Ep 3.11 Transcript
Lisa: All right, all you marketing managers and brand managers and photographers and writers. Thank you so much for being here on the Outside by Design podcast. Today I am talking to Kylie Fly. Kylie is awesome. She is has so much energy and she's hilarious. She's also a triplet. And Kylie is also a tremendously humble human being. She's a really big name in photography and has worked with every Big Brand you can think of and then some and she's humble. She's quiet about it and she works so hard. She's got a tremendous work ethic. So I really enjoy talking to Kylie. She is a real master of her craft. And this I think is one of the meatiest episodes in terms of just advice for brands and how to work with photographers. Kylie's amazing. Check it out. Enjoy. Learn some stuff.
Lisa: Hey Kylie, thank you so much for being on our podcast today.
Kylie: Thank you, stoked to be here.
Lisa: Yeah, so the first question we always ask everybody is to describe where you are and what your setting looks like.
Kylie: Oh, wow. Well, I'm currently at my house. And it's just a little loft in a little shed sort of thing. I don't even know if it really counts as a house, but it's behind my landlord’s real house. So I'm like in a little yard surrounded by ants and bugs and gardens and it's really nice. But yeah, my desk just faces a wall. So it's not that interesting or inspiring. There's not even a... well there's a window behind me, but nothing glamorous just a nice little corner in my little house.
Lisa: In Idaho, right?
Kylie: Yep. I'm in Boise, Idaho.
Lisa: Wonderful. That's awesome. And so you are on the move all the time with your job taking photos all over the place. So what tell us where you got back from and where you're going next.
Kylie: Oh, well, I just got back from Wisconsin of all places. So it was like my first trip to the Midwest. I do a lot of trips with this one company where we camp for a week at a time and we do it kind of all throughout the US and so I've been to a lot of States through that. And then my next trip, I head out tomorrow to Alaska. So I'm pretty stoked for that one.
Lisa: Oh my gosh. What are you gonna do in Alaska?
Kylie: Oh this trip is probably going to be my favorite because it's like the a great way to end the summer going to Kenai fjords area. So it's like a sea kayaking type of trip. We're going to do some kayaking and some glacier stuff and hiking and hopefully see some orcas and critters, you know otters and other wildlife and I'm sure we'll see some lots of Grizzlies because you always do in Alaska. So yeah, I'm really excited about it and we'll be hanging out in a cabin and getting boats to a different island and things it's going to be pretty awesome.
Lisa: That sounds amazing. Are you going to be shooting that are you an ambassador or an athlete in that?
Kylie: Nope I'm shooting both photos and video for this and then I'm also writing a story about it. So I'm working with kind of like a... I guess like a media agency, tourism type piece with Travel Alaska and some other companies and I'm pretty sure it's... I know it's a girls trip. So it's like me and two or three other women, which is kind of fun. Didn't really know it turned out that way so it's kind of a fun little surprise. I just found out. Yeah, should be cool.
Lisa: Yeah, that sounds amazing. I've never seen an orca in the wild that sounds incredible.
Kylie: I know, they seem kind of terrifying but I think it's gonna be pretty sweet. I hope we see one.
Lisa: Well I hope you get like amazing footage of animals.
Kylie: Thank you.
Lisa: I'm wishing you all the animals.
Kylie: Thank you, sending me the animal vibes. I love it.
Lisa: So my next question for you is what are you wildly stoked on? And that might be it, anything else?
Kylie: Oh man, like in life in general? I'm actually pretty stoked for fall to come up because I'm going to have some time off. I'm kind of giving myself some time off because I wanted to start climbing again, more often. The summer kind of goes nuts for me. So I don't get a lot of me time and I don't get to go on a lot of trips for myself. So I need to get climbing again and looking forward to that and I'm taking my WFR which I'm stoked on and that'll be great. And. Just more mountaineering, more stuff. I need to you know, get more skilled at you know, crevasse rescue and different trainings I'm doing so, yeah, I'm kind of just looking forward to getting in the best shape I can for expeditions I want to do in the future and goals. I have things I dream about, might build out a van. I don't know. I'm just kind of all over the place right now.
Lisa: Oh man, that's... I could see you living the van life.
Kylie: Yeah, we talked about it one time. Yeah, I'm kind of like, that's something that's always on my mind. We'll see.
