Marketing That Moves People: Building Brands That Become Lifestyles With Caitlin Choate

Caitlin Choate is the Global Head of Marketing at Boatsetter, a peer-to-peer boat rental platform. With nearly 15 years of experience building disruptive brands, she has led marketing efforts at companies like TOMS, Google’s Nest, Airbnb, and Yumi. Caitlin’s work has been recognized by Cannes Lions and the Webby Awards for innovation and storytelling.

Here’s a glimpse of what you’ll learn:

[2:30] How Caitlin Choate landed her first job at TOMS through a dream internship
[7:39] The serendipitous customer service experience that led Caitlin to work for Airbnb
[14:59] Boatsetter’s model as the Airbnb for boats and the company’s growth trajectory
[22:08] How Boatsetter transitioned from product-focused to experience-driven marketing
[27:45] Caitlin talks about Boatsetter’s approach to lifecycle and category marketing
[33:55] Tactics for building a category versus a brand
[37:33] Integrating PR, influencer marketing, and earned media for unified storytelling
[42:05] Caitlin’s bold campaign ideas
[46:59] How Caitlin builds high-performing creative teams
[56:34] Balancing brand storytelling with performance marketing
[1:02:45] Advice for keeping your team motivated and aligned with your vision
[1:14:03] Caitlin talks about growing up on a boat and her favorite hobbies

In this episode…

Marketing isn’t just transactional; it requires building emotional resonance with customers through memorable experiences with a brand. It’s easy to sell a product, but how do you sell a lifestyle, a sense of identity, or even a community? How can companies balance bold creativity with performance and data-driven ROI?

Brand builder and creative marketer Caitlin Choate believes that connecting with customers emotionally begins by designing marketing that mirrors real-life human experiences. She recommends leveraging user-generated visuals, generating stories that emphasize emotional connection over product specs, and integrating creative, data, and performance teams. Caitlin also highlights the value of running measurable, high-reward experiments to foster brand growth and category domination.

In this episode of the Up Arrow Podcast, William Harris converses with Caitlin Choate, Global Head of Marketing at Boatsetter, about turning product transactions into lifestyle-driven brand movements. Caitlin discusses brand versus performance alignment, using PR and influencers as a storytelling medium, and why cultivating serendipity can catalyze unexpected career opportunities.

Resources mentioned in this episode

Quotable Moments

“Serendipity is not the same as luck… serendipity is so much something you can cultivate.”
“It's not about telling your team what to do. It's inspiring them on what they're capable of.”
“How do we get people to fall in love with the Boatsetter way of life?”
“The brand itself is responsible for 50%... your community adds the other 50% through reaction.”
“Done is better than perfect. The world is changing so quickly; perfection is already outdated.”

Action Steps

Build brand and performance marketing alignment: Unifying creative storytelling with data-driven performance strategies ensures consistent messaging and measurable impact across channels. This balance helps brands scale while maintaining emotional resonance with their audience.
Cultivate serendipity through bold outreach: Asking for opportunities, even when you feel unqualified, can lead to career-defining moments. Proactive engagement opens doors that standard applications often cannot.
Leverage small teams with creative autonomy: Empowering small teams to dream big can yield high-impact campaigns without large budgets. This fosters innovation, ownership, and rapid execution.
Use real-life visuals in marketing: Showcasing authentic user-generated content builds trust and relatability with potential customers. Audiences respond more strongly to genuine moments than to polished stock imagery.
Integrate PR, social, and influencer marketing: Aligning these functions creates a cohesive storytelling engine that amplifies reach and brand consistency. This synergy maximizes visibility and effectiveness across media channels.

Sponsor for this episode

This episode is brought to you by Elumynt. Elumynt is a performance-driven e-commerce marketing agency focused on finding the best opportunities for you to grow and scale your business.

Our paid search, social, and programmatic services have proven to increase traffic and ROAS, allowing you to make more money efficiently.

To learn more, visit www.elumynt.com.

Episode Transcript

Intro 0:03

Welcome to the Up Arrow Podcast with William Harris, featuring top business leaders, sharing strategies and resources to get to the next level. Now let's get started with the show. Hey

William Harris 0:15

everyone. I'm William Harris. I'm the founder and CEO of Elumynt and the host of the up arrow podcast, where I feature the best minds and e-commerce to help you scale from 10 million to 100 million and beyond. As you up arrow your business and your personal life, Today's guest has helped build some of the most culturally resonant brands of the past decade, not just by marketing products, but by shaping movements. Caitlin Choate is the Global Head of Marketing at Boatsetter, the leading marketplace for on the water experiences. But before helping Boatsetter become the Airbnb of boating, Caitlin's creative fingerprints could be found on breakout moments at Tom's nest and Airbnb, where she turned emerging brands into beloved cultural icons. She's a marketer who moves culture by blending strategy with serendipity, storytelling with structure and scrappy with smart. She's launched Olympic campaigns at Airbnb, built viral UGC for Google, owned brands, and once talked her way onto a job at TOMS by showing up to a press day. More on that. Later today, we're unpacking how Caitlin builds brands that unlock identity, community and memory, how she designs high performance creative teams in fast growth environments, and how she's building a marketing engine that doesn't just sell boat rentals, but sells the lifestyle of being on the water. We'll talk about storytelling, scaling, risk taking and the art of shipping. Great work before culture moves on. Caitlin, welcome to the Up Arrow Podcast.

Caitlin Choate 1:30

Thanks so much for having me. Should we just cut it there? I mean, that was a great intro. We'll just end. We wrapped.

William Harris 1:37

Done. Perfect. All right, cut. I do want to give a quick shout out to Amanda Bonacini over at Element Brand Group for putting us in touch. I always like to shout out to the person who put us in touch. And Amanda has been really helpful with a couple of guests now. And So Amanda, thank you for, uh, introduction, introducing us

Caitlin Choate 1:52

here. They've got a pretty phenomenal team over there. Big fan of Amanda's. That's

William Harris 1:56

good, um, the last interruption before we get to the good stuff, I do want to announce our sponsor. This episode is brought to you by Elumynt. Elumynt is an award winning advertising agency optimizing e-commerce campaigns around profit. In fact, we helped 13 of our customers get acquired, with the largest one selling for nearly 800,000,001 that IPO Ed. You can learn more on our website at Elumynt Comm, which is spelled elumynt.com, that said on to the good stuff before we unpack your growth secrets, let's go back in time to your first job out of college, because it leads to an interesting story about how you ended up at TOMS. Yeah,

Caitlin Choate 2:30

it's always a really interesting chain of events. I mean, I don't know if I've actually ever spoken to anybody who has had such a structured career, but my story has a really fun start. And it actually kind of started in college. I went to Florida State. I grew up in Florida. I now live in Los Angeles, and I studied fashion design at Florida State simply because I wanted to do something really creative after a really intense kind of academic time in high school, and towards the end of my time there, my professor had called me into her office and and she was like, so, you know, it's time for you to go off on your internship to wrap up this program. Like, where do you, where do you, what's your dream internship? And I said, Well, there's this really cool magazine in New York City. It's called nylon. Like, there's no way I could ever get an internship at this magazine. It's like, way too cool. And she goes, Huh? She jumps over to her computer, she finds the website, she looks up a phone number, then in there, and literally picks up and calls. And I'm sitting there, like, mortified. I don't know why I was so embarrassed, but I was like, Oh, don't call him. And it turns out, the hiring manager, the woman who was running the fashion closet at the time, was also a Florida State alumni, and she was like, I would love to have another Florida State fashion student come up and be part of the team. And so simply by picking up the phone and asking, I got my dream internship, and, you know, a few months later, packed up my really inadequate jackets in Florida and flew to New York and started this amazing internship. And it had an incredible time, you know, living in New York for the first time and learning about magazines and definitely some Devil Wears Prada moments where I'm like, Starbucks orders and a bag of clothes and and I had actually read about Tom's, the shoe company in nylon magazine, originally, there was this really cool article. It was featuring the women behind TOMS, and it was like, the coolest girls you've ever seen in Los Angeles, like, sun drenched on a silver and I fell in love with the brand, but I also was like, man, it just must be the coolest job to be able to do this article. And it kept it and so while I was interning at nylon, I was doing some writing for the website. The digital editor had noticed that I wear, I wore TOMS all the time, and she was like, I'm supposed to go to this press day for them. Would you like to go instead? And it was like, Absolutely, I must go. And so I remember, I was like. Okay, I need to go to this press day. I need to meet Blake my costume, the founder of TOMS, and convince him to hire me. But I need to really show up like a real editor. It's like 20 years old, right? So I like go to H M, I buy three new outfits like I took this very, very seriously. I show up at the press day, and I'm trying to play it cool. I end up interviewing him for the website, which he was really excited about, because the brand was so small. Was so small at the time. And then at the end of that conversation, I did what my professor had done. I just asked, I said, so how do I come work for you guys? And he was like, Wait, you'd like, know us, you know about the brand, you know really what we do? And I was like, Yeah, I'm kind of like, love with what you guys are doing. And he's like, Well, maybe, like, talk to this person, talk to that person. We'll see how it goes. He's like, Do you have a background in marketing? I was like, no. It's like, Do you have a background in communications? No, fashion design, yeah. But I ended up landing a job there, so I, like, flew home to Florida, packed up my pickup truck, drove across the country. There are less than 30 of us in a warehouse in Santa Monica, working for TOMS at the time, a bunch of young people who just had this dream that we could do something bigger with business, and we had no experience, and we were figuring it out as we went. And it was a it was a blast. And I think that was really informative for me to the rest of my career. And just thinking about dream big ask for that, either directly or have people around you who are willing to mentor you and, like, push you to just ask and amazing things and amazing things can happen. And so I ended up being at TOMS for like, six or seven years, and did a lot of different things while I was there, but really left a big imprint on how I approach my career, and how I approach kind of jumping to different companies and roles and things like that. That

