Chris Riccobono 0:00 

I do a lot of my own stuff, and I do it because I feel like I could tell my story better than anyone else can. And it's going to come across as being passionate, that I really love my product and it really is better than anything else out there. I think that's what makes you a great salesperson. I mean, a lot of people say I'm intense, but it's really just passionate about the product.

David Novak 0:26 

Welcome to how leaders lead, where every week, you get to listen in while I interview some of the very best leaders in the world. I break down the key learnings so that by the end of the episode, you'll have something simple you can apply as you develop into a better leader. That's what this podcast is all about. Now, if you want to get better at motivating or inspiring or convincing people, then you're in the right place, because my guest today is Chris riccabano. Now you might recognize Chris, I'm sure you will from his commercials as the founder of untuckit, the incredibly successful clothing brand, known for making a dress shirt you don't have to tuck in. They sold over 12 million shirts. But it hasn't been an easy road. Chris tried a lot of other startup ideas before this one stuck, and during the pandemic, untuck it really took a beating, and they're still recovering from it, as you'll hear it today. But through it all, Chris's passion never wavers. And let me tell you, passion is powerful. When you let your belief in a product or an idea shine through, people respond, and that passion can keep you going in both the good times and the bad times. Oh, and by the way, you're also going to hear about Chris's latest brand. I mean, he is a serial entrepreneur, and he started this brand with Derek Jeter and Misty Copeland, and it's called greatness wins, and we'll get to that here in a bit. But here's the big idea, if you want to put your passion to work for your business and learn a lot about building great brands while you're at it, then you're going to love this conversation with my good friend and soon to be yours. Chris Riccobono,

you know, I don't know how you've done it, but somehow you've convinced the good majority of the business world that wearing a shirt untucked can still be professional. Now, did this idea come from a personal habit of yours? This was

Chris Riccobono 2:34 

that classic idea. I always wanted to be an entrepreneur. So I was thinking of every dumb idea you can imagine. I just wanted to get out of corporate America, and I personally, my one problem I had was that I couldn't find a shirt. This is what I say in a commercial, but I couldn't find a shirt that looked good untucked. And it really was a problem. They were all too long every one. I had one out of spec shirt from J Crew, and I wore it over and over again. I was in Las Vegas, I remember, and I'd go to put on the new shirt, and I go right back to the old one. And I started asking my buddies and everyone would have this incredible response, this passionate response about having the same issue. But of course, you always think that there's a reason why it hadn't been done. So you never think, as someone who's not in clothing, that you can just start a clothing brand. So I kind of just never did anything about it, until one day, I got even more desperate to try something new, and I I began the process.

David Novak 3:25 

Well, desperation leads to big ideas, and that's one of them that's that has certainly been a success. You know, it's interesting. I was talking to this tailor who has his own business, and he says that, you know, he actually makes shirts now that you can wear regularly or wear untucked, I bet you have all kinds of competition now because you've come up with this idea. How big of an issue is that for

Chris Riccobono 3:49 

you? Well, in 2019 every single it was actually a great moment as an entrepreneur. It was a little bit painful, but when you realize that every single fashion brand led their campaign with shirts meant to be worn untucked. You know, the Vineyard Vines of the world, which are known to be tucked in and oversized, had a section in their store that was shirts meant to be worn out Banana Republic, J Crew, huge signs, and that's kind of continued. But the good news is we had developed such a strong brand by then that people call untucked shirts. Untuck its just like they call a tissue a Kleenex or Xerox. So I think it got a lot of our customers. We would get emails from customers who are annoyed about these people copying us. And to be honest with you, you'll laugh at this, but it sounds very simple to do, but it isn't because to get that right length over and over again, you need to have this 100% quality control at your factory. Otherwise, if it's a little long, it looks like any other shirt, and if it's a little short, you can't wear it. So, you know, I still think we have a differentiated product. Well, the

David Novak 4:51 

one thing you have is you have a great brand name untuck it just tells you exactly what it is. And you obviously have got your shirts just geared for that. Then. Fit that you deliver so well. Give us a snapshot of the brand that you have today and the business model for untucking.

Chris Riccobono 5:08 

Well, it has been a roller coaster ride, because if you think about it, I'm now at about 55% of my time pre covid and about 45% post covid. And that changed everything in my world. You know, covid ran into high inflation, huge interest rates, so we're still impacted by it today. In 2019 we had open 90 stores in two years, and we didn't do wholesale intentionally. We loved owning the customer data. We were the most talked about men's brand out there. We had gone into England. We were in Canada. We had gone from, I think, 140 million, 195 million. And we had 15 letter of intents coming in on February 27 2020 for north of 700 million. So it worked, you know, the blueprint worked. And we were ahead. And fast forward to three months later, we were essentially going to declare bankruptcy, and it was completely out of our control, as you remember, so we took on all this debt to get through, and interest rates went from 8% to 13% so now we're paying and so I answer this question in that it's just been one thing to navigate after another, and then all the competition came in, obviously, so we just had to find ways through it. You know, cash strapped at times, consumers looking for sales. The dynamics changed. So I don't know if I answered your specific question, but I can tell you, it's just the last four years have been completely different from the first six years in all the things that you have to manage and think about when you're running a retail brand,

David Novak 6:41 

so covid Basically just, you know, not the win from your sales. And were you not able to pivot to digital in a successful way?

