How I Built This with Guy Raz - UNTUCKit: Chris Riccobono

Episode Date: June 23, 2025

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 & Instagram, and email us at [e-mail]. Sign up for Guy's free newsletter at guyraz.com and on Substack.See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

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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, uh, but you know what's funny? You know what's funny? I didn't, 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. Welcome to How I Built This, a show about innovators, entrepreneurs, idealists, and the stories behind. the movements they built. I'm Guy Raz, and on the show today, how a guy who knew nothing about shirts rolled up his sleeves and started untuck it, a brand that seemed like a gimmick until it started a trend. 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 purse.

on their sleeve. Fresh pet, butcher box, paperless post. You know exactly what you're getting. And that's the direction Chris Rickabono went with his company, Untuck It. 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. 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 Untuck it was just the start. To get past the gimmick, the shirts had to be good. Chris and his co-founder, Aaron San Andrus, 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.

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 on Tucket on the side. The business was eventually doing so well at work. one point that it was almost acquired for about three quarters of a billion dollars. That is, until the deal fell apart and almost tanked the entire company. But today, Untuck It is once again thriving, over 80 stores, a growing wholesale business, and a fast-growing women's line. And Chris Rickabono? 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. 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 and interviews. My first interview I ever did at Providence, the guy stopped the interview because he could hear my heart beating. Literally, 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. That just wasn't my thing. I knew I wasn't good at it. You knew that you would get to a company. And because I think it was for, you would eventually work for General Electric for quite a while.

Yeah. 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 charm, maybe charismatic. You didn't have like. I just couldn't do it. And I knew it, brother, right when I started with G. 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. While you were at GE, you already knew, because you would spend how many years total would you spend there? Probably 10. But you knew already early on that you were not going to really climb up the ladder there. Yeah, just I couldn't get excited about selling medical equipment. I guess that's what it was.

I just didn't excite me. all these guys who I worked with, you know, and he had the 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. Got it.

Okay. So you're at GE, and I think a couple years in, you decide to do an MBA program at Columbia while you're at GE. So 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 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? No, it was very simple. 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 I'm 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. But you're still a GE. it's a steady job and it's a paycheck, basically. Exactly. Right?

And I think you were, I think you were already married at this time, right? I got married in 2009. Right. But to somebody you met in college as an undergraduate. Right. Right. Exactly. Who's still your wife today.

Yep. Okay. So 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 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 kind of trying to see which one would work. And I guess one of the first ones was a wine blog or vlog, video blog called Pardon That Vine, which was you would talk about wine.

We're going to get to it in a second. But tell me how that idea came about. Because I know around this time, I mean, I think a lot of people who know this world might think of like Gary Vaynerchuk. That was an early thing that he did. 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 going to 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 wasn't sure what I was going to do because I didn't, I was thinking, Gary's got a massive following.

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 bordeauxs lined up for me, and I would do the, they thought I was important back home. Little did they know 15 people watch the show. So, all right, so you decide to do this. First of all, you, you were into wine. It was just a thing you

were into. Yeah, that story is 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 of 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 wanted to be at a bar. I wanted to be. I said, fine, I'll come over to have dinner. And he says, go in a 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 us, 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 three more bottles are red and the storytelling.

And, you know, and I had an unbelievable night there, you know, and I said, wow, this is amazing. Like, this is, 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. All right. So you decide that this could be a cool venture, and you called it Pardon, Pardon that Vine. But tell me what was the business model. Was it going to be ad supported? How did you think you were going to make money from this thing? 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... YouTube was new, was very new, yeah. What could have happened to me, if I was better at it and maybe technology was a little better,

maybe the goal I would have been that first influencer, right? You know, it just never, I wasn't my thing. But I guess that was the build-up 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.

This was one of many ideas. I think there were other sort of more short-lived ideas. Like you had an idea for an online dating service for little people. Love for little people, L4LP. You actually registered domain. Yeah, I can't get away from this one. Yeah, L for LP with my cousin. 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. 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, 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 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. 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.

Yeah, and that's a fun, it's funny. All these things were happening before it became mainstream today. So 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.