William Harris 6:49

can't be understated, that importance of dreaming big. I think a lot of times, we can't reach something big if we don't dream of something big. There's a song that I like to play for my girls. I've got three girls, and the song is Dream Big by I think it's Ryan Shupe in the rubber band. And it's like, when you dream, dream big, as big as the ocean blue. And I love that song. It just just goes about, like, just dreaming big, because there's so much out there to dream. And if you don't have that dream, the likelihood of achieving it is very low, right? Like, if you have to have to have a target, you have to have something that's there. So I appreciate that about you. You don't just these wild job transitions are not uncommon for you. And so I understand that. There's also an interesting story that goes along with you ending up at Airbnb. I you know,

Caitlin Choate 7:39

maybe I'm, maybe I'm manifesting this for myself. Get a job in a normal way, like they've never just, like, applied for a job and then got a job. It's a good thing. But yeah, the Airbnb story was also a really interesting one, with a lot of the same patterns within it. I was working at Nest at the time. I was running social media for them, the thermostat company. So, you know, went from a fashion magazine to a shoe company to a thermostat company and natural,

William Harris 8:07

that's obvious, yeah.

Caitlin Choate 8:12

And so I booked a trip to trip to South by Southwest in Austin, quite last minute, grabbed an Airbnb, just whatever was available. And the first night that I was there was like, I'm going to be good. I'm going to, like, have an early night. I'm not going to stay out too late. I know it's a marathon, not a sprint itself by and I think the college girls who rented out their room kind of forgot that they had rented out their room. Came home quite late, and I think forgot that somebody else was sleeping in their bed,

William Harris 8:41

like a Goldilocks moment. It

Caitlin Choate 8:42

kind of an interesting I was like, oh, what's happening? And so I emailed Airbnb the next day, and I was like, Hey, I don't really know what you do in this situation, but here's what happened. They immediately get in touch. They moved me to another Airbnb. I felt like it was like, leaving ex boyfriend house. I like, grabbed all my clothes out of the closet, like, packed up my stuff. Didn't want to see these girls. I was like, they're probably embarrassed. Gotta go and and so moved to a new Airbnb, and it was fantastic. I was happy they handled it so well. They handled it swiftly. The next day, I'm sitting in one of these, you know, keynote sessions or whatever, and I get an email from Airbnb, and this was 10 years ago, my ideas, I looked back at this email recently. It was 10 years ago, which is funny, that they also just relaunched. Just relaunched experiences. I feel like this was such an experience at the time, they said, you know, we really just want to make sure that you have an incredible time while you're here in Austin. So on Monday, we want to fly you and two friends in a helicopter barbecue for lunch. Wow, sitting there, like, what, I put down my phone, and I remember thinking, what an excessive use of marketing funds. He removed that. Where is their marketing budget going? Awful idea. A helicopter like you could have just given me like $100 gift card for like, lunch or something, just happy. Right? Like, even that would have felt like too much. And so I go and I like, meet some of the Airbnb team. I take a couple of friends with me. They take, like, professional photographs of the things. So I still have these photos of me on this helicopter. And I remember, you know, like, a couple weeks after that, I couldn't stop thinking about it, and I couldn't stop telling people that story. 10 years later, I'm still telling people that story, and, you know, just kept thinking, there's some sort of wild and crazy magic over there at Airbnbs in 2015 and I think I want to be part of that. And so I threw over my resume. I think it was like, three months later or something, and I was like, I don't even know what you guys are hiring for but I just kind of fell in love with whatever is happening over there, and they emailed me back. They're like, we actually just posted a role. We think you'd be perfect for it. Why don't you come in and have a chat about it? And then I ended up being there for six or seven years, and a lot of a lot of amazing things there. It is funny in the kind of like class orientation, they talked about this drafting thing that they do. They called it the surprise and delight for guests. And they were like, and one time, we flew a lucky guest in a helicopter, and I was like, that was me. And like, you, you're the one. Like, it paid off, because now you came to work here and, like, it's, it was actually a very good use of money, and all these things was like, famous the girl who had gone in the helicopter, but, but, you know, again, it's like you, serendipity is not the same as luck, right? Like, it just happens when it happens, right? Like you can't, you can't really craft luck, but serendipity is so much something you can cultivate. It's something you can design for a little bit more, right? Like, how much are you putting yourself out there? How much are you asking for help? How much are you just picking up the phone? How much are you going to those events and showing up in front of people so that you can allow for serendipity to happen? And I very much kind of live, live by that principle. I've never been somebody who's, you know, this is these are going to be the career steps that I'm going to go down, and I'm going to achieve each one of those. Sometimes it's been like, maybe I should have a little bit more of a roadmap. But for the most part, I think, you know, being really open and being curious and being, you know, pursuing the things that you're interested in, and surrounding with yourself, with people you really respect, allows you to cultivate more of that serendipity, and it can take you to amazing places. And I've been lucky to have that happen. I don't know

William Harris 12:25

if I've already heard somebody say, cultivate serendipity, but I like that idea. I like that expression because, to your point, you can cultivate it by doing the right things, being in the right place at the right time. You can't guarantee that something serendipitous is going to happen, but you increase your odds significantly by doing those things, by just asking for it, right? Totally,

Caitlin Choate 12:47

totally. I think there's some stat I'm gonna get this totally wrong, but it's like Djokovic has, like, the highest number of missed shots in tennis, or something, and yet, I mean, he's one of the best tennis players of all time, and it's just such a good metaphor for you know, we say this often, but you, you gotta, you gotta make an attempt if you, if you want to actually have a win. I

William Harris 13:10

again going back to my daughters, one of the ways that I tried to illustrate this to my oldest, I want to say she was maybe eight at the time, but she was nervous about trying to do something right and failing, and so I crumpled up some little pieces of paper and set up a little bucket or whatever, and I said, Okay, I'm gonna give you five. I'm gonna have five. I want you to go and, you know, take a shot and see what you make it and I think she missed the first one. And then I was like, Ah, man, you missed. I don't want to miss two. I'm just not going to shoot, right? She was like, Why, daddy? And I'm like, I'm just, I don't want to miss right? So then I was like, Are you you go and shoot again? So she shoots. Again, so she shoots again, and she makes that one. And we go through this, and I think she made, like, three out of the five. And I never shot right? So I was like, Oh, you made it. I'm gonna feel bad that you made it. I didn't miss it. So all right, I'm not gonna shoot it again. And so at the end, I said, Okay, let's add up. We got more points. So how many do you get? She's like, you know, three. And I was like, how many did I get? It's like, zero. You never shot dad. And I was like, Yeah, that's the whole point. Is that, like, yeah, you missed some but the only way you can make someone is by taking that shot in the first place.

Caitlin Choate 14:04

You know, I love that so much I have a six year old and I mean, listen, there's one thing all parents have in common. As we talk about being parents, probably so apologies to anybody who doesn't have kids who's listening, who's like, yet again, some parents talking about what it's like to be a parent, but it's the most humbling experience, and it really reminds you of those very simple life lessons, and putting them in very simple terms, and reminding yourself that, like I'm trying to teach my kid how to do this, but am I doing this myself? Am I living by this? Am I teaching my team this? It's, it's, it's, it's a humbling thing, and it's, it's a great reminder of those kind of first principles that we want to

William Harris 14:48

analyze around. Yeah. Okay, so you're now the Global Head of Marketing at Boatsetter. For those who don't know, can you take us through a little bit about what Boatsetter is?

Caitlin Choate 14:59

Yes, we are the most exciting brand that you need to know this summer. We'll just we'll start there. We we are the leading marketplace for boat rentals on the water, experiences Captain led trips. You can kind of think of us like an Airbnb for boats or like a Turo for boats. So we don't own any of the inventory, but we've got an amazing breadth of boats captains experiences on the platform that you can book pretty much anywhere. So you want to rent a pontoon boat on Lake Glenville in North Carolina and drive it yourself. You can do that. You want to charter a catamaran in the Turks and Caicos for a week with an entire crew. We do that too, and everything in between. And so you know me, having been somebody who grew up in Florida and spent so much of my childhood out on a boat with my dad, fishing, camping on islands, camping in the intercoastal, I it's, it's my happy place. It's something that I love so much, but having since moved away from home and not having the captain of my dad available to me all the time, I hadn't really spent much time on a boat, and when I started this role and started learning more about the company, it's like, wow, this is amazing, because there are so many other people like me who love being out on the water and just don't realize that it's actually so accessible to them. And so we've got, like, over 50,000 boats on the platform, 700 locations. We do the sexy stuff really well, which is, you know, the Wake surfing days and snorkeling days and scuba diving trips and fishing charters and all of that. But we're also the only marketplace brand to do insurance. So the stuff that you don't really want to think about, but we do insurance, we, you know, have a great weather cancelation policies. So like, if you're planning to go out and there happens to be a big storm that's coming, you can cancel that trip. It's fine. And so there's a lot of, you know, kind of local operators who do a lot of what we do, but nobody has the breadth and depth of inventory that we have. An incredible Captain community. Our guests love what we do, and it's growing like crazy. So it's, it's been, it's been a lot of fun.

