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Episode 139: Creative Director Jason Tisser on Listening & Learning

"Really great ideas come from anywhere."

This week we're joined by Jason Tisser, freelance creative director (formerly at Sun Bum). Jason talks about transitioning from the agency side to the brand side, why listening is so important, how he frames his creative process, and more. This one is full of gems!

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Episode Transcript

Jason: That was the thing about Sun Bum that I loved was the smell of the product, right? I experienced it before I worked there on a vacation in Hawaii. So when I have the smell, it reminds me of vacation in Hawaii. Right? When you sell things that remind people of what they love to do, or like experiences that bring them personal joy outside of like the calamity of life, that's, that's already a layup. Right? It's getting it, getting it right. What you want to say, but you already have a leg up because people are already passionate about it to begin with.

[intro music]

Iris: Hello and welcome to another episode of Outside By Design! My name is Iris Matulevich, I host the podcast alongside Lisa Slagle, and as always, the show is brought to you by WHEELIE, a modern creative agency and production company for the outdoor industry.

This week Lisa interviewed Creative Director Jason Tisser. Jason has had a long career in creative direction, from agency life to working internally at brands like Sun Bum, and now he’s gone freelance. Jason spoke with Lisa about his creative process, why listening is so important as a creative director, managing creative disappointment, and more. If you do anything creative in any capacity, you’ll learn something from this episode. Let’s dive right in.


Lisa: Jason. Thank you so much for being on the podcast today. I'm excited to talk to you.

Jason: Thank you very much for having me.

Lisa: The first question we ask every single person is to describe where they are in the world and what they're looking at.

Jason: I am currently sitting in my three-year-old’s bedroom, in Redondo Beach, California, staring at a bunch of stuff I probably have to clean up later.

Lisa: That's cool. Iris found you and booked you - Iris works at WHEELIE - and I'm not sure how she found you, but I'm really curious to know - because this podcast is so heavily influenced by the outdoor industry - what's your background and how did you get to where you are today? What's your story?

Jason: Well, I guess I've been working in creative advertising for a pretty long time, since like 2003. I'm originally from Texas, went to the University of Texas at Austin, a fantastic town for the outdoors and did the advertising program there. And then just kind of made my way working at lots of different advertising agencies around the country in Dallas and Las Vegas of all places, Chicago, and then out here in Los Angeles. I was mainly in the advertising agency world for a long time, just making all sorts of creative.

And the pandemic hit. I have two young children, so juggling life with my two little kids while working kind of advertising agency hours was a bit gnarly and I started thinking… maybe brand side might be a better place to be. Just ‘cause… a lot of times I would be presenting ideas to clients and sometimes the nature of the relationship between agency and client moves really fast. You don't have the time to sort of develop the relationship and understand their business the way you need to. So a lot of times I felt like I was presenting ideas that were ideas, but also business solutions. But if you're not inside, you don't really fully understand. So they'd be like, “that's a really interesting idea, but that would take us like four years and cost way too much money to do. So I don't know if you guys fully understand what we have going on here.” So I figured maybe I could see what's out there and go the other side of the coin and kind of really learn what it's like to be inside a company and see it from all the different angles and fully understand more than just sort of the marketing piece of it to sort of be like, how can we propel this forward and just be better at what I do. And that's kinda how I ended up at Sun Bum. That's like, that's probably how you guys found me.

Lisa: Yeah. Because you were the creative director of Sun Bum.

Jason: Yeah. Yeah. I worked there for about a year plus. Yeah.

Lisa: Cool. Okay, I'm fascinated by this because, you know, I own an agency, and so I've never had the opportunity to work in-house as a creative director. And I always love talking to people who have experienced both. So like, what did you personally learn?

Jason: I mean, a lot. I like to approach things as, you know, I… I like to tell everyone that I, I very much don't have all the answers. And I want to go into a room with people I feel are much smarter than me, and then just absorb from them.

I think what was kind of really interesting was beyond the marketing and advertising things that I generally kind of understand, I think what was cool about being inside a company was, you know, you're not only looking at… agency world, you're kind of like, okay, what's the next week? What's the next month? Like we're planning out for the year, but things happen really fast. So you tend to have a shorter view cause you have to kind of get each project done. But being inside client, it was more of like, okay, so, you know, what's 2024, what's 2025… what's going out, what's the longer view of things? And then what are the bigger strategic goals and then how do you get there? And then how do you start talking about your marketing players for the next year? And then that's across so many different touch points, right? Not just like a project or a brand campaign you might do with a client. This is more of like, let's look across the whole spectrum of, you know, ambassadors, events, product launches, different things change things up. Right? Well, maybe we can't get this componentry here. Or, this ingredient might be not necessarily there and obviously supply chain disruptions with kind of where we are today affect a lot of different things.

