Storytelling in Tech: Inside Commerce AI

Speaker A: Welcome to Wharton TED Talks, the official technology podcast of the Wharton School, where we host forward looking discussions that enlighten and inspire. I'm your host, Gaurav, and today we're joined by an amazing guest. Uh, I could introduce her, but I would love for you to introduce yourself, Lisa, and tell our audience a little bit about yourself.

Speaker B: Sure. Thank, uh, you for having me, Gaurav. It's exciting to be here. Um, my name is Lisa Yamner. I'm the co founder of Daydream, which is a conversational shopping platform that uses AI to put the center back at the. Sorry, rather the customer at the center of the shopping experience. Um, creates a truly personalized experience. You can talk to Daydream as if it's a personal shopper, um, and find everything that you need.

Speaker A: Yeah. Amazing. Yeah. I've played around with it and we're definitely gonna dive into that. Uh, before we get into more, I would love just do a recap of kind of your background leading to Daydream, uh, how you've moved through the tech industry, a little bit of what you've done before.

Speaker B: Sure. Um, I spent 12 years at Google, um, which was a, um, really exciting time to be at Google. So I was there from 2005 to 2017, which was a time in Google's history where it was post ipo. Um, the company was flush with cash, tons and tons of opportunities, and actually not nearly enough people to execute on all of that. And so it was the type of experience where it was like, if you had an idea or something that you wanted to work on, all you had to do was raise your hand and the next thing you knew you were assigned to the next big project. So you had to be very careful, um, what it was you suggested. But it was really fun for me to be so early on in my career and to be able to sort of take these jumps, these jumps and challenges and see these opportunities. So when I first got there, um, I had moved to New York from D.C. and it was the 2006 congressional elections were coming up, and at the time, nobody, um, political candidates weren't using the Internet for advertising. Which sounds insane to say in 2026, but it's true. Um, they were still exclusively using, like, tv, radio and outdoor. And so I just sort of said to my boss, like, wouldn't it make sense if we tried to get some of these political candidates to use Google AdWords? And he was like, well, sure. If you know people and you want to try it, go for it. So I had met Some people who worked at some of the political advertising firms in D.C. and I picked up the phone and started calling them and everyone was game to give it a shot. And so I got to start the first, um, campaigns and elections team at Google back in 2006, um, which was obviously successful and has since taken off over the last 20 years. Um, and then following that I actually had been um, a, um, Latin American studies, Spanish, ah, and history major back in college. And so I wanted to kind of put my Spanish to use, um, and some of that. And so I got to work on a, um, project opening up some of Google's Latin America offices, um, bringing some sort of US Hispanic advertising kind of more to the forefront of Google's offerings, um, and then actually proceeded to help open up Google's first Miami office. So all of that just sort of came from me acknowledging that there was a gap in some of Google's offerings and moving forward with that. Um, and then I had my first baby and I came back and I no longer wanted to be traveling to Latin America all the time. And was actually sort of a, uh, it was a very opportunistic time where Google was transitioning from working, kind of dividing up the business from having 12 verticals to 36. So it used to be like retail, travel, finance. And then they expanded it to not being just travel, but like airlines, hotels, aggregators, et cetera. And on the retail side previously, like Chanel and Home Depot had been covered by the same team. And so I was given the opportunity to break out fashion and luxury into its own vertical, start up the first ever team dedicated to fashion and luxury and really start helping brands use digital for discovery, for storytelling. And I would say that's like, in many ways, like where this story begins was, um, it was, you know, at the time, it was 2012 and Chanel had never put a video on YouTube and LVMH was in the middle of suing Google. And these were supposed to be my biggest clients. And um, and I really had the opportunity to um, help fashion understand how digital was a safe space, how it could really be a place that helped bring their brands to life, helped customers discover them, um, discover their key pieces, their heritage, et cetera, um, and then also help Google understand the influence of the fashion industry, why it was important, why they needed to sort of pick up their heads and take note. And so it was a really fun six years building that team, building this sort of presence, building this intersection between fashion and technology that I now think has come so, so far. And has become somewhat the forefront, um, of very much what's going on. And so, um, after I did that, I had a brief rebound at Conde Nast. Um, we're actually at a great time. I worked with some great people, realized it wasn't exactly where I wanted to be to continue building my career. Um, and then I was introduced to Julie Bornstein, who's my current co founder and who had just raised funding for a company called the yes, which was um, a personalized women's startup fashion app, uh, which we built together, brought on um, over 300 brands and um, within two years of launching, we're actually acquired by Pinterest to go ahead and build the backbone of Pinterest shopping using our technology. Um, after being acquired by Pinterest, Julie and I spent about six months at Pinterest before realizing, um, that there were just some big opportunities going on in technology, some that we just couldn't resist. And so we left Pinterest, um, and went back to two of the former investors from the yes, found two more and raised 50 million to start building Daydream.

Speaker A: Amazing. Uh, I love an ads person. Uh, I come from ads. Um, I helped build the SMB advertising platform at Snapchat and I was one of the earliest people on the Netflix ads tier back in the day before business school. So I love an ads person.

Speaker B: Um, it's, it is the backbone of the Internet industry. I'm not sure where we'd be without ads to fund it. Right.

