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

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It comes off the boat in New York.

You open the boxes and what?

You see right away that they're not good?

Well, actually, when people started wearing them and saying that they now used it for a rag for their car, that's when it really—but you know what's funny?

You know what's funny?

I didn't—we thought through it and said, you know what?

We'll one day get them back.

We'll keep a list of those people, and I'm going to lose X amount of customers.

I mean, you didn't have a choice.

This is entrepreneurialism.

You just have to survive.

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

i'm guy ross and on the show today how a guy who knew nothing about shirts rolled up his sleeves and started untuck it a brand that seemed like a gimmick until it started a trend some brand names sound like they could be anything uber could be a band the skincare brand jack black could be a whiskey.

Bull and Branch, a law firm.

But then there are the brands that wear their purpose on their sleeve.

Fresh Pet, Butcher Box, Paperless Post. You know exactly what you're getting.

And that's the direction Chris Riccobono went with his company, Untuck It.

Just hearing the name, you kind of get it.

It's a shirt designed to be worn untucked.

Simple idea, clever name.

Chris has even said it's the best business decision he ever made.

But in the early days, it sounded a little gimmicky.

Late night comedians roasted it.

Chris even starred in the ads himself, earnestly explaining how he just wanted a shirt that looked good untucked.

And people laughed.

But here's the thing.

Chris was right. It was a real problem.

So real, in fact, that a few years later, big brands were copying the idea.

But naming a company on Tucket was just the start.

To get past the gimmick, the shirts had to be good.

Chris and his co -founder, Aaron Sanandrus, priced them like a premium product, around $80 a pop.

And slowly, they built a brand.

Now, neither of them had any experience in fashion.

They made just about every mistake you can imagine, including a disastrous first run of shirts.

And for many years, both Chris and Aaron kept their day jobs while running Untuckit on the side.

The business was eventually doing so well at one point that it was almost acquired for about three quarters of a billion dollars.

That is, until the deal fell apart and almost tanked the entire company.

But today, Untuckit is once again thriving.

Over 80 stores, a growing wholesale business, and a fast -growing women's line.

And Chris Riccobono, he finally proved that you could build a brand around an untucked, button -down shirt.

Chris grew up in New Jersey, where his dad was a doctor and his mom was a nurse.

He was a standout tennis player in high school, and at Providence College in Rhode Island, he studied finance.

It's funny. I knew I wanted to be an entrepreneur in college because I was scared about corporate America.

got a lot of anxiety in interviews.

I, my first interview I ever did at Providence, my, the guy stopped the interview cause he could hear my heart beating, literally said, I can hear your heart beating.

Let's just talk now.

So I was a very, I was very worried about my career and I kept saying in my mind, I'm going to find a way out of this.

And that was the way I was always approaching post -college.

I was going to get a job and then I was going to focus on finding my own thing.

And I got nervous that how am I going to work my way through up through an organization?

I'm not a great public speaker.

I'm not great at Excel or PowerPoint or all the socializing you need to do to move up.

That just wasn't my thing.

I knew I wasn't good at it.

You knew that you would get to a company because I think you eventually worked for General Electric for quite a while as a sales in their medical sales department.

But you weren't going to stand out because you weren't the most, I don't know, social and maybe charismatic.

you didn't have like i just couldn't do it and i knew it brother right when i started with g and it scared me because then i started saying what am i going to do like i am in trouble i need to be successful i was so into i wanted to succeed in my life i wanted to do something great but i knew it couldn't happen in in corporate america while you were at ge you already knew because you would spend how many years total would you spend there probably 10 but you knew already already early on that you were not going to really climb up the ladder there.

Yeah, just, I couldn't get excited about selling medical equipment.

I guess that's what it was.

I just, it didn't excite me.

All these guys who I worked with, you know, and he had a sales team, he's like 20, 30 people.

They all were openly negative about, they thought I was a dumb guy, like meaning they would say he's just not good, or I didn't work hard, all these different things.

But the reason I wasn't good is because I was totally unfocused.

I was focused on what I was going to do after that job.

Got it. Okay. So you're at GE and I think a couple of years in, you decide to do an MBA program at Columbia while you're at GE.

So a lot of business schools have these executive MBA programs that are like, they take like, you know, 18 months and you take classes on the weekends and one day a week.

And by the way, did you decide to do this because you thought, all right, this is going to help me jumpstart and help me figure out how to start my entrepreneurial journey?

What was that thinking behind doing an MBA?

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 Columbia, I'm 27.

At least I'm progressing this career.

But you're still a GE.

It's a steady job and it's a paycheck, basically, right?

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

I got married in 2009.

But to somebody you met in college as an undergraduate.

Right, right, exactly.

Who's still your wife today.

Yep. Okay, so you're still doing your job.

It's 2008. You've got an MBA from Columbia, and clearly you want out, but you've got to come up with an idea.

And this is a period of time where we're going to talk, we're going to grind through some of these, where apparently you came up with like dozens of different business ideas and kind of trying to see which one would work.

And I guess one of the first ones was a wine blog or vlog, video blog called Pardon That Vine, which was, you would talk about wine.

We're going to get to in a sec, but tell me how that idea came about.

Because I know around this time, I mean, I think a lot of of people who know this world might think of like Gary Vaynerchuk.

That was an early thing that he did.

Yeah, it was an idea.

It was the only idea I had.

So basically put it that way.

And all these other little ideas I tried.

And I also get very bored easily.

So the Columbia MBA got me excited.

I was working really hard. So now I'm back doing nothing again, selling medical equipment, no ideas.

I said, what do I like?

I only like really one thing I'm massively passionate about was collecting and drinking wine.

And I would spend hours and hours and hours reading about it 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, Gary's got a massive following.

I'll be a more laid -back version of Gary.

So I taught myself all this wine.

of sort of filming videos, traveling around the world, tasting wines, interviewing people with this small little camcorder.

They thought it's funny.

I would go to France and they thought that I was coming in with this big camera crew.

And I would come in with my mom or my wife with this little camera and they'd have all these high -end Bordeaux's lined up for me.

And I would do the, they thought I was important back home.

Little did they know 15 people watched the show.

So, all right. So you, you decide to do this.

First of all, you, you were into wine.

It was was just a thing you were into?

Yeah, that story is I was 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, I'm a young kid, I want to be at a bar, I want to be...

I said, fine, I'll come over to have dinner.

And he says, go in the wine cellar and pick any bottle of wine.

He said, pick a sparkling wine.

So I come up, I bring a sparkling wine up, and he tells me 30 minutes about this wine, where it's from, how he found out about it.

We drink it. He said, go down, pick a white.

I go down, same thing.

Then three more bottles of red and the storytelling, and I had an unbelievable night there.

And I said, wow, this is amazing.

Wine is just incredible.

Brings family together.

And that was the day I became obsessed.

I started studying about it, reading about it, collecting it, and that's how I got into it.

All right. So you decide that this could be a cool venture and you called it Pardon That Vine.

