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Lauren Sherman
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Lauren Sherman
Hello and welcome to Fashion People. I'm Lauren Sherman, writer of Puck's Fashion and Beauty Memo Line Sheet. And today with me on the show is Jessie Darris, president of Orchestra. We're talking crisis PR, brand communication in 2026, the DTC revolution and evolution, and so much more. Before we get going, I wanted to remind you that if you like this podcast, you'll definitely love Puck, where I send an email called Line Sheet. If you're a fashion person, you get that reference. It's an original look at what's really going on inside the fashion and beauty industries. Line Sheet is scoopy, analytical and ab fun. Along with me, a subscription to Puck gains you access to an unmatched roster of experts reporting on powerful people and companies in entertainment, media, sports, politics, finance, the art world and much more. If you're interested listeners of Fashion people get a discount. Just go to Puck News fashion people to join Puck or start a free trial. Happy Friday, everyone. Hope you're having a great week. I am gonna try to keep this very, very short because I'm very, very tired. I went to London for two days to see the Schiaparelli exhibit at the Victoria and Albert Museum. I highly recommend it if you want to check it out. It's really, really, really, really, really well done. And you know those things. Fashion exhibits at museums are really tricky. So I thought it was great. I went to this dinner that the company hosted with the museum and it was Daniel Roseberry was there kind of holding court, and it was interesting. Marissa Berenson was there. I got to sit next to Chase Infinity and I totally fangirled and told her how much I loved one battle after another. And it was really fun. Don't worry, I didn't take a selfie with her or anything embarrassing like that. Anyway, I did a big screen story on sort of the business of Schiaparelli, which is honestly much bigger than you probably realize. It was very little in 2020 and has like essentially 16x its size in the time Daniel's been the creative director. So just kind of looking at like the motivation of Diego de la Valle, the guy who controls it. He is also, you know, the owner of, of Todd's, Todd's group. So that was a fun story. And then I also, I did get
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to see a lot of people in London.
Lauren Sherman
If I didn't see you, I'll see you the next trip because I'm going to go there all the time now. It was really nice though, that everyone I had a drink with or a meal with, it was just, it was great. At one meal, I. Kate Moss was there at, at the restaurant and she Looked amazing. And I realized there's not as many street style shots of her anymore. And she really does have, like, the most amazing personal style of anyone in the world. And like any of you who dress like Sienna Miller, you're really dressing like Kate Moss. Never forget it. And then also the one little retailer thing I did was I went to the J.W. anderson store up on Pimlic, I believe on Pimlico Road in the Grosvenor Estates. It's amazing. And if. If you're a fan of Jonathan Anderson's and you want to, like, see inside his brain, but also, like, love homewares and love beautiful sourced vintage jewelry. And there is some clothes too, but it's really gorgeous and really, really nicely done. So I highly recommend it and feel like that needs to be the sort of future of retail. Have fewer stores, but do it like that. Anyway, was a great time. I'm back in Paris and I hope you all have a really nice weekend and I'll talk to you on Tuesday. Jesse Darris, welcome to Fashion People.
Jesse Darris
Thank you very much, Lauren.
Lauren Sherman
It's been a long time coming.
Jesse Darris
I know. Apparently this is my fault, but I still think it's yours. But I'm fine with. With either.
Lauren Sherman
Okay. We're both busy people. What'd you have for breakfast this morning? It's still early where you are, so maybe you haven't eaten.
Jesse Darris
I haven't really eaten. I've had. I'm on my second cup of coffee. And then a buddy of mine started a company. I'm gonna do an ad called Pioneer Pastures. And it's. It's ultra filtered A2 milk. So it's got. It's really good macros, 160 calories, 30 grams of protein.
Lauren Sherman
Is it pasteurized?
Jesse Darris
Yeah, of course it's pasteurized.
Lauren Sherman
I don't know. Ultra filtered. That sounds. That sounds like something that Dan Fromer would be like, stay away.
Jesse Darris
Dan definitely knows about this. It's. If you've heard of Fair Life, fairlife is ultra filtered. What he's doing is combining it with a. I'm not an investor in this business. I'm just really obsessed with it. He's combining it with a 2 milk, which basically is okay for people who have lactose intolerance. And it has much more protein in it. It's good.
Lauren Sherman
Interesting. So, Jesse, you mentioned that you're not an investor in this proteiny milk situation, but you want everyone to buy it. Why don't we start with a bit about who you are and what you do?
Jesse Darris
Yeah. So I. Right Now I have two jobs. My primary, my day to day job is I run. I'm the president of a business called Orchestra and I run that business with my partner Jonathan Rosen. We're about 700 people working in a bunch of different categories, including consumer and technology and public affairs, primarily built around strategic communications, but it's an entire kind of suite of integrated marketing, including crisis public affairs, data strategy, a bunch of other things. I started my career, though I've had like a very circuitous route. I started my career working in public affairs. I worked on political campaigns, the last one being John Kerry's presidential run 21 years ago. I worked for a guy named Ken Sunshine and built his. The crisis business at his firm and then sort of accidentally got involved with Direct Consumer, which was my introduction to consumer brands. I, you know, was very early in helping Ben Lear with Thrillist and eventually got introduced, like not introduced. I was talking to a friend of a friend named Neil Blumenthal about something he was working on at business school and that, that discussion. His, that company became Warby Parker. And so I helped those guys get that business off the ground in. You know, I started talking to Neil about it in 2008. The business launched in 2010 and that, that experience sort of, you know, precipitated the launch of Darius, which was, which was our initial business.