Speaker A: No, I'm a big supporter of it. I 100% agree. It's one of the most important and oldest business models. I do want to ask you a little bit about this intersection. We're going to talk a lot about this intersection between fashion, technology, um, kind of going back to early days of Google. Um, you mentioned, you know, Chanel, lvmh. These are iconic brands that are very retail forward brands. These are, uh, very, very heavily crafted, uh, very, very specific stories that has taken decades to build. How was that initial conversation of bringing them to kind of a digital form, bringing them onto ads, getting them to run ads like this on kind of a newer model. How do you bridge such an old industry into the technology realm?

Speaker B: Well, the first answer was no. And I think the second and third answers were probably no too. Um, but then, you know, it was really about. The truth is, it sounds like it's, I'm simplifying it, but the truth is it's figuring out like, you know, what are the problems that they need to solve and what are the challenges that they're facing and then determining like how those, how the solutions that digital brings to the forefront, we're really able to help them solve it. And um, kind of before that, part of my time at Google, I had done this project where, um, we did this event called Day on the Digital Edge, which was we brought together the top, um, CEOs from all of the big ad agencies, the big, like, holding companies. We brought them out to Google's headquarters in Mountain View. We gave them all MacBook Pros to take home with them, preloaded with all these bookmarks of like, what the newest and best websites were, which was like, um, there was like a browser discovery thing called StumbleUpon and there was. Facebook was still new and there were all, you know, it was things like that. We actually sat with them, we showed them how to use all these different websites, set up Facebook profiles. So I was like the first Facebook friend for all these like, major like big honchos in the ad industry. You know, like, um, uh, Marvin or what was his name? Gottlieb. Martin Gottlieb. And um, Mike Hughes for the Martin Agency. And all these guys were just sort of sitting with them and remember, so this was at the time when Facebook did feel like a threat to Google. So we're getting all of them on board. And what we were doing was we were showing them how this new technology was going to help them move their businesses forward. And it was really very much the same thing when it came to working with Chanel or working with Louis Vuitton or any of the, uh, other brands, which was, yes, what you see is these annoying pop ups and banner ads from Dunkin Donuts about getting a free coffee with your donut. But you know, what we're here to show you is that digital is a way where you can tell much richer stories, where your brand can come to life in a way that it can't in the pages of Vogue. Uh, m. But we know what's important to you and we're going to help you find ways to tell that. And so we did things like we helped them create their YouTube channels and ensured that they were uploading their latest Runway shows and that we were finding ways where we could drive traffic to them and really show how all of this money and energy that they had put into these incredible shows could actually go a lot farther than just the editors and the buyers in the room. But now they had this whole audience waiting for them on YouTube to see what they were putting down the Runway. So it really was about finding what it was that they were struggling with or what was a bigger opportunity for them than the current businesses they were running and pointing to the solutions that we have for them.

Speaker A: Yeah, because I imagine that's gotta be the biggest hardship even now as we look at new models and new ways to sell products, is that these storefronts and these brands are so carefully controlled that it must have been hard to be like, well, let's take your brand and put it in a banner ad. You know, um, I gotta imagine that was the hardest part because I know from my experience with, um, working at certain companies, people forget how, especially at the highest levels, especially at that time, how much ads are, uh, conversations with salespeople, with brands and being like, come on our platform. We are, you know, we know we have a certain reputation, but, um, take a chance on us.

Speaker B: Yeah, I mean, we built a whole narrative around, um, shopping on Fifth Avenue, which I would say is actually still quite relevant today, which is like, you know, almost like if you think of the Google search results page as a, as a stroll down fifth Avenue. And um, the difference is like your store online is never closed, but the stores on Fifth Avenue do have to close at some point. And so this is your flagship store. Your website should be your flagship store. And this is an opportunity to continue to drive traffic into those stores when people are in that shopping mode. And there's something about that that still very much resonates. Right. Like, you know, you put all this time and energy and effort into these flagships. And I would say most, most brands do see their websites as their flagship stores. Well, now that you have the store and now that it's open all the time, how are you going to get people to go into it?

Speaker A: I love that kind of like the uh, the idea that your website, your online presence is now the flagship store in kind of the destination place. What do you think of retail now? I mean, I, uh, what do you think of brick and mortar? I know there's so much talk about one year brick and mortar's dead, next year it's the newest theme park experience. Um, as someone who's been disrupting that industry since it started getting disrupted, what's your thoughts on brick and mortar?

Speaker B: I think, um, it still plays a really important role. I think all touch points with the customer are important and they continue to matter. Um, I believe that shopping is a, is a privilege and it's a, ah, luxurious experience no matter what brands you're shopping that people do. Um, sure, there's a utility behind It. But the truth is shopping is emotional. And um, many times there's a reason why it's called retail therapy where it can make you feel better. And that needs to exist in all parts of a customer's life. So they need to be able to show up in a store and touch and feel a garment and, and experience it if they want to pick it up and take it home with them if they have something to go to that night. Um, they also need to be able to experience a brand online to understand what are all the options out there and maybe like, you know, what, what suits me and my lifestyle and what's good for me. But I think what's happened with retail is, I think it's gotten quite overwhelming, uh, or underwhelming. And there's like, you know, so the in store experience can be, you walk into Saks and there's racks and racks of clothes and everything is 40% off and it's not organized anymore. And it's not, you don't know where your sizes, you don't know where your favorite brands are. You don't even like, you don't even know what you're looking for. Or on the flip side, you walk into a store and it's empty and they only have like one size of each thing and it's not, you know, again, it's like not for you. I think where the opportunity really comes with shopping online is this ability to walk into a store. And I say this in quotes, walk into a store online that is actually personalized for you. So you, you know that you have an event in two days that you need a, you know, a new outfit for. Well, we can make sure that we're showing you only brand, you know, only, uh, stores that are going to have two day shipping and only things that are in the price point you like to shop in that are from brands that we either know you like or are similar to brands you like that are available in your size. Like, that's the opportunity with shopping online is take the richness and the beauty of these brands and marry it with the needs of a customer so that she's seeing what's right for her and not having to dig through the piles of what's right for somebody else.

