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