William Harris 17:13

You mentioned wake surfing. I'm in Minnesota, so boating is a big part of what we do out here as well. 10,000 Lakes actually more than that, I believe. But when I learned how to wake surf for the first time, I learned from somebody who did not have knees, he actually had his legs taken off in a boating accident. Yeah, obviously not through a boat set. Clarify that, but this is something that was tragic, but then he ended up getting back up on to his feet, so to speak. And I see that you have the the Olympics back there. He ended up going to the Olympics, the Paralympics for snowboarding, but he's the one who ended up teach, taught me how to wake surf, and he could still do it way better than me and anybody else I know. And he's doing 360s out there, which is absolutely incredible. And so I at least share that I resonate with your passion for boat life here in Minnesota, it's a big deal here as well,

Caitlin Choate 18:07

yeah, in a lot of places. And I think what's really fun is boating culture in Miami is very different than boating culture where you are is very sure. And Lake Travis in Austin is very different than Lake Norman in North Carolina. It's very different than, you know, taking a boat out on the Hudson in New York. But there's this kind of common, common red thread throughout all that, and the people who wanted to get out on the water, which is, it's a way to get outdoors and to spend time with people that you love, with just the people that you love, with just your friends or just your your family to try something new. You know, I think that, like, what's been so interesting to see, especially coming out of COVID, is seeing people just get so turned on to really new interest. It's like sourdough during COVID, right? Like people with, like, is anybody still making sourdough? I actually did meet a guy a month ago who, I guess, makes great sourdough, like, Did you started the pandemic? And he was like, yes, like everybody else, but like, I think social media has turned us on to these niche communities, these niche interests. My friend Sarah Wilson talks about this all the time. I think it's really brilliant in that, like, what the social media space and Internet has unlocked is just this ability to go deep on these niche interests and have really strong community around them. But those interests then become hobbies, and then those hobbies become your lifestyle, and your lifestyle is your entire personality. You know, it's like sourdough became people's entire personalities. And kind of similarly in what we saw with people wanting to get out on the water. I mean, you can learn how to sail on boat set, or you can learn how to weak surf. You can kind of learn how to fish. Maybe it's something you did when you were a child that you haven't done in a long time, much like my story, that now we're turning people onto. And so Gen Z is actually our fastest growing segment, and I think it's. Lot, in part, because of these kind of unique activities and these niche interests that people really want to explore. And, you know, I don't know if you're following this, this guy, Phoenix, who's sailing from Oregon to Hawaii right now. I think he's quite million, a million followers in like, two weeks or something. Wow. He, you know, quit his job and got a sailboat, had only sailed in a river, and now he's sailing across the ocean, and it's like, that's the Boatsetter way of life. And more, you know, more and more young people are saying, You know what, I want to go do something out in the world where I can try something new, and really have to learn it deeply. And know it's not the typical career path, but who cares? And it's like we want to enable more of that. And it's really fun to see people doing that on the platform. I

William Harris 20:47

love that you called that out. That is a trend that I think that I'm seeing as well, of people getting out away from social media to do things IRL again, and it's a really good trend. I want this to continue. Let's please all do more things in real life together, getting together with other people, doing experiences. My wife and I talk about this a lot where, you know, it can become very easy when you're older to just say, like, hey, date night is we're just gonna go to get food. And that's fine. There's nothing wrong with that. But it's like, can we build some memories? Can we do something more than just going and talking about the things that we used to do, and let's start talking about the things that we're doing right now today. So I think that this is a great way to do that.

Caitlin Choate 21:25

Yeah, obviously going out on a boat, much better date and, like, probably more affordable than you realize, especially if you're going out to dinner in LA or New York or Miami. Just an extra idea for you, go karting, also really fun. My husband and I have gone party on a date before, and if there's any ounce of competitiveness in you, we had a lot of fun to get that gown on a racetrack and try and go fast and beat each other. That's

William Harris 21:52

good. That's a lot of fun. We do like to compete, so that's good. I will. We'll have to do that. So I want to talk because you've been talking about how, you know, interestly to hobbies lead to lifestyles. How? How do you unlock this idea of marketing experiences versus products?

Caitlin Choate 22:08

Yeah, it's a great question, and it's something that was maybe one of the most, most motivating factors for me to kind of come to Boatsetter, because when I was looking at this brand, you know, it's been around for 10 years, and they figured out a lot of the hard stuff, like insurance, which I had mentioned earlier. There's a ton of great inventory on the platform. There is an amazing team already in place. Who knows this industry inside and out, and knows boats that are inside and out. So there's a lot of things that kind of were already put into place. But so much of how the brand was positioned before was around boat rentals, boat rentals, boat rentals, Boat Rentals. That was the language, that was the positioning, that's kind of what you saw it on the surface. And again, it's about what you're going to do out on the boat. It's more it's a much more emotional purchase. It's, yeah, your your son just got certified for diving, and now you want to do a trip where you're diving off of a boat for a few days, and that's a core family memory for you. Or, you know, you want to break out of the normal routine and learn how to wake surf this summer. Why not? Or you want to go take your kids snorkeling for the first time. And so that experience positioning has been a really big one for us, and the main way that we've really showed that off to the world is visually through the photography that we do. And it's just massive shout out to our very tiny creative team. It's essentially two people who are producing the output of a team of 10. But TIFF, who's our art director, and she's also a photographer, and she's an editor, and she does all these things, just came with such an amazing perspective on how we can use photography to really reposition the brand. And when I think about how we are a marketplace company, and I mentioned this a few, times the breadth and depth of what we offer is incredible. That is a benefit, that is something really unique to a marketplace business. It means we don't do photo shoots like a typical brand does. You know, it's like, I'm not selling chapstick. So we're going to go, you know, curate the photography for this Chapstick and control that whole environment. We don't control a lot, a lot of what your boat day looks like. You're going to go out with that owner and maybe have this kind of experience. You're going to go out with this other captain, have a slightly different experience over here. And so how do we capture the diversity of that? And so what we've really done is just connected with a lot of amazing photographers, up and coming photographers, oftentimes in markets that we really care about. And we say, go out on a boat day and have a great time. We don't really have, like, a strong shot list. It's like, we need some of this. We need some of that, but just like, have a good time and show us what you get back. And so the photography on our homepage, in our marketing assets, across our social are all from real people who have had real trips. And it's best case scenario when a finger gets in the way. Or there's a splash on the camera, or the shot isn't exactly positioned in the right way, because that's the reality of what we do every every day. And just being out on the water right? It's probably going to get a little messy, you know, your sandwich is going to get a little soggy, but sure, you're going to end up with sand everywhere, you know, and salt water in your hair. And that's all the the beauty of being out on the water. And so I think when you're you know, with a consumer brand, really reflecting on what is the most genuine, authentic consumer experience that people are having with this thing, and how do we bring that out to the world and not try and polish it anymore, just like very authentically? Here's what you're going to get. Because I think that you know to what we were saying. You want to kind of get off of the Polish and the everything of this, the digital world, and you want to get into real life, which is kind of messy and unpredictable and can be very serendipitous and and so we really try and craft that through all of our all of our marketing, and especially visually,

William Harris 25:59

authenticity is huge. And I think that one of the things we struggle with, when you think about, let's go Airbnb, renting a home. We have a lot of experience living in homes, and so most of us feel pretty comfortable with what we're supposed to do there. A lot of us have a lot less experience on a boat. And what we can do there, what we should do there, what's acceptable, et cetera, right? Like with a culture, we have less experiences there. And so, to your point, being able to show these authentic moments makes it more approachable to somebody to say, oh, I can see myself doing this, because I can see somebody else who's also doing this, who probably doesn't have much more experience than I do on a boat. Yeah,

Caitlin Choate 26:35

exactly. That's a really great point. And I think that goes back to, you know, we were talking about a little bit earlier too, in that it's Boatsetter is, is not for, you know, the hardcore Well, we are, this is the benefit. Like we are, we can be for the hardcore boater who knows how to drive a boat. I mean, our we've got an incredible team of people at the company who are those like hardcore boaters, who have been captains in all countries in the world, who are like naval engineers, who are like award, you know, trophy winning sports fishermen themselves. We are for that audience, for sure, but there is this much broader audience of people who I just want to get out on the water. I love being there. I'm not totally comfortable maybe being on a boat, but you don't have to drive. You don't exactly have to know. This is what our owners and our captains are so great at, and they're really supportive and kind of supporting us, and what they what they need, and what to bring, and what's allowed, and how to make the most of their day. Yeah,

William Harris 27:34

that's good. How do you work in the idea of, like, the whole lifecycle in the marketing funnel? Because you guys are doing things all the way throughout this with people.

