UNTUCKit: Chris Riccobono

On a trip to Las Vegas, Chris Riccobono found himself wearing the same J. Crew shirt over and over; it was the only dress shirt he had that looked good untucked. All of his other button-downs were too long and looked sloppy. His buddies all said they had the same problem, so Chris decided to seize the opportunity and launch UNTUCKit with a friend. Keeping his day job as a GE salesman, he embarked on a crash course in how not to make a shirt. Thousands of defective button-downs later, UNTUCKit hit its stride, and the big fashion brands began to copy the untucked look. In 2020, UNTUCKit came within inches of a lucrative acquisition, then nearly went bankrupt, but today has grown into a thriving brand. This episode was produced by J. C. Howard, with music by Ramtin Arablouei. Edited by Neva Grant, with research help from Kerry Thompson. You can follow HIBT on Twitter https://twitter.com/HowIBuiltThis & Instagram https://www.instagram.com/howibuiltthis, and email us at [email protected] mailto:[email protected]. Sign up for Guy's free newsletter at guyraz.com http://guyraz.com/ and on Substack https://guyraz.substack.com/. See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

Speaker names marked ? are inferred from speaking time and the show’s known hosts — they are not voice-verified.

• 0:00Guy Raz?

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• 0:46Guy Raz?

  build the prototype, analyze the market, maybe even come up with the idea, what separates the people who actually build something from everyone else? I don't have a clean answer yet, so I've been sitting with it with Claude. There's hope in hard questions. Ask yours at claude.ai/hibt. We get support from U.S. Bank. A question I love asking founders. What's the one decision you almost didn't make? The one that changed everything? Because it's never the obvious stuff. It's never, I decided to start a company. It's the small, boring, Tuesday afternoon decision you barely remember making until you realize it's the reason everything after it either worked or didn't.

• 1:32Guy Raz?

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• 2:16Guy Raz?

  on gas and EV charging, office supply stores, cellphone service, and restaurants. You pick up an extra $750 cash back as a bonus. And you've got a low APR on purchases and balance transfers for 12 months while you're scaling. Same business, same expenses, two completely different outcomes based on one small decision. Visit usbank.com/business to learn more. The creditor and issuer of this card is US Bank National Association, pursuant to a license from Visa USA, Inc. Some restrictions apply. If you travel often, you'll want to hear about this unprecedented offer. For the first time ever,

• 3:00Guy Raz?

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• 3:45Guy Raz?

  or bring a guest to the Delta Sky Club. Make every trip feel more rewarding with the car that upgrades your travel. Apply today at delta.com/cardsocial. Offer ends November 4, 2026. Minimum spending requirements and terms apply. Flights are fulfilled as flight certificates valid for Delta Comfort or Delta Maine to select domestic destinations. Book 21-plus days in advance. Up to $80 per person and taxes and fees apply. Other restrictions apply. When I pull up to a gas pump to fill my car, I'm not thinking about chemistry or engineering. I'm thinking about getting in, filling up, and getting on with my day. And it reminds me a little bit of the founders I talked to on this show, because the best

• 4:27Guy Raz?

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• 5:24Guy Raz?

  Tell me about that first batch of inventory, because you say that the shirts were terrible, which is shocking. I mean, I don't... Well, it comes off the boat in New York. You open the boxes and what? You see right away that they're not good?

• 5:38Speaker 01

  Well, actually, when people started wearing them and saying that they now used it for a rag for their car, that's when it really... But you know what's funny? You know what's funny? We thought through it and said, you know what? We'll one day get them back. We'll keep a list of those people, and I'm going to lose X amount of customers. I mean, you didn't have a choice. This is entrepreneurialism. You just have to survive.

• 6:07Guy Raz?

  Welcome to How I Built This, a show about innovators, entrepreneurs, idealists, and the stories behind the movements they built.

• 6:19Guy Raz?

  I'm Guy Raz, and on the show today, how a guy who knew nothing about shirts rolled up his sleeves and started Untuckit, a brand that seemed like a gimmick, until it started a trend.

• 6:37Guy Raz?

  Some brand names sound like they could be anything. Uber could be a band. The skincare brand, Jack Black, could be a whiskey. Bull and Branch, a law firm. But then, there are the brands that wear their purpose on their sleeve. Fresh Pet, ButcherBox, Paperless Post. You know exactly what you're getting. And that's the direction Chris Riccobono went with his company, Untuckit. Just hearing the name, you kind of get it. It's a shirt designed to be worn untucked. Simple idea, clever name. Chris has even said it's the best business decision he ever made. But in the early days, it sounded a little gimmicky.

• 7:22Guy Raz?

  Late-night comedians roasted it. Chris even starred in the ads himself, earnestly explaining how he just wanted a shirt that looked good untucked. And people laughed. But here's the thing. Chris was right. It was a real problem. So real, in fact, that a few years later, big brands were copying the idea. But naming a company Untuckit was just the start. To get past the gimmick, the shirts had to be good. Chris and his co-founder, Aaron Sanandris, priced them like a premium product, around $80 a pop. And slowly, they built a brand. Now, neither of them had any experience in fashion.

• 8:05Guy Raz?

  They made just about every mistake you can imagine, including a disastrous first run of shirts. And for many years, both Chris and Aaron kept their day jobs while running Untuckit on the side. The business was eventually doing so well at one point that it was almost acquired for about 3/4 of a billion dollars.

• 8:27Guy Raz?

  That is, until the deal fell apart and almost tanked the entire company. But today, Untuckit is once again thriving. Over 80 stores, a growing wholesale business, and a fast-growing women's line. And Chris Riccobono, he finally proved that you could build a brand around an untucked, button-down shirt. Chris grew up in New Jersey, where his dad was a doctor and his mom was a nurse. He was a standout tennis player in high school, and at Providence College in Rhode Island, he studied finance.

• 8:59Speaker 01

  It's funny. I knew I wanted to be an entrepreneur in college because I was scared about corporate America. Got a lot of anxiety in interviews. My first interview I ever did at Providence, the guy stopped the interview because he could hear my heart beating, literally said, "I can hear your heart beating, let's just talk now." So I was very worried about my career, and I kept saying in my mind, "I'm going to find a way out of this." And that was the way I was always approaching post-college. I was going to get a job, and then I was going to focus on finding my own thing. And I got nervous that how am I going to work my way through up through an organization? I'm not a great public speaker. I'm not great at Excel, or PowerPoint, or all the socializing you need to do to move up.

• 9:44Speaker 01

  That just wasn't my thing. I knew I wasn't good at it.

• 9:48Guy Raz?

  You knew that you would get to a company, because I think you eventually worked for General Electric for quite a while as a sales in their medical sales department. But you weren't going to stand out because you weren't the most, I don't know, social and charismatic. You didn't have like-

• 10:06Speaker 01

  I just couldn't do it. And I knew it, brother, right when I started with GE, and it scared me because then I started saying, "What am I going to do? Like, I am in trouble. I need to be successful." I was so into, I wanted to succeed in my life. I wanted to do something great. But I knew it couldn't happen in corporate America.

• 10:23Guy Raz?

  While you were at GE, you already knew, because you would spend, how many years total would you spend there?

• 10:30Speaker 01

  Probably 10.

• 10:31Guy Raz?

  But you knew already, early on, that you were not going to really climb up the ladder there.

• 10:37Speaker 01

  Yeah, just, I couldn't get excited about selling medical equipment. I guess that's what it was. I just, it didn't excite me. All these guys who I worked with, you know, and the other sales teams, like 20, 20, 30 people. They all were openly negative about, they thought I was a dumb guy. Like, meaning they would say, he's just not good. Or I didn't work hard, all these different things. But the reason I wasn't good is because I was totally unfocused. I was focused on what I was going to do after that job.

• 11:05Guy Raz?

  Got it, okay. So you're at GE, and I think a couple of years in, you decide to do an MBA program at Columbia while you're at GE. So they, a lot of business schools have these executive MBA programs that are like eight, they take like, you know, 18 months or, and you take classes on the weekends and one day a week. And, and by the way, did you, did you decide to do this because you thought, all right, this is going to help me jumpstart and help me figure out how to start my entrepreneurial journey? What was that thinking behind doing an MBA?

• 11:45Speaker 01

  No, it was very simple. I, I knew I had to progress my career while I worked on an idea. And I kept striking out with entrepreneurial ideas because I always tell entrepreneurs, you can't just be an entrepreneur, that's not a job opportunity. You have to create an idea or a company or a concept in order to become an entrepreneur. So now I said, okay, now I'm in Columbia, I'm 27, at least I'm progressing this career.

• 12:10Guy Raz?

  But you're still a GE. It's a steady job and it's a paycheck, basically, right?