Lisa: We'll see, yeah that's exciting. So you know, we have met and spent some time together at Project 16x and you know, you come across as this really energetic, happy person that's adaptable and comfortable in basically any setting. Do you feel that way? Do you feel comfortable in any setting?
Kylie: Yeah, I really do. I feel like that's something I have developed over time. I mean, if you met me when I was... obviously we're all weird when we’re teenagers but when I was a teenager, I was so freaking shy. Like I couldn't look people in the eye unless you like spent a good amount of time around me and I could warm up. Like it took me a long time to kind of break out of my shell with people and I've always been an extroverted personality, but when I didn't have the confidence which is like the epitome of high school, it was really hard for that to be seen by others. And so I guess like with my travel and with my work and the type of stuff I do, especially living internationally and traveling a bunch I know for a fact that's the reason I am more comfortable in my own skin now because I've had to get in front of lots of people and like teach classes or like just different types of things I've done to kind of lead you to where I am that I think really helped me gain confidence I needed just to kind of be normal and be myself. Like the normal Kylie that people that know me. And so instead of acting all awkward and shy until people do get to know me.
So that's something I tribute to my work because I'm meeting new people every single day and I work with them for about 5 days and I might never see them again. So that's just kind of the turnover of my life. And I think that's why I feel really comfortable. I could be in any kind of situation and be fine, really, even if it's cold and miserable or an airport for 24 hours. Like I just was. Who knows? It's kind of nice.
Lisa: Yeah. So what what do you do? Are there any steps that you take to prepare for a shoot even though the setting and the people and everything is different. Is there anything you do every time?
Kylie: Yeah, for sure. I mean, I think like the main thing that I have dialed is packing. Like I just got home today from a shoot and I have two nights at home, but I'm already packed for my next one. So I think the number one thing I do is prepare ahead because I don't like to feel stressed. And when you go in a situation stress, especially when you're traveling back to back and your chutes are jammed so you literally just are never home, then if you have any kind of added stress or you don't sleep the night before you're flying or before you're traveling it really can screw up like your vibe. So I definitely make sure to stay on top of my packing game. I'm really good at it. I can go about a month and a half before I need to do laundry. So that's pretty nice.
And I think that's my main thing is once I'm organized and all my gear is organized, everything is charged and ready to go, then I can relax. And you know, get the sleep I need or go climbing or do something fun. Get out, get in a run or something active because if I don't stay active everyday then I kind of get sad to be honest. Like, I have to like be moving to keep my like energy moving and my mood up just because there's a lot of hustle and bustle in my life. And so I need certain things that are somewhat continuous or... I don't know if that's the right word, something more sustainable. And that’s lot to do with my activity and also with my relationships with people in my life, my personal life. I just got to make sure I kind of hit all those things and once my my little buckets are full then I can be my best photographer, be my best self when I show up at a job. I'm not like worked or something or drained. You know, I have to make sure I kind of take care of those things so I can yeah, I guess perform the best I can and be in the best possible mood because yeah. So much of what I do is working with a bunch of people I don't know and I'm just meeting. And when you pull out a camera a lot of people are generally uncomfortable. No one really likes to be like, “here I go, take all my photos” and stuff. And so it's good like to have the type of Personality that people can get comfortable really quick. That definitely helps a lot with my work.
Lisa: Yeah, I would say that that's a real asset of your personality is that you are pretty goofy and it lets people relax. But you also are, you know, quite professional and that comes across as well. So I think you do a good job, yeah, creating a good atmosphere for people.
Kylie: Well, thank you.
Lisa: Because I think too, you know, we as a creative agency work with a lot of photographers in-house or contract with photographers like yourself and I think a lot of people don't realize it's so much more than looking through a camera and taking shots. It's so much of a personality and creative direction and you know working with people's emotions. And what like, what's your take on that? What do you think?
Kylie: Oh, yeah. That is so legit. Like, I think to me it's extremely important. I always tell anybody in my life that something I really value is I value people and their emotions or their moods or their feelings. I definitely care about, like, where people are at mentally or physically. All those things super matter, especially when you're working the outdoor industry. If you're going to be on a mountain all day, you're like on a river all day or on an expedition for two weeks or months or you know, you're spending a lot of time with these people in small uncomfortable spaces. Sometimes stuck in a tent for days on end or whatever. So I think it's really important to make sure people are comfortable. And happy. And like, if people aren’t happy the photos aren't going to turn out so good and I think that's like really important because if someone's hungry and you're like we got to go, go, go and like you're getting all these shots. I mean, sometimes you gotta grind and I think people get that and that also makes a difference but you really got to kind of gauge people's energy. I think that's something I'm able to pick up on just through years of experience and also working with people either on certain types of trips where I know it's gonna be extremely high energy or something. That's very demanding.
