is so clear that it is hateable, right? And that's okay. You know what I mean? Like, I could be wrong, but I'm sure there are non-zero people who talk shit about the red, you know? And you're like, yeah, stupid red hair. It's funny because most of my eyeing paying customers, you know, I do corporate consulting. So big, more than six-figured contracts and. consulting deals. And a lot of them are like, when I first saw you, I thought you were an idiot. And then I had you speak and teach. And then I was like, I got to hire you. You know, how it normally goes. Yeah. So there's that too, where there's the transition where there has to be something to react to on that first impression. And it's okay if they're like, not for me. That's good for a couple reasons. Right. There's something that is memorable enough than to react to. Because the opposite is apathy. And that's the true enemy. It's not that just I don't want anyone to hate me. I just don't want to create something that is in one ear and out the other.

Well, that's why most brands fail. I think I teach this and most entrepreneurs because we're groomed our whole life to fit in, right? Through childhood, we don't get bullied, all these things. And then it's like actually entrepreneurship's the opposite, building a brand is you've got to go and be crazy. Totally. You've got to be crazy and you got to, you got to, you can't people please across the board, right? You've got your customer and you serve the hell out of them and you make sure that they tell everyone about what you do, but you got to embrace, embrace the haters and you can't make everyone happy, which is, yeah, to your point, something we're brought up to optimize around. So there's that. And then the other piece is, I mean, we had really tough times, right?

I mean, about we had a midlife crisis, so maybe five or six years in where, you know, the Facebook ads weren't working anymore. Yeah. Our product, you know, we had to shift where we were making our product because the economics no longer made sense. And that was really hard. And so then we had no inventory and all of that stuff. And we ultimately had to, and it's very embarrassing and sad, but like had to let go most of our staff or much of our staff, right? And that was just like a very tough moment because you're like five, six years into a business, haven't had an exit, you know, I haven't really done anything that you can look back on

and just be like, what do I have to show for this? And so I had to basically rebuild the business. And, you know, those are like the real challenging moments where it's just like, what, am I going to stick with this? and very grateful that, you know, the other founders and the whole team stuck with us, right? And, but there's crazy stuff, man. I mean, I think every day and you know this, you feel like you're going to die. You feel like you're on top of the world.

You know, and that's just the joy, right? It's the joy of this whole thing. Yeah. And I think it's also like most, I think I teach a lot. Most entrepreneurs don't become eight figure plus owners because a lot of them can't actually move out of that stuff. product mode because like becoming a CEO and managing a big company and team, it's wildly different and most people don't probably have it in them from a mindset standpoint or logistical operational standpoint. Like you go from like making these cool shorts and cool content to like working

with HR, attorneys, finance. Like, you know, I'm sure with e-com, all the logistics of getting, you know, 100, you know, not selling out, I'm re-sucking and then managing inventory. Like it becomes I would love for you to talk about like how was that shift from like making these cool designs and content to like running the business over the years. Sure. What I would say is like I guess the point maybe I would try to leave people with is

I'm not good at that. And that's okay because A, I had co-founders. So if I'm going to recommend anything, it's just like it's really hard to start a business by yourself. So have have co-founders. Like do it as a team.

Even though you're going to own less of the business, it's going to be a bigger pie. And like I think I had a lot of insecurity around the fact that I don't think I made a good transition to like this tactical executor to this, you know, I don't know what you want to call them, like a Jeff Bezos or like this theoretical CEO that we think about. And that's okay, right, because they're just strength and weaknesses. And it doesn't mean that if you're not able to make this sort of like epic transition and you act like a business school graduate who knows everything about leadership and blah, blah, blah. blah and team structure doesn't mean you can't build something that lasts and that people care about. But it does have to help to have other people there with you, obviously. And everyone doesn't have to be exceptional at the best thing. And so I think that was one of maybe the biggest

takeaways that I got from this. And hopefully that's like a nuanced take or maybe like a counterintuitive take that people listening to this, they're like, I don't know if I can make that transition. It's like, it's okay. Just be in your zone of genius. And once you get to a stage where, like, it just doesn't make sense for you to, like, learn things that you suck at. It makes more sense to just, like, keep doubling and tripling down, I think, on the things that you're, like, uniquely gifted to do. Yeah, yeah. I think I totally agree. Like, I say, you know, if you're not good at it, but you've got to then be willing to hire pay the money and find the good people to do it, right?

Like, that's the key. Whereas, I mean, a lot of entrepreneurs, they get stuck because they want to manage everything and they won't let it go. it's like, but then if you can't do those things, HR, finance, legal operations, you've got to let it go. And, you know, the whole rule of being a CEO is to hire people smarter than you in those areas, right? Totally. Totally. And I think the other thing that might stop entrepreneurs is, I don't, I can't afford X hundred thousand a year for this person. But that's the power of equity and investing into equity. It's not giving away 100% of your business, 50% of your business day one, right?

but those structures of just like not needing to put out a bunch of cash to get great people to help you build your business but that people invest into equity over four or five years right I mean I think that's a huge enabler and help self-select for the people who are in it for the long term but it does give you access to great talent to help you build something again where you own less of it but it's a much bigger pie yeah love that good so last few questions I want to ask you in the last few minutes a bit more personal about you as the entrepreneur like what what what is one or two or three lessons that you could teach your younger self or a younger entrepreneur that you learned through your entrepreneurial journey yeah so i think one maybe more

high level which is um why do we do this right i mean i think the and i hate to be so trite but like what i learned after the exit was like it is about the day to day it is about the journey it is about getting to work on something that makes people happy that's different right rather than this theoretical outcome that probably won't happen. We were very blessed that it did. But so just sort of that thing. And that I think is maybe the second thing. It's like the thing that kills these things is burnout, right?