Lauren Sherman
I wish I had my emails from 2008 with Neil and his co founders ignoring them. I've told you this story, right, where we have, we have a mutual. And she was like, can you talk to these people? And I was like, sure. And I just kept blowing them off. And it's very funny now.
Lauren Sherman (continuation or interjection)
You.
Jesse Darris
Yeah, you aren't the only one. I think I even blew them off. Neil tried to hire me like two or three times because I was just sort of helping them informally and I was like, dude, I don't want to work with a buddy. And so he asked like two or three times before I actually said yes because I was just like spending time with them on the side. I would go down and like hang out with them on a Thursday and Friday night and just spend time whiteboarding with them. But like it didn't become formal until he asked like three or four times. So I don't. You're not alone.
Lauren Sherman
Makes me feel a little bit better. Don't take my investment advice. That's the, that's the answer really quickly. And then we'll. We're going to talk about Darris because that's how we met and, and will be sort of the the beginning of the conversation today, but on the John Kerry campaign, I remember this campaign very clearly because I lived abroad during this period. And I remember I had a lot of friends from small European countries, namely Sweden, and they were like, how can you vote for this person, John Kerry? What does he represent? And I explained to them that when you vote in America, you need to vote for the greater good. It's not like you can have nine candidates and your vote. Like, if you vote for one of them, it will really make a difference. You have to vote for. For the person who you think will make the biggest difference in a country where. You know. In a divided country.
Jesse Darris
Yeah.
Lauren Sherman
Was this the way that you, like, they positioned the campaign was, like, better than the alternative? Like, I don't really remember, especially because I was living abroad and acting like I was better than I was.
Jesse Darris
This story starts with Howard Dean, because that was who I worked for in the primaries. And often. I mean, I was 23 at the time. Often your first candidate in the primary is, like, your true belief. Right. Okay. How I like this?
Lauren Sherman
The year that he, like, got pretty far. Did he get pretty far further along? Like in the 2000s? I can't remember.
Jesse Darris
No, this was the year. And it was the year of the Dean scream, when you could, like, lose a race by yelling into the wrong microphone, which is really quaint. And we were in the lead, it looked like, for the entirety of the campaign, and then stumbled in Iowa, and he had that snafu with the microphone. And then basically it was a slow descent through. What I think, if I'm remembering right, was Wisconsin. I was like a nothing on this campaign. I was 23 years old, but I really believed in him and his healthcare message and all these other things. Once that race is over, you then make a decision which, to your point, is more of an X's and O's decision. Do you want to keep working on the campaign? Can you hustle yourself into a job? Nobody knows who you are? And so I ended up getting sent. There were 14 battleground states that year. I got sent to the 14th and smallest one, which was Maine. They were trying to win the second Congressional district up at Bangor. And I spent six months there, got to build a team. Was a really terrible manager, like, brutally bad. But why was I. I mean, yeah, we were better than George W. Bush. That was the argument. And I think the. The kind of original sin of that campaign was it had no reason for being right.
Lauren Sherman
Yeah.
Jesse Darris
You know, for me, I got through that campaign. It was November. It's like one of these weird things where if you win and we went into that like that I remember election day believing at least in my tiny little seat that we were going to win. And you wake up the next day and you're either like going to hopefully get employed and it's going to be some big cool job in Washington D.C. or you're totally unemployed and you're back at square one and you've just turned 24 and you're living on like friends couches. Which is what I was. And I was pretty disillusioned by the race. I mean we got swift boated which was like one of these original kind of things where the President who had not gone to serve in Vietnam called this guy who had won Silver Star and a bunch of other awards a coward, which is kind of fascinating. And it stuck and I just wanted to take a break, which is how I ended up back in the city.
Lauren Sherman
Okay, so fast forward a decade or maybe six years and you had done all this like scary crisis comms for Sunshine Sachs and stressful stuff. How did you end up. You mentioned Warby as I guess that was your. One of your first Daris clients. But how did you end up starting an agency and it being consumer about consumer brands? Because your partner is Lisa Frank who came from La Force and Stevens who I knew from. She worked on Target and a lot of fashion brand. How did you end up thinking, oh, all this experience I have in politics and crisis comms. I'm gonna launch an agency that focuses on consumer brands because there was something very particular happening in the market right now that I feel like you all captured that no one else did.
Jesse Darris
Well that wasn't what it was I want to say when I left so I had a. I had a couple consumer brands at Darus. I knew Warby was going to be our first client. I Talked to probably 25 people with adjacencies to consumer and eventually Neil asked me to talk to Lisa who was not looking for a job. And you know this Lauren, but like she's a very risk averse human being. I still have the meetings on my Gmail calendar but it took me eight meetings once I met her to convince her to come do the job with me. And literally only because Neil like actually said I was a good person did she come and do it. But the original business was sort of two things. So on the one side it was a replication of the work that I had been doing at Sunshine. So we started out doing a bunch of crisis. We still have crisis clients, crisis Only clients. We started out with a little bit of work in pop music, so I was representing Demi Lovato and the Jonas Brothers and a bunch of others. And then we had a bunch of work in nonprofits. I mean, I think our second client was Share Our Strength, which is a large hunger NonProfit out of D.C. the consumer thing started because of Warby, candidly, you know, starting when that business launched in 2010, I was going in every week and sitting with Neil and Dave. And then there was a guy named Patrick Bradbury in that room who had a small kind of independent fashion agency. And there was a creative shop called Partners in Spade in there, and Andy Spade was there, and, oh, my God,
Lauren Sherman
why am I blank Blanking on franchise music? No Fernando music.
