Chris Ricobono walked into garment makers all over the fashion district in New York and no one would make an off spec shirt for him.

Dave Young:

Welcome to the Empire Builders Podcast, teaching business owners the not-so-secret techniques that took famous businesses from mom and pop to major brands. Stephen Semple is a marketing consultant, story collector, and storyteller. I’m Stephen’s sidekick in business partner Dave Young. Before we get into today’s episode, a word from our sponsor, which is, well, it’s us, but we’re highlighting ads we’ve written and produced for our clients. So here’s one of those.

[Pinpoint Payments Ad]

Dave Young:

Welcome back to the Empire Builders Podcast, Dave Young here alongside Stephen Semple. And we’re talking about empires being built and fortunes being made and brands being established and something different happening. And you mentioned the theme for today’s show. The topic is a shirt brand called Untuck it.

Stephen Semple:

Untuck it,

Dave Young:

And I am a little familiar with them. Number one,

Stephen Semple:

Oh my God, a fashion brand that Dave’s a little bit familiar with.

Dave Young:

Oh, I own two of them. I have two shirts. And I feel like I’m responsible for the brand.

Stephen Semple:

Okay.

Dave Young:

I’m just that kind of guy that my torso is the weird length and I cannot for the life of me keep a shirt tucked in. So years ago, I quit trying, unless I’m going to be in a tuxedo with a cummerbund that tightens that up. I’m like, you’re not going to find me in a tucked in shirt because it’ll untuck itself. So I’ve always embraced the idea of buy shirts that look good, whether they’re tucked in or not, and Untuck It actually created dress shirts.

Stephen Semple:

Yes, sir.

Dave Young:

That you don’t tuck in. You’ve got quite enough tail to be tucked in. So I’m interested in how they got their start. And I bought my two shirts from an actual Untuck store in a mall in Portland, Oregon.

Stephen Semple:

There you go. Yeah.

Dave Young:

So I think I know where you’re headed with this, the experience.

Stephen Semple:

Yeah. Today they have, I think they’re approaching 90 stores now today, and they also now have got a women’s line and of course a major strong online presence. But it was founded by Chris Ricobono and Aaron Sendez in Hoboken, New Jersey in 2010. And they are, as you said, a shirt designed to be worn untucked. And in fact, their early ads featured Chris basically walking down the road talking about how this is what he wanted to create.

And they’re kind of funny actually. If you go look at them, they’re a great origin story. And he’s walking down the street in New Jersey and he has this unbelievably serious tone to him about how he wanted to fix this whole shirt problem. And that actually in the early days, David Letterman and Colbert and whatnot were making fun of these ads, which he loved. Like, “Hey, I’m getting some free press here.” But yeah, go and check them out on YouTube. Kind of great. I can really understand why those ads work.

So Chris grew up in New Jersey and he took finance and college, and he was actually always really nervous about corporate America. He was worried about his career. And so his whole idea was he was going to get a job, but while he got the job, he was going to look for what the next thing was going to be. So he was always looking for the next idea. And he was nervous in corporate America because he wasn’t good in crowds, and he wasn’t good with spreadsheets and he wasn’t good with socializing. So he always sort of felt like he was an outsider there

And eventually got a job being a salesperson and medical devices for GE. And he was there for about 10 years, but he knew he was never going to be long-term. And while he was at GE, he did an MBA at Columbia and it stimulated a lot of ideas for him, and he knew he needed to get an idea. And the early one that he did actually was a wine blog. He did this wine blog called Pardon That Vine.

Dave Young:

Oh wow.

Stephen Semple:

It was the only idea he had at the time, and he did it. It was his passion. He loved collecting and drinking wine. And in fact, how that all started was he was invited to a dinner from a cousin of his and his cousin was a wine guy, and his cousin would say, “Go down and grab a bottle of wine, grab any bottle of wine.” And he’d bring up the wine. And this is going to speak to you, Dave. He would bring up the wine and they would tell a story about the wine, about the region, about the grapes, about the winemaker. And all of a sudden Chris fell in love with wines through the stories, which is what you guys teach at the whiskey marketing school, right?

Dave Young:

Absolutely. Yeah.

