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The Art of Being Tastefully Unhinged | Sr Director of Brand Marketing @Duolingo, Kat Chan

1h 19m

The Art of Being Tastefully Unhinged | Sr Director of Brand Marketing @Duolingo, Kat Chan

Cat Chan’s dynamic career journey—from social media at Live Nation and Red Bull to high-stakes roles at Tesla and Facebook—reveals a deep commitment to creative freedom and authenticity in marketing. Central to her philosophy is the belief that good taste isn’t about judgment, but curiosity—the willingness to explore the “why” behind any creative work. At Duolingo, she built a culture where trust, speed, and playfulness are prioritized, allowing teams to operate at “internet speed” with minimal bureaucracy. This environment fosters creativity by removing fear of failure and enabling experimentation, even with controversial humor or edgy content like violent or absurd social posts. Cat emphasizes that such risks only work when rooted in a clear brand mission: making learning fun. Her experience shows that corporate environments often stifle individuality, leading her to value workplaces where self-expression and emotional safety are central. She believes taste develops through exposure to diverse cultural forms—such as fan fiction, AI art, or global fandoms—and that creativity thrives when teams are encouraged to question, debate, and innovate. Ultimately, Cat Chan champions a philosophy where success isn’t measured by perfection or compliance, but by resilience, curiosity, and the courage to take bold, human-centered risks.

