The Modern Hotelier #248: From Pro Snowboarder to Hospitality Innovator | with Bradley Steward
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David Millili: Steve, who do we have on the program today? 
Steve Carran: Yeah, David, excited about today's conversation we have on Bradley Steward, the Co-founder and President of Caravan Outpost. Thanks for joining us, Brad. How you doing today? 
Bradley Steward: I am doing great. It's a beautiful day in Ojai, California here where I live, and I'm feeling good. Thank you. 
David Millili: Alright, Brad, so we're gonna jump in. We're gonna go through a quick lightning round, get to know you better, and then dive into some industry topics. Sound good? 
Bradley Steward: You got it. 
David Millili: All right. What did you want to be when you were growing up? Growing up? 
Bradley Steward: Professional skateboarder. 
David Millili: That's good. Alright. What's something you wish you were better at? 
Bradley Steward: Nearly everything. I would love to be able to paint. I would love to be able to paint better. 
David Millili: All right, good. What's a luxury you can't live without? 
Bradley Steward: Beautiful light. I have to say I'm tuned into beautiful light. I like spaces that are beautifully lit.
David Millili: Who's a person dead or alive that you'd like to take to lunch? 
Bradley Steward: Probably, Leonardo da Vinci, which I'm sure a lot of people say, but I'd love a quick chat with him. 
David Millili: That's great. Alright. If you could have a superpower, what superpower would you like to have? 
Bradley Steward: I would like to be able to run at about 120 miles an hour.
David Millili: Oof. 
Bradley Steward: And not have to get into a car or a bike or anything. I would just like to run everywhere. 
David Millili: All right. That's good. All right. Last one. What's something that's on your bucket list? 
Bradley Steward: Something that's on my bucket list is couple of weeks in Portugal. Learning how to surf big waves in Nazare. 
Steve Carran: Wow. That's a great bucket list. I was in Portugal a couple years ago and it was, it's a great spot, great spot. 
Bradley Steward: I got the guys to teach me. I just don't know if I have the courage. 
Steve Carran: And there's some big waves there. Big waves, yeah. 
Bradley Steward: Two big components. Courage and skill. 
Steve Carran: Exactly. Exactly. Well, that was great. Now we're gonna learn a little bit more about back your background and how you got to where you are. So, you grew up in Flagstaff, Arizona. Is that correct? 
Bradley Steward: Yeah, I did. We kind of lived between Flagstaff and the Verde Valley, which sort of encompasses Sedona and Jerome and all those cool little towns. 
Steve Carran: Yeah, sure. So how did growing up around Flagstaff shape you into who you are today? 
Bradley Steward: Well, I loved it. And I haven't lived in Flagstaff for many, many years. My family moved away from there when I was in my mid twenties, but I was born and raised there. One of the, one of the few people born and raised there at that time actually. And actually I would say Flagstaff really shaped most of who I am in a way because as a kid I was a skateboarder and always skateboarding around town, probably the only kid doing it at that time it wasn't cool or hip. 
Steve Carran: Yeah. 
Bradley Steward: And then it would snow and I started thinking about, well, I wanna be able to skateboard on the snow. And that led me into my whole career in, in snowboarding and that whole time there. So it shaped a lot of who I am and it taught me to appreciate the outdoors and center my life around that.
David Millili: So you went to Northern Arizona University and you got your degree in film and communication. What made you decide to choose those majors? 
Bradley Steward: Well, aside from being a, you know, you asked me earlier in the lightning round, what did I want to be when I grew up, I wanted to be a skateboarder and a movie maker. I didn't really have a long-term plan. I think I didn't really ask myself what would happen after 35 or 40 years old. Right. But I went to NAU, my mom worked NAU. I also went to the Brooks Institute for a while and was in film school there. And I was just always interested in media and communicating with people and writing stories.
I would say that that storytelling piece is what sort of drove me into film school. I wanted to, I felt I'd lived a little bit of a unique experience. In Flagstaff being on the edge of the Indian reservation and you know, kind of growing up in an interesting era there. And I kind of thought I would like to tell this story and other stories at some point.
Steve Carran: So you mentioned you were into skateboarding and snowboarding and you actually became a professional snowboarder. In the early days when the sport was still evolving and you know, on the hill snowboarders were kind of the rebels on the hill with the skiers, and you helped shape this whole industry. And as somebody who snowboarded when they were younger, I was really captivated by this. Can you share a little bit more about what it was, what snowboarding was like when you were a professional, and also how you almost changed the sport and where it is today? 
Bradley Steward: Yeah, a lot of people did a lot to develop snowboarding and I was really lucky to be one of the people at really what I think was the golden age of the sport in a way. It's like I tell my kids, you know, there was a time where I was ranked the number 13 snowboarder in the world. I leave out. The part telling them. There were only 14 of us riding at that time, and uh, so it makes them think I was, uh, better than I was. But yeah, I was a pro snowboarder for a long time, really in the early days of snowboarding, when we were just kind of figuring out what is this sport?
We saw it as a culture, more than a sport at that time. And it was kind of centered around, loosely around, uh, punk rock and then later kind of the hip hop scene and, and all about being who you are and kind of this we used to joke a lot about having a one track mind where you were, you know, really focused on just that single track and snowboarding and kind of staying inside the culture in that way.