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? 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. 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 the sales. I mean, I'm joking a little bit, but you know, 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 didn't have to go to the accounts and they still would buy for me. And that's what allowed me to last to cheese so long because as much as they wanted to get rid of me, they couldn't because I was hitting my number. but basically spending as much time as possible on this other project. And were you mainly like looking for value wines, like talking about wines that people could go buy at the, you know,

at the whatever total wine or whatever wine store they were going to, Costco? What I was trying to do was wine was very, the only word I have is like snobby back then. It's kind of changed. 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's how. 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. I mean, this is, it's interesting because 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? 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 around 2010. You're still a GE. You're still selling medical equipment. You're doing the wine vlog. How does this kind of light bulb go off in your head about an idea to make shirts?

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 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.

When you say out-spec, what do you mean by that? 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 measure 10 shirts from most companies in 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 of 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 the other ones did. Right. 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.

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. I wore the same shirt four nights in a row, became a big topic of conversation about everyone's struggle and I'm, you know, looking at my friends and how silly they look. And I said, I got to find a way to do this. You're wearing this J. Crew shirt that was, that you would wear untucked. Weren't 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.

Yeah. So basically, you guys are talking about this with your friends. And, uh, and you were like, hey, I want. a shirt that fits sort of like a well-fitted t-shirt, but that's a with a collar and button, a button down, basically. 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. There are guaya beras, for example. Well, that style shirt, yes, but that's not what we were making. You know, the oversized, you know, 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 untuck, these companies, 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. Because you're talking it in.

Because you're talking it in. 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. 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.

Are you 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. And 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 San Andreas, 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 us to 800 times. But he sits down and he said, I'm in. You don't have to tell me any further. I've had this problem since day one.

This is Aaron San Andreas, right? You had met him when you did your degree of Columbia, and he, I think, was working at Pricewaterhouse. PWC. Yep. He was a partner at Pricewater. Pricewater's group. So he was an accounting. He was someone similar to me in that he would also pitch ideas. We always wanted to think of ways to start a company. He's somebody that you – just tell him 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? He's just incredibly smart.

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. It 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. You didn't know about how to design a shirt. You're not a fashion guy. You didn't go to a 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? Well, you're right. Like I wanted to make sure. I went into the fashion district. I wandered in and out. I brought my 1J 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. You're talking about the garment district in New York City.

You actually went into garment makers and asked them if they could make you a custom shirt. Yeah, I wandered in the street and looked at places that have saw 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 going to 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 speck 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.

So the length, by the way, 28.75, that's my favorite number in the world. Inches. 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 two years to get to market, you know, to finally get that right shirt. But that, that's,

that was the hardest part is finding how. to make the shirt. All right. So already in year one, I mean, you're kind of doing this R&D. Aaron is working at Pricewaterhouse 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. 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 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. 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 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? No, it's not a good bet. It's not a good bet. Not at all. But before we get to the money side, just going back to what you and Aaron were doing, were both of you living in New York City at the time? I was living in, I had just moved to Hoboken,

and Aaron was living in New York City. So how often were you meeting? 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, 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. When we come back in just a moment, Chris and Aaron get a crash course in how not to make a shirt. Stay with us. I'm Guy Raz, and you're listening to How I Built This. 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. 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. 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 do, are you 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. If I was five years later, it wouldn't have worked out. I don't think the way it did. So this guy is a Polish guy in an office in New York, and he had his own factory in Poland

or he had connections to a factory? He was the broker for that factory in Poland. I got it. And that was going to be cost effective to do in Poland at the time. Yeah, it wasn't going to be the cheapest. I just had no other contact, you know, in Asia. And the shirts were going to be made out of cotton, I'm assuming. Yeah, it was all cotton, basic stuff.

How many shirts did you order in that first? Only a thousand. And how much did it cost you? Probably 20,000, somewhere around that. And you were going to sell them for like 30 bucks or something? No, no, we were more than that. I think we were like 78, 88. Okay.

So it was going to be a premium sort of premium shirt, right? 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. Wait, hold on.