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Everyone says they want a marketing strategy like duelingos but how many people are actually willing to threaten violence on their users. You wear the L mask on handler which means you're just mama duo, right? Yes. Would you rather hire someone with high taste but poor execution skills or high execution skills and poor taste? Ooh, high taste and poor execution skills. What does it mean exactly for someone to have good taste? Ooh, okay. The team that cooks are very creative and creativity does not flow in a fear-based environment. It flows in a trust-based environment. There's a bunch of videos of duo and body suits. Were you ever in one of them? Multiple times. It's so sweaty. It is honestly one of the hardest jobs on the team. Where is AI actually useful in creativity? AI is like a big flattening of everything's just trying to predict the next word in a sequence. So it naturally takes an average. Exactly. And good ideas are all about being not in the average. It was one lesson you learned working with friends. This is the way you can communicate in a friendship and sit in the ambiguity is actually not something that carries over to business. Business needs to be extremely clear about expectations. You worked directly with Elon and saw it. I did. What was it like being in such close proximity to perhaps the most powerful people in tech? Ooh. Damn. Welcome to office drama where we define the modern career for Gen Z and millennials today. In the office, we have the brains and the leader behind the most tasteively unhinged tech mascot on the planet. Welcome Cat. Cat. Cat. Yeah. Yeah. Oh my god. I'm so excited to have you here. Y'all, you don't know what a privilege it is to have this woman here. Cat Chan is the senior director of band marketing and Zoolingo. On her LinkedIn, you were the Elle mascot handler, which means you're just Mama duo, right? Yeah. You burst duo from your womb. Definitely. Five years ago. Literally every Gen Z and millennial knows about Duelingo and duo's crazy antics on the interwebs, iconic. I got the privilege to stalk you on the internet and your background is so impressive. You have so much lore. I was like, in a way, we're going to fit this in our interview. But I want you to go through your career journey. Can you just describe every company you worked out with one word or phrase, and I'm just going to go in order? Okay. Yeah. Starting with social media manager at Live Nation and Ticketmaster, one word girl, one word. I mean, you have to be hype. It was such a time where I was like so wide eyed and every meeting was exciting and like, you know, I got to sit in the same room as Shakira ones. Like all I wanted was to work in the entertainment industry. Shakira. Shakira. Shakira. Okay. Wide eyed. Very. I'm going to add Red Bull, like sorority or like frat. Really? Yes. Because Red Bull is based in Salzburg, Austria, it's not even based in Salzburg, Austria. It's based in a tiny town outside of Salzburg, Austria called Fushal Amze. It has 1,500 people that live there. And the people who work at Red Bull, a bunch of them are just like expats who move there for the job. And so you feel like you've joined this extreme sports press. It's really fun. Do you do sports? I do, but not when I work at Red Bull, I just go get it later in life. Okay. Have a marketing and e-commerce at Tesla. The trenches. It was like war. Honestly. It was the best of times it was the worst of times. Executive comms director for Mark Zuckerberg at Facebook, clinical, clinical, not war. And now do his mama at do a lingo. Fun. I mean, it's the most fun drama I've ever had. No question. Oh. I'm so cool. Like fun. Because you've been there for five years now. It feels like fun. Yeah. I think you were someone with great opinions and great taste. And when I try to stalk you, you do not have a digital footprint at all. You know how hard it was to come up with interviews. I was like, can't use AI, can't use my brain. I got to like read between the lines, but I am so grateful. You said yes to coming on office drama. But what made you say yes to your girl, Chloe? Or did they force you? They did not force me. I think because you seem like someone who is really willing to explore all the different parts of themselves publicly. And I think that's pretty damn cool. Oh, really? Yeah. You know my digital footprint. Yeah, exactly. We're opposites in many ways. But I like your content. Your last interview was like five or seven years ago. Yeah. So now you're ready to share your lore online. Are you ready? I'm ready to have a conversation with you. We are so lucky drama llamas. We're getting the exclusive comeback of Cat Chan. You do not get access to this level of leadership. I had to use all the cloud and power in myself to drag this person out and come to L.A. She's not even based here. I don't know flight. To be here. That's right. I was like, I don't know if I could do this. I'm a die. But anyways, to introduce yourself to our drama llamas, can you look into their eyes and tell them your MBTI astrology sign and where you grew up? Hi, drama llamas. I am an ENTJ, though very close on the E and I. My astrology sign is cancer, but I feel a little like a Gemini. I'm like kind of on the cuss and I grew up in L.A. actually in Pasadena. Pasadena. Yeah. Are you 66 or 9? I am 66. 66? Yeah. Wait, where? Passing to Heights. Oh, nice. You are also a proud mama. I am. Of a 20 month old? Yes. Yeah. Her name is Colette. Colette. Did you watch Les Mizz? Yes. I did watch Les Mizz. There's a movie called Colette with Kira Knightly in it. Like she was an French author whose husband like to credit for a bunch of her work. Of course. Like course. Through off the chains of the patriarchy. Yeah. And so I paid you the same for her. Exactly. And she's named ad age leading woman in 2024. What does that mean? You know, I'm not sure. But that's impressive. I think it means that I was connected to a really great group of women who are all super ambitious and trying to carve out leadership in their field in marketing. Yeah. Your career is so fascinating and long because you started off at Ticketmaster and Live Nation in 2010 in social media before social media was a thing. Like Instagram only started in 2010. And that's not social media. It was just pictures, right? Like a photo of the beach with a filter on. So like. What was social media at the time? Social media time was like Farmville on Facebook canvas apps. Twitter was still a thing. Twitter was a thing. It was a key. It was a thing. It was like watch the throw and like Jay-Z and Kanye that era. That was like the most exciting tour I worked on. But yeah, I mean, the job was like, it was fun because basically social media was the term that people used to like label anything randomly digital. And so you got to do a bunch of things, including like making content posting, though it was really basic back then. But also like, we built this app that would connect your Facebook likes to the Ticketmaster events API and would basically fill your concert calendar. The coolest thing about it actually was just like the secret weapon is that we had a Facebook event auto created for every concert. And so it ended up creating like a ton of organic traction because suddenly we flooded the Facebook event ecosystem with like Kanye West concert at like, it's like game that system. It was awesome. It was like, yeah, it was the like gray matter of marketing back then. You studied composition in college music, yeah, oh music, yeah, and then you became it went in social media. But I guess like nation is like music. Yeah. I think I like sort of realized that I wasn't good enough a musician, like I just hadn't trained for that long to do it professionally without like a ton of risk and immigrant mentality. I was like, no, I got to do something more secure. So I was like, okay, I'll work in the industry. Did your parents understand what you were doing? No, definitely not. They knew that I worked at a company that they had heard of. Yeah. Okay, so they're like, I think she's fine. Yeah. But during that time, my mom would call me a lot and be like, what about law school? Are you still in law school? Oh my god. Yes, siblings. No. Okay. So they were like all eggs in your basket. All eggs in my basket. They were up in your business. Yeah. They were like, you cannot fail. Yeah. My daughter. Yeah. My daughter. Huge disappointment that I wanted to entertain. Or diving now. They're okay with it. Then you joined Red Bull as a VP global head of audience development. What is the most explain it like in five way? What does that mean? What does that mean? Big titles. Like, what? I grew into that title. It's like not how I started, but it just means that you are figuring out all the different ways that the Red Bull content gets on different channels. Okay. So it's like a bunch of social, but also email and web and all that kind of stuff. This was 26, 10, 17-ish, and you're working with influencers. And that was also the Wild Wild West of influencer era. That was the Wild West of influencer era. Like anything went. Like no contracts. We collaborated with Shanduras, who is now a huge parent influencer, when he was a Snapchat influencer. Oh my God. This was like OG, Zach King Days. Oh my God. Yeah. Whoa. And did you work with gaming streamers? Because I feel like I associate Red Bull with gaming streamers a lot. We did. That was a sports team. It was like a different team. Okay. But we did, even back then, before I even left, we had a contract with Ninja. We did a lot of games. That's it. It's a big contract. We were doing professional esports, like we were treating them like athletes, right, versus content creators. So you were working with esports teams? Yeah. We also got a phase clan for a while, a phase clan after my time. Have you gone to phase house? No. I've not gone to phase house. I was living in Salzburg, like, where people still deliver beer by horse. So I think in 2017, I joined a live streaming company, and then we also worked with streamers and gamers. Yeah. Not going to lie. We had a lot of people to work with because they were not responsible human beings. I'm so sorry. I believe that. It was fascinating. But getting people to, like, be on time or respond back was atrocious. Then you hard pivoted from CPG to Tesla and Facebook. Yeah. You know, tech is a whole other ballpark. - You worked directly with Elon? - I did. - Anzal. - I did. - What was it like being in such close proximity to perhaps the most powerful people in tech? Like, that's wild. - They're very different. So the two experiences were very different, I would say. - Tesla was tough for me. - I joined because at Red Bull, I felt like, okay, we had built, grown this team from like, I was the second social media hire into like a 50 person plus org. And it started to feel like we were kind of making a sort of factory for content creation, right? And like, it didn't feel as zero to water like creative anymore. And Tesla came to me and was like, oh, I think we're looking for someone to do social. Elon cares a lot about social. Would you be willing to consider this? And so I was like, hell yeah, because I had just read the Elon biography. I admired him a ton. Like, I was like, I have to work for this guy. - Yeah, there was a time, and he was cool. - There was a time, and I went. I mean, I learned it like more probably than in any other job, even though I was only there for 18 months. The thing that was really hard for me was that, at the time, you know, he was very cool. Like, people adored him, thought he was changing and saving the world. And in some ways, I think it's still true that he's like the most impactful person in the world, but I did not enjoy working for him. The joke that we used to have was like, Elon is good for humanity, but bad with humans. (laughs) - Whoa. - And I would've lied. And I think like, experiencing his style of management, which like truly is not for everyone, even though I respect what he's done, I was like, okay, I can't do this. And a lot of the more extreme personality things that you see now on Twitter or X, I guess. I saw in person, I felt like there was such a dissonance between the reality of the job and what everyone was thinking. And it was like hard for me to live in that. And so I was like, okay, I think I need to gracefully exit. - Valid, yeah. - Wow. - Thank you mentioned in Posters Syndrome. Did that happen during this era of life or no? - Yeah, but I mean, both a Tesla and Facebook job, you're surrounded by so many super type A ambitious, intense people who only prioritize their jobs. And the expectation is that you are on call 24/7. I like, briefly was a project manager for Elon in the office of the CEO. And to interview for that job, I waited in the factory until like 11 p.m. when he had a free 15 minutes. - It's just like, you know, it's stuff like that that I think at the time was good because it was a really good learning experience for me. Like it taught me to get shit done, for sure. - Yeah. - It taught me to problem solve, but in retrospect, it doesn't feel sustainable, especially the 20 month old. - It's getting Hollywood agent assistant, like. - Yeah. - It's in my laundry. - That's a good enough. - I know my password. Like, why do I know your password, like the hell? - If you go back in time, what would you tell in Posters Syndrome Cat? - I would tell her not to be afraid to trust her own judgment over others. I was like so trapped in the idea of what success should be in a corporate environment. The reasons I took the jobs at Facebook and at Tesla was because of what they represented, right? Like I would get to work with the smartest, most powerful people in the world, but I had to recognize that like, that's probably not what makes me happy. - Yeah. - And I had to prioritize them. Over time, you do change the way you showed up at work. I would imagine if I were to enter that environment, I'm like buttoned up, I'm like muted. I'm like, I'm not saying anything crazy. I'm like, at Facebook and Tesla, no, I had to be buttoned up to a degree. Like that's not to say I didn't meet some really awesome people who are still like some of my best