UNTUCKit founder Chris Riccobono says consistency is key to success

Episode transcript, edited for clarity.

Bill Thorne: Welcome to Retail Gets Real, where we hear from retail’s most fascinating leaders about the industry that impacts everyone, everywhere, every day. I’m Bill Thorne from the National Retail Federation, and on today’s episode, we’re talking to Chris Riccobono. He’s the founder of Untuckit and the sportswear brand Greatness Wins.

We’re going to talk to Chris about his entrepreneurial background, growth strategies for his two brands, and what the future of retail looks like. Chris Riccobono, welcome to Retail Gets Real.

Chris Riccobono: Thanks for having me. Appreciate it. Bill.

Thorne: You have an origin story. Untuckit has an origin story. So let’s hear both. Take it from the top.

Riccobono: It’s been a while now. We started the whole process in 2010. I was actually a sales rep for a medical device company, GE Healthcare, selling medical equipment, had nothing to do with fashion, no connection to fashion whatsoever. Didn’t have any idea what I was doing. For years I knew I needed a shorter shirt, but I kept saying to myself, these bigger brands — J.Crew, Brooks Brothers — if there was a need for it, or if they could sell it, they would do it. So why would I do it?

I was also intimidated like any entrepreneur, any, we’ve all met friends, probably every friend, you know, who has this great idea and, but never does anything with it. That’s kind of every person you know. And I was the same as those people. I knew I wanted to be an entrepreneur, but I was scared. I didn’t know how to launch a website. I didn’t know how to market. I didn’t know how to manage financials. I didn’t know how to make a shirt.

But I was about, I graduated Columbia business school in ‘07 or ‘08, and I said, “You know what? I don’t have a great idea. I’m going to go into, start over and go into finance as a trader,” which is what every person in the Northeast does near New York City. They were all these guys seem to be making a lot of money and I figured, let me try, and I was going to start at the very bottom rung making $30,000 a year at 30 years old after graduating Columbia, and luckily the market crashed in 2008 and I had no choices.

So, I said, you know, “What do I love to do? The only thing I really love to do is drink wine.”

Riccobono: So, I decided to start filming videos of drinking wine and tasting it, teaching people about it in a more, very informal way as opposed to a kind of an intimidating way, which is what young people perceived wine at the time. It’s changed now. Everyone drinks wine.

I learned how to launch a website, and to market on Facebook, and it made me no money. It really didn’t go anywhere. Not many people watched it, but it gave me confidence to actually launch something.

And I said, I came up with this name Untuckit. I was down at my parents’ beach house, and I was, I said, “Untuckit. You know, I love that name.” And I called a few different people and they all said, “It’s a horrible name. You need a fancy name for fashion. You know, it needs to be in cursive and, look at Brooks Brothers, look at J.Crew.” And I said, “If I’m launching a fashion brand, I’m not doing it like anyone else has done or else it won’t succeed, because there’s no need for a new brand. There’s already plenty of great brands, billion-dollar brands.”

I said, “I’m going to take a shot at it a different way,” and so I started the process. I went into 37th Street and Ninth Avenue, and I brought my one out-of-spec J.Crew shirt that was a small but fit like a large and luckily was able to be worn untucked and I’d worn it — That’s all I wore. Every time I went to try another shirt, I put this one back on.

And I said, “Can you make this shirt for me?” I didn’t realize how complicated a process it was. You need a technical spec person, you need a pattern maker, you need all these different things, which I didn’t have.

I said, “Just can you please make it?” I begged them. They made me the shirt and it was a fine shirt. Um, but that’s what started the process. 

I called my friend, Aaron Sanandres from business school, and I said, “Have you ever had this problem?” And I started going through it and he cut me off. And in the past, I called him with a hundred other ideas, and he would just say, “that’s a terrible idea” and hang up the phone. And this one, it resonated. He said the exact same problem.