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

I didn't, I thought we thought through it and said, you know what? We'll 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 going to, and I'm going to lose X amount of customers. I mean, you didn't have a choice. choice. This is entrepreneurialism. You just have to survive. You had to sell those shirts even though

they weren't. 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 shipped every night from my apartment. But we remained positive because when the guys got the shirts, the excitement. We 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, kept going. The next line that came out, we had, I got the first shirt. I'm measuring it out. I see a little thing on the button. I pull the button up and it falls off. I look at the next button.

The button falls off. 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. Take your shirt to the dry cleaner and get them put back on. By the way, these were all being made in that factory in Poland. They were all being made in a factory in Poland. And not to knock Poland because Poland, I mean, Poland today, I think, would be prohibitively expensive. It's an industrial power and it's got manufacturing and it's a EU country. But my obvious question is, why would you keep working with that factory if the shirts they were making sucked? First of all, you didn't have a choice. It's much harder than you think as a company making a thousand shirts or whatever the shirts we make. 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. I just trying to figure out, why is it so complicated? I mean, I'm wearing one of your shirts now. I wear lots of button down shirts. What's so hard? Why is it so hard?

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 can pull down most shirts an extra inch if you just give it a little tug. It shrinks, it moves, the heat effects at 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, 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 untucket, shirt, son, and you're, you're talking about this perfect length. It has to be perfect. 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. It depends now. There's some 3D technology and printing and stuff. But then you're saying it was still, there were humans with, you know, sewing machines and their hands,

and they were doing the hems and the, they were stitching, the stitches and everything. And that was, right. Now think about this. Like, if we're making 15,000 white medium shirts,

which we do, and they put them into a washer machine. They want 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. And your promise was, hey, it's going to look great as an untucked shirt. But if it was slightly off or it trunk too much or, you know, or it, the whole thing gets thrown off balance. And there's no difference. And then we blend in with everyone else. And the idea goes away. we disappear. 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. They were the only,

they were the only ones. Yeah, we had no choice and we quickly fixed our, I think that that's, and listen, this is now 14 years. But I do know we, so I don't have the exact timeline, but I do know we pivoted quickly and improved the shirts because they got really good in like, you know, this third year. How did you do that? I mean, did you, were you flying to Poland to that factory? at a certain point, imagine you stopped working with them. I stopped working on, but I also found this Swedish guy named Bjorn, who's still with me today. Older guy teaches at the Fashion Institute. How did you find him?

I was working with a freelance guy who was not very good. Bjorn walks in for a meeting with him, and he throws him the shirt, and he says, what do you think of this shirt, Bjorn? And Bjorn destroyed the shirts. It's 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 This is year 1,23 Yeah, then You know, 3,015 And up from there

So that 3 to 15 Was a big difference But the great thing was We always say this If I started a company today On Tucket, 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 we 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 going to 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. 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. 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 it. So we were very comfortable with, we are not just following this blueprint of fashion, right? We're going to create our own way. And if it works, it works. And it's going to work because of that.

And if it doesn't, it doesn't. You had no office, right? The office was your apartment in Hoboken. Is it right? Yep. It was, and we did that for a long. We probably did that until 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. Yeah. 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 or you Did you 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 got a market We had 21 grand to spend In marketing

And we called Boomer and Carton New York radio show The only one we could afford They said you need It's a sports show right It's a sports radio show They said you need

Like three months And 100 grand to see results. And we said we have three weeks and 21 grand. So we did it. And I remember sitting in L.A. 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. Wow. And sales going up. And they read the end. Yeah.