friends today. Like especially at Tesla where the work was so intense and so demanding, you feel like you have trauma bond buddies basically? - I'm sure you really. - I know. I do. - I'm healthy, but I do. But I think in my like at Duelingo, I do feel like I can very much be myself. - I love that. - Yeah, I think also doing a much more open to being like, you know what, I'm actually just not gonna be good at this or like understand that you can be flawed and still be successful. - I think that when I was like between early 20s to 25, I was really chirpy person and I still am, but wait, or maybe I'm going back to it. - Chirpy was nice. - Yeah. I'm like, well before I was just nice, I was really happy. Like I'm just a happy girl and I was very coca-ish. Like I don't know that I'm smiling at you, but my face is just like smiling. And then I remember I had a coworker tell me, like pulled me to this side, pulled me for a chat. He told me, gave me unsolicited feedback and he was like, you are too bubbly to be a leader. No one takes you seriously and you just can't act like that. And I was like, okay, but that's fucked up. And then I cried in the phone booth and then from then on, I like stopped and muted myself. I was like, no personality, no character, no vibes, no smiles, just, ooh. TJ and the heck out of myself and that was really suppressed because I think sometimes corporate makes you a certain way. And then over time, I had to bring that back out. I was like, I hate this. I hate being contained. - I'm not a fan of that guy. - I know, he sucks. - Is it inappropriate feedback to give someone in a workplace? - Also he had a freaking crush on me, the hell. - Can you believe that? - Classic. - I can absolutely believe that. - Classic. - That's the same as like pulling your paytails on the playground basically. - Yeah. I was just so freaking upset at that time. I wanted to ask if there was like a really low time in your career where you were really hitting a wall or the bamboo ceiling and then someone said something to you that completely changed your brain chemistry and got you out of that. - Definitely my low I think was doing this Tesla project management job. - The trenches in the trenches. It was a job to scale up model three deliveries at a time when like they didn't have a strong delivery system. Like basically they had more deliveries to make than they had like spots in the parking lots of the dealerships. And so they created this program called Tesla Direct which was like we were volunteering employees to drive Teslas to owners homes to deliver them and it involved a ton of different groups from like delivery to retail to the energy team and coordinating all of this. The reason it was a low for me was because I felt constantly like I had no idea what I was doing and yet I was being swept up in like the current of the work and in the moment I didn't get this perspective but then someone who was like a trusted leader on the, actually I'm like the digital side of things. I was like telling him how I was like, I feel like I have no idea what I'm doing. Like I'm even doing a good job. Like Elon has pissed about this every single day and he turns me in was like cat like no one has any clue what they're doing. No one has ever done the thing that we're doing before and so just the fact that you're putting one foot in front of the other means that you are succeeding and that really helped me in a very, very low moment and I've had a couple leaders like Sarah. - Sarah? - Yeah, shout out Sarah. - Yeah. - She once told me like you know what every morning I look at myself in the mirror and I'm just like okay I gotta fake it through the day and like that is actually how you learn. Like that's how you beat the imposter syndrome to just like embrace it and lean into it. - So you believe in the fake it till you make it mantra? - I kind of do yeah. Well this is similar to like loving the pain of a steep learning curve, right? Like this was a moment where I was in way over my head. I took on a job that I actually like just I think was not well equipped for but with the guidance and help of like a ton of great leaders. I managed to get through it and I came through the other side equipped for it. - Awesome. - It irks me when people are like well I've never done this before. I'm just like girl well none of us have ever done this before we just gonna figure it out. Like we're at the forefront of everything we do. Do you wanna be great or not? - Exactly. - Yeah there's no playbook for any of us. We gotta learn there is no solutions manual. We must graduate. - No. - I think that's a really good lesson. Before you joined do a lingo, I believe you took a two year break is that right? - I took like almost like a one year break. - One year break? - Yeah, two years ago when you were a break. - Was that an existential crisis or are you exploring the world? - It was sort of an existential crisis. - I was just a burnout. Like it was like two very intense jobs that ended up being four years of I think of my career and was like okay I just need to like do nothing for a while. I did some consulting. I did the start of thing that didn't work out with my friend and more importantly like we got a dog. It was sort of like late post pandemic and so lots of comforting things like cooking every day and like finding a new house. And I just feel like I just like got all my brain in order for a longer term build. - And I found the dolingo job, which like I knew I wanted to find something that I felt like could fit for the long term. - When you were in that year, the start of sounds like a big piece of it 'cause you said it was a year and then you only took a year off. - So you weren't really taking time off? - I just tried a couple of months. - Okay, a couple of months. - Yeah. - Yeah. - Well was one lesson you learned about working with friends or are you just anti-friends forever? - I'm, well one lesson I learned I think was like because we were friends, I think we assumed that we knew what the other person wanted in a professional context. And that just proved to be incorrect. Like I think the like assumption of the way you can communicate in a friendship and like sit in the ambiguity is like actually not something that carries over to business. Like a business who should be extremely clear about expectations, you need to be like extremely clear about what is the scope, what does good look like and in friendship like none of that applies. And so I took the mentality of like friendship into this job and I think neither side like communicated clearly. And so that's probably the biggest learning. Talk your shit out. - I learned that too after corporate, going into creator space. A lot of friends wanna work together. And you also don't have contacts on their work lives. Like you love them socially, but from as a business partner you're like, oh, I don't think we're like on the same page about things. And then that's a really hard thing to bring up. - Exactly. - Like I would not say it out loud. I'd be like, I don't know what maybe you would do. I don't know if we can work together. I'm so sorry. - So that's a tough one. - Eduling will be often say like you should be candid and kind and I think in friendship you wanna be kind. but in work you should be more candid. - I agree. So you joined duo, Lingo. How did that decision come about? Did they find you? Were you exploring other alternatives? Was it an absolute yes for you? Did you fall in love with Luis? (laughs) - Luis is awesome, definitely. So I knew that Duelingo was a good place to work because actually like my cousin had worked there. She was Luis's student. And when he was a computer science professor at Carnegie Mellon. - Ooh. - And she had told me about what a great place it was to work. And there was a posting for a social media role. And I was like, okay, you know what? Like, let me get back to my roots and I'll do this again. Like I had not done social media in a while when that role came up. But I felt like Duelingo was a company where I could see myself for a long time. And so I was like, let's go for it. I definitely was intentional about trying to find a place where the culture was strong, the mission was strong. And that I would just like kind of feel good showing up at work every day. Something that I know about myself is like, I tend to adapt the systems that I'm in or like the values that I'm in. And so I could see like when I was working at Tesla or Facebook, like I could see myself being this very like, type a hustle sort of like ambition at all costs kind of personality and I like didn't want that for myself, right? And so in Duelingo, like I feel like yes, great work matters, but so does kindness and thoughtfulness and fun. And that's what makes the products a brilliant actually. It's like that the product is fun because learning should be fun. - I love learning. - Yeah. And I knew that in the interview process, like they treated the candidates with such care. Like they gave you like a little care package. Like they were really great about answering any questions that I do was going to be a good place to work. - That's awesome. You were an SF at the time, right? I heard from the great mind that Louise hates San Francisco and is like one of the company's core values to never have an office there. So why do SF hate? And does that mean you might move to New Yorker Pittsburgh? - Ooh, spicy. Okay, because it is like a topic in our family. - Yeah, that's a topic. 'Cause I know one of my friends who was a Twitch like product director moved to the East Coast and has to fly in New York and Pittsburgh a lot. - Yeah. - Matt Long on the team. - Yeah, I do fly to the East Coast like almost once a month. And usually go for a week. I don't think Louise hates SF, but I feel like Louise is a little bit the anti-tech bro, tech founder. - Yes, I heard he's so sweet. Like I wanted to interview him, but I couldn't make it out to the East Coast. And one day. - I know, but I think the high reviews, high ratings for Louise. - Yeah. - Public enemy, you one day, bro. - Louise, if you're listening, I hope you open an SF office one day. - Oh. - So you want to stay in SF. - I do want to stay in SF. We have talked, Alex is my husband. - Yeah. - We've talked about moving. Like I don't think it's out of the question because I do, like all things being equal, I would love to have an office to go to. I want to be an office. - Yeah. - It's so real. - It's so real. - But also, I feel like everyone has a side hustle now. But we just bought this auto repair shop. It's like a small business that Alex is going to run. - For like cars? - For cars. - Oh yeah. - Have you heard about this? There's a thing happening right now where there's a bunch of small business owners who are retiring and like, - Yeah. - Like buy boring businesses. - Yeah, yeah. - Yeah. - One of the buy boring businesses can do in it. - I think that's great. - For those houses. - That's great. That's amazing. So you joined Duolingo in 2022 as director. And I think this was after Duolingo hit like 5 million followers on TikTok, right? - Before, I think. - Okay. - Yeah. - But it was definitely growing. - It was on that time. - It was growing, yeah. - It's a part of the reason I joined. Like they had seen early success on TikTok because one of our like, Gen Z employees. - Yeah, sorry. - Yeah. - Yeah. - Put a TikTok video together. Like really believes in the platform and it went crazy. And I think a lot of the people in the marketing team were sort of like, "We're not sure what to do with this." And so they just like wanted to bring someone in who had worked in social before. - What was the size of the company and team at the time? What were you exactly like hired to do in that first year? - Yeah. I think at the time, Duolingo was like 500 people. And then the first year when I was hired to do was to build and scale a social strategy that would help kind of replicate the success that they had built on TikTok across other markets and other platforms as well. - Got it. And I think that you weren't an IC. You're dumb at those days. You weren't executing editing, doing text overlay's copy. I think you mentioned that you had to really like build the right guardrails and core principles for the team to be able to operate on. So what were those core principles that Duolingo had as a brand, do you remember? - A couple. I think one was like our core platform, like the creative platform that we were ideating off of was learning as hard so we made it fun. - Yeah. - And so that sort of is the reason why Duol does what he does, like he can get away with a lot because his mission is to get you to learn. Like he's trying to get your attention for a good cause, right? And so I think like that was one of the core principles of everything that we did creatively. A couple others in terms of like how we operated. Like I really believe that you should take the shortest path from idea to post, especially as a brand where you're trying to move at the speed of culture. I need to buzz the corporate speak thing right now. But like basically if you wanna react in social, you have to be fast and so like hiring people who are multi-hyphenets, like they can do a lot of different things are comfortable, like concepting, editing, shipping, like copywriting, I think is really important. And then so we developed these like really detailed do's and don'ts for sketchy topics, like substances or violence or sexuality, like what isn't, isn't appropriate. But we think of the guardrails as like a floor and not a ceiling because you want to enable creativity. And so as long as you hit like a certain bar of quality that you should define, then you should allow the team to experiment, right? So it's like, it depends on the campaign. But like for social, I think like I try not to be too precious about creative because what is most important in social is like the ability to experiment, the ability to move fast and an understanding of culture, right? - Yeah. I remember this also, Dueling goes to comedy. - Yeah, Dueling goes to comedy. - The brand is in on the joke. We don't take ourselves too seriously. Duel is an influencer. - Yeah, not a corporate account. - Yeah. - It