• 12:15Speaker 01

  Exactly, yep.

• 12:15Guy Raz?

  And I think you were, I think you were already married at this time, right?

• 12:19Speaker 01

  I got married in 2009.

• 12:22Guy Raz?

  But to somebody you met in college as an undergraduate.

• 12:24Speaker 01

  Right, right, exactly.

• 12:26Guy Raz?

  Who's still your wife today.

• 12:27Speaker 01

  Yep.

• 12:28Guy Raz?

  Okay, so you, you're still doing your job, it's 2008. You've got an MBA from Columbia and clearly you want out, but you got to come up with an idea. And we're, this is a period of time where we're going to talk, we're going to grind through some of these, where apparently you came up with like dozens of different business ideas and, and kind of trying to see which one would work. And I guess one of the first ones was a... A wine blog or vlog, video blog called Pardon That Vine, which was, you would talk about wine, we're gonna get to in a sec, but tell me how that idea came about.

• 13:10Guy Raz?

  Cause I know around this time, I mean, I think a lot of people who know this world might think of like Gary Vaynerchuk. That's was an early thing that he did.

• 13:18Speaker 01

  Yeah, it was an idea. It was the only idea I had. So basically put it that way. And all these other little ideas I tried. And I also get very bored easily. So the Columbia MBA got me excited. I was working really hard. So now I'm back doing nothing again, selling medical equipment, no ideas. I said, what do I like? I only like really one thing I'm massively passionate about was collecting and drinking wine. And I would spend hours and hours and hours reading about it, you know, and learning all these things that were never gonna serve me any purpose other than just, I enjoy doing it. Gary Vaynerchuk, I bought wine from him when he, before he started that blog. I had this little camera and I, I wasn't sure what I was gonna do. Because I didn't, um, I, I was thinking, Gary's got a massive following.

• 14:02Speaker 01

  I'll be a more laid back version of Gary. So I taught myself all this wine. I started filming videos, traveling around the world, tasting wines, interviewing people with this small little camcorder. They thought, it's funny, I would go to France and they thought that I was coming in with this big camera crew. And I would come in with my mom or my wife with this little camera. And they'd have all these high end Bordeaux's lined up for me. And I would do the, they thought I was important back home. Little did they know 15 people watched the show.

• 14:28Guy Raz?

  So, all right, so you, you decide to do this. First of all, you, you were into wine? It was just a thing you were into?

• 14:35Speaker 01

  Yeah, that story is, I was a, I was a guy who loved, you know, drinking beer with my friends and socializing at college. And I graduated, my wife was still there at the time, or my girlfriend. And I was so unhappy and my older cousin said, come over to have dinner. And I'm thinking, you know, I'm still not, I'm a young kid. I want to be at a bar. I want to be, I said, fine, I'll come over to have dinner. And he says, go in the wine cellar and pick any bottle of wine. He said, pick a sparkling wine. So I come up, I bring a sparkling wine up and he tells me 30 minutes about this wine, where it's from, how he found out about it. We drink it. He said, go down, pick a white. I go down, same thing. Then for then three more bottles of red and the storytelling and, you know, and I had an unbelievable night there, you know. And I said, wow, this is

• 15:19Speaker 01

  amazing. Like this is, the wine is just incredible. Brings family together. And that was the day I became obsessed. I started studying about it, reading about it, collecting it. And that's how I got into it.

• 15:30Guy Raz?

  All right. So you decide that this could be a cool venture and you call it a pardon, pardon that vine. But tell me, what was the business model? Was it going to be ad-supported? What did you, how did you think you were going to make money from this thing?

• 15:43Speaker 01

  I was thinking I could consult. I can go, you know, which I did, you know, go consult, go speak at different events, you know, people's parties, which I did a bunch of. I thought I could build, remember, that's once again, right when social media wasn't really out there. I guess it's like-

• 15:59Guy Raz?

  YouTube was new, was very new, yeah.

• 16:02Speaker 01

  What could have happened to me if, if I was better at it and maybe technology was a little better, maybe the goal, I would have been that first influencer, right? Or what, you know, it just never, I wasn't, that wasn't my thing. But I guess that was the buildup followers. I remember trying to get followers on Facebook, which there was only Facebook at the time. And that's kind of before it all started. So I think the plan was there. I just didn't, you know, yeah, it was tough to monetize. That's why I stopped doing it.

• 16:29Guy Raz?

  This was one of many ideas. I think there were some other sort of more short-lived ideas, like you had an idea for an online dating service for little people.

• 16:39Speaker 01

  Yeah.

• 16:39Guy Raz?

  Love for little people, L for LP, actually registered domain.

• 16:44Speaker 01

  Yeah, I can't get away from this one. Yeah, L for LP with my cousin.

• 16:49Guy Raz?

  This is a real idea that would basically help people who were born with the certain conditions that make them small, that they could meet other people like them.

• 16:59Speaker 01

  Yeah. And another one that I get- Told that I'm crazy for today because it sounds odd to, but back then, once again, the internet's like, all this stuff is new. I mean, an L for LP, if followed through, would have been a successful business. It just, you know, never went, went anywhere. And that's, you know, listen, that's the problem with so many entrepreneurs is following through and actually finishing it and doing it. And a lot of times I didn't do that because I was intimidated and I never did it.

• 17:25Guy Raz?

  But there's also the flip side, which is you come up with a lot of crazy, weird, unusual ideas and that will eventually lead to the idea.

• 17:33Speaker 01

  Yeah. And that's such fun. It's funny. All these things were happening before it became mainstream today. So I, it could have worked, meaning I wrote with my cousin four different reality programs. None of them were ever made, but you're right. The biggest thing is it kept me going. It kept me getting excited. It kept me kind of pushing myself to try to come up with that idea.

• 17:54Guy Raz?

  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?

• 18:17Speaker 01

  I developed a strategy as a sales rep. I became very close with my customers. 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, that'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 achieved so long, because as much as they wanted to get rid of me, they couldn't because I was hitting my number.

• 18:59Guy Raz?

  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?

• 19:15Speaker 01

  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 is 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.

• 19:55Guy Raz?

  I mean, this is, it's, it's interesting because the, the fact that you were doing this and it was actually, in a sense, helping you, was something very real, but it wasn't a business. There was no income coming from this. And now we're coming into this next idea, which is, which is shirts, nice shirts that you could wear untucked, right? Um, because any, any, certainly guys know that when you get a dress shirt, they're long. They're designed to be long because you want to tuck them in and get them as fitted as possible. And so, tell me about this. We're around 2010. You're still a GE. You're still selling, selling medical equipment. You're doing the, the wine vlog.

• 20:40Guy Raz?

  How does this kind of light bulb go off in your head about, about an idea to make shirts?

• 20:47Speaker 01

  Well, let's be clear for younger people who are listening to this. This problem doesn't really exist today because everyone's kind of copied and made of, a fairly reasonably fitting shirt. In 2010, every shirt came down to your mid-thigh unless it was an out of spec shirt. And I had one of those. I had one J. Crew small, I'm a large, that somehow is out of spec and it fit me perfectly.

• 21:09Guy Raz?

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

• 21:12Speaker 01

  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 you measured 10 shirts from most companies in a large, same color, same shirt, you'll see a major variance of 2 to 3 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. Crews of the world and try to find a shirt that somehow fit me at a little bit of shorter length than the other ones did.

• 21:53Guy Raz?

  Right.

• 21:53Speaker 01

  There's no consistency. Shirts looked sloppy and were too long. And I would always ask my buddies, "Do you have this problem? Do you have this problem?" And they all would light up and say they have the problem, and I never would do anything about it because how in the world am I going to start a fashion brand? I don't know anything about it. I don't know how to make a shirt. I don't know all these things that you need to start this company. And finally, I went to Las Vegas. I was out with my friends. I think it was a bachelor party. Wore the same shirt four nights in a row. Became a big topic of conversation about everyone's struggle. And I'm looking at my friends and how silly they look. And I said, "I gotta find a way to do this."

• 22:28Guy Raz?

  You're wearing this J. Crew shirt that you would wear untucked.

• 22:33Speaker 01

  Wore it untucked because it was a small. And because it was a small but somehow out of spec, the length of it fit much shorter than a large would have fit.

• 22:41Guy Raz?

  Yeah. So basically, you guys are talking about this with your friends. And you were like, "Hey, I want a shirt that fits sort of like a well-fitted t-shirt, but that's with a collar and button, a button down, basically."

• 22:57Speaker 01

  Yeah, you know, it's funny. Shirts designed to be worn untucked. Everyone laughs at that. That's so simple. No shirts were designed to be worn untucked. There were not even the ones-

• 23:07Guy Raz?