Stephen Semple:

And he became obsessed with it. And so he decided to do this blog and he thought it would lead to some consulting and presenting, and social media wasn’t around yet. There was only Facebook, and it was kind of limited. And wine was very snobby then, and he wanted to make it accessible and mainstream. Now, turned out this helped him at his career at GE because his customers would want to go out for dinner with him. He wouldn’t sell them anything. He would take him out to dinner. They’d have this great dinner. He would tell the story of this wine, and then they would end up buying product from him, power of that story. But he hated the shirts, so they would always feel uncomfortable and whatnot. And what ended up happening one day as he bought a shirt that was off spec, a J. Crew shirt that was off spec. So in other words, it was a medium shirt, but it wasn’t the right length. And he loved it. He wore it all the time.

To the degree that when he would go into stores, he would try to find off spec shirts. He would specifically look for ones that were improperly made. In other words, they were too short. And he started sharing this idea with his friends of, “I think I’m going to do this as a company.” And his buddy, Aaron, who was a partner at one of the big accounting firms, forget which one.

Dave Young:

Fives.

Stephen Semple:

Yeah. He shared that idea with Aaron. And Aaron was like, “Let’s do it. Let’s do it. We’re going to do this idea.” Now, here’s the fun part. Neither one of them had any background in fashion. Have we heard this theme before?

Dave Young:

Sure.

Stephen Semple:

New idea coming from someone with no background in the industry, but lived in New York. He was outside of New York in New Jersey, and as we know there’s a huge garment district in New York. So he grabbed this J. Crew shirt and he would walk into places going, can you make this.

Dave Young:

Okay?

Stephen Semple:

He would go through the pitch with the garment makers and they all go, “You can’t make a shirt like that. It’s off spec. You can’t make a shirt like that. It’s off spec. You can’t make a shirt like that. It’s off spec.”

Dave Young:

Yeah. This is the new spec.

Stephen Semple:

He went door to door. It took him two years to find somebody who’d be willing to make the shirt.

Dave Young:

Wow. Two years.

Stephen Semple:

Two years. So he went door to door two years, and I finally found somebody who’d make the shirt. So he had to raise some money, they had to build a website, and they had to come up with a name. He came up with the name Untuck It. Now, the interesting thing is anybody he shared the name with, they all hated it, but he decided not to listen to it. And I think Untuck it is an awesome name. It’s a verb.

Dave Young:

Sure. Yeah.

Stephen Semple:

It’s a verb. And right away it describes what his product is. The Untuck it dress shirt. Do I need to say anything more?

Dave Young:

No.

Stephen Semple:

Shirt designed to be worn. Untucked.

Dave Young:

Right? You don’t tuck it in and you don’t wear a tie.

Stephen Semple:

Right?

Dave Young:

Damn It. I’m in. Take My Money.

Stephen Semple:

They pull together 150k. They found this guy from Poland who had an office in New York City. They’re going to make the shirt in Poland. Now, it’s interesting, Chris believes that today it would be far easier of all of these fashion brands that are springing up to do this today. And he actually feels, because of the challenges, it actually created an advantage for him. So the first shirts were terrible. They didn’t know that they had to be pre-washed, so you have to pre-wash stuff before you make it. The shirts were wrong and they started getting back this terrible feedback, but they had to still sell the shirts.

And here’s one of the decisions they made. We’re still going to sell the shirts. We’re going to keep these people’s names. And when we eventually get it right, we’re going to give them a free shirt, but we need the money. Next one, buttons were wrong. You could just pull the buttons off because the machine, something was wrong with the button machine. And so they sent everybody an apology letter and a five-dollar coupon, take it to your laundromat, have them fix the buttons. So initial quality was, they struggled a long time with it, but they remained positive. When people first got the shirts, they would get this big long letters from folks about how much they loved it.

And the problem was they didn’t understand this idea that there’s this tech pack that you have to send when you do a shirt. It has to be laundered this way. It has to be done this way. It has to be done. They were figuring all that out because the problem is cotton both grows and shrinks.

And length really would vary because even when you pre-washed it, you’re pre-washing 15,000 shirts together, one would shrink a little bit more. It turned out to be a very imperfect process, and it took them a long time to figure out how to make the length exactly the same. And it took them like three years. For three years, they were actually selling shirts that were not that great a quality. And Chris talks about today they would be killed because today the social media postings and whatnot would kill them. But they eventually got it right. And they’re also happy that in the early days they grew slowly because again, they weren’t putting out a great product. Now, they eventually fixed all of that. They eventually reached out back to all of those people and gave them a new shirt. But-

Dave Young:

Stay tuned. We’re going to wrap up this story and tell you how to apply this lesson to your business right after this.