Jesse Darris
Fernando. I'm a terrible person. And I'm gonna get. Oh, Anthony Spiruti. And I do want to say Anthony is like, the greatest creative I've ever worked with in my life. No offense to anybody else. And I was watching that room work that Neil and David put together, and, you know, Patrick was handling kind of all of the consumer and fashion press and accessories press. Really specifically, he was helping them build relationships in the industry. You know, Partners in Spade was doing so much of the, like, creative, like, ideation and execution of, like, the random ideas that the guys were coming up with that we were all coming up with. And then my job was sort of threefold. I helped them in the early days kind of shape some of the sort of buy a pair language, you know. But again, a lot of that business was like. Like, grew out of Neil's, like, actual experience. When we were in our 20s, I put in place this thing where we would start to tell all these stories about the founding of their brand as, like, a core thing that everybody takes for granted. And then I was one of that crazy crew just coming up with ideas that, you know. And what Darius was on the consumer side is I was trying to recreate that room. And so I knew that I could help with strategy and corporate social responsibility and corporate comms and the connection to technology. And I needed somebody who spoke consumer and who spoke fashion and not uppercase F fashion, as you know, but lowercase f. And it just took me a while to track down Lisa, but eventually I did. That was the original business.
Lauren Sherman
Yeah. And. And so I know Patrick. A lot of people listening to this podcast will know Patrick. The thing was, at the time, consumer brands, especially ones that were connected to fashion, and Warby Parker is. And then also Everlane was an early client of yours. And this was a new SoR. It was the start of the rise of the DTC brand which we both know existed forever basically and really became a big thing with the rise of specialty retail in the early 80s with the gap and things like that where you have an owned brand and a single brand in a store and it's not just about multi brand retail or department stores but at the time, because a lot of these brands didn't have physical retail, they were digital first. They became like this new class of brand and having this as a startup to have a sort of corporate comms side to things that was pretty rare. And so you all work, you were. There was no one like you, especially in the beginning and. And there was so much attention to. To these brands. Did you. And then, and then you all also would take equity sometimes in the business which I think is. Was not common at fashion PR at least. But like yeah, when did you realize that as you picked up things like glossier or. I know that was a few years later, but when did you realize oh, there is like going to be a whole new genre of brand coming out of venture that. And we are the best position to sort of help usher them through. Because you were never going to do sample trafficking. But like as we both know that basically doesn't exist anymore. So you were sort of early on the fact that like it has to be about strategy.
Jesse Darris
Yeah, I mean so we thought. I thought the foundational change that was happening was that a bunch of brands were going to get created that were having conversations with consumers as opposed to at them. That brand would no longer be this thing that you like shouted at people and like they had to listen. It was meant to be communicative. And what was fascinating being like in the very early Warby thing is that a lot of the businesses I saw in the year after that business launched and it immediately connected with consumers. Like people launched like replica eyeglass businesses which was fascinating to me and up to and including. I remember one of them. I'm forgetting the name of it actually. Never mind. I know the name of. But I won't say it out loud. And they actually stole the photography off the Warby website. Which was only really funny because the photography was like partially of everybody's friends. Like because we didn't have money, there was no money for like models. And so what I saw was like, oh man, this is going to hit every single industry like in the entire world. Because what's happening is that the channels that people communicate through are changing. And comms was one of them. But social, obviously, pretty early on, was also clearly going to be one of them. And the conversation was going to be had with people and we were going to respect people and tell them the truth. Like, that was the, like, original grain. And each of the businesses, it's sort of like they were connected linearly. So in, you know, the fall of 2012, Jeff Rader reached out to me because he was starting to put together what became Harry's. And so I helped Jeff and Andy with Harry's very early, and that was where my first office was. Jeff introduced me to Michael Prisman, who was in the early days at Everlane, and I helped Michael with radical transparency. You know, Michael introduced me to Yael Aflalo when Raf was starting to turn from a physical kind of retail store consignment, secondhand, like, into what it became. And so we got to work really early on that. And then I helped Josh Kushner really early with what became Oscar Health Insurance, which is a whole other story and a different thing. And Josh was going to lead the first round of financing into what became Glossier. And that's how he met Emily and originally Henry. And so, like, the businesses were pretty linear and they were all following not the same playbook, but they were understanding the kind of world as it had changed, which is that there needs to be some reason that you exist that you can talk about, right? And, like, yes, the brand has to have great product and it has to have compelling visual language, but it also has to have substance and substance that you can talk about both, like, through the lens of the product that the company's created and through, like, why it exists in the first place. And you could see customers, like, picking up this notion that, wow, oh, this is like a breath of fresh air. It's weird that a brand is going to talk to me like a human being as opposed to, like a customer.
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Lauren Sherman
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Lauren Sherman
Early on was the. I think a lot of what we ended up talking about with DTC is how you marketed to consumers. So like I feel like I've had this conversation with Neil or Con or journalists have millions of times where when they first started marketing on Facebook, like it didn't cost any money or it cost very little money and then it just got too expensive. And can you. I don't know how long this would take, but like walk us through this sort of evolution of these brands because a lot of them, Michael famously would say we're never gonna have stores, which obviously they were going to. But he was like, we're never gonna have stores well into the 2010s and then suddenly they had stores. Because you have to have, you know, a multi channel approach to these things obviously.
Jesse Darris
Yes.
Lauren Sherman
But like what was the sort of how they reached consumers in the beginning and how did that evolve over 15 years or 10, 12 years?