And so I enjoyed my time there, Jake Burton and I created many of the first organizations in snowboarding. I think one of the fun and interesting pieces of the backstory is Jake and I actually sued the ski team, the US ski team at some stage, and we sued them because they wanted to bring snowboarding into the Olympics finally. But they wanted to bring it in like ice skating where there would be kind of five or 10 tricks that everybody would do and you would be evaluated and scored on those tricks. And, you know, Jake and I had created most of the contest, or had funded most of the writers in the contest for the first chapter of snowboarding.
And we kinda said, Hey, it's not gonna happen like this. We want snowboarding to be creative. We wanna keep it loose. We wanna keep the athletes in power. So we launched a lawsuit that led to the creation of what became the pro tour for the us, which is more or less still running today and the way you qualify to get into the Olympics.
Steve Carran: That's incredible. What was that process like as far as getting it into the Olympics? Was it diff, I'm assuming it wasn't easy to do but it's gotta help when you have the fire power of Mr. Burton behind you as well? 
Bradley Steward: Yeah, we had at that time, Burton was the number one snowboarding company in the world. I was part owner of the number two snowboard company in the world at that time. So we had a good chunk of the industry, a good chunk of the business, you know, behind us. And then, as I said, many, many other people helped. There were key people in Europe. Who had organizations and who had brands who were pushing from their end.
And really all we were trying to do is we were just trying to preserve that cultural side of the sport, which was all about art, design, music, and everything that I said earlier. We just didn't want the Olympics to wipe that out. We knew the Olympics would eventually come to us. When I started snowboarding, the first contest I went to, I think there were 67 people there, and then within a 10 year period of that, there was 12 million people snowboarding.
So it was a rocket ship and we were kind of advantaged in that we didn't know. Even what we didn't know. Right. And I always say that when passion is your playbook, you're probably in the right zone. And that's really where we were, our only playbook was be passionate.
We didn't know the metrics, we didn't know the KPIs. We didn't know how to accomplish it. None of us outside of Jake actually had ever formed really a successful business of any kind. And so, we were kind of a bunch of kids trying to shove this thing to the top of the mountain and then protected a little bit.
Steve Carran: Sean White coming through, that's who I grew up on, like Sean White, the flying tomato. You know what, watching him X Games do snowboarding and then he did skateboarding as well. Like actually incredible. What heki was,  I guess as you view it, like one of the people who almost took snowboarding to another level, Sean played a critical.
Bradley Steward: Role in the next step of the Olympic development? Jake Burton and I went to Nagano and participated in the first Olympics. And what happened there was kind of a little bit of a disappointment in the sense that none of the facilities were that well built for snowboarding. And it was clear that a lot of people who had managed the sport in that first Olympics had no idea actually what the sport was a kid who was a great snowboarder from Switzerland won the event, but he was someone who had never won a significant event before. He was kind of an outsider a little bit to the mainstream of what I would call the international elite people who were regularly on the podium. 
Steve Carran: Yeah. 
Bradley Steward: So you had kind of a fluky winner, which makes actually a great Olympic story that anybody from any little town anywhere in the world can show up and win, that's a big part of the appeal, but it wasn't a star. He wasn't a star, that we could really kind of put the sport on the back of that person and grow it, you know, and I always think the analogy of basketball is great. You know, the NBA was sort of benign until you had Larry Bird and Magic Johnson and people like that stepping up and really making the sport churn Sean White. My wife and I owned part of the world's largest snowboard camp at that time, which was a camp called Windells. Sean showed up on the doorstep of camp at eight years old. 
Steve Carran: Oh, wow. 
Bradley Steward: And started riding started riding the pipe. We immediately saw. This is the next generation developing right before our eyes. And I think what Sean really did was a service to the industry because he really brought it to the podium. He created real authentic stories. Sean, I think is a, is a good role model for so many kids. He's super focused. He really kind of gave us a vehicle to, to put the sport through where you, you could watch the Olympics and maybe you're not a snowboarder and maybe you don't understand anything about the sport, but you, but you do understand there's an exceptional athlete and you're gonna watch it. You're gonna watch it, you're gonna be tuned into it. And Sean really, really gave the world that, and I think he deserves a ton of credit for that, frankly. 
Steve Carran: So Brad, now moving on to your career, how you became the founder and or co-founder and president of Caravan Outpost. So you got into snowboarding. You're a pro snowboard snowboarder. You worked for Sims in 1989 and became their marketing director by 1990. Then you moved to a newly found Marrow snowboards in Salem, Oregon to co-own the company and serve as vice president marrow Snowboards eventually sold to what became two, and from there you started your own company, a bonfire think take design, which became bonfire snowboarding. Can you walk us through this time of your career and kind of how you decided to start your own company with bonfire snowboarding? 
Bradley Steward: Yeah, and kind of the quick runup is I had been a team writer for Burton. I'd met Jake when he and his girlfriend came and visited me when they were about well, when I was about 14. Jake is about 10 to 15 years older than me. And so I had ridden for Burton for a while at the very beginning of the Burton Company. Literally I think the first couple of years of it being in existence. Wow. And then I switched over to Sim Snowboards because I was more of a half pipe jumping guy in my snowboarding career, and the Burton Boards at that time could not ride backwards.