Speaker A: I think that's such an important point because it's like, it's just like a collection of content, you know, and you're trying to customize it to certain people, but you have to, you have to find ways to delight and surprise people with any product development, especially in Fashion like to get people excited about what they're going to buy or spend money on, you have to find a way to keep them interested. Um, for Daydream, I know I was playing around with it myself. I was a little surprised when I signed up. I didn't realize that it didn't like I was expecting a survey. You know, you're always expecting surveys with these sites to learn about you. But it kind of just asked a very simple question. Can you tell me a little bit about the idea behind that and um, how you go about initially building that profile and kind of that data moat around the person?

Speaker B: Yeah, so we're doing a lot of testing and learning. Um, actually when we first released our beta, you did, you had to take a quiz in order to fully sign up and you had to answer some initial questions. Um, and then we, um, started, you know, then we said like, forget it, let's, you know, it was actually there were too many people who were coming and leaving and dropping off and so we wanted to test, well, what if we didn't ask them anything at all? And we started making, using their questions as sort of part of the shopping experience. Um, and then start really watching their signals. What are they, um, tapping, what are they saving, what are they clicking out to? All of those different pieces start to become vital. And as we evolve, we will keep asking questions and sort of testing which questions and answers are most helpful to make sure that we're continuing to deliver the right experience. Right. So in the future you'll see if you say, like, I'm looking for some new clothes to wear to work, the next question shouldn't, really doesn't necessarily need to be, well, what brand or, you know, what price point, but rather like, well, what do you do for work? And then that opens up like a whole new, um, wealth of information that can actually give us a lot of details like, you know, if somebody works in medicine versus works in finance versus works in advertising or their workwear is actually quite different. And just asking them about brands isn't going to get us all the way to like, the real nuance of that. And so, you know, it's, it's sort of, if we can ask questions more as part of the shopping experience, we start to get just a lot more intel about them. Now we will sort of introduce back the ability to take a quiz. Um, and what we found both from our time at the yes as well as, as we've been building Daydream and is that once you gain consumer trust and once they see that there's a real value in their answers. They just want to tell us more. And in fact, there's a frustration with, like, why isn't there a place for me to give you more information about myself? And so, um, we will be building that out as well. And all of that results in what we call your style Passport. So every customer on Daydream has a style passport. So it's entirely transparent. So you can see the information that you've given us. You can change it. If you decide, like, I don't like that brand anymore or my size has changed, or, you know, different things, you can go back in there and you can update it so that you're clear on sort of what information the system is drawing on to give you the next output and the next set of results.

Speaker A: Yeah, I know. It's that building that kind of parasocial relationship with this chatbot. And, uh, I guess chatbot's not the right word. How would you describe it? Would you just say chatbot?

Speaker B: I wouldn't say chatbot. Um, a chatbot probably oversimplifies. Actually, most of you know, it really oversimplifies what it does. You can chat with it and you can have a conversation, and I think there's a real value in that. But it's, you know, the, the North Star is that it is a, um, personalized shopper in your pocket. Um, it's not quite there, but that is what we're building towards.

Speaker A: Got it. Um, okay. No, I love that. The personalized shop in your, uh, pocket that kind of learns with you and grows with you and changes with you, um, as you shop and grow with it. Is the goal that you do all of your shopping through, uh, this or for specific events or how does that work ultimately?

Speaker B: Yes. So what we set out to fix first, um, and what we spent most of last year really building out was search. So search is really broken, um, across online shopping. Whether it's that you go to Google and you do a search and it's really sort of. You see everything from Tamud and even Marcus, and it's not personalized to you, um, or it's that you go to an individual retailer and not through their faults, but they're sort of built on an old tech stack and really dependent on manual tagging and you can't really search the way you want to. So that's what we've done. First and foremost, we fixed that. Um, we have over 10,000 brands represented on the platform, which means you can search and shop for everything from your Nike activewear to your, um, Gucci gowns. Right? So you can really search for anything. Um, and so I think, you know, as the technology continues to improve, the catalog becomes the only limiting factor. And at this point we have such a large catalog that there's really no reason not to shop on Daydream. Um, and ultimately we even would like to get to a place where we can help you, um, shop in store on Daydream, meaning I'm in New York, I have an event to go to tomorrow night. Where can I go in town? Like, where can I go within a five mile radius to find something great to wear to this event? I found what I wanted, I can reserve it in store, I could show up and pick it up. So, um, you know, those things are sort of a limiting factor currently of the kind of data that exists that we get from our partners. But you know, as they improve and we figure out more ways to help them improve, we'll all be working together to create that, ah, full functionality.

Speaker A: Uh, you mentioned 10,000 brands. I'd love to kind of dig into. Is that a deliberate choice? Like do you go through a bunch of brands, you go for an application process or is it based on like essentially what data and connections you have access to?