And were they like, hey, dude, do you ever have that problem where you want to wear a shirt untuck but looks so stupid? And the other guy was like, yeah, I hate that. It's annoying. Well, now there's a, was it. like that? Was it the absolute? Exactly, back and forth. And it would end, very strong. Shirts designed to be worn untucket.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 a magazine, spent 15 made 45. And we could track this very closely because we weren't that big. You spent $15,000 on airline magazines. Yeah. Okay, let's just pause their first sight because I actually think that's a brilliant idea. And sadly, they don't exist anymore. Most airlines don't produce magazines anymore. But what airline was it? It was everyone. The 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. And you're targeting

guys like you, like sort of 20 to 50-year-old guys. initially? 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, taxi drivers, Leonardo DiCaprio, Matthew McConaughey, to athletes to construction workers, security guards.

spin why we became who we were. 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 start 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. 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, you could wear our shirt into LaBerna Dan in New York City,

LeBerna Dan being one of the nicer restaurants. The restaurant. One of the greatest restaurants in America, yep. You could wear it with a sports jacket, and no one is saying, I can't believe that guy's shirts 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 untucket 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, nice restaurants, weddings, whatever it may be. 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 the Boomer Osceison show. And I imagine that you pick that, you pick that show very specifically because it was guys, it was going to be guys listening to sports radio. And that's who you thought, hey, this is, this is, this is, this is going to be our target audience. 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. How did you, how did you afford that? I mean, that's a massive ad buy. So keep in mind, we raised about a million three. call it, right? That's not exact, but... Mostly from friends and family, not professional investors. No, all friends and family and about 53 million. Now, the equivalent, I'm not going to name brands, 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. 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 should we go? Back then we were big testers. Test it, move on.

Test it. 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. 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 wasn't, you got to think about this. It was almost like,

it wasn't a clothing brand. It was a concept. Yeah. Let me ask you about the name. I think it works great. It tells you exactly what it is, what it does. You 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 your last name. It'll sound Italian and kind of, you know, Italian fashion and premium.

Yeah, we had, most people hated the name. I came up with it walking out in my front of my parents' shorehouse, 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. Untuck it. Like, untuck it 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 going to think that the product isn't great. Right, that it's like, right. And that is the reason I said, we've got to make the greatest shirt you've ever worn. It's got to be perfect. You got to, because when you open that box, your mindset's going to 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 untuck shirt, people call it an untuck it, period. It's like a Kleenex and a tissue and a Xerox machine. And that, that's a great moment as a brand. And by the way, it annoyed so many people in fashion, which is... Right. No, I get why they'd be annoyed because you're not cool, not part of that crowd, right? And there's a, there's a snobby kind of elite factor there. Like, they're not

going to invite you to fashion to the fashion week runways necessarily. 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-fashioned guy came up with this name that's, you know, not fashiony and, you know, people liked it. So that really 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're still working for GE, I think, at that point, right? You still are actually on the clock with them. And also, how are you just coping personally?

I mean, running a startup is a full-time plus job. It can be 100 hours a week. And you were still, even when you hit $3,4 million in sales, you were still nervous. You still mitigated the risk and held onto your job because you're still worried that this could all unravel. 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 going to lead.

Like, I was scared to say, okay, I officially don't have a job. I am now an untucket employee. Yeah. 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 going the extra yard doing a quote, right? I was leaning on people.

I wouldn't go to the meeting because I was now, like you said, I mean, I have a business now that, by the way, he's not doing a lot. It was doing, I could think exactly during that period of time. Let's say it was doing $7 million, $6 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 on Tucker was now really, really taking that next level. And in the magazine was a big picture of me. Shirts designed to be worn untucked, you know, founded by Chris Rickabono. And when I got there, I guess all the people saw it on the way to Phoenix to the sales meeting.

They were on the plane. They saw you in the airline magazine, your face. 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's time, Chris. It's going to be a tough one to explain. That was very scary to me. And 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. When we come back in just a moment, Untuck it 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. 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 happen for Chris. The first is he walks away from his GE job for good. And the second is Untucket opens its first brick and mortar store in Soho in New York City. 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 play 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, yeah. Yeah, that was the big thing that I could fall back and now become, you know, an operator in fashion of some sort. Because you now understood the language, you could speak the language,

which 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 on wine. 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.

Wow. But I'm curious, in 2015, 2016, you know, most brands are starting to move online, right? So why did you guys decide to open up physical stores? 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. If we wanted to be around and exist, we had to open a store.