But yeah, just kind of checking in on people making sure they're feeling good making sure they're fed. They're not starving or you know, I've had times where people. I've kind of had little breakdowns like someone's been kind of emotional because they just went through a breakup and I've pulled them aside and I've worked with them through that. Like it's not just like being a photographer. If you really want to get the most authentic natural candid imagery, which is totally what I do. That's why I... so like, if I want to capture that, people got to feel like safe, they’ve got to feel comfortable. They’ve got to be happy to be there and everything goes so much better when you can do that.
Lisa: Yeah, that's what you think is your vibe is the candid natural? That's what you go after huh?
Kylie: Yep. Yep. I always say like, my work I like it to be raw and authentic. And I kind of hate the word authentic because who frickin’ knows what that means. But like that's why I go for candid. I don't like that posey stuff. I don't like telling people like go over there and do this and that and the other. I mean, sometimes there are certain things where you might have to move something or position someone and obviously that's the nature of the work as a creative director, but… really, it's about like capturing people doing what they do in the most natural way possible. And if there's something that I saw that I missed, then those are the times I might interject and be like, hey, that was freaking awesome. Will you do that one more time for me? Then they'll be yeah, okay! So it's like sometimes that's the way it works, but, in general, yeah, I kind of like to be a shadow, a fly on the wall so to speak so I can capture people in their most natural element. Ideally.
Lisa: Absolutely. I think that that's amazing.
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Lisa: So you've worked with tons of brands across tons of industries and you know, most of our listeners are marketing managers or they work in editorial or they’re brand managers and work in the industry. So, you know, do you usually end up talking to CEOs or owners or marketing managers and how all those conversations different?
Kylie: Yeah. I definitely feel like a lot of times... it kind of goes all over. But in general it’s with the marketing people - like obviously like the marketing director, creative director, or someone like that is generally going to be like the one who is important, the one who is looking for this type of work. And so they'd be interested in = talking to someone like me. Occasionally I've run across like people that... maybe they're just over like social media and like that kind of happens, that's a different type of shoot usually but. I have talked to CEOs and owners of companies, generally like a CEO is in Communications if they're like a smaller brand and they're like kind of like a one-man show where they wear a lot of hats type of thing. But yeah, so it totally varies. But for the most part there's a marketing person and occasionally it'll be like a sales rep or someone random that like follows my work or kind of sees my stuff on social and they're kind of a fan of what I'm doing so they might pass me on to marketing. And that's kind of the way the conversation starts it totally depends. But yeah, that's what I would kind of generalize.
Lisa: So what what is your tip to a brand or a marketing manager on how how to work with photographers? Like what's your ideal dream client look like? Not so much the brand itself but like their behavior.
Kylie: Oh, man, I mean, I think it's really important for brands to respect the artist. I mean anyone in the industry will say that but like, it means so much to us. Like if you approach us with like, we love your work. You don't have to be like a person that's like stroking in the complementing non-stop. But like, if you just say like “hey, we've checked out your work. This is a product we saw that you did that really synced well with us.” I think that's cool because it shows that they actually paid attention to what you're putting out there. It's not just like, “you're a photographer? Cool. We need one. How about this?”
So it's like if they have specific things that they're looking for and they bring up specific things that they've seen in your work, they’re like “we love the way you do this that and the other, we love the way your photos speak this and say this” you know that type of thing. When they give me an idea of not only what they loved about what I've already pushed out and created but what they're looking for and how they tie together. Because that makes me feel like yeah, this really works and I understand the direction right off the bat. So that's always a great conversation opener.
Also, gotta love when they mention that they have a budget. Because nothing's more painful than getting an email that makes you feel good and at the end, “but we have no budget.” Because it's like cool man. I can't buy my meals with backpacks. So yeah, I think that's just a side note. But like, it definitely means a lot to like be super straight about what they're interested in, what their budgets might be, and what they love about your work and why they think that you guys work well together. That helps me at least.