Speaker B: So to be clear, the 10,000 brands come from, um, a little over 3, 300 direct partnerships right now. So, um, what that means is that we work, we have direct partnerships with brands like Bottega and Chloe and Gucci, like we've been talking about, as well as brands like Levi's and J. Crew and Theory and Vince. Um, but then we also partner with most of the multi brand retailers. So we have partnerships with Shopbop and Net, A Porte, Revolve and Forward, Saks and Neiman Marcus and Bergdorf's, Nordstrom, et cetera. Um, and so having the multi brand retailers is what ticks up the number of brands. Um, for us it's very important that we have both catalog depth and breadth. So if we just had the retail partnerships, we wouldn't necessarily have the depth of catalog from everybody's favorite brands. Um, if we only had the brand partnerships, it would take us a lot longer to get to that breadth. So we sort of went for a combination of both. Um, we are, for our sort of initial phase, you can't boil an ocean. And so we are targeting a specific audience with the brands that we've brought on board. And we're continuing to watch, um, who our customers are and to learn from them, to figure out what brands are missing. From that mix, who we'd like to bring on, who we think would really sort of add to the richness of the catalog. There's an obvious. Some of the specialty brands that you can't buy at all from department stores are ones that we'd love to bring on board. There's additional luxury brands that I think are missing, um, and just ones that we haven't had time to get to yet. Our team is signing up new brands every day. Um, but again, we're sort of starting with this initial target audience. I think men shopping on the platform will notice there are fewer options when it comes to men's than there are in women's, because we started with women as our target audience, but we're continuing to build out the men's side of the business as well. Um, we're just sort of keeping pace with who our customer is, um, and who's doing the majority of the shopping.

Speaker A: Can you dig in a little bit more about who your customer is and how you kind of focus your product around them?

Speaker B: Yeah. So we're currently targeting the millennial woman who, um, spends money on shopping and, um, who, you know, cares about branded fashion, um, who has a fashion sensibility and is, I would say, a fashion enthusiast. Isn't necessarily like the fashionista. You know, she's not the one who's sitting front row at Fashion Week, but she's following along. She's curious what's happening. Um, she tends to have some brands in mind that she loves, but she's sort of open to discovery and wants to. To find new brands. I think a really big, um, advantage to shopping on Daydream is that you can. There's a level of trust and fashion authority in what we've put out there. And so it's a great way to discover new brands. A lot of women know certain brands that they love and make them feel cool and fashion forward and chic. But we're sort of able to help them understand that because they like those brands, there could be additional ones that make a lot of sense for them. Um, brand discovery is really big for us. Julie and I both, um, are longtime fashion lovers and really feel like if we are building a platform that helps emerging designers be discovered and find new customers, then we're doing a service to both the customers and to the industry. And so we're really interested in continuing to help, like, help the fashion industry really flourish and grow when you look

Speaker A: at, like, bringing on customers and getting people excited. Because, again, like, we've kind of been touching upon all products in this space are so story driven. They're so, they're so, they're so heavily crafted. How do you, how do you bring on new customers? How do you get people excited about tying Daydream? How's that going in your first three years of resistance?

Speaker B: So we, we haven't really um, gone after that in a big way just yet. We've been very reliant on um, PR and word of mouth and some organic social. So we haven't quite gone after customer acquisition yet. Um, like I said, we're sort of spending a lot of time seeing how customers are shopping, how they're using our platform. Um, and you know, we're exploring different partnerships with um, substackers and different influencers. Um, you know, we have some ideas around how we might want to work with a network of stylists to sort of roll out an ambassador program. Um, so there's different things that we are working on. It's obviously a very important thing for our business of how we're going to get customers. But we're trying to be careful before we sort of embark on that mission to make sure that the product we have is the product we want to really be driving new customers too, in a big way. Um, it's funny though, you touched on something when you were crafting that question that I wanted to go back to, which is that shopping for fashion is highly emotional and it is very nuanced. And so um, one of the things that we look at all the time is how does shopping on Daydream stack up to shopping on Google gemini or on ChatGPT for example? And that's where like, that's where this becomes like, so fun. This is like where the rubber hits the road, which is that there's an underlying technology that a lot of people can access. And I think there's been lots written very recently around just the proliferation of AI, how much it has matured in the last three weeks, even um, with all of these new models out. And I think what's, what's so interesting is that this um, level of taste and this need to understand emotion and the nuances of fashion is where these sort of this like vertical play of wanting uh, to go some, to access a technology that understands that uh, in order to really shop, get back that joy of fashion, feel the emotion around what you're shopping for. And what we've built is this underlying fashion knowledge graph that, that essentially translates um, the, the brand vocabulary into a shopper vocabulary. So that if a brand inputs that this is a silk bias cut gown and a shopper says, I need something elegant to wear to a wedding. We actually are like, become that like translation layer. And we can do that because we are so focused in fashion so specifically. So it's not just about like, you know, getting all of this information into one place, but it's about understanding the different nuances that go into the verticalization of fashion.

Speaker A: The knowledge vein is really important. You know, this is, this is a conversation in AI a lot about um, the importance of specific like industry knowledge and the edge that gives you. Because, uh, there's a big fear that I, uh, think it's taught mostly about writing right now, but I can see it in the world of fashion too. But this homogenization of culture with writing, this idea that we're already all starting to sound eerily similar because we're all using the same tools and all using the same large language M models to write. And it's making us sound more homogenous and making us sound using the same type of grammar, the same type of word structure. Is there a fear about that with fashion, um, that AI is going to push people towards kind of the same culture? Or is that just kind of an overblown anxiety? Because that was the fear of social media as well, right? That we all just going to become the same person.