Caitlin Choate 27:45

Yeah, we it's interesting that, like our biggest challenge, from a marketing perspective, is people really just knowing that we exist and so but there also are a lot of people who are searching for boat rentals, actually. And again, this is kind of a trend you see towards outdoor adventure and outdoor activities coming out of COVID. And so we try, and, you know, it's such an overused phrase in marketing, but I'll use it to meet customers where they are, right? So we do a ton in our performance marketing side of things, where, you know, capturing that demand as people are searching for boat rentals on on Google. But I also think, you know, search has changed so much, we really think about our social channels as search. So sure, a ton of people still go to Google and search for things, but they're looking for things on Tiktok, they're looking for things on Pinterest, they're looking on for things on on Instagram, and you need a slightly different strategy there. And so we do a lot in our organic social marketing, influencer marketing, so that when we're working with, you know, a travel influencer in Florida who's known for the best things to do on weekends in Florida, you know that content is showcasing Boatsetter, and then we show up in that search on Instagram when consumers are looking for what to do. And so there's a ton that we're just trying to capture, the demand that already exists. But then there's this whole other side of things, which is also growing the category. So I want you to know that Boatsetter exist, but I also want you to know that you can get out on the water really easily, more easily than you've ever been able to before. And so that's really been the confluence of our organic social influencer PR, working together to grow that kind of broader awareness. It's one of the first things I did when I got here, was bring in a PR agency who just really understands the connective tissue across all of those things and can help design programs and moments that capitalize on social influence or content. PR working together, and that's where he's seen a ton of our success in kind of growing the category. And I think, you know, sometimes it's it can, you know, marketers get so focused on growing just their brand, but kind of, every brand that I've worked for has been completely disrupting their category or creating an entirely new category. Category, and so you think about like this list, the tides for all of us. I genuinely try and not use boat puns, but

William Harris 30:08

that's a good one. It

Caitlin Choate 30:10

really does like lift the tides for all of us, we just want more people to get excited about spending time out on the water and realizing that's possible, and then recognizing that Boatsetter is the best way to do it, Boatsetter is the safest way to do it, Boatsetter is the most reliable way to do it. Boatsetter is the most fun way to do it. But there's also just this category growth challenge that we that we think quite a lot about, and

William Harris 30:34

I love that idea of building the category versus just building the brand. I don't know if this plays into it. But I remember you guys talked about launching a 40 page magazine, kind of by accident, like, how does that play into, let's just say, building that category versus even just building the brand? Yes,

Caitlin Choate 30:50

that's such a fun story. And again, a testament to our creative team and and what they're capable of. So we, last fall, were thinking about just how we could get some really interesting storytelling into organic social so, you know, it's kind of off season at that time, a little bit things are slowing down, like, what are some really interesting stories that we can pull together about owners or captains or destinations that might not be top of mind for you, you know, in November, and as we went story hunting for those moments, it kind of quickly expanded into a lot of content like the original intent was, oh, to be cool if we make like a digital mini zine. Digital mini zine became, became 40 pages of content that was so phenomenal. After we saw it all together, we were like, Well, shit. Now we have to print this so magazine in less than three months from start to finish, with a team of two creatives, some phenomenal freelancers. I think tiff grandfather was one of the contributors to is, like a very friends and family kind of initiative, a friend of mine, Josephine, in Hawaii, he was amazing ice cream shot there, went out on a boat with her family and and the main objective for the thing, which has really become what we've used as our prompt for all of our marketing now, is, how do we get people to fall in love with a Boatsetter way of life? And it's that like you flip through these pages and you hear from you know our owners down in San Diego who are award winning documentary filmmakers on marine wildlife, who take you out whale watching on their boat, like you and just your family, or the captain in the Keys, who has General Patton sailboat. It's called when and if, because General Patton was like, if I when and if I come home, I'm going to sail this around the world. He never did, but this particular Captain Seth is planning to by 2030 and then experiences like, you know, my friend Joe, who went out in Hawaii, who had lived there for a couple years, but hadn't been out on a boat yet, actually, and it gave her just a totally different perspective of her local area, and what it offers in this vantage point of, you know, kind of seeing Hawaii from the shore and and just having this amazing experience. And so that magazine is really a North Star for us in a lot of ways. And like, how do we come back around to that in a push notification, in a social posts, in a PR headline? Are we inspiring people to fall in love with the Boatsetter way of life, and it's just been a really great kind of anchoring point for us, and and it looks awesome, and it's fun to share with people. And I can't believe we made a 40 page magazine.

William Harris 33:32

That's so wonderful. So take me through some of the other ways that you guys are helping to the actual tactics that you're doing on how you're building up the Boatsetter brand, how you're building up this, this lifestyle to the point where other people want to get involved? You're building this as a category? What are the things that not just you, but other brands that are trying to do this in their categories? How can they approach this? Yeah,

Caitlin Choate 33:55

what? That's the million dollar question, right? It's the 100 million dollar question, what are the right tactics to put in place, and where do you spend your time and money? I think you know, first and foremost, marketing or building a business. It's a team sport, right? We have to have such a tight, close, trusting relationship with our other partners in the organization, one of which is a huge one for us, is our data and analytics team, like the number of conversations we have with our data and analytics team, the visibility we have into what's actually happening with the business and where we need to grow demand in particular markets, and how we evaluate the demands that we're bringing in. What does the channel mix look like? How does our conversion rate get impacted when our channel mix changes? I've candidly, like, never worked in an organization where we had this mature of a kind of data practice and harmony with our marketing, and that's what enables us to do these wild and crazy big ideas, like make a magazine or some of the other things that that we've done, because it gives us confidence in this is the kind of tech. That moves the right kind of needle, and we can follow that with the right payback period to understand its real impact. And I think that's really hard for marketers. I mean, you think the marketing space is it kind of always flip flops back and forth between brand and performance and brand and performance, and those two words themselves are inadequate for really describing you know how those both need to work together. But I think you know deeply understanding the data and being fluent in the business side of things unlocks those amazing brand moments. And then how you complement then that, then with performance. And so the first thing I always start with is like, how's your relationship with your data team? What kind of data do you have? How much are you skeptical about the data that you have? Do you feel like you have a really strong thought partner in deeply understanding the ins and outs of the business and the way that the CEO does so that you can kind of stand in those shoes for a moment and then make a call around what the right marketing bets are, because everybody's marketing mix is going to be a little bit different, right? So I think often about like percentage of our marketing budget. If some wild and crazy idea is 1% of our marketing budget, I feel pretty good if my gut instinct says we should do that thing right. And 1% of a marketing budget for one team might be $10,000 for others, that might be a million dollars, but you have to right size it to your business, and kind of the risk level of, kind of where you're at, and so, you know, with the relationship with your data team, understanding the business inside and out, I think is like a really essential place for marketers to start, because that doesn't just lead you to more performance marketing, that leads you to confidence, to building the brand In the way that it should be built, with those two levers working best together, brand and performance.

William Harris 36:46

Yeah, I had a couple of weeks ago Jesse aloof over at tire agent on and the thing that he called it was brand performance. And I hadn't heard that term before, and I liked that term. It's like brand and performance together, working together. I got to ask, though, what do you think is the estimated payback period for flying on a helicopter? I

Caitlin Choate 37:08

don't know. I spent a lot of money in Airbnbs over the past 10 years, so I think they more than made their money back, more than their money

William Harris 37:14

back. Something else you told me that I really appreciated was this idea of like, how does PR influencer and earn media actually work together at this stage, and what makes this integration hard? And you talked about how you know they aren't separate. They do have to work together as one integrated storytelling edge. And tell me a little bit more about how those three work together. Yeah,

Caitlin Choate 37:33

we our PR team is a pure extension of our team, and that's first and foremost, is that the more that they feel invested in our business, close to our business, understand what we care about, that's going to allow them to move as fluidly with us as we need them to, to keep up with with the pace of things. And that's not true just for this kind of tactic. I think really great agency relationships should be those in which that team feels inspired, motivated, excited, compelled, like deeply integrated with totally and I actually think it's one of the things that remote work makes easier, right? Like in a in a physical office environment, you've had a bit more of that divide, maybe your agency teams would come in once a quarter or once a month. Now it's like, we can be on Slack together. We can be in zoom calls together. Good point part of the practice. I think, you know, maybe that's one of the things I'd attribute to some, some really strong agency relationships. But we, you know, we keep them informed of everything that we're doing and looking for those opportunities. And so when we're crafting, you know, our influencer list for the summer that's going back to them for feedback, that's going back to them to like, what? What are the kinds of people we need to get out, and then once we get that person out, okay, the contents live, share it back with our PR team. Can they go pitch that anywhere? We had a great opportunity last summer. Jessica Biel went out on a boat in the Hamptons. Actually came together, as these things do really quick. It just turned out she needed to get out in the water. We could do we had amazing boats. Got her out there. She had a great time. She posted on social about it, which was phenomenal. And we weren't expecting that, but that became something that's a proof point for the brand in earned media. And so, you know, how do we ensure that we have the right relationships that were top of mind when the right people need to get out on the water? We can do that really quickly, and all of the right people know it's happening and then leverage that as an asset thereafter. And so there's just so much in the trust and finding the right partner, and really making sure that the routines and the practices you have allow you to move that quickly on things I love, for the

William Harris 39:49

success, I love that you talked about, like bringing the communication together. I think that's an important piece of this, where it's like, whether it's slack or whatever, but you they don't feel like disconnected teams anymore. I think. That's a big part of it. And then you've talked about data just a little bit ago, too, and I think that that's a big thing that we've noticed, at least at element one of the ways that we found for us to be the most successful for our brand is if your goal is not top line revenue, if it's EBITDA, we need to know what your P and Ls are. We can't optimize towards something that we don't have access to, or at least something that's analogous to it. And so to your point, I think I'd say, having that communication of the right things being communicated to the right teams, and having all those teams on the same page, that makes a big difference between whether or not you can work as one orchestrated team, or not.