So it was kind of being in some meetings where it's like, “do y'all really want me in here? Like, do I have anything to say here?” But they're like, no, it's more for you to understand kind of like what's going and how that could affect certain things. And then think about the bigger strategic picture of like, okay, if we have to pivot and go in this direction, what does that look like? Or should we sort of stay down this path? And it's kinda a bigger picture thinking, which I enjoyed. At the same time, you're pretty deep in the day-to-day of like the little things that you’ve got to get done. So it's kind of managing the two. So that's kinda what I saw was more the, the, the business side of things where I was like, “oh, that's why that it's like this”, or, “okay, I understand this,” or, “I should probably ask a few more questions here, cause I don't know what we're talking about.”

Lisa: And so now you're freelancing, you're a freelance creative director.

Jason: Yep.

Lisa: And why did you make that life choice? What is your… what’s driving you there?

Jason: Basically just trying to figure out the best flexibility between work-life balance. I mean, kind of like, I feel like it's… everyone's kind of facing the same thing. I think like… the world kind of turned itself on its head a little bit the past couple of years, I think what's really interesting was… so I've been managing creative teams for a couple of years. And what I've seen is a lot of people want sort of different flexibility and it depends on where you are in the spectrum. Right? And you have to respect where people are. Like, if you're young and you're working… you're working from home and then you kind of want to be forced back into an office and that might not work for you, but you have your own concerns, as, like, living by yourself and feeling kind of isolated or parents with young children are kind of at different wells.

So everyone's trying to figure out like what's the right balance between like, I want to work really hard and get stuff done, but I also like autonomy too. So I'd done freelance before in the past. And look, Sun Bum’s an awesome company and the future is very bright and there's really smart people there doing some really awesome things. And I mean, the brand is… what attracted me to it was, it is so… like there's a lot of deep meaning that people from the outside probably don't see of like the design, the topography, the influences of what make it what it is. And it's treated with really, really high bar respect and understanding of like, this is what kind of the secret sauce to make it special. And it was really cool. And I learned a lot. I just was commuting from Los Angeles down to Encinitas, which is beautiful, but 95 miles south of where I live. So I had to kind of figure out what's the best, like work-life balance for myself and my little guys. So that's all.

Lisa: That's cool. What… now that you're freelancing, what would be your dream project?

Jason: Oh, that's a good question.

Lisa: Yeah.

Jason: You know, what's funny is I've worked on a lot of different stuff and, you know, it's probably… what you actually sell, sometimes - obviously, unless it's like something terrible, harmful or evil - but it's more of like, who are you working with? Are we trying to do something good? And is it interesting?

Like, I tell people, you know, I've done lots of different stuff, but some of the things I found kind of interesting was, you know, foil and trash bags. It may not be that exciting to some people, but there's, there's, you know, I've done complicated things like insurance, where… it's not super complicated, but like you're selling people air and you know, you're trying for people to wrap their heads around certain things, why they have it (besides being mandated by the government that you need auto insurance), but it's more of like, you know, what a trash bag is, you know, what a piece of foil is. And so it's like, how do you do things that's kind of more interesting like, you know, you put food in it and cook it. Like, how do you grab attention?

And I like CPG. I like things that people can tangibly hold. ‘Cause it's, it's, it's a bit easier to be like, okay, on face value, you kind of get what this is. But how we tell a more interesting story or how we engage people in a different way? Cause they're kind of used to seeing the same things. I don't know. Does that make sense?

Lisa: Yeah.

Jason: Sometimes I ramble. That's part of, kind of how my brain works.

Lisa: I think a lot of good things can be found in rambles, so I’m there for it. Yeah. So I'm curious, what's your experience being a freelance creative director where you don't have the same team around you constantly? Are you integrating with other teams? Are you like putting together a ragtag team for the project? Like what, what you got going on?

Jason: It all… it all depends. Right? Sometimes it's… you kinda, you jump back into it where it's like, you kind of have a collective of people that you worked with before in the past that you reach out to, if they're still doing freelance. And sometimes you work with people you know, and that could be, “Hey, I need you to sit down and hammer this out and come with ideas and kind of do what you're used to doing.” Or, “I've got these two teams, here's a project, it's kind of halfway there,” but like work with them and help coach them to be like, “okay, like, what you guys have here is some really cool executional ideas, but like, are we answering the strategy on the brief? And then what are we trying to accomplish and answer? Like, are we, are we really answering this? Are we just trying to do something kind of cool that we think would get some attention?” So some of it is that, some of it is, “Hey, I need help kind of setting this up and helping to organize people.” It's kinda pretty varied, which I think is, is, is exciting.

Because what I've noticed is, you know, I'm sure owning an agency for a long time, you've kind of seen everything change quite a bit. Right? You could have people go off tomorrow and be like, “Hey, we had this crazy idea that we launched online and now it's taking off. And how do we like do stuff with it?” Or here's this brand that's been doing things forever with a more structured agency retainer, but like, we really need some different brains to kind of like take on this one project.