Speaker B: Yeah, I mean, it's funny. I don't think so. I actually think, um, a lot of this technology should enable people to take more risks and, and discover more brands. Um, I think about it a lot. I'm based in New York and I ride the subway every day. And you sort of look around and you think like everyone has a finite, finite number of brands to shop from and a finite list of stores to go to. But you look around and there are no two people who look the same. And that's kind of the magic of fashion, right? Is that like how you put something together, how you style, it really becomes like sort of so uniquely used. And there's a danger in people not knowing how to do that. But I think that's where like AI comes into play and it can kind of help give you the um, like, give you a sense of like, authority and feel like, you know, it's sort of like it emboldens people to take some chances and like figure out if they can do something and helps them discover rather than continuing to like, to know, like, oh, I know that Vince fits me really well, so I'm just gonna buy more Vince. It's like, well, if you love Vince, like, how about you try some of these other brands that you might not have heard of but um, cut things similarly or you know, have a similar vibe and then you start to like really branch out from there. So I think it sort of actually helps stop this like shopping from your own closet, which is just buying more of the same and kind of can help you branch out and buy more new, newer, different things.

Speaker A: Yeah, uh, no, I, I love that. I love the shopping from your own closet phrase, I think because there's, there's a lot of fear in this industry. Right. A lot of people are afraid of taking risks. A lot of people see like when they think of fashion, they don't think of um, they sometimes can be seen as like kind of above them or, or like, like elite almost. I, I interviewed a wine expert, uh, a while back on my other show, the Linen Suit and Passatai, where she talked about one of the issues with the wine industry is that it's seen as elite and people don't want to, uh, almost afraid to dig in. So they just kind of go with the simplest stuff because um, it shuts a lot of people out. But I love what you're saying about this. Using AI. Using some of these tools to discover more in kind of a safer environment without having to like. Because some of these stores can be intimidating. Like I have, um, my mother and both my sisters are very fashion forward people. And I have spent a lot of times in chairs at Nordstrom and Bloomingdale's. I know which ones have the best wi fi. It's great. But a lot of these stores can be very intimidating. So I love this idea of like using bots like this to allow you to explore your interests. Because fashion is for everyone.

Speaker B: Yeah, no, absolutely. And uh, you know, and I think like, I think that's the idea here. And fashion doesn't just have to be a luxury brand. Fashion, like what the beauty that and the slight difference I think with wine versus fashion is fashion is a bit of a necessity. At least apparel is right. Like you kind of, if you're gonna leave your house, you gotta put on some clothes. Um, and so when you can actually make it something that feels fun and not intimidating, then you get interested in what it is that you're wearing. And I think there's a real power in feeling confident in your clothes and feeling good about what you're wearing and what you're walking out the door in. I mean most people will say they can. They feel a difference in themselves if they like what they're wearing. And so why not sort of like give the power to the people to feel confident in what they're wearing by helping, giving them a platform that's really going to help them, um, like what's really going to sort of help them understand what's good for them.

Speaker A: Yeah, I would love to learn a little bit about what you're learning from these conversations. Like from Seymour, the questions that people are a little bit less intimidated to ask. Because I kind of alluded to this earlier, but like, I've never been more intimidated in my life than at, uh, I think it was Louis Vuitton in Paris. Oh my God, that was terrifying. So, um, tell me a little bit about what are you learning from these conversations that you maybe wouldn't have seen in retail shops or in other shopping experiences?

Speaker B: I mean, the queries are amazing, right? It's like sometimes people start with sort of a typical Google search of just like, you know, a black dress or something like that, but then they like, really, they really start to go out there. So actually was looking for, um, to see actually how some of the men are using daydream. And there's one that's polished loafers that work for the office and for a wedding welcome party. It's like, you know, it's just like sort of like really getting out there and being like it's not just, you know, like, it's not just sort of like one thing or another, but it's actually like you want what you're buying to be like really, you know, multiple players, right? Or we had one that was like brown pants that sharpen any look. Or we had a few searches that like, revolved around this like, shop the old money look where it's like sharp or polished. But you start to see this, like, understanding what people are looking for. There was one really long one where it was. I'm looking to build a full outfit that captures a specific vibe. Futuristic, dystopian, courier think heavy tech wear influence. Almost like a cyberpunk character, but functional for a rainy city night. Um, imagine saying that in Louis Vuitton. Imagine walking in there being like, this is what I need, or Nordstrom or anywhere else. So it's like, it's almost the way that I think when like, you know, people started to realize that you could search for things on Google that you wouldn't necessarily ask your mom or your doctor, it kind of starts to be that same thing. Um, we had one that was like, Valentine's Day is coming up and um, I'm just Getting over a breakup and I want a jacket that makes me look and feel hot. Like just people are just not going to say to the same salesperson when they walk in. And you know, hopefully we're able to like be that comfortable place where people can ask the crazy questions. We do get a lot of questions around body type like um, you know, I'm pear shaped. What's going to accentuate my legs? Like those, those types of questions that again I think can be intimidating to ask in a store or you know, less things that sound overly personal, but more just like, you know, I'm starting a new job and I want to make sure I look on brand or fashion forward or that I fit into the tech environment or different things like that that feel a little bit harder to ask someone in a store.

