YouSaid · the spoken record

Chris Riccobono

lines on the record: 90
first: 2025-06-23
most recent: 2025-06-23
sittings or episodes: 1
sources: podcast

Every line below is reproduced as it was said and linked to the record it came from. Nothing here is summarised or generated. Directory · Search · Corrections

“Then $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, your market, you ship all your shirts. If they're bad, it's over, right? Now a paid 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 SERP before we became known. That's what allowed us to go.”
2025-06-23 · How I Built This with Guy Raz · UNTUCKit: Chris Riccobono · IDENTIFIED FROM THE TRANSCRIPT
“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 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...”
2025-06-23 · How I Built This with Guy Raz · UNTUCKit: Chris Riccobono · IDENTIFIED FROM THE TRANSCRIPT
“Stopped working them, but I also found this Swedish guy named Bjorn, who's still with me today. Older guy teaches at the Fashion Institute.”
2025-06-23 · How I Built This with Guy Raz · UNTUCKit: Chris Riccobono · IDENTIFIED FROM THE TRANSCRIPT
“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 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.”
2025-06-23 · How I Built This with Guy Raz · UNTUCKit: Chris Riccobono · IDENTIFIED FROM THE TRANSCRIPT
“If we're making 15,000 white medium shirts, which we do, 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.”
2025-06-23 · How I Built This with Guy Raz · UNTUCKit: Chris Riccobono · IDENTIFIED FROM THE TRANSCRIPT
“There's a reason why I found out that people do not make shirts designed to be worn on tucked. Our shirt has to be in spec every time if it is a inch too short, you can't wear it. If it's an inch too long, everyone else has it. You have to hit it each time. Cotton grows. You know, you can pull down most shirts an extra inch if you just give it a little tug. It shrinks. It moves. The heat 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, 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 your name is untucked, it sure sonnet and you're talking about this perfect length. It has to be perfect.”
2025-06-23 · How I Built This with Guy Raz · UNTUCKit: Chris Riccobono · IDENTIFIED FROM THE TRANSCRIPT
“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. Like they just don't, they don'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. Heck 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.”
2025-06-23 · How I Built This with Guy Raz · UNTUCKit: Chris Riccobono · IDENTIFIED FROM THE TRANSCRIPT
“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.”
2025-06-23 · How I Built This with Guy Raz · UNTUCKit: Chris Riccobono · IDENTIFIED FROM THE TRANSCRIPT
“I brought a UPS printer and we grew from there. I mean, we 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, I kept going. The next line that came out, I got the first shirt. I am 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 I pulls off. Next one pulls off. I take another shirt. The factory forgot”
2025-06-23 · How I Built This with Guy Raz · UNTUCKit: Chris Riccobono · IDENTIFIED FROM THE TRANSCRIPT
“You had to sell them. Yeah, that's the point. Today, you wouldn't do that. I loaded my third bedroom up with all the shirts.”
2025-06-23 · How I Built This with Guy Raz · UNTUCKit: Chris Riccobono · IDENTIFIED FROM THE TRANSCRIPT
“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, it's funny. 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? 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.”
2025-06-23 · How I Built This with Guy Raz · UNTUCKit: Chris Riccobono · IDENTIFIED FROM THE TRANSCRIPT
“So the funny thing is we made terrible shirts in the first year. 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.”
2025-06-23 · How I Built This with Guy Raz · UNTUCKit: Chris Riccobono · IDENTIFIED FROM THE TRANSCRIPT
“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 a hundred fabrics, said these are the ones I like. He said, I'll make them for you in Poland. No process, are you supposed to do tech packs and big order forms and this and everything automated? I told the guy, this is all I got. It's me and my partner. It was such a different time. 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, I wouldn't have worked out. I don't think the way it did or 10 years ago.”
2025-06-23 · How I Built This with Guy Raz · UNTUCKit: Chris Riccobono · IDENTIFIED FROM THE TRANSCRIPT
“We meet at a diner two times a week in the city on Fifth Avenue, 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 in them. 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.”
2025-06-23 · How I Built This with Guy Raz · UNTUCKit: Chris Riccobono · IDENTIFIED FROM THE TRANSCRIPT
“Yeah, he was building the because we had to raise some money. We had to build out a website. We had to start to think about how to market. So 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 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 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?”
2025-06-23 · How I Built This with Guy Raz · UNTUCKit: Chris Riccobono · IDENTIFIED FROM THE TRANSCRIPT
“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 how it took two years to get to market to finally get that right shirt. But that was the hardest part is finding how to make the shirt.”
2025-06-23 · How I Built This with Guy Raz · UNTUCKit: Chris Riccobono · IDENTIFIED FROM THE TRANSCRIPT
“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. 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. And 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. 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 I was just.”
2025-06-23 · How I Built This with Guy Raz · UNTUCKit: Chris Riccobono · IDENTIFIED FROM THE TRANSCRIPT
“You're right. 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.”
2025-06-23 · How I Built This with Guy Raz · UNTUCKit: Chris Riccobono · IDENTIFIED FROM THE TRANSCRIPT
“He's just incredibly smart. Always ask the most questions at Columbia. Very inquisitive, very good at multiple things. 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.”
2025-06-23 · How I Built This with Guy Raz · UNTUCKit: Chris Riccobono · IDENTIFIED FROM THE TRANSCRIPT