So I think everything has just… it's changed so differently. It just depends on kind of who you know, and who you can get in to talk to and be like, “okay, this is interesting. How can we take this and do it?” Or, you know, I like freelance. I've done it before, but then again, you know, I like full-time too. There's… like I said before, there's something about getting in somewhere… and it takes a while, right? It takes a while to sit and fully understand a brand, its voice, the objectives, like, strategically, what are we trying to do here? You know, does this make sense? You know, what are the healthy collisions of like, “Hey, I know you guys say we're going to do this, but like I was thinking about it, but like, it kind of makes more sense here.”vRight? And are we open to having that conversation about, does this make sense? And how can we position it a little differently? So I don't know, again, I think I'm rambling, but that's how my brain goes.

Lisa: I love that answer. I think that there's an ease to your creative process, is my guess. Like, yeah, what's your creative process typically like? You seem pretty laid back and thoughtful.

Jason: You know, it's, it's funny. It's… I think it's changed a bit. And I wonder if - I was going to ask you this question too. I wonder… what I've noticed is the creative process for me has gotten a little harder to focus as like, you know, you kind of manage teams and move faster and fly from meeting to meeting. ‘Cause you don't get the same amount of time you used to have to really sit and chew on something. Or a lot of times you chew on something... I mean, earlier in my career, you know, you stay up super late. You work really hard. You figure it out. You go round after round. I always kind of felt that was good, but then again, 20% of the time - actually more, probably like 80% of the time - you're kind of going back to the first couple initial thoughts you had. They just weren't there. So for me, it's more like, take something in, think about it, kind of jot a bunch of notes down, and just talk to a lot of other people. Like, my big thing is really great ideas come from anywhere. So I want to sit with people that have different perspectives, have different thoughts. And then… ‘cause a lot of times, we live in a society now where, God, there's so much stuff and there's so many audiences and they're very fragmented and there's an authenticity that people want to hear that's very particular to them.

And, you know, when I walked into Sun Bum and there were certain things, like I don't surf. I can get on a skateboard and probably fall off of it. My six year old son is a much better skateboarder than I am, but what I was able to do is kind of go into the world and bring my perspective to it and sit and be like, okay, like tell me, like, I, I know, you know, so-and-so, you're a big skateboarder. Like, what's important to you here? What makes sense to you? And then get their POV and they'd be like, that's really cool. And I had this thought, that's kind of a more general idea of how can we take that and make that message more relevant to you and the people we're trying to talk to. So for me, it's just talking to many people, bringing my POV to the table, but also really taking in everyone else's thoughts. And trying to construct, because what I love about creativity is it's not math. There is no one right answer. Right? There's… there's no way… there's a gut feeling. Right? Where you’re like, you look at a bunch of work and you're like, “okay, this is it.” And I've sat with teams before where I'm like, “guys, I like this. I don't get this at all.” And I've had teams like, “no, this is it.” And you're like, “all right. You know what? I don't have all the answers. I'm not right. If everyone feels really strongly about this and we think this is the most interesting thing, let's go with that.” And we'll kind of see how it goes and if it's successful, that's awesome. And we'll learn from it. And if it fails miserably, that's okay too, because we'll learn from that as well.

Lisa: Mm. Yeah, I think all those perspectives are critical. You know, just bringing in a lot of lived experiences as well as, you know, challenging assumptions.

Jason: Well that's - yeah, that's kind of like, how do you, you know, you just move really fast and you aren't able to kind of have those thoughtful conversations.

And I think a lot of times you're racing towards a goal of like, okay, we need to get this done. And sometimes it's like, what is this? And then you have to, you have to balance it out. Right? Someone always told me, like, ‘good is the enemy of great.’ And I find that's true, yes and no. Like, yeah, you want the most amazing thing always, but you have to balance out like, okay, what is going to solve this problem and make sense here? And where is my time best divided to really tackle a problem that I think is interesting. And to me, that’s…

I love creativity when it's unexpected. You know, I love seeing that, like, funny little line on a package. I love seeing a little thing that someone did somewhere small. I mean, this was a couple of years ago, but I, it was such a small thing… Wieden+Kennedy, the advertising agency in Portland had KFC for a long time - I feel like I'm explaining things that people already know, but anyway, they had the digital account for Kentucky Fried Chicken and they did this little thing where they changed… they changed the Twitter profile of Kentucky Fried Chicken to follow the Spice Girls and 11 guys named Herb. So the secret recipe of 11 herbs and spices, and someone just figured that out and tweeted it back to them. And then they made a big deal of it and created this oil painting of the guy, like on the back of Colonel Sanders on a segway. I think. I could be getting some of this wrong, but like it's such a weird, simple thing that knowing kind of what their audience online is, would eat this stuff up. Again, I'm not in the inside. I don't know. But from the outside perspective I saw it, it just like, it filled me with such a joy and inspired me to like, I want to do stuff like this. ‘Cause I know these little things can make people super happy and that's kind of sometimes what I, you know, what makes me really enjoy doing what I do is like, I'm sure you see some, something, something sometimes where you're like, oh, I get what they're doing here. Oh, that's so great. I love this message. Oh, I wish I would have done it. Oh, and that fuels you to do more. That's kind of the way I look at certain, certain things.

