In this episode of "How I Built This," Guy Raz interviews Chris Riccobono, the founder of UNTUCKit, about his journey in creating a successful apparel brand. Riccobono discusses his initial struggles with corporate America and his early entrepreneurial ventures, including a wine blog and a dating service concept. The conversation covers the inspiration behind UNTUCKit, the challenges of manufacturing quality shirts, marketing strategies, and the near-acquisition of the company before COVID-19. Riccobono shares insights on building a brand, the importance of luck and hard work, and his future vision for UNTUCKit, including expanding into wholesale and international markets.