Speaker A: Um, I did want to ask you a little bit more about something you brought up and previously I grew up in Toronto and I worked in Los Angeles and media in Los Angeles and constantly conversations of how do you stay in touch with society as a whole, especially in a world like fashion when uh, it's so easy to kind of get locked into the coast of like LA and New York. As a chief Brands Officer, how do you stay in touch with fashion as a whole versus just the loudest stuff on the Internet or what the models are spitting out immediately?

Speaker B: Yeah, that's a great question. Um, you know, the brands are the arbiters of style and fashion and so paying really close attention to what it is that our brand partners are putting out there, whether it's like, you know, the, the um, Runway brands that they're putting out, obviously six months before the um, styles come out, or if it's really just like shopping the racks and seeing what's in store. So I pay a lot of attention to that. I do do a fair amount of kind of like comp shopping just walking around to different stores, not just seeing, but not just seeing what they have on the mannequin, but also what's on the sale rack. So what's less interesting, you know, to, to those people, um, I do a lot of reading, a lot of paying attention to like, you know, just different influencers who are out there who represent different, um, people and different, you know, geographies and different just types of dress and all of that. So um, the wonderful thing about the Internet is it is a vast source to get a lot of information from and we just try to pay a lot of attention. And of course like now we're starting to track our customers in terms of just, like, understanding what they're searching for and what they're shopping. Um, and as our customer base grows, we'll be able to use that more and more to help inform trends, um, and what's happening and share back that insight with our brand partners.

Speaker A: Yeah, no, that, that makes a lot of sense. And in a similar vein, for our listeners that are trying to enter the AI space, whatever it mean, main, being a lot of consumer AI, a lot of different things. As a leader in this space, how are you staying on top of it? Because it's fastly changing, New models are being released, uh, new hype stuff are coming out. As someone who's been in the tech industry, in the tech fashion industry for so long, at the cutting edge in almost every stage of your career, how do you stay on top of how technology is changing and how it's affecting your industry?

Speaker B: Um, it's not an easy task. And our CTO said the other day, it's like, we work all week, we take two days off for the weekend, and we come back and everything's changed when we get back. Um, I, you know, in addition to, like, reading and listening to a lot of podcasts, I think it's also about, um, trying. Trying the tools. So don't just use AI like a search engine. Like, need to go beyond that. Find the tools that make sense for your industry. Try different things. Like, you know, I used Claude to build my own app. Just, I don't, you know, that's not what I would do here, but just sort of like, I really wanted to see how it worked, just to, like, kind of get behind it. And I think that it seems intimidating, but again, it's something Claude can help you use cloud. To use cloud. Right. So, and I think that that's the important part is just like, continuing to stay really adaptable, be really flexible, and don't be afraid to try the newest tools and just keep trying and talking. So we do like a weekly brown bag series here where everybody kind of shares new tools that they're using. We give everybody an AI stipend. So everyone on the team, from engineering and marketing to product etcetera, um, gets a stipend to spend on AI, their own tools, whatever it is they think makes the most sense to try out. Then, you know, if they've had success or failures, they share back with the team. So we try to keep, like, there's so many tools out there that we can all try them each individually. So everyone's kind of trying different things, seeing what sticks. If there's something that really works on an enterprise level, then we might, you know, bring it on and tell everybody to use it or suggest that everybody uses it. But I do think on a personal level, particularly, like, you know, if you're getting your MBA and you're studying and whatever, like, it's a really nice. It's a good chance and a good opportunity to just be trying out the latest tools and the latest models. I would say, if you can afford it, pay for it. Like, pay the $20 a month subscription fee. Don't just use the free tools that are out there, because those are older models and, um, they're not as good. And so I think you can't see the power of it. And I do think it's important to kind of sign up and try it all out.

Speaker A: What do you say? What do you think has been the biggest difference about building a business in this kind of AI forward world versus when you did it before?

Speaker B: Well, the first thing is that it's just. It's actually like, it's now much more possible. So, um, the stuff that we had hoped was possible when we were building the. Yes. Um, is just. It's just out there. So it's much. It's definitely. It's all possible. Um, I think there's so much hype around it, um, which opens up the conversation in a way that it didn't before. Um, and I think the pace is just insane. So keeping up with the pace is. It is part. It has become part of my job. Right. It's just like, not feeling like I'm accomplished or experienced enough that I know what's happening or what's next, but. But really just sort of like this stuff is happening rapidly and you kind of never know what the next announcement's gonna be, when the next release is gonna be. And so, um, I would say that probably the pace of innovation is the biggest difference that I've experienced in the last 20 years.

Speaker A: And how do you stay disciplined then? Like, if anyone in your company can come with something super exciting and a great switch or new models are dropping every day, and how do you stay disciplined with what you're doing?

Speaker B: Well, I think, you know, we have a plan and we have a North Star that we're building towards, but it is important to listen. I think ideas come from everywhere. So we have an incredible leadership team with a lot of experience. We also have amazing people at every level who are all coming with important ideas and so creating a forum that everyone is contributing. Um, but, you know, again, making sure that anything that we end up prioritizing is in the name of getting us to this. Like building out a personal shopper in your pocket and just getting us closer and closer to that goal.

Speaker A: Do you have any advice for people in business school in their first jobs looking at, like, you know, AI is on the rise. I'm really excited about this industry. Is now the time for me to risk it all and start something new?