Caitlin Choate 40:31

100% I think, something that I think about quite a lot and is maybe the most important piece of advice, I would say, for anybody, agency, internal, senior, junior person on the team, is context. When people have context, there is trust. You can move faster. So it's not about, you know me as as as a leader coming in and telling my team what to do. It's here's the context of how I'm thinking about this thing. So then you are therefore empowered to arrive at the same conclusion that maybe I would with an agency team context, with your own team context when you're trying to manage up context, like rather than just telling people your perspective or what to do, really helping them understand how you're seeing things from your perspective, and giving them that context is just a huge communication skill that I think is kind of can be really transformative.

William Harris 41:34

Yeah, you're you're in a niche that allows for some much more interesting content. I think that there's, you know, if you're selling, you know, computer cables, i There's only so much you can do creatively with that, but you're in a spot where you can do some. So what are some, just wild experiments that you've either tried or that you've wanted to try, and you're willing to talk about?

Caitlin Choate 41:57

Yeah, I by my team, if they were listening to this, would roll their eyes and be

William Harris 42:03

like, That's a good one. Let

Caitlin Choate 42:05

me give you the laundry list of crazy ideas that Caitlin, at 10pm you know, sent over on a on a slack this thing. I think I like messaged somebody on our team the other day. I was like, grab the handle. Lost at sea, I'll tell you later. And she was like, what's happening, and maybe more to come on that, but it's not available. But if you have it, we want it, let's talk. But I you know, the magazine was certainly one of those just kind of bigger bets, and we have a way too small of a team. We don't have nearly enough time. We have a really small budget. Who are we to believe that we could actually pull this off. And we pulled it off last summer, we did a whole week of $1 yachts. So, you know, we think very much about like we can put our marketing budgets into traditional advertising. We could also put our marketing budgets into just getting people out on the water. So let's do a whole week of $1 yachts and kind of drop them, you know, and promote it through our push channels, or through our social channels, and just get people out on the water more easily. So that was really fun. We've done this tactic a few times where we call it our collection series, where we kind of work with our owners to just design really incredible, special boat days. Our summer collection had like an oyster tasting out on a catamaran here in LA and a private concert on a floating Saloon in Austin and some other things. And those were each $100 and so just dreaming up like what is possible on the platform has not only been awesome, awesome for our guests, but our owners get stoked about this stuff. Like our owners are like, what if we did this, and what if we did that? And then I saw in the summer last year, you did this. And so it's helping them dream up what's possible on their boat, both for these campaigns, but also just every day, right? Like you can do an oyster tasting on a yacht, actually, anywhere, anytime of any time of year on any kind of boat, and so it's inspiring our owners to really think in that experience first way. And then there's this one obnoxious idea that we haven't we haven't done yet, but I have brought up quite a lot, as you maybe you can tell me if it's a good one. William, I really want like sand castle artist replicas of 100 boats that are on Boatsetter down south with like, QR codes, where you can actually, like, scan the code and book the boat, but yeah, you just showcase all of the cool boats that are on the platform. And it's seeing Castle artists are, like, amazing, yeah. Like, what a cool job to have, and what a what a neat thing. So I don't know, maybe some sand castle art will come down.

William Harris 44:46

I love the idea of, you're asking somebody who gets very easily excited about everything. So I'm maybe not the best judge of that, but I think that's a really fun idea. I do. I like seeing when somebody does something like that, where it's like, I don't know. Know that I've seen anybody do any like massive sand castle art activation like that, and so I think that would be really fun, right?

Caitlin Choate 45:07

Or just more GoPros on dogs doing yacht tours. That's the I want a tour of the yacht, but I want it from the perspective of really adorable little Collie who's just running around trying to figure out where the treats are so but again, it's like we think about this too, just in terms of our brand persona. And back to that point we were talking about with authenticity. Being out on the water can be a little messy. It can be unpredictable. It's also a lot of fun. It makes you feel like a kid again, right? You can be the most serious person in the world, but the moment you get out into open water and you stand up on the side of the boat and you go, woo hoo, and I'm gonna jump in, you turn into your five year old self again. And that's why it's our happy place, for so many of us who love being out on the water, right? And so that's part of our brand identity, that's part of our personas, to just like, have a little bit of fun with it. We, you know, we, we take the safety part really seriously, and again, that's why we have, like, the boat sitter promise and insurance and uscg certified captains and all of that. But there's also just this unlock and like, have fun, be silly, feel like a kid again. And that's an amazing thing to be able to leverage is part of our brand.

William Harris 46:23

100% of the time I get on a boat, I have to do a backflip off the boat. And my wife always laughs every time. She's like, you know, rolls her eyes, but in a loving way, kind of thing, she's like, Yeah, he has to do this every time. One of the things that you've talked about, that you're passionate about, is really building the right team. And building a team in this high growth environment, it's one thing to have the right strategy, but you also do need the right team. I understand that you have some unique ideas about building this team to scale. Tell me a little bit about these ideas. Yeah. I mean, I think,

Caitlin Choate 46:59

listen, I think one of my strengths, one of the things that I'm really good at, is getting a lot of output out of a small team. And I think it's one of the reasons why I've been able to thrive in these smaller environments that are growing really fast and trying to figure out, you know, where this rocket ship is going to go. And I think it's, it's a lot around again, it's not telling your team what to do. It's inspiring them on what they're capable of. And I think that that is something that really works with small teams that have huge ambitions and, frankly, need to achieve a lot for the business. So it was really cool, like, even back to the magazine part. The copywriter that we have on that she ended up applying to an NYU modern journalism program, because through the exercise of making the magazine, she was just like, Wow. I didn't, I didn't realize that, like, this is what editorial means. And I was actually really energized by and I had a lot of fun. She got accepted into the program, wow. And so I just, I love wins like that, where it's like, let's dream a little bit bigger. Let's like, see what's possible. Let's push ourselves to the edge on what we can produce and what we can make. Because ultimately, yeah, maybe you wish you had a few more hours in the day, but then you get to stand back and say, wow. Look at what we achieved. Look at what we pulled off together as a team. And so I think really having the right kinds of people who are motivated by that and excited by that, and kind of love to work in that ambiguity, and kind of want that push to go a little bit further, like you need that in every single person on a high performing team. And I think we've really got one at Boatsetter. And I think, you know, another big part of that is how we, you know, like design for creativity. And, you know, we kind of use creative as a shorthand for, like, a team within the organization, but creativity needs to be a superpower of a small team flat out. Like and again, that goes back to the integration of PR content, social influencer all together, you are going to get disproportionate reach and better earned media through ideas that break the system a little bit, that you make a bet on, that are disruptive in the right ways. And so creativity really needs to be a superpower of every single person on the team, even our performance marketers and our analysts and so I think, you know, another thing is, just like, I overuse that word a lot, is there a creative way for us to think about the measurement model for this? Is there a creative way to take that ad set that was working over there and just remix it a little bit for this other learning we're getting here? Is there a creative way that we can think about local events strategy that just totally flips the thinking on its head around that. Because I want every single individual to realize that they you know again, I want them to study the business. I want them to understand the business inside and out. I want them to be fluent in the data. But I want that to all be an enablement for you. These big, crazy ideas that we get to go chase after. So I think it's some in, you know, having the right team who's really energized in the work in the right way, and keeping them motivated and inspired by the work, and really proving to them what they're capable of, both as individuals and as teams, kind of, you know, overusing that design and creative and that inspirational kind of language, because I think it just helps it be better woven into the team and our language. And then we have some routines that, like we really guard quite a lot, like creative reviews. We do two times a week. We spend two hours together each week looking at all of the creative that we're producing. And the marketing managers are there giving feedback on it, and our creatives are there sharing the work. And there's some brainstorming that happens sometimes in there, our product team will come in when they need something, you know, from us, that we need to develop for them. And that's a really important, you know, that doesn't move, you know, two times a week we do that for two hours going through the work. And I think that really, that really helps set the tone for what we care about as a team. I

William Harris 51:03

think that's important. I love the brainstorms, the creative reviews. Whenever we're looking at Creative for a lot of our clients, one of the things we do are the creative brainstorms. And when they ask, well, who should be at this brainstorm? I'm like, Well, you, obviously, but then beyond you and your creative team, I want your customer service team. I want your spouses like they hear you talking about this and complaining about it, they're likely thinking about these things as well, like, like anybody that you think can offer some creative insight that you might not be seeing. Because I want to see this from a lot of different perspectives. And to your point, I think that makes for better brainstorms. I love that you're asking people how to think creatively about solving all types of problems, aside from just asking that, I think that it's important to acknowledge that you, and you've called this out, you have to hire the right people. Then I had someone on here before that talked about how her name is Tim Webster, about how, if you genuinely believe that solving the problem the best way to solve a problem is by hiring more people. If that's in your core belief system. Then, for instance, you asking, well, how can we more creatively solve this it's not going to resonate with you right because you're going to say, well, that's not the right way we need to solve this problem. And so you have to hire those people who have at least a similar mentality that say, I want to find the creative solutions to problems. Now, when you say, hey, wait a minute, is there more creative way that we can solve this? Now, they say, oh, yeah, I want to spend my time thinking about how to do this, because I also value that as a solution to this.