Jesse Darris
If you look at the providence of Warby. And a lot of this was Patrick at the beginning and you know this, but we hired Lena out of Patrick's office and she was like the fourth person we hired. She's now the president of the business. And a lot of it was earned right. And a lot of it was press. A lot of the early Warby stuff was GQ and other things. Facebook was taking hold, but it was still starting to grow outside of the original kind of core college audience. I'll give Michael Prisman credit for this because we've talked about it. A bunch pre indexed, pre ad. Instagram was the other thing. A bunch of these businesses started to find content market fit in the days when Instagram didn't cost anything. And I think that goes a lot for Glossier and Everlane and a bunch of the other businesses. When that thing got indexed and people started to spend money against it. We went through this like almost third epoch where a bunch of growth venture firms decided these were venture businesses, which is a whole different discussion, but like maybe worthy and poured enormous amounts of cash into it. And that cash people just like lit on fire on these social networks and they stopped worrying about like the math of, you know, the way their business worked and the way their gross margin worked and how much it cost to acquire a customer and the lifetime value of that customer. And when the money spigot got turned off, a lot of that stuff went away. But that was also the moment when we went from kind of having this like friend graph approach to social to what we have now, which is the sort of TikTok ification of everything and best content wins. And what's been true throughout is you can spend money, right? Anybody can spend money and grow. But if you don't find like the fit between your content and your customer, you're gonna fail eventually because it's not sustainable to buy every single customer at a loss. Obviously.
Lauren Sherman
Yeah, I feel like the reductive way to put what happened during that period was that like these, a lot of these venture firms thought that consumer was hot, thought these brands seem really cool and they were growing fast and they put a bunch of money into them and they were like, don't worry about making a profit, just like grow, grow, grow as if you were a tech platform or something.
Jesse Darris
Yes.
Lauren Sherman
And in the end like that's not how consumer brands are built and most of them failed. Just talking to founders who like had so much pressure to just grow the top line, do you think that there is any nuance to that or do you think that's just like kind of plain and simple what happened?
Jesse Darris
I mean, listen, to the extent like people prioritized growth over like having real businesses 100% like, I mean there's just no question about it. And I think to the extent you were running a business that had good fundamentals and you could pull it back and make the math problem work and the business still was a real business, you survived. And when you couldn't, when, when you know, the Ferris wheel stopped, like that was that. And so I think, but we had a 10, I mean, you know this, we had a 10 year period where when interest rates were near zero, money was free. And to your point like I, I don't necessarily think consumer isn't venture. Right. But it like, and in venture like, and I think this is like the important point, everybody's like, oh man, DTC didn't work. I'm like, it sure did. I mean, you know, but in Venture, 99% of the stuff doesn't work. So you'd have a hard time explaining to me that skims isn't a venture business.
Lauren Sherman
Sure, yeah. I mean I think the other thing is these brands, a lot of them still exist. So even like outdoor voices, which, I mean how long that will last at this point, I don't know, but, like, it still exists. So I guess, like, why do you think so many of them have stuck around? Do you think it's that because most of them, like, their original investors, aren't even in it anymore? Do you think it's because the brands that were built early on were just so solid from a architecture perspective? Yeah.
Jesse Darris
They all have different stories. Right. And many of them have succeeded, but a lot of those businesses existed before the paid epic. Right. And so, like, say whatever you want about what Ty has built, but Ty is an incredible merchandiser and a great storyteller. She, I think, led an entire era in that category, whether or not she won it. And what she did was incredible. So I'm not surprised that business is still around. Right. You know, I'm not either.
Lauren Sherman
Yes.
Jesse Darris
Yeah, I agree in the same way that a lot of those businesses, like, they were there for a reason and they had built, like, really real relationships with their customers. And so whether or not the business was ever going to be, because you could make an argument that in the world that we live in and the way Discovery happens, that it's going to be extraordinarily hard to create another Abercrombie. Right. And I read your piece. You know, I don't know when this is going to air, but you wrote about it, I think, yesterday.
Lauren Sherman
Sarah Shapiro. Yeah.
Jesse Darris
Yeah. And, like, I was thinking about. I was putting, like, the analyst hat on because I read a lot of retail analysis, and it's like, if you start your year at zero every year and you do $3 billion of revenue, like, you're a successful business.
Lauren Sherman
Yes.
Jesse Darris
Like, and I think it's going to be really hard to build that kind of business in the epic that we have now. But I'm not surprised that a bunch of these businesses have succeeded to some extent. They had real connections with people.
Lauren Sherman
So another thing. Let's talk about the storytelling element of it for. For a second. Because I was working a business of fashion when most of these companies came up. And when you all. I started there in 2013. So it was like, as you were growing, Daris, I was looking at these businesses. And so I worked on a lot of stories with you and your team. And the thing that happened during that period was this, like, very close coverage of these firms. A lot of sharing of revenue when they were going out to raise another funding round. Like, a lot of transparency, as ever, as Michael Prisman would say, in terms of, like, what was actually happening at the business, because they were proud of it. And there were strategic reasons. But what it has done, and I see this in my coverage of the luxury industry too, and I'm sure this is across industries, is that there is this, like, micro coverage of businesses. And also, like now, now you see it on TikTok and you see it with. When I'm covering LVMH, like, there are consumers who shop Dior who are doing TikTok videos about, like, is Dior going to save LVMH? Like, it's so step by step now. But how did that benefit the brands that you were covering? And also, like, how did it challenge them? Because Outdoor Voices is a great example. I'm probably the most. The biggest student of Outdoor Voices and the person who's followed it as closely through all the different iterations. But there were other people too. Like, there were New York Times. Think about the fact that they were like, there was a New York Times story about this little company that, like, at most made 90 million a year in sales. Probably not that much. What do you think, like, the benefits of it were? Or the, you know, what were the challenges with people covering stuff so closely?