Speaker B: Um, it's funny, I. I was talking to a friend who works in children's book publishing. I'm gonna get to the answer, but there's. There's a reason for this. And she said, everybody has ideas, but it's how they write it that actually matters. So, like, we all have an idea of, you know, Judy, go shopping, and this is what my new book is gonna be about. But actually, like, how you go about writing it and crafting it is more important than what your idea is. And so I think that what's important to realize is we're all witnessing it this, and we all have great ideas. If you have the conviction and you really have the execution and you have a way you're going to get it done, then I think it's worth pitching and seeing if, you know, if you are that person who can write it too. I also think, like I said, paying attention, using all the tools, continuing to try it out, is kind of the progression and the way to make sure that you're staying involved and you're getting there. So it's hard to say when is the right time to take the risk. Yeah, um, it's always the right time, and it's probably also always the wrong time. Um, and so, you know, I think the power of conviction and the level of execution become what's most important. But the best thing that anybody can do right now is to keep. Is just like, you know, stay up to date and keep trying the tools. Like, don't just read the articles, don't just refer to, to the podcast, but actually go in there, download it, try it out, um, and like, you know, watch what's going on and be a part of it.

Speaker A: Was there a moment for you, um, for starting daydreaming? Ah, Was, uh, there a moment where you're like, I have to do this. This is. I'm being called towards this?

Speaker B: Well, when we were building the yes, it was like, this is the best place to shop. And as a consumer and, uh, sort of, you know, someone who really loves the fashion industry, we really need this. And when Pinterest acquired the yes it was a great opportunity. We thought all sorts of stuff was going to happen. They ended up taking a different path, still using a lot of the technology, but not building out in the same way that we would have. And, and then ChatGPT was released and you started to see like, wow, this is the tech that we wanted. Oh, and by the way, I don't have anywhere to shop anymore, so we better get to work. And this is like, you know, we are on the cusp of something great and um, we better go build this because I need this, my friends need this and I think the industry needs it. And so I think it was really like kind of putting pen to paper and like starting to use ChatGPT and seeing the power of the technology at work and then really understanding like what it could do to drive the fashion industry forward. Felt like there actually was just like no doubt in my mind that we had to build this.

Speaker A: Kind of looking at the whole arc of your career going to the earliest days, did you ever imagine there'd be a world where you have like this intersection of fashion and technology? Um, and what, what are you most excited about the future of that intersection?

Speaker B: Um, I don't think I started, I don't think I was very imaginative. I don't actually think I imagined it until it happened, if I'm being totally honest. Um, but I think that what I'm most excited about is that for majority of my career technology has felt really intimidating, um, and sort of like a must have rather than a want to have or to use for fashion. And I'm starting to see a real shift in that and I'm starting to see how technology is going to help with the supply chain. It's going to help ideally help with the environment. There's a lot of environmental implications in the fashion industry and so I'm hopeful that technology can help change that to reduce some of the waste, to reduce some of the inefficiencies of the operations and returns processes. Um, and I think, you know, obviously the discovery piece that is really where, well I'm working in right now, I think there's a, there's a power to that that is going to push the whole industry forward. And I think it's just like in a different way than it has before. Like it's no longer a nice to have, but it's actually uh, it's become quite additive to the business and I think that's really exciting.

Speaker A: Yeah, I think I 100% agree. I think there's so many exciting aspects of technology and passion. But like, we've seen so many really exciting companies come up, like, um, daydreaming for one. Uh, but also Stockx and um, the RealReal and um, so many really interesting companies that have found this marriage. Because discovery is hard. It's hard to discover brands unless they have a lot of money to push it in your face on the store, set the tone. And that's why I love applications like yours, where it's kind of fun. What do you think when you use this discovery mode, when you build daydream? What are the essential tenets of, uh, retail and discovery that needs to be preserved in this new paradigm of shopping?

Speaker B: Well, I think that discovery in fashion was largely a real estate game for, for most of, uh, fashion's life. Right. It was where's your flagships, where's your store? Which malls are you in, what avenues are you on, what stores are you next to or for wholesale brands? Where is your product, what brands is it next to? What are the adjacencies? And now the flip is that the customer is at the center. So now it's not about as a brand as Gucci. I think I need to be next to Bottega. Now it's as a Gucci shopper. I also buy Levi's jeans and so I actually want to see them both. And so I think that it's actually what's become really important is putting the customer at the center, not just trying to push product that a brand thinks they need to sell or a store wants to offload, but helping customers find what really makes the most sense for them. For their body types, for their style, for their lifestyle, et cetera.

Speaker A: Yeah. And what I also love about this, about putting that customer at the center is that this is one of the few AI tools that I would say is really promoting real world experiences. Right. Because it's not about time spent. It's not about pulling someone into the digital world. It's not about destroying retail. It's about creating confidential kind of outfits for the real world. And I love that. I love using technology to getting honestly m people out more.

Speaker B: Yeah, no, exactly. It's, you know, and it is about bringing back this joy of shopping, making it a lot more fun, um, and a lot more efficient and, you know, sort of like getting kind of like clearing the barrier so you can just find what it is that you're looking for and what's right for you.

Speaker A: Was there any like, and this is maybe a little off topic, but what was there any kind of rebound in shopping post Pandemic as live experiences rebounded. Like did people get more excited about putting outfits together again?

Speaker B: Yeah, I mean people weren't getting dressed for a while, so it was really nice when they started getting dressed again. I think at the yes, we saw like a real increase in people kind of wanting to get back, kind of rediscovering their style. We saw, you know, stores saw like a big increase in people going back to their stores. So there was a real um, rebound and that this whole sense of just like people wanted to get out of their houses and um, they wanted to look good while doing it. So we, we launched the yes. Um, on May 20, 2020, which was, you know, smack in the middle of the pandemic. And um, when we first started we didn't sell a single pair of shoes. And by the time we were acquired, actually a footwear brand was our number one, our number one most sold brand. So there was like a real, there was a real shift. So By June of 2022, people were putting on shoes again and going out there.