Lisa: Yes, is there any... I mean, and this might be a hard question to answer because your career is always evolving and the different types of projects are always evolving and social media evolves. But is there anyone at this point in your career, like any type of client that you just can't take on any more or that you have to say that would be a bad fit?
Kylie: Yes, that's definitely happened to me. I mean, there's probably one or two I could think of sometimes but it depends on the relationship and how much it's worth to me. And what I get out of it. It's not, I obviously don't do what I do for the money. I do it because I love and I'm passionate about it. And I just I'm stoked that I can do it, just gonna keep riding that wave. So like, it's not about that. It's the type of thing where if I have to pull out of a relationship with a brand or a company that I've shot with it definitely has to do with how I'm treated or how... Yeah, I guess just the overall treatment. I've had to cut myself loose from a specific company that I work with that it really needed to happen like for my own good. It definitely had to happen and it was a hard conversation to have because it kind of felt like, it kind of feels like you're quitting and that's kind of a weird thing to navigate when you're a freelancer and you definitely are hustling all the time to just load up as much work as you possibly can. I think that's important though. I think it's important to know when to say no and when to step away from something if it's no longer serving you in the way that you need that helps you grow. So.
Lisa: Absolutely. I think it's so important to make sure that everybody is benefiting from partnerships or relationships or situations here you bring in a photographer. I think it's so important to value, make sure everyone is happy and getting what they need.
Kylie: Yeah for sure.
Lisa: On that note, so we work with tons of photographers and they all have different styles in the way that they interact with humans and the gear that they choose to use and you know, everyone has their own style. So I'm curious what's your process look like, like your creative process when you go into a shoot. Like, how do you thrive? What's your favorite kind of shoot?
Kylie: Oh, I'm definitely run and gun style. So I'm all about like running around outside all day with a backpack with all my crap it so I'm definitely used to packing around a lot of weight. If I'm going light with like one body and one or two lenses or something, that feels super amazing like a little butterfly. So it definitely is... I'm used to hauling a lot but I think it's important, you know, that you got to have all your gear. And also a lot of my shooting isn't just like stepping outside and shooting, like I have a lot of other gear because I'm doing some kind of recreation or you know, some kind of activity where I need equipment. And so I'm definitely doing a lot of that hauling stuff and very candid, on the fly, spontaneous.
I rarely ever have a shot list. I mean like, you have shots in your head that you want and depending on the project. Like if it's a film that's totally different but... like especially with narrative type stuff. But if you're doing candid lifestyle, or like branded work where it's like, this is the trip, just capture it. That's what I love about it is there's like a flow that you get into because you're just there and you're present and you're enjoying it and you're just kind of absorbing it and shooting it. So that always helps me to get in the mood.
I also, one thing I think is pretty important about what I do is I have a lot of shoots where I'm there for multiple days. So usually my shoots range between four to six days actually. And that's pretty long. I mean, I feel like I'm kind of gone like a week at a time if you count flying and your travel days. So a lot of times I will get to my location of where I'm shooting and if I can get away with it, due to like certain types of shots I need, I take the whole first day like not even touching my camera. I like to just be there and be present and connect to the environment and where I'm shooting. Check my location and the people I'm with if I'm with people and so. That really helps me to, not only myself get comfortable to adjust but also the people I'm working with to also kind of get in that zone. Because sometimes if we get off a plane and then we're unloading our gear and you're shooting right away, it's like no time to breathe and no time to like look around. And so that helps me to kind of stay inspired and look for the shots I want and almost like premeditate what I'm about to do.
Lisa: Oh, that's cool. That you look at that like a premeditation almost, that's amazing.
Lisa: That's cool. Do you find that when you work with athletes that it's pretty collaborative when you're shooting action sports, or do you kind of go into it like hey, here's the kind of shots we're looking for? Or how does it work for you when you work with athletes?