That's when I started hiring more people. 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? 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 they're right up to the middle of the iron clip them hang them outside if they but we didn't hot we were very lean that's the 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 wow 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 and you're 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. To be honest with you, I recognize that he had a better history to be a CEO, you know, as a partner of PWC, that would give him a lot more credibility when we were going to have to eventually do a big fundraise or sell the business. I wanted him sitting there as a CEO. But I wanted, I thought that was, and I think it ended up being a great decision. It just made sense to the business. 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. 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 a long. That's going to 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 and those smooth. Like, I just like 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. He kind of went through that pathway to his career.

Let me talk about, about ads in marketing for a moment because one of your ads is a, it's an ad of you walking. through Soho and it's very serious and of course you're wearing an untucket 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. It's it was in, so I have Letterman 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 look 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? All right. It's 2017. Up until that point, you could not actually get any professional VC money. And this is a time I should mention. We've done these, on this show, we've done stitchfix, 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 bit about before 2017 trying to, I mean, how hard did you try to get money from venture capital firms?

We were able to grow without raising money, which was very odd. So we were trying to avoid it at all costs. I see. 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. Yeah. Our first big fundraise was, we went out in 2016 to venture growth funds and, and Kleiner Perkins, they do not invest in Untucket 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 a 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 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. So Kleiner Perkins put in, you said, 8 million? Yeah, they put in more, but it was secondary, you know, went to shareholders. But in 2017, I think you raised a total of $30 million. Is that right? Yeah, from Kleiner.

Eight went on the books. I see, okay. So essentially, you were able to take some money off the table for the first time. Yeah. So you had worked up until that point, but you presumably wanted some security at that point because you had been grinding and always. always nervous about whether this is going to go under. And finally, you could take some cash off the table and put it away for a rainy day in case it all went haywire.

Yep. So that must have been pretty great to be able to do that. It was a deep sigh. I mean, it was one of those, you know, the moments that you don't forget. And it was more not because of the money. It was more of the achievement. Wow, 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. All right. And now they were a minority investor, minority owner. Yep. All right. By the time, you know, Kleiner 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 Brooks brothers of the worlds and the Vineyard Vines and some other brands start to make untucked dress shirts. 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 to everyone, led their 2019 spring campaign with shirts meant to be worn untuck.

Now, two of them led with, two of the big ones led with shirts designed to be worn untucked, and we had to make them remove that. But everyone, I mean, Vineyard Vineyard Vineyard Vineyard-Vine 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. It was kind of a feeling of accomplishment that I started this kind of little idea out of Hoboken. and now the whole fashion world, the whole, the billion-dollar brins 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, having, you know, our best year we had ever had by a long shot. 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, you know, all kinds of things. And you've got, you know, clothing for women. But, you know, by any account, you're a really successful, growing player here. And, you know, you're on par at this time, or maybe even more so 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 maybe. Yeah, late 2019. 2019, okay. And tell me the story about the acquisition. Who would the acquire?

What's the story? How does it start? 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. You decided to test the waters just because you, this was a good opportunity 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. 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, just to be a brand that's here for the next 50, 60 years, right? Or whatever that works. 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 was about the community. And I'm just like, come on. 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 said, congratulations, Chris, you did an amazing thing on Tucket. I would be like, I didn't really. I never really. 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 what I say about the money. 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. 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. 15. Potentially. 15. About 15. And we knew the number that we were requiring, which was a very big number. Over a billion dollars? No, close to it. You know, north is probably north of 750, somewhere around there. You know, you probably have an outlier. You probably have a real low one, right? It's all. And not an unrealistic number with so many letters of intent because you could get into a bidding war.

So basically in my mind, I'm there. I mean, I'm sitting there, you know, weeks away. You know, I'm dreaming of the coast of France. And I was, like, it was, it was real. You know, I was, and, you know, I bought it. If it was done a little earlier, we shut it down because of COVID, obviously. Who shut it down? Everyone, like, we're, everyone reached out to us, you know, we're not going to do a deal. Like, it's, you can't do a deal. All of the potential acquires pull out.

Yeah. 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. The world is closed. We're going to take some time. Okay. Yeah, I think it's shut. What, when did it shut down?