But tell me, what was the business model?

Was it going to be ad supported?

What did you how did you think you were going to make money from this thing?

I was thinking I could consult.

I can go, you know, which I did, you know, go consult, go speak at different events, you know, people's parties, which I did a bunch of.

I thought I could build.

Remember, that's once again, right when social media wasn't really out there.

I guess it's like YouTube was new, was very new.

What could have happened to me if I was better at it and maybe technology was a little better, maybe the goal, I would have been that first influencer.

Right. Or, you know, it just never I wasn't that wasn't my thing.

But I guess that was the build up followers.

I remember trying to get followers on Facebook, which there was only Facebook at the time.

And that's kind of before it all started.

So I think the plan was there.

I just didn't you know, yeah, it was tough to monetize.

That's why I stopped doing it.

This is one of many ideas.

I think there were other sort of more short lived ideas like you had an idea for an online dating service for little people.

Yeah. Love for little people.

L4LP. You actually registered domain.

Yeah. I can't get away from this one.

Yeah. L4LP with my cousin.

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

Yeah. And another one that I get told that I'm crazy for today because it sounds odd, 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.

anywhere. And that's, you know, listen, that's the problem with so many entrepreneurs is following through and actually finishing it and doing it.

And a lot of times I didn't do that because I was intimidated and I never did.

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

Yeah. And that's a fun, it's funny.

All these things were happening before it became mainstream today.

So I, it could Could have worked, meaning I wrote with my cousin four different reality programs. None of them were ever made.

But you're right. The biggest thing is it kept me going.

It kept me getting excited.

It kept me kind of pushing myself to try to come up with that idea.

So basically, the blog, the wine blog or vlog becomes your thing for a while because you would go on to post videos, video diaries about wines.

And I'm assuming it was, you know, you would taste wine, you would talk about the wine.

how are you, and also traveling and trying wines, how are you doing that and also doing your day job, selling medical equipment?

I developed a strategy as a sales rep.

I became very close with my customers and I was very open with them.

It's funny, I would tell them what I was doing, that I was 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, that's like they, they make movies about it.

So I was the opposite.

I'd come in and they'd look forward to talking to me.

What'd you try to do?

Where'd you go? What's your latest business idea?

So I developed this ability, which my managers, I think, hated and everyone I worked with that I didn't have to go to the accounts and they still would buy from me.

And that's what allowed me to last at G so long.

Cause as much as they wanted to get rid of me, they couldn't cause I was hitting my number.

But, but basically spending spending as much time as possible on, on this other project.

And, and were you mainly like looking for value wines, like talking about wines that people could go buy at this, you know, at the whatever total wine or whatever wine store they're going to Costco.

What I was trying to do was wine was very, um, the only word I have is like snobby back then.

It's kind of changed young, young people didn't drink wine back then, you know, young people, let's say without money, didn't drink wine.

I wanted to show people that I could wear a backwards hat you know sitting there in a t -shirt and love wine as much as the guy in France does who'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 you know golf is thought of as a way to get ahead in sales right that's always been the case golf and that so to me wine when I would go into these doctors and I knew what I was talking about as a 23 year old with wine they liked me they wanted to go to to dinner with me because I knew wine.

I mean, this is it's interesting because the fact that you were doing this and it was actually in a sense helping you was something very real, but it wasn't a business.

There was no income coming from this.

And now we're coming into this next idea, which is which is shirts, nice shirts that you could wear untucked.

Right. Right. Because any certainly guys know that when you get a dress shirt, they're long.

They're designed to be long because you want to tuck them in and get them as fitted as possible.

And so tell me about this.

We're around 2010. You're still a GE.

You're still selling medical equipment.

You're doing the wine vlog.

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

Well, let's be clear for younger people who are listening to this.

This problem doesn't really exist today because everyone's kind of copied and made a fairly reasonably fitting shirt.

In 2010, every shirt came down to your mid -thigh unless it was an out -of -spec shirt.

And I had one of those.

I had one J. Crew small, I'm a large, that somehow is out -of -spec and it fit me perfectly.

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

Out -of -spec meaning it was a large and supposed to fit one way, but it fit another way because it was out of specifications to what the shirt was supposed to be made if it was supposed to be 25 inches it was 28 inches it was but you know if you measure 10 shirts from most companies and 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 in to the J .Crews of the world and try to find a shirt that somehow fit me at a little bit of shorter length than the other ones did.

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 and all these things that you need to start this company.

And finally, I went to Las Vegas.

I was out with my friends.

I think it was a bachelor party.

Wore the same shirt four nights in a row, became a big topic of conversation about everyone's struggle.

And I'm looking at my friends and how silly they look.

And I said, I got to find a way to do this.

You're wearing this J.

Crew shirt that you would wear untucked.

Wore it untucked because it was a small.

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

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

Yeah. It's funny. Shirts designed to be worn untucked.

Everyone laughs at that.

That's so simple. No shirts were designed to To be worn untucked.

There were not even the ones - Guayaberas, there are guayaberas, for example.

Well, that style shirt, yes.

But that's not what we were making.

The oversized cutoff, which were 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, going back, I know the specs.

I'll bring it up again.

It was a big thing because companies didn't factor in length.

They didn't care 31 inches, 33 inches, 32, 35.

Don't worry about it.

You don't even have to QC that.

It doesn't matter. They're not going to notice.

Because you're tucking it in.

So you're on this trip to Vegas with friends and you start to talk to them and they're validating your idea or your problem.

They're saying, yeah, that is annoying.

They're saying the same thing?

They're validating it, but with excitement.

And usually I'm used to them.

When I bring L4LP to them, they say, not going to work, or you're out of your mind.

Or I bring a video wine blog.

They say, Chris, you don't know enough about, you know, whatever it may be.

This one wasn't, oh, here he goes again.

This was like, oh, my gosh, this is amazing.

And the perfect, the best example was my partner from Columbia Business School, who I brought on, Aaron Sanandras, 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 the straight 800 times, but he sits down and he said, I'm in, you don't have to tell me any further.

I've been, I've had this problem since day one.

This is Aaron Sanandrus, right?

Um, he's your, you meet him at, you had met him when you did your degree at Columbia.

And he, I think was working at Pricewaterhouse.

PWC. Yep. He was a partner at Pricewaterhouse.

PricewaterhouseCoopers.

He was an accounting.

He was someone similar to me in that he would also pitch ideas.

We always wanted to think of ways to start a company.

He's somebody that you...

Just tell me, why was he somebody you thought would be the right fit to start a business with?

Aside from the fact that he had a bunch of ideas, what was it about him that you thought could work with your personality?

He's just incredibly smart, always asked the most questions at Columbia, very inquisitive, very good at multiple things.

I knew that I needed someone.

I couldn't put together a beautiful PowerPoint to go raise money.

It just wasn't my thing.

I couldn't put together a detailed financial model.

And many times there's a guy who can put together a detailed financial model and then a guy who can put together a great PowerPoint.

Aaron was very versatile.