  Guayaberas. There are guayaberas, for example.

• 23:09Speaker 01

  Well, that style shirt, yes. But that's not what we were making. You know, the oversized, cut-off, which are also too long. But you're right. I would have to deal with many people's negative feedback about that existing. But a nice dress shirt, if you will, or a plaid did not exist. And it was never designed that way. And therefore, because you didn't need it to wear it untucked, these companies, not like going back, I know the specs, I'll bring it up again, it was a big thing because- Companies didn't factor in length. They didn't care 31 inches, 33 inches, 32, 35. Don't worry about it. You don't even have to QC that. It doesn't matter. They're not going to notice.

• 23:47Guy Raz?

  Because you're tucking it in.

• 23:49Speaker 01

  Because you're tucking it in.

• 23:50Guy Raz?

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

• 24:02Speaker 01

  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 going to work. 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 Sinandres, 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 to 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.

• 24:43Guy Raz?

  This is Aaron Sinandres, right? He's your, you meet him, you had met him when you did your degree at Columbia and he, I think, was working at Pricewaterhouse.

• 24:53Speaker 01

  PWC. Yep. He was a partner at Pricewater.

• 24:55Guy Raz?

  PricewaterhouseCoopers. He was a partner. So he was an accounting.

• 24:58Speaker 01

  He was someone similar to me in that he would also pitch ideas. We always wanted to think of ways to, to start a company.

• 25:05Guy Raz?

  He's somebody that you, just tell me, why, why was he somebody you thought would be the right fit to start a business with? Aside from the fact that he had a bunch of ideas, what was it about him that you thought could work with your personality?

• 25:19Speaker 01

  He's just incredibly smart and always asked the most questions at Columbia, very inquisitive, very good at multiple things, you know, like I knew that I needed someone. I couldn't put together a beautiful PowerPoint to go raise money. Just wasn't my thing. I couldn't put together a detailed financial model. And many times there's a guy who can put together a detailed financial model and then a guy who can put together a great PowerPoint. Aaron was very versatile. He could do all that stuff. But when I called him on this and he was that excited. That was the other thing, because I finally found someone who believed in this idea.

• 25:53Guy Raz?

  You didn't know about how to design a shirt. You're not a fashion guy. You didn't go to Fashion Institute or whatever. Aaron is a finance guy. So let's just talk first about, you know, in a lot of industries, if you don't speak the language, they don't take you seriously. Like, if you don't know what a hem is, or I don't even know the language in apparel, you know, in this kind of apparel, but they have language. They have a code that they speak in that you now know, you know, 20 years later, but then you didn't. So how did you eventually find somebody who agreed to like make a prototype for you?

• 26:30Speaker 01

  Well, you're right. Like, I wanted to make sure. I went into the fashion district. I wandered in and out. I brought my one J. Crew shirt. I asked them to make it. They said, "I'm crazy. That's not the way it works." I said, "Please make it." I was meeting with button manufacturers and...

• 26:44Guy Raz?

  You're talking about the garment districts in New York City? You actually went into garment makers and asked them if they could make you a custom shirt?

• 26:51Speaker 01

  Yeah, I wandered in the street and looked at places that have sewing machines. And I went in and I said, "Can you make me a shirt that looks like this?" You know, I figured that was the first step. I mean, I didn't know what else I was gonna do. I didn't know a factory or how to... I didn't know anyone in the industry. So me going in there, I think they were like, "Who is this guy? And, you know, what is he talking about? He wants to make a shorter shirt?" By the way, I went through my whole pitch to people who had been making shirts for years and years and years and years. And they'd say, "No, you cannot make the shirt that short. That's not the spec of a shirt." And I'd say, "What are you talking about?" They're like, "We have specs, right? If you make it 20 inches across, we then make the length 32 inches." I'd say, "I don't want it 30. I want it 28.75 inches."

• 27:33Speaker 01

  So the length, by the way, 28.75, that's my favorite number in the world.

• 27:37Guy Raz?

  Inches.

• 27:38Speaker 01

  Yeah, on a medium from the... I shouldn't probably be telling people that, although I guess they can measure it. But 28.75, and then they... I was just working with these people. They... Some people told me they can't do it. Some people told me they could do it. Through each person, I met someone new and met someone new. It was really that type of story. So I just learned, it was like, I was taking my time. I had a full-time job. There was no rush, and I was learning. It took, you know, two years to get to market,

• 28:07Speaker 01

  you know, to finally get that right shirt. But that was the hardest part, is finding how to make the shirt.

• 28:13Guy Raz?

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

• 28:29Speaker 01

  Yeah, he was building the, because we had to raise some money. We had to build out a website. We had to, 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. But I'll tell you, things like Untuckit, 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. You know, you laugh at this, but you realize why some of this marketing stuff means something. You know, you want to rush it out, shirts worn to be made untucked or whatever. That took a long time. So we were working on things like that. And then 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?

• 29:15Speaker 01

  What are you talking about? How's that?

• 29:17Guy Raz?

  No, it's not a good bet. It's not a good bet. Not at all. But, but before we get to the money side, just, just going back to you, what you and Aaron were doing, were both of you living in New York City at the time?

• 29:28Speaker 01

  I was living in, I had just moved to Hoboken and Aaron was living in New York City.

• 29:33Guy Raz?

  So how often were the, how often were you meeting?

• 29:37Speaker 01

  We meet at a diner, you know, two times a week in the city on Fifth Ave. And we just, listen, you never believed that this company, it was a shorter shirt. This wasn't technology. This wasn't, I started a, and I'm going to work on an Uber app, right? And I'm going to design it. This was, I'm making a shorter shirt and I'm going to try to break into the fashion industry. You never think it's possible.

• 30:02Guy Raz?

  When we come back in just a moment, Chris and Aaron get a crash course into how not to make a shirt. Stay with us. I'm Guy Raz and you're listening to How I Built This.

• 30:24Guy Raz?

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• 31:06Guy Raz?

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• 31:51Guy Raz?

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• 32:36Guy Raz?

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• 34:02Guy Raz?

  Hey, welcome back to How I Built This. I'm Guy Raz. So it's 2011 and Chris and his business partner have put together about $150,000 to start a new brand of shirts designed to be worn untucked. And now Chris has to get them made.

• 34:20Speaker 01

  I connected to this guy from Poland who had an office in New York City. And he showed me a bunch of fabrics, looked at 100 fabrics, said, these are the ones I like. He said, I'll make them for you in Poland. No process, you know, no, you know, now you're supposed to do tech packs and big order forms and this and everything automated. I told the guy, I don't know, this is all I got. It's me and my partner. It was such a different time, so they were willing to do this. Today, there's thousands and thousands of people launching clothing brands every day because of the ease of doing it now. You know, with the ability to grow. So back then it wasn't. So that's a benefit. I always say, I was lucky at the time I did it.

• 35:03Speaker 01

  If I was five years later, it wouldn't have worked out, I don't think, the way it did, or 10 years.

• 35:08Guy Raz?

  So this guy is a Polish guy in an office in New York and he had, what, he had his own factory in Poland? Or he had connections to a factory?

• 35:15Speaker 01

  He was the broker for that factory in Poland.

• 35:17Guy Raz?

  I got it. And that was going to be cost effective to do in Poland at the time?

• 35:22Speaker 01

  Yeah, it wasn't going to be the cheapest. I just had no other contacts, you know, in Asia, so.

• 35:26Guy Raz?

  And the shirts were going to be made out of cotton, I'm assuming?

• 35:29Speaker 01

  Yeah, it was all cotton, basic stuff.

• 35:32Guy Raz?

  How many shirts did you order in that first?

• 35:35Speaker 01

  Only a thousand.

• 35:36Guy Raz?

  And how much did that, how much did it cost you?

• 35:38Speaker 01

  Probably 20,000, somewhere around that.

• 35:41Guy Raz?

  And you were going to sell them for like 30 bucks or something?

• 35:44Speaker 01

  No, no, we were more than that. I think we were like 78, 88.

• 35:48Guy Raz?

  Okay, so it was going to be a premium, sort of premium shirt, right?

• 35:52Speaker 01

  Well, so we, the funny thing is, we made terrible shirts in the first year. Like, I never really got there until year four of making a really nice shirt because I didn't know what I was doing. I didn't even know you had to pre-wash a fabric to take out shrinkage. No one told me. Some of the fabric, we didn't test the fabric, so the arms on our first plaid grew really big after washing and the rest of the shirt shrunk.

• 36:15Guy Raz?

  Wait, hold on. So tell me about the, about that first batch of inventory. Because, I mean, you say that the shirts were terrible, which is shocking. I'm sure you, you sink all this cash into it. You don't have a lot. Wait, it comes off the, off the boat in New York, you open the boxes and what? They, you see right away that they're not good?