Kylie: For the most part, I would say athletes are there to like just get the shots you need and most of my experience they'll be like so what are you looking for? What do you want me to do? A lot of times they want to be told what to do, because they're not gonna be like, “so I was thinking I want this that and this.” Sometimes that’ll happen if someone’s super super stoked on certain imagery. But you kind of have to have an athlete that's like really into imagery or like media or they have to have some level of interest in like how the photos are going to turn out or the film is going to turn out to like really have a strong opinion, at least that's my experience. And so generally I’m the one that calls the shots and will give them like a really simple breakdown of here's what I'm thinking. Here's what I'd like to see. What are you comfortable doing? What would you like to do? Is there something you want to climb or ski or you know, whatever it is that we're doing. Like what's your level, where are you at? And what are you interested in?
I definitely want to know that because I'm not going to say like, hey, let's go climb this if someone's not comfortable doing it or if they're like, well, that's lame. I could do something more exciting or you know that type of thing. So I get their opinion and find out where they're at and then kind of give them a general overview of what I'm looking for. Like, there's this skier I was shooting with once were the first thing he was like, what do you want me to do today? And I was like, I think it'd be awesome to get a backflip. He's like sick. Let's go do it. So like, that's cool. Like if I have something very specific. Other times it might be like, let's just have some fun and see what happens and that's exciting.
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Lisa: And you're an athlete yourself, how do you think that that helps your photography?
Kylie: Yeah. I always tell people like, if there's something you want to shoot then you gotta do the thing that you want to shoot. And so it just makes sense for me to be as proficient as possible at the things I want to shoot. Like if I want to photograph mountaineering and climbing and people in bivvys and you know, all these different things that catch my eye and my interest, then I need to be able to keep up. I need to be able to participate and carry my own weight and also share my skills and talents with the crew so I'm an asset to the team. Like there's nothing worse than feeling like the slowest and the weakest and the most unknowledgeable person.
Like I've definitely had jobs specifically because I ski or because I climb or because I can keep up on a bike and I'm not good at any of those things. I mean, I'm a very mediocre athlete. Like I for sure don't hide I’m not like a shredder of any kind people might be like, whoa, that's so cool. I feel super normal. I work my hardest to be the best I can and there's so much I still have to learn, so much I need to get better and more proficient at and stronger at. So like my list of my skill level is pretty long and as far as what I want to improve on but I'm definitely always inspired and motivated because I'm surrounded by that. I'm embedded in that. But I put myself in that so I'm looking for that and that's why I spend my time pursuing those types of things because I want to be there and I want to shoot it and I want to be the person that can keep up so.
Lisa: You're the only other person I've met that puts rocks in their backpack for photography purposes.
Kylie: [laughs] We're so cool. “Oh, this rock’s gonna fit so nice in my bag.” That’s great.
Lisa: Ooh, that’s a really good rock. Yeah.
Kylie: That's awesome.
Lisa: Yeah, but I do think it's incredibly important to be strong and you know.... not only strong with your gear but physically strong and capable and I do my best.
Kylie: Yeah, it's awesome.
Lisa: Yeah, you try. It's because yeah, you like you said, you want to be an asset to the team in whatever capacity that is. Yeah, I don't know. Yeah, it's tough. It's exciting though.
Kylie: Yeah it is. And when you're on the mountains, you kind of have to have a lot of skills. Like it's not just like, I got to be good at my job with a camera creatively. I also got to be able to do it when I'm super uncomfortable, super tired, super hungry, when it really sucks, when the weather sucks or you know, there's all kinds of things that come into play. And it messes with your emotions too. It's not just like a physical thing or a mental thing, where you're thinking about creative stuff. Like you also have to be emotionally stable to handle situations when they get scarier, like if someone gets hurt or someone’s sick or if you're in a really remote area, there's all kinds of things. You're kind of balancing all the time. You have a job that you need to do. But you also need to take care of yourself in the people you're with so it's just a lot of, you know, skills that you gotta always be working on.
Lisa: Yeah, this this winter I'm having everybody at Wheelie take a Wilderness First Aid and a Avvy level one just because…
Lisa: I feel like our insurance company would be happy to know that since we go on a lot of strange situations.
Kylie: That's awesome. Yeah, that's awesome.
Lisa: Yeah, I think it'll be fun. I've never taken a Wilderness first aid or first responder. So I'm excited to learn some stuff.
Kylie: Cool. Yeah, that'll be great.
Lisa: Yeah, so. I guess the last question is what's your advice to... two pieces of advice. So your advice to people who want to get into the outdoor industry and aren't in there yet. And then what's your advice to brands when they are seeking a photographer?
