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The Casey Adams Show

Chris Riccobono – Founder of UNTUCKit on How He Built One of the Most Recognized Brands in Modern Retail

The Casey Adams Show

Listener.com Podcast Network

Business, Entrepreneurship

4.8637 Ratings

🗓️ 2 May 2025

⏱️ 47 minutes

🧾️ Download transcript

Summary

Today on The Casey Adams Show, I sit down with Chris Riccobono — Founder of UNTUCKit, the menswear brand that redefined how millions of men wear shirts. What started as a frustration with fit became a nationwide movement, turning a side hustle into a retail empire with over 80 stores and millions of loyal customers. In this episode, Chris shares how he transformed a single problem into a scalable solution, why differentiation and storytelling built brand loyalty, and what it really takes to thrive in today’s fast-moving retail world. We also dive into balancing fatherhood and entrepreneurship, navigating e-commerce shifts, and the mindset behind long-term success.

Connect with Chris Riccobono: https://www.linkedin.com/in/chris-riccobono-25b8821b/

Learn more about UNTUCKit: https://www.untuckit.com/

Chapters:
00:00 The Birth of UNTUCKit
02:59 Navigating E-Commerce and Retail Evolution
05:57 Launching Greatness Wins: A New Venture
09:02 Balancing Fatherhood and Entrepreneurship
12:02 The Journey of an Entrepreneur
14:56 The Passion Behind the Wine Video Blog
23:50 The Journey of Growth and Consistency
25:11 Navigating Challenges During COVID-19
29:36 Building Customer Loyalty in a Competitive Market
33:56 The Importance of Differentiation and Marketing Strategies
37:40 The Evolving Landscape of Influencer Marketing
42:00 Advice for Young Entrepreneurs and Founders

Transcript

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0:00.0

All right, welcome back to the Casey Adams show. Today we are joined by a very special guest,

0:06.8

Chris Rickabono, the founder of Untucket. Chris, thank you so much for coming to the show today.

0:12.2

Thanks for having me. Of course, man. So first of all, I really do appreciate you taking the time today.

0:18.7

And I'm so just fascinated by your story

0:23.2

and what initially led you to launching a tucket. You know, you've, you've been at this now

0:27.4

for nearly 15 years, I believe. And not only just in tucket, but even, you know, the modern

0:32.6

brands you've launched, such as greatness wins. And again, to take us back here, one of the things that I loved

0:39.7

when doing my research and diving in Untucket is just the simple thought of, you know, like,

0:44.4

why aren't shirts, you know, worn to be not tucked in? Like, where did this initial problem

0:49.4

and idea stem from? And I always love understanding. And I know my audience does as well. When was that moment

0:55.8

when you're like, wow, I think I should actually pursue this or let me dive in more and learn more to see

0:59.3

if I can actually turn this into something. Yeah, you know, if you're young, you probably think it's a

1:03.9

crazy idea. But when I, I'm 46, when I was in, in college people wore their shirt. Like when I, back then, 20, 25 years ago, everyone wore oversized clothing.

1:14.1

You know, when I was in college.

1:15.1

This is before you're born probably or when you're five, six years old.

1:18.8

Yeah, I was a lot of Abercrombie.

1:20.7

Yeah, I was, that's when I graduated in 01.

1:23.6

And it was a lot of Abercrcombeian fit stuff, oversized stuff. We graduated college, got into the real

1:28.9

world, you know, clothing started to get a little more fitted, not like it is today. You know,

1:34.7

we were always behind Europe, but it started to get a little more fitted. And every shirt, you know,

1:38.5

was down to mid thigh. And I always thought about it and people just kept wearing them. And in my mind, you know,

1:45.7

this was before it was, I don't want to say easy, that's the wrong word, before you were able to

...

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