The Black Sheep: Ben Goorin, CEO of Goorin Bros.

Ben Goorin is the fourth generation CEO of Goorin Brothers, the family hat company founded in 1895, and the creator of The Farm, the animal trucker hats worn on heads all over the world.

Ben and Darren met years ago in the same YPO forum, and he’s one of the truest creatives Darren has ever seen occupy the CEO seat. Ben’s company was founded the year hats peaked in America. Every year since has been a headwind. His father told him the business is what it is and would never be different. But Ben spent his career proving otherwise, interrupting the mundane, as he puts it, until one of those interruptions, a rooster hat with four small letters stitched beneath it, split the company’s history in two.

Ben and Darren explore what putting on a hat actually does to a person, the freedom and the price of leading without a playbook, and why Ben believes the moment for creators like him has finally arrived. 

Darren [00:00:00]:

Hi everyone. Welcome to another episode of One of One. I’m your host, Darren Gold, CEO of the Trium Group. My guest today is Ben Goorin, 4th generation CEO of Goran Brothers, the family hat company founded in 1895 and the creator of the Farm, the animal trucker hats worn on heads all over the world. Ben and I met years ago in the same YPO forum, and he’s one of the truest creatives I have ever seen occupy the CEO seat. His company was founded the year hats peaked in America. Every year since has been a headwind. His father told him the business is what it is and would never be different. But Ben spent his career proving otherwise, interrupting the mundane, as he puts it, until one of those interruptions, a rooster hat with 4 small letters stitched beneath it, split the company’s history in 2. In our conversation, we explore what putting on a hat actually does to a person, the freedom and the price of leading without a playbook, and why Ben believes the moment for creators like him has finally arrived. Please enjoy my wonderful conversation with Ben Goorin. 

 

Ben, it’s so good to see you and to be doing this together. And I want to that for people that are listening, we’re also live doing this by video. And what you can’t see if you’re listening, of course, is the fact that we’re rocking these incredible Goorin Brothers hats, the company that your family has been part of for over 100 years, and that you are now the CEO of. I can’t wait to get into a conversation with you ’cause we know each other as friends. I’ve witnessed you in your progression as a CEO, and I’m a huge, huge fan of your company and what it stands for and what the brand stands for. So, thanks for being here, first of all.

 

Ben [00:01:55]:

Thanks, Darren.

 

Darren [00:01:56]:

I know we’re gonna have a ton of fun.

 

Ben [00:01:57]:

Yes.

 

Darren [00:01:58]:

Let’s start maybe in the early part. You’ve been part of the company for most of your professional life, right? CEO for largely about 20 years. So, I want to take us back to maybe when you became CEO, maybe just before. And maybe let’s start with these Animal Farm hats, which I’m a big fan of, have several. I’m wearing the king one, the lion, right now. And maybe you could ask me about that, why. But it was your inspiration, and I’d love to understand the nature of that inspiration, where it came from, and to bring what I think is a pretty epic story to life, maybe starting at the beginning of that.

 

Ben [00:02:37]:

Yeah, love to. My favorite topic. From 1895 until around the year 2000, we followed a certain path. classic hats reinvented over the decades. But around 2000, things changed when we stumbled on our Animal Farm truckers. It was a little bit of an accident, and I like to say the company is divided into pre- and post— pre-cock and post-cock, because it was—

 

Darren [00:03:18]:

That’s a way to get the show going.

 

Ben [00:03:20]:

It was the cock, the rooster with a small font, C-O-C-K, that sparked the entire collection, which turned into really the core of the business.

 

Darren [00:03:37]:

There’s such an irreverence to that story, and I want to go into it a little deeper because you had some vision. I think it says something about you as a creative, as a unique creator as well, and a unique leader. So bring us back. What was the moment where you had this sort of like aha? I know there’s obviously, with everything innovative, there’s some luck, but there was some moment where you had an aha. What was it?

 

Ben [00:04:04]:

I have searched from the first day I joined the company for ways to interrupt the mundane. My father told me, the business is what it is. It’s never gonna be different. And for him, it was about survival. For him, it was about continuing a family business that his grandfather started in 1895. For me, I wanted to do something interesting, exciting, creative. And so I was constantly looking at ways to reinvent The business. And the invention of the Animal Farm collection, starting with the cock, was one of those interruptions. And this one just happened to work, and it happened to capture people. And not just people, but the right people. And the right people offered a feedback loop on what it is we need to be doing. And so that really started the evolvement of Animal Farm becoming the core of how our business pivoted.