Lisa: I love that. So the thing I've been fascinated with lately and how I've seen a lot of our clients change is like, humanity has been rocked over the last few years, and everyone is like scattering and responding to change in really different ways.

And I'm fascinated by where people are sourcing stability. And they're sourcing it from - like, as an employer I can tell you a lot of places people source stability - but also like they're sourcing it from brands and products and experiences and ways that they didn't. Like your bicycle can be your only constant. Or like, you put on the same bibs when you're like going to go on a road ride or something, you know, like products are becoming a source of stability.

Jason: I think so. I think probably because… I mean, and you tell me, I'm curious, like, at least in my mind, when all of a sudden it felt like you couldn't get anything. And then when you realized what you have is your favorites you kinda go to it. And I didn't necessarily have the benefit of like a lot of people I know, like discovered certain things or like when they had that crunch time of like, you're locked down, you can't do anything, maybe you were able to pick up a hobby used to love, or you're like, you know what? I used to run all the time. I'm going to go do that again. Like, I have the benefit of time. I had two young kids, so it was more of like, just my days were so packed. I was like, what can I do? But I do, I do have my bike. And I was like, you know what? I don't live far from the water. And I was able to carve out some time where I could just ride my bike up and down the ocean. And like, I don't know if I felt the stability in the Trek bike I had of the brand itself, but you turn back and you're like, oh yeah, I have this thing. This is so awesome. This is… like, carving out that small time for you can like refresh your brain.

And I think, I don't know. I, I find... I mean, I tend to be a creature of habit so certain routine things I do I find stability. I can tell you, this is a weird thing. I don't know if you - and I don't know if I'm answering your question here, but like I found at the height when we were locked down, And like, you know, you're just kinda like you're stressed out. What brought me calm was when I'd work out, I'd watch like YouTube concerts, like live concerts of like bands that used to love in high school. So I'm like working out, watching like Rage Against The Machine and Green Day. And I don't know why, but I found this zen of like, okay, one day we'll go back to outdoor, giant concerts. And I feel like that's kind of what is giving me calm. ‘Cause that's what I want. I don't know.

Lisa: Are you an extrovert or an introvert, do you think?

Jason: Mmm… probably… I’d say extrovert. I can kind of roll in anywhere and talk to anyone. I think maybe lately a little more introverted because, you know, we've been a bit more locked down and a tremendous amount of my conversations tend to be with a six and three year old. So, you know, it's a more focused conversation on different things, but, yeah, more extroverted, like I roll into a room and like to meet people and talk to them and kind of find out like what they have going on and what can I learn from them and who they are, stuff like that.

Lisa: Yeah. I think general curiosity toward humans is kind of the big pillar of great creative direction.

Jason: Yeah. You have to be, you have to look at something and be like, “okay, what is this?” And this is like, as you know, you find yourself in different zones in your life, right? I'm clearly in the Parent Of Young Children zone. So I can speak to that really well. But what I, what I love about this job in working with different people all over sort of the spectrum is, you know, I might not know everything about this young TikTok influencer and what they're doing, but like someone can tell me what's going on and I can look at it for a little bit and be like, oh, this is a thing, I see what's happening. This is cool. You know, have you thought about doing this with this and does this make sense with them? Is this relevant to their brand, but this is kind of cool. And I see how this could be for this.

Like, at Sun Bum people kind of got tired of me saying this, but my big thing was connect the dots. Like… there, there was a lot of work, great work across like a spectrum of like events and ambassadors and brand campaigns and product launches. And I was looking at it from a bigger perspective of like, okay, there's one voice. So how do you take what you're doing with this ambassador, leverage it in potentially this experiential moment, and then spit that back online to maybe make this part of a product launch if they like it and they use it. So it feels authentic to the audience. So how do you tell sort of like bigger stories with the assets you have by keeping it a bit tighter in like the way you bring it out into the world.

Lisa: Okay, let's talk about that. ‘Cause I noticed in your pre-survey questionnaire, you mentioned fragmented audiences. And I think you're kind of speaking to that, I think, but I can't tell.

Jason: Well, I say fragmented audience - and I don't want to sound like I'm like an old man telling people to get off my lawn. I think it more of like, you know, everyone has the people they follow and they have what they're into. And if you're, you know, a K-pop fan, or you love running, or you're a biking enthusiast, or you want a mountain climb, you could go so deep into that community that you can get personalized information from 15 different brands and 15 different influencers. And just go down that rabbi hole.