can participate in creator culture and parody them. - Yeah. - And Duel's behavior is justified by the obsessive desire to make users complete lessons. - Yes. - So as long as we always hit that hard string, the main point, the account is a sitcom. - Yeah. That's right. - And that's mystery for adults. That was also another one. - That's funny. And then the only rule that we have is there are no rules. That was one that you said in that interview, like seven years ago, whatever, or five years ago. - I would bring these down. - I was like, I don't know if these still hold true, but I'm going to write this down too. - Do you think that what you all did with Duo and the social accounts and like using social media and culture as a gross mechanism? Is that what any company can do? Or is it something special about Dueling go and do his image? - I think that anyone can use culture as a gross mechanism. But I don't think that that looks the same for everyone. I like to think that we were a part of starting the mask culture. I'm like, everyone has a mask on out, right? Like literally grocery stores have a mask on. And I think the reason it worked for Dueling go is because actually even before the TikTok fame, like Duo was a character in the app for 10 years. Like there was a credibility and like a fandom there already. Like the reason Duo was so unhinges is because we were sending these notifications to get people to do their lessons. And the community is the one that created this meme of like, oh, Duo is going to come get you and we just leaned into it. And so that's why it worked for us. Like we were reacting to the culture and not trying to create our own thing. Whereas now I feel like people see the recipe as like mascot plus unhinge. But there's no foundation for the actual product or like the use case that backs that up. So it falls flat. - Yeah. - Yeah. - Like Duo is fun and you lean into that fun. But how much are y'all willing to lean into negative incentives? Like, you know what I mean? You mean like, will I actually kidnap a learner? - Yeah, yeah. - Violence. - Violence. - Duo is a little violent. - He's a little violent. - In little violent. - Little dark energy. - A tweet that went viral that I'm sorry. I do not remember who tweeted it. But it was brilliant. She was like, you know, everyone says they want a marketing strategy like duolingos but how many people are actually willing to threaten violence on their users. - Yeah. - Right? Yeah, if you want to do it, like you have to be willing to take the risk and I don't think a lot of brands are. - No. - Hopefully. - They quilt it clean. - Hopefully there have been no mascot owl arrests anywhere. And that most people see it as a joke. - But I do think there is a line and that whole strategy is like, try to walk close to the line, right? Like, that's what social is. - Yeah. - My friend, Andrea Kalsanova, I think she interviewed the CMO of duolingo at Cannes because it's a little video yesterday or something. And I watched it because I got to put my girlfriend, Andrea. And she asked him if you would green light a pitch where if you don't finish your lesson, you'll send you a picture of your ex. - Would you approve? - Maybe. - Emotional violence for the sake of learning. - It depends on like how do we get that info and like what form that photo tape? Oh, then hell yeah. If you're signing up for it, you'll be okay. - This is what you're opting in for and this is what's gonna help you on your learning journey, why not? - And then it was like, you're gonna go back to this? - You are evidence that there's no greater motivator than rage, right? So. - I don't know bad, but violence for good, violence for good. - That's for good. - Yeah, there's a bunch of videos of duo and body suits and stuff. - Yeah. - Were you ever in one of them? - Oh, definitely. I was definitely in the mascot suit multiple times. - How is it like, is it hot in there? - Oh yeah, it's so, it's so sweaty. You have very limited motion. You're like often wearing a USB fan. We were at the Barbie premiere and dressed up as Barbie and the guy that was in this I honestly think he almost passed out from the heat because the wig, the Barbie wig was like 20 pounds or something like that Like he was a bodybuilder basically. No serious respect to anyone who has been in the suit. It's a hard job. Oh my god Do you wash that suit cuz that's like you can't Okay, that's a really good question and we have had the suit professionally clean But honestly not as often as we would like let's say where is the suits stored? Did you just have some in local spots around cities that you guys have pop ups at? No, you know, we have a little home for the duo and he like lives in his little bed. No, I'm kidding I'm fly duo. Yeah, we do we do fly up. We work with a company that packages like art and stuff like that And so like they take care of duo really really well. He has like really premium journey Yeah, he's do a fly spurs only the best only the best for duo. Yeah, does duo take a seat on the plane? Or is it is he in the he flies triner? Are you kidding me? He knows he was private. Okay But in all reality, it's like different offices have different Duos I would say and no we don't we don't have them in like every city They're mostly where we have offices. Duolingo takes a very culture first approach and you said culture is the new marketing funnel What does that mean? What that basically means is like now there's so many things fighting for people's attention Like you are literally trying to put a brand message against like a gamer like speedrunning Tetris or Pokemon or Literally love island recaps and so in order to actually like have that attention be Genuine and build an emotional connection like you have to think about what are the ways that you Make yourself relevant in the conversation that's already happening. Yeah, because most brands like unless you're some huge IP With a big story or like a narrative You're not going to be interesting enough to break through and so the way to be successful is to think about how your Brand or company or you as an individual like have something you need to say in a conversation that's already happening You want to be like a great party guest, right? Like you don't want to be like the awkward person in the corner You don't want to be the frack guy that like brings out the guitar at 2 a.m. in the morning to play Under a wall when nobody wants to hear it. This sounds like a personal experience It sounds like there's a person and we hate that person. I mean In certain contexts. Is this like Matt or something? Yeah, or like Bruce maybe I like a Ryan. Yeah I interpret a duel in goes. I guess like how do you break the cultural zeitgeist is Tactically it's entering fandoms and dolingo has a plethora of fandoms that he's entered K dramas with Squid games webtoon Crunchyroll Hike you what I saw that I was like that hit me. I was like oh, yes back matter It was such a deep cut. I was like you know too much K-pop colas with like stray kids and new jeans and I heard y'all are gonna walk duo at New York Fashion Week trying to We're gonna hack near fashion week. Yes hot. I think that the partnerships in the colas with dolingos amazing Again, you mentioned yet the operator at internet speed but partnerships and getting IP rights is hard So like how do you do that so fast? It wasn't easy. Yes. Is there a way you guys pitched it like what okay? It totally depends on the project like for example I think you talked about this video like that took like two or three years of like just warm chats with Netflix like shout out our Business development team at at dolingo like they kept the relationship warm and like eventually when the right opportunity came along We were able to bring something to life, but it took so long to build that up to a place where it could work out And then there's some where we're just sort of like try to hack the moment, right like barbie actually barbie contacted us because There's a mention of the app in the movie like the husband of America Ferreira Uses do a link go for a minute and we gave them the rights to you They like reached out to us and posted like you like can you use it? We're like yeah, and then Warner Brothers was like let's do something and we were like hell yeah And so we brought him to the you know, that's perfect. Yeah, we brought him to the red carpet He had a getty images like image was awesome. It was like duo's hype moment But then there are others where it's like stray kids reached actually they reached out to us and they were gonna be in New York And we're like can you want to film with duo for 15 minutes, you know, and so we were just like okay We need to like ideate and just get it like go. Yeah, so it really it totally depends on the partnership Wow, I mean it's awesome that people are reaching out to you But it is really hard to create collaborations like that it takes years Yeah, it's giving like I went to can lines and party with your executive for a two-year straight And then I have them on your I know I can text and be like hey, man, it's all this wouldn't it be so cool? It's crazy idea. What do they so cool if we work together and they're like oh, maybe yeah, yeah, that's what it's giving You know sometimes we'll do things as fans and not necessarily have like an official Partnership and then the artist is like might be totally fine with it or even like comment positively But then like you know the label or it can get kind of complicated You have to kind of use their brand image, but generically. Yeah, exactly. I did like remove it and then it's not McDonald's McDonald or whatever it's like, yeah, you know, you can't use it completely. Yeah, yeah, yeah today on duo lingos team How big is the company and your org and what is your team structure like today? I think the company is about a thousand employees My org is around like 12 or 15 people and the structure is Campaigns content, which includes like social blog, etc influencers and community. So that's like the core of yeah What we deliver and I think like thematically we're all about just focusing on driving like the perceptions of dual And go that we believe to be true are people mostly from corporate or creative backgrounds? Ooh a mix of both we have a bunch of like super talented young creatives like a lot of people who's just like their first Drive out of college like we really believe in developing young talent I know it's like a tough market out there right now, but it's something that you'll link a really invest in and then yeah I would say we have both sort of like business backgrounds and then what you would consider more like traditional creative director ACD backgrounds for those fresh blood out there. How do you assess when someone is worth taking the risk? Because it's not an easy role nor do I think it's an entry level role I actually think that interviews are like a really hard way to tell Yeah, someone is good like someone is like worth investing and you can really only tell by working with them directly We have like ideators on the team We like to do sort of like trial runs just to see if it's a good mutual fit and like have them kind of get to know the context of How we operate and see if they're comfortable with it and also have us be like, okay Do we feel like it's a good brand fit because the creative stuff is like ultimately subjective and you can't evaluate it through like I don't know like a strategic case study or something right? Yeah, exactly Like it's not so you have to kind of like is there chemistry with the team? There's like so much of the it factor. Well, so you got to do a trial first. We try yeah a few months or something Yeah, and like okay, it's not a bit of it. Yeah, it really depends on the role But for example for something like an ideator it would be like a trial. Yeah. What is your success rate? I think pretty high like we try to look at a portfolio ahead of time or like give a basic case of like what are some ideas that you have? So we at least have a sense of it because we don't want to bring someone on and invest in them Like even for a couple of months right that takes time. So we tried it that ahead of time So what does a portfolio look like for an ideator often? It looks like social content pieces Also their own or other ones that they worked with exactly Yeah, but they can also pitch ideas like if they don't have a presence of their own or like have it work for a brand yet Like what are ideas that you think makes sense for Duolingo? Let's talk about the building at internet speed part because I think speed is Duolingo's mo And it's first of all it's really hard to rally a creative incorporate team to make decisions that fast Sure. I guess what we're organizational decisions that you made so that you can get your team to operate at internet speed Definitely one is that we do not have a classical approval process the way most brands do like I am not approving our day-to-day content The goal for us is like if you're on social and you are creating day-to-day content that at like at when you start You would probably be partner with someone who you're developing like creative with and who is approving stuff And if we're going through like a strategy shift or something we'll do that, but in the long run the hope is that you're actually able to ideate and ship stuff Pretty independently. I think that's really important like you have to let the team cook not to say it again But it is like the core thing who blocks you the most is illegal. Oh No, dude. We have the best no joke the best legal team. I have ever worked with our general counsel. His name is Steve legal legal Steve DC Steve he has a TikTok account and like is a character in our socials Yeah, he's the best he's the last we love Steve. Yeah. Yeah, no incredible legal team. Who is our biggest enemy? They're the mind of the bus On the record. You know what? Okay, there are often brands that really come to us and are like oh my god Like we love what Dueling Go does you guys are so great at social like let's do a collab And you know you guys do whatever you want and then we come up with ideas and they're like oh, whoa That's too much like we can't do that and then hands