 

Darren [00:05:19]:

And so you could have picked any animal.

 

Ben [00:05:22]:

Yeah.

 

Darren [00:05:22]:

You chose something that, you know, is provocative, evocative, a statement. Why that? And what did it tap into? There’s something that you and this line have tapped into that says something about both your brand, but a sort of fundamentally kind of human need, is my sense.

 

Ben [00:05:42]:

Yeah. So, you know, the cock, a classic rooster, again, with the small type, very understated, left room for interpretation. It wasn’t a loud statement in your face. And it was a way for people to be ironic, not easily figured out, and what we’ve learned and where we’ve focused on our consumer and the people that we are really here for are those that are looking for self-possession. And that means being comfortable in who they are. We just provide tools that allow them to amplify who they already are. And that’s what people are looking for. At least the people that we’re interested in serving are looking for ways To not only discover more of aspects of their identity that sometimes they keep hidden, aspects of their identity that they want to explore, ways for individuals to not necessarily tell the whole story and keep people guessing, but it becomes a tool for people to— own something that they’re in control of without having to say the whole story. And that juxtaposition of the rooster with the word cock does that. It creates curiosity. It allows somebody to, without having to say a word, to be noticed. And that’s really what people want. They don’t want to disappear into the sea of sameness. They want to be noticed. but they don’t necessarily want everybody to figure out who they are, because who they are is more than one thing. And that’s how the Animal Farm turned into not just the cock, but a whole series of animals that continue to mutate to this day as people get to explore and have fun with their personality.

 

Darren [00:07:59]:

Yeah. Yeah. There’s something also about the animal you and I have talked about in the past, and that’s different than some other symbol or some other image. What was it about the animal that you either recognized as being important at the outset or realized is important in retrospect?

 

Ben [00:08:15]:

I think people connect with animals in many ways, and I think that taking on characteristics and traits and personality of animals is easier than comparing themselves to other people or even themselves. So, I think when you eliminate all the noise and get outside of your normal routine and relationships, an animal allows you to transport into really another world where the rules are different. And the rules are based on instinct. The rules are based on prowess or confidence or special talents. And that’s how animals survive. It’s also how humans survive. I think that the animal is the most important way for people to feel like themselves without staring at themselves in the face and being exactly who they appear to be. So we’re continuing to learn and are super curious. And it’s really interesting to find more and more ways that people are connecting to animals and why, because that really is the way that we’re innovating, continuing to create not just new products, but really new worlds. And those worlds are really refreshing and, and offer people a way to step outside of their routine. And people need that. They need that break. And that’s really how our brand enables people not to fit into their day-to-day routines, but to actually give them an outlet, open up a new door of discovery. And it almost forces them to think about their own identity, because if you’re gonna wear something, put it on your head, obviously everybody can see it, you’re announcing something. You’re committing to something. And it’s up to you to decide what that is. And it’s really fascinating to watch. how something as simple as a hat actually does change a person’s outlook, how it gets them through their day, and how it really solidifies a lot of what their goals are. And we’re really interested in following that path.

 

Darren [00:11:01]:

Yeah, I want to pull on that thread a little bit more because you start a hat company in 1895. You’re on trend. You know, when you took over in the early 2000s, I’m not sure the same could be said. So, in some ways, you were— I wouldn’t say kind of swimming upstream, but you didn’t have a lot of wind at your back. And I think you’ve tapped into something here that is really, really powerful. And I want you to say just a little bit more around— about this sort of act of putting a hat on.

 

Ben [00:11:31]:

Yeah.

 

Darren [00:11:32]:

So, what does it do to a person? And then a sort of related question is, like, what is the— What is the purpose of this company? Because I think they’re probably related, if I were to guess.

 

Ben [00:11:42]:

Yeah. So back in 1895 was actually the year that hats peaked in America. From 1896 onward, it has been headwinds. The industry has shrunken every year, one year after the company’s founding. So Over the decades, people stopped wearing hats. It used to be mandatory. You didn’t walk outside without a hat on. If you did, people would stop and notice and point, and you would be the center of attention for not wearing a hat. Now it’s the opposite. So if, for the nonconformists, for those that are putting themselves out there, they’re making a statement in some way, Wearing a hat instantly, instantly does that. And so that’s how I found my footing with a company that was founded on wearing hats when everybody did, into a company where you were a nonconformist just by the act of wearing a hat. And we couldn’t just make any hats. We needed to put our own stamp. We needed to invent and reimagine how hats would be relevant for the creatives, the musicians, those that are independent, those that like to think for themselves, reinvent themselves. And so that path is what led us to all kinds of— innovative styles based on classic— there’s only so many hat shapes and blocks that are timeless, and people appreciated our expertise and authenticity, but we did our own recipes. We made our own twist. We created something new based on a tradition. And that need, that constant need for me personally, to twist, to create something new, to make things a little more exciting, interesting, led us to product innovation that was my passion. And the Animal Farm collection was just another example of that innovation, only this one stuck for a global audience. I hit on something with this that went beyond just some of the niche of people that were looking for a hat for some sort of nonconformity. This one actually opened up my eyes to the fact that everybody could use a break. Everyone can use an interruption. Everyone can use some exploration and discovery about their identity. And we did it in a fun way. We did it in a way that’s disarming. We did it in a way that doesn’t take yourself too seriously. And And we made it accessible because a trucker hat is something anybody can wear, right? You look great in this hat. Most people would walk into our hat shops, because at one time we had 36 hat shops across the country, and we always knew what they were going to say. They would say, I’m not a hat person. And I would tell our staff, our team, our— to ask the customer, well, what kind of a person are you? Are you not a hat person? Well, maybe— are you a pants person? Because it’s really the same thing, right? Like, why is it that you need to be a hat person to wear a hat? Well, there’s a stigma. There are certain people that wear hats and certain people that don’t. A baseball cap, a trucker cap, doesn’t make you a hat person. It has become universally acceptable. It has become part of the uniform. So we no longer had the friction. We no longer had to overcome the, of course you’re a hat person. Those questions weren’t asked anymore, ’cause everybody can wear a trucker hat. So now we can go deeper, and we can then talk about the particular identity, the badge. What do people want to represent? It doesn’t have to be who they are. Like, it doesn’t have to be that serious. It could just be their mood, how they like to play, that experimentation. And when we reach that level, removing the friction and really making it fun, really making it— easy to understand, and instantly rewarding, we realized that this transcends culture, age. This works everywhere in the world. And these hats started showing up across the world in all cultures. And that was really the, okay, we got something here where— there was an alignment in the business. And I think you call it market fit, right, in the textbooks. So that’s really when it changed. Everything changed. So that’s why I say the business— there was the business before the cock, and there’s the business after the cock. Yeah.

 

Darren [00:17:26]:

And it took a little while, right? So I think it was 2003 you launched. a good decade-plus before that moment of like, okay, we’ve got something that’s viral. Was there a particular moment, or what was the era where you’re like, wow, this is becoming something much bigger than even my wildest expectations would’ve imagined?

 

Ben [00:17:45]:

So, it was in Barcelona, Spain, when the hats that were always popular, right? And we had a following in Barcelona.

 

Darren [00:17:57]:

You had a store there, I think, right?

 

Ben [00:17:58]:

We worked— We had a lot of partner stores. And so there was a following, but the following turned into, I would say, chaos when very well-known European football players started wearing them.

 

Darren [00:18:17]:

And one in particular that might be—

 

Ben [00:18:18]:

Well, Lionel Messi. Yeah, yeah, yeah. So things erupted when that happened. And lots of other athletes also started wearing them. Prominent individuals, right? That— that were noticeable. And— and it spread. And that was really unexpected and organic. But I go back to, it’s because this is working for so many different people. And plenty of people, plenty of people wear them and discover them outside of Lionel Messi. And it’s still working. So— but that was really the time around 2009, 2010 that it took off to another level.

 

Darren [00:19:06]:

Yeah. I want to step back and talk a little bit about Ben the person, the person who brings the irreverence, the creativity, the provocation that turns a company into something quite different than it was before. I mean, puts it on the map, so to speak, and maybe redefines it for the next generation to lead, certainly. What were you like growing up? Were you always this creative? Were you always contrarian, unconventional?

 

Ben [00:19:39]:

Tell us a little bit. Yes.

 

Darren [00:19:40]:

Yes.

 

Ben [00:19:41]:

Yeah. I did not like routine. I did not like the same old thing. I did not like institutions. I did not like the school system. I always felt like I was on the outside looking in. I could always observe what was happening, and I was always very conscious of it. And I saw how most people sort of fall in line. They stay inside the borders, they follow the rules, and they play the game that everybody expects them to play. And I was never like that. It wasn’t to be defiant, right? It wasn’t because I was angry or mistreated. Just the opposite, right? I just have an imagination. I like things that are more interesting, that are not as obvious, that are more obscure, that are different, that can surprise. people. And that’s just, that’s just who I’ve always been. And that’s what I take to work every day since day one.