• 36:33Speaker 01

  Well, actually, when people started wearing them and saying that they now used it for a rag for their car, that's when it really, but you know what's funny? You know what's funny? I didn't. I thought we thought through it and said, you know what? We will one day get them back. We'll keep a list of those people, but we'll get our cash back. They'll buy the shirt. They're not going to return it, right? They're gonna, and I'm gonna lose X amount of customers. I mean, you didn't have a choice. This is entrepreneurialism. You just have to survive.

• 36:59Guy Raz?

  You had to sell those shirts even though they weren't.

• 37:01Speaker 01

  You had to sell them. Yeah, that's the point. And today you wouldn't do that. I loaded my third bedroom up with all the shirts. I brought a UPS printer and we grew from there. I mean, we shipped, I shipped every night from my, from my apartment. But we remained positive because when the guys got the shirts, the excitement, we'd get paragraph emails from customers who found out about the brand. Thank you so much. I've been looking for this. I can't believe I didn't do it myself. This has been a problem in the industry. No one writes paragraphs to clothing stores, you know, one after another. Every day there'd be paragraph emails. By the way, it kept going. The next line that came out, we had, I got the first shirt. I, I'm measuring it out. I see a little thing on the button. I pull the button up and it falls off.

• 37:46Speaker 01

  I do, I look at the next button and the same, yeah, the same thing. It pulls off. Next one pulls off. I take another shirt. The factory forgot to tie on the buttons the right way on this machine. The machine was broken on every single shirt they made. So we sold them. We followed up with an email to everyone that, hey, we're reimbursing your account $5. There was an issue with our machine. You know, take your shirt to the dry cleaner and get them put back on.

• 38:12Guy Raz?

  By the way, these were all being made in that factory in Poland.

• 38:16Speaker 01

  They were all being made in a factory in Poland.

• 38:17Guy Raz?

  And, and, and not to knock Poland because Poland, I mean, Poland today, I think would be prohibitively expensive. It's, it's a, you know, it's an industrial, you know, power and it's, it's got manufacturing and it's a EU country and, but I'm, my obvious question is, well, why would you keep working with that factory if the shirts they were making sucked?

• 38:38Speaker 01

  First of all, you didn't have a choice. Like, it's much harder than you think as a company making a thousand shirts, or whatever the shirts we make. Like, they just don't, they didn't even pick up your phone call for a thousand shirts. The other thing is, it wasn't really there. I'm supposed to be submitting this tech pack that has washing instructions, fabric testing, testing buttons. I'm sure they were just, they had a thousand shirts, making no money on it, taking a chance. They're making the shirts and they're sending them over.

• 39:05Guy Raz?

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

• 39:15Speaker 01

  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 an 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 could 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 gonna work with you. The factory will not work with you." And I said, "Then I don't have a business idea."

• 39:55Speaker 01

  When you make a, when your name is Untuck It, Shirt Design, and you're talking about this perfect length, it has to be perfect.

• 40:02Guy Raz?

  Has to be perfect, okay. But I guess the reason why it's not perfect every time is because shirts are still, there's still a lot of human hands involved in each shirt, right? It's not a machine that's making every shirt. It's not like it's going on a factory line and it's just a machine that's just cranking it out.

• 40:20Speaker 01

  It depends now. There's some 3D technology and printing and stuff.

• 40:23Guy Raz?

  But then, you're saying it was still, there were humans with, you know, sewing machines in their hands, and they were doing the hems, and they were stitching the stitches and everything, and that, that was...

• 40:34Speaker 01

  Right, now think about this, like, if we're making 15,000 white, medium shirts, which we do, and they put them into a washing machine, a massive tank, right? And they dry them, and they wash them, and they heat them. If one's too close to the heat, and one's a little further, or one's, that's the other problem. When you're scaling, it's very hard to make that same shirt at the same length every time. And you have two different people making it and all these different things.

• 41:00Guy Raz?

  And your promise was, hey, it's gonna look great as an untucked shirt. But if it was slightly off, or it trunked too much, or you know, or it it the whole thing gets thrown off balance.

• 41:14Speaker 01

  And there's no difference. And then we blend in with everyone else and the idea goes away and we disappear.

• 41:19Guy Raz?

  Okay, so again, I go back to my question. If that factory in Poland sucked so much, why did you keep working? I guess the answer is you had no choice. It was the only they were the only ones.

• 41:29Speaker 01

  Yeah, we did. We had no choice and we quickly fixed our product. I think that that's and listen, this is now 14 years. But I do know we I don't have the exact timeline, but I do know we pivoted quickly. And improve the shirts because they got really good in like, you know, the third year.

• 41:44Guy Raz?

  How did you do that? How did I mean, did you were you flying to Poland to that factory? Did you basically at a certain point imagine you stopped working with them?

• 41:51Speaker 01

  I stopped working, but I also found this Swedish guy named Bjorn, who's still with me today, older guy teaches at the Fashion Institute.

• 41:59Guy Raz?

  How did you find him?

• 42:01Speaker 01

  I was working with a freelance guy who was not very good. Bjorn walks in for a meeting with him and he throws on the shirt and he says, what do you think of this shirt Bjorn? And Bjorn destroyed the shirt, says the worst made shirt I've ever seen. And then he contacted me outside that meeting because he thought there was something there. Now, the good news is, the good news is we grew unbelievably slow, you know, $90,000, $300,000, $500,000.

• 42:30Guy Raz?

  This is year one, two, three.

• 42:32Speaker 01

  Yeah, then, you know, 3 million, 15 and up from there. So that three to 15 was a big difference. But the great thing was, we always say this. If I started a company today, Untuckit, I would go raise 500 grand, right? You'd go out, you have your marketing plan, you market, you ship all your shirts. If they're bad, it's over, right? Now it paid social, social media, all these people. Back then, luckily, we had no money. We had full-time jobs and we weren't marketing. So we learned all this. Okay, your shirts suck. Okay, we lost 600 customers. Keep their names, though, because one day I'm gonna send you a letter and explain that I agree our shirts were terrible and I want to send you a new one on us, which, by the way, we did that.

• 43:16Speaker 01

  The only reason we survived is because those years, we were so small. So we were able to perfect the shirt before we became known. That's what allowed us to go.

• 43:26Guy Raz?

  Right.

• 43:26Speaker 01

  And by the way, that was across, one of the reasons I think Aaron and I were successful is we did things completely different than they did in fashion. We didn't know what we were doing and we used that to our advantage. Like, you launch spring, everyone launches spring on March 1st, but it's 30 degrees. Why do they launch spring on March 1st? I guess because they've been doing it for 100 years. You know, it's snowing out and they're showing past that. So we were very comfortable with, we are not just following this blueprint of fashion. Right? We're gonna create our own way. And if it works, it works, and it's gonna work because of that, and if it doesn't, it doesn't.

• 44:00Guy Raz?

  You had no office, right? The office was your apartment in Hoboken, is it right?

• 44:06Speaker 01

  Yep. It was, and we did that for a long, we probably did that till 2015. We were very frugal. That was my plan. I didn't want to fall into the trap of many entrepreneurs of looking to get this big office, hiring all these people.

• 44:20Guy Raz?

  Yep. So you're doing half a million by year three and all online, all direct-to-consumer sales. Three years in, you're talking about 2013. So you didn't need to raise any more money at that point. You were still able to kind of take the, just operate the business through cash flow. But I imagine as the demand increased, you know, you had to order more stuff. So how are you handling the money? Were you getting loans? Were you?

• 44:47Speaker 01

  Well, what happened in 14, no, we had a line of credit, a little bit, a small line of credit. But what happened in 14 was we said, we can't keep going like this. We'll be here forever, you know, growing slow and let's go market. We gotta market. We had 21 grand to spend in marketing. And we called Boomer and Carton, New York radio show, only one we could afford.

• 45:09Guy Raz?

  It's a sports show, right?

• 45:10Speaker 01

  It's a sports radio show. They said you need like three months and a hundred grand to see results. And we said, we have three weeks and 21 grand. So we did it and I remember sitting in LA in a hotel room, first read comes out, I have my Google Analytics up. And within, now people are driving, they shouldn't be going to the site, but within 20 seconds, there's a thousand people on the site.

• 45:31Guy Raz?

  Wow.

• 45:32Speaker 01

  And sales going up, sales going up.

• 45:34Guy Raz?

  And they read the ad?

• 45:35Speaker 01

  Yeah.

• 45:35Guy Raz?

  And were they like, hey dude, do you ever have that problem where you like want to wear a shirt untucked, but it looks so stupid? And, and the other guy was like, yeah, I hate that. It's annoying. Well, now there's a, was it like that?