Kylie: Yeah, I think the advice people wanted to get into the outdoor industry is kind of similar to what we've kind of already talked about, as far as if there's something that you want to be shooting then you should be doing it already. You can't expect to shoot climbing if you don't know how to jug a rope. Or you can't expect to shoot backcountry skiing if you don't have the Avalanche education or backcountry experience, you know, you have to be able to have those basic things in place before you can even consider injecting yourself that environment as a professional. So I think that has a role.
And then really it's about... and when you do that, when you're like meshed in that environment, like you're hustling and doing your fun outdoorsy things, then it definitely helps put you in that direction as far as brands or companies or sponsorships. Like you never know what your foot in the door is going to look like, could be someone you've been skiing with for three years. It could be like some random person that you meet on a trail. You just don't know, it could just be like a backpack that you've been wearing for five years and someone's like dang you really like that. What brand is at? Oh you should work with them. Like you just don't know, and so I think you just kind of have to be working all the time and like sharpening your craft and shooting all the time and networking and making friends with people and talking to people. And really it's about building authentic relationships with other people because cold calls, cold emails slinging business cards, you know that can help in some ways. You know, that's something as important, but like it's not everything. So I think that kind of helps get people started.
Lisa: Yeah, and then what's your advice to a brand when they when they, I guess beyond photographers, like if they want to work with somebody creative. What's your advice to a brand?
Kylie: If brands want to work with someone creative, what is my advice? I would say... At least, it really helps when a brand knows what their vision is, like what they're looking for. And I assume any time a brand reaches out to me that they're familiar with my work, that they've seen what I've created and they see what I make and they liked it. So they wouldn't be reaching out to me if they'd never seen my portfolio. And if they hadn't I'd be a little bit like, really? Well that's different. So I think it means a lot to have brands doing the backend work at least becoming familiar with you as a photographer. I don't know what their job looks like, but that always makes a difference just knowing that they're paying attention to what you're creating and they've figured out why they like your work. And then why you can work well together so that always helps when a brand approaches me. And then just being clear on your direction, clear on what you want, clear on what your budget is and what your vision is and how you think you can make stuff happen together. I think that's kind of it's pretty simple but. That's generally what I'm looking for.
Lisa: So awesome. Well gosh Kylie. Thanks so much for being here today.
Kylie: Yeah, thank you.
Lisa: And people can follow you on Instagram. It's @Kylie.Fly. Any website you want to share?
Kylie: Well my website is kyliefly.com if they ever care to look at it.
Lisa: I really love your Instagram stories. They're like, they're like my favorite.
Kylie: Oh, thank you.
Lisa: Yeah, you guys should follow Kylie because she's really funny on those Instagram stories.
Kylie: Thanks. That's fun.
Lisa: Thank you so much for listening. You can follow Kylie on Instagram. It's @kylie.fly and you definitely should, like I said her stories are hilarious. It's my favorite when she and her sisters, because they're triplets, get together and they are hysterical together. I really enjoy that, it’s like my favorite story of all time, and you know, check her out. Her work’s amazing. So do that. Do it right now.
Next week tune in as I speak to Katie Lozancich who is a digital content contributor at Teton Gravity Research. She and I talked about what's really going on in mountain towns and everything that TGR is doing to try to tell stories about what's really going on in mountain towns. So tune in next week.
Katie: What's been really exciting to be on the TGR staff is to see our company really pursuing these heavier topics within the action sports community. We recently came out with this movie called Andy Irons Kissed by God, which follows the life of Andy Irons, three-time world champion surfer. And you know, through his life and story we bring up the discussion surrounding mental illness. Andy Irons struggled with bipolar disorder his whole life and also, you know, his longtime struggle with drugs and addiction. And so as someone who is newer to the staff it's really cool to see our company transitioning into these tougher topics. And I think that's a trend the action sports community really needs and also I can see it with other production companies really needs to shift towards. Because I think for so long we have only been kind of talking about the stoke and what's rad but in reality, there's like a lot of pain and there's a lot of struggle. And it's been really exciting to be part of a company that values that discussion and recognizes that, you know, through these stories we can connect with people who may not even be surfers, right, or may not even be professional athletes and they can find solace and Comfort through someone else's story. And I think that's that's the most impactful and powerful thing that stories can do.
Outside By Design
A business podcast for people who love the outdoor industry.