 

Darren [00:20:55]:

Yeah, I want to talk about what it’s like to be a creative, like true creative. So I’ve gotten to know you like a real creative, which is what I love about you, of the many things, and being a CEO with the kind of expectations and the conventional wisdom that comes along with with that role. And part of the reason why I started this show and why I was so excited to have you on it is the name itself, One of One, which is really a statement that every CEO is unique. And if we try to run a playbook, that’s when we usually get into trouble. So I’m wondering, I imagine you might have attempted to run a playbook, but you’re certainly not running a playbook. So bring us into that part of the story here.

 

Ben [00:21:37]:

It’s really the only way I know how to make this work, right, for me, is this was a mom-and-pop family business. I worked with both my parents in the early years. My father worked with his father, right? So, this wasn’t like, okay, I went to business school, and I want to start a company, and I’m going to follow a plan, right?

 

Darren [00:22:06]:

Right.

 

Ben [00:22:07]:

This, this was a mom-and-pop business that ran based on the individuals that were running it, right? And I had to figure out step by step, not only the creative part of the business, right? And the part that I enjoyed the most, which was on the developing the product and the stories. But all of the parts of a business that you can imagine are not sexy, that are operational, that are typical, right? That anybody could have, could have run that better than, than me. So what that means is a lot of people that might want to focus on only the creative part of the business would find a partner or a co-founder, or, you know, they would, they would find somebody to do the, say, the operations. I never found that. I looked for it. I made some hires. And I can’t tell you today if, if they were the wrong hires or if I was just not setting them up to succeed. But I can tell you that it never worked. And The business was a lot of trial and error to move the business along during these different phases, especially during these growth phases. And it was really at the seat of my pants. It was really about just trying things. And I have great employees. I have people that are very capable. But they’re not equity holders. They’re not strategic. They’re not entrepreneurs. And so it’s always been just me and people like yourself that I get to meet along the way and have these discussions with as thought partners that allow that more strategic side of me to develop and get feedback. And that’s, you know, why I think our relationship’s always been really important to me, is, is to learn from people like you. But that’s different than having a hired employee on salary. And so, I guess I’ve struggled a lot with aspects of the business, but I also feel like at least I didn’t turn it over to somebody that— I was not having fun with, right? So, you know, that’s the good part is I get to still do whatever the hell I want with this brand. And for me, it’s really about the enjoyment now more than anything. And I don’t know if I’d be in that position if there were partners or co-founders involved that wanted to go a different path.

 

Darren [00:25:11]:

Yeah, I want to come back to that because I think there’s something important there. And I want to just offer something, get your reaction to it, which is there seems to be something strikingly similar between the permission you’re giving your customers to take a little bit of personal risk, to express themselves, to be a little bit bigger in the world through that self-expression, and your own giving yourself permission over time to say, like, actually, I want to run the company the way I want to run the company, and that’s the only way I know how. Do you see that symmetry there?

 

Ben [00:25:43]:

I can’t separate it. The brand and what it projects for people and the way I see the business are mirrors of each other. So what I mean by that is our sort of brand archetype personality would be a black sheep, and a black sheep obviously stands out is the one of one. You like that? And the black sheep is something that so many people can relate to. Either they were a black sheep or they know a black sheep. Maybe it was a brother or an uncle, but it’s a good framework. And the black sheep just doesn’t fit into the rest of the herd, but it doesn’t mean that they are an outcast and should not allowed to be part of the herd. In fact, the black sheep is what’s really important for a herd, just like having individuals that see things differently are really important in society or in any organization. And so that’s really who we are, and that’s how I am naturally, and that’s how the business operates, and that’s how we project. to the people we serve that this isn’t the safe, normal way of fitting in and doing what everyone else is doing. This is a way to embrace the black sheep in all of us. And some people self-identify that way, and those are no-brainers in terms of customers, but many others need that relief. need that unwind, need that weekend, need that time away from the daily grind to find that black sheep energy and to be defiant in a way that’s not so consequential, right? It’s not like you have to go get your face tattooed or body piercing, right? Simply by wearing one of our trucker hats, You can feel head to toe that personification, that amplification of that inward identity that you want to take on. And that is something that is powerful, and that’s instant. And that is something I see time and time again. When people find their way into our hats, they really find that source of truth, irreverence, comedy, freedom, simply that act of going against the obvious. And the best way to surprise people is really to surprise yourself. And that’s what people discover with the brand, ways that they’ll surprise themselves. So, to me, it’s a whole journey that parallels how I have always run the business and how I think about things and how it transcends into our customers and how they interact with the brand.