Jesse Darris
I can tell you why I thought it would work at the beginning because it's. It's definitely changed, right? But like, I grew up. I'm an 80s kid. I grew up in a mall, right, Pretty much every week. And it feels like the heyday of, like, brand advertising, like, the Gillette ads were incredible. Like the be like Mike ads, all that stuff. You walked into a mall on the weekends and it was sort of the, like, original social network. You walked around the mall with your friends. Like, the windows were what was important, all the merchandising. You walked in, like, you know, you. You maybe saw stuff, merchandise on a table. You maybe pick something up. Like, the third or fourth or fifth thing was touching the product, but it was all imagery and, and merchandising, right? And so I, I do think the thing that we had all gotten a little allergic to was being sold at, right? Because it felt like we were being sold at in like, the most materialistic country during the most material in its history. And I think the organic nature of these businesses when they started and to an extent now where people would just be honest with you, right? I remember like, like long conversations. Like, I think the day after we launched Harry's, the company, not the day after. Maybe it was a few days later we had a problem with the product. And I remember talking to Jeff Rader, who. Incredible founder, right? Warby and Harry's. And he Was like, what should we do? Right? Because it was. People were saying the product was. It was. Was not working the way they wanted. And literally the conversation we had, well, what would like, the incumbents do? And we talked that out and then we did the opposite. And I really do think a lot of it was that it was filling a white space where people felt like the brands they were interacting with were. Were kind of not phony, but like, felt like brands they didn't feel like people. Right? And so that was the beginning of it. It then starts to scale and everybody's talking like this, right? And we go through this period of time where everything looks exactly the same, which always happens. Everybody speaks exactly the same, everything is derivative. And then it starts to feel less special, right? It starts to feel like everything's been carbon copied. And that period of time is sort of when you figure out whether or not you actually have a connection with your customer and with. With the ecosystem. So I do think, and we've gone through several periods since then, but I, I do. Like, that was the original intent of it, if that makes sense.
Lauren Sherman
Yeah, that makes sense. And. But it would. Like, when it got a little dicey later on, like, how did you manage it? If for. And all your brands, it was different. Like, I would say for most of Reformation's trajectory, there was a, business wise, it always did well, and B, there was like one blip during the pandemic where you had like a. A thing that a lot of people were dealing with at that time, like reckoning type thing. But it was actually when. When you look back on it, it was like two days. Yeah, like it was. But then there were other businesses that you worked with that would like, have weird. Like Everlane never had, like, would have like, weird controversies, but they were sort of also surface. But it would come up, you know, once every six months or once every year. Like, how did you. As those. It was like. And you had all the big brands, so all the ones that people cared about were the ones that had challenges. Like, why do you think it got a little dicey for some of them? I mean, obviously Warby never. Never anything controversial, but, like, there was stuff. Do you think?
Jesse Darris
I just think it's part of the natural cycle.
Lauren Sherman
Yeah.
Jesse Darris
Like, every single brand goes through peaks and troughs. Like, I. This is why, like, I probably bring this up and I hope I don't get in trouble, but, like, you know, there are brands. I won't say the name because I don't want to get in trouble, but the enormous Consumer brands, consumer lifestyle brands that got in trouble for child labor in the 90s. Right. Like, literally have your kids make their products and lots of them. And those brands are all still around and all bigger than they ever have been before. Like, brands go through challenges. Right. And so, I mean, Reformation's an amazing example. Like, Yael founded that business and has an incredible eye and an incredible voice. But, like, that business isn't what it is now without Hallie, who is an insanely talented operator.
Lauren Sherman
Yeah.
Jesse Darris
And what she's done to the business as it's grown, I mean, it's just incredible to watch. But they have since the beginning, no matter what they've gone through, like, stay really true to their product and to serving their customer and to, like, making stuff that people love. And they also exist for, like, a great purpose and a reason. Right. To make the world a little bit better. And so I. I don't know. I see, like, I think it's normal what every single one of these brands went through. They were hyper scrutinized because they were covered a lot. And, like, you know this. But, like, the media echo chamber is a thing. Like, people love to write about the things they've written about. And so if you've written about the rise of a company, you have to write about its downfall, and then eventually you have to write about its resurrection. Right. So it's like, to me, that's just the cycle of, like, of the way, like, the public personifies stuff.
Lauren Sherman
Well, I think that's why you all are a bit different than for the PRs or for the fashion people who are listening to this. That's why you're different from a strategy and an approach perspective. Because in fashion, a lot of these companies, when they're having problems, are just used to journalists ignoring them because they need the advertising too much. So they'll skip over if a company is having a lot of financial issues. The one exception to that is, like, if it's on the public market, then it's fair game. So I feel like a lot of these trade reporters in particular get very gleeful when a big company has, like, a very bad quarter because they're like, yes, we can finally write the truth about what's happening with it because it's public information instead of doing their jobs and writing about it behind the scenes. But that's my own little. My own little soapbox. But.
Jesse Darris
But to your point.
Lauren Sherman
Yeah.