• 45:45Speaker 01

  Exactly, back and forth. And it would, and it would end very strong. Shirts designed to be worn untucked, untuckit.com. And people were like, must have been, what the heck is this? You know, because the people would just fly to the site. And then we booked airline and magazines, spent 15, made 45, and we could track this very closely because we weren't that big.

• 46:04Guy Raz?

  You spent $15,000 on airline magazines?

• 46:07Speaker 01

  Yep.

• 46:08Guy Raz?

  Okay, let's just pause there for a sec because I actually think that's a brilliant idea. And sadly, they don't exist anymore. Most airlines don't, don't produce magazines anymore. But what airline was it? Was it?

• 46:19Speaker 01

  It was everyone. We did Delta, United, Southwest. We were everywhere. And the only competitors in that magazine at the time were watch companies and fragrance companies. So when people saw us in there, I think they thought, oh my gosh, this company must be taken off. Which by the way, that opinion from a consumer makes them convert when they feel that you're bigger than you are.

• 46:38Guy Raz?

  And you're targeting guys like you, like sort of 20 to 50 year old guys initially?

• 46:45Speaker 01

  When I launched the company, I thought we were going to be fashion forward 20 to 40 guys who are actually going to take the time and say, oh, I also have that problem. It ended up being our current demo today, and it's fluctuated over the years, but it's 25 to 70 years old, evenly distributed. So pretty much every type of guy, rich, poor, you know, taxi drivers, Leonardo DiCaprio, Matthew McConaughey, to athletes, to construction workers, security guards. That's been why we became who we were.

• 47:14Guy Raz?

  Well, that's the thing, like forever and ever, wearing a shirt untucked was seemed sloppy. It was like, who does that, right? And there was a shift, right, that began around this time, where you started to see people, you know, wearing untucked shirts, or you saw a lot of people who were wearing blazers, jackets over untucked shirts that didn't look stupid.

• 47:39Speaker 01

  No, I mean, I love this, I say this not arrogantly, but there's no question we played a role into the casualization of the United States. I mean, it's not, we, you could wear our shirt into La Bernardin in New York City, La Bernardin being one of the, you know, the nicer restaurants.

• 47:54Guy Raz?

  Initial and three-star, yeah, one of the greatest restaurants in America, yeah.

• 47:57Speaker 01

  You could wear it with a sports jacket, and no one is saying, I can't believe that guy's shirt's untucked, right? And that's what we started seeing. Guys were wearing our shirts everywhere, and people weren't looking at them being sloppy. Fast forward today, now all these golf clubs across America, in their guidelines, say, you can only wear an untuck-it shirt, you know, when you're in the clubhouse, you know, if they allow shirts. So it started to become acceptable to wear our shirt to work, to wear our shirt to nice restaurants, weddings, whatever it may be.

• 48:27Guy Raz?

  Okay, so you guys are growing steadily over the first three years, and then the real breakthrough is when you have some money to go on this, the Boomer Esiason Show. And I imagine that you picked that show very specifically because it was guys, it was gonna be guys listening to sports radio, and that's who you thought, hey, this is, this is, this is gonna be our target audience.

• 48:52Speaker 01

  Yeah, sports to this day has become one of our main areas, whether it was the Masters or Sunday Night Football. So we started there. And by the way, then we went to Howard Stern very soon after that.

• 49:02Guy Raz?

  How did you, how did you afford that? I mean, that's a massive ad buy.

• 49:07Speaker 01

  So keep in mind, we raised about a million, three, call it, right? That's not exact, but.

• 49:14Guy Raz?

  Mostly from friends and family, not professional investors?

• 49:16Speaker 01

  No, all friends and family and doing about 53 million. Now, the equivalent, I'm not going to name brands was, had raised about 200 million. The only reason we were able to do that is because if we, and the reason you say about Stern, we weren't even nervous. If we spent on Stern, it returned. If we spent on Sunday Night Football, it returned. It always returned. This is back then, by the way. Everything's obviously more challenging today.

• 49:40Guy Raz?

  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?

• 49:52Speaker 01

  Back then, we were big testers. Test it, move on. Test, move on. Podcast 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. We, 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, it wasn't, you got to think about this. It was almost like, it wasn't a, a clothing brand. It was a concept.

• 50:27Guy Raz?

  Yeah. Let, let's, let me ask you about the name. Um, I think it works great. It tells you exactly what it is, what it does. You don't have to explain it. It's one word, untuck it. But there were people who were like, that's a stupid name. Give it a nut, like, you have an Italian last name. Give it, give it your last name. It'll sound Italian and kind of, you know, Italian fashion and premium.

• 50:52Speaker 01

  Yeah, we had, most people hated the name. I came up with it walking out in my, front of my parents' uh shore house and I had not launched the brand or even started it and I said, that is why I'm doing it. Because I came up with that name, I'm going forward with this. Because I love it. Untuckit. Like Untuckit is the reason we took off. I really believe that. And by the way, the reason, it wasn't sophisticated. That's what people would say and they're gonna think that the product isn't great.

• 51:18Guy Raz?

  Right, that it's like, right.

• 51:19Speaker 01

  And that is, that is the reason I said, we've got to make the greatest shirt you've ever worn. It's gotta be perfect. It's, you gotta, because you're, when you open that box, your mindset's gonna be, this isn't a super high quality product, because it's a gimmick, right? That's what, that was my fear. So I needed you right away to say, wow, this is an amazing shirt and it washes well and it holds up because of the name. That was the negative of the name. The positive of the name is now, if anyone's wearing an Untuckit shirt, people call it an Untuckit, period. They just, you know, it's like a Kleenex and a tissue and a Xerox machine.

• 51:51Guy Raz?

  Yeah.

• 51:52Speaker 01

  Um, and that, that's, that's a great moment as a brand. And by the way, it annoyed so many people in fashion, which is...

• 51:58Guy Raz?

  Right. No, I get why they'd be annoyed, because you're not cool, you're not part of that crowd, right? And there's a, there's a snobby kind of elite factor there. Like, they're not gonna invite you to fashion, to the Fashion Week runways, necessarily.

• 52:11Speaker 01

  And they intentionally didn't, all those years. Like, GQ wouldn't write about us and stuff like that, because they were annoyed that, you know, a non-fashion guy came up with this name that's, you know, not fashion-y and, you know, people liked it.

• 52:25Guy Raz?

  So the, really, the, the, the, kind of the turning point really was starting to do these ads and then Stern and then airline magazines and, I mean, with just a million dollars raised, you're five years in and you've, you're still working for GE, I think, at that point, right? You still are actually on the clock with them. And also, um...

• 52:49Guy Raz?

  How are you just coping personally? I mean, running a startup is a full-time plus job. It's a, it can be 100 hours a week. And you were still, even when you hit three, four million dollars in sales, you were still nervous. You still, you still mitigated the risk and held on to your job because you're still worried that this could all unravel.

• 53:11Speaker 01

  Oh, my gosh, it was so hard giving up that job. I had a car, I had a job, you know, like you had your parents, you know, say your wife, you know, you're gonna leave, you're like, I was scared to say, okay, I officially don't have a job. I am now an Untuckit employee.

• 53:24Guy Raz?

  Yeah.

• 53:24Speaker 01

  The worst part was my, it got bad at GE where it would bother me. It started bothering me that I'd say most people didn't like me. Now, by the way, they didn't like me, not because I was a bad guy. They didn't like me because I wasn't doing the, I wasn't going the extra yard, doing a quote, right? I was leaning on people. I was, I wouldn't go to the meeting because I was now, like you said, I mean, I'm, I have a business now that, by the way, is not doing a lot. It was doing, I could think exactly during that period of time, let's say it was doing seven million, six million. And I was like, but there's a chance here. So I left in 2015 and I was flying to our sales meeting, which I did not have time for because Untuckit was now really, really taking that next level. And in the magazine was a big picture of me, shirts designed to be worn untucked,

• 54:08Speaker 01

  you know, founded by Christopher Cabano. And when I got there, I guess all the people saw it on the way to Phoenix, to the sales meeting.

• 54:16Guy Raz?

  They were on the plane, they saw you in the airline magazine, your face.

• 54:20Speaker 01

  Yeah. And my boss came up to me, who I had a good relationship with him, not the people above him. And he said, I think it, I think it's time, Chris. This is gonna be a tough one to explain. That was very scary to me and I, I waited to the, I got pushed out. Like it was, you're forcing me out of here. And it got to the point, I never forget, I was walking to Dunkin' Donuts, like I do every morning, and I said, and it hit me really hard. I said, this business has to succeed now. I'm 30 years, if this doesn't succeed, I'm married and I'm like, I have nothing.