March. March. It was in March of 2020. So these, all of a sudden, all of these potential acquires are like, we're going to just, we're going to take a beat here because we don't know what's going to happen. Right. But you were that close to maybe getting acquired for three quarters of a billion dollars. 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 rate. with debt. So we took on debt because we had a plan, but we had very little cash, you know, 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 realize, okay, we have some significant cash issues here. And they're happening fast, right? Like, because, okay, now they're closing our stores. Well, that's, you know, it's a big number, big numbers a month. What did you see, like, percentage decline from March to April of 2020? Do you remember, like, more than 20%, 30%, percent?

Probably like 40, 50 percent. Just drops. Yeah, because it was, 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 40, 50, 60 million less than revenue, 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.

This is why bankruptcy exists. Your lawyer saying this when in April? This is April. April. Wait, how much debt did you have, by the way? Like tens of millions, hundreds of millions? Yeah, we know, we had like 30, 40 million, but that wasn't the point. And because you had, you couldn't get new debt.

So my, that's the bigger. Ah, huh. You couldn't go get money. 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. Didn't matter because our, so we had to pay our monthly payment to the stores, the 90 stores. The lease, right, the rent, right? We had to pay that number.

We had to pay all of our employees. Some of these stores are probably 20, 30 grand a month in rent, maybe more. 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. It was, and we had to tell them we can't take the product.

And they're like, well, you all. lost $30 million or whatever the number is. So the guy, I said, what is bankruptcy? You know, what do you, what is it? 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 read, 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. Yeah, but why was your lawyer? I guess your lawyer was suggesting this. It wasn't my lawyer. It was a lawyer they brought on who was a bankruptcy attorney. 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. Oh, very, it would have been very, very, very little. Like, they would have, you know. They'd gone after YouTube probably. Yeah, it would have been, wouldn't have been. So. I, I cannot imagine. even when that was brought up, because you're not a lawyer.

You know, most of us aren't lawyers. When a lawyer says that, I think a lot of people take it seriously like, okay, well, I've got to consider this. It was the hardest thing to run. 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, that's not a small thing. I don't mean to everyone goes through, everyone went through something with COVID.

So many businesses are 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, 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, all of our landlords one by one. We called all of our factories. Some were great. Some we had threatened back and forth with loss. suits, this and that. 90% 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. So 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.

Did Kleiner put more money in during this crisis? They did. They did. Okay. So they, and they probably got a good deal. They did get a good deal. I cannot, 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. Two during COVID.

I had four in, yeah, six years. Yeah, all that was happening. 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 wife and my dad. I didn't want to get them. You don't want to talk to them?

You don't want to talk to your wife or your dad about this? I didn't. It was so bad, by the way. 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. Yeah. 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. Nothing, of course. 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. Yeah. But you kind of start to emerge from COVID.

And we've had stories like this in a 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 growth. 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. They started buying the clothes again. 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, sure, I want to make sure, I'm very clear about this. So we solved the problem in 24, and we are now having a tremendous 25, and we are beginning our wholesale goes, and I can get into that in a second. As the the final phase, but we are, it just took four years. It was a four-year hamster wheel that we were in. All right. So you, you recover from COVID and back now again to, are you guys getting close to profitability? No, we're profitable. We are profitable. Okay. We were now 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. 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. Tell me a little bit about that decision. Well, like I said, 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. You know, I'm wondering now, I mean, here you've been through certainly trial by fire,

a lot of highs and a lot of lows in building this brand 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. 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. And I am, you know, I am, these three years have been very draining. And, you know, 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. I don't want to, you know, not be there for some of that exciting parts of it. Chris, given where you are now, I mean, you even admit that when you started this idea,

it was 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? 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 strategy, 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. 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.

That's Chris Rickabono, co-founder of Untucket. 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 sarah from New Zealand and what he's wearing, an early version of an Untucket button-down shirt. 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 Rumtina Ablui.

It was edited by Neva Grant with research help from Carrie 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 Coates. I'm Guy Raz, and you've been listening to How I Built This.