And so it's kind of like, like specifically from a Sun Bum perspective, you know, there's a surf and skate DNA to the brand, but as you expand and go out, there's so many audiences that love the outdoors that are exposed to the sun, that you can go a lot wider. Right? But you have this one POV and you want to make sure that you stay honest to the brand voice, but you want to speak to different people because you know, a surfer and a rock climber are very different, but similar people, right? So you want to make sure that like you have something that's general, but is specific enough for both of them to like, kind of wrap their heads around. And that's kind of what I was saying with connect the dots. ‘Cause if you have this snowboarder and surfer and you know, you want to put something out that's like kind of a cool message, but that could apply to someone that goes and hikes in the desert. Because they're still exposed to the dangers of the same thing. It's like, how do you just package it up in a, in a way that like, even though they may be getting tailored messaging to them from different places, it kind of is enough for people to be like, oh, okay, cool. I get it.

Lisa: Mhmm. And like how they use the product in its quote unquote natural habitat.

Jason: Right. And is it like, is this something that you would do too, right? ‘Cause part of it was like, well, let's grab some of our ambassadors and be like, “okay, tell me how you use it. Like, what's cool about it? What's not cool about it? If you had to improve it, what would it be?” I mean, your focus group is there. So as opposed to going out into the world, like people that really use it, you're like, what's realistic, what's not? Because what I don't want to do is tell you something. ‘Cause I mean, how many messages do people get a day where you're like, oh, sure, whatever. Or at least from a branding/marketer side, you can see stuff you're like, oh man, they're really reaching there. They're just trying to create something because they think it's right. And we'll see how that lands. But.

Lisa: Yeah.

Jason: The goal is always to try and, you know, get close to the mark as possible for enough people to be like, “oh yeah, cool. Okay. I get that.”

Lisa: So if somebody handed you a product and they were like, we're going to do a product launch, launch it however you want, how would you start that? It sounds like you do quite a bit of research.

Jason: Yeah. I think… which is like creativity… don't you love when people are like, “Hey, you're creative, go be creative”. Like you should- we don't want you to have any boundaries. Like, just go do stuff. And you're like, “ah, okay, no,” like as creatives, like you need, you need some parameters, right? Like, you need like at least a playing field. Because when you see it, you can be like, oh okay. This is what you want to do, but have you thought about presenting it like this? Or have you thought about, you know, you're speaking to these people, but as you go deeper into like what strategically you're saying your goal is, your audience is really this.

So for me, from a more traditional sort of advertising agency approach, like the strategists are people that I just like love to pick brains, you know, your, your people that do the research, I'm kind of like a bring me the data, not all the data, because I can't go through all of it, but like, you know, do your strategery brain genius and let's sit and let's talk about it. Because my favorite thing is like, I love sitting down with very smart strategists and I have been very fortunate in my career to work with a couple of really, really smart people where they just kind of present things to you.

And they sometimes are deferential to the creative, right? They're like, well, there's this, but like, you know, you're the creative person, so blah, blah, blah. And you're like, “Well, wait a minute, hold on. What you wrote there? That's it. That's the idea. Like, you're talking about, here's an audience, here's what you think some messaging might be relevant, but the sentence you said two paragraphs ago, when you're just saying wild things, like, that is potentially a campaign direction.”

So a lot of that is just being able to put the lens of like how you want- how you think, like creative could be potentially refined. And then how is that going to be relevant to the audience? So a lot of times I feel like people are like, you go off and figure it out. But sometimes it's, it's there right in front of you when people just present you with like, “Hey, we have this, we talked about this. We talked to these people, this person in a focus group was like, ‘oh man, it's kind of like sucks when this happens.’” And you're like, oh shit, that person, what they said right there. That's probably better than me sitting and trying to write for two hours. Let's take that sentence and expand it. What would that look like?

So sometimes it's kind of that. It's like, I like getting the information and having at least like peers who we're trying to talk to, this is our goal. Go for it. Because you know, when I've also had briefs where like, who's your audience? Like, “uh, women!” Like, “Okay, like age range, interests, things they wanted to do?” Like, “women.” You're like, “huh. Okay.” ‘Cause if it's made for everybody, you're just going to be like, oh, okay. Fine.

Lisa: Right. It makes sense why I'm listening is one of your main pillars of your values, and it's also on your website that you like listening.

Jason: Oh yeah. I also tend to sometimes ramble and talk too much. So I'm working on that, to listen and be more quiet. But I, again, like, I really believe… and I try to… like I've, I've worked, been fortunate enough to work for really smart, awesome people in my career. And I just try to learn like, from them. ‘Cause like when you start off, like, I don't know, how do you manage people? How does, how does that work? Like, I don't know how to do that, you know? And as you, you know, go up the ladder and work with more folks, a lot of it is like, you know, you have to really sit. And, and I had a boss that told me managing people is managing personalities, and I was like, okay. And then over time we were like, oh, oh shit, they’re right. Get to know your people, understand what they're into, what their goals are, what they're good at, and just listen. because again, my thing is like, I don't have all the answers. Like it really is a team effort and you want to be like, okay, I have my perspective on it. And what I think is right. And I think you have to be very open to be like, okay, this is where I start. Know that where you start sometimes can be pretty close, but sometimes it's very different. So you have to have that flexibility and like kind of check the ego.