Chris Riccobono 6:50 

People thought that that would be easy. They just sell online. It wasn't the fact that our stores were closed. It was the fact that everyone was wearing athleisure. Everyone moved their money into athletic and athleisure brands, and they weren't wearing a button down shirt. People wear our shirts doing all different types of things. They wear them to work, they wear them to dinner, they wear them on vacation. They don't weren't doing any of that stuff over covid. So luckily, we still listen. We did, still did quite a bit of revenue, but it was done through our polos and our T shirts and our henleys. That was the main problem, that until people got back living their lives, they weren't going to buy their 10 on Tucker shirts for that year. It was tough. And the bigger problem was we had to take on debt to get through, you know, the pandemic. You know, we had never really raised money. We had raised $8 million by the time in 2019 most brands our size had raised, you know, 150 to 200 million. But our marketing message was so powerful that we would just have great returns. But then when covid hit, you needed cash because you needed to last so and then going right in. No, people don't realize it goes right in. People talk about the economy being great because the stock market. The fact is, you know, people are spending $10 for a coffee and to buy $105 shirt is tough, so it's been a roller coaster ride. Now, the good thing is, our brand is so strong. We have such a great repeat business, and people love the company, so we're able to still succeed, but it's been a challenge.

David Novak 8:13 

I saw where you actually extended your brand, where you had not only have a full line for men, but you also have it for women. I mean, that that had to be a big brand decision. I mean, how did you, how did you make that decision, and how's that doing?

Chris Riccobono 8:27 

That was an easy decision, because it was done because 60% of women, you know, shop in our stores for their husbands, and they were always in there, you know, whether their husband was with them, trying on stuff, and they'd say, what, you have nothing for me to look at here. You have no women's and we have great quality product. We have great customer service. So when people are on the site, and that's how we expand into all these other products, you know, our pants and our polos and our shorts and our bathing suits and the list goes on, is because the consumer is already in the store. He's already online, and it's easier just to buy from the same brand. So women, they buy shirts for their husbands or their boyfriends, and then they go buy product for them. It's doing well. It's about 10% of our business. And you know, I think there's a huge upside there in the future, as we get out of this these last four years and start to grow, though, that makes

David Novak 9:14 

so much sense, the logic you had to really bring women into the fold. But, you know, one of the things that I would imagine be a challenge. You know, particularly in the economy that we're in, consumers being stressed. You really got to chase the volume. You're chasing revenue. I mean, how do you how do you decide what segments you can really go into and still protect your brand? That's

Chris Riccobono 9:34 

hard. In general, when you say, because it's the discounting in the sales that's making it challenging, because we were the consumer forced us there in covid, right? You needed cash. Everyone was on sale during that period of time, even brands that never were on sale. So you had to do it. Then you come out of covid, and we want to go back to the way we used to be. We had very few sales for the first six years. But then the environment changes, and even if you're a company that doesn't want to do sales and. Typically doesn't have to. If your seven closest competitors are on sale every week, you're going to lose customers. If you don't do something, you're just kind of forced in there. So that's another thing that's just gone on. It went from covid into these high interest rate, high inflationary periods, where now our competitors are doing sales. So we're forced having sales. And it is that give and take, you have to, you can't. We don't want to be a company that's on sale all the time, so you have to be willing on certain weekends, let's say, or certain periods of time, to pull back on sales, which might decrease the revenue, but over time, we think will be better for the brand in the long road. And that's just a fine balance. And if you're having cash issues and all these different things play into that. You

David Novak 10:43 

know, Chris, I can't wait to talk more about your journey at untucket and also about your new brand greatness wins. But first I want to take you back. What's a story from your childhood that shaped the kind of leader you are today?

Chris Riccobono 10:56 

You know, I was a I always go back to and sometimes maybe I think I give it too much credit, but I played tennis growing up in individual sport. I played in college. I think that shaped a lot of who I am, in general, just the things you learn that maybe you don't even realize you're learning, the resilience, the hard working, the dedication, you're kind of out there alone, you know, I I'm an entrepreneur. It's funny when I think about leadership, I was actually thinking about this a little bit before the conversation. And I think an entrepreneur who's a leader is a different leader than a leader who came up through corporate America, because a leader who came up from corporate America, they go through this process where a lot of times they're doing leadership programs, they're learning they're being built to be a leader, an entrepreneur. It's kind of funny. You're become an entrepreneur. You're going by yourself, right? The first three years of my journey, I wasn't a leader. I was I was alone, you know, away from everyone else, including my family, at times, you know, trying to do something which everyone's telling me I'm crazy for doing. And it's funny, you're not public speaking. You're not doing any of the things that all of a sudden, once you achieve success, and you have six, 700 people reporting to you, and you have to be out there, and you have to be doing all these things that you never had to worry about when you were building the brand. So I think you become a different type of leader. And I think it all ties back to when you're an entrepreneur, you're a few things I think should be assumed. You're hardworking, you are dedicated, and you are resilient, because there are, I always say it's two steps back, one step forward every day that I, you know, turn on my computer, there's more problems than good, and that's across all industries. For some reason, you feel it more as an entrepreneur. You know, they always talk about an entrepreneur being a lonely, lonely life. So I do think, to answer your question, I think that playing tennis competitively taught me what I consider to be the two you know, the hustle, hardworking, resilient, and that helped me take the risk to go out and become an entrepreneur.

David Novak 12:52 

When did you first decide you wanted to start your own business? When did that thought or that dream come into your head?

