UNTUCKit: Chris Riccobono

On a trip to Las Vegas, Chris Riccobono found himself wearing the same J.Crew shirt over and over; it was the only dress shirt he had that looked good untucked. All of his other button-downs were too long and looked sloppy. His buddies all said they had the same problem, so Chris decided to seize the opportunity and launch UNTUCKit with a friend. Keeping his day job as a  GE salesman, he embarked on a crash course in how not to make a shirt. Thousands of defective button-downs later, UNTUCKit hit its stride, and the big fashion brands began to copy the untucked look. In 2020, UNTUCKit came within inches of a lucrative acquisition, then nearly went bankrupt, but today has grown into a thriving brand. 

This episode was produced by J.C. Howard, with music by Ramtin Arablouei.

Edited by Neva Grant, with research help from Kerry Thompson.

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Guy Raz interviews the world’s best-known entrepreneurs to learn how they built their iconic brands. In each episode, founders reveal deep, intimate moments of doubt and failure, and share insights on their eventual success. How I Built This is a master-class on innovation, creativity, leadership and how to navigate challenges of all kinds.

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