How I Built This with Guy Raz UNTUCKit: Chris Riccobono
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Jun 23, 2025 
In this engaging discussion, Chris Riccobono, the founder of UNTUCKit, shares his entrepreneurial journey from a GE salesman frustrated with dress shirts to launching a successful clothing brand. He details the challenges of creating the perfect untucked shirt and overcoming manufacturing hurdles. Chris highlights pivotal moments like a risky shift to physical retail in Soho and a transformative radio ad campaign. He also reflects on navigating the brand through financial hardships during the COVID-19 pandemic, showcasing resilience and adaptability in the ever-changing fashion industry.
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Genesis of Untuckit Idea
- Chris Riccobono wore the same J.Crew shirt out in Las Vegas four nights in a row because it was the only one that looked good untucked.
- He realized this was a common problem among his friends and decided to start a business making shirts designed to be worn untucked.
Early Manufacturing Struggles
- The first batch of Untuckit shirts made in Poland was low quality and had major defects, like shrinking irregularities and poorly attached buttons.
- Despite negative feedback, Chris sold the shirts, learned from mistakes, and gradually improved product quality over several years.
Importance of Shirt Length QC
- Maintaining tight quality control on shirt length is critical for Untuckit's product promise to work consistently.
- Shirts off by even an inch in length ruin the untucked look and brand identity, so reject out-of-spec shirts rigorously.