They had a specific part of their design, which prevented you from riding backwards, which of course if you watch the Olympics today, well over half of the tricks are done. What's called either Fakey or Switch, which means they're written backwards. And on the writers today, you can't even tell their natural way of writing. I went to Sims. I had a team writer Rob Morrow was his name, and Rob Morrow and I formed a company after being at Sims for a few years. We formed Moro Snowboards that was sold to the K two and Jarden group, and then I started Bonfire off of the back of that. My idea with Bonfire, and the reason I called it Bonfire Think Tank, is I thought, you know, I just kind of wanna create a space where you can think freely about sports.
I feel, uh, or I felt at that time I saw a lot of things changing. A big part of what I did was help to bring snowboarding to MTV, some of the early episodes of MTV Sports and, and everything that had happened with the Top 20 countdown and everything. That was really a, a lot of my work. I felt snowboarding belonged on MTV.
I lived in the Northwest, grunge was exploding. We had every famous band member you can think of the grunge era. We had every famous one of them, either in our office or on the mountain. So I really thought, you know, you need a space to kind of think about art, music, sport, culture. How does this all come together? And so I created, you know, the bonfire think tank and we worked on a variety of projects. You know, anything that would really come our way. We were a little bit like a production company and design house that had deep snowboarding roots, and then we launched our apparel line bonfire eventually became the second largest snowboard apparel brand in the world. And then I sold it to Solomon Sports. And then Adidas. Adidas came in and bought Bonfire and everything from us a few years later. 
David Millili: So in 1999, you dove into film. You ended up working at the Cartoon Network. You helped direct an early creative concept that helped kick off Adult Swim. How did you get into film at that time and how did you end up at the Cartoon Network?
Bradley Steward: Yeah, this was a wonderful, wonderful era. I had my film degree, it's kind of funny, part of the way I ended up working at Sims is I had been beaten badly in a contest, which was the national championships. And in particular, I'd been beaten by a rider who was a lot younger than me and I thought, well, that's it.
My pro career is over. I'm never gonna be as good as he is. And so I came to Simpson. I said, Hey, I've finished my education.  I have my degree. I'm gonna go write and make movies. You know, for the memories. This has been super. And they said, well, you know, hang on a minute. We would actually like to make snowboard movies. Do you want a job? Do you wanna make snowboard movies? And I said, yeah, sure. I'd love to try that. And so I started making snowboard films at Sims and you know, really literally traveling the world and, shooting everywhere. And then a couple of things were brewing that were really interesting.
We had a guy who was kind of a secretary in our office and he said, Hey, me and my friends are kind of dressing up and doing crazy stuff and, and shooting these videos of it. We kind of have this idea that we could do this thing called Jackass, which would be a TV show for MTV and that was I always joke with him that he was my secretary, my secretary, Dave England. But Dave worked for me for a number of years and I got to see Dave's career kind of develop. And of course, you know, jackass exploded and Dan quit and which I would've probably done at that time too. I was directing films and I thought, well, I'm gonna make a commercial for bonfire, just for the for kicks.
I made a commercial, it won an ADDIE award in advertising purely by luck, to be honest. I had no idea really what I was doing, but it was a really funny commercial called The Sniffer. And I had this character that was this guy that loves smelling things and he was in love with smells, and the commercial was about how much he hated our products because they don't smell and because we had a special venting system in all of our products at that time.
So it was kind of a quirky premise that it took off. As I said, it won the Adie. A producer at Cartoon Network reached out to me and said, have you ever shot. Kid commercials at all. And I said, no, but sign me. Sign me up. And he said, do you know who the Powerpuff girls are? I said, yeah, I have three daughters. I'm living and breathing Mojo jojo. And I went and shot a series of Powerpuff girl commercials that again, ended up to be kind of a right time, right place Powerpuff girls, exploded, I think off of the back of the group of commercials that I did, they sold over $300 million worth of merchandise, I think in under five or six days.
It was phenomenal. So those went really well. And then they said, well, what other cartoons do you like around here? I said, well, I love Space Ghost, they said, well, what, what do you have for Space Ghost? What would you do with Space Ghost? I said, you know, I was in line at the DMV the other day waiting, and I always thought it would be funny just to dress up in a costume, and stand in line at DMV, you know, and just see if you could get through the line quicker or dress up like a hotdog or Batman or whatever your Halloween costume is.
And so they said, well, okay, we'll let you shoot a commercial with Space Ghost at the DMV. So I shot a commercial with Space Ghost at the DMV and that was when Space Ghost was really emerging and I had a little bit of a specialty of doing live action plus animation as a director. And so I had an animated space ghost in line with all of these real people dressed in superhero commercials. So that went over really well. And then kind of the last piece is they said, well, we're beginning to think that people are watching cartoons at night whatever else they're doing, sitting around with the munchies and then, you know, at their college dorm. But we know a big part of our audience is watching cartoons at night. Do you have any ideas? And so, myself and a guy named Matt Pacini and a guy named Art Haney, we concepted a group of films called Escalator Danger Squad. Which was a pilot for what later became the adult swim piece of what Cartoon Network did Escalator Danger Squad was about these three guys who just guard escalators and they had all of these random things happen to them. 