 

Darren [00:28:57]:

Great. That really came to life for me. We often say the company is a perfect reflection of its CEO. You’re a case study in that. It’s wonderful to see. And I’m also curious because I think for people listening, they’ve probably got an image of what it feels like to work inside your organization and to work with you. Can you give us a little bit more fidelity there? Like, we probably have these images, but what does it feel like? What works? What’s the stand you’re taking inside the company for what the ideal should look like?

 

Ben [00:29:29]:

Well, that’s an ongoing challenge because the vision is clear to me, and where I fall short is articulating that vision in constructive ways that translate to other employees, where people want to sink their teeth into something. People want to know, well, what do I need to do? Tell me what I’m supposed to do. And already, that’s too much structure for me, right? Because this is about figuring it out. This is about creating a world that doesn’t exist. And if we have to operate in a world that does exist, It’s easy to get caught up, right, into logistics, into fulfillment, into inventory. Those are all places that are familiar to people. Those are all places that people have expected from their past experience how to perform and how they’re measured and what they’re supposed to be doing. Now, again, what they’re supposed to be doing, how it’s measured, this to me— holds people into a world that is far from the world that I see. And so that sort of jump or leap is the most difficult part of aligning an organization. And that is where I struggle, and I’m perfectly aware of it. But I don’t know how to go back. I don’t know how to— Hold back. I’m in it for, for our customers. I’m in it for the people that are ready to go down, take on that journey, and suspend disbelief. And people find ways of doing that with our brand and with our hats on their own. And this is something that I just need to get out of the way. Unfortunately, it’s tough to get out of the way of people that you’re supposed to be managing and leading in an organization.

 

Darren [00:31:39]:

Yeah. How have you given yourself permission to go all the way in terms of what— how you want to lead, or are there still places you’re holding back? Where are you on that journey?

 

Ben [00:31:53]:

Yeah, I think that there are moments and there are times where I don’t hold back, and then I’m often brought back into reality, right? And I think that that is the constant— both it’s sort of parallel to how I see a customer’s journey, right, where they can escape and have their moment and feel like they found their freedom, right? They found their self-confidence. They’re exactly who they want to be. And then the next morning comes, and they have to get back to work in their routine, and it’s lost. And sometimes I think about other ways of interrupting the mundane. And, you know, a hat is something that people can just keep with them as a constant reminder and put on and instantly connect with— their alter ego or just enhancing who they’ve always been. But just the act of wearing that statement is an internal reminder for people that I think does help.

 

Darren [00:33:07]:

Yeah, the fact that it’s mirroring your customer— your experience is mirroring your customer experience may be pointing to the fact that it’s exactly the way it’s supposed to be. We talked a little bit about paradox on our walk over here, and there is no freedom without being controlled.

 

Ben [00:33:21]:

Yeah.

 

Darren [00:33:22]:

You can’t experience freedom unless you have access to the opposite. And so, in some ways, your experience of, at times, being fully free to be expressed, to lead the way you want, and then being drawn back into a more controlled posture may be the only way. Yeah.

 

Ben [00:33:43]:

But if you think about animals, right, like, they’re doing the same thing, right? They have to have a controlled posture. posture or they’re going to be killed, right? And so exploring and understanding how other animals adapt and survive and camouflage are helpful. And again, this is the journey and the discovery that I really enjoy, and it’s never-ending. Like, people think, well, you’re going to run out of new ideas? Never. You’re going to run out of animals? Never. There’s mutations. There’s so many species. Just organizing the animal kingdom is a current project I’m doing, and it’s just fascinating. And I just think that the world needs a way to explore and discover and have fun. And, you know, businesses need to be creative today. And if you’re just doing the same thing over and over, I’m not sure you’re going to be around in 5, 10 years, right? I think there’s so much disruption, and I think that the consumer, if they’re going to spend real money with you, they need to get more out of it, right, than just something that they’re going to temporarily wear. They really need to believe in the story. And so there’s nothing but more creativity ahead, and this is what I enjoy.