Jesse Darris
And which I think is fascinating is, like, a lot of this has gotten democratized. Right. So you're not seeing you don't have to wait for an established media presence to write about something, to have, you know, some analyst, you know, whether you consider them armchair or not. Kind of like doing thing pieces on it, right? Like the idea, like, even what you're doing, I mean, just like the idea of what you're doing existing 10 years ago, like, it's so obvious now that it should exist, but it wasn't necessarily obvious when you were at BoF, right? So, like, yeah, I, I just think. And again, as we've totally democratized distribution, right, it's totally free to distribute now. Like, I, I have the same distribution cost as Puck does, right? Whether or not anybody's reading it is a different matter. But like, as we've totally democratized distribution, as, as we made it easier and easier to discover new stuff, whether it's new people, new brands or anything, like, you've just totally flattened the earth as it relates to, like, how many people can opine about how many different things. That's what you're seeing. So, like, to me, to overreact to any one thing, when a brand is going through ups and going through downs, you know, brand is built on years and then decades of repetition, like, and you're either good or you're not good. And I think the only time when brands truly suffer, when their businesses actually suffer, is when the stuff that is not good becomes like, a working pattern. But aside from that, like, going through like a single, like, negative event, I don't think is like, particularly impactful on a real brand.
Lauren Sherman
Do you feel like these brands are in the brands that you're working with, that, that have been around for 15 years? What kind of phase of the cycle do you. Of the consumer cycle do you see them in? And how do you all. How are you all working with them differently now than you were even five years ago?
Jesse Darris
I mean, the world fundamentally changed, right? And so I would say three things in particular to me. One, audience is everywhere and all around us, right? It's. You're a large company, a small company. Your internal audience matters, right? Your customers matter, influencers and creators matter. The press matters. That's one. Two, the kind of distribution of power has changed. And so power exists in lots of different places that are formal or informal. You can talk about the government, both federal and state governments, but you can also talk about power existing in small pockets of the press and in influencers and getting caught in a political debate that you've never intended. And then three, everything's moving really quickly. And so the best brands are Collapsing the delta between the advice, their CEO and their CMO and their CCO gets the strategy that they have put in place and then their ability to react whether you're doing something proactive or reactive. So I say all that to say everything needs to be more integrated now, right? And we have this fundamental belief here that the future of the world is earned, that every single channel that's meaningful now is meaningful because it earns your attention, right? It earns your time, it earns your scrolling. Like it earns your ability to show up in person, by the way, reflection of what you guys have built and others in that space have built that are successful. And you know, for us, like you have to have the ability in a company like ours, I believe, to be able to speak to the C Suite 1, 2, to be able to build like data informed strategy that actually like speaks to your customer and allows your customer to speak back. And then three, has the ability to work like totally multi channel, like regardless of channel, in whatever way works for your client. So that might be press, it might be influencer, it might be affiliate, but it might as much be, you know, organic social or public affairs or crisis or internal communications. And the more diffused those various things are, the harder your life is going to be as a leader.
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Lauren Sherman
How do you think the way that consumers consume now being so. I don't even know how to Describe it. It's like so micro in terms of the direct relationship with the brands, but also you just have so much access to so many different brands and how you discover things has changed. Like it's not, it's not about like going to a store anymore as much as we would love it to be. It's not about going to a store and you find a new brand and great and what a lovely experience. Like people just don't. It's not how their brains are wired anymore. How is that changing how these companies are, are growing and, and being built?
Jesse Darris
Well, I think the way discovery works, especially in fashion today or in retail more broadly, the way discovery works and the desire of people to discover makes it harder to build something scale. Right full stop. I think we all know that and it's driving people into like smaller and smaller corners. And I think two things can be true. So one, like people still love that act of discovery. But I also think like, paradoxically we're going through a bit of an age where people want to buy less stuff and have it be higher quality in some respects. It's still young people are still going to buy fast fashion. I know that. And I think when you look at those two things, I still do think people shop in similar ways that they have in the past where if they find something they like, they invest in it. Right. And so yeah, at the same time, like, and I think the way discovery is happening in a world like consumer is different than the way it's happening in other places. Like we talked about this briefly. But when people are searching on ChatGPT or Claude like it's a totally different thing. So if you're searching for like the best tent for a desert for instance, you used to put that in Google. You'd have to, you know, shuffle through the 10 sponsored links and then start to do your own research. You do the Same search in ChatGPT now and it's going to tell you the tent to buy. Yeah, and it totally changes the intent and it totally changes the conversion. And if you click the sourcing on that ChatGPT work, it's going to bring up probably 10 things that are either based in customer comments or press effectively, which I think is fascinating. It's almost like going back to the beginning where something as simple as just doing straight up paid is going to change in value relative to things that help establish and build brand. So I do think we might be at the beginning of a new epoch.
Lauren Sherman
Well, this might be a dumb question but like how much are brands able to pay these ChatGPT or Claude or is that not part of the equation right now? I assume it is with Google AI.
Jesse Darris
I mean people are building AEO products. We have a really good one, right. You know, and those, you know, there's, there's kind of three pieces to it. One, the, the models are picking up like certain types of earned content. And so if you understand what they're picking up and you know, that gets to the last part which I'll talk to, you can reinforce what they're picking up and do more of it. That's one to. A lot of SEO work was about like the functional like setup of a site and the way the way your own content works and a bunch of other things. And so like we have a team that can actually work on that because there are things that the alums are picking up. And then three, you have the ability to continually measure this, right? To like literally run the same query millions and millions of times and see how it's changing from day to day and why it's changing. And that data can drive the decisions that you're making on one and two, if that makes sense. And so listen, ChatGPT, I mean OpenAI and a bunch of these companies are starting to move towards paid and that ad thing is going to happen and I think that will change over time and adapt as they see what works. But already right now, the version of how you impact these engines, plenty of people are starting to do that and if you're not, you have to be.