Steve Carran: Oh my goodness. You're bringing me back to my childhood. Dave England Jackass Adult Swim. Aqua Teen Hunger Force was my personal favorite of Adult Swim. So didn't you go like skiing or snowboarding in Russia with Dave England as well? I thought I read that story somewhere. 
Bradley Steward: Yeah, I've done two trips to Russia. The first trip that I did turns out to be a really seminal moment in snowboarding. Actually a little bit myself, a guy named Craig Kelly and a group of people from a magazine. It was really the only snowboard magazine at that time, which was called ISMA group of us went to. Soviet, Georgia, what was then Soviet, Georgia in the, uh, late eighties. And we rode in the caucus mountain range above a place called Guari. And our original plan was we were gonna go from the World Cup in Switzerland, in St. Maritz. We were gonna go from the World Cup there, and we had this amazing heli trip planned in Russia. We were going to be the first snowboarders that were snowboarding, the caucuses, so we got everything together. The day before we left, we got a fax at our hotel in St. Maritz's at the World Cup and uh, we get a fax and the fax says, Hey guys, you have to cancel your trip.
Our helicopter crashed today and everybody passed away in the crash. We have no helicopter. And they were using old Russian troop transport helicopters. So we kind of looked at it and we said, forget it. We're, we're going anyways. The State Department had told us not to go. We had figured out a workaround, which was to fly through Vienna, Austria, and then jump on an aero flight from Vienna. And we had heard that you could, you know, slip the guy at the customs window, a little bit of money, and they would let you into Russia. So we did that and I hope my kids aren't listening and, uh, so, so we kind of bribed our way onto an flight out of Vienna. We landed in Tbilisi. We had a crew of people that came and picked us up, who we told from the hotel that we were coming.
We went there and we hiked and hiked, and hiked for days. And what kind of made that special was eventually we did get into a helicopter, but only to evacuate us, the Chechens and the locals were beginning to start a war together. We were snowboarding and you could hear gunfire and bombs 60 to 70 miles away.
And they said, we gotta get you guys outta here. The State Department had figured out where we were eventually. And uh, so we rode some Russian troop transport helicopters down to Tbilisi. Craig Kelly, who was with me on that trip, Craig Kelly was the four-time world champion in snowboarding, one of the best ever of all, all divisions, the best ever.
And there's a wonderful new novel that has been written about his life by an author Eric Blem called The Darkest Night. And Craig, it would've been the equivalent of Michael Jordan passing away in his prime. Craig eventually passed away in an avalanche, but he was a great friend and we had a great, great adventure over there.
Trip number two to Russia with Dave England was funny and weird because Dave's, especially at that age of quite an unpredictable guy and, uh, and, uh, so we were in St. Petersburg. For that trip and all of the mountains around a little town called Mineral, and we had a blast.
We eventually ended up in a place called Ette. And this is almost an unbelievable story, but at that time, Boris Yeltsin was visiting the re the region and his car became stuck. We had a very large snow storm and we actually pushed his car out of the ditch with a bunch of Russian guys because we were walking around the street and it was incredible. But, you know, again, that whole era was just, even as I tell you these stories today, there, it was kind of an unbelievable era to live through, you know, and be part of. It was really, really special actually. 
Steve Carran: Oh, I bet, I bet, I bet, man. I could talk snowboarding with you all day. So now let's get to the hospitality side. So after Cartoon Network, you actually, sold Bonfire Yes. And worked with Amme Sports. And you helped manage your own $3 billion of snowboard equipment and clothing in the United States, but then in 2015. You start a caravan outpost with your wife, what made you decide to get into hospitality and start caravan outpost?
Bradley Steward: Yeah. Let me clean up a few numbers real quick. Go Amer is around a 4 billion Euro company and I was a president of one of the divisions there, which was all of our action sports products and snowboarding. And Amer is a well-known brand, especially today because they're doing very, very well.
Amer owns Arc TerraX, they own Solomon, they own Wilson Sporting Goods and, and many, many other large sports brands. And so I was a president of a division for them. Y you know, my, my love of snowboarding never, never waned at all, but I felt like I'd checked a lot of boxes in snowboarding, and so I really, I really wanted to do more in the larger sporting goods business, the larger sphere of outdoor. And so that was really the impetus to sell my company to Solomon and then onto Adidas. And I had a real, you know, closeup. Look at, at ultra large business. You know, Deida at that time, I think was sitting in the 30 to 40. 
I think, yeah, 30 to 40 billion dollar range. So these were massive businesses with thousands of people working. So it was fascinating. I began a project for our mayor. They asked me, they said, Hey, will you kind of get off of the day-to-day track? And we would like you and a couple of people to begin concepting business for us, a new company, and there's only a couple of constraints number one is we can't go out and just buy another brand constraint.
Number two is, it kind of needs to come from the DNA of what we already have here as a company. And so I began a project kind of looking around at, well, what would the future of the outdoors look like if we're gonna be a billion dollar brand? And we've gotta look ahead, what? What's gonna happen 10 years from now?