‘Cause… It's, you know, again, there's no like hundred percent right answer. There are times - I'm sure you've seen it - where someone brings you something. You're like, [snaps] that's it. Just go do that. I love it. I get it. Bring me more of it. You know, or there's times where you're like, okay, we are on something. I don't know what it is. And everyone's looking to me to solve it right now. And I can tell you right now if I did that, it probably won't be where it should be. But let's explore a couple of different ways. I think it should be like this, but why don't you bring it back to me and let's talk about it. Because I don't want to jump in with my perspective, because… you know, obviously there's times when you have to, but it's like, okay, I want to push it a little further and see where it ends up because I'm hoping it gets to a certain place. And if not, I'll jump in and mess with it a whole lot. But like, you seem very passionate about it. So I would give you this direction and then bring it back to me. And I find that, you know, if you lean in with your people and listen to them and don't try and say, “no, this is the way it's going to be.” You'll come back to a better place. And you just have to be, you have to be flexible. You have to be. Or else who wants to work for that type of person?

Lisa: Yeah. How do you navigate what I called the very client-driven project, where you have an idea and then it ends up getting tweaked and tweaked. And then… I call it very client driven creative. Like, how do you navigate that?

Jason: That's a good question. You know, you try and do the best you can with what you have. And I don't think you can be too hard on people. ‘Cause I think ultimately, if people are passionate, they want to do the best job they can. And don't get me wrong. There are times where you've had very hard conversations with certain clients and been like, “Okay. This is why you hired us. This is what we think. Ultimately, it's your brand. Your dollars. Your choice. We highly recommend this, but if we're going to go this route, we'll do it the best way we can.” And you kind of have to teach that over time where, I mean, it used to be, it used to be… earlier in my career, if you ended up with like two things in your book for a year that you're super proud of, that's a killer awesome year. But that was like when it took a lot more time to do certain things, I think now is just, what's your ratio, right? Like, I also tell people, um, you know, let's be honest, a lot of stuff, you work on, a good portion of it isn't going to be that great. But some of it is, so my perspective is - I mean whatever, I'll just kind of, I'll be honest. Like, I kind of tell people that I work with them… like, look, we're all going to have to eat some shit. That's how this works. You know, my goal is to make sure that we balance out how much shit we eat with how much stuff that we absolutely love and we're super stoked about. And the goal is like, to balance the two.

So like, there's ultimately going to be disappointments, but understand that in this game and in this industry, there are so many at bats that you're not going to bat a thousand, you know. And it's hard because, you know, I guess, I guess you have perspective if you've done it for a while, you're a little bit of a realist of like, you ultimately always want to do the best job possible, but sometimes things end out the way they are. And if everyone is kind of happy, then you're fine. It may not be the most beautiful thing you've ended up with, or, you know, if you're really younger and you're really passionate about it, it'll stick with you and be frustrated. But it's one of those things where it's like, “look, I feel you, I understand you're upset. You're totally entitled to your feelings, be upset about it, but the way you're going to persevere and move on here is you just move on to the next thing and take the learnings from where that was. And then maybe we can end up somewhere better some other place.” You know, and, and the way this kind of business works a little bit, if you kind of get stuck in a place where you're kind of frustrated and it's kind of a bummer, you, you may find yourself, you want to move on and work for different clients, some other place, right?

Lisa: Yeah. Do you have an example from your past of a time when you've had to eat some shit?

Jason: Oh my God, I'm sure I've got 80 billion of them. I can say, you know what, I can say, like earlier in my career, I worked on a big retailer, basically this big campaign where I had to bring in a lot of different brands that supported this one product with a campaign to get them all on board. And this never happened before, like meeting, after meeting, after meeting and like, look, I was 24, 25. So I thought it was like the greatest campaign on earth. Is it the greatest campaign on earth? Probably not. But at the time I was like, “this is so awesome.” I had all these people on board and we were going to have this campaign, there are gonna be all these billboards, it’s going to be a big deal.

And the very last second, I think someone from the HR department came in from the company and read some of the copy or some of the headlines and was like offended and killed the whole thing. Not even marketing, like someone like high up in HR. And this was like six months of work and it was a big gut punch. Right? I had to like… it was good ‘cause it was my first like big lesson of like, this happens. And ultimately you're in a business where people come to you because they want your ideas to use creativity to help sell things. But at the end of the day, unless it's your company, you have to go with what the company wants and they have their own internal politics and they have their own things they're trying to figure out. And what you might think is the greatest answer on Earth may not be what ends up going out into the world and you have to be okay with it. I mean, it stung for a while. Then we ended up doing a campaign that was similar in a sense that the mindset was the same, but the, you know, you kind of take all the teeth out of it. So I remember there was a billboard that I used to drive by to work and see, like, every day and just be like, “oh fuck, this sucks.” But you live and you learn.