 

Darren [00:35:07]:

Okay, so I want to ask about the technological paradigm we’re in and juxtapose the need for creativity? Because in some ways, a lot of people might see those as in conflict. I read a great article, an interview of Jimmy Iovine and Dr. Dre in The New York Times, and they were like, oh, no, like, our creativity is absolutely booming given AI and the tools that are becoming available. What’s that? What’s AI? It’s this thing. I don’t know if you’ve heard about it. So I’m just curious if what your experience is, how you think about technology and creativity coexisting?

 

Ben [00:35:44]:

If there’s ever a time for me to realize my vision, finally, it’s now. If you can think it, if you can imagine it, it can be built. And if you’re relying on things like a bunch of funding or making really good recruiting decisions or hiring really good managers or having different leads, across different functions of an organization. If that hurdle, especially for somebody like me where that doesn’t come naturally, has been the limitation, then there’s no excuse to realize the vision. You no longer need to hire an entire team to develop the gamification of what this brand is becoming. The experiences, whether they’re digital experiences, whether there are insights that can be constantly fed into like a feedback loop, right? Connecting and reaching people and having this feedback loop through all the tools available today. make this just an incredible time for me personally. And so, yeah, I’m really excited about this next phase.

 

Darren [00:37:09]:

Can you give us an example of an idea that you’re working on that’s sort of— and what the technology is helping you do from a creative standpoint?

 

Ben [00:37:18]:

So, the whole collectibles world, right, is exploding right now. And if you think about, like, Pokémon cards, for instance, There’s an entire framework built on the civilization, right, that comes with an experience like Pokémon. Well, it’s not unlike that, right? So, first doing the research and looking at all the different ways that collectibles, from sports cards to Magic: The Gathering, they’re all very insightful into creating a framework. And organizing our animal civilization by species, by relics, by scarcity, mutations is a big research project that I’m doing so that I can actually publish and document how our— not our products, right? But how our system has been released into the world, and that is going to become a new framework for how I think people are really going to enjoy interacting with the brand. So, certain animals have certain qualifications and certain levels of power, you know, superpowers, insight, capabilities, and, you know, you can give those animals a score. And in order to accomplish something that I call the tournament, you need a group of animals to come together in order to accomplish those things. Well, now that gives the community the opportunity to work together through this gamification in order to enter certain contests and to play in this world. So, That’s just a little bit of where I see the AI tools now available to be able to create that kind of gamification at a level that would require, you know, large teams of people in the past.

 

Darren [00:39:31]:

Yeah. I want to get into a little bit more of you as well here. And that’s given, I think, all of us some more insight into the workings of your mind. And I love the fact that, you know, most true creatives that I speak to are finding ways to amplify their creativity, their craft, which is such a— I think we’re living in such a promising time with all of the attendant potential risks and downsides, of course. If you had one animal to wear on your hat, what would it be and why? I just, I didn’t know I was gonna ask that question.

 

Ben [00:40:06]:

A platypus. I almost brought it. It says awkward. something very self-revealing, right? Where you’re the ego, right? There’s the posturing, you know, you’re wearing the king ’cause you’re posturing that. And that’s great. That’s a great first hat, Darren. Congratulations.

 

Darren [00:40:23]:

Thank you. Thank you.

 

Ben [00:40:24]:

But to actually explore personas that contradict your public face into something that maybe you internalize, is actually really, like, people really respect and like people for being truthful and honest, right? And being revealing. And I think that that’s what I think the brand can unlock at different levels along the way. If we have to act a certain way and posture and come across as knowledgeable, or we’re measuring ourselves by, you know, how many people we manage, or our title, or our incentive structure, right? And that becomes the measuring stick or the barometer. I like to think about how can that be disrupted, where really what people care about, human to human, is honesty, is Somebody that is self-possessed. And that means grounded in your own authority. And when you can choose deliberately, not needing constant approval, that’s how you grow as a person. That’s what leads to freedom, but it leads to loving yourself. It leads to courage. And other people notice that. And Other people actually really like you for that reason, because nobody really cares about the other things. Nobody really cares about, oh, they’ve, you know, hit a certain plateau and now they can afford this, that, and the other. Nobody cares. In fact, it kind of annoys people. And the fact that all it takes is courage, all it takes is to be honest and to reveal and to not take yourself so serious and to be a little creative and to discover yourself a little bit, if that’s all it takes, and you can wear that on top of your head, I mean, we’ve got something, right? And in that, call that like this spark of being alive and that instant gratification you get because people will comment, strangers will, might make a comment. It might be a conversation starter about your hat. In very subtle ways, you’re actually connecting in an honest way Because you’re not taking yourself so serious, meaning, this is what I want people to believe, this is how I want to control an image. But you’re revealing a side of you that’s playful, that’s curious, that’s unsure, that can be ironic, can be a contradiction. And that’s what life is.