Lauren Sherman
Yeah, well, I just wonder. The thing I use it a lot for is like what book should I read next or what movie should I watch next? And I do, the first couple times you use it, it's really valuable because you're like, oh, that's exactly what I want. And then you realize it's only gonna, it keeps coming up with the same things because I'm a limited person. So no matter how I really put it in, I'm kind of saying the same thing every time. And so there's books that have been surfaced to me on Claude like 15 times and I'm like, why does it. And so I wonder, I mean, I guess this is just what. Our world is just so small now and that's what it reflects. It's so big but so small.
Jesse Darris
The LLMs are going to take in and reflect the conversations you have with it and get to know you. Right? And that's one which may or may not sound creepy, right? And then, yeah, number two, I think the most Interesting thing to think about technology is today is the worst it's going to be.
Lauren Sherman
Yeah. What do you mean by that?
Jesse Darris
Like, the experience you're having today is the very worst version of it you're going to have. The one you're going to have tomorrow is going to be slightly better and slightly better and slightly better because it's going to continue to improve the experience. Yeah, yeah. And so, yeah, as it learns more about you as the kind of, as the product matures, it's going to get better and better at this. Right. And you're probably, since you've realized that like it works on books and movies, you might ask it for some other stuff down the road. Like, and you're not going to do it for like the clothes you buy because you're encyclopedic about that, but you're not encyclopedic about everything. Right.
Lauren Sherman
Well, I have used it for like, what should I, what kind of outfit should I wear tonight?
Jesse Darris
Yeah.
Lauren Sherman
So like, I'm not going to ask you for advice on what to buy in that, like, what brand to buy or anything like that. But I have been like, it's this weather outside and I'm going here at this, in this place. What kind of, what's like a. Because sometimes you just don't know. Like you, especially in la, it's like people dress like freaks. Like, no one, nothing ever makes sense. I'm always like, should I wear that? I have, I don't know.
Jesse Darris
Think about what you're saying. Like you, Lauren Sherman, right. The most like, knowledgeable person about this in like, I know you won't say you are. You spend your entire life writing about, about what people are wearing about like how these brands grow and you are asking for advice in that category. Do this thing. So I just, I think any of us trying to anticipate exactly how this is going to change the world, it's, it's sort of futile. But I think you play it inning by inning and right now it's at this place product wise where you can definitely impact it by doing like smart things and doing it repetitively. That will move into the paid realm like everything else. Like once paid starts to pick up and it'll be fascinating to see the paths the different products take and then there's going to be a million other like, versions of that. But if it's not like it has to be part of how you're thinking, because I like, Discovery is going to continue to change and in the same way that where you and I Grew up as like AIM kids, right, Doing dial up Internet. We could have never anticipated the impact, the 20 year impact Google's had and Google search and obviously this Both like the OpenAI version and the Claude version and the Google version is going to have, it's an apocalypse impact in how we're going to behave as consumers.
Lauren Sherman
Okay, final question for you. What do you think? And this, it's a hard question to answer but like what do you think the value of brand is now and will be as, as this stuff develops? Because you can say the thing I see with sort of generational surveys that I've been looking at for 20 years is half of the surveys say that consumers, young consumers don't care about brands and aren't brand loyal. Half of them say that they. And it seems like every generation's the exact same thing. But I'm curious, like, do you think there is a value in spending a lot of time and money in building out a brand story and a brand's reason to exist when there are just people buying these hair curling irons on TikTok because TikTok said to do it?
Jesse Darris
Yeah. Yes. And so like I think brand is always going to have enormous intrinsic value and generational value. Like brands are things you can pass down to your kids. And I also think people shop with their wallets and their emotions, right? And so discovery is both going to be a thing that we're actively doing in finding new things. Whether those things are finding us through all the social media advertising or we are scrolling with intent and trying to look for something. One, two. We will still also pretty much always go back to the brands that like deeply connect with us and those brands exist all over our lives. Right? You might feel that way about Nike, but like, like we feel that way about Colgate, right? Like, like if I brought up Crest to my wife, oh my God, like no way. And so there's no way that is going away and if anything in the world to come where we're doing less of the legwork on discovery when we're counting on these answer engines to tell us what to buy. I could make a pretty compelling case the brand's going to matter more because you're going to have to have heard of something to feel trust in buying it if it's going to be sent to you in a way in which, oh, this is the choice because if you see it and they're like, this is the one you should buy, if you've heard of it, you're almost certainly going to pull the trigger and buy it. And if you haven't, it's probably going to lead you to do a bunch more research and like, figure out, like, what the proxy for trust is for the purchase.
Lauren Sherman
Yeah, I mean, it's. Of course you brought up Nike because I think it is the brand that is the most, like, at an impasse right now where it seems like it's doing a little better. It was never doing that badly. But in the market, the perception was that it like, lost whatever it had. And for our generation, it is the, like, go to brand. I don't. I have actually never been a big Nike sneakers person. I've gone in and out. But like, right now, if I buy workout clothes, I still buy them from Nike because it's just. And I love the. I love the logo. Like, I love the way. I love old vintage Nike stuff. I don't know, like, do younger consumers feel this way about Nike or Levi's or Kleenex or Crest? Because the marketing isn't as effective. Even if the marketing is good, it's not as, like, emotional as it was when we were growing up because there's just so much more. It's just such. It. There's so much more exposed to so many different things that, like, I don't. Do you think there are gonna be brands that come out of this generation that people feel, a, do you think that Nike is gonna be as valuable or powerful as it is now 50 years from now? And B, do you think there are going to be brands that develop during this time that you help develop that are going to be super powerful 50 years from now?