He could do all that stuff.

But when I called him on this and he was that excited, that was the other thing because I finally found someone who believed in this idea.

You didn't know about how to design a shirt.

You're not a fashion guy.

You didn't go to Fashion Institute or whatever.

Aaron is a finance guy.

So let's just talk first about, you know, in a lot of industries, if you don't speak the language, they don't take you seriously.

Like if you don't know what a hem is, or I don't even know the language in apparel, you know, in this kind of apparel, but they have language.

They have a code that they speak in.

that you now know, you know, 20 years later, but then you didn't.

So how did you eventually find somebody who, who agreed to like make a prototype for you?

Well, you're right.

Um, like I wanted to make sure I went into the fashion district.

I wandered in and out.

I brought my one J crew shirt.

I asked them to make it.

They said, I'm crazy.

That's not the way it works.

I said, please make it.

I was meeting with button manufacturers.

And you're talking about the like garment districts in New York City.

You actually went into garment makers and asked them if they could make you a custom shirt.

Yeah. I wandered in the street and looked at places that have sewing machines.

And I went in and I said, can you make me a shirt that looks like this?

You know, I figured that was the first step.

I mean, I didn't know what else I was 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 spec of a shirt and i'd say what are you talking about they're like we have specs right if you make it 20 inches across we then make the length 32 inches i'd say i don't want it 30 i want it 28 .75 inches so the length by the way 28 .75 that's my favorite number in the world that's uh yeah on a medium from the i shouldn't probably be telling people I guess they can measure it, but 28 .75.

And then they, I was just working with these people.

They, some people told me they can't do it.

Some people told me they could do it through each person.

I met someone new and met someone new.

It was really that type of story.

So I just learned, it was like, I was taking my time.

I had a full -time job.

There was no rush. And I was learning.

It took, you know, two years to get to market, you know, to finally get that right shirt.

But that, that, that was the hardest part is finding how to make the shirt.

All right. So already in year one, I mean, you're kind of doing this R &D.

Aaron is working at Price Waterhouse Coopers, but he's on board. He's like, I am in, I will, I want in.

So what was he doing?

He was helping you kind of craft the PowerPoints and build a business model.

Yeah. He was building the, cause we had to raise some money.

We had to build out a website.

We had to, you know, start to think about how to market.

So he was doing a lot of the financial side of things at the time.

I was doing the shirts.

But I'll tell you, things like Untuck It, that name, I came up with that and then agonized it over a year of all these people telling me not to use it.

You know, shirts designed to be worn untucked, that took a year.

You know, you laugh at this, but you realize why some of this marketing stuff means something.

You know, you want to rush it.

Oh, it's shirts worn to be made untucked or whatever, that took a long time.

So we were working on things like that.

And then raising money was impossible.

You go to people and tell them you're a medical sales rep and you're going to go make a shorter shirt, right?

What are you talking about?

How's that? No, it's not a good bet.

It's not a good bet.

Not at all. But before we get to the money side, just going back to what you and Aaron were doing, were both of you living in New York City at the time?

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

So how often were you meeting?

We meet at a diner, you know, two times a week in the city on Fifth Ave. And we just, listen, you never believed that this company, it was a shorter shirt.

This wasn't technology.

This wasn't, I started, I'm going to work on an Uber app, right?

And I'm going to design it.

This was, I'm making a shorter shirt and I'm going to try to to break into the fashion industry.

You never think it's possible.

When we come back in just a moment, Chris and Aaron get a crash course in how not to make a shirt.

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Hey, welcome back to How I Built This.

I'm Guy Raz. So it's 2011, and Chris and his business partner have put together about $150 ,000 to start a new brand of shirts designed to be worn untucked.

And now Chris has to get them made.

I connected to this guy from Poland who had an office in New York City, and he showed me a bunch of fabrics, looked at 100 fabrics, said these are the ones I like.

He said, I'll make them for you in Poland.

No process, you know, no, you know, now you're supposed to do tech packs and big order forms and this and everything automated.

I told the guy, I don't know.

This is all I got. It's me and my partner.

It was such a different time.

So they were willing to do this.

Today, there's thousands and thousands of people launching clothing brands every day because of the ease of doing it now, you know, with the ability to grow.

So back then it wasn't.

So that's a benefit.

I always say I was lucky at the time I did it.

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

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

He was the broker for that factory in Poland.

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

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

And the shirts are going to be made out of cotton, I'm assuming.

Yeah. It was all cotton, basic stuff.

How many shirts did you order in that first run?

Only a thousand. And how much did it cost you?

Probably 20 ,000, somewhere around that.

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

thing? No, no. We were more than that.

I think we were like 78, 88.

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

Well, so the funny thing is we made terrible shirts in the first year.

Like I never really got there until year four of making a really nice shirt because I didn't know what I was doing.

I didn't even know you had to pre -wash a fabric to take out shrinkage.

No one told me. Some of the fabric, we didn't test the fabric.

So the arms on our first plaid grew really big after washing and the rest of the shirt shrunk.

Wait, hold on. So tell me about that first batch of inventory because, I mean, you say that the shirts were terrible, which is shocking.

I'm sure you sink all this cash into it.

You don't have a lot.

When it comes off the boat in New York, you open the boxes and what?

You see right away that they're not good?

Well, actually, when people started wearing them and saying that they They now used it for a rag for their car.

That's when it really, but you know what's funny?

You know what's funny?

I didn't, I thought we thought through it and said, you know what?

We will one day get them back.

We'll keep a list of those people, but we'll get our cash back.

They'll buy the shirt.

They're not going to return it.

Right. They're going to, 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.

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

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.

I brought a UPS printer, and we grew from there.

I mean, we shipped, I shipped every night from my apartment.

But we remained positive because when the guys got the shirts, the excitement.

We'd get paragraph emails from customers who found out about the brand.

Thank you so much. I've been looking for this.

I can't believe I didn't do it myself.

This has been a problem in the industry.

No one writes paragraphs to clothing stores, you know, one after another.

other. Every day there'd be paragraph emails.

By the way, it 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 and the same thing.

It pulls off. Next one pulls off.

I take another shirt.

The factory forgot to tie on the buttons the right way on this machine.

The machine was broken on every single shirt they made.

We sold them. We 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.

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

They were all being made in a factory in Poland.

And not to knock Poland, because Poland today I think would be prohibitively expensive.

It's an industrial power and it's got manufacturing and it's a EU country.

tree. But my obvious question is, why would you keep working with that factory if the shirts they were making sucked?

First of all, you didn't have a choice.

It's much harder than you think as a company making a thousand shirts or whatever the shirts we make.

They just don't even pick up your phone call for a thousand shirts.

The other thing is it wasn't really there.

I'm supposed to be submitting this tech pack that has washing instructions, fabric testing, testing buttons.

buttons. I'm sure they were just, they had a thousand shirts making no money on it, taking a chance.

They're making the shirts and they're sending them over.

I'm just trying to figure out why is this so complicated?

