Casual Conversations: From TV Shows to Fashion and Music

Ken interviews Chris Riccobono, Co-Founder and Executive Chairman of Untuckit., one of the fastest-growing men’s retail brands in the U.S.

After earning his Bachelor’s degree from Providence College in 2001, Chris began his career at GE Healthcare and enrolled in Columbia Business School in 2007. While working towards his MBA, Chris thought of the idea for UNTUCKit after speaking with lots of men about their fit problems—especially the length of their collared shirts—and began the business from his apartment in Hoboken. It began as just a side job, but once Chris and his early customers realized that he’d solved a big problem in men’s fashion, the business quickly grew beyond his expectations—with a compound annual growth rate over 100% each year—into the brand we know today with more than 50 retail locations by the end of 2018 and an entrance into the international market.

In addition to furthering his education and growing the brand, Chris dedicated time to sharing his passion for wine through a video blog called Pardon That Vine, traveling the world interviewing winemakers, and teaching beginners about wine. Chris was a winner of the Entrepreneur Of The Year® 2018 Award in New York and in his spare time he works closely with the Cancer Center at Atlantic Health System in New Jersey.

Chris currently lives in New Jersey with his wife and children.

1. Untuckit's Origin and Chris Riccobono's Journey: Chris Riccobono, the co-founder of Untuckit, started the company with the idea of creating a shirt designed to be worn untucked, addressing a common problem in men's fashion. The concept emerged from Chris's frustration with traditional shirts being too long, and he decided to venture into the fashion industry despite having no prior experience in the field.
2. Struggles and Early Challenges: Untuckit faced initial challenges, including the difficulty of finding the right shirt length and manufacturing issues. They encountered setbacks like shirts shrinking and buttons unraveling. Chris and his partner struggled to