Jesse Darris
The answer is I don't know. And I hope. I mean, I was just looking up Nike's numbers. Nike did $46 billion of revenue, 10% increase year over year at that size. I mean, that's incredible. That means it grew $4 billion last year.
Lauren Sherman
Well, I think it had at. Had fallen quite a bit. So.
Jesse Darris
Yeah, well, sure. They, like, they clearly pursued a distribution path that wasn't like, super smart under previous leadership. They've also clearly gotten back to like, product LED delivery now. And I think the product looks. I mean, I love Nike. Nike is. But what Nike. Nike's, everybody. When I ask Nike what the mission is, they say just do it. It's not the mission. Right. The mission of Nike is inspiration and innovation to every athlete in the world. And then it puts a little star next to the athlete thing and says, if you have a body, you're an athlete. And yes, I remember it. I'm obsessed with it. And if you look at the work they've done over the last 50 years since I've been paying attention to this thing forever, whether it was Nike Air or it's the innovation they've done with materials with MIT or all these other things, like they're actually doing the work on the innovation side and then the inspiration side, the way they tell stories like, I still think that stuff is going to matter deeply. And I still. Yeah. If I had to bet on like five brands that are going to be around in 50 years, Nike would definitely be one of them. You know, I think it's an incredible brand. And you know, and I just, I do think this stuff is going to mean again, paradoxically, even more in the future than it has over the last 10 years because of the way, like shopping is changing.
Lauren Sherman
I hope you're right because otherwise it's a little depressing.
Jesse Darris
Think about the way your life works. You're going to have products in your mind that you commoditize. You've had that since you were a kid, right? Like in our family, we don't drink soda in our family. But when I was a kid, when my mom bought a 2 liter bottle of soda every single week at the grocery store and it was whatever was 99 cents that week. Right. She had no brand affinity, but there were other things where she swore by the brand. I still think that's the way we shop. Right. There are things that to you are a commodity. It doesn't matter. Or something that you're willing to try because why not? And the thing is surfacing something that's like, oh yeah, I love hair curlers. I'm just like, they know you. Like, they've been following you around the Internet. They know the likelihood is that you're going to convert and it's just like cheap bottom of the funnel, like really, truly direct consumer stuff. And then there's going to be a bunch of other stuff that you buy where you either buy it as if it's a subscription, like every time you buy sneakers you buy Nike, or you just become like you have deep affinity for the business and you continue to collect it in whatever it means. And the collection can be anything. It can be stuff that's consumable, it can be stuff that lasts forever. But I think you're going to have both. But I do think, given the way discovery, I think will shift, I think brand will mean more in the coming epic.
Lauren Sherman
Jesse, thank you for being here. This was super fun.
Jesse Darris
Yeah, it was a lot of fun. Thanks Lauren.
Lauren Sherman
Fashion People is a presentation of Odyssey in partnership with Puck. The show is produced and edited by Molly Nugent. Special thanks to Puck Co Founder John Kelly, Executive Editor Ben Landy, producer Maya Tribbett and Director of Editorial Operations Gabby Grossman. An additional thanks to the team at Odyssey. See Kelly Turner and Bob Tabador.
Lauren Sherman (continuation or interjection)
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Podcast: Fashion People
Host: Lauren Sherman (Puck correspondent)
Guest: Jesse Darris (President of Orchestra)
Release Date: March 27, 2026
Duration of Key Content: 02:46–58:47
This episode delves into the evolution of crisis PR, brand communication, and the rise and recalibration of direct-to-consumer (DTC) brands in the ever-changing fashion landscape. Lauren Sherman and Jesse Darris candidly discuss how brands build, maintain, and sometimes mend their reputations in an environment shaped by rapid shifts in technology, consumer behavior, and media coverage. Drawing on real stories from Warby Parker, Everlane, Glossier, and Reformation, the conversation moves from the early DTC era’s optimism to today’s nuanced, micro-targeted discovery, punctuated by social media and the rise of AI-powered recommendation engines.
On DTC’s value proposition:
“A bunch of brands were going to get created that were having conversations with consumers as opposed to at them.” (Jesse Darris, 19:42)
On the VC/DTC flood: “There’s just no question about it...people prioritized growth over having real businesses...” (Darris, 27:33)
On media cycles:
“If you’ve written about the rise, you have to write about its downfall, and eventually you have to write about its resurrection.” (Darris, 36:14)
On democratized coverage:
“I have the same distribution cost as Puck does...as we’ve totally democratized distribution...you just totally flattened the earth as it relates to how many people can opine...” (Darris, 38:48)
On brand value and AI-powered discovery:
“I could make a pretty compelling case that brand’s going to matter more...if you see it and they’re like, ‘this is the one you should buy’, if you’ve heard of it, you’re almost certainly going to pull the trigger...” (Darris, 53:45)
On AI search tools:
“Technology is today the worst it’s ever going to be. The one you’re going to have tomorrow is going to be slightly better...It’s going to get better and better at this.” (Darris, 49:33)
The discussion is lively, honest, and industry-insider, maintaining a mix of measured analysis and casual candor. Lauren Sherman’s tone is informed yet conversational, while Jesse Darris offers tangible examples, historical perspective, and optimism about innovation—even as he acknowledges cycles of hype and disappointment.
This episode is essential listening for anyone interested in how digital-native brands are built, stumble, survive, and prepare for the next chapter—where AI, accelerated discovery, and brand trust might matter more than ever.