all you And that happens all the time like really yeah so many brands are like oh well But this doesn't get through you know our usp like our unique selling point or like RTP like reason to buy like they want the I don't know the like positive sentiment or like fame that comes with our social strategy But I'm willing to show the character exactly. They're like not willing to take the risk. Yeah, I'm so annoyed because like they knew what they were Exactly, it's like classically. You can't have your cake and eat it to type of deal exactly. That is our greatest enemy Wow, that's hilarious. Are you ever a bottleneck and how do you how did you try to overcome like thick it in the five years that you were there. Ooh, yeah. Like, it flows in a trust-based environment. And as in any corporate job, there are ups and downs in terms of pressures of like, "Oh, do we meet our numbers this month?" They're, you know, and I think like, I always have to remind myself that in order for the team to actually deliver the business impact that we want to, I have to like, not care about the business impact. Like, I have to make sure that they are not caring about the business impact because what they need is like a high trust environment to be creative. - Wow. - Yeah. - So high trust environment to foster that. - Yeah. - You basically just don't tell them any of the consequences and none of the numbers. - I've never done that, I just don't find. - Exactly. - I mean, they know what they are. And like, I will also, I'm sure if my team is listening to this, they'll be like, "Dude, Kat, like, "you do tell us what the numbers are." - That's funny. - It's just important that when they're like, I don't know, shipping their OKR or something like that or like writing what their goals are, like that we're not just focused on the quant, like we have to be focused on the creativity as well. - When you have a high trust environment and you have a principles of like, our rule is that there are no rules and just let them cook. You're bound to have people make mistakes. - Yeah. - So how do you foster an environment where mistakes can be made, but we still have to learn from them and you still have to take accountability. - A couple of things. Like, one, I like to say that like often, what happens in social is like, if something doesn't go well, usually it just means that nobody sees it, right? It flops. Sometimes very rarely it's like, goes viral for the wrong reason. But we sort of like aligned even with the sea level that like, sometimes our strategy does create that and that, and if like, those risks and if it happens, like, our rule is actually, we need to protect the team, assuming that they were doing everything that they were trained to do, right? Like, sometimes that will happen. And so I think like being really clear about that upfront and then another thing that we do is, we do like reviews after the fact often. So we'll look back and what I'm interested in is figuring out like patterns for individuals, right? Like, maybe someone is like, I don't know, too narrowly focused on one fandom or they're always like borderline inappropriate or sexual in their jokes. Like, I'm less, that's hard to be like, hey, so just some feedback or some constructive feedback. You're a little sexual in your proposals. You get toned down. You want to put doin' a thong too much. I know you enjoy this, but I try to make it less about one-offs and more about like, okay, throughout your body of work, where are the areas where you can tweak and people who succeed have to be willing to take feedback. And that's like important. Where the people who haven't been able to take that feedback. Cause when you were with creative people, it's like personal. Yes, so there are people where it's like easier and harder to give feedback. Sometimes it's a matter of like figuring out how they hear it best, right? Like, sometimes it's like better coming from up here than a manager. There are people who are challenging to get feedback, but not so challenging that it was like a no-go, I would say. Dueling-go is really invested in hiring people who are not dicks. Like, it's like actually one of our values. You need resilience for that. You need resilience, but you have resilience and not like, not be a dick. That's awesome. (laughing) - No, I feel like I've seen the spectrum and was like, it's tough, creative people are tough, it's different. - Yeah, yeah. - You obviously went through a lot of areas of culture and media and marketing. And I want to talk about taste. Cause that's like the big buzzword of 2026, especially in this era. How do you know when someone has good taste? - I think that it means that it's someone who stays curious and really wants to understand the why. Like, I think often taste is mistaken for judging art, yeah, for judgment. And I don't think that's what taste is actually like. You should be able to find the why behind anything. Even just today, we were talking about, have you seen those like AI fruit dramas on TikTok? - Yeah. - They're crazy, right? But it's still a form of art. There's something so fascinating about it that like, why is this something that so many people cannot look away from? It is clearly hit some kind of mainstream accessibility. Obviously it's hard to say that like AI fruit dramas are high taste, like that's not what I'm saying. But I think like, I appreciate that in our team and in dual English culture, we can be curious enough to be like, what is it about these AI fruit dramas that it's like working? Like, is there something in the like short form drama space that we can adapt for our work? That is good taste, right? Like not shutting the door on creative endeavors. - Got it. How do you assess taste in an interview? - Ooh. - What are red flags, green flags? The biggest green flag is the ability to get into a creative rift with someone. - So I have on the spot. - Yeah. Like just like feeling like their energy has so many ideas like, what if we did this and what if we did that? That's what you wanna optimize for. Some creatives work better alone. But I think in corporate environment, it's like important to have someone who can build on others ideas and so also like optimizing for that. Yeah, that's a green flag. What's a red flag? You're like, oh, this person doesn't have the sauce. (laughs) To me, probably someone who like I feel like is too focused on one creative point of view. Like whether that's like ego or they only see the good in like one type of work, there are definitely creatives that can be very successful, right? Doing that like art is a lot of that. But I think at Duolingo, we want diversity in our creative and like balance. And so that's probably a red flag for me. So I guess to assess for someone with good taste, you do kind of a live case study where you're trying to find the riff. Yeah, I try to ask questions where, you know, get into their prior work like ask them like, what would you have done something differently? And then we can kind of start talking about the creative and like what they thought worked about it, like what would they carry over into Duolingo and then that becomes your conversation. And you said earlier, a lot of the work is copywriting and I think that in social media, copy is king to be honest. Yeah. How do you test for great copywriting skills? That's usually a case study. Oh, a case study. We usually do a take home task that's like four hours and it sort of depends on like the role. But for social media, for example, like it might actually just be like, give us 10 post ideas, like let us know what you think. And so you're like, okay, let's schedule the four hours and then pantry. Well, we recommend that they only spend four hours on it, but it's sort of like up to them. You can sniff out AI copy, right? Definitely. There's also I feel like so many like AI take home tasks, complete tours now. And it's like so obvious. Some people don't even reformat. I've got a lot. Yeah. I'm like, this format is exactly a copy page. Yeah. Exactly. How dare you. And anytime copy is like, it's not just ego, it's creativity or it's not just this. It's that. That's AI. Oh, killing me. Can taste be taught? I think taste can be learned. Taste is about understanding your own creative point of view and being curious about others' creative points of view. And so I think it is something you learn and evolve over time. But I don't know that I can teach someone to be curious, but I think someone can learn it for themselves. It has to be like a self-guided journey, I guess. Ooh, damn. Probably high taste and poor execution skills. 'Cause I have to think execution skills are easier to teach than taste. It's harder to venture between someone who's ideas are cheap type person versus someone who can actually give an idea that has legs. Yeah. And I guess that's just based on your own taste and personal judgment. You ever call people out to be like, that's not a real proposal. What kind of, what kind of biased idea was that? You ever humble someone? In one of the ones, yes. But not in groups. All right, can we have all the play groups? I gave a big idea. Oh, Jesus, I gave a big idea. I'm like, I think the team should do this. I'm so bullish on it. We're gonna go so viral. Just trust me, guys. Also, I'm gonna be out for the next two months. Yeah, I think that in the meeting, I probably say like really glad that you're bringing ideas to the table. That's really great to hear. Yeah, you know, I've got you, Kat. I'm like, I'm always here for you, Kat. Would love for you to maybe go away and think about what a proof of concept would look like so that the team can really understand your vision better because right now it's very abstract and not concrete enough. That's what I was saying in the meeting. And then in a follow-up 101, I would be like, hey, like, you know, I think, again, I do genuinely think it's great when people come forward with ideas, but since you're gonna be gone for two months and it sounds like what I can tell, you don't wanna ex-you don't it. I think it's really hard to expect that the team would want to ex-you don't have an idea that they are not a part of developing because they want autonomy too, right? Like, as I'm sure you do as well. Yeah. But Kat, don't we want to be great? I feel like it's a great idea. You see my vision. (laughing) You like my vision. Do you see that, I do see the vision, but now I wanna see you come back with a prototype and build the first step. If you believe in it, you gotta put your skin in the game. Got me. Got 'em. How did you build taste in your journey? And what was it in your experience for? I do think I was really influenced by my time in Ecuador, like I told you. My parents moved around a lot when I was young. I moved a lot with them. I think being exposed to so many different cultures, so many different ideas of what good creative is. And also seeing them from an outsider's perspective really helped me stay curious and try to see the value in everything. Literally everything from like hard science fiction, like three-body problem to like, germione fanfiction, like I see the value of it. Is that what you're saying? (laughing) Are you into that? When I was young, great was. I probably. Yeah. I mean, it's a leverage. Exactly. I love that. Exactly. Avatar last year at Mender only. the anime like I've only watched the yeah yeah are you Zuto Katara Zutara I don't ship anyone in in Avatar last time right I got into when I was too old like I think you like really true shipping like you have to I don't know like maybe be in high school when you're exposed no and I think like now so much of culture is driven by fandom like in a way that at least when I was younger was like almost something that you were ashamed of in a way that I think is really it's great it's really awesome to see and yeah so I do think like everything from hard science fiction to AI fruit drama to fanfiction like there's artistic value in it can you walk me through your train of thought when you say curiosity when it comes to a very interesting content piece I don't like anyone to say like oh I'm not curious about content pieces so what is the difference of like the baseline of what you actually mean by you're you're actually a curious person about like great pieces out there great pieces of work there's no one out there to be like I'm not a curious person it's the willingness to have a conversation about like the minutia of a piece of work like whether it's the word choice or the tone or the camera angle or like even the way that you know you set up this whole space and you were like oh I want that like the banana and the cookie jar to be over there yeah bring this lighting over here that shows a willingness to engage in craft that shows curiosity right like because taste is like about those details and if it's all the same to you then you're not like diving into the craft that's true so tasting after a different but related how would you describe interesting differences in similarities taste is about the ability to articulate the why behind a judgment call on something that is subjective it's about explaining why xyz choice is better for this audience than another craft is related because I think it's also about the nuance and the detail but craft is more rigid and a little bit less subjective right like it's like and actually I mean I'm not as good about it at it sorry like technique or something yeah like technique or like knowing what kind of camera to use for what shot like knowing how to color something in post like that's craft to me and actually something that I want to get better at oh yeah especially going back into music and stuff yeah how would you advise someone to build their taste today in 2026 consume voraciously outside of social media voraciously as an sat you actually need a ton of different source of inspiration so like whether that books or museum or anime or nature or going for a walk I mean I would not call myself a content creator but like as a content creator if that's what you want to do you need to find sources of inspiration that are very far from your medium because it will like spark more exciting thinking I think I agree what are great pieces of content and