Is giving up, is quitting. Because there's always a way. There are infinite paths to success, right? So I think the only way that you lose is by stopping. And I think the thing that keeps you from stopping is if we're just so focused on like this theoretical like whether it be a dollar amount or something, not that it's bad to have those sorts of goals, but when that's kind of the driver, I think it does increase the probability of burnout rather than like the input site. I'm with people I love doing something I love and I'm

making the world better in some way, right? I think that's like an infinite game that you can play forever. And I think the third thing would be tactically like just building a business. I just wish we continued to like in those first five years when we started growing, continue to just like invest in that brand building stuff, that organic content, you know, rather than just getting so focused on Like, I got to sell this product. I've got to hit this month's number. I got to do that. It's not bad to have that focus.

But when it becomes an overwhelming focus, right? It's good in the short term, but it gets really bad. Just trust me, it gets really bad. And so you got to, it leads to some troubles where if you stay balanced when you're building your brand or building your business, right, generate demand and capture demand. It sounds obvious, but it's way easier said than done, as you probably know. Yeah, I mean, it's that balance. Like, I'm a big paid ads guy.

I've been doing it 12, 15 years and spent hundreds of thousands a day. And it's always like, you know, as you scale, you want to have that CPA number and acquisition number and know your LTV. And to me, that's how you scale a business to a massive level is being able to do that and know those numbers. But then, you know, the background behind it, I always teach is the organic and the branding. And it all, they, they, people they say, Rudy, paid ads are organic. I'm like, it's like saying diet or exercise.

You know, they flow so hard together that you can't really do one. You can do one about the other, but you'll get very suboptimal results. So you have to be, have to be building both in the background. And I think that's so important, especially, you know, 10 years ago, we didn't really know how this world would look, but now everything's so brand-orientated and people are attracted to brands because of who they've become, you know, and what they represent, right? Totally.

100%. Good. So last question, Preston. Thank you so much. Where, if people want to follow along your journey, your new venture, maybe talk about it for the last minute, how do they find you and follow you? Yeah, totally. So, yeah, the thing I try to bring to the world that might be unique from others is like,

how can I actually measure the impact of brand building in a way where you can sort of like justify it to your CFO? So primarily speaking to sort of like digital marketers, digital advertisers, consumer brands primarily the B2B as well. So if you want to just listen to musings, mostly about mistakes that I made throughout Bill and Chubbies or being a part of and witnessing because the other founders were the ones who were doing most of the cool stuff and the team, of course. Preston Rutherford on LinkedIn and Twitter, and then the company that I'm working on right now to try to solve the problem of like this holy grail

of measuring brand or top of funnel or awareness building is called marathon datacow.com. Yeah, I mean, it's funny. So many people that have built big brands, they like, you know, want to be involved in data companies. Like I took equity in an LTV data tracking software and software tracking because you realize how key it is, right, and how much of a nightmare it is.

to pull it all together during. Oh, my gosh, to pull it all together. I'm excited. Oh, yeah. Yeah, yeah, yeah. No, thank you. But yeah, you're totally right. I mean, it's born out of dealing with the pain yourself as an operator and realizing this

really hasn't been solved. And so, well, we've probably spent tens of thousands of hours on Google Data Studios, just doing it ourselves and pulling and every, you know, zapping every and game because it's just, there's nothing. Yeah, just trying to build that modern data stack, patch it all together, get people to trust the data throughout the organization. I mean, you've dealt with this. But yeah, you've got this big problem that you deal with as an operator.

If someone else isn't fixing it, you've got to fix it yourself. It's what we're sitting out to do. Good. Well, I'm excited to check that out and follow along your journey. Thank you so much, guys. Everyone listening. Hope you enjoyed that, you know, session. And really, you know, I think it's the great entrepreneurial journey, right?

Cool idea. Group of friends got together, started this brand. And then it became, you know, globally recognized, obviously, big exit and success. and still has continued success. So great job to you, of course, and your co-founders. And it's been awesome to see the brand evolve since I moved to America, you know, fresh out from England. And one of the first pairs of shorts, I think I owned here in America.

And I've always, I always love, you know, Florida, so I love my palm trees. So you guys catered to me very well over the years. Yes, yes. Actually, actually, two of my grad school friends got pineapple and palm tree tattoos. they love so much really love that love yeah just live the tropical vacation life exactly so thank you so much guys that's a wrap as always keep living the red life work hard and i'll see you guys soon take care