Caitlin Choate 52:30

Yeah, I love that. And I think that kind of reinforces the point that creativity, or being creative, has a lot of different definitions to it, right? It's not just I know how to paint, I know how to design or write, right? But like, if you are a curious person and you are willing to be, you know, bold and sharing your ideas, that's creativity, you know, and and listen again, we're in an industry that we're trying to disrupt, like there's not a rule book for us to follow here. We can't, we can't follow the old rulebook. Like we need to think outside of the box and think outside of the lines to figure out how we how we move this thing forward. We're never going to have enough money, we're never going to have enough time, we're never going to have enough people. That's true in a small organization, that's true in a big organization. So you know, you really have to kind of put on a different hat and think more creatively about how you solve problems, and also, today is very different than yesterday, right? And that's, you know, another thing where it can be a little bit messy, you know, and how you come up with ideas and put them into practice. But if you're looking to do everything super pixel perfect. It's out of date the moment you bring it out into the world, because the world is changing so quickly, and so you've kind of got to be willing to put things out there and let consumers react to it. I mean, that's it's kind of like a scary part, but I think a really fun part of marketing, and I think, given I started my career in social I've always been so comfortable with, which is the brand itself is responsible for 50% of the work that you put out in the world, and the way in which your community responds to it, adds to it, fuels it. That's the other 50% and you have to be open to that. You can't just force your message on people anymore. Your community, your audience, the broader population, is going to put their imprint on it, and sometimes a really great way, and sometimes a really terrible way, or a way you couldn't predict, and you have to figure out how to navigate that.

William Harris 54:28

How do you navigate that if somebody ends up putting out something that's not good, and you're like, this is this is not we've got a problem. How do you work through that?

Caitlin Choate 54:37

I you know, you call your crisis management team, and you figure out if it's really a crisis, you know, it's, I think the way not to do it is maybe, you know, it's just all of the conversation around Blue Origin, for example, they had crafted a narrative and a campaign and a plan that they thought was bulletproof and really great, and then you put it out into the wild, and everyone else thought. Otherwise, sure. And so, you know, one path is you just stay quiet on that, which is, you know, kind of very much what they did. But then, you know, it's funny, the HBO Max rebrand that just came out yet again, so, and then it was, now it's back to the HBO Max, the campaign that they put out around that is so brilliant. Like, I think their Instagram account right now says, like, these rebrands are killing me. It just recognized the tone in the room that, like, everybody thinks it's ridiculous, that like, oh yeah, no shit. You should have just stayed with HBO, and now you're coming back around to that. And yeah, but that comes back to, like, even a data point and the integration of social from a data perspective, because social media is this amazing data set of how people think about your brand, talk about your brand, comment on your brand, and that's great data points for how you design campaigns, the language you use in campaigns, the things that you remix and then put back out into the wild. And so I think, you know, the HBO maximum is just a really great example of somebody reading the room in the right way and capitalizing on that.

William Harris 56:10

Yeah, that's good, acknowledge it, right? And to your point, find out if it's actually even a crisis, because it might only be a crisis for the CEO who just doesn't like it. But the reality is, the consumers might love it, and this is a good thing 100% How do you protect creative thinking in a performance driven environment? Because a lot of us are still coming from a very performance driven environment where it's it has to produce.

Caitlin Choate 56:34

Yeah, yeah. But see that comes back to like, brand tests to produce, to performance has to produce. It all does, you know, I think there really is something to buy in. It's one of the reasons I, you know, I was also really excited to come to Boatsetter is we have a CEO who has buy in on brand. I have a lot of friends who are working in brand roles with leadership teams or a board who doesn't understand it, and that's really hard. That is a really hard argument to make, because it does take some leaps of faith to figure out what works, but you can, you can do those in smaller environments, like I'll give you example. We we've been really trying to figure out the impacts, the potential Halo impact of paid social on our local marketing campaigns. And what we did was we ran some campaigns in quite small markets, like Spokane, Washington, for example. There's a great lake there, really great for boating. And we ran paid social for, you know, a very again, this comes down to percentage of your marketing budget, right? A very appropriate level of spend in that market with a strategy that we felt really good about. If it totally failed, it wasn't going to take the business, but if there was a win there, it was going to be really insightful for us. And so we designed this in partnership with our data team, ran that test and then looking backwards at kind of what happened. Not only did our traffic, of course, grow from our paid social campaigns, because we were watching everything, like view through rates and click through rates and remixing the content to make sure it was really performing for for those, those specific near term metrics, but also, we were able to see this halo effect on our direct or direct traffic, our SEO traffic, our sem traffic, when we were spending More on the brand side of things to really generate more awareness and consideration for Boatsetter in that smaller market. So then we're able to say, Okay, well, that level of budget, we were able to penetrate the Spokane market by about 30% because it was quite smaller, okay, what's 30% of the New York market? What's 30% of the Miami market? Okay, we'll need a million dollars to do this in Miami, instead of $10,000 to do it in Spokane, or whatever those numbers ended up being. And so there's a very data driven way of approaching measurement, incrementality, all of that on the brand side of things. But you kind of got to break out of your, you know, performance marketing constructs of payback periods, right? Like you're not going to see it in a day. You're not going to see you're not going to see it in seven days. So again, right size for your business. What's a test that you can run? Work really closely with your CEO, with your data team, with your measurement team, to understand the the things that that test needs to produce, and then let it run at the right level and go back and scrutinize that and see what happens. And I think more times than than not, you know you're gonna see that the brand stuff often works if the creatives really good and the audience strategy is really good, to get all that that stuff right too. Because I think most of us who are wrestling with that conversation aren't trying to go from no brand marketing to a $10 million TV campaign, right, right? We're trying to take baby steps towards some other brand marketing activity that's going to allow us to have a more balanced brand and performance marketing mix. So I find those incrementality tests and those kind of smaller baby steps along the way that can give you a really strong signal are. The way to go. Then you get buy in, and then it's a lot easier than, you know, just trying to convince somebody of your beliefs.

William Harris 1:00:06

Yeah, well, I've always said My goal is to get your CFO to say that you need to spend more money. If the CFO is completely convinced that this is worthwhile and saying, why are you not spending more? We've done a good job. I had Preston Rutherford on here, who was the CMO over at Chubbies, and he's put together a tool. I don't remember the name of the tool. I wish I had it handy right now. I'll try to add it in the notes. But a tool for doing exactly that, trying to do a better job of measuring that halo effect from branded performance type creative right where it's it's technically brand, but it is driving performance. You just have to look at it differently, because I think that's a thing that a lot of brands struggle with. One of the ways that we try to approach it, which can be slightly disruptive, but it is very concrete, like you said, from an incrementality standpoint, is just the geo holdout. It is, to your point, it's like, let's run this in Spokane. Let's actually see what happens. It is still the gold standard. It is still one of the ones that we like to do, but it can be a little bit disruptive to some brands, if you're you know already in 99% of the market, you're going to hold out 20% of the market. That's that's tough,

Caitlin Choate 1:01:07

totally, totally. And I think another thing it just to remind people of this almost comes back like full circle to the beginning of this. And just ask is, I find marketers, maybe this is true in other functions as well, but I've only ever worked in marketing, but marketers are so willing to help each other out, and this is where things like LinkedIn and social and all of that is so great. And like, build your network of other marketers, the number of you know, other friends and other marketers that I call it. How are you guys handling this? Are you seeing the same thing in the in similar industries and other industries, people who are CMOS, people who are junior marketers, like, leverage your network and just ask. Because, again, it's like things are moving so fast and changing, and the technology is changing and the measurement models are changing. And if you feel like you don't necessarily have that like, really phenomenal knowledge. Internally, there's a whole community of people out there who, like, love talking about this stuff, even like listening to podcasts like this is a great way to, you know, kind of build that community as well and get that insight. But people are so willing to have a conversation around this and help each other figure it out, which I also really appreciate so like, reach out, ask people who you think are doing amazing things and seem to be getting it right, like dropping the line.

William Harris 1:02:28

We love to sound smart, and more often than not, if you ask somebody, they will love the opportunity to tell you what they think.

