The Exchanges

Q to tell you, I, I think it's a good ad, I mean, you're an entrepreneur, you're talking about this idea you had, but there's something about the ad that's polarizing, right? Which I actually don't think is a bad thing, because it got more attention than it probably would have gotten if it wasn't polarizing. Like, it was a YouTube ad. I mean, this ad has been parodied on Colbert.

A It's, it was in, so I have, um, Letterman and, and Seinfeld. Seinfeld, you know, saying, I just hate that Untucket guy, you know, walking down the street all smug. Then Letterman's first, Letterman's first appearance back after not having been on after leaving. His first line. Where have you been, Dave? What have you been doing? I've been looking to find a shirt that looked good untucked. You know, that's what, then you have Kimmel Colbert. Jim Gaffigan has an entire thing in his skit, a very funny, you know, thing about the untucked shirt. All of that, that is amazing, that stuff. It helps you. You're right. Everyone would pick their head up. Everyone would pick their head up and say, what is this lunatic talking about? Why does he care so much about his shirt?

AI assessment note: “You're right. Everyone would pick their head up”

Q idea, with the help of a friend of yours from Columbia Business School, Aaron San Andreas, you guys built Untuck It going from zero to like 73 stores in just four years. You've been through a lot. That episode was so powerful because it was had so many ups and downs and a lot of a lot at stake. First of all, how have things been since we last spoke?

A They've been okay, you know, it never ends. When I was on that episode, we talked about COVID, we talked about high interest rates taken on debt to survive COVID, and I believe we were just touching on tariffs, but we had not gotten there yet. I think we were, we were predicting that there could be some tariff issues. Well, they, of course, hit us hard. We had about nine million that was pulled out of our, our bank account that we had no line of sight to. And that was for two reasons. One, the normal tariffs, but then also Trump removed in the middle of the night, this three, two, one de minimis rule, which you could ship from Mexico. It had been in effect for like a hundred years without paying duties. So that, that kind of doubly hit us. Um, so we are fighting through it. We still have a loyal following. Um, we just started getting into wholesale. That's new. So that'll be our, now we'll have e-com stores and wholesale. Um, but we're working through the cash issues.

AI assessment note: “They've been okay, you know, it never ends.”

Q When you say out of spec, what do you mean by that?

A Out of spec meaning it was a large and supposed to fit one way, but it fit another way because it was out of specifications to what the shirt was supposed to be made. If it was supposed to be 25 inches, it was 28 inches. If it was, you know, if you measure 10 shirts from most companies and a large, same color, same shirt, you'll see a major variance of two to three inches because cotton grows and these companies don't want to spend the extra money to do the quality control needed To make sure that every shirt fits the same. So if you go into these stores, and this is what I used to do to solve my problem, I'd wander in to the J. Cruz of the world and try to find a shirt that somehow fit me at a little bit of shorter length than it, than the other ones did.

AI assessment note: “Out of spec meaning it was a large and supposed to fit one way”

Q So you're on this trip to Vegas with friends, and you start to talk to them, and they're validating your, your idea or your problem, and they're saying, yeah, that is annoying. You can't, they're saying the same thing?

A They're validating it, but with excitement, and usually I'm used to them. When I bring L for LP to them, they say, not gonna work, or you, you're out of your mind, or I bring a video wine blog, they say, Chris, you don't know enough about, you know, whatever it may be. This one Wasn't, oh, here he goes again. This was like, oh my gosh, this is amazing. And the perfect, the best example was my partner from Columbia Business School who I brought on, Aaron St. Andres. We would talk about ideas every day at Columbia, every day. And he'd hang up the phone 99.9% of the time while I was pitching the idea. This one, he's in an airport in Boston. He sits down. He remembers this. He's told this story 800 times, but he sits down. He said, I'm in. You don't have to tell me any further. I've been, I've had this problem since day one.

AI assessment note: “They're validating it, but with excitement”

Q I'm just trying to figure out why is this so complicated? I mean, I'm, I'm wearing, as you know, I'm wearing one of your shirts now. I wear lots of button-down shirts. What, what's so hard? What, why is it so hard?

A There's a reason why I found out that people do not make shirts designed to be worn untucked. Our shirt has to be in spec every time. If it is a inch too short, you can't wear it. If it's an inch too long, everyone else has it. You have to hit it each time. Cotton grows. You know, you can pull down most shirts an extra inch if you just give it a little tug. It shrinks, it moves, the heat affects it, all these different things. So we had to implement this crazy quality control process where we're washing each yard of fabric. Where we're rejecting it if it doesn't hit spec. I rejected a shirt an inch out of spec the first time, and they said, that's not the way fashion works, Chris. They're not going to work with you. The factory will not work with you. And I said, then I don't have a business idea. When you make a, when your name is untucked, and you're, you're talking about this perfect length, it has to be perfect.

AI assessment note: “Our shirt has to be in spec every time. If it is a inch”

Q So, basically, the blog, the wine blog, or vlog, becomes your thing for a while, because you would go on to post videos, video diaries about wines, and I'm assuming it was, you know, you would taste wine, you would talk about the wine. How are you, and also traveling and trying wines, how are you doing that and also doing your day job selling medical equipment?