“Validating it but with excitement, and usually I'm used to them when I bring L for LP to them, they say not gonna work, you're out of your mind, or I bring a video wine blog. They say, Chris, you don't know enough about 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 Senandres, 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. He said, I'm in. You don't have to tell me any further. I've had this problem since day one.”
2025-06-23 · How I Built This with Guy Raz · UNTUCKit: Chris Riccobono · IDENTIFIED FROM THE TRANSCRIPT
“Well, that style shirt, yes, but that's not what we were making. You know, the oversized cutoff that 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, 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.”
2025-06-23 · How I Built This with Guy Raz · UNTUCKit: Chris Riccobono · IDENTIFIED FROM THE TRANSCRIPT
“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.”
2025-06-23 · How I Built This with Guy Raz · UNTUCKit: Chris Riccobono · IDENTIFIED FROM THE TRANSCRIPT
“Word 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.”
2025-06-23 · How I Built This with Guy Raz · UNTUCKit: Chris Riccobono · IDENTIFIED FROM THE TRANSCRIPT
“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, 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.”
2025-06-23 · How I Built This with Guy Raz · UNTUCKit: Chris Riccobono · IDENTIFIED FROM THE TRANSCRIPT
“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 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 into 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.”
2025-06-23 · How I Built This with Guy Raz · UNTUCKit: Chris Riccobono · IDENTIFIED FROM THE TRANSCRIPT
“Let's be clear for younger people who are listening to 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 midthigh 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 speck, and it fit me perfectly.”
2025-06-23 · How I Built This with Guy Raz · UNTUCKit: Chris Riccobono · IDENTIFIED FROM THE TRANSCRIPT
“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 sitting there in a t-shirt and love wine as much as the guy in France does who's wearing a tuxedo teaching about wine. So I was trying to go after that type of person. The other thing I tried to do was 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.”
2025-06-23 · How I Built This with Guy Raz · UNTUCKit: Chris Riccobono · IDENTIFIED FROM THE TRANSCRIPT
“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 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 a sales rep. I mean, I'm joking a little bit, but, you know, it's like they make movies about it. So I was the opposite. I'd come in and they'd look forward to talking to me. What'd you try to do? Where'd you go? What's your latest business idea? So I developed this ability, which my managers, I think, hated and everyone I worked with that I didn't have to go to the account and they still would buy from me. And that's what allowed me to last achieve so long because as much as they wanted to get rid of me, they couldn't because I was hitting my number.”
2025-06-23 · How I Built This with Guy Raz · UNTUCKit: Chris Riccobono · IDENTIFIED FROM THE TRANSCRIPT
“Yeah, and that's such 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.”
2025-06-23 · How I Built This with Guy Raz · UNTUCKit: Chris Riccobono · IDENTIFIED FROM THE TRANSCRIPT
“Yeah, and another one that I get told that I'm crazy for today because it sounds odd, but back then, once again, the internet, like all this stuff is new. I mean, an L4LP, if followed through, would have been a successful business. It just never went anywhere. And that's, you know, listen, that's the problem with... 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.”
2025-06-23 · How I Built This with Guy Raz · UNTUCKit: Chris Riccobono · IDENTIFIED FROM THE TRANSCRIPT
“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? Or, 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.”
2025-06-23 · How I Built This with Guy Raz · UNTUCKit: Chris Riccobono · IDENTIFIED FROM THE TRANSCRIPT
“Was thinking I could consult, I can go, which I did, go consult, go speak at different events, 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...”
2025-06-23 · How I Built This with Guy Raz · UNTUCKit: Chris Riccobono · IDENTIFIED FROM THE TRANSCRIPT
“That story is a guy who loved 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 wanted 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 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 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.”
2025-06-23 · How I Built This with Guy Raz · UNTUCKit: Chris Riccobono · IDENTIFIED FROM THE TRANSCRIPT
“And they thought 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 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.”
2025-06-23 · How I Built This with Guy Raz · UNTUCKit: Chris Riccobono · IDENTIFIED FROM THE TRANSCRIPT
“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 NBA got me excited. I was working really hard. So now I'm back doing nothing against 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 enjoyed doing it. Gary Vaynerchuk, I bought wine from him before he started that blog. I had this little camera and I wasn't sure what I was going to do because I was thinking, oh, 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.”
2025-06-23 · How I Built This with Guy Raz · UNTUCKit: Chris Riccobono · IDENTIFIED FROM THE TRANSCRIPT
“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 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 Colombia. I'm 27. At least I'm progressing this career.”
2025-06-23 · How I Built This with Guy Raz · UNTUCKit: Chris Riccobono · IDENTIFIED FROM THE TRANSCRIPT
“I couldn't get excited about selling medical equipment. I guess that's what it was. It didn't excite me. All these guys who I worked with, you know, yeah, 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.”
2025-06-23 · How I Built This with Guy Raz · UNTUCKit: Chris Riccobono · IDENTIFIED FROM THE TRANSCRIPT
“I just couldn't do it. And I knew, 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.”
2025-06-23 · How I Built This with Guy Raz · UNTUCKit: Chris Riccobono · IDENTIFIED FROM THE TRANSCRIPT
“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 heartbeating. Literally said, I can hear your heartbeating. 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.”
2025-06-23 · How I Built This with Guy Raz · UNTUCKit: Chris Riccobono · IDENTIFIED FROM THE TRANSCRIPT
“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.”
2025-06-23 · How I Built This with Guy Raz · UNTUCKit: Chris Riccobono · IDENTIFIED FROM THE TRANSCRIPT