I mean, I'm wearing, as you know, I'm wearing one of your shirts now.

I wear lots of button down shirts.

What's so hard? Why is it so hard?

There's a reason why I found out that people do not make shirts designed to be worn untucked.

Our shirt has to be in spec every time.

If it is an inch too short, you can't wear it.

If is 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 affects it, all these different things.

So we had to implement this crazy quality control process where we're washing each yard of fabric, where we're rejecting it if it doesn't hit spec.

I rejected a shirt an inch out of spec the first time, and they said, that's not the way fashion works, Chris.

They're not going to work with you.

The factory will not work with you.

And I said, Then I don't have a business idea.

When you make a, when your name is on Tuckett shirts, and you're talking about this perfect length, it has to be perfect.

It has to be perfect.

Okay. But I guess the reason why it's not perfect every time is because shirts are still, there's still a lot of human hands involved in each shirt, right?

It's not a machine that's making every shirt.

It's not like it's going on a factory line and it's just a machine that's just cranking it out.

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

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

And that, that was.

Right now think about this.

Like if we're making 15 ,000 white medium shirts, which we do in, they put them into a washing machine, a one, a massive tank, right.

And they dry them and they wash them and they heat them.

If one's too close to the heat and one's a little further or one's that's the other problem when you're scaling it's very hard to make that same shirt at the same length every time and you have two different people making it and all these different things and your promise was hey it's going to look great as an untucked shirt but if it was slightly off or trunked too much or you know or it it the whole thing gets thrown off balance and there's no difference and And then we blend in with everyone else and the idea goes away and we disappear.

Okay. So again, I go back to my question.

If that factory in Poland sucked so much, why did you keep working?

I guess the answer is you had no choice.

It was the only, they were the only ones.

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

How did you do that?

I mean, were you flying to Poland to that factory?

Did you basically, at a certain point, imagine you stopped working with them?

I stopped working with them.

But I also found this Swedish guy named Bjorn, who's still with me today.

Older guy, teaches at the Fashion Institute.

How did you find him?

I was working with a freelance guy who was not very good.

Bjorn walks in for a meeting with him and he throws him the shirt.

And he says, what do you think of this shirt, Bjorn?

And Bjorn destroyed the shirt, says the worst made shirt I've ever seen.

And then he contacted me outside that meeting because he thought there was something there.

Now, the good news is, the good news is, we grew unbelievably slow.

You know, $90 ,000, $300 ,000, $500 ,000.

This is year one, two, three.

Yeah, then, you know, $3 ,000 ,000, $15 ,000 ,000 and up from there.

So that three to 15 was a big difference.

But the great thing was, we always say this.

If I started a company today on Tuckett, I would go raise 500 grand, right?

You'd go out, you have your marketing plan, you market, you ship all your shirts.

If they're bad, it's over, right?

Now it paid social, social media, all these people.

Back then, luckily, we had no money, we had full -time jobs, and we weren't marketing.

So we learned all this.

Okay, your shirts suck.

Okay, we lost 600 customers.

keep their names though because one day I'm going to send you a letter and explain that I agree our shirts were terrible and I want to send you a new one on us which by the way we did that the only reason we survived is because those years we were so small so we were able to perfect the shirt before we became known that's what allowed us to right and by the way that was across one of the reasons I think Aaron and I were successful is we did things completely different than they did in fashion we didn't know what we were doing and we used that to our advantage privilege like you launch spring everyone

launches spring and on March 1st but it's 30 degrees why do they launch spring on March 1st I guess because they've been doing it for 100 years you know it's snowing out and they're showing past that so we were very comfortable with we are not just following this blueprint of fashion right we're going to create our own way and if it works it works and it's going to work because of that and if it doesn't it doesn't the the you had no office right the office was your apartment in Hoboken is it right Yep.

And we did that for a long, we probably did that till 2015.

We were very frugal.

That was my plan. I didn't want to fall into the trap of many entrepreneurs of looking to get this big office, hiring all these people.

Yeah. So you're doing half a million by year three and all online, all direct to consumer sales.

Three years in, you're talking about 2013.

So you didn't need to raise any more money at that point.

You were still able to kind of take the, just operate the business through cashflow.

But I imagine as the demand increased, you know, you had to order more stuff.

So how are you handling the money?

Were you getting loans?

Were you - Well, what happened in 14 - No, we had a line of credit, a little bit, a small line of credit.

But what happened in 14 was we said, we can't keep going like this.

We'll be here forever, you know, growing slow and And let's go market.

We got to market. We had $21 ,000 to spend in marketing.

And we called Boomer and Carton, New York radio show, the only one we could afford. It's a sports show, right?

It's a sports radio show.

They said, you need like three months and $100 ,000 to see results.

And we said, we have three weeks and $21 ,000.

So we did it. And I remember sitting in LA in a hotel room.

First read comes out.

I have my Google Analytics up.

And within, now people are driving.

They shouldn't be going to the site.

But within 20 seconds, there's 1 ,000 people on the site.

Wow. And sales going up, sales going up.

And they read the ad.

Yeah. And were they like, hey, dude, do you ever have that problem where you want to wear a shirt untucked but it looks so stupid?

And the other guy was like, yeah, I hate that.

It's annoying. Well, now there's a – was it like that?

Exactly, back and forth.

And it would end very strong.

Shirts designed to be worn untucked, untuckit .com.

And people were like, must have been, what the heck is this?

you know, because the people would just fly to the site.

And then we booked airline and magazine, spent 15, made 45.

And we could track this very closely because we weren't that big.

You spent $15 ,000 on airline magazines.

Yeah. Okay, let's just pause there for a second, because I actually think that's a brilliant idea.

And sadly, they don't exist anymore.

Most airlines don't produce magazines anymore.

But what airline was it?

Was it United? It was everyone with the Delta United Southwest. We were everywhere.

And the only competitors in that magazine at the time were watch companies and fragrance companies.

So when people saw us there, I think they thought, oh my gosh, this company must be taken off.

Which by the way, that opinion from a consumer makes them convert when they feel that you're bigger than you are.

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

When I launched the company, I thought we were going to be fashion forward 20 to 40 guys who who are actually going to take the time and say, oh, I also have that problem.

It ended up being our current demo today and it's fluctuated over the years, but it's 25 to 70 years old, evenly distributed.

So pretty much every type of guy, rich, poor, you know, taxi drivers, Leonardo DiCaprio, Matthew McConaughey, to athletes, to construction workers, security guards.

That's been why we became who we were.

Well, that's the thing.

Like forever and ever, wearing a shirt untucked seemed sloppy.

It was like, who does that, right?

And there was a shift, right, that began around this time where you start to see people, you know, wearing untucked shirts or you saw a lot of people who were wearing blazers, jackets over untucked shirts that didn't look stupid.

it. No, I mean, I say this not arrogantly, but there's no question we played a role into the casualization of the United States.

I mean, you could wear our shirt into LaBernadine in New York City, LaBernadine being one of the nicer restaurants.