• 54:54Guy Raz?

  When we come back in just a moment, Untuckit grows to the point where it's about to be sold for a huge pile of money until all of its suitors pack up and go home. Stay with us. I'm Guy Raz and you're listening to How I Built This.

• 55:18Speaker 04

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• 55:53Guy Raz?

  Hey, welcome back to How I Built This. I'm Guy Raz. So it's around 2015, 2016, a time when two really important things happened for Chris. The first is he walks away from his GE job for good. And the second is Untuckit opens its first brick and mortar store in SoHo in New York City.

• 56:15Speaker 01

  I worked every day on the floor. And we, I saw this reaction to people that this was something special, this brand. I was able to pay myself a small salary and I felt really good. Now, you know, it's funny. I actually thought, okay, if this doesn't work out, I think I could go get a job in fashion at least. I could maybe go get a job as a...

• 56:35Guy Raz?

  No, at this point, yeah.

• 56:35Speaker 01

  Yeah, that was the big thing, that I could fall back and now become, you know, an operator in fashion of some sort.

• 56:41Guy Raz?

  Because you now understood the language. You could speak the language. You understood how the industry worked a lot better. I mean, now you're probably almost as much of an expert on shirts and apparel than you were in wine.

• 56:55Speaker 01

  Right, but I also felt pretty confident at the time. That store did so well in SoHo that one year, in three months, that I said, we're now going to open this. That's another X million of dollars in revenue. We're going to open five more. And then we opened 90 stores in, I think, two and a half years.

• 57:10Guy Raz?

  Wow, but I'm curious, in 2015, 2016...

• 57:15Guy Raz?

  You know, most brands are starting to move online, right? So, so why did you guys decide to open up physical stores?

• 57:22Speaker 01

  The reason I went into brick and mortar was because people always say, why did we do it back then? Even though all these people were yelling and screaming about it going away, I had 70% of my emails where I'm not buying you until I touch and feel your product. Part of that was because of our older demo, but we had to do it. It wasn't a, if we wanted to be around and exist, we had to open a store. I, that's when I started hiring more people.

• 57:45Guy Raz?

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

• 57:55Speaker 01

  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 UNTUCKit 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, they're 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 15 million, we quickly hired. Like, that's where it turned on quick.

• 58:35Guy Raz?

  Wow. Uh, let's step back because you officially launched a store in Soho. It's doing great. And, you know, I think the next year, finally, Aaron, your co-founder or partner, you bring him on to be the full-time CEO. I'm assuming you're just like, I'm done. I don't want to be doing the CEO job. I want to move to another role focusing more on maybe like product and creative and other things.

• 59:01Speaker 01

  To be honest with you, I recognize that he had a better history to be a CEO. You know, as a partner at PWC, that would give him a lot more credibility when we were going to have to eventually do a big fundraiser, sell the business. I wanted him sitting there as a CEO. But I, I wanted, I thought that was, and I think it ended up being a great decision. It just made, made sense to the business.

• 59:24Guy Raz?

  And you probably didn't have any management training, right? I mean, management is a skill that is developed through training largely. It's very rare when someone's just a natural manager.

• 59:33Speaker 01

  I agree, and I am not. You know, I kind of, if you think about it, one of the reasons I left corporate America was to be alone, that's gonna sound weird, was to be alone, working hard, right? I told you, I didn't like feel comfortable in those PowerPoint presentations, in those cocktail hours, in those smooth, like, I just liked to be working, you know, so it was never my, it's funny, like, Aaron's does most of the talking in those scenarios, because I, he's just better at it. He kind of went through that pathway to his career.

• 1:00:04Guy Raz?

  Let me talk about, about ads and marketing for a moment, because one of your ads is a, it's an ad of you walking through Soho, and it's, you're very serious, and of course, you're wearing an untucked shirt, and you're saying, "I had a problem, and then I solved the problem." And I don't think I need to tell you, 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, 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.

• 1:00:43Speaker 01

  It's, it was in, so I have Letterman and Seinfeld, Seinfeld, you know, saying, "I just hate that untucked 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 Kimo 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?"

• 1:01:26Guy Raz?

  All right, it's 2017. Up until that point, you, you could not actually get any professional

• 1:01:34Guy Raz?

  VC money. And this is a time, I should mention, we've done these on this show, we've done Stitch Fix, we've done Bonobos, we've done many of the brands that you've mentioned, but also just apparel brands too, that did were able to attract money from outside investors. Tell me a little about before 2017, trying to, I mean, how hard did you try to get money from venture capital firms?

• 1:02:00Speaker 01

  We were able to grow without raising money, which was very odd. So we were trying to avoid it at all costs.

• 1:02:07Guy Raz?

  I see.

• 1:02:08Speaker 01

  You know, I look back, I don't know how it was possible that we opened up 30, 25 stores without having raised money from that initial fundraise. It really was just refunding the business. And we took some, we took some debt. We did take some debt.

• 1:02:23Guy Raz?

  Yeah.

• 1:02:24Speaker 01

  Our first big fundraise was, we went out in 2016 to venture growth funds and Kleiner Perkins, they do not invest in untuck it type companies. I mean, they invest in Uber, you know, billion, billion dollar tech companies, right? That's what, and they were looking at us more like a marketing tech company than apparel company. And they, I'll never forget, they said, the reason they invested is that they thought we'd be the next great American brand. I just never forget that. We raised $8 million from them. That's, that's all we put on to bring us to our, what would have been our sale in 2020. We would have had $8 million raised, $9 million lifetime. So I thought that was pretty cool.

• 1:03:10Guy Raz?

  So Kleiner Perkins put in, you said eight million?

• 1:03:12Speaker 01

  Yeah, a little, they put in more, but it was secondary, you know, went to shareholders.

• 1:03:16Guy Raz?

  But in 2017, I think you raised a total of $30 million. Is that right?

• 1:03:21Speaker 01

  From Kleiner, yeah, from Kleiner. Eight went on the books.

• 1:03:24Guy Raz?

  I see. Okay. So essentially you were able to take some money off the table for the first time?

• 1:03:29Speaker 01

  Yeah.

• 1:03:30Guy Raz?

  So you had worked up until that point, but you presumably wanted some security at that point because you had been grinding and always nervous about whether this was going to go under. And finally, you could take some cash off the table, put it away for a rainy day in case it all went haywire.

• 1:03:48Speaker 01

  Yep.

• 1:03:48Guy Raz?

  So that must've been pretty great to be able to do that.

• 1:03:52Speaker 01

  It was a deep sigh of relief. I mean, it was one of those. You know, there were moments that you don't forget, but it was more not because of the money. It was more of the achievement. Wow, this, this really happened. I got something out of this. I got something. I started this, you know, silly idea and I was able to monetize it and say that it worked.

• 1:04:11Guy Raz?

  All right. And now they were a minority investor, minority owner.

• 1:04:14Speaker 01

  Yep.

• 1:04:15Guy Raz?

  All right. By the time, you know, Klaunert Perkins is putting money into the brand and you're hitting, you know, 50 million a year and you're starting to really build out stores, you know, the other established apparel brands, especially men's apparel brands, clearly have noticed you. In the first couple of years, they had no idea who you were, didn't care. Now you're starting to see, you know, the, the Brooks Brothers of the world and the Vineyard Vines and some other brands start to make untucked dress shirts.

• 1:04:45Speaker 01

  It's funny. A lot of times people ask me, what's been the greatest moment that kind of sticks out for you? And it was the day, which you think it would have been a depressing day, but the day that it clicked, that every single competitor, Vineyard Vines, J Crew, Banana Republic, just go on, everyone, led their 2019 spring campaign with shirts meant to be worn untucked. Now, two of them led with, two of the big ones led with shirts designed to be worn untucked. And we, we had to make them remove that, but everyone, I mean, Vineyard Vines set up a section in their store. They're known to be tucked in shirts more than any brand you've ever had, right? Like shirts that are preppy and tucked in. They had a untucked section in their store.

• 1:05:26Speaker 01

  It was, it was kind of a feeling of accomplishment that I started this kind of little idea to Hoboken. And now the whole fashion world, the whole, those billion dollar brands that have been around forever, are now changing their strategy because of us. And I think it's your even more attention to the untucked shirt. And what more do you want when your name's untuck it, right? So it ended up propelling us in 19, you know, to having, you know, our best year we had ever had by a long shot.

• 1:05:54Guy Raz?

  At this point, you guys are going beyond shirts. I mean, you're doing, you're starting to get into other parts of the apparel world, right? And today, of course, you do sport coats and trousers and, uh, you know, all kinds of things. And you've got, um, you know, clothing for women, but you know, by any account, you're a really successful, growing.