Caitlin Choate 1:02:34

Right. Yeah, exactly, exactly,

William Harris 1:02:36

um, how do you keep your team motivated and aligned with the bigger why? Cuz you guys have a big why. But how do you keep them motivated with that? Yeah,

Caitlin Choate 1:02:45

it has to be authentic in what we're trying to do, right? And this get people to fall in love with the Boatsetter way of life being our very authentic North Star, I think, helps quite a lot. We also are a team and an organization filled with people who love being out on the water, like, I'm always the one who's like, Who's calling in from a boat on the next all hands. I've done it nice. I called in from a boat. It was very noisy, but it was fantastic. We've had a few other people do that. So I think it's just like that, ever present reminder that we should be having fun while we're doing this thing, like our social media manager is often out on a boat with other influencers, getting content or building relationships. Our art director often out there working with photographers. Our team is out on the water quite a bit. And I think realizing that, like, Yeah, this is why we're doing what we're doing, and we need to get more people out. And I forgot I was a little bit nervous about this kind of thing, because I had never done it before, and that can help us do our job better, or speak to future partners better. I remember Tiff and I went out in Fort Lauderdale, probably, like a year ago, and she was also shooting some content, and I think got a little, like, seasick, and it's like, oh yeah, now we will have more empathy for the photographers. We reach out to telling them, like, maybe take some Dramamine before you go. So it's like, ultimately, like, living the lifestyle helps us do our job better and reminds us how much we actually love the things. So, you know, I think I've pretty much always worked in in environments. I've been really lucky to work in environments where these companies are filled with people who truly, deeply love the product and use it inside and out. I mean, when I was at Airbnb, it was every day you'd have people coming and going with a suitcase. Where are you headed off to? Where are you coming back from? Who's the host that you just met? Even at Nest, like everybody nerd nerded out on technology and energy and what we could do to grow that community and so. So, yeah, I think it's it's a lot about really loving what you do and hiring a team that truly loves what you do. Again. It's about not telling a team what to do, but inspiring them on what they're capable of achieving. And context, context, context, context, context, because I want everybody on the team to feel like they have what they need to be able to make the right decisions, and that that I trust them as adults to make phenomenal decisions, better decisions than I would make. I'm not running that function, and so the context always helps

William Harris 1:05:23

context. And like you said, that trust to make that decision is huge, because there's so much that you can unlock by allowing the rest of the team to be able to make those decisions. Yeah, let's go off on a little tangent. You hinted at this before, but what is your take on Done is better than perfect?

Caitlin Choate 1:05:39

Oh yeah. I mean, listen, it's just not the way that the world works, you know. And I think this is, this is also a bit of my, you know, my career being born from social media and not from traditional advertising, right? Like, I didn't start my career in a place where you work on a brief for a year, you hire a team of 200 people to go shoot a 32nd commercial, and everything has to be perfect, from the set design to the colors to the lighting. I came from a world where I had an iPhone and myself and you made a thing that became, you know, marketing for the brand, and we had built an audience of over 5 million people for TOMS on that approach alone, that's just kind of figuring out, figuring it out as we went. And so, you know, I think there's, it's almost like, increasingly, it's important to have, it's more important to have that bigger picture, North Star aligned across the team, because that's not going to be delivered in one ad where we created, or one campaign that's going to be delivered through a gazillion different fragments of things that some will live for 30 seconds. Some will live for, you know, 24 hours in an Instagram story. Some will live on a feed, but nobody scrolls down that far. Some will live on our homepage for a moment. And so it's all of these just flashes of what you're ultimately building. And I think it's, I think the benefit of that is it has created more authentic, more human like brands, like, we aren't perfect, and, you know, as long as the brand is consistent and we're trying new things and we're we're evolving, I think that that's a that's a good thing. And so yes, we have two hours of creative review every week where we're looking through every word and every photo and trying to adjust, but at the end of the day, you know, how long is that thing going to actually live? And you know, we're not going to go spend a million dollars shooting the exact right photo. That one that's a little blurry and a little messy is actually much more authentic. And run with that. And so is a constant balance. I

William Harris 1:07:45

think one of the things that's interesting that you brought up this idea of authenticity, of just having a phone and doing the thing right then and there is. It allows you to not overthink things outside of the perspective of the person who's actually been using this, right? So it's like, if you're saying, Hey, I'm actually going to put this camera on a dog and take them through the yacht, that is to a point, that's a perspective of, like, the users who are going to be here, and they're saying, I've got a dog, and I want to see, like, what this perspective is. It's a very good thing where we've seen this go wrong. And you brought up one example, you know, HBO, Max, whatever, and like, some of the rebrands and stuff like that. And stuff like that, a rebrand that didn't do so well was the Jaguar one recently, right? And why? Because it lost the perspective of the consumer, right? It was maybe one of those things where it's like, this is a very fanciful idea, and like, we can praise the creativity that's behind it. Was very creative unseen before, right? But it lost that perspective, and I think that perspective to your point where it's like, if you actually would have taken somebody and said, Here's your phone, just go do something with it. Right now, it becomes hard to get out of that perspective that you should have.

Caitlin Choate 1:08:53

Yeah, yeah, exactly. A friend of mine had written something around that time because they think Portia had had just done, like, a really interesting collaboration at the time, and so much of their brand really leans on the nostalgia and the legacy of that brand, which, if you look at, you know, a major trend in marketing as of late. And this is common when the world feels so chaotic, is nostalgia is really big, right? Like the world feels so uncertain and the future feels so uncertain that we're really eager to just live in the moment a little bit more. Again, why I think outdoor adventure and just being present in nature, being out on the water is is something that people you know are gravitating towards more and more. And so you see brands like vacation, the sunscreen brand that is like so nostalgic. You see nostalgia through, you know, so many, so many different campaigns right now, but with a fresh take, and with a take that's really authentic to social media. And I think that that's where it kind of Porsche just really landed that brand and leveraging their legacy, whereas you had Jaguar, I think tried to do something that was really disruptive and really different. And listen, I there, I think there's often so. Much context that we don't have is outsiders that maybe they debated this all so much internally and landed on that direction is the right one for the brand, which would have been amazing to be a fly on the wall for. I mean, it's hard to do something bold. I applaud anybody who does something. Totally agree, but I think it did leave a lot of people wondering, like, hold on, there's such an amazing history and legacy with this brand, and why not leverage that for where it's headed in the future and allow to build on that emotional connection? It was very similar to HBO. It's like, why drop the HBO? People love the HBO brand. Build on that. So yeah, that was a that was an interesting one to watch.

William Harris 1:10:39

I feel like there's a balance between authenticity and Done is better than perfect with the sometimes there is the need for pixel perfect. And I've seen this where you're either in one camp or the other, and I feel like there should be both, at least on the performance side, there are campaigns that, I will say, Outlook, at a client, and it's, it's all UGC. There's nothing that's been designed on purpose to resonate. And when you look at the performance of UGC compared to, let's say, crappy design stuff, UGC outperforms, but when you look at UGC compared to something that was done very, very well. And some of the examples that I love would be like the Dollar Shave ad, when that one came out right or, or the pooper e1 or like, there's some ads that have just been sensational, ads much more viral than UGC, but they were done on purpose. They were high production and they outperformed. So there is a time when pixel perfect is worth it. When do we need to move do like? Do you agree to it? It sounds like you sue, but like, if you do, like, when is when should we be looking at pixel perfect, and how should that look?

Caitlin Choate 1:11:46

Yeah, it's, it's so much goes back to who the brand is, that brand persona, what you stand for, right? If we were a medical sales device, brand pixel perfect to convey that trust and that care that is taken with every single piece like that is really essential, and that's also where I think some brands maybe confuse the the how you operate in the social environment, like the Duolingo approach, the being unhinged approach, doesn't work for everybody. What is your brand and what have you chosen about your brand persona that truly reflects what you do and what consumers need to know about you and feel about you in order to purchase with you? And so you have to design your approach, your strategy, your brand persona, all of those elements to match with what's the business job that we actually need to execute upon here and what's going to allow us to take advantage of the chat, the tactics and the channels at our disposal to be able to do that? And so don't jump on the trend bandwagon of everybody's being in hin unhinged. Let's go be unhinged like a Cedar Sinai my hospital and La started, like being really unhinged. I'd be like, I don't know if I should go to that hospital anymore, right? But, like, a really fun app that's gamified that, you know, I want to have fun with and learning Spanish with my six year old, like it works for that brand. And so I think, you know, marketers and brand builders need to stay focused on, who are we and why, and what is that going to help consumers know and feel about us, so that they ultimately purchase with us at the end of the day and spend money with us. Money with us and stay, you know, laser focused on that. Yes, understand the environment that you're putting your marketing work out into. But also, you know, it may be that, you know a Tiktok account isn't right for your brand, because that's not the style of marketing you need to be doing, and that's not where the audience is, who's going to be, who's going to be, who's going to ultimately be purchasing you? Yeah, thinking

William Harris 1:13:44

about the audience is important, knowing when it's the right time to do your best, right? Like those are things that we should be aware of. I want to dig into the human behind the strategy here, who is Caitlin Choate. Tell me a little bit about your childhood and how that's helped to shape you.

