Advice Line with Chris Riccobono of UNTUCKit

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slash h-i-b-t. Hello and welcome to the advice line on how I built this lab. I'm Guy Raz. This is the place where we help try to solve your business challenges.

Each week, I'm joined by a legendary founder, a former guest on the show, who will help me try to help you. And if you're building something and you need advice, give us a call, and you just might be the next guest on the show.

Our number is 1-800-433-1298. Leave us a one-minute message that tells us about your business and the issues or questions that you'd like help with. All right, let's get to it. Joining me this week is Untuckit co-founder Chris Riccobono.

Chris, welcome back to the show. Great to be here again. So, Chris, when we last talked, not that long ago, in 2025, you told us the story of Untuckit. And if anybody missed it and wants to go back and listen, I highly recommend you do.

We'll drop a link to it in the show notes. Chris, you started out as a medical device sales rep. You had no fashion background. And you were thinking about different businesses until this idea came to the shirt idea, a shorter shirt, a button down shirt that you could wear untucked.

And you almost talked yourself out of it because you thought, well, if there was a market for somebody else would be doing it. But within about 10 years of that idea, with the help of a friend of yours from Columbia Business School, Aaron San Andreas, you guys built Untuck It. going from zero to like 73 stores in just four years. You've been through a lot.

That episode was so powerful because it had so many ups and downs and a lot at stake. First of all, how have things been since we last spoke?

They've been okay. You know, it never ends. When I was on that episode, we talked about COVID. We talked about high interest rates taken on debt

to survive COVID. And I believe we were just touching on tariffs, but we had not gotten there yet. I think we were predicting that there could be some tariff issues. Well, they, of course,

hit us hard. We had about $9 million that was pulled out of our bank account that we had no line of sight to. And that was for two reasons. One, the normal tariffs, but then also Trump removed in the middle of the night this 3-2-1 de minimis rule, which you could ship from Mexico. It had been in effect for like 100 years without paying duties. So that kind of doubly hit us.

so we are fighting through it we still have a loyal following we just started getting into wholesale that's new so that'll be our now we'll have e-com stores and wholesale but we're working through the cash issues so you'll be in department stores we'll be in department stores for the first time ever that's great congrats on that yeah should allow the brand

to really scale even further so i want to ask you about another you know we talked about this briefly when you were on the show, but you had launched a second brand, a sportswear brand called Greatness Wins. Tell me a little bit about how that's going. I mean, this was a completely separate parallel brand, hard to run two things at the same time, and you're a very determined guy,

but tell me a little bit about how that's going. That's going great as well. We pivoted there a little bit, and for those who are out there in anything that they're marketing on Facebook and paid social, everyone knows that the customer acquisition costs are very high just based on the amount of competition out there. So our pivot was to go into wholesale earlier, but in this case,

Greengrass Golf Shops, which is, for those of you know, the golf brands, the Peter Millar's, the Johnny O's, you can do 150 million North in just those shops. The way I looked at it, it was a way to increase revenue, but also free marketing. Because if our shirts at your local golf course. You go in there, you buy the golf shirt, you then go home, you go on your website,

you buy our shorts. So now we have a golf and athletic brand. It's a battle. It's, you know, retail is tough. You have the Viore's, you have the Lululemon's, you have the, the aloes. These are monstrous companies, Nike. Um, but we are finding a way, you know, by trying to go different directions and, um, you know, lower the cost of acquiring a customer and it's exciting.

I love that word battle because I think you used it when you talked to us. You're not sugarcoating this. It is tough to run an apparel brand. It is true. It is a constant battle. I was wondering, Chris, as you just explained, the customer acquisition landscape is so different from when you launched Untuckit. If you were starting from scratch in 2026 with no brand recognition, what would you do differently? How would you build Untucket today? Do you even have a sense of how you would do that?

What's interesting about Untucket was everyone's doing paid social today. Even when everyone was telling us, all the experts in marketing were saying, stop marketing on anything but paid social. It's all dead. We said, well, we can afford it and we don't agree.

And we went on, we talked about this last time, we went on airline magazines. We went on radio for a fashion brand, which is rare because you can't see it. We went on Howard Stern. We went on the USA Today's back of New York Posts.

And that's what made us successful. And we mixed that in with TV, more expensive, paid social, and it all came together. And by the way, we're still doing that today and very few are doing it. So that's how I would do it.

Now, it would be a lot more challenging because my cost of acquisition on Facebook when it was us, Casper, and Bonobos, I think, and maybe Warby Parker back in 2011. It was a lot easier.