[Empire Builders Ad]

Dave Young:

Let’s pick up our story where we left off. And trust me, you haven’t missed a thing.

Stephen Semple:

Now, they eventually fixed all of that. They eventually reached out back to all those people and gave them a new shirt. Right? But took a long time. So not knowing fashion was a disadvantage because of all these production problems, but it was also an advantage. They kept soldiering through it. They’re like, “No, we’re going to get this right.” So then they’re growing along nicely and they finally realize they finally get shirt working rights 2014, and they decide we want to kick growth. We now got a good product. And they got $21,000 to put it into marketing.

Dave Young:

$21,000?

Stephen Semple:

Yeah, $21,000. And they did exactly what we would tell people not to do. They bought a three-week flight on a sports radio show in New York.

Dave Young:

Oh man.

Stephen Semple:

But you know what? It worked.

Dave Young:

Okay.

Stephen Semple:

It exploded. Now, I think part of the reason why it worked is first of all, it was so unique and there was a built-in demand for it, and they kept their message super simple. It’s a dress shirt designed to be worn untucked. UntuckIt.com.

Dave Young:

I mean, I can see it working. It’s also not a big decision to make, right?

Stephen Semple:

Correct.

Dave Young:

It’s not a long product purchase cycle thing. It’s like, oh, it’s a new shirt.

Stephen Semple:

And I think it was unique enough that somebody will go, “Yeah, I’ll try it. I’ll buy one.”

Dave Young:

Most of the new shirts I’ve purchased in the last couple of years have either been a weird Facebook ad or just like, oh, that’s a different colored fishing shirt.

Stephen Semple:

Yeah. Yeah.

Dave Young:

Than I currently have.

Stephen Semple:

So the next thing that they did is they did airline magazines was the next place that they went.

Dave Young:

Back when those were big.

Stephen Semple:

Right. And what they found was the only people advertising in airline magazine was high-end watches and fragrances. And so they discovered a halo effect ,that these guys must be doing well. And this shirt must be awesome because who you’re beside. Now, if you don’t think there’s a halo effect, there absolutely is. And I can prove it. If you are doing billboards, if you’re working with a jeweler, a co-oping advertising with Rolex, and you want to go on an electronic rotating billboard, Rolex will only allow you to go on that billboard if these advertisers are on it. In other words, Rolex knows that if my billboard comes up and then it’s a dog food ad next, it actually impacts my brand. They’re really picky about who else is on that. And Rolex will only approve it if they can look at who all the other advertisers are.

Dave Young:

The power of association.

Stephen Semple:

Power of association. It is real. Now, when they first started marketing this, they thought their buyers would be young fashion forward people. Turns out evenly distributed across the board. They do. So here’s the things get interesting. So remember I said they started doing airline magazines? They even did billboards while a competition. Fashion companies are doing all the social media, these guys did billboards, and they even did a billboard where they didn’t show the shirt. Untuck it, a dress shirt designed to be worn untucked. People didn’t need to see it. They love the idea.

Dave Young:

Yes.

Stephen Semple:

It’s the idea that they liked. So five years in still working at GE, he’s scared to leave his job. Chris is scared to leave his job. But remember, they’re advertising in airline magazines. It’s 2015 and he’s on a flight to a sales meeting. Okay. Guess what? There’s a big picture of him in the magazine with the ad, because his picture and his story is in the ad. His boss kind of goes to him and says, “I think it’s time for you to move on.”

Dave Young:

Oh, that’s funny.

Stephen Semple:

He ends up leaving GE and doing this full time. In his 2017, they started opening stores because one of the pieces of feedback that they got from people is, I need to touch it and feel it. That’s the resistance point, because they’re also pricing at a bit of a premium price. So they have 25 stores at this point. So they’ve grown no outside investment, 25 stores. So they do their first fundraise, they raise $30 million, and other brands start to notice, and they start making an untucked shirt. Now it’s 2019. 2019. They really get this feeling of accomplishment because in 2019, all their competitors, all their big competitors have an untucked version of their dress shirts. And in fact, almost lead with that in their advertising.