work that you recommend that embodies great taste to you I'm just gonna say three things that I love okay okay yeah so read the three body problem it's an incredible series trilogy but it's super fabulous was that totally worth the time yeah we're in a literary crisis I don't know how easy it's going to audiobook it audiobook it all right frank ocean I think in like 2010 or like 2011 released a letter on his tumbler where he came out oh my god and this letter to this day is like I feel like one of the it moves me every time I read it's a read that it's quite kind of like poetry he's an incredible writer I love Frank Ocean you know this tumbler post is still out there it's still out there I actually do think like Christopher Nolan is one of the best filmmakers out there right now like no one else marries entertainment and arts basically yeah I expect Odyssey isn't be really good but my favorite movie of his is inception why do you like Christopher Nolan films is it the visual filmmaking part or is it scripting both like I actually think he's a genius on both levels really great at plot good at dialogue and then like visually very ambitious was that one movie that it was hard to listen to everything and then they're like going backwards walking backwards tenet I didn't love tenet do I couldn't hear anything I know I need subtitles on this I feel like tenet was like a like a pandemic like an audio issue with that right it was like it was like some sort of like pandemic flute like tenet was not my favorite of his movies it's okay everyone deserves a flop yeah exactly one of my girlfriends said that who was in marketing 11 labs head of partner marketing yeah she said the script of the matrix is by far the most interesting piece and the content ever I loved it and I was like a script I've never read a script yeah so I got to read the reference there is no spoon for all the matrix lovers out there we in this AI era we cannot deny that I have like a love hate relationship with AI in creativity and you're in marketing and creativity where is AI actually useful in creativity where's it not and where's it dangerous I think AI can be useful as a jumping off point if you're stuck I have actually recently found like voice mode to be pretty useful to just like talk through mental blocks and like try to spark you basically I think that's it's useful there I think that it is not generally useful in coming up with the final idea like I have never felt like any idea that AI gave me is one that we can ship right AI is like a big flattening of everything like the whole way at least to my understanding AI works is that it essentially is just trying to predict the next word in a sequence yeah and so it naturally just like takes an average exactly everything is an average and good ideas are all about being not in the average yeah they can be like a human brain for that yeah did you go to can this year I did not go to can yeah but my Boston the RCML yeah I went last year and I didn't go this year the headline was always like embrace AI yeah in marketing and advertising and storytelling and everyone's like very positive about it but it's definitely a super ambivalent space I think public consensus is we hate it and art we don't want it to replace artists no replacing musicians no replacing artists no replacing filmmakers but then AI makes executing cheap and then we talk about like taste becomes the greatest human differentiator so I think there is a level of like we shouldn't depend on it yeah but I like the spark for sure I agree with the spark I've never found a shipable product either yeah where do you think it gets dangerous for people especially if you grew into your adulthood with AI and because you didn't grow up with it I didn't grow up with it either so I do think people use as their crutch I mean that was what I was to say like I think is the danger part it's like twofold like one I feel like I know some people who are even who didn't grow with AI who are becoming like emotionally dependent on their AI like therapy or kind of like therapy but also just as like I would rather talk to this chatbot that infinitely validates me than like a real human who might challenge me and make me uncomfortable like AI doesn't make you uncomfortable like yeah I will skew towards supporting your views yeah and I think that is one it's pretty dangerous how do you find AI most useful in your workflow actually I actually struggle a lot I went to a cursor dinner last night and then I went up to someone at cursor and I was like hey I'm not here to network I just need cursor save my life how do I make it better so I can go to sleep early like I don't want to network anymore I'm done just tell me how can we do a workshop right now yeah I don't need the the bells and whistles like I don't need this fancy dinner just tell me believe yeah how are people using it and I think that I would love for it to automate a bunch of things but I think everything for me is like if it works only 80 or 90% of the time I'm not using it yeah because it requires you to validate and double check and I'm like I'm not trying to do that my suspicion is like it makes sense to not at all use AI based or like almost not at all in what you believe is like your core superpower like yeah for you that's probably your content but for everything else where you're sort of like not as familiar yeah then you it probably can get you like 80% of the way there right it's like that last 20% that you need to preserve Ronnie Chang in this year's Harvard commencement speech or one of the class days he says your job as a generation is to beat AI and I think he meant to like kill it yeah I interpret it as be better than it like it shouldn't it's not the bar and I think that for me in my strengths I guess I just I just think I'm better I was like your output sucks so I'm just use my brain like that's just easier than me talking to you back and forth like I'm gonna just use my brain and off the dome yeah yeah yeah I gotta work on this critical skills but then sometimes I feel like if I just a day where like didn't use a ton of AI I'm like wait am I behind should I have been using more AI yeah yeah yeah it's it's a whole thing now another buzzword is storytelling has that been in your ecosystem I've definitely noticed a lot of more titles that are like storytelling yeah like yeah old titles yeah actually in December the Wall Street Journal published an article called companies are desperately hiring for storytellers so Microsoft and Vanta and Notian they're hiring for like head of storytelling or merging social comms PR into one department called storytelling yeah what do you think that actually mean because they're plight they're not hiring screenplay writers right they're not hiring novelists what does that mean in corporate America I think it means that it's like the person that's trying to write the script of what they want people to believe about the company and then implementing it across whatever channel they can like honestly it's probably a repackaging of comms that's probably what it is I was talking to a girlfriend who has been working in comms for her whole career and she said that usually comms is the first team to go to be the most unnecessary but now it's coming back I so what but I think it's because everyone has a megaphone now right and like I feel like for companies are like trying to figure out like how do we harness everyone's megaphone like so many companies are doing these like employee generated content programs like they want to get their narrative out in every channel possible and the storytellers like I almost see them as like a like a conductor in that way right there like conducting the orchestra of so that the song sound hormone - Oh, that's a visual. - Yeah. - What's the difference between reactive and proactive storytelling? - I mean, I think it's like a way that we think about how to show up as a brand is like reactive. So like, I don't know, like tweeting about a minor and Kendrick Lamar during the Super Bowl. (laughing) Or responding to like what's happening in the World Cup and like Norway going viral on the World Cup. That's reactive, like stuff that you don't plan for, but you plan capacity for of like, I'm gonna get something out in a day. And then proactive is like the narrative storytelling that takes a long time to build like, sweet game. - We always plan for some reactive because we actually feel like a lot of our most impactful work is completely unplanned at the beginning of the quarter. And so we like leave a little bit of room for them. - It's a lot of proactive stuff to be honest, that takes the long term and then the whole operating at internet speed allows you to be reacted in time 'cause social just happens so fast. Are you triggered by the word authenticity? - Yes. - Can you tell me about your traumatic experience with that word? - Wait, are you? - Obviously. (laughing) - Obviously. That is like the canliance authenticity, AI, blah, blah, blah, blah. - It's just such a big word. - It's a big word. - Yeah. - Like, yeah. - Tell me what you mean by authenticity. - It can be interpreted in any way you want and yet when you use it, it's always positive. And so I like try to strike it from all of our communications. - Yeah. - Oh my God. That is a corprensible thing. - Don't be authentic. - Don't use that word authenticity. Or else I will throw my laptop out the window. - Just like, tell me what you mean. - What does authenticity mean tactically? - Tactically, I think authenticity means like knowing what conversations make sense for you as a brand and showing up in a way that's really smart. So for example, I mean, an easy one for Duolingo is like anything as it relates to learning or language or cross-cultural interests or passions like K-pop or K-Drama, right? Like that is something that we have something to say about because we teach Korean. But we probably aren't gonna talk about the midterm elections. - Got it, got it. That makes sense. I wanna talk about a more personal topic that I'm also struggling through and, you know, knowing that you are a new mama. - He is. - And you're an ambitious career woman. How did you take Matt leave? - Okay, here's the thing that they don't tell you when you have the baby. Your body is raging with hormones telling you that all that matters in life is the baby. - Wait, this is after the birth or before the birth? - After the birth. Like it is like, I have a switch. - Everyone experiences it differently. - Yeah, activated. - Westworld. - But I think there's literally a biology that's like, you literally had the baby and then I was like, oh my god, let's have five more. Like you just like, like the pain just disappeared. - Yeah. - And you're like, oh, that was so easy. - And it's like all you want. And in fact, like when I was on Matt leave, I took like the full four months at once. And I, one thing that I loved is like my husband was able to take the same amount of time with me. And so we were like in this beautiful little nest. I was dreading going back. Like I was so anxious about it. I was thinking about ways to extend it. I was like, maybe I wanna be a stay at home mom, like truly, I think your biology changes. But then I went back and then after the first week, I was like, oh yeah, I remember why my brain likes this. And so I remember. - Yeah, exactly. Definitely what motherhood has shown me is how deeply we can change. Like honestly, 'cause I do think the biology of what happens to you postpartum is a trip. Like it is such a trip. - Did you get an epidural? - No. - I did a diber. - Did you get a diber? - Yeah, I did a home birth. - Holy cat. - Yeah. - Whoa. - I loved it, highly recommend. - I don't know if you're gonna do it. - I'm so pain-a-verse, like I'm a weakling. - Fair enough. - So they say that when mothers enter back the career, there is a motherhood penalty where they make less, they don't get promoted, they could get promoted. Like Deb Blue talks about it in her book, take back your power and she didn't get promoted. In fact, I'll demoted it in the seven years after. It took her seven years to come back and get her ramp back up. - Yeah. - And then fathers get a fatherhood bonus. The hell. - Did you experience this? 'Cause I'm deathly afraid. - I actually, I don't think I do think that I have to make a lot of trade-offs as it really, like in terms of time. Like for me, a big thing that I had to like really focus to get back was movement, like workout basically. Like something has to give. You just lose a ton of time. And so for me, the thing that I lost was working out and like I managed to, I have a super supportive husband who like takes care of Colette very frequently, like even today, right? I'm flying out here and he's gonna do childcare the whole day. As an ambitious girl boss career woman and a new mama, can you have it all? - Hell no. - Oh no. - But I think you can find balance and you need to like decide what trade-off is worth it for you. - I don't want it, can't. - Yeah. - I also think I am lucky I have not felt the motherhood tax. I think because Duolingo has like a really strong culture of supporting parents, which I like. And my role manager also I think has like been super supportive all the way, but I also, I still prioritize work. I will say that. Like I prioritize Colette and I prioritize work and other things have fallen by the wayside. - I definitely feel horrified. And then every parent talks to me and then they're like, you need to prioritize. I think I do minimize my pregnancy a lot. And I like try not to think about it too much, but then I did not perform as well this year to my expectations. And I beat myself up a lot for it 'cause I've proud myself on outputs so much. And then when that went down and I couldn't like try a little can, I couldn't like go to New York or go to San Francisco as much and then make this as much as it was. Like it really hurt my confidence. - That's the NTJ and you. - I will say something to you that someone said to me that I have found helpful. Like, which is hard for me to believe, but I actually think it's true. She was like cat. You can probably put in 20% of the effort that you do and still make it 80% of the way. - Yeah. - Which I sort of hate. - I know. (laughing) Like, I can't say that I live by that principle, but it's like you just use it to survive. - Exactly, but bye. - But I think there are times where you have to recognize like you only have so many hours in the day and also that the different chapters of your life like require different things of you and being a parent of a young child does mean that you just have like less time to focus on other things. - Okay. - But the happiness that you feel when they like take their first step or hold your hand or learn to hug you, it's pretty great. They're really fun and they're really funny. - Okay, I hope the kid is funny. 