A I developed a strategy as a sales rep. I became very close with my customers, um, and I was very open with them. It's funny, I would tell them what I was doing, that I was not, I was an entrepreneur. That, they liked me more because of that, because I wasn't the guy coming in to try to push them to buy stuff. No one likes a sales rep. I mean, I'm joking a little bit, but you know, it's like, they make movies about it. So I was the opposite. I'd come in and they'd look forward to talking to me. What'd you try to do? Where'd you go? What's your latest business idea? So I developed this ability, which my managers, I think, hated, and everyone I worked with, that I didn't have to go to the accounts, and they still would buy from me. And that's what allowed me to last a cheese so long, because as much as they wanted to get rid of me, they couldn't, because I was hitting my number.

AI assessment note: “I developed this ability... that I didn't have to go to the accounts”

Q But who was doing all of your, before that, who was doing the website, and who was designing the Who was dealing with, like, uh, fulfillment, for example? Who was doing that?

A I, I had one guy shipping in the storage unit, and I would go there an hour at the end of the day. It's funny. I was ironing through 15. I ironed every shirt that, I would come home. The worst part of this whole journey for me, the entire Untucket journey was coming home after being out to dinner and seeing 75 boxes in front of my apartment door and having to iron them and repack them. In the middle, right up to the middle of the night. Iron, clip them, hang them outside if they, but we didn't, we were very lean. That's, me and Aaron did almost everything until Bjorn, and then in 15, on the way to fifteen million, we quickly hired. Like, that's where it turned on quick.

AI assessment note: “I had one guy shipping in the storage unit... me and Aaron did almost everything”

Q All right, so already in year one, I mean, you're kind of doing this R&D. Aaron is working at Price Waterhouse Coopers, but he's on board. He's like, I am in. I will, I I want in. So what was he doing? He was helping you kind of craft the PowerPoints and build a business model?

A Yeah. He was building the, cause we had to raise some money. Um, we had to build out a website. We had to, uh, you know, start to think about how to market. So he was doing, he was doing a lot of the financial side of things at the time I was doing the shirts. Um, but I'll tell you things like untuck it, that name, I came up with that and then agonized it over a year of all these people telling me not to use it. You know, shirts designed to be worn untucked. That took a year. I'm, you know, you laugh at this, but you realize why some of this marketing stuff means something. You know, you want to rush it. Oh, it's shirts worn to be made untucked or whatever. That took a long time. So we were working on things like that. And then, uh, raising money was impossible. You know, you go to people and tell them you want to make, you're a medical sales rep and you're going to go make a shorter shirt, right? What are you talking about? How's that?

AI assessment note: “He was doing a lot of the financial side of things at the time”

Q But, but basically spending as much time as possible on, on this other project. And, and were you mainly, like, looking for value wines, like talking about wines that people could go buy at this, you know, at the, whatever, Total Wine or whatever wine store they were going to, Costco?

A Yeah. What I was trying to do was wine was very, um, the only word I have is like snobby back then. It's kind of changed. Young, young people didn't drink wine back then. You know, young people, let's say without money, didn't drink wine. I wanted to show people that I could wear a backwards hat, you know, sitting there in a t-shirt and love wine as much as the guy in France does who's wearing a tuxedo teaching about wine. So I was trying to go after that type of person. The other thing I tried to do was, you know, Golf is thought of as a way to get ahead in sales, right? That's always been the case. Golf and that. So to me, wine, when I would go into these doctors and I knew what I was talking about as a 23 year old with wine, they liked me. They wanted to go to dinner with me because I knew wine.

AI assessment note: “Yeah. What I was trying to do was wine was very... snobby back then.”

Q Chris, one, one final thought. If, if, if Adrian is to, was to raise cash, you know, in the next, let's say two or three years, where would you put that cash?

A I, um, I like to simplify this stuff in a way. If you're, especially if you're an e-commerce brand, at the end of the day, you need good product and then you market and you sit back, right? That's how you're going to know whether you're going to succeed. And I don't like wasting time. Like this was me, right? I had no interest in building a five million dollar brand. I wanted to build a big brand. And if I wasn't going to, then I didn't need to be hanging around wasting time doing it. That's just me. That's not everyone. So my point is bring some money in and allocate it to marketing. And see if you can get some momentum, but that's changed a little bit because it's very, very hard on paid social to get momentum, right? So you have to think about other ways and maybe it's, you know, and I'm making this up. Maybe there's a volleyball radio something, or maybe there's something, you know, and you start marketing there for nothing. And all of a sudden people are coming in. And then of course for you, I mean, I would focus on content on Tik TOK and on, you know, telling your story, fine tune your story. But I would use the money. I hate to say it sounds basic, but it's product and marketing, right? That's, that's going to determine whether you're, if people, if you're getting the brand in front of people and they're not buying, well, there's a problem, right? I'm just saying, get t…

AI assessment note: “bring some money in and allocate it to marketing.”

Q And was it just intuitive? Like, hey, I listen to those things. I like those things. Maybe your partner Aaron listens to those things, and that was it? Or did you do, like, some research to find out, hey, where, where should we go?

A Back then, we were big testers. Test it, move on. Test, move on. Podcasts became the next thing. Test it. You know, we were in the Journal, the USA Today, New York Times. No one was doing that stuff. They were just doing paid social at that time, because that's where the world was going. By the way, we had 30 billboards around the country at one point. No one was doing a billboard, but we had this tagline, untuck it, shirts designed to be worn untucked. That's all we had to put. We didn't even have to show the clothing. So it was a, it wasn't, you got to think about this. It was almost like it wasn't a, a clothing brand. It was a concept.

AI assessment note: “Back then, we were big testers. Test it, move on.”