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. You can follow HIBT on Twitter & Instagram, and email us at hibt@id.wondery.com. Sign up for Guy's free newsletter at guyraz.com and on Substack. Learn more about your ad choices. Visit podcastchoices.com/adchoices