 

Darren [00:43:24]:

And—

 

Ben [00:43:25]:

100%. You know, when people go home after working all day and they’re with— whether they’re with their kids, their family, their neighbors, it is so rewarding because they can be themselves, right? They can take off their work clothes, right? They can take off their work expression and how they speak, and they can be human. And we’re all the same, right? When you remove those things, you’re actually— we’re all the same. And that sameness allows for connection. And that’s what the world really needs right now is everyone needs to actually feel like they’re closer to each other than further apart. And that’s how I think the animal world feels. And I think that humans need to get back to that biology. And if we all know we’re all struggling with the same things, and we all just looking for connection and honesty and a little bit of fun and playfulness, A, we’re going to get along a lot better, but we’re going to enjoy living our lives a lot better. And, you know, that really gets into the world that I want to continue to create.

 

Darren [00:44:41]:

Amazing. I mean, in a 2 minutes, you’ve described, I think, the essence of your brand. I’m wondering, for those of you listening that are leaders of companies or responsible for building brand, how do you convey that? Because there’s a lot of nuance and richness in what you just shared, other than through the product itself, right? Which is the best way to communicate that? What are you doing to communicate that, if anything?

 

Ben [00:45:10]:

How am I communicating that to—

 

Darren [00:45:12]:

How does the company communicate the essence of what you just described?

 

Ben [00:45:17]:

So, that’s where I really have made a lot of progress around organizing this creation in ways that can come to life. So, right now, it’s been organizing them and communicating them through the products. Sometimes we’ll create experiences around it, but the effort for what I am going to really be immersed in is, is taking this further, right? And taking this all the way. And the only way to do that is to break from a lot of the traditional business metrics of needing to continue to do the same obvious things that other people are doing, meaning normal distribution, you know, create product that sells, move on to the next. Having more meaning, having, you know, doubling down on this commitment is something that I’m currently, like, really pushing.

 

Darren [00:46:24]:

How much does being part of a family-owned business give you the freedom to march to the beat of your own drum and be patient and make investments in ways that other people wouldn’t. I’m always curious about the role that structure plays in a CEO or founder’s freedom to build.

 

Ben [00:46:48]:

Yeah. I think it’s just more of because it’s in my DNA that I’ve always thought this way versus somebody that has worked For a company that had a lot of predetermined expectations, whether they’re trained for a certain role or measured against a certain role, you’re focused on fulfilling that aspect, right? Like, you’ve come in to grow sales, you’ve come in to build you know, this new process or this product. But I’ve always, because of my DNA coming from a family business where everything’s on the table, right? There’s no limit to what you touch or don’t touch, that it’s never about a role or what you’re supposed to be doing. It’s only about invention and reinvention. And so, yes, freedom, right? When there’s 100% freedom, you’re— you would think your hands aren’t tied. However, your hands are tied because you sometimes don’t have the benefit of knowing how to accomplish more complex things by not having those internal resources in place, it actually restricts you, right? And so, it’s sort of a two-edged sword. I’d rather take the freedom any day, but it does come with consequences where if you have to completely figure everything out, you’re really not that free because you’re— you struggle or you have to spend extra time doing things that probably should have been taken care of a lot sooner.

 

Darren [00:48:45]:

Yeah, that makes sense. So, we’re starting to turn the corner towards wrapping. I’m wondering if there’s anything that is on your mind we haven’t covered, or something we have you want to put a finer point on.

 

Ben [00:48:58]:

Yeah. I could just sort of say kind of the emotional part of the brand and talk a little bit about that. We often label ourselves, right? We— We self-identify into roles— husband, father, your position at work. And I think that that framework often limits us, ’cause there’s a part of all of us that doesn’t fit into a category. And I call that the irrational part. It’s a playful part. And that’s the part where you can be awkward, you can laugh at the wrong moment, right? You’re not— you don’t need to follow a script. And it’s really hard to— Summarize that inherent part that we all exhibit that isn’t always allowed to come out and play, right? And you look at children, and often it’s out all the time, right? And if we can go back to that time in our lives, you know, that’s probably the easiest way to think about this. But it’s that spark where you really feel at ease and happy and really enjoying who you are the most. That spark includes flaws that, instead of trying to correct them, look at them as evidence that you’re alive. And the brand, Goran, exists to protect it. And I think you’re constantly fighting an uphill battle when you’re trying to correct things that you see as flaws. Because they’re never-ending. But if you look at them not as flaws, look at them as things that you’re not supposed to correct, look at them in ways that make you human and alive, and don’t take yourself so seriously, you know, that’s when you’re really aligned with the purpose of the brand.