Israel and Three Star, yeah, one of the greatest restaurants in America, yeah.

You could wear it with a sports jacket, and no one is saying, I can't believe that guy's shirt's untucked, right?

And that's what we started seeing.

Guys were wearing our shirts everywhere, and people weren't looking at them being sloppy.

Fast forward today, now all these golf clubs across America in their guidelines say you can only wear an untucket shirt when you're in the clubhouse, if they allow shirts.

So it started to become acceptable to wear our shirt to work, to wear our shirt to nice restaurants, weddings, whatever it may be.

Okay, so you guys are growing steadily over the first first three years.

And then the real breakthrough is when you have some money to go on the Boomer Esiason show.

And I imagine that you picked that show very specifically because it was going to be guys listening to sports radio.

And that's who you thought, hey, this is going to be our target audience.

Yeah, sports to this day has become one of our main areas, whether it was the Masters or Sunday Night Football.

So we started there.

And by the way, then we went to Howard Stern very soon after that.

How did you afford that?

I mean, that's a massive add by.

So keep in mind, we raised about a million three, call it, right?

That's not exact, but...

Mostly from friends and family, not professional investors.

No, all friends and family and doing about 53 million.

Now, the equivalent, I'm not going to name brands, had raised about 200 million.

The only reason we were able to do that is because if we and the reason you say about stern we weren't even nervous if we spent on stern it returned if we spent on sunday night football it returned it always returned this is back then by the way everything's obviously more challenging today and was it just intuitive like hey i listen to those things i like those things you're maybe your partner aaron listens to those things and that was it or did you do like some research to find out hey where where should we go Back then we were big testers.

Test it, move on, test, move on.

Podcasts became the next thing, test it.

We were in the Journal, the USA Today, New York Times.

No one was doing that stuff.

They were just doing paid social at that time because that's where the world was going.

By the way, we had 30 billboards around the country at one point.

No one was doing a billboard, but we had this tagline, untuck it, shirts designed to be worn untucked.

That's all we we had to put we didn't even have to show the clothing so it was a it wasn't you got to think about this it was almost like it wasn't a a clothing brand it was a concept yeah let's let me ask you about the name um i think it works great it tells you exactly what it is what it does you have to explain it it's one word untuck it but there were people who were like that's a stupid name give it a nut like you have an italian last name give it give it your last name it'll It'll sound Italian and kind of, you know, Italian fashion and premium.

Yeah, we had most people hated the name.

I came up with it walking out in front of my parents' storehouse.

And I had not launched the brand or even started it.

And I said, that is why I'm doing it.

Because I came up with that name, I'm going forward with this.

Because I love it. Untuck it.

Like, untuck it is the reason we took off.

I really believe that.

And by the way, the reason it wasn't sophisticated.

That's what people would say.

and they're going to think that the product isn't great, that it's light.

And that is the reason I said, we've got to make the greatest shirt you've ever worn.

It's got to be perfect.

When you open that box, your mindset's going to be, this isn't a super high quality product because it's a gimmick.

That was my fear. So I needed you right away to say, wow, this is an amazing shirt and it washes well and it holds up because of the name.

That was the the negative of the name the positive of the name is now if anyone's wearing an untucked shirt people call it an untucked period they just you know it's like a kleenex and a tissue and a xerox machine um and that that's that's a great moment as a brand and by the way it annoyed so many people in fashion which is right no i get why they'd be annoyed because you're not cool you're not part of that crowd right and there's a there's a snobby kind of elite factor there like they're not going going to invite you to fashion to the fashion week runways necessarily.

And they intentionally didn't all those years, like GQ wouldn't write about us and stuff like that.

Cause they were annoyed that, you know, a non -fashion guy came up with this name that's, you know, not fashiony and you know, people liked it.

So that really the, the, the kind of the turning point really was starting to do these ads and then Stern and then airline magazines.

And I mean, with just a million million dollars raised, you're five years in, and you've you're still working for GE, I think, at that point, right, you still are actually on the clock with them.

And also, how are you just coping personally, I mean, running a startup is a full time plus job, it's a it can be 100 hours a week.

And you were still even when you hit three, $4 million in sales, you were were still nervous.

You still, you still mitigated the risk and held onto your job because you're still worried that this could all unravel.

Oh my gosh. It was so hard giving up that job.

I had a car. I had a job, you know, like you had your parents, you know, say your wife, you know, you're going to leave. You're like, I was scared to say, okay, I officially don't have a job.

I am now an untucket employee.

The worst part was my, it got bad at GE where it would bother me.

It started bothering me that I'd say most people didn't like me.

Now, by the way, they didn't like not because I was a bad guy.

They didn't like me because I wasn't doing the, I wasn't going the extra yard doing a quote, right.

I was leaning on people.

I was, I wouldn't go to the meeting because I was now, like you said, I mean, I'm, I have a business now that by the way, he's not doing a lot.

It was doing, I could think exactly during that period of time, let's say it was doing 7 million, 6 million.

And I was like, but there's a chance here.

So I left in 2015 and I was flying to our sales meeting, which I did not have time for because on tuck, it was now really, really taking that next level.

And in the magazine was a big picture of me.

Shirts designed to be worn untucked, founded by Chris Riccobono. And when I got there, I guess all the people saw it on the way to Phoenix to the sales meeting.

They were on the plane.

They saw you in the airline magazine, your face.

Yeah. And my boss came up to me.

I had a good relationship with him, not the people above him.

And he said, I think it's time, Chris.

It's going to be a tough one to explain that was very scary to me and I um I waited to the I got pushed out like it was um you're forcing me out of here and it got to the point I never forget I was walking to Dunkin Donuts like I do every morning and I said and it hit me really hard I said I this business has to succeed now I'm 30 years if this doesn't succeed I'm married and I'm like I have nothing thing.

When we come back in just a moment, Untuckit grows to the point where it's about to be sold for a huge pile of money until all of its suitors pack up and go home.

Stay with us. I'm Guy Raz, and you're listening to How I Built This.

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Hey, welcome back to How I Built This.

I'm Guy Raz. So, it's around 2015 -2016, a time when two really important things happen for Chris.

The first is he walks away from his GE job for good.

And the second is, Untuck It opens its first brick -and -mortar store in Soho in New York City.

I worked every day on the floor, and I saw this reaction to people that this was something special, this brand.

I was able to pay myself a small salary, and I felt really good.

Now, you know, it's funny.

I actually thought, okay, if this doesn't work out, I think I could go get a job in fashion at least. I could maybe go get a job as a...

Yeah, at this point, yeah.

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

Because you now understood the language, you could speak the language, you understood how the industry worked a lot better.

I mean, now you're probably almost as much of an expert on shirts and apparel than you were on wine.

Right. But I also felt pretty confident at the time.

That store did so well in Soho that one year in three months that I said, we are now going to open this.

That's another X million dollars of revenue.

We're going to open five more.

And then we opened 90 stores in, I think, two and a half years.