• 1:06:18Guy Raz?

  Player here and you know, you're on par at this time, or maybe even more so that with the bonobos and the, you know, the stitch fixes and you know, these big brands that are really kind of emerging in apparel. And there is talk about an acquisition, right? This is about what 2019, you start to talk about.

• 1:06:39Speaker 01

  Yeah, late 2019.

• 1:06:41Guy Raz?

  2019, okay. And tell me the story about the acquisition. Who was the acquirer? What's the story? How does it start?

• 1:06:48Speaker 01

  So we just decided in late 2019, we were growing so fast and we had so much growth ahead of us. We went into England. We had been doing very well in Canada. We had expansion plans across Europe and we had a growing women's brand with zero marketing. We had a growing pants brand with zero marketing, all these amazing things. And we just decided to go test the waters and we had 15 letter of intents coming in, you know, at a very, very big number.

• 1:07:15Guy Raz?

  You decided to test the waters just because you, this was a good opportu time. You felt like, okay. And I should mention, the first couple of years, you were profitable, but you were small. Now that you're growing and you're investing in growth, you are no longer profitable, which is normal. But now you felt like, okay, this is maybe an opportunity to get acquired by a bigger brand, you know, one of these big conglomerates or something, because now then they can take it to the next level.

• 1:07:41Speaker 01

  Yeah, and there's two things I've always wanted with this. I wanted one, to make good money and two, I wanted this to be a brand that way outlives me. That's very important. I wanted, you know, this to be a brand that's here for the next 50, 60 years, right? Or whatever.

• 1:07:53Guy Raz?

  By the way, I want to thank you for saying I wanted to make money because too many entrepreneurs come on the show and they don't say that. And I think that's disingenuous. I don't think there's anything wrong with saying, I did this to make money. I wanted to make money. So many people say, you know, money wasn't really an issue, it was about the mission or it was about the community. And I'm just like, come on.

• 1:08:13Speaker 01

  Yeah, for me, it's not, it's not, the money is not only because of the money. The money is because to me, that's the, if this were to end right now and someone sees me next week and say, congratulations, Chris. You did an amazing thing on Tuckit. I would be like, I didn't really, I never really like so that much sale with the money is like, I did it. I built a brand and I sold it for a lot of money. Like that's, that's what I say about the money, but, um, but also I do want the brand. And the reason I say that is I really believe that this is going to be a billion dollar brand. I still do.

• 1:08:46Guy Raz?

  You, so you guys went and worked for the bank and put sort of hung your shingle out there and you had 17 letters of intent.

• 1:08:53Speaker 01

  Fifteen.

• 1:08:54Guy Raz?

  Potential fifteen.

• 1:08:55Speaker 01

  About fifteen and, and we knew the number that we were requiring, which was a very big number. So.

• 1:09:01Guy Raz?

  Over a billion dollars?

• 1:09:03Speaker 01

  No, close to it. You know, north is probably north of seven 50, somewhere around there. You know, you probably have an outlier. You probably have a real low one, right? It's all.

• 1:09:11Guy Raz?

  And not, not an unrealistic number with so many letters of intent because you could get into a bidding war.

• 1:09:16Speaker 01

  So basically in my mind, I'm there. I mean, I'm sitting there, you know, weeks away, you know, I'm, I'm dreaming of the coast of, of France and, and I was like, it was, it was real, you know, I was, um, and you know, I bought it. If it was done a little earlier, we shut it down because of COVID, obviously.

• 1:09:34Guy Raz?

  Who shut it down?

• 1:09:36Speaker 01

  Everyone like we're, everyone reached out to us, you know, we're not going to do a deal like it's.

• 1:09:41Guy Raz?

  All of the potential acquirers pull out.

• 1:09:43Speaker 01

  Yeah. Or, or I don't know if it was pulled out. I can't, it was more of a, we're not giving you our letter of intent right now. We're, the world is closed.

• 1:09:49Guy Raz?

  We're going to take some time. Okay.

• 1:09:51Speaker 01

  Yeah. I think it's shut. What, when did it shut down? March?

• 1:09:53Guy Raz?

  It was in March. It was in March of 2020. So, so, so these, all of a sudden, all of these potential acquirers are like, we're going to just, we're going to take a beat here because we, we don't know what's going to happen.

• 1:10:04Speaker 01

  Right.

• 1:10:05Guy Raz?

  But you were that close to maybe getting acquired for three quarters of a billion dollars.

• 1:10:10Speaker 01

  I mean, so close. And I owned, by the way, a lot of the company because we. When Kleiner put on eight million, they were very adamant, our main investor, to say, this company's doing well. Do not dilute. Like, let's just raise with debt. So we took on debt because we, we had a plan. But we had very little cash, you know, in comparison to what you need going through COVID. So that, so the bad news was that was shut down. The worst news was that, you know, now all of a sudden you're scrambling, you know, what's our accounts payable? What's our debt? What's this? We are, our numbers, sales numbers are starting to drop significantly. But the biggest thing is, I realized, okay, we have some significant cash issues here. And they're happening fast, right? Like, because, okay, now they're closing our stores.

• 1:10:55Speaker 01

  Well, that's, um, you know, it's a big number, big numbers a month.

• 1:11:00Guy Raz?

  What did you see, like, percentage decline from March to April of 2020? You remember, like, more than 20%, 30%?

• 1:11:08Speaker 01

  Probably like 40, 50%.

• 1:11:11Guy Raz?

  Just drops.

• 1:11:12Speaker 01

  Yeah, because it was as, so we would get, my investor would call us and say, I don't understand. Everyone else is doing good online. And we're like, you don't understand, because everyone's buying Viori, right? Everyone's buying non, and by the way, I'm still doing decent amount of revenue with non-shirts. The problem is, when you have, you know, 40, 50, 60 million less than revenue, you're, you're, it's, the math is very simple. You run out of money. So we got on the phone with a bankruptcy attorney, and he's like, you have to declare bankruptcy. You're the, you, you, this is why bankruptcy exists.

• 1:11:45Guy Raz?

  Your lawyer's saying this in when? In March?

• 1:11:47Speaker 01

  This is April. April.

• 1:11:49Guy Raz?

  Wait, how much debt did you have, by the way? Like, tens of millions, hundreds of millions?

• 1:11:54Speaker 01

  Yeah, no, we had like 30, 40 million, but that wasn't the point.

• 1:11:56Guy Raz?

  And because you had...

• 1:11:57Speaker 01

  You couldn't get new debt. So my, that, that's the bigger...

• 1:12:00Guy Raz?

  Ah, okay.

• 1:12:01Speaker 01

  You couldn't go get money.

• 1:12:02Guy Raz?

  Because you had 30 million in debt, you couldn't get money. And your lawyer, even though you had this national brand and what, 90 stores, your lawyer was saying to you, you got to declare bankruptcy.

• 1:12:13Speaker 01

  Didn't matter because our, so we had to pay our... Monthly payment to the stores.

• 1:12:19Guy Raz?

  The lease, right, the rent, right?

• 1:12:21Speaker 01

  We had to pay that number. We had to pay all of our employees.

• 1:12:24Guy Raz?

  Probably 20, 30 grand a month in rent, maybe more.

• 1:12:27Speaker 01

  It's a lot of money. And then we had to pay all of our employees. We had just grown too fast, too many employees, paying 90, 90 stores, a big office, all these things that we needed our money to be coming in. And by the way, our factory accounts payable was huge because we were bringing in product for that year that was going to allow us to do massive volume. We had already ordered it and we had to tell them we can't take the product. And they're like, well, you owe us $30 million or whatever the number is.

• 1:12:54Guy Raz?

  Woo.

• 1:12:55Speaker 01

  So the guy, I said, what is bankruptcy? You know, what do you, what is, of course, everyone knows high level, what is bankruptcy? I mean, I didn't know that, you know, oh, bankruptcy, what is it? We, you know what, I probably keep most of my equity. We kind of, and then we'll just re, they're like, well, you own nothing, zero, and you're not going to get paid a dime because they're going to kick you right out. And, you know, there's going to be, with us, there'd be a bidding war. So it's even more painful.

• 1:13:20Guy Raz?

  Yeah. But why was your lawyer, I guess your lawyer was suggesting this.

• 1:13:23Speaker 01

  It wasn't my lawyer. It was a lawyer they brought on who was a bankruptcy lawyer, attorney.

• 1:13:27Guy Raz?

  I see. Okay. And he was saying, look, the only way to save the brand is to, and that meant that you wouldn't, you know, all this debt would go away, but then, and you could walk out of there having banked some money and, and.

• 1:13:40Speaker 01

  Very little, would have been very, very, very little. Like they would have, you know.

• 1:13:44Guy Raz?