Speaker A: What were some of the key lessons from the yes that you kind of brought over to Daydream?

Speaker B: Um, you know, I think this concept of personalization at the core was really, um, important for the yes shoppers. It was part of what made it um, a really unique shopping experience. Um, the concept of what brands needed from a larger platform also became really important to us. So uncovering what sort of data and insights was going to help them drive their businesses. Um, so that was very helpful to the partners and something that we felt really strongly about continuing to provide, provide to our partners. Um, so everyone gets like a fairly robust report explaining what we've learned, how customers are using AI, things that will really help drive their business forward and things that they couldn't necessarily uncover on their own sites. Um, but then we also realized that at the yes we had only um, mono brand partners, we didn't have multi brand retailers. And we really found that it was a key, um, shopping behavior to go back to Google and start to compare prices. And so if we only had the buying option of say Ganny available from Shop up, that customers were going to go back to Google. Sorry, if we only had it from ganny.com, they would go back to Google and also see did Shopop have it? And so the more shopping and buying options that we could give the customer, the sort of more important the experience became. And that was really the way to create a holistic shopping experience.

Speaker A: Yeah, and I can see how with the uh, Commercialization of AI, doubling down on that personalization is more powerful than ever, which is allowing us to build more personalized shopping experiences. Um, we're rounding out the end of the conversation. We've been talking about, uh, for a little over an hour. Um, a lot of our listeners are early career professionals, people in MBAs or just starting looking into how do I pivot into tech. When you're building a company, when you're building a culture, especially in this space, what are you looking for in new hires? What are you looking for in early career professionals?

Speaker B: Um, I would say that I tend to hire for talent, not skill. And so, um, and especially now when the skills are sort of constantly changing, um, it's important to understand what people are capable of. Um, I also. An advice that I actually gave recently to a room full of MBAs was that, um, it's important to draw out specifically what you're good at and what you can be helpful with instead of saying, I'm an mba, I can come help you with strategy. So particularly early stage companies, as much as we'd love a whole team of strategists, we don't really have the room or the budgets for it. And so I think it's really understand, really important for people to sort of like, um, be very transparent about where they can be helpful, maybe what past experiences they've had that could help drive the business forward, what they would bring to the table. I think offering an opinion, um, writing a really thoughtful email. It's, you know, like you said, everybody's writing is becoming homogenized. It's pretty easy to tell when, um, you've written a form letter that's going out to everybody or when email, you know, it's not something that you've put some thought behind, but it's helpful, um, when you're doing outreach to know why, like, why, why Daydream? By the way, I don't think Daydream's the only company you want to work at, but why is it on your list of 10, um, why are you spending the time reaching out and like, what can you do for us? Because we're a young company that we think very, very. Um, we think very deeply and very. We're very disciplined about who we hire. So you need to help. Give me a reason why you're somebody that we would consider hiring.

Speaker A: Amazing. No, I love that. I love the. It's the search for authenticity right in this. In the world right now, as it's becoming easier and easier to offload everything and sound good. That search for authenticity. Not, not using these tools, but finding ways to use these tools to make sure that your voice is still coming heard and your passion is still coming heard. And I love what you said, hiring for talent, not skill. Because anything can be learned now, right? Like you can become a coder tomorrow. It's insane, uh, how fast you can learn new skills and how much you can offload to these tools. So hiring for talent, hiring for passion, hiring for that kind of unexplainable human quality is so important.

Speaker B: Yeah, absolutely.

Speaker A: Uh, what are some of the major trends you are following in this space in technology and fashion? What should our listeners be looking out for?

Speaker B: Um, I think, you know, watching what's coming out of the big guys. So, you know, anthropic, Google and OpenAI in particular remain just really interesting. What are they going to do next? What are they doubling down on? I think when it comes to fashion, there's been a lot of sort of small features that are being released in terms of, you know, there's different virtual try on capabilities and you know, there's sort of like different elements that I think start to make shopping more interesting and richer. And so we're paying attention to all those. Of course, agentic shopping or agentic checkout is, you know, uh, a big topic. I think it's fun to see how, um, how AI and technology can sort of take out the mundane tasks from what we do and allow us to move forward with the fun stuff, with the more taste based, emotional piece. So, um, really paying attention to a lot of that, how we can create more efficiency, um, which will allow for more time to enjoy life and the stuff we love to do.

Speaker A: I love it. Yep, creating more efficiency, having more real experiences, buying more clothes. We love it. We're big fans of all that here. Um, before we do the outro and anything, any more parting words of wisdom? Anything you want to say to our audience?

Speaker B: No, I mean this was a very robust chat. It was really great to talk to you. I appreciate all of your questions and thank you for having me on.

Speaker A: Amazing. Yeah, very excited to see where this goes and uh, it seems like such an interesting company. Um, so if you enjoyed this episode, be sure to subscribe, rate and leave a review on Spotify or Apple podcasts. You can also follow us on the official Wharton Tech Club, LinkedIn and Wardentech on Instagram to stay updated on upcoming guests and new episodes. Until next time. Thank you so much for joining us, Lisa. It amazing.

Speaker B: Thank you.