Wow. But I'm curious, in 2015, 2016, you know, most brands are starting to move online, right?

So why did you guys decide to open up physical stores?

The reason I went into brick and mortar was because people always say, why did we do it back then?

Even though all these people were yelling and screaming about it going away, I had 70 % of my emails where I'm not buying you until I touch and feel your product.

Part of that was because of our older demo, but we had to do it.

It wasn't a... If we wanted to to be around and exist we had to open a store i that's when i started hiring more people but who was doing all of your before that who was doing the website and who was designing who was dealing with like uh fulfillment for example who was doing that i i had one guy shipping in the storage unit and i would go there an hour at the end of the day it's funny i was ironing through 15 i ironed every shirt that i would come home the worst part of this whole journey for me the entire untucked journey was coming home after being out to dinner and seeing 75 boxes in front

of my apartment door and having to iron them and repack them in the middle.

They're right up to the middle of the night.

Iron, clip them, hang them outside.

But we were very lean.

Me and Aaron did almost everything until Bjorn.

And then in 15, on the way to 15 million, we quickly hired.

That's where it turned on quick.

Wow. Let's step back because you officially launched a store in Soho.

It's doing great. And I think the next year, finally, Aaron, your co -founder or partner, you bring him on to be the full -time CEO. I'm assuming you're just like, I'm done.

I don't want to be doing the CEO job.

I want to move to another role, focusing more on maybe like product and creative creative and other things?

To be honest with you, I recognize that he had a better history to be a CEO, you know, as a partner at PwC that would give him a lot more credibility when we were going to have to eventually do a big fundraiser or sell the business.

I wanted him sitting there as a CEO, but I wanted, I thought that was, and I think it ended up being a great decision.

It just made sense to the business.

And you probably didn't have any management training, I mean, management is a skill that is developed through training, largely.

It's very rare when someone's just a natural manager.

manager. I agree, and I am not.

You know, I kind of, if you think about it, one of the reasons I left corporate America was to be alone.

That's going to sound weird, was to be alone working hard, right?

I told you I didn't like feel comfortable in those PowerPoint presentations, in those cocktail hours, in those smooth, like, I just like to be working, you know.

So it was never my, it's funny, like Aaron's does most of the talking in those scenarios because I, he's just better at he kind of went through that pathway to his career.

Let me talk about about ads and marketing for a moment, because one of your ads is a, it's an ad of you walking through Soho.

And it's very serious.

And of course, you're wearing an untucked shirt.

And you're saying I had a problem.

And then I solved the problem.

And I don't think I need to tell you, I think it's a good ad.

I mean, you're an entrepreneur, you're talking about this idea you had, but there's something about the ad that's polarizing which i actually don't think is a bad thing because it got more attention than it probably would have gotten if it wasn't polarizing like it was a youtube ad i mean this ad has been parodied on colbert it's it was in so i have um letterman and and seinfeld seinfeld you know saying i just hate that untuck it guy you know walking down the street all smug then letterman's Letterman's first appearance back after not having been on, after leaving.

His first line, where have you been, Dave?

What have you been doing?

I've been looking to find a shirt that looked good untucked.

Then you have Kimmel Colbert.

Jim Gaffigan has an entire thing in his skit, a very funny thing about the untucked shirt.

All of that, that is amazing, that stuff.

It helps you. You're right.

Everyone would pick their head up.

Everyone would pick their head up and say, what is this lunatic talking about?

Why does he care so much about his shirt?

All right. It's 2017.

Up until that point, you could not actually get any professional VC money.

And this is a time I should mention we've done these – on this show, we've done Stitch Fix.

We've done Bonobos.

We've done many of the brands that you've mentioned but also just apparel brands too that did – were able to attract money from outside investors.

investors. Tell me a little bit about before 2017 trying to I mean, how hard did you try to get money from from venture capital firms?

We were able to grow without raising money, which was very odd.

So we were trying to avoid it at all costs.

I see. You know, I look back.

I don't know how it was possible that we opened up 30, 25 stores without having raised money from that initial fundraise.

It really was just refunding the business.

We took some debt. We did take some debt.

Yeah. Our first big fundraise was, we went out in 2016 to Venture Growth Funds and Kleiner Perkins.

They do not invest in untuck it type companies.

They invest in Uber, billion, billion dollar tech companies.

Then they were looking at us more like a marketing tech company than apparel company.

And I'll never forget, they said the reason they invested is that they thought we'd be the next great American brand.

I just never forget that.

We raised $8 million from them.

That's all we put on to bring us to what would have been our sale in 2020.

We would have had $8 million raised or $9 million lifetime.

So I thought that was pretty cool.

So Clyder Perkins put in, you said $8 million?

Yeah, they put in more, but it was secondary.

It went to shareholders.

But in 2017, I think you raised a total of $30 million.

Is that right? Yeah, from Kleiner.

Eight went on the books.

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

Yeah. So you had worked up until that point, but you presumably wanted some security at that point because you had been grinding and always nervous about what this was going to go under.

and finally, you could take some cash off the table and put it away for a rainy day in case it all went haywire.

So, that must have been pretty great to be able to do that.

It was a deep sigh of relief.

I mean, it was one of those moments that you don't forget, and it was more not because of the money.

It was more of the achievement.

Wow, this really happened.

I got something out of this.

I got something. I started this silly idea, and I I was able to monetize it and say that it worked.

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

Yep. All right. By the time, you know, Kleiner Perkins is putting money into the brand and you're hitting, you know, $50 million a year and you're starting to really build out stores, you know, the other established apparel brands, especially men's apparel brands, clearly have noticed you.

In the first couple of years, they had no idea who you were, didn't care.

Now you're starting to see, you know, the Brooks Brothers of the world and the Vineyard Vines and some other brands start to make untucked dress shirts.

It's funny. A lot of times people ask me, what's been the greatest moment that kind of sticks out for you?

And it was the day, which you think it would have been a depressing day, but the day that it clicked, that every single competitor, editor.

Vineyard Vines, J .Crew, Banana Republic, just go on.

Everyone led their 2019 spring campaign with shirts meant to be worn untucked.

Now, two of the big ones led with shirts designed to be worn untucked, and we had to make them remove that.

But everyone, I mean, Vineyard Vines set up a section in their store.

They're known to be tucked in shirts, more than any brand you've ever had, right?

Like shirts that are preppy and tucked in.

They had an untucked section in their store.

It was, it was kind of a feeling of accomplishment that I started this kind of little idea at a Hoboken.

And now the whole fashion world, the whole billion dollar brands have been around forever are now changing their strategy because of us.

And I think it's your even more attention to the untucked shirt and what more do you want when your name's on tuck it?

Right. So it ended up propelling us in 19, you know, to having, you know, our best year we had had ever had by a long shot.

At this point, you guys are going beyond shirts.

I mean, you're doing you're starting to get into other parts of the apparel world.

Right. And today, of course, you do sport coats and trousers and, you know, all kinds of things.