  They'd gone after YouTube probably.

• 1:13:46Speaker 01

  Yeah, it would have been, wouldn't have been great.

• 1:13:48Guy Raz?

  I, I cannot imagine, even when that was brought up, because you're not a lawyer, you know, and, you know, most of us aren't lawyers. We don't, when a lawyer says that, I think a lot of people take it seriously. Like, okay, well, I gotta consider this.

• 1:14:01Speaker 01

  It was the hardest thing to, and but the problem is you're also dealing with this COVID stuff, which right in that period of time was scary for everyone, right? Like you're sitting, you know, you can't leave your house, you can't, and by the way, that's not a small thing. I don't mean to, everyone goes through, everyone went through something with COVID. So many businesses were lost. So I'm not the only one. It just so happens I was days away from selling it for such a big number. That's the only, you know, that it was that kind of super high to super low. So I got on the phone, my partner, we didn't really know what to say or do. I mean, you don't, you didn't know when COVID was going to end. That's the problem. That was what made this so bad. So we called our, uh,

• 1:14:43Speaker 01

  All of our landlords, one by one, we called all of our factories. Some were great, some we had threatened back and forth with lawsuits, this and that. Ninety percent of them said, we think you're going to be an unbelievable brand post COVID. We're going to hang with you no matter what. Well, so we, we built up this massive accounts payable. I don't want to say the number, just to survive. We raised some money at a very low valuation because you had to.

• 1:15:07Guy Raz?

  Did Kleiner put more money in during, during this crisis?

• 1:15:11Speaker 01

  They did.

• 1:15:12Guy Raz?

  They did. Okay, so they, and they probably got a good deal.

• 1:15:14Speaker 01

  They did get a good deal.

• 1:15:15Guy Raz?

  I cannot, I, I just cannot imagine the level of stress that you were under because first of all, you're dealing with just declining revenues. You've got to figure out a quick way to get cash infusion. And I believe that you guys had like three kids in quick succession around this time. Like over a three year period of time.

• 1:15:36Speaker 01

  During COVID, I had, I had four in, um, yeah, six years. Yeah, all that was happening, it was, um, it was, we were there, we made it to a point that it was now, you know, hanging by a thread. There's really only one person I could talk to about it was my partner because I didn't want to bring in my, my, my wife and my dad, I didn't want to get them nervous.

• 1:15:55Guy Raz?

  Talk to them, you don't want to talk to your wife or your dad about this?

• 1:15:58Speaker 01

  I didn't, it was, it was so bad, by the way, if, if the company went bankrupt, I couldn't, I don't want to give too much of my personal life, but I couldn't have afforded my, you know, I had just sold some of the company, I had built a house. And now it was, it was an ego hit, I hate to say it, it just was, you know, your company gets pulled from you.

• 1:16:18Guy Raz?

  Nothing, of course.

• 1:16:19Speaker 01

  It was a money hit because now you have no money. And by the way, you're not making money, you're not getting a job over COVID, like it's just hard. And you have four kids. It was crazy and it was not because of anything we did wrong. That's what bothered me about it. And there was no solution. You want to know why I didn't tell my wife and father? Because there was no solution.

• 1:16:40Guy Raz?

  Yeah, but you, you kind of start to emerge from COVID. And we've had stories like this on the show with other apparel brands where COVID ends and they're brands that weren't really fit for COVID, like they're really more. You know, things that you would wear outside to just look good. And then after COVID, they just explode and grow. And I imagine that once people start to emerge from COVID, not necessarily going back to work, but even going out, people started to buy the clothes again.

• 1:17:07Speaker 01

  They started buying the clothes again. Now, we had no cash, right? Because we're coming out. So we really didn't know what to expect. What happened was we did, we were able to take on some debt to get us through it. That's how we solved our bankruptcy problem. We solved some with cash and some with debt. We cut back inventory. We do good in 2023, our most profitable year ever in 23, not the growth year where we wanted it to be. Now, long story short, I want to make sure I'm very clear about this. Because so we solved the problem in 24, and we are now having a tremendous 25. And we are beginning our wholesale growth. And I can get into that in a second as the final phase. But we are, it just took four years.

• 1:17:50Speaker 01

  It was a four-year hamster wheel that we were in.

• 1:17:54Guy Raz?

  All right, so you, you recover from COVID and back now again to, are you guys getting close to profitability?

• 1:18:03Speaker 01

  No, we're profitable.

• 1:18:04Guy Raz?

  You are profitable, okay.

• 1:18:05Speaker 01

  We were profitable in 22, and we were significantly profitable in 23, even though the year wasn't what we wanted because we didn't market. And 24, we were profitable. And this, this year is an exciting year.

• 1:18:17Guy Raz?

  All right, you are now, I think, for the first time recently, have gone into wholesale, into Nordstrom, into Macy's, Stitch Fix and a few other places.

• 1:18:30Guy Raz?

  Tell me a little bit about that decision.

• 1:18:32Speaker 01

  Well, like I said, I want to be, I want to be a massive brand, you know, a brand that fits all demos, men's, fathers, sons, kids. You have to go into wholesale eventually. If you want to scale to that level, to a billion-dollar brand, you know, we're opening in Mexico City later in the year. Like, just so many exciting things. So that's the one area that is low-hanging fruit, because customers want us, we know that. So they're going to want us where they shop. And that's a huge opportunity. And it's definitely part of the long-term plan. So I can get back to north of where we were, you know, in COVID, pre-COVID.

• 1:19:08Guy Raz?

  Um, you know, I'm wondering now, I mean, here you've gone, been through certainly trial by fire, a lot of highs and a lot of lows in building this brand over since 2010. Here you are now, almost 15 years into this thing. You're obviously super experienced. How do you see your own role playing out? I mean, I guess, I imagine that at some point you'd like to hopefully try to see if you could get acquired again, maybe, right? Or, I don't know, maybe go public, which is risky too. But I imagine there's a point at which you do exit this thing.

• 1:19:51Speaker 01

  Yeah, no, I will definitely want to get acquired and sell and kind of make this an ultimate. Now it's become, I need this now to get over this, you know? You don't want to be the person who's going to sell for something and then sell for nothing or sell. So now it's like I'm back in that, listen, I'm more stressed now than I was ever. There was this little period of time in 19 and 20 when I wasn't because I need this to happen. I'm, you know, I am, these three years have been very draining and, you know, and as Aaron would say the same thing, like, we have to see this through. But I'll tell you that any deal that I do, I'll still be here, you know, helping grow. I do believe, when I say I think this can be an international brand, I really believe it can. I want to be there for it.

• 1:20:36Speaker 01

  I don't want to, you know, not be there for some of that exciting parts of it.

• 1:20:39Guy Raz?

  Chris, given where you are now, I mean, you even admit that when you started this idea, it was a one in a million chance of working, of succeeding, because apparel's hard. It's really hard to build an apparel brand. But it did, it did succeed. And I wonder how much of where you got to now, where you are now, when you reflect on it, how much do you attribute to the work you put in, the grind, and how much do you think had to do with luck?

• 1:21:05Speaker 01

  So I'm a big believer, I'm not someone who denies luck. Luck is so important in every area of life. There's not one successful person who didn't get luck. I think there's a massive amount of luck. I say luck because I launched it at a period of time where I think it allowed me to make mistakes and to still take advantage of paid social. You can make an argument that isn't luck, that's strategy, that or whatever, but I think it's a blend. I think there's no question. The hard work, my vision and pushing through and just doing it. I would say just doing it. How many people just don't do things, right? That's, it's crazy. I mean, you know, it's, uh, it's draining to be an entrepreneur, I guess is all I can say. But I think it's a mix of luck and a mix of hard work. You need both.

• 1:21:51Guy Raz?

  That's Chris Riccobono, co-founder of Untuckit. And by the way, remember Chris's wine vlog, Pardon That Vine? He stopped doing it years ago, but the videos are still up on his YouTube channel. And in the last one he posted way back in 2012, Chris is reviewing a Syrah from New Zealand. And what he's wearing? An early version of an Untuckit button down shirt.

• 1:22:16Guy Raz?

  Hey, thanks so much for listening to the show this week. Please make sure to click the follow button on your podcast app so you never miss a new episode of the show and sign up for my newsletter at guyraz.com or on Substack. This episode was produced by J.C. Howard with music composed by Ramtin Arablouei. It was edited by Neva Grant with research help from Kerry Thompson. Our audio engineers were Patrick Murray and Robert Rodriguez. Our production staff also includes Catherine Seifer, Carla Estevez, Casey Herman, Sam Paulson, Alex Chung, Andrea Bruce, and Elaine Coats. I'm Guy Raz and you've been listening to How I Built This.