Also, in 2019, they decide, you know what? We’re going to cash out. We’ve grown it to the size. We’ve grown it. It’s time to cash out. Now, remember I said to you when the countdown was happening, there’s a crazy twist in this story. Here’s where the twist happens. So 2019, they’re growing so fast, they’re entering England, they’re launching other things. They decide to shop the business. They get 15 letters of intent with really big numbers,

Really big numbers. They’re pretty confident they can sell this thing for 750 million bucks based upon these letters of intent. It was there and they were weeks away from closing.

Dave Young:

And then I’m guessing pandemic.

Stephen Semple:

Pandemic happens.

Dave Young:

Yeah. Nobody wears a dress shirt at all.

Stephen Semple:

Everyone pulls out. Well, remember everything was put on pause.

Dave Young:

Yeah. Well, you put on pause and now you’re only going to be seeing people from the shoulders up anyway.

Stephen Semple:

They were about to sell for 750 million, and they had had a business that was, remember, they took no very little outside investment. They were very lean. So guess what this also meant? They did not have much in the way of cash. They had also bought a whole pile of inventory expecting this to be a great year. They now have brick and mortar stores that are closed. Rent till needs to be paid. Suppliers still needs to be paid. They have a 50% sales decline because while clothing was being sold online, it was casual clothing. And they get the advice from their lawyer, “Dudes, we’re going to have to declare bankruptcy.”

Dave Young:

Wow.

Stephen Semple:

So in a 90 day period of time, they go from, we’re selling this business for 750 million to we need to declare bankruptcy. Could you imagine that? Going through that?

Dave Young:

That’s sad.

Stephen Semple:

What a swing. Now they figure out they don’t need to declare bankruptcy. What they decide to, they call every landlord that they have who decides to hang in with them. They call all their suppliers, most hang in with them. They were able to raise a little bit of money to take themselves through it because the people who invested in them before saw this as an opportunity to invest more at a really great rate.

And they got through it. They managed to get through it. And in 2023, they started to emerge. Because again, people are now returning back to work, all this other stuff. In 2024, they recover completely financially, and in 2025, they’re back on the wagon and they’re back on track. But when I was listening to the interview with Chris and he talked about going from that, I thought to myself, “How do you get through that?” I’m like, “Dude, I admire that you worked your way through it.” Because the go through, we all have stories from the pandemic in terms of, oh, it really affected me. These guys take the cake. Like, wow, holy crap. Like crazy town. Right?

Dave Young:

Yeah. Go ahead.

Stephen Semple:

I was just going to say, and this is part of what I wanted to share, is sometimes these things happen out of your control and you just got to figure out a way to get through it. But what I love was, this is an example of he’s from outside the fashion industry. And the fashion industry could not see that people actually wanted a dress shirt that you would wear untucked, and yeah, took him a long time to figure out how to do it. But it was right there. And yet, even when he pointed out to people in the fashion industry, it took him two years to find someone who was willing to make it. How nuts is that? You would think that you would show somebody and they would go, “Oh, that’s a really good idea. People would want to wear it untucked.” It’s like, “No, that’s not the specs. You don’t make shirts that way.”

Dave Young:

Yep. I love it. I love it. As you’re talking, I’m looking at their website. On the very front of the website, there’s a dude with shirt tucked in. I don’t understand that. So of their, it’s a golf shirt. They sell way more than just dress shirts,

Stephen Semple:

Oh, they do now.

Dave Young:

You don’t tuck in now. Yeah. There’s jackets, there’s pants.

Stephen Semple:

They do do jackets and pants. And they have a women’s line.

Dave Young:

Shoes.

Stephen Semple:

Oh yeah. Yeah, they do. They’ve expanded and expanded. It’s a whole bunch of other things, but I just love how this all started with him because he would hunt for off-spec shirts purposefully.

Dave Young:

Yeah. Yeah. I love it. I love this story. Well, thank you for sharing the Untuck It brand.

Stephen Semple:

All right, awesome. Thanks David.

Dave Young:

Thanks for listening to the podcast. Please share us, subscribe on your favorite podcast app and leave us a big fat juicy five star rating and review at Apple Podcasts. And if you’d like to schedule your own 90-minute empire building session, you can do it at Empirebuildingprogram.com.