I hired an agency called Frog. Frog is well known as the company that designed the mouse with Microsoft. And they were kind of a design and cultural agency with, uh, offices everywhere in the world and Frog. And I began this process of just traveling and talking to consumers. What do you think you're gonna do in the outdoors 10 years from now? What's important to you and why? Why would you be out there and what we learned is re a, a really simple lesson. We saw a massive trend in younger consumers, which was super, super simple. What they own will be less important than where they've been. 
And I was obsessed by that thought. I thought, you know, my whole life is a series of, of where I have been and these experiences. I can't tell you anything about the financial piece of any, you know, there's nothing, you know, financially that I've found particularly outstanding or, or, or rewarding. I could go on and on and on about sitting in a hut in the middle of the forest in Russia, eating food, you know, with the locals and having somebody, you know, bauska, you know, open a homemade dish and have us all eat it that was really meaningful to me. And so I kind of started to think a lot about, well, I wanna move, I wanna move into making experiences. I wanna stop making products. My wife and I are both designers. My wife designed at Bonfire as our head of design. She designed it. Patagonia as a color specialist she had designed at Solomon, she'd worked with Nike, some, and Columbia sportswear many, many, many brands.
And we were constantly fighting the idea in our head of, you know, we're putting a lot of plastic into the world and we'd rather not do that. All all of these Gore-Tex membranes we're using and everything there. There's many, many, many environmental and health implications from some of these products at that time, and we'd like to do something a little bit different.
So we began kind of concepting, well, how can we build an experience and I think really the thing that we did that was a little unique is, is we really looked at the experience as a product. We never really talked about building a hotel. We, we were always trying to build a product and we kind of productized it, if you will, in the way that product designers would, and that's what I think kind of gave us that, that that little bit of a difference.
You know, we always looked at the outposts. And we said, well let's try to build a prototype for what could be a bigger, a bigger business. Let's build a prototype. We have a saying in our family, which is nail it, then scale it. So we thought, let's go see if we can nail it on a teeny little business and then let's try to get it scaled up and get it big. And what we learned is people started coming to the outpost. I'll never forget, one of our first guests said, you know. When I'm here, I feel like I'm kind of living inside of a brand and we thought, bingo. That's what we were trying to do. We've actually got a couple of sound bites around what we wanted to do. So that was the move that, that we tried to make. We just tried to capture that audience that wanted to do things more than buy stuff, and we felt the outpost could be, could be their place. 
David Millili: We talk to a lot of we tend to focus more on independent hotels. For those who aren't familiar with Outpost, tell 'em more 'cause your property is very, very unique. So tell 'em a little bit more what it's like actually being at the property. 
Bradley Steward: Yeah. Well, I think we go kind of down in history as probably one of the first couple of glamping operations in America. We never used the word glamping. We don't see it as glamping, but many of our guests show up and they go, oh, I'm gonna glamp. And so the property itself is a little bit over a half an acre. It's a botanical garden. We believed massively in the power of having greenery around you. And one of our really simple design rules is, is anywhere you can bring the outside in. Do it and so most of the space is actually an outdoor living space and we kind of began concepting it, thinking, well, it could be like a living room that was in the outdoors.
It could be a kind of a sacred space kind of feel. And then we combined it with a couple of really important things, which I think was an entire retail store with a collection that my wife had designed with all sorts of branded merchandise that was from Caravan Outpost. And you could buy anything from a six to $700 custom hat. All the way down to a little teeny knickknack sticker dresses and things like this. And what really got us going is we had celebrities like pink and people like this who would show up and they would say, well, you know, I love the space. It feels good. It's kind of shaped like a horseshoe. We like the idea of sort of pushing people to the middle a little bit from kind of a place building standpoint.
And so kind of everybody's in, in sort of the same little spot for a minute. And we would have guests like Pink come and sit at our fire pit, play music, talk to guests. People would have no idea who she is, you know, and they would say, Hey, I met a girl named Alicia, Alicia by the fire pit, and she was talking about her show in Turkey. I'm starting to think she might be pink. Can you guys tell me what's going on here? You know, which we would laugh at but, you know, pink would buy our dresses and start wearing our dresses celebrities started seeing the apparel line a little bit and that that really helped us out, you know, quite, quite a lot and we're still a very popular celebrity hotspot because even though we're downtown, we're totally off the beaten path of downtown. You can jump on a bicycle and ride to town in two minutes to be in the middle of town, but we're off not on the main drag kind of outta sight. And so we have a lot of celebrity families that come and experience the space and they like it because it's private and kind of low key in a way, you know?
Steve Carran: That's great. So now we're gonna get into the industry thought part of the podcast. Can talk about hospitality on a little bit more of a deeper level. So I love what you talk about. You almost have built a community with caravan outposts and how it is designed with the 10 Airstreams and you also have one tiny house. How did you design it to create a better sense of community? 
Bradley Steward: Yeah. The idea was kind of hub and spoke, and we also thought a lot about what's the brain of the business, and again, these are just things that, you know, now that we've been in the hotel business for over 10 years now. And I talked to other operators, other designers, investors and so on, in the hospitality space. I learned that, you know, there's a tremendous power in not knowing how to do this. And 10 years ago we had no idea. And, and you know, for me, I always know the best snow is on the clear slopes where there's no tracks.