Lisa: Oh, been there.

Jason: Yeah.

Lisa: Absolutely been there. Yeah. Yeah. And it's like a healthy detachment, I don't know, to let something exist in the world. And you're like, well, did did my best.

Jason: I think you kind of step back from it, too. And again, like it's… it's perspective. Like I, I try to remember like… and I still enjoy this business and I really like it. And am I, as 1000000% fired up as I used to be when I was much younger? Probably not. But you have to remember that and you have to remember for people like, look, it's… it's a gift a little bit to be able to do this and like use your - I say it as like, I get to use my brain the way I want and hopefully put some good into the world and hopefully make people smile. I mean, there are people that want to do this, but don't understand how to do it. Like there are schools to go to and there are amazing portfolio schools and rilliant people all the time come from way different places. I just think sometimes creativity and how you look at things is sometimes a bit wired and some people can do it. Some people can't do it. So like, I just kind of feel myself fortunate to be able to have done it. And if I ccan help other people do it, that's awesome. And… that's kind of it like, you know, we're not, we're not saving lives. We're making marketing, advertising, and communications that hopefully put good into the world. Sometimes it doesn't, but like, you know, it's, you have to keep perspective to keep yourself like a healthy focused person.

Lisa: Absolutely. I always joke about how no one's going to bleed out if we get our color palette wrong, like we're not firefighters, we're not surgeons.

Jason: Right?! And that's a hard message when you like, when you, when you're like, “no! Like this is the right shade of green that says we want to say.” And you know, I'm an art director, uh, is like my, where I started. And it's funny when you want to kind of sit down and talk about art director versus designer. And I, you know, especially coming from like bigger clients and moving fast and getting stuff done. I remember I worked at this agency, and we did a lot of like casino business and I worked with this great designer. And I remember one day he had, he had printed out, like, I don't know - not very eco-friendly these days - but like probably 60 billboard layouts. And it was not even different typefaces, but like different kerning and leading, real minutia stuff. Right? And I remember walking up and he's struggling looking at this giant wall, and I'm like “That one” and walked away. And I saw him standing there for two hours. And like, I love that. I love the designer mindset. I love how you just like nuance the tiny little things. But part of it too is like, that is great. You've crafted this, it’s wonderful and amazing. Let's move on. Let's go to the next thing. And it's like, it's teaching people how to check themselves a little bit, which I think is part of the creative director role.

‘Cause I mean, yeah, I could sit and talk in circles with you about your chocolate bar or your socks and have those really deep philosophical conversations about what people want from socks with individual toes in them. But like, what's gonna, what's going to give people a two seconds smile potentially in like a, a quick digital piece. And then you move on.

Lisa: Yep. Ah, such a good perspective.

Jason: I feel like I haven't talked a lot about like the outdoors and outdoorsy stuff, so I feel like people are probably looking for like, well, what is your perspective on this thing? And I don't know if I have that.

Lisa: Oh yeah. On the outdoor industry?

Jason: Just in general. I think like I was looking at y'all’s site and kind of what you do and… I mean, it's funny because I think what I've used before in the past, and it doesn't have to be… like, great creative is great creative, right? So I hold up Patagonia as one of those brands that just, you know, this is what they stand for. They always stand for it, it bleeds into everything they do. And I don't care if like, it's that, and you're trying to save the planet or you're trying to like, again, like have fun underwear company, it's being consistent and being true and being honest. And being able to do that consistently is what I love, is what I, kind of makes me passionate.

So like, when I see like that, to me it’s the, the benchmark of like how you do this stuff correctly . So I think it's pretty cool that you're into this focused industry of that sort of stuff. ‘Cause it is, it is a lifestyle. It is… you have to get it right. Or people will know you're full of shit.

Lisa: Oh absolutely. The outdoor industry loves calling out bullshit.

Jason: I think that's true anywhere, but especially yeah, there. And I learned that. too. Like, I think what was really cool about my time at Sun Bum was, you know, North County San Diego, Encinitas, like it is a culture, it is a mindset and it is… it is something that is… it's hard sometimes to put into words, but it is like a feeling and when you're there, you're like, okay, I get this. But it is, so is so aspirational. And so just like… I’m trying to think of a good adjective here. So just like, it's very like, you want to eat it up. Right? And I feel like a lot of that is in your, like, mountain breweries or your bike brands or, you know, your hiking equipment.

Like, that was the thing about Sun Bum that I loved was the smell of the product, right? I experienced it before I worked there on a vacation in Hawaii. So when I have the smell, it reminds me of vacation in Hawaii. Right? When you sell things that remind people of what they love to do, or like experiences that bring them personal joy outside of like the calamity of life, that's, that's already a layup. Right? It's getting it, getting it right. What you want to say, but you already have a leg up because people are already passionate about it to begin with. But then the double-edged sword, I see what you're saying is like, well, if you don't bring it and do it right then you're dead in the water.