 

Darren [00:51:01]:

Yeah, I think the reason why we’ve become friends is because I saw that quality in you immediately. Right? Just for those of you wondering how Ben and I met, we were both in the same forum of YPO, Young Presidents Organization, a group of CEOs that would get together and learn from each other and build community. And that was so apparent to me, you know, and it was what attracted me to you. I was like, wow, that is somebody really not afraid to bring those parts and put them on the table for all of us to see. And so in some ways, it is the thing that connects one to somebody else when you’re willing to do that, right? Per our earlier conversation about what’s the more vulnerable hat that you would wear. And by the way, my answer to that might be shy. So I don’t know. I don’t think you have a shy— do you have a shy animal in your life?

 

Ben [00:51:53]:

I’m going to have to make you one. Absolutely.

 

Darren [00:51:57]:

You know, because there is a part of me that is quite sensitive and quite shy. And that would probably be the more revealing hat for me to wear. So, yeah, if you want to make that, I would proudly wear it.

 

Ben [00:52:09]:

Yeah. And that’s exactly right. It’s being able to be obscure, dance around things, explore things, put it out there, express it in ways that are very harmless. Because when— if you’re going to go and you’re going to meet people and you’re going to say, hi, I’m Darren, I’m shy, I’m not sure that’s exactly how you want it to come across, but when you are wearing one of our trucker hats that are based in irony, that keeps people guessing, that reveals things without saying the whole story, it’s an invitation, right, to explore in ways that are harmless. And it’s just a constant self-reminder for yourself, and it’ll spark conversations that— you can reveal or not reveal and keep people guessing. And that’s really what it’s about, making it really easy and accessible for people to explore parts of themselves that have always existed, and we just help to bring it out or to amplify it. But people come already with the equation. We’re just connecting the dots a little bit and turning it into an image, a meme, a saying, and giving people a, you know, the opportunity to wear it on top of their head, which signifies and announces a part of themselves because it is the most noticeable part of anything you can possibly wear. When you walk into a room, whatever you’re wearing on top of your head, you are—

 

Darren [00:53:50]:

You are…

 

Ben [00:53:52]:

going to make it known to anybody that this is something that you might want to notice. And I think that that sort of work and courage to get there is part of the journey and part of why I think we’ve seen this work for so many people across, you know, really all over the world.

 

Darren [00:54:15]:

Yeah. I was going to ask you, like, a— a lesson or a message you wanted to give to people, but I want to just assert what I’ve heard, because I think this is the message loud and clear, which is sort of a masterclass in how to connect brand and purpose within a company. I think you’ve given us an incredible lesson for what that looks like. So I think for people listening who are— want to build a purpose or mission-driven company, want to build a brand that conveys something much deeper, that’s deeply human, I think you’ve offered something really special, as well as—

 

Ben [00:54:47]:

Thank you.

 

Darren [00:54:49]:

What does it look to live and lead in a way that’s congruent with what you’re putting out into the world? So thank you for that. It was an extraordinary conversation and so much fun to be doing this with you, Ben.

 

Ben [00:55:02]:

It’s a lot of fun, and I’m already thinking about what that shy hat is going to look like.

 

Darren [00:55:08]:

Okay, well, we’ll post a picture of that if and when that happens. But it’s been great. Thanks so much.

 

Ben [00:55:15]:

I’ve enjoyed it. Thanks, Darren.

 

Darren [00:55:16]:

Likewise. 

 

What a wonderful conversation. Most of us work hard to disappear into what Ben calls the sea of sameness, sanding down the playful, irreverent, irrational parts that don’t fit the roles we’ve taken on. Ben’s whole life is a bet in the other direction, including how he leads as CEO. His message: the part of yourself you’re most reluctant to wear on your your head is probably the one most worth putting on is one that will stay with me. I look forward to being with you on the next episode of One of One. Until then, I hope you live and lead with courage, wisdom, and above all, with love.