Caitlin Choate 1:14:03

Oh, man, so much of it, and it's so so different in a lot of ways than things today, but in some ways so similar. Sure, I grew up in Florida, small town on the East Coast and the inner coastal. My dad's a dock builder and a fisherman. And oftentimes, when we go back to Florida to visit, the big activity is we're going to go out in the boat. We're going to pull the crab traps, which is a very messy thing to do, which I think he's kind of pulled my husband into more of the manual labor on that I just get to kind of watch. But we, you know, I spent my entire childhood, you know, out on, you know, his boat that he was restoring at the time, or he once built a houseboat off of an old barge. We got it cut out in a storm once. And I don't think he properly thought about like, how it stayed balanced and the thing almost tipped over. And that was a terrifying, terrifying moment in my childhood. But. You know, I think I just constantly saw my dad, always on the go, always working on a project again. He wasn't the one who was doing it perfectly. You talk about things that translate into like how I think about marketing, or how I even approach my job, it's not about doing something perfect. The houseboat almost flipped over, but it didn't flip over, right? You don't want to hire my dad to, like, build a beautiful piece of wooden furniture. You know, that's, he's not a carpenter, but he's going to build you a really reliable dock and sea wall and boat lift in Florida. And so, you know, that was so formative for me and my childhood, just kind of going around with him to job sites, or being out on the boat with him and and kind of being fearless in that way of like, I want to go do this thing, and I'm going to figure it out, and we're going to do it in the in the all of the weather and unpredictable nature of Florida, which, which was a lot of fun, in a way, to to to kind of grow up. Yeah,

William Harris 1:15:59

sounds like you learned a lot from your dad and you like learning. I understand. You're a student again. What are you studying now? Oh

Caitlin Choate 1:16:06

my gosh. Again. My friends would call me so obnoxious for continuing to talk about this in every place.

William Harris 1:16:14

As long as it's not CrossFit, you're okay. You just can't keep talking about

Caitlin Choate 1:16:18

CrossFit. So can you tell I've been doing CrossFit lately, I've been getting really small and doing burpees. No, I would never tennis. I've picked up tennis. And one of I'm one of the racket sports folks, picked it up towards the end of last summer. And you know, for me, I think the thing that I realized is, like, kind of getting out there three or four times a week, taking a ton of lessons, was that it just really helped me feel like a student again, terrible tennis player to start right, and I was not the expert out there, and I really had to listen to my coach or listen to my friends, and really have to study again. And I just kind of fell in love with not only the sport and being out there and having something fun and unique to do with my friends, but also just this feeling of being a student again. And so it's one of my favorite things. You know, it's if, if I've got a stressful week and we've got a board meeting, or, you know, there's a lot that that we need to get done or a challenging strategy we need to think through, it's, it's fun to be at a place in my career where I can draw on all of that, and I have a lot of answers and advice and context to share with people. It's fantastic, but then to totally switch gears and get out on a tennis court and be like, I have no idea what I'm doing, and I'm purely a student, and I'm starting from the bottom. I think it's it does phenomenal things for your headspace and and for how you approach life. And I think, you know, there should always be something present in your life that you are fully a student for at every stage of life. And so that's been a really, really fun one to pick up.

William Harris 1:17:51

I, you know, you talked about hobbies and how hobbies lead to, you know, lifestyles and stuff. When people say, Well, what's your favorite hobby? My hobby, my the hobby that I enjoy the most is learning. That's what I like doing. I like learning something new, right? Something different. And so to to some degree that's a good thing, to some degree that's a bad thing, because each hobby can get quite expensive, and so he can rack up quite a bit of expense on one hobby. And then you're like, Well, I don't know, I'm not feel like a student on this anymore, and I need to learn something new, but I like that. You're into tennis right now, yeah? But

Caitlin Choate 1:18:22

see, that's where a lot of these, you know, brands like ours, like, there's, there's kind of something for everything, where you can try these things out, yeah, without, you can go to a great, you know, woodworking class without having to refit your entire garage to be a yes, you know, there's kind of like, steps, steps that you can take. It's probably why sourdough took off so often. We get or so quickly, because people have ovens and, sure, a few ingredients. And maybe that's why sourdough really took off

William Harris 1:18:52

little easier than the chickens. There's, you know, what is, I think I saw something about where, like, a meme where it's like, you know, husbands, as soon as you get a chicken coop, just know that, like, sourdough is around the corner, kind of thing, like one led to the other. And we do have chickens. We did try the sourdough. We were not very good at sourdough. We like to cook. We like to bake. We're just we didn't master the sourdough thing. It died a lot. But

Caitlin Choate 1:19:16

so, so what are you learning about now, William, that's got you kind of fully locked in, yeah.

William Harris 1:19:21

I would say the thing that I've the most excited about right now is physics, specifically the physics of light. Yeah, the physics of light. There's so much about light, and I won't go too far down that rabbit hole, but one of the things that I really appreciate about physics just in general, so light and then sound, and I like how they both work into it, but on the light side of things, what we see visibly on the spectrum of light is just a very small little portion of the electromagnetic frequency, right along with the rest of that. The same thing, the same photon is at different speeds, basically, or different wavelengths. It's going to be microwaves. It's going to be infrared wave. Waves. It's going to be UV waves, right? There's all of these different ones that we have. We just don't see them. It's the same thing, though. And what's interesting is we are able to use some of that light to see through our bodies, to see bones as X rays. We're also able to use some of that light to see thoughts now, so with a functional MRI, they're able to show images to people, and then they're able to recreate, based on what they see through the FMRI of their brains, what image they are likely seeing. And it's getting really eerie. So we could see people's thoughts. We can see their bones. And I keep going back to the interesting. So the other thing that I really like is I'm a Christian, and so I really like to read the Bible. And what's interesting is God said, he said, I am light, right? Okay, that's interesting. So if you believe that God created light, and you also believe that he then would know all the properties of light, and he says that he knows you, He knows your thoughts, and you think, Okay, this actually makes scientific sense too. This is a very interesting thing. So I like blending physics with Christianity. Is my thing that I'm the most into right now.

Caitlin Choate 1:21:06

Do you know what? I think maybe this can be counter intuitive for some people, but it kind of goes on a similar path where, like, I've gone down credit like astrophysics and kind of space path. And if you get overwhelmed with where you are in life, or you know you you feel like you have too much on your shoulders. You just don't know quite what to do, like read about space, like it will just remind you how small we really are and how much we do not know. We don't know really anything at all, and we are so small, and we are here for such a short amount of time, and it just really helps you put into perspective everything that we're doing. So

William Harris 1:21:50

totally agree, I and but I do like believing that we are the one and only you are the one and only. Caitlin Choate, so I'm against the many worlds interpretation of quantum mechanics, and so I wrote a very long paper about this, this idea of, like, how it I believe there's just one world, and all of them kind of culminate in this. And it's taken from something that Feynman talks about with light. And so what's interesting is light takes all the possible paths, but it basically like ends up just taking the one path and saying, This is the most efficient path, but it does take all the paths. I believe that history does the same thing that all of the possible things get there, but then they end up being just one, and there's just one. Caitlin Choate, there's just one. William Harris, well, there's actually a lot of William Harris's in the world, but there's just one me, William Harris, and I like to think that there's some significance to who you are and to who I am, and so I should do the best that I can with this life that I have. I should make sure that I take the time for the person who I see who's begging for food. I should give them some money, because this is the one and only of them that I think exists as well,

Caitlin Choate 1:22:46

you know. So I like this. It's, you know, here all of the really tactical ways to grow your business and work closely with data and your CEO to unlock brand and performance marketing, but also live your life. Have a great time. Remember that you're a one of one, and maybe you need, maybe there's a spin off podcast for you there. William, I can, I can hear how, how fired up you get about this topic. I think I do podcast idea there, I do.

William Harris 1:23:14

So I want to ask too, if we were working in an office with you, what would I learn about you that's not obvious on a video call like this.

Caitlin Choate 1:23:22

Well, what's one of the things? It's definitely not obvious because, because, if it's recorded, I have to sit still. I It's funny. It's It's been a while. It's been, like, four or five years since I've worked in an actual office space, but I could never sit still in an office. It's kind of infamous for never actually sitting at my desk, and I think that's because, you know, your work kind of changes so much throughout the day. You kind of need to get heads down on email, and then you need to kind of think creatively through a brief and then you need to kind of like, analyze this data that you got from this research team. And I think switching up your environment really helps you break out of patterns, break out of, you know, way of thinking, just kind of switch things up. And so it was really fortunate, you know, the Airbnb office, the nest office, the Tom's office, were just all phenomenal office spaces that really were designed for, like, a lot of mobility. And so working from home is the most I've ever sat from a desk. And my team knows that, like oftentimes all you know, they get a little bit of the Blair Witch Project, kind of, which I don't a lot of them maybe don't even get the reference, but kind of moving around with me in my house, or going over to this space, or going over to that space. But I You don't necessarily get that from sitting down at a zoom call.

William Harris 1:24:43

Well, I get the reference. I also completely resonate with you. I move around all over the place too. I think my team sees me in a bunch of different locations in the house. It has been so fun getting to know you, talking to you, learning from you, learning about Boatsetter, if people wanted to work with you or. Follow you. What's the best way for them to

Caitlin Choate 1:25:01

do that? Find me on LinkedIn, DM us on Boatsetters Instagram, get out on the water and shoot me a photo of it. Or if you're like, I don't know where to start on Boatsetter. Will you help me find the right boat? These are the things that I love, genuinely. I love digging through our platform for things like that. So hit me up. Just ask,

William Harris 1:25:20

I love it, yeah, just ask. That's a good reminder. Well, again, thank you very much for your time, sharing your knowledge and sharing your wisdom with us here today. Thanks for having me. Thank you everyone for listening. Enjoy the rest of your day.

Outro 1:25:32

Thanks for listening to the Up Arrow Podcast with William Harris. We'll see you again next time, and be sure to click Subscribe to get future episodes.

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