Lisa: Absolutely. Absolutely. And also the thing with the outdoor industry, like any other product, is like, some people think that… we always ask the question, how fun is your brand? And then what does fun look like?

Jason: Okay. That's cool.

Lisa: You know, because some brands are really recreational, some are aspirational, some are competitive, and kind of like, some people love being competitive. Some people hate being competitive. And so like, we kind of have to go with like, what is fun for the individual and how do we make that into a collective brand voice?

Jason: Smart.

Lisa: Which is gnarly complicated, but also really fun.

Jason: And I get that, fun could be that moment when you've reached the crest of your hike and you have that peaceful thing where you look out into the beautiful vista or it's the Tough Mudder competition where you're sweating all over everyone else. And you've accomplished a goal that you set out to do.

Like it is… that’s, see, that's the strategy stuff I love of the, like the… I enjoyed, I had a philosophy class at Texas I really loved, ‘cause to me, it was really interesting of like, okay, you take people's philosophy, right? I mean, I feel like I'm gonna, you know, get killed here by, by saying this, but like philosophy to me, it was always like, here's people's really smart bullshit that they take from other really smart people's bullshit to create their own bullshit.

And I feel like sometimes in advertising, that's kind of what we do, right? You're crafting really smart, hopefully relevant bullshit that people can get to. So like, what I love to do is that okay. Fun. What does fun mean for you? And then dissect it, right? And go really deep into that. ‘Cause there you're going to just have these conversations where it feels crazier talking about what this product means to fun. And someone says something flippant and you're like, “oh, no, you've just expressed what's really cool.” And we can take that and create a pretty deep campaign that a lot of people will look at and be like, oh yeah, yeah, this is why I like them.

Lisa: Yeah.

Jason: So I like, it goes well with the discovery is kind of what, like, it fuels my fire.

Lisa: Me too. I self-identify as a philosopher more than anything else.

Jason: Oh, nice. Well then I'm sorry. I called the entire… bullshit is not what I meant. I meant people’s…

Lisa: No, it is!

Jason: But that's, that's kind of what makes it interesting. Right? And that's, that kind of comes back to - ooh, look at it. We're circling back. We're being strategic here - of like, what we were talking about earlier was like different people's POV and listening because everyone kind of wants to contribute to the bigger part of the pie. And you have to look at different voices and different perspectives to kind of bring it somewhere different.

Because if I kind of always said the same thing that I thought over and over again, well, my book would look exactly the same and I'd kind of be a one trick pony, right? Like you have to be able to evolve and can draft off others to, you know, grow.

Lisa: Yeah. I think you're a philosopher, too.

Jason: Oh, thank you. I’ll take that.

Lisa: I think you are.

Jason: Yeah. Philosopher, warrior, poet is probably what I should change my LinkedIn bio to. But that seems a little presumptuous.

Lisa: [laughs] A little presumptuous.

Jason: No, I just want, you know, it's like, I just want, again, I just want to work with really smart people that I respect and admire and do things that are really interesting and awesome.

You all do it. Like when you see something like a campaign and you see like this brand did this and they stand for this and you're like, “Damn, of course they did that. That's so great.” And I think people… you know, I listen to a lot of podcasts too. Like I think you were talking about stability. Well, people also these days too, are like looking for like trust, like where do you find trust?

And when you're getting 9 million messages everywhere and you don't even know if any of this stuff is true and who does it come from where? So like finding, being able to trust someone and finding consistent authenticity, I think is super important and something that you have to keep in mind as you move forward in what you do.

‘Cause, you know, you've kind of been handed products where you're like, okay, all right. And I've had a couple of times in my career, I'm like, “guys, we can say this, but it's really more this. ‘Cause it feels like this is total horseshit. And I feel like you're going to get killed.” I mean, you can go the other way, like you're gonna get killed on anything, but there's a difference between like, look, these 60 people are really unhappy or like these 20,000 people know that this is nuts. And like, does this feel good for you?. Like, do you want to say this? Do you want to pay to put this out there? Like, why would we? Let's just do this and this is smarter. Let's have the harder conversation and think about it.

Lisa: Yeah. Oh, that's awesome. Well, I could talk to you all day and, you know, you're very easy to talk to and fascinating. And where can people follow you online? Where can they get ahold of you and work with you?

Jason: Oh, my website is I'm on Instagram at @jtisser, but I haven't posted anything in a while. You'll just probably see pictures of my kids. And that's kind of it, I like to like sit in the back and read what other people say. I haven't been very vocal for a very long time online. I just kind of like to sit back and learn from the show. But yeah, my website, is where you can see if you like what I've done or think I'm a total hack. Again, it's total people's perspective.

But I appreciate you taking the time to talk to me. I know you're super busy, so thank you.


Iris: Thank you so much for tuning in to Outside by Design. This show is produced by WHEELIE - you can find us at our website,

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With that, I'm Iris. Thanks for being here!

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