So, we did a survey in Hoboken and we showed three different pictures and out of the [men] coming out of the PATH train, 95 percent of the men said they had a problem and 95 percent of the men said they want it to fall in the middle of the fly. So now we’re like, “There is a problem here. You and me have a major problem here that we can’t find a shirt that looks good untucked, and we just did this survey.”

So, we tried to raise money and raising money from wealthier, older men, when you’re pitching a shorter shirt, is not easy. Between them saying, “What are you talking about? I don’t even wear my shirt untucked.” Or they kind of laughed, which I can’t really blame them.

We raised $150,000, which is not a lot to raise to launch a fashion brand. I stayed at my job full time, Aaron stayed at his job full time, and we tried to sell shirts. The problem is the shirts were terrible that we were selling because I had no idea to make them. I didn’t know you had to pre-wash shirts, take out shrinkage. I didn’t know you had to make buttons a certain way, all these different things.

The other problem is the factories would send me the shirts. I’d measure them and they’d be an inch and a half long, or an inch and a half short. And they said, “What’s the problem? That’s cotton. Cotton moves. That’s how you make it.” No one cares about specs and that was always one of my big things. I’d order 20 J.Crew shirts or 20 Brooks Brothers shirts and I measured the same exact shirt, same exact size and there’d be like this much difference between each shirt because no one cared because the shirts were so big that you wouldn’t notice it.

Thorne: I’m going to go home and start measuring my shirts. Thank you, Chris. I really appreciate it, like I don’t have anything else

Riccobono: I don’t know if you ever had the problem. I used to find a T-shirt or something and say, I love this. I’m going to buy another one and it would fit different. They never fit the same.

Thorne: Totally. Totally, totally, totally.

Riccobono: So, I said, “Guys, my business doesn’t work if it’s an inch longer, it doesn’t work if it’s an inch shorter.

At the time, luckily, fashion was struggling so these, these factories wanted — talk about the amount of luck you need to start a business. Everything has to be aligned. They wanted our business, and I said, “We got to do a hundred percent inspection. We’re going to reject anything that’s a quarter inch off spec, and that’s the only way we have a business.”

So, after two, three years of making terrible shirts — luckily we didn’t reach a lot of people because we didn’t have money to market, so we were just using PR and occasionally people went to the site. But the thing is we would get these long paragraph emails from like 50 percent of the people who found out about our company saying “You’ve saved my life. Thank you so much. I wish I came up with this idea. I’ve been looking, thinking about this for 20 years, whatever.”

And we’re like, that’s not normal. You don’t [get] emails like that for a clothing brand. In 2014, we were sick of growing slow, and we were like, we just have to use our last $21,000 and all we could afford was local radio reads. No one has ever advertised fashion on radio because you can’t see the product, but it’s all we could afford. So, we called a local sports radio show and they said, “You’re going to need $150,000 in three months because if you know anything about marketing, you need to convince the customer a few times before he’s going to buy.”

We said, “We don’t have that. We have one week and we have $21,000.” So, we did it and immediately after the read, which you know, said, “Shirts designed to be worn untucked” and told the story, “Do you ever have a problem? You know, that your shirt was too long,” and a thousand people would go to the site and most of them would buy.

We said, this is incredible, so then we did airline magazines. No one did airline magazines except fragrance companies and watch companies. Now everyone does. Pre-pandemic, everyone did. We would spend $15, make $45. Anything we spent people came to the site because there was a great story being told.

It wasn’t a classic fashion brand where you had to see the shirt. You had to buy into the concept and you were intrigued. You came to the site and most likely you bought. Fast forward in 2015, we opened our first brick-and-mortar pop-up in SoHo. Everyone told me that brick-and-mortar was dead. We knew that 70 percent of men were emailing us saying they’re not buying our product unless they can touch and feel it.

We start this pop-up shop and we had started to grow. At this point, we had gone from like $500,000 to $3 million, and we were leaning to heading towards $15 million in 2015 when we opened up this pop-up shop and I worked the floor for the full three months and I’m not kidding.

I must’ve been hugged a hundred times, like hugged by men who were in-store shopping. Thanking me for figuring this out. It was mainly non-fashion forward guys. It was guys who were the type of guy who told your friend, “I don’t care how I look. I’m not into fashion,” but in reality they do because in reality, everyone wants to look good no matter who you are.

But they didn’t want to put in the effort and they didn’t know where to start. But with this, they would come in. It was a try-on shirt. They put it on. It was this much shorter than any shirt out there at the time. And they looked great. And their wives would say, “Oh my gosh, you look horrible. And that other shirt you wear, you need to buy this.” And now they, the same fit across all the shirts and they’d buy five of them and leave happy.

We opened up five stores the next year, 35 stores and 35 stores, which has to be up there for some of the most stores opened in a year. And it was going incredible.

We started coming out with other products because men would write in: “My polos are too long. My T-shirts are too long.” And most importantly, they’re inconsistent. One would be long. One would be short. Then we start saying, “Well, what do I wear over my shirt untucked? The sweaters are covered up or the sweaters are too short, or my sports jacket doesn’t pair the way you wear yours when we show them in the ads.”

So, we started developing all these products and they all were selling, and we kind of just took off. Everything was going incredibly well. In 2019, we had 90 stores. We had opened in Canada. We had opened in England. We were kind of the talk of the town, if you will, in fashion.

Everyone was copying us. Literally everyone was copying us. J.Crew led all their campaigns with shirts meant to be worn out. Vineyard Vines, the shirts that were big and baggy and tucked in, had a section in their store, shirts meant to be worn untucked.

Which by the way, that was the greatest moment of enjoyment, like the fact that I started this thing out of my — me and my partner started this out of our apartment, my apartment in Hoboken — and all of a sudden these billion-dollar brands are copying us.

J.Crew used to have a, have a call called the Untuckit call, supposedly by Mickey Drexler, because they were annoyed at why we were growing and everyone else was struggling at the time.

So, everything was great and then we were about to sell the business for a lot of money. We had 15 bids coming in in 2020 in February, and we shut it down because of the pandemic. Three months later, we were on a call with a bankruptcy attorney who said, “You guys are the reason bankruptcy exists.” So, we went from here to here.

Like, I was in my mind thinking, “What am I, how am I going to, I got to sell my house. I got to maybe become a sales rep again.” Because you don’t, you own, you own nothing. They kick you out. You don’t only get no equity, your equity goes away, but you also don’t have your paycheck the following day.

So I hung up, I called my partner and I was like, “We are the fastest growing men’s brand. We cannot — and not only that, we are positioned better than any product in the world post-pandemic, because what are you going to do after you start changing out of your sweat pants? You’re not going to be tucking in a crisp white shirt and putting on a sports jacket. There’s going to be something in between.”

So, we pleaded with all of our real estate guys and our factories and they gave us incredible terms. I mean, I think our accounts payable got to $90 million at one point, and I didn’t sleep for months and months because it was never ending as you know. Every day you’d wake up, I’d put on the Today show and pray the news was good, and they’re like, “We don’t know if this is ever going to end.”

We survived in 2020 and 2021. And in 2022, we had our best year ever, and the reason we had our best year ever — or those people who are into the kind of econ model and direct-to-consumer model is — what was happening in 2019 was every brand was just spending tons of money on marketing and growing.

So, you’d have a brand that would be doing $200 million, $300 million, losing $100 million, and these private equity guys thought they were tremendous. They’d overvalue them. Some of them we know that have gone public, they were valued at $7 billion at one point and now valued at $150 million today.

In reality, it was all fake. That wasn’t the revenue that was honestly what that company would have done. They were buying revenue. And when they tried, when they realized that they had to become profitable because things changed, they would lower their marketing spend and they would stop growing.

That’s basically when you’re done. If you can’t grow and you can’t be profitable, you’re really not a company. For us, we said we, what I think we did, we did a great, we were truly a brand. There’s a lot of direct-to-consumer companies in 2019 that we don’t need who are valued at $700 million, $800 million, $1 billion, who we don’t even know their names today. They were kind of riding the momentum.

Once even more and more entrepreneurs came into the business — which just happened, as you know, if you scroll Instagram, there’s 50,000 companies all making nice clothes — they just couldn’t grow because they weren’t a brand. With us, I think we did a great job really becoming that brand and that if you see what…

A great thing that happened was people would always come up to me and say, “I saw Brad Pitt was wearing an Untuckit” and I go and look and I’d be like, “That’s not an Untuckit. It’s an untucked shirt.” But everyone started calling untucked shirts Untuckits. Like a [Kleenex] tissue or Xerox and a copy machine. That’s when I knew, “Wow, we’re going to be around for a long time.” Like, we’re going to survive this and we’re going to be one of these guys who comes out of this thing.

We cut marketing, and we grew and we became profitable. You know, we made, you know, significant EBITDA last year. We grew the business and it was all because when we turned marketing off, people still bought because referrals. So this year, same thing. We’re going to double our EBITDA growth, and continue to grow.

So I told the whole story very fast, but we’re more excited than we’ve ever been, and the reason is we’ve not done any wholesale and no brands at our revenue have not done wholesale. Most of the time it’s done the opposite, even the direct-to-consumer brands. Like if you think about a Bonobos, they had a huge wholesale business when they were growing.

So we have an unlimited upside in the wholesale world. Independent wholesale and the major wholesale people that we know. We also have because of our brand, we have tons of opportunities coming at us for licensing, licensing fragrances or even sneak shoes, and I hate to say that the famous timebomb, a beach chair. We’re going to be very smart when we make those decisions. You see more of those — I don’t know about you, but every single human being on the beach has a Tommy Bahama beach chair by me.

Thorne: I have four. I really do.

Riccobono:  It’s incredible. It’s amazing. That business is just incredible. So, we think we have those opportunities. We’re licensing going into Philippines and Dubai and we’re going to be going into Mexico, so we have tons of growth opportunities beyond just the United States.

We also think 97 or 98 percent of our stores are profitable, so we want to open another. All these companies popping up, opening stores. We have 90, we want to open another 25 that we’re confident will all be profitable.

So, we’re kind of in my … all the stories I’m hearing out there for direct-to-consumer brands, which is, “Too expensive to bring in customers. Can’t get profitable. Closing stores.” We’re seeing the opposite, which is why I like to tell the story because I don’t feel like it is told enough that there is a way to do this right, I think, and it’s very exciting for us.

Thorne: I think one of the things I like most about the story — there’s a lot to like — I really, you know, it’s the seeing great success and then having COVID hit, who would have thought, everything that you had to go through, and yet you survived and you not only survived, you thrive.

But something that you said very early in the conversation, which was, you know, retail and brick-and-mortar is dead. I mean, this is what we heard starting literally in about 2012, 2014, and we really at the NRF, did an all-out assault on that narrative. There was no basis for that. It was just people that would see a for lease sign and say, “Oh, there you go. You know, that’s what happens when the internet takes over.”

Riccobono: It was driven by some of the direct-to-consumer brands who were popping up, who wanted people, wanted that to happen. I always say this about shopping, when people then once again, try to say it’s over for good now, after corona[virus]. People have left their house, even the old — I don’t want to say old people, but the people who weren’t — like my dad who didn’t shop online, they learned to do that during the pandemic. But what people don’t realize that the mall is a hobby. It’s an activity. You go to the mall with your mom, with your dad, with your husband. You go there, you have lunch, you have dinner, you shop, it’s an activity. This isn’t… it’s never going away. When you travel to Florence, you spend a day shopping. You, when you try, like, it doesn’t matter what you’re doing. It is an activity and a hobby that will never, ever, ever go away.

You know what I mean? It’s just, now, it definitely slowed down. The funny thing is the bigger slowdown was during corona because there are still …

I would say that we’ll probably have a drop of like 10 percent of customers who will never shop in stores again that we’ve seen that are just online now, so you definitely saw some of that. Now, will that go back? Probably at some point.

Some of these major cities just have not recovered. They’ve changed. There’s crime, there’s homelessness. We all know them from watching the news and those might never recover because they’ve just changed. The landscape changed or they’re going to be back as strong as they’ve ever were and they are quite frankly.

Thorne: We’re seeing it here in Washington, D.C., and I think if you listen to a lot of these electeds — municipal electeds particularly that are in cities like Minneapolis — I mean, those cities have changed and probably never going to be what they once were pre-covid because offices are closed, the hybrid work schedule, the remote work from home.

But at the same time, I mean, yes, it has had an impact, but that hasn’t kept people from going to the store. They still go to the store. They still go to the mall. They still go to the grocery store. They’re just not doing it maybe the way they did it before and I think those that anticipated it … or those that were, you know, I don’t want to say flexible, but recognized the opportunity still existed to continue to grow in other ways, well, they succeeded. Obviously, you succeeded. So it’s …we could go on and on.

We may have to do another episode, Chris. I’m not letting you go. This a great. You have a phenomenal story. A lot of our listeners would say, “Well, you know, this guy has done something I’ve dreamed of doing, and he’s done it right, and I’ve been very nervous about it, but if he can do it, given his background and experience, I can do it. I know I can do it.”

Riccobono:  Yeah, there’s so much to talk about and also the incredible amount of luck you need, which I always like to point out, you do. You need the idea and you need so much luck.

Thorne: So let’s, let’s get to the other brand real quick. Launching Greatness Wins. Why this? Why now? And why with these partners, and you have some extraordinary partners.

Riccobono: What happened was the pandemic. When we shut down the stores, I get bored very easily and I need, it’s funny, we talk about drinking wine, my favorite thing in the world to do is drink wine and work.

I didn’t have enough to get my mind going on. Untuckit was on kind of pilot. We couldn’t market. We couldn’t come out with a new product. We couldn’t come up with a new strategy. And I started, I literally said, what else do I have a problem within fashion?

And I realized that everyone, most people were doing two things during the pandemic, they were working out and they were laying on their couch, right? What I found out — when I was, or they were going for — well, actually, they weren’t going for coffee when we were fully locked down — but they were wearing athleisure and when I was wearing my nice athleisure clothing, I felt good and looked good. When I went to go for my run, I changed into my athletic apparel, which performed but looked bad, right? And pilled and didn’t hold up a lot of the times.

I ordered all the big athletic brands and I measured them all, the same thing I did with Untuckit, and I’m not kidding, some of those bigger brands, there was … in a seven-inch short, there was this much. I had a short that was this big and this big. There’s no quality control anymore.

Thorne: So seven to nine, if you order a seven, you could get anywhere …

Riccobono: I had an eleven, and I had a four, I had an example of it … because they are too big and they don’t need to. They’re very successful. They do great. I don’t want to talk net. These are, these are brands that you can only dream of.

It’s just today, they’re focus on quality — with having a hundred different factories — has gone out the window. They don’t do the same tests that we do, and I work with the same factories that make these brands. They don’t do all the pilling tests and the shrinkage tests.

So, I said, there’s not been a new big time athletic brand … Now, when I say athletic, I mean, one day we’ll be selling soccer stuff, tennis stuff, basketball stuff. That’s not athleisure. That’s athletic, and the last athletic brand was Under Armour. There’s no other area in clothing where the last time someone came into the space was 22 years, 26 years ago, right? Every day, the bra company, there’s 15 new bra companies a day, you know, lingerie. So, I was like, there’s a time for a new and a better fitting, more modern fit athletic brand.