And you've got, you know, clothing for women.

But, you know, by any account, you're a really successful, growing player here and you know you're on par at this time or maybe even more so that with the bonobos and the you know the stitch fixes and you know these big brands that are really kind of emerging in apparel and there is talk about an acquisition right this is about what 2019 you start to talk about maybe late 2019 2019 okay and tell me the story about the acquisition car who is the the Acquirer?

What's the story? How does it start?

So we just decided in late 2019, we were growing so fast and we had so much growth ahead of us.

We went into England.

We had been doing very well in Canada.

We had expansion plans across Europe and we had a growing women's brand with zero marketing.

We had a growing pants brand with zero marketing, all these amazing things.

And we just decided to go test the waters.

And we had 15 letter of intents coming in at a very, very big You decided to test the waters just because you, this was a good opportunity time.

You felt like, okay.

And I should mention the first couple of years you were profitable, but you were small.

Now that you're growing and you're investing in growth, you are no longer profitable, which is normal.

But now you felt like, okay, this is maybe an opportunity to get acquired by a bigger brand, you know, one of these big conglomerates or something because now then they can take it to the next level.

Yeah. And there's two things that I've always wanted with this.

I wanted one to make good money.

And two, I wanted this to be a brand that way outlives me.

That's very important.

I wanted, you know, this to be a brand that's here for the next 50, 60 years, right?

Or whatever. By the way, I want to thank you for saying, I wanted to make money because too many entrepreneurs come on the show and they don't say that.

And I think that's disingenuous.

I don't think there's anything wrong with saying I did this to make money.

I wanted to make money.

So many people say, you know, money wasn't really an issue.

It was about the mission or it was about the community.

And I'm just like, come on.

For me, it's not, the money is not only because of the money.

The money is because to me, that's the, if this were to end right now and someone sees me next week and say, congratulations, Chris, you did an amazing thing on Tuckett.

I would be like, I didn't really.

I never really, like, so that much sale with the money is like, I did it.

I built a brand and I sold it for a lot of money.

Like, that's what I say about the money.

But also, I do want the brand.

And the reason I say that is I really believe that this is going to be a billion -dollar brand.

I still do. So you guys went and worked for the bank and sort of hung your shingle out there, and you had 17 letters of intent.

Fifteen. Potentially.

About 15. About 15.

And we knew the number that we were requiring, which was a very big number.

Over a billion dollars?

No, close to it. It's probably north of 750, somewhere around there.

You know, you probably have an outlier, you probably have a real low one, right?

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

So basically in my mind, I'm there.

I mean, I'm sitting there, you know, weeks away.

You know, I'm dreaming of the coast of France.

And I was like, it was real.

You know, I was, and you know, if it was done a little earlier, we shut it down because of COVID, obviously.

Who shut it down? down.

Everyone reached out to us.

We're not going to do a deal.

You can't do a deal.

All of the potential acquirers pull out.

Yeah. Or I don't know if it was pulled out.

It was more of a, we're not giving you our letter of intent right now.

The world is closed.

We're going to take some time.

Okay. Yeah. I think it's shut.

When did it shut down?

March. It was in March. It was in March of 2020.

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

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

I mean, so close. And I owned, by the way, a lot of the company because when Kleiner put on 8 million, they were very adamant, our main investor, to say, this company's doing well, do not dilute, let's just raise with debt.

So we took on debt because we had a plan, But we had very little cash, you know, in comparison to what you need going through COVID.

So that, so the bad news was that was shut down.

The worst news was that, you know, now all of a sudden you're scrambling, you know, what's our accounts payable?

What's our debt? What's this?

We are, our numbers, sales numbers are starting to drop significantly.

But the biggest thing is I realized, OK, we have some significant cash issues here and they're happening fast. Right.

Like because, OK, now they're closing our stores.

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

What did you see like percentage decline from March to April of 2020?

You remember like more than 20 percent, 30 percent?

Probably like 40, 50%.

Just drops. Yeah, because it was as, so we would get, my investor would call us and say, I don't understand.

Everyone else is doing good online.

And we're like, you don't understand because everyone's buying Viore, right?

Everyone's buying non.

And by the way, I'm still doing decent amount of revenue with non -shirts.

The problem is when you have 40, 50, 60 million less in revenue, the math is very simple.

You run out of money.

so we got on the phone with a bankruptcy attorney and he's like you have to declare bankruptcy or this is why bankruptcy exists your lawyer saying this was when in March this was April April wait how much debt did you have by the way like tens of millions hundreds of millions yeah we know we had like 30 40 million but that wasn't because you had you couldn't get new debt so my that that's the bigger you couldn't go get money because you had 30 million in debt you couldn't get money and And your lawyer, even though you had this national brand and, what, 90 stores, your lawyer was saying to you,

you got to declare bankruptcy.

It didn't matter because our, so we had to pay our monthly payment to the stores, the 90 stores.

The lease, right, the rent, right?

We had to pay that number.

We had to pay all of our employees.

Some of these stores are probably 20, 30 grand a month in rent, maybe more.

No, it's a lot of money.

And then we had to pay all of our employees.

We had just grown too fast, too many employees, paying 90 stores, a big office, all these things that we needed our money to be coming in.

And by the way, our factory accounts payable was huge because we were bringing in product for that year that was going to allow us to do massive volume.

We had already ordered it.

And we had to tell them we can't take the product.

And they're like, well, you owe us $30 million or whatever the number is.

So the guy, I said, what is bankruptcy?

bankruptcy you know what do you what is it i mean of course everyone knows high level what is bankruptcy i mean i didn't know that you know oh bankruptcy what is it we you know what i probably keep most of my equity we kind of and then we'll just read they're like well you own nothing zero and you're not going to get paid a dime because they're going to kick you right out and you know there's going to be with us there'd be a bidding war so it's even more painful yeah but why was your lawyer i guess your lawyer was it wasn't my lawyer it was a lawyer they brought on who was a a bankruptcy attorney.

I see. Okay. And he was saying, look, the only way to save the brand is to, and that meant that you wouldn't, you know, all this debt would go away.

But then, and you could walk out of there having banked some money and - No, very little.

It would have been very, very, very little.

Like they would have, you know - They'd gone after you too, probably.

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

I cannot imagine, even when that was brought up, because you're not a lawyer, you know, most of us aren't lawyers.

When a lawyer says that, I think a lot of people take it seriously.

Like, okay, well, I got to consider this.

It was the hardest thing to run.

But the problem is you're also dealing with this COVID stuff, which right in that period of time was scary for everyone, right?

Like you're sitting, you know, you can't leave your house.

You can't, and by the way, that's not a small thing.

I don't mean to, everyone goes through, everyone went through something with COVID.

So many businesses were lost. So I'm not the only one.

It just so happens I was days away from selling it for such a big number.

That's the only, you know, that it was that kind of super high to super low.

So I got on the phone with my partner.

We didn't really know what to say or do.

I mean, you don't, you didn't know when COVID was going to end.

That's the problem.