Chris Riccobono 12:58 

I went to my first interview in Providence College, and the guy stopped the interview because he could hear my heart beating. And I realized, oh my gosh, I don't like corporate America. I don't know what it was. I just got scared by that whole corporate America. Put on a suit, shave, go into work. So I said, I have to find a way to work for myself. So what I did was I went and I got a sales job. Strategically, everyone was going into finance. I said, if I go into finance, I'm not gonna have time to work on different ideas. So I got a sales job, and instead of selling, I would work on my ideas, and I would build relationships that allowed me to sell and still keep my job at the company. So I always kind of had a plan. Now, the problem is I was getting older and older, and, you know, I had not had kids, I was not married, which is a lot easier to be an entrepreneur when that's not the case. And I was trying some terrible ideas. I mean, ideas that went went absolutely nowhere, and that, you know, you would laugh at if you heard them. Well, let's hear one of them. This is an embarrassed one, but I always tell it because it it actually would have been successful. There was. And this is before these dating sites, but it was called Love for little people. L4 lp.com, now this is before there were all of these, you know, sites out there, and there was one show on TV, and I forget the name of the family that followed, you know, a little people around and and we got on the phone with this guy, and he thought it was a great idea. And then something happened in his in his world, and it never got going. But that's the kind of things I was thinking. It was whatever I could do, you know, I was, it's very hard to come up with an idea. And even, by the way, making a shorter shirt wouldn't be much different than elf, like when I went to try to raise money for my father's friends for a shorter shirt. I mean, I thought, think they thought I was crazy. Do you really gonna launch a business and make a shorter shirt? Like, what are you doing, Chris? Like, just go back and work, you know. Well, when

David Novak 14:50 

you have this, you know, all these people are calling you crazy, right? And you start this business, and it's a lonely way to start, because you're the only believer at the beginning. What was it that you had inside of you that could keep going?

Chris Riccobono 15:04 

It's amazing when you have no fallback depression, and I think it really helps you succeed. I was working at G healthcare, selling medical equipment, and I was ruining every relationship I had there because I was spending these guys would call me lazy and would bother me so much because I was meanwhile working 18 hours a day on untucky, and they thought I would never go to the go get drinks afterwards. I would never do anything to improve my standing in General Electric and it was because I was putting so much effort into Ontario. And I remember each morning in Hoboken, I get a I walked to Dunkin Donuts to get a coffee, and on the way there, I had this pain in my chest, and I said, if this doesn't work. I'm done. I'm going to be 35 years old. Have burned bridges. I'm going to be, you know, who knows what job I'm going to get. And that was a fear. I mean, I would wake up in the middle of the night because I'm, I'm trying to sell a shorter shirt, you know, at the end of the day. And we had a really rough start. We don't, I do not know how to make clothes. I was wandering the Fashion District. The first shipment of shirts we ever got, I undid the button and I done, did the second one, and I took another shirt, and I did the same thing, and they forgot to tie the buttons every single shirt, the buttons fell off. So I shipped the shirts with a note that said, the buttons are going to fall off. We'll replace them. I mean, we had no money. I didn't know what else. There was nothing else I could do, you know, and then I remember, I would spend, I would iron shirts, because we were packaging, packaging them. So I'd come home to 100 shirts. I would, I'd be ironing for four hours, just like an ironing lady, you know, just ironing my shirts, hanging the ones that smell like smoke out outside, so I can get another so it was, I forget what your original question was, but

David Novak 16:40 

you're basically saying that you had no out. You know, this

Chris Riccobono 16:44 

is that no out. So it had to succeed.

David Novak 16:48 

So you didn't come from the fashion industry. You can't send out these shirts with no but the buttons won't stay on for long. I mean, how do you build your know how? So that you could start making quality products and make the smartest decisions in a very, very competitive category.

Chris Riccobono 17:04 

What we knew we had was an idea, and the reason was, even though we were selling terrible shirts, even though we had no money, and even though we weren't marketing, we were doing some PR. Anyone who, who will go to our site, would send us personal emails paragraphs, I've been wanting to do this. You're saving me this and that like, and we're like, this is crazy, the passion these people have for a shirt. So we just have to get it right. So I found a guy named Bjorn who is a true fashion guy, like he knew how to make shirts. Now, one point I will make, and I think is as a general point to entrepreneurs in any new industry, I'm successful because me and my partner did things differently than what was done in fashion, and we were doing things differently because we weren't Fashion guys. And the amount of times we'd have people come in who were 10 year J Crew people, or whatever they may be, and would say, you can't do it this way. This is not the way. And we'd say, well, it should be done this way. There's so that was actually a benefit, but I did need someone to help me make a great shirt. And we brought in someone who connected us to all the great factories. We started making a great product. And in 2015 we had about $30,000 left in the bank account. We're making a great shirt now. But no one knew about us. So he said, Let's try to market so he called up the local radio station, Boomer and carton sports radio. They said, Listen, you're going to need about 200 grand. And just so, you know, it's going to take a few months. That's the way marketing works. And we said we have three weeks and we have 20 grand, this is all we can do. So just run the commercial. And it was this shirts design, you know, you ever have a problem, you know, finding a shirt that looked good, untucked, and within five minutes, there's 4000 people on a site, and this is off of a radio read, no one markets on radio with fashion, you got to see the product, but it worked any so then we went to airline magazines. You're the only brand we were in airline magazine outside of a watch or perfume company spent 15 made 45 and and then the rest is history. We just started ramping it up. And then it resonated with people. You

David Novak 18:56 

know, you do a great job in your commercials. You're in all your commercials. Now, why is that? You know what made you do that? Two best decisions