And so to me it was just, well, we're just doing that in business. We're just finding some fresh snow where there's no tracks and we're going down. The risk is there's a cliff or a rock and you, and you hit it. And, and I've done both in, in snowboarding and in business, and I've hit a few rocks in the powder that I didn't see coming, you know, so what we tried to do was just create this space that had a hub. We felt the most important thing to have with our guests was an emotional connection. And you know, when I would go to other hospitality events and stuff. I would hear people talking about, well, you gotta have amenities.
And I thought to myself that I get it. I like amenities like everybody else. You know, I wanna be able to open a o open a bottle of wine from the bed with my toes, uh, if that's the amenity, you know, but really what I want is. I want an emotional connection with the people who come here and I want them when they come here to feel like, well, we either go to a hotel when we go to Ojai or we could go to the Outpost.
Well, let's go to the Outpost 'cause we wanna see such and such, and we wanna hear that band and playing on their sound, on their audio system that we don't know, that we've never heard of, that we now love on and on. And so we just tried to, we tried to build that community, so we sort of said, well, what's the brain of the business? What does the brain look like? What does the brain think? Like how does it, how does it operate? And then, like I said, we also looked at that kind of hub and spoke right now you can, everybody can kind of hang out in the middle of the outpost in a central zone that we have as the hub. And then the spoke, you can actually go out to your, your caravan and you have a very private little zone that's like.
You know, a yoga, private zen zone, quiet level, you know, so you have either extreme privacy or a total group experience. And without going on too long, I'll just kind of throw out one other big idea that we, we work on, on everything we do. Sean and I both believe there's always a low, medium, and high execution of any concept.
And in general, we do everything we can to stay out of medium because medium is where things get bad. So the example is, if you want great food, either find a food truck as the low or go to the best restaurant in town as the high, but if you get trapped in do an olive garden in the medium, you're probably not having a good meal. And so that's what we tried to do at the outpost. There's a high exposure to people in the middle and an in incredibly low exposure to people on the perimeter. 
David Millili: So, talking about that, it's a great segue, I think. Do you have any stories about, uh, guests who've arrived at the property as strangers and then built friendships?
Bradley Steward: Oh, yeah. Couple of my favorite stories. We'll do movie nights every once in a while where we'll just show a movie kind of sometimes as background kind of sometimes as people watch it. And to us it's kind of a moving tableau some nights, but on one particular night and we try to curate it to the guests. You know, and so on one particular night we'd seen, well, there's quite a few kids here this weekend, and, and we really do market ourself as a family place. Our typical customer actually is a family from Southern California, Malibu area. We get a lot of families from Europe, Paris, and so on.
And so we thought, let's put on the movie Chicken Run. And so I was there that night and I was walking across kind of by the actual screen that we were showing the movie on. And one of our guests walks over to me and says, Hey man, I just really appreciate you guys playing this movie tonight. And I said, well, yeah, you know, no problem at all. You know? And he said, no, it just makes me feel, you know, kind of respected and kind of loved. I thought, huh, okay, great, great. You know, you're respected and left here. And he said, yeah, it was, it was probably. One of the most difficult movies I'd ever scored.
I said, wait, wait a minute, wait a minute. Are you telling me you scored Chicken Run? He said, yeah. Oh yeah, you, I thought I assumed you guys knew that and that you were playing it for me. I said, no, no, no. We're just playing it for the kids. He's like, oh, yeah, I'm a, you know, composer and I scored that movie.
So that was a great night. It was kind of funny one, and then two other favorite stories for sure. Josh Grove and was at the hotel one night. We had a fire pit going and we had a guitar there, and Josh was sitting down playing guitar and everything, and the guests around the fire pit y you know, and he was kinda like, Hey, do you guys mind if I play a little guitar?
And they're like, yeah, whatever. You know? He picks it up and he starts noodling around on it and people are like, Hey man, you're pretty good. You know? He's like, well, you mind if I mind if I mind if I sing a song? You know? Yeah, go ahead. He sings a song people at the fire pit were like, man. I think you could do something with this. I think you've got a career in this man. You're like, you're really, really good. And he was so funny. He is like, oh, you think so, that's great. You know? And so that was a funny one just to watch that that whole thing happen. And then the last one is we had a guest one time. They'd stayed over the weekend. They called us Sunday night after checking out and said, we wanna come next weekend. And we said, well, we're sold out. And you were just here this weekend. Are you, you know, working in town or hanging around or what are you doing? They said, no, no, no. We were at the fire pit. Last night with Bradley Cooper drinking bourbon until around 3:00 AM hanging out at your fire pit and chatting. I said, no, you weren't. I didn't see his name in the books anywhere. Maybe, maybe it was somebody who looked like Bradley Cooper very long story short, it was him and he had hung out with them until, until that time and he checked in under another name. And that was amazing. I mean, those guests still come and they still, you know, every time they show up they're like, okay, who are we gonna meet at the fire pit tonight? 
Steve Carran: Oh my goodness. 
Bradley Steward: So it keeps, it fun and interesting for sure. 