That was what made this so bad.

So we called our, uh, all of our landlords one by one.

We called all of our factories.

Some were great. Some we had threatened back and forth with lawsuits, this and that.

90 % of them said, we think you're going to be an unbelievable brand post -COVID.

We're going to hang with you no matter what.

So we built up this massive accounts payable.

I don't want to say the number, just to survive.

We raised some money at a very low valuation because you had to.

Did Kleiner put more money in during this crisis?

They did. They did.

Okay. So they, and they probably got a good deal.

They did get a good deal.

I just cannot imagine the level of stress that you were under because, first of all, you're dealing with just declining revenues.

You've got to figure out a quick way to get cash infusion.

And I believe that you guys had, like, three kids in quick succession around this time, like, over a three -year period of time.

I had four in, yeah, six years.

Yeah, all that was happening.

It was, um, it was, we were there.

We made it to a point that it was now, you know, hanging by a thread.

There's really only one person I could talk to about.

It was my partner. Cause I didn't want to bring in my, my, my wife and my dad.

I didn't want to get them nervous.

You don't want to talk to them.

You don't want to talk to your wife or your dad about this.

I didn't, it was, it was so bad by the way, if, if the company went bankrupt, I couldn't, I don't want them to give too much of my personal life, but I couldn't have afforded my, you know, I just sold some of the company.

I had built a house.

And now it was an ego hit.

I hate to say it. It just was.

Your company gets pulled from you.

There's nothing wrong.

Of course. It was a money hit, because now you have no money.

And by the way, you're not making money.

You're not getting a job over COVID.

It's just hard. And you have four kids.

It was crazy. And it was not because of anything we did wrong.

That's what bothered me about it.

And there was no solution.

You want to know why I didn't tell my wife and father?

because there was no solution.

Yeah. But you kind of start to emerge from COVID.

And we've had stories like this in the show with other apparel brands where COVID ends and they're brands that weren't really fit for COVID.

Like they're really more, you know, things that you would wear outside to just look good.

And then after COVID, they just explode in growth.

And I imagine that once people start to emerge from COVID, not necessarily going back to work, but even going out, people started to buy the clothes again.

They started buying the clothes again.

Now, we had no cash, right, because we're coming out.

So we really didn't know what to expect.

What happened was we were able to take on some debt to get us through it.

That's how we solved our bankruptcy problem.

We solved some with cash and some with debt.

We cut back inventory.

We do good in 2023, our most profitable year ever in 23.

Not the growth year where we wanted it to be.

Now, long story short, I want to make sure I'm very clear about this so we solved the problem in 24 and we are now having a tremendous 25 and we are beginning our wholesale growth.

And I can get into that in a second as the final phase.

But it just took four years.

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

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

No, we're profitable.

You are profitable.

Okay. We were profitable in 22, and we were significantly profitable in 23, even though the year wasn't what we wanted because we didn't market.

And 24, we were profitable, and this year is an exciting year.

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

Tell me a little bit about that decision.

decision well like i said i want to be i want to be a massive brand uh you know a brand that fits all demos men's fathers sons kids you have to go into wholesale eventually if you want to scale to that level to a billion dollar brand you know we're opening in mexico city later in the year like just so many exciting things so that's the one area that low -hanging fruit because customers want us we know that so they're going to want us where they shop and that's a huge Huge opportunity.

And it's definitely part of the long -term plan so I can get back to north of where we were, you know, in COVID, pre -COVID.

You know, I'm wondering now, I mean, here you've been through certainly trial by fire, a lot of highs and a lot of lows in building this brand since 2010.

2010. Here you are now, almost 15 years into this thing.

You're obviously super experienced.

How do you see your own role playing out?

I mean, I guess, I imagine that at some point, you'd like to hope, hopefully, try to see if you could get acquired again, maybe, right?

Or, I don't know, maybe go public, which is risky, too.

But I imagine there's an there's a point at which you do exit this thing.

Yeah. No, I will definitely want to get acquired and sell and kind of make this an ultimate.

Now it's become, I need this now to get over this.

You don't want to be the person who's going to sell for something and then sell for nothing or sell.

So now it's like I'm back in that.

Listen, I'm more stressed now than I was ever.

There was this little period of time in 19 and 20 when I wasn't, because I need this to to happen.

I am, you know, I am it's these three years have been very draining and, you know, and as Aaron would say the same thing, like we have to see this through, but I'll tell you that any deal that I do, I'll still be here, you know, helping grow.

I do believe I, when I say, I think this can be an international brand, I really believe it can, I want to be there for it.

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

Chris, given where you are now, I mean, you even admit that when you started this idea, it was a one in a million chance of working, of succeeding, because apparel is hard. It's really hard to build an apparel brand.

But it did. It did succeed.

And I wonder how much of where you got to now, where you are now, and when you reflect on it, how much do you attribute to the work you put in, the grind, and how much do you think had to do with luck?

So I'm a big believer.

I'm not someone who denies luck.

Luck is so important in every area of life.

There's not one successful person who didn't get luck.

I think there's a massive amount of luck.

I say luck because I launched it at a period of time where I think it allowed me to make mistakes and to still take advantage of paid social.

You can make an argument that isn't luck, that strategy, whatever.

But I think it's a blend.

I think there's no question the hard work, my vision and pushing through and just doing it.

I would say just doing it.

How many people just don't do things, right?

It's crazy. It's draining to be an entrepreneur, I guess is all I can say.

But I think it's a mix of luck and a mix of hard work.

You need both. That's Chris Riccobono, co -founder of Untuckit.

And by the way, remember Chris's wine vlog, Pardon That Vine?

He stopped doing it years ago, but the videos are still up on his YouTube channel.

And in the last one he posted way back in 2012, Chris is reviewing a Syrah from New Zealand and what he's wearing?

An early version of an Untuck It button -down shirt.

Hey, thanks so much for listening to the show this week.

Please make sure to click the follow button on your podcast app so you never miss a new episode of the show.

And sign up for my newsletter at GuyRoz .com or on Substack.

This episode was produced by J .C.

Howard with music composed by Ramtina Rablui.

It was edited by Neva Grant with research help from Kerry Thompson.

Our audio engineers were Patrick Murray and Robert Rodriguez.

Our production staff also includes Catherine Seifer, Carla Estevez, Casey Herman, Sam Paulson, Alex Chung, Andrea Bruce, and Elaine Coates.

I'm Guy Raz, and you've been listening to How I Built This.

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[The Untucked Revolution: How Chris Riccobono Built a Brand Out of a Simple Problem]-[UNTUCKit: Chris Riccobono]

📋 Summary

The Untucked Revolution: Turning a Simple Problem into a Global Brand

The Entrepreneurial Itch and the Search for an Idea

Solving the "Out-of-Spec" Problem

Surviving the Early Hurdles

Scaling and the Power of Marketing

The COVID-19 Near-Collapse

Looking Ahead

🎯Key Sentences

📝Key Phrases

📖 Transcript