Chris Riccobono 19:03 

ever made. One was naming the company on Tuckett, which everyone said was a terrible idea, and I can tell you 100% we wouldn't be where we are today if it wasn't named on Tuckett. Number two was this first commercial we ran, which Adweek actually just wrote an article on it, like 10 years later. So we had no money. We couldn't hire people to write a commercial. So he said, Let's just try to I want to tell my story of why I'm so passionate about these shirts to see if other people have this same problem. And there's no better way to do it then. Let me just tell you it right? Let me just we have no budget for a commercial. We have 50 grand, so me and my partner wrote the script. And it ended up, I don't know if you've ever seen this one, I'm walking down in Soho, and it became the most dramatic commercial, not by it just somehow got there where the music in the beginning you think you're watching a pharmaceutical drug commercial on some major cancer disease, and then it's me walking dead serious because they said walk like you would walk to work. And I'm always thinking, and I'm not smiling. Island, and I look kind of unhappy, and I'm saying my problem is I couldn't find a shirt. So I'm all these problems in the world, and here I am talking about my problem being I couldn't find a shirt meant to be one untucked. You go on Twitter the first day it runs and there's death threats. I mean, this guy should be dead. Someone's This is a horrible guy. His only problem. I'm thinking, they don't, don't they realize that I'm just trying to sell a shirt. And when it played in the background, you'd go, and you look, and you say, what is this guy doing? He's really this passionate about a shirt. And that commercial did to this day. Anytime we make a new commercial, it does 10 times better. I think we've overdone it now. We've overrun it, and we're pulling it for good. You know,

David Novak 20:42 

Chris, you are one intense guy. You know, you say you don't smile. You know, you're smiling now, because I guess you're looking back at this. It is kind of funny, but you are intense. You attacked the business with a incredible daily intensity that I can see. You know, how do you manage that intensity? I mean, how do you keep it in check.

Chris Riccobono 21:02 

I like to say passionate, because it's funny. You'll laugh at this story the first time I I'll tell you this story later, if there's time. But in my journey to get Derek Jeter for greatness wins, I remember his accountant, who's this nice guy who lives in Michigan, he called me separately, and he was trying to say in a nice way, he goes, you know, you're like a bull in a china shop. I was like, Dave, I'm a nice guy. I just get when I get on the phone, I get or when I get on the Zoom calls. And I'm telling you why we should do this, I just get passionate. Listen, it's hard not to, when you're when it's your own brand, you know, you're thinking about it every second of the day. And I you know, you just want to be successful. So, like, I'm, if you talk to my employees and we talk about leadership, they think I'm very quiet, like when I go into the office, I'm I'm subtle. I'm not someone who who's barking out orders. I just like to lead by my passion. They see how much I care about this business, which really defines my life. If you think about, I mean, I'm 45 I started in 31 anyone who sees me, I'm known as untucket, right into the untucky like it's kind of odd that untucky, this strange concept, defines my life. So it is important to me. But I think from a leadership just tying back everything to being a leader, this is not the way I talk to my team. In fact, sometimes I wish I did. It's more about how when I'm talking about the brand, you know, them, and I'm talking about what it takes for us to be successful as a brand. I get fired up a little bit.

David Novak 22:23 

And you are, Chris, a hell of a brand builder, and you say that, and I quote this is you say you need a hook. If you don't have a story to tell, you're not going to survive. You know, you've talked a little bit about this, but can you unpack that belief for me a little bit more? Yeah,

Chris Riccobono 22:39 

there's just so many entrepreneurs who come to me and they pitch their whole idea, and it's really like, they say, I'm going to make a better, you know, hat, and it's out there. I'm going to make a better couch. I'm going to, well, how are you going to make it better? Well, it's just going to be better. You know, the fabric is going to be better the well, that's everyone does that, and everyone says they do it. You need a real you need, you need to solve a problem. And if you're not solving a problem, you need to convince the customer that they have a problem that they didn't have. You know, I always laugh. I have a lot of customers who will come up to me and say, You've convinced me now that I do need a shorter shirt, even though I don't think I need a shorter shirt. But now I'm starting to think I do. When you go through Instagram at night, if you type in on tuck it today, by tomorrow, you're gonna get followed by 25 different brands. They're all going to look nice. They're all going to have nice looking models. If you don't have something in there that differentiates you. You might be a $25 million brand. You might be a 3040 but eventually you're going to reach a plateau, and you're going to need to spend so much money on marketing to continue. You're going to realize you need to be profitable. You pull it down, you're going to disappear. You need to build the brand, and that's the real differentiator of untuck and why we're still here and so many people aren't, is we became a brand. It's the most important thing. And you need the customer to feel like you need the product, not just want the product. You

David Novak 23:53 

know, when you were a GE you were in sales, and I'd argue you're you're still in in sales, even today. You know, what do you wish more leaders knew about the art of selling that could really help them, regardless of what industry they happen to be in.