Steve Carran: That is awesome. That is awesome. So I was on your website and I saw a few things that describe caravan outpost, experiential travel, relaxing, rugged, luxury, and a place to gather. It seems like you've really developed almost a culture at Caravan Outpost and really have a truly unique story. What advice do you have to hoteliers that probably are more on the independent side, that are almost struggling to find what story to tell for their hotel? 
Bradley Steward: Yeah, it's interesting. One of the first kind of head scratching moments I had in hospitality is, we were meeting with some prominent execs from. One of the big three hotel chains, and they were talking to us about working with us and what we had done. And you know, we have a lot of visitors from large hotel groups who, who kind of sniff around the outpost frequently. And one of the, they kept talking about their brand, their brand, their brand.
And I said, you know, I just have to ask you what do you mean when you say the word brand? They said, well, it's the name, you know, that, that we use and the Marriott, whatever. And I said, you know, I've never actually thought of those. Products as brands, and I've never even heard the word soft brand at that time in my life. I've never even heard that. And they said, well, you're outta your mind. It's our brand. This is our brand name. And I said, well, what I'm more interested in is that emotional connection piece. Okay, so go back to that. And I said, you know. How do you articulate your brand? How do you talk to people with your brand about your brand?
And one of the key questions for me, with a brand that you have to answer, you know, to answer your question, one of the things you have to answer is, well, what exactly is it that we want people to do with our brand? Answering that is key to getting the emotional connection. Otherwise it's just design and artwork.
And the problem with that, I mean, that used to be a little bit unique. And now with AI, you could, you know, in 15 seconds you've got an image for, or your logo and everything else you need. And so to me, I think you have to start with not who are we? I never liked that question ever, it drives me crazy. I think you have to start with a few questions. Number one, what has to be true for this business and this brand to work? What's true? If I take Ojai, what has to be true is people truly have to come here and they truly have to feel they are part of something other than just a overnight stay. And then what do we want people to do with our brand? I think Patagonia is an excellent example where Patagonia says to you, where our brand. Here's what we want you to do with it. We want you to go out and advocate for these values.  
And in order to show you how to do that, we we're gonna run a bunch of ads talking about the environment and things we care about. And we want you to go do that. And what happens is you form a bond, you form a relationship with a consumer where, where they're part of what the brand does. Not people who buy the label. And that's what we try to do with the outposts. We want you to be part of what the company and what the outpost does, how it lives in the world, not just somebody who said, oh, there's the Marriott, or whatever brand.
I don't mean to pick on Marriott, but you know, there's whatever brand and let's go buy the predictability of that. You know, that that's just not our model. And there are times when even I, myself. You know, book a reservation for a hotel somewhere outside of our place where I do want some predictability.
But I think there are a lot of people who actually don't, don't necessarily want the predictability. Predictability is kind of table stakes. Everything has to be great. All cars work good today. All computers are fantastic. All everything works. The bad products went away a long time ago, and so you have to be convenient, good, fair price, so on and so on and so on. Now, how do you articulate really what the brand wants to speak to consumers. 
David Millili: So you've always been on the adventurous side, you've been an entrepreneur. So what advice would you give to maybe the younger generation or people who are looking to start really just any type of business, whether it be, you know, apparel, sports, or a retreat?
Bradley Steward: Well, I think the best way to learn is to do. I know that sounds a little bit trite, and borderline Yoda, uh, quote from Star Wars but I really think, you know, if I just kinda look at my trajectory and the people around us, we have some friends who, who became very successful that were literally kids with us, you know, the founders of Lululemon and vui and, you know, multi-billion dollar brands. And I think what all of us understood, even today when we see each other, and again, I'll just use a snowboard metaphor because it's handy dropping in is how you learn to ride and dropping in does doesn't mean you're gonna make every run. It doesn't mean you don't crash.
Doesn't mean you don't get hurt. But if you don't drop in you never touch the earth that you eventually want to live on, and you never get the run of your life. You know, I always tell my kids, and you know, people who who talk to me about this kind of topic a little bit. I always tell 'em, you gotta, you know, you gotta pin a couple of thoughts on your wall.
And one of those thoughts is, could I be one of the most interesting people I've ever met? Could I be that instead of looking around for interesting people, could I, could I be interesting and what would it take for me to do that? And then the second thing I always like to have, you know, kind of pinned a little bit is if you don't live your life, who will live it? Who will live that if you don't live the life you imagined, will somebody else live it? And it's like, with my kids, they always say to me, well, somebody will be that. Oh, okay. But that somebody can be you, you know? And it requires a leap of faith and like I said, you know, the snowboarding metaphor is a abound, you know, because a lot of times the best jumps in snowboarding, you can't see the landing. I don't really have a favorite place I've ever ridden in my life, but when I think about the best runs I've ever taken, it's in Alaska where literally the slopes are so steep.
When you start at the top of the run, you cannot see the middle section of the mountain. You can see the top and you can see the bottom, and you have to take that leap of faith to know there is a middle. I'm gonna roll over the edge. I don't know, I, you know, I spotted it from the helicopter, so I kind of have an idea of where it looks like, but you know, when you're going in 50 miles an hour in knee deep snow, you, you kind of lose your thoughts. And you know, you gotta have that faith to ride out right out the middle section. 