'Cause I'm not trying to be boring. - Great. - No. - Having a bored life would definitely be funny. - Okay, yeah. I think I'm just like feeling the anxiety. Like, I like how to a crisis this week and I was like, and then last night was the first crater networking dinner I went to all year. Last year, I went to like two or three a week, which was like honestly insane of me, but go ahead and do what I go ahead and do, you know? - You'll probably get back to it. - I will do my best. I talked to some crater friends, 'cause like in crater business, you know, algorithms don't know your on-mat leave and they'll penalize you for leaving. And some crater friends were like, you should just expect to take three months off no posting. - Yeah. - And I was like, what do you mean? Can I, what can I just come back to work the next day? Like can I just, but yeah, I think I'm just a little freaked out. - Do you sort of have a plan for how you want to approach it? Or are you gonna kind of take it day by day? - Just podcasts, I have to bulk film as much as possible. But it takes me a lot of effort to prepare and like have guests and I'm really precious about my episodes right now. And short form long form, it's a whole production. - Yeah. - Yeah, thankfully I'm building the team. So that will be more support. But I think that I'm in this place where I could be peaking in my career like getting to a strong peak and supporting my friends and crater friends. And like as an Asian woman, we don't get a lot of opportunities and we have to really advocate for ourselves and my Asian girlfriends who are creators don't advocate for themselves. And so I almost feel like I'm one of the people who are trying to push that narrative to all the power players and influential figures who are working in the inside. And then it's just, Targon, I want to see all of us rise. But I see like a lot of us get passed over or forgotten or not put on top of the roster for a certain pitch. And I think we have to be able to position ourselves as if we were our own white man. - Oh yeah. - Yeah, I really love that. I really want us to win and thrive. At the same time, it was time for me to start a family. Like, it was really intentional. But I think I'm just like, I know this is what we wanted. And I'm still sad about the consequences and those can be true. - Both things can absolutely be true. - One tip I have is to have an explicit. It can be tough, like have an explicit conversation with your partner about what you need from them in order to still feel fulfilled as a person, as an individual, and make sure that they're willing to support them. - What's something you needed? - I mean, this is like a very tactical example, but I work East Coast hours 'cause Julingo's an East Coast company, but I live in California. And so I never do mornings. Alex does every single morning from wake up to na, pick up. - Yeah. - He takes care of Colette and I do the afternoons. And like, that is a trade off. Like, that makes me sad, right? Like, on days, it makes me really sad. On some days, I'm like, oh, thank God. - Yeah. - Yeah. - That's fair, that's very tactical. - I heard light becomes really logistical. - It does feel very logistical. - Yeah, you're gonna be good at your logistics. - Yes, yeah. - Before we wrap, for better or for worse, we must conduct what is called a performance review. - Dun, dun, dun, dun. - You know what that is, right? I've never had a performance review on it. - Legally, this is not affect your compensation or your title, but it does affect your aura, which matters a lot in the social spheres. - Yeah, let's do it. - Catchan, would you rather be right or be promoted? - Right. - Oh, it doesn't care about money. Would you be down to make a million dollars but you had to be a course person? - No. (laughing) - Should filming a day in the life, working in tech be banned or permitted in the office? - I think it's fine. - Okay. - I think companies want it now. - Dude, I got in trouble so much for in the past. - Yeah, I got flagged and they're like, no. I can't do this. I'm like, well, you didn't have a policy on this. - Yeah. - You had your receipts. - Are you living with main character energy or are you and your NPC era? - NPC era. - Nice. - Same. - Meetings before 10 a.m. Human rights violation or a personal problem. - Personal problem. - I have to wage many meetings before 10 a.m. I started six. - Girl, that's 'cause you're working east coasts out. - I know. - So it's my personal problem. - Yikes. - Out of 100% for a promotion, what percentage is skill and what percentage is visibility? - Probably 60, 40? - 60. - 60 skill. - I was 60 skill, by visibility. - That's right. - Is Genzi cooked or trainable in the workplace? (laughing) - Can I choose like a third answer, which is like, they should revolutionize the workplace. - Oh. - Right like maybe, like maybe a little trainer us. - The revolution. - He gives. - Do you think any PR is good PR, even if it's bad? - Yeah. - You do think so. - Yeah, I do kind of think so. - So I should start saying more controversial things that can get me canceled. - Maybe. - If AI completely took your job, would you rather be a plumber, electrician, or a firefighter? - Firefighter. - Why? - 'Cause I'm addicted to adrenaline. - Oh, and you're a hot body builder. - Yeah. - What have you been humbled by recently? - Oh, we're doing this hackathon at work. And actually like today is like one of the hackathon days. And I'm trying to build this product thing. It was like a very rude awakening to realize like, wow, my hard skills are basically useless. Like I needed to just recruit an engineer, a designer, and like a learning designer we call them, which is like the content specialist. - Yeah. - I was just there to like help everyone along and do a bunch of grunt work. - Rough. - But it was good. - But I was humbled. - Who bullies you more? Your CEO, Louise, the CPO, or your CMO, or social media commenters? - Ah. - Social media commenters. - I gave you a now, I gave you a now. Manager or super icy? - Manager. - Okay. The last question is a taste test. - Ooh, okay. - I'm gonna name some random cultural phenomena. - Uh-oh. - And you have to rate, love it, or hate it. - Okay. - The first one, Skibbidi Toilet. - You do love it! - You wild for that. You wild for that next one. - Barb and Hymer. Yo, this was great. - It was so good. - This was a perfect, like, cool programming. - Dune popcorn bucket. - Hate it. - Yeah, it's weird. It's weird. - People put your hands through it. - Right. - I know you don't watch Love Island, but Melanie leave that man, brand post. So this is where Melanie is on the cast of Love Island. And there's this man named Sincere that they have like a-- - Great name. - It's about toxic relationship on the island. And brands like Melanie's still on the island. - Yeah, yeah. - And so brands are like Melanie. We'll give you a lifetime worth of brand products and services. If you leave that man, Sincere, she's down. Do it, be like Melanie. I'll give you a lifetime subscription to do a Lingo. If you leave that man, Sincere. - I will teach you every language. I will teach you the language of love. If you leave that man. - That was so good. - Off the dome. - You know what? I love when the internet gets behind someone. It's a little wild. It's a little wild of the internet and brands. Okay, the word authenticity. - Oh. - Ew. I don't know if you know this. NPC live streams. - I do know what this is. But I don't think I know enough about it to say I love it. - It's like streaming for eight hours a day and then every time someone buys a little digital item, you're like ice cream, yum yum. - Yeah. (laughs) - Ice cream, yum yum. - Ooh. - Like that. - Too much. - All right, no, hate it. And then last but not least, Spanish or Spanish. - I love it. - Yay. - Well, Kat, you have received an overwhelming exceed expectations. - What are my stock options? - You get none. - You get Chloe stock. - Chloe to the movie. - I'll take it. - I'll take it. - Yeah, lifetime relationship and text follow up to give me my life updates. - Coffee dates. - Aww. Thank you so much for being on Office Drama. My question is, where can people find you if they wanna reach out to you? - I think I'm sort of on LinkedIn. - You are sort of on LinkedIn. - I sent you a request. You wanna accept it? - I will accept it. - Thank you. - Thank you. - Are you open to people called messaging you on LinkedIn? - Definitely, yes. Though I check it sporadically, I would say. So do not get disheartened if I don't respond immediately. - If they do, what will increase their chances if you're responding? What kind of message? - Be specific and to the point about what you want. Like I feel like people always want to be like, oh my god, really admire your work or saw this. Like, no, just like you're messaging me because you want something and I'm happy to hear it out. - Got it. - Yeah. - And Kat-chan, would you ever wanna come back on office drama for a future episode? I would love to. - What like life milestone or time of life you would want to come back and give a life update as we're here to follow your lore. This is not this, the only time we're gonna experience Kat and her brain. - Let's do the second chapter of duo because I think his first chapter was his mascot era and now he's like entering his sophomore album phase and we should like come back after we do the next chapter. - What is that? - What is that? - Is that like next year? - Well, we're trying to figure it out right now. - Okay. - Okay, all right. - Yeah. - My people will get in touch with your people. - Oh yeah. - Thank you Kat! - Thank you! - Shout out to our drama llamas on Patreon. - I've been posting a lot more there lately like two weeks ago. I went to the Patreon SF office to shoot and a man oh man, I had the biggest production emergency ever. So I flew in to San Francisco because I'm from LA. I think people forget that I'm based in LA. I fly in as a firefighting. I batch into the office at like 11 PM on that Friday. I go to the equipment room where I have all my stuff and my badge doesn't. I am locked out of the equipment room. Ah! So I frantically text workplace and posted on the IG story to ask if anyone had the stuff I needed. But yeah, I literally don't know as single soul in San Francisco who has the equipment I use because I use some really beefy stuff. I'm a huge tech head and I use very, very niche equipment. Thankfully, the next morning on Saturday, workplace responded and we got in, ah. But if they didn't, I would have been so screwed. Anyways, I share my chaotic behind the scenes on the Patreon. I think I'm gonna share way more work and progress thoughts and feelings there. For example, like the whole chat GPT open AI brand trip controversy has been in my circle of conversations lately. But yeah, I haven't really talked about it publicly. It's a scary piece like you have to be ready to be thoughtful and be high touch and be prepared to have a very nuanced conversation on the internet, which is really hard to do. So I will do a piece on this very soon. If not, it's already published, but yes, very, very soon. So check out our Patreon if you wanna be part of the behind the scenes process. And like my thoughts building up towards these pieces and interviews. I'm gonna have a big journalistic piece on this very soon. So check out our Patreon if you wanna be part of the behind the scenes and like the building up towards these big journalistic pieces that shape modern work. Now, my thoughts on this episode, dude, I cannot believe I was able to pull someone like Kat Chien. I don't know if you understand, but people like Kat just do not go on the internet. Like the amount of white glove service, research, editorial work, you need to do to build trust and rapport with these types of executives is out of control. I mentioned that this interview took me at least eight full research hours to prep because I really see these as long term relationships and it is a privilege and responsibility to write or rewrite people's narratives in their digital footprint. So I take this work very, very seriously. It's pushing over to a new topic. If you are in LA, I will be speaking at the Crete and Cultivate Festival happening on September 19th to 20th weekend. What is that? It is the world's largest festival for women in business. And the greedy is speaking, a lingerie cartoon from Love Island speaking, Alex Earl speaking, Cardi B's performing. I am pretty new to the woman in business space. I think I went to this festival for the first time last year. A lot of the people attending are in CPG, media, entertainment. So not a lot of tech people, but there are a lot of tech brands. And this is the new space I gotta work in. I am so stoked to have this chance to speak on stage because representation, you know what I mean? Like people like me do not show up at these spaces. That's what I'm, that's what I'm trying to say. Like can lions, oh no, people like me do not. We are not in those inner circles. Like we do not go on the stages and we do not have that platform. So it is a gift for me to step on that stage and represent and advocate for myself. You know what I mean? Hopefully more opportunities will come. I do have to do only local events though. I'm not allowed to travel at the stage of pregnancy and after I give birth, I don't know what's gonna happen. So I'm really hard. It depends on how breastfeeding goes. We'll see. Please, please, please let me know what you think of today's episode. And I will see you in the next video.