Then I said, all right, well, what about athleisure? Well, athleisure, the clothes that I wore that I looked so good, and I would take them off. They just didn’t, when I felt them, it’s like, this is not meant to go for a 30-minute run. It’s meant to look really good.

So I said, I want to be what I called, the lululemon of athletics, from a men’s perspective, and I said there’s a need for a more modern fit, higher quality athletic brand.

I said, how can I differentiate this even further? Cause that’s the way I think with Untuckit. Like you, I always tell entrepreneurs, “Don’t call me and say I’m going to make this great shirt. Everyone makes great shirts. You need a hook. You need a story.”

And Greatness Wins — coming up with that name, everyone hated it. I loved it because it makes you say … How many times [did] people tell me, “That’s not a name of a clothing company. It’s an expression.” I said, “That’s exactly what I want you to be arguing and I want you to be remembering it when you’re at a cocktail party.”

And finally, it was athletes and I knew Wayne. Wayne had invested in Untuckit. Greatness Wins, the Great One. It made too much sense. I said, “Who else can I get?” And I saw Jeter’s thing came up with Nike, and I was like, I’m never getting Derek Jeter. He doesn’t do anything with anyone. You know, you don’t see him. He doesn’t, he’s not one of these guys who markets, and I just bothered him and bothered him and bothered him and finally got him to say, “I’m now excited about doing this.” And he came up with the idea to bring Misty Copeland in, which I loved because it’s not the classic sports like basketball or, you know, female tennis. It’s ballet, but ballet is … some of the greatest athletes in the world do ballet.

So, we got together and we tweaked the idea, and we launched a year ago and it’s going great. We’re actually doing this golf line that’s pushing into all pro shops. We’re having a lot of success. We sold out of four of the top 25 pro shops this spring in a test. We are launching women’s in October, October 5th.

It’s very exciting and it’s totally different than Untuckit, which is great for me. I can see both the athleisure/athletic side and the more dressy side, so if another pandemic comes, at least I’m ready.

Thorne: You’ve got to cover it on all sides. So, Chris, we are running out of time, but I have one, I think, really important question to ask, and it’s one that I ask all of our guests. What’s the best piece of career advice for those just starting out in retail?

Riccobono: Oh man, it’s funny because I consider myself still an entrepreneur and I joke around when people say I’m in fashion because I just can’t … I’m kind of get my arms around that. I don’t even use the same right words. It drives my merchants crazy.

I would say in retail or anyone young, whether it’s retailer or more of entrepreneurialism, is that, it’s a battle. You have to be prepared, as a young person, for lots of pain and one step forward, two steps back. Not two steps forward, one steps back. And you have to be resilient, incredibly resilient because it will all work out, and the biggest thing is that you got to enjoy those moments of pain.

It’s funny because I had been through so much pain going into corona. When I say pain, everything going wrong. When corona hit, I actually enjoyed it and what I mean by enjoyed it, I said, “I am going to survive this and when I do this story just got that much better.” And my journey got that much better, and the day that I sell will have gotten that much better, even though it’ll be a lot less equity.

But yeah, it’s … to me, it’s just … you gotta be resilient and you got to expect hard times. That’s what I tell all young people, specifically entrepreneurs, and you’ve got to enjoy those hard times, and everyone says that that’s when you learn and that’s when you better yourself.

Thorne: I see a book in the works, Chris. I mean, it’s a fascinating story. It really is. And I think if you combine your personal story along with your professional journey, you may want to give it a few more years, but I definitely see a book. Congratulations on what you’ve done, what you’ve accomplished and, on two great, great brands. It’s been a real pleasure talking with you, Chris, and thank you for joining us today.

Riccobono: Thanks, Bill. Really appreciate it.

Thorne: And thank you all for listening to another episode of Retail Gets Real. You can find more information about this episode and more at retailgetsreal. com. I’m Bill Thorne. This is Retail Gets Real. Thanks for listening. Until next time.