Steve Carran: That's great. That's good advice. Well, Brad. You have definitely been one of the most interesting people we've had on the podcast, so thank you for that. But we have been asking you questions this whole time.
So this is where we're gonna turn the tables and let you ask David and I a question. 
Bradley Steward: Alright, here we go. What I would like to know from you guys, you're experts. I'm out there operating in the real world and making mistakes, like crazy and cleaning 'em up behind me. My question is for you guys, what, what do you see in your guests that links all of these people who start extraordinary properties together. What are the traits that, you know, when you guys think about, we're gonna bring somebody on, we're gonna do something, what are the traits that you see in the people creating extraordinary lodging experiences?
Steve Carran: I'll take this one first. David, I think it is almost a sense of curiosity, everybody that we bring on, they're not like, oh, great, I'm doing well in my life. I'm happy here. They're always curious about what's next, and they don't stop at curiosity, they put the action behind it. Like a lot of people have great thoughts of what you could build. Like people have, I'm sure, have thought about caravan outpost ideas similar to you, but they've never executed it. So it's that curiosity and then having the gumption and for lack of a better term, the balls to start a company. Right? Like it's a very hard thing to do. So like having that go-getter attitude to go start that company after that idea and continue being curious once you start it. 
David Millili: Yeah. And I think what we've learned, it's kind of the same as curiosity, but it's really as we've met a lot of people, you can just see the open-mindedness and this idea that there's something outside of their hometown or their state or their country. And a lot of these people, you know, as you travel and as you learn that there is something, there's a different way of doing it or a different way of living. And you know, some people like the beach, some people like the snow, some people like the city.
So I think what we've found with a lot of the people that we've interviewed, people who've kind of moved around, traveled and seen different things, really kind of have. I think the best viewpoint on just hospitality as as a whole 'cause the one thing you always want to feel when you look at hospitality is comfortable. And some of the most difficult times for you is when you're traveling and you're not comfortable, you're not used to that place and the hospitality you're shown, I think, sticks with you and kind of can shape you to who you are. 
Bradley Steward: Yeah. 
Steve Carran: Well, Brad, this has been great. We've been asking you questions this whole time. Our producer, Jon, has been listening behind the scenes. We're gonna kick it over to him for one last question before we get you outta here. 
Bradley Steward: Okay. 
Jon Bumhoffer: So one thing you said at the very beginning really stuck with me, and that was part of the lightning round. Like one of the very first things you said, you love beautifully lit spaces, which is something that immediately when you said that just hit me. I was like, oh, I feel the same way. I'm curious how that informs how you design caravan outpost and then additionally, what is one or two spaces that you can immediately think of that were like. You walked in and you fell in love because of the way it was lit in the light in that space. 
Bradley Steward: Yeah. I'll start with your second question first. When I think of beautiful light, I think indoor, outdoor, and I actually, and I actually think a lot about color, temperature and sort of the shape of light, if you will. And, uh, and I'll quickly mention, the sun has come out in my backyard, so my light might not be that flattering, but when I think about those things. I think about a few things. I think about it's another totally different story, but I had to spend a month in Iceland one time and I think about the light there very early in the morning. And the shape and the tone, uh, of the light on what's called Lan Street, which is the main street in Vic. And I think about just the kind of eclectic and sort of this, what I would call sort of a poppy, but soft light, and I think of that street and that environment. Certainly I also locally here in LA I think of the Getty Museum and the spaces around the Getty. I prefer kind of reflected light, and I'm very kind of tuned into, you know, in Ojai, I always say to people, if America had Spain, it would be Ojai. I'm gonna go from here to picking oranges and cleaning my orange trees up this morning and then if I wanted to, I could drive down the road and have olive oil and wine, so and grab some avocados from my neighbor.
So I live in the Spain of America and so I always think of that warm kind of light that's come off of a rock or come off of the earth. And to me those are the best, those are the best colors of light. There is somebody that I follow her substack Rua. You guys might know who has lobby riot and, and lobby riot. Always just does amazing, amazing images of really beautiful light. Almost, almost anything that shows up in her blog or her Instagram feed for lobby riot, uh, to me is filled with, you know, beautiful, beautiful lighting examples. So those are the things that I kind of think about and I kind of tend to go to those outdoor, you know, those outdoor lit spaces for sure.
David Millili: Well, that does it for another episode of The Modern Hotelier, Brad. This is where you get to let people know how they can get in touch with you, how they can find out more about caravan outpost. So plug away. 
Bradley Steward: Yeah. I'm actually quite happy. Part of being a brand and having a connection to the people who you work with and who experience your place as being connected to them. Anybody can reach out to me at brad@caravanoutpostojai.com and that's my direct email and I'm always happy to converse with people, learn from people, talk to people, and share our experiences. And then on the web, caravanoutpostojai.com is our website. And all of the information about our places on there.
And we're very easily to reach through the company there. Big part of staying emotionally connected is we are actively engaged day to day and we believe that's actually a critical part of living the story you tell. So there and we're present. 
David Millili: Well, that does it for another episode of The Modern Hotelier, the most engaged podcast in hospitality. Whether you're watching or listening, we appreciate you and hope to be with you again soon. Thanks for joining us, Brad. 
Bradley Steward: Thank you