Podcast Summary

Key Points:

  1. Cat Chan’s career spans diverse industries including social media, influencer marketing, Tesla, and Facebook, highlighting her adaptability and deep experience in creative and tech-driven environments.
  2. She emphasizes that good taste in creativity stems from curiosity and the ability to understand “the why” behind content, not just judgment.
  3. Duolingo’s culture thrives on trust, speed, and creativity, with minimal top-down approval to enable fast, autonomous ideation and experimentation.
  4. A core principle of Duolingo’s social strategy is embracing humor, absurdity, and even mild violence as a form of engagement—only when aligned with the brand’s mission of making learning fun.
  5. Cat Chan values authenticity and emotional safety over perfection, arguing that creative risk and failure are essential to innovation.
  6. She learned that corporate environments often suppress individuality, leading her to prioritize a workplace where self-expression, playfulness, and psychological safety are valued.
  7. Taste is not fixed—it is cultivated through exposure to diverse cultures and creative forms, such as fan fiction, AI-generated content, and global pop culture.
  8. Hiring decisions rely on direct experience and trial periods, with a strong emphasis on chemistry, adaptability, and the ability to work in ambiguity rather than just technical skills.

Summary:

Cat Chan’s dynamic career journey—from social media at Live Nation and Red Bull to high-stakes roles at Tesla and Facebook—reveals a deep commitment to creative freedom and authenticity in marketing. Central to her philosophy is the belief that good taste isn’t about judgment, but curiosity—the willingness to explore the “why” behind any creative work. At Duolingo, she built a culture where trust, speed, and playfulness are prioritized, allowing teams to operate at “internet speed” with minimal bureaucracy.

This environment fosters creativity by removing fear of failure and enabling experimentation, even with controversial humor or edgy content like violent or absurd social posts. Cat emphasizes that such risks only work when rooted in a clear brand mission: making learning fun. Her experience shows that corporate environments often stifle individuality, leading her to value workplaces where self-expression and emotional safety are central.

She believes taste develops through exposure to diverse cultural forms—such as fan fiction, AI art, or global fandoms—and that creativity thrives when teams are encouraged to question, debate, and innovate. Ultimately, Cat Chan champions a philosophy where success isn’t measured by perfection or compliance, but by resilience, curiosity, and the courage to take bold, human-centered risks.

FAQs

Good taste means being curious and understanding the 'why' behind creativity, not just judging it. It involves staying open to diverse ideas and being able to see value in different forms of expression, from AI-generated content to fan fiction.

Duolingo creates a trust-based environment where teams are encouraged to experiment, move fast, and take creative risks. They avoid rigid approval processes and emphasize collaboration, independence, and learning from mistakes.

The brand leans into fun and absurdity because learning should be enjoyable. Characters like Duo are unhinged and playful, which helps the brand stand out in a crowded digital space and build emotional connections with users.

The team sets clear guardrails—like avoiding violence or explicit content—but treats these as floors, not ceilings. Creativity is encouraged as long as core values like fun and learning are maintained.

Culture is the new marketing funnel—Duolingo enters existing cultural conversations (like K-dramas, gaming, or TikTok trends) to become relevant and build genuine connections with audiences, not through traditional advertising.

Interviews focus on a candidate’s ability to engage in creative conversations and generate diverse, thoughtful ideas. A live case study or portfolio review is used to evaluate originality, adaptability, and openness to feedback.

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