Chris Riccobono 24:07 

You know, for me, my success in selling at General Electric was just relationships. I was always a big believer that relationships. As long as you have a good product, of course you need the product and to be the best. It's all about relationships. My job now, selling is a little bit it's like more of a selling, marketing role. You know, I got to I still, like you mentioned, I do a lot of my even for greatness wins. Now, I do a lot of my own stuff, and I do it because I feel like I could tell my story better than anyone else can. And it's going to come across as being passionate, that I really love my product and it really is better than anything else out there. I think that's what makes you a great salesperson. I mean, it's like you said. I mean, it doesn't take long for people to realize, you know, a lot of people say I'm intense, but it's really just passionate about the product. And when I'm out there marketing on Instagram, you know, most people will put in models, or they'll hire. Actors for their brand. It's not because I want to be the face of the brand or I want to be everywhere. It's really not the reason. It's because I just feel like I'm going to convince you, if I can tell you why untuck it makes the best shirt or greatness wins, makes the best workout apparel. If you give me a minute, I'm going to convince you that it's different and that it really is worth trying, and I just think it's more believable when it's coming from the person who created it. Now, when

David Novak 25:25 

you're an entrepreneur, you quickly realize that you can't be a one man band. I mean, you have to build your people capability. You talked about how you brought in the quality expert that helped you and untuck it. When you think about, you know, hiring people, and you look back, what was the biggest hiring mistake you've made is as you were learning how to bring in the right people? Well, the

Chris Riccobono 25:46 

first thing for an entrepreneur is willing. You got to pull back a little bit, you know, because you want to touch everything. I mean, at one point, I was the head designer at untucket. I'm not a designer. I don't know anything about designing. And it even got to the point that that I didn't stop doing that, until a few years ago, where I wanted to see every single thing we made, and I used to laugh, because I'd be like, I'm not even a designer, like, I just like what I like, and what I like might not be what other people like. So I have to relinquish control. That's a problem that all entrepreneurs have, is relinquishing control, because you got to give what these these people are experts in their area, my merchant, my planner, my head of Ecom, my customer retention team. They're experts. I'm just an entrepreneur learning. I learned all this on the fly. So I think that's, you know, the first thing is that you have to trust and you have to bring in some really key hires. I've have a great team that the thing that's interesting about my journey is we were the first, second, third. I don't want to say first. We weren't the first, but we were in 2011 there was no one else really selling direct to consumer clothing, other than bonobos, which is a brand, and I think Warby Parker had just come on board. Everything was new. Everyone was learning. So my team that's been with me for a while. They're cutting edge. They were there before any they've learned. And we all learned like no one knew how many emails you should be sending out, you know, what kind of imagery should you have all of these things that now feel like it's the norm? How much money should you spend on Facebook? Should you market on Facebook or TV or, you know, all this was new with E commerce, which is brand new. So I have a lot of experts who a lot of these companies built their platforms around, untuck its feedback as to what we were seeing out there, and all this new technology has come out in the last 12 years, stores and how to work with stores and E commerce, that's brand new. 14 years ago, I don't have any hires that I remember. I think you said a bad hire. I do have a lot of great hires, and for me to hire you, you have to have a hint of entrepreneurialism in you, because I can't have someone coming in the company as you're growing it and only doing what you're trained for. I need you to come in and it's all hands on deck. If you find other ways that you can move the needle, and you're a merchant, I want to hear about it. And that's the entrepreneurial mentality as someone who, like me, who had to learn finance, marketing, all these different things. So I want my employee a lot of corporate jobs. You hired persons for just what they're supposed to be doing at untucket, I want to hire someone who can add value in other areas. You know as well.

David Novak 28:17 

We'll be back with the rest of my conversation with Chris ricano In just a moment. You know, Chris mentions the eyewear company Warby Parker as another brand that found early success in the direct to consumer space. I love talking to their CO CEOs, Dave Gilboa and Neil Blumenthal about the incredible focus they've developed in order to turn that initial success into a lasting brand.

Dave Gilboa 28:41 

I think what we found is that regardless of how a big company gets, regardless of how many employees and how much capital is available, that focus is so critical to success, and so we heard early on, that strategy is what you say no to that's something that we've really taken to heart, and often counsel other entrepreneurs, other founders, to really define who you are and maintain ruthless focus just on that and say no to everything else. Go

David Novak 29:14 

back and listen to my entire conversation with Dave and Neil Episode 181 here on how leaders lead.

This business was just skyrocketing. You get all these bids in north of $700 million you know, then covid hits, you almost go bankrupt. You mentioned, you know, when your business tanks like that. How did you manage your mental state? How'd you stay positive? I mean, what was it that you did to work yourself through that kind of adversity? I

Chris Riccobono 29:51 

can't say it wasn't hard, because first of all, it's never been. And by the way, I there's millions of people who went through what I went through millions. So I don't want to say. Tell the sob story. But what we didn't have was a blueprint. You'd wake up. I'd put on the news every morning, the Today Show, funny enough, and the today's show, because I wanted to see what, what was their spirits? Were they down? Were they depressed? Were they negative? And then I could say, Where were, you know, How far away were we from getting through this? The problem is, no one knew the answer, that covid might be around forever, might be around forever, might go away, might so I'm sitting here saying My dad always has this saying that. He says, This, too shall pass. He goes, this, too shall pass, son. You know, that's what is. But in this case, we didn't know if this was passing. And then I was like, there's no one. I can't call my dad and my dad say it's gonna be okay, right? No, don't. Or call a business leader, and that business leader, I remember, I used to get on the phone with a guy named rich handler, who's the CEO of Jeffries, and I would call him, and he was just so helpful during this time, because, like, I don't know what to do, and you couldn't do anything right? There was nothing you can do. It's there was this phrase going around, which I love, could control the controllables. It was incredible. I was watching this thing that I built, and did everything right. And I don't say that arrogantly, everything was done right? It was ready to sell. I had, quote, unquote, made it. I brought it from start to finish, and now it was going bankrupt. I mean, I remember getting on the phone with the bankruptcy attorney, and he goes, guys, this is why bankruptcy is there. It's for companies like you. You have $80 million in accounts payable. You have 70 million in debt, and you're not selling a lot of product. You got to give I said, What does it mean if you go bankrupt? Well, it means you no longer are part of untucker, and you no longer get a salary, because they're going to walk you out the door. That feeling I didn't tell my family, just on a side note, because I couldn't get myself to because I didn't want to worry about me. But it was crazy. I mean, it was really you call your partner. We always had a solution. You know, one of these things, there's always a solution. There was not a solution here. You know what? I mean? We couldn't sell the product, and it was terrible. Now, we said, we can't go bankrupt. That's number one. I don't care what we got to do. So we started reaching out to all the factories and all the different people, and they believed in us, they believed in our brand. They believed that we were going to be the perfect brand post covid. And they all, they all hung with us. You know, we got all this brought all this debt on, so we survived. Listen, it's never been seen before. I remember this is used to be interesting. You go to sell the business, the first thing they say is, what? What happens in a downturn? Do you guys survive? And you'd always say, Listen, a recession, of course, we survive. People need shirts. Yeah, we might take a 10% hit, a 15% hit, that was worst case in the old days, a recession, right? That's worst case scenario. Now, worst case scenario is we're going to close your 90 stores and no one's leaving their house. I still look back on this thing, it's just hard to understand forever. This is going to impact on tuck it, because, like I said, it then drove to us having a lot of debt. Add in another problem, interest rates go from eight to 13% if interest rates stayed at 18% but covid happened. I'd have a lot of cash right now. Instead, it went to eight to 13% on all this debt. We couldn't refinance, because no one can refinance. So it's one crazy you stop me. So is this a joke? This has to be a joke like this is crazy. Here we are year four, and even though we were profitable, we turned significant, not significantly, profitable. We did $16 million in EBITDA. There's not a lot of companies doing that in our space. Most are losing money. We pulled our marketing down $30 million and still grew, and we're profitable. Problem is our cash flow is not because we're paying 15 or 60, whatever the number is in interest. So I'm still going through it now, believe it or not,

David Novak 33:16 

I love your honesty, Chris. I mean, sometimes it's a bitch, and that's basically what you're saying, and you're working your way through it. And I love it, you know, but

Chris Riccobono 33:24 

it makes the story better. Yeah, that's what kept me going. I literally said that's okay. I said, One day I will be on a podcast or write a book or whatever it's going to be, and when I do eventually sell this thing, what a bet, maybe a movie, because what a better this four year period just makes the story more interesting, you know? And that's what I'm telling myself.

David Novak 33:43 

I think Netflix is going to listen to this podcast and you're going to be making a movie, you know. Hey, you know Wayne Gretzky, as I understand it, was one of your investors in in untucket, you know? And he famously has that line, you you need to skate to where the the puck is going. How are you thinking about the evolution of untuckit to make the full rebound, to have this success story that you're looking for.

Chris Riccobono 34:06 

It's a great point, because originally, we didn't have to do anything but make a shirt designed to be worn untucked. That's what we were. We had first mover advantage. It got us to where we needed to be. Now, four years later, there's been too much time. A lot of new brands have come in, so we have to rely on all these other great things that we have about untucket, which is our 100% quality control. We have an incredible high quality product. We have an incredible customer service team. So we are now expanding, you know, we're, for the first time, we're marketing. We have, we do, you know, 80, $90 million in non button down shirts. No one knows that, right? That's a business that we don't market at all, and we still do that level of volume. So we're going to market that. The exciting thing about untucket is we have zero wholesale zero. There is no brand doing our volume that doesn't have a significant portion of wholesale. We're going to start to go into wholesale. We just went into big and tall DXL. They're having incredible sell throughs with us.

David Novak 40:00 

Use to keep them in sync with where you want to take the business, or do you just go with your gut? I mean, is this something that you have to even think about? You

Chris Riccobono 40:08 

have to like Derek. So when Derek, I offered him an equity deal that wasn't very high because I said, I just need to use you a little bit. We'll say you're a founder, you know, he goes, I'm not doing that. He's like, I want to be really involved. I said, Oh, sure, you do. So I was like, you know, I thought he was doing it just to get the equity up, you know, I want to be involved. Before you know it. I mean, he's calling me all the time, like, complaining about little things that you would never know. You know, the fabric on the women's sports bra like Derek, you really, you know, and that's great. Like, he cares. He wants to be he's, you know, we touch base weekly. Any major decision he needs to be involved in. He's creating this golf short right now that feels like a workout short that he likes to play in. And he's really so it's great. He is really involved in the bit. Me, he is a founder, and that's really important that that comes across, because misty and Derek are founders. We are on the board. We talk regularly. Derek was one of the most successful Nike off field athletes ever. He knows products. He's very passionate about the materials. So I think that's a really important thing to come across to the consumer, that he's not His name's just not on the on it, just to be on it. You

David Novak 41:13 

know, you mentioned these guys are leaders. They know how to carry themselves. You know, what do you think distinguishes you as a leader that gives you the confidence you need to win in such competitive categories. I've

Chris Riccobono 41:25 

always had this confidence and I, and I'm very clear to say, not arrogance, confidence. I just, I was never the smartest guy in the room. You know, it's just never was. I was never, I was a hustler. I just was never the guy who was, I don't know how to say it, but I was I would openly know that I was never going to be the smartest guy in the room. So how was I going to become successful with all these other guys? And it was just the confidence that if I worked harder than anyone, how could I not succeed? And that's always my advice to people who feel the same, and a lot of people don't want to admit that they're not smartest person in the room, but I was always very open about it, but I would always say, but I'm gonna outwork you, and I'm going to find a way to be successful. I'm gonna scratch and claw. So one other thing to add, you need a lot of luck in life, like that's anyone who says that you don't you need all these things combining, because you could do everything right and not succeed, like happened during covid. You need luck. You need to be Right Place Right Time. You need to appreciate that luck and accept it, because that's just the way it is. So So, yeah, I just think hard work, resilience and a little bit of luck, you know? Because listen, if I launched on tuck it today, who knows where it would be. I happened to launch it back then,

David Novak 42:37 

and now, Chris, you do have these two amazing brands, untuck it. Greatness wins. How do you prioritize between the two? That's got to be hard.

Chris Riccobono 42:46 

Yeah, it's it's just working extra. I always say this to whoever you know I'm talking to, if it's a greatness wins team or UNK it, it's just, I'm still working the same. I'm working a lot of hours. I love doing it. It's the only thing I think about. I take my notes middle of the night, you know, stuff that comes on my mind, and I'm always thinking about both brands. And the funny thing is, this is interesting. The amount of things I learn about greatness wins that help untucket, you know, because the way I'm thinking about things differently is incredible, you know, or vice obviously on tuckets taught me everything I learned about greatness wins, but it works. It also gives me a sense of what's happening in the market, if there's a down period or an up period. So I work equally hard on both brands. Obviously, listen, untuck it's my company that will determine my future for now, but I'm passionate about both brands, and I spend, you know, a lot of time on both of them.

David Novak 43:41 

And you have investors in both brands. I mean, how did they feel about you going two ways?

Chris Riccobono 43:46 

Well, that's a good question. Listen, I when I said to to my team and Elon Musk, not that I'm Elon Musk. I don't even want to compare my name his success. But you can go on and on. All these guys are on 234, working. 234, companies. You know, the CEO of Twitter, the CEO or the founder of Twitter, the founder. You can do other things. It's all if you're willing to work. You know, you're 18, 1618, hours a day. You can do other things. Listen, the amount of marketing that I do for greatness wins that I say I'm the founder of untucket. That's an ad for untuckit, right? So I get this question a lot, obviously, from each team. It sounds

David Novak 44:20 

like you're, you've got some rationale that works for you, for sure. I don't know if it works for all your investors. I was

Chris Riccobono 44:27 

hoping you didn't bring that up.

David Novak 44:29 

That's just not the way it works. You know, so much of what entrepreneurs love is and you've, you've really conveyed this in this conversation. And I love the way how you attack your your business, and you love trying to figure things out, you know, measuring different specs and all this yourself. You know, ironing shirts. It's an amazing story. And, you know, but you continually learn what should be the biggest thing that you've learned in the past year?

Chris Riccobono 44:54 

Oh, gosh, there's so many things I'm learning here every year with this, you know, and I'm. Mean, I hate to give a boring answer, but it's, it goes back to, you just can't control so much. It's control the controllables. I mean, I know I learned that four years ago. I learned it three years ago. I learned it two years you know. And here we are, you know. Now we have a crazy election going on. It's just, it's never going to be easy, it's never going to be perfect? The landscapes never going to be there. What is 2025 going to bring? Supposedly, interest rates are coming down. You're going to have a new pre you're have a new present either way. But what's it going to be next year? So you can't sit there and say and just say, Oh, it'll get better next year. You have to find ways to adapt to the business at that time, like you asked about Ontario, we're making a lot of changes right now, just to continue to adapt, to separate ourselves, to improve ourselves outside of our current marketing focus, we have a lot of little things we'll be announcing, from Ambassador roles, you know, from expansion, you can't blame the environment, right? You can't think the environment one day is going to be good, because it's, you know, yeah, we had a great period. And from 16 to 19, there weren't a lot of things happening outside, you know, that were impacting our business, but they happen, and you just got to adapt. And you can't blame you. Just got to control the controllables. And I said it a few times now, but I think it's a great piece of advice.

David Novak 46:11 

You know, this has been so much fun. Chris and I want to have some more with my lightning round of questions. Are you ready for this?

Unknown Speaker 46:18 

Okay,

David Novak 46:18 

all right, what three words best describe you?

Chris Riccobono 46:21 

Resilient, dedicated, passionate.

David Novak 46:26 

If you could be one person for a day besides yourself, who would it be? Think

Chris Riccobono 46:30 

I'd have to go with Eric Church, like we talked about be up there playing

David Novak 46:35 

What's your biggest pet peeve?

Chris Riccobono 46:38 

It's people who don't have incredible attention to detail.

David Novak 46:41 

Who would play you in a movie? Oh, gosh,

Chris Riccobono 46:45 

maybe, uh, maybe Bradley Cooper. I'd like to think

David Novak 46:50 

everybody would like to think that, yeah, exactly. You played four years of division one tennis in college at Providence, so let's just say you play one set at the height of your skill level against Carlos alcarez at Wimbledon. How many games would you win? Oh,

Unknown Speaker 47:11 

gosh,

Chris Riccobono 47:12 

I never had a great serve. That was my problem. I don't want to He's good. He's really good. The

David Novak 47:21 

fact that you actually have to think about that, you know, tells me how good you must have been. You know what's something you'd only know about New Jersey if you're a native New jerseyan.

Chris Riccobono 47:33 

It's got incredible beaches, and every you know you're from the everyone Hamptons, Hamptons, Hamptons, the Jersey Shore is beautiful place.

David Novak 47:41 

If I turn on the radio in your car, what would I hear?

Chris Riccobono 47:44 

You'd hear Eric Church or Kenny Chesney.

David Novak 47:48 

I'm going to introduce you to Eric Church. He's he's gonna love you. Okay, what's something about you? A few people would know. Well,

Chris Riccobono 47:55 

it depends who my friends would know stuff. But maybe people in the business, like you've said in this podcast, a lot of people think that I'm maybe a little rough around the edge. It's intense and like he called a bill in a china shop, but I'm pretty quiet guy, to be honest, in my personal life, so I think I just get very excited when it comes to business. What's

David Novak 48:14 

one of your daily rituals? Something that you never miss?

Chris Riccobono 48:18 

Working out. I'm crazy about working out, lifting and running is the only thing, because I drink too much wine. So we're probably drinking wine too. I don't miss that often.

David Novak 48:27 

All right, that's the end of the life. You got good job. Bradley Cooper, you know, you have four kids under six years old. What's something you've learned leading brands that you've carried into to how you lead at home, I

Chris Riccobono 48:41 

just kind of teach my kids. You're always teaching them that this stuff does not come easy, the amount, it's more than I'm just teaching them about this journey. It's all this, how hard, listen, life's hard, works hard, and it's important that they know this, you know, they see the shirts they think I'm, you know, make the greatest shirt. They don't realize. So I'm always reminding them that this stuff does not come easy. This is a battle, and they're too young to really pick up on that stuff, but I'll be sure to be telling them that this is it is hard, and you can't exaggerate. Everyone knows that. I mean, being a I always tell these young people when I graduate college, I don't say it's this is gonna this is tough, and I don't know if it's tough. Listen, you probably have the same stories as a young guy, and it was just different things, but for the last five years, it feels like I would say couldn't be tougher, but I'm sure it was. You've been through different stock market credit cards, so it's not easy. That's the lesson I'm trying to teach my kids. And you got to work hard. And

David Novak 49:32 

I think business. And as you move up, everybody has their challenges. For sure. What's your unfinished business? Chris,

Chris Riccobono 49:40 

I want to sell and tuck it. I was there. It had happened, you know, and then it didn't. And I want to build this. I want to be so that I never forget when Kleiner Perkins, who's a tech investor, invested in us, they said, We're investing in you, even though we never invest in closing, because we think that you could be the next great American brand I think of as the greatest American brand. Polo, while. Because they served all ages, kids, grandparents, right now, four generations will wear our shirt in one house. They send us pictures all the time. I want to be a brand that's known forever. I want this brand to be here in 3040, 5060, years, and I really believe it will be and can be. So I want to leave a real mark on the fashion industry. And of course, I want to sell the business not, not because of the money. It's not because, I mean, listen, making some money would be great, but to me, that's like completing what you set out to do. How could you sell your baby? It's a good question. Listen, the way my I'll have a new one. I mean, right now I have two, I have a new one, kind of, but I'll find another one that I that I'm passionate about. And, listen, it's been a long I'm gonna say it's been 14 years. I know it'll be another, you know, three to five to really get this thing. I'm not selling this thing until we get it to where it should be, which is a north of a billion dollar brand, which is what our goal has always been. So, all right,

David Novak 50:51 

you know, last question here, what's one piece of advice you give to anyone who wants to be a better leader?

Chris Riccobono 50:57 

I'm just gonna stick with my theme, that if your employees don't see the passion that you have for the brand, and don't see how hard you work and how much you care about the success of the brand. And I used to be told that by my employees, when I first started hiring them and went to two to 10 to 20, that they would get motivated just seeing how much it meant to me. So I think that, and that's in corporate America too. I've had many bosses in corporate America. If you see how much they care, they really care about the success. You're naturally motivated and want to work for them more and harder.

David Novak 51:32 

Well, Chris, you obviously care, and you obviously have a lot of irons in the fire. And you know, you're building two great brands, and it sounds like you have more ideas than that incubator of yours. And I want to thank you for taking the time to share your thoughts on on leadership with me. I appreciate it very much. Thank you.

Chris Riccobono 51:51 

Thank you very much. I really enjoyed it. Applause.

David Novak 52:00 

Music. Now, if you haven't seen it, or if it's been a while, you got to go back and watch the original untucker commercial, just so you can see the look on Chris's face as he's walking down the streets of Manhattan. Check it out. It's on YouTube. His intensity really shows. But I hope you can see from this conversation that what looks like intensity is really just passion for his products and his business. Now, we all express our passion in different ways, but listen, when you authentically believe in something, you gotta let it show. It might be a product or an idea or an initiative, but your passion for it will get people on board, and it'll help you navigate the ups and downs that come with it, too. So this week, ask yourself what you're passionate about in your work right now, how do you express that passion to the people around you? Take the time to do it and examine yourself. So do you want to know how leaders lead? What we learned today is the great leaders understand that passion is powerful. Coming up next on how leaders lead, I'm sitting down with John Mackey, the co founder and former CEO of Whole Foods, the man who created a new category in that segment.

John Mackey 53:20 

A lot of people won't like you when you're authentic, and that's why most people aren't authentic, because they're worried people won't like them. But the thing is, the people that like you, they really like you for who you are, not for who you're pretending to be.

David Novak 53:33 

So be sure to come back again next week to hear our entire conversation. Thanks again for tuning in to another episode of how leaders lead, where every Thursday, you get to listen in while I interview some of the very best leaders in the world. I make it a point to give you something simple on each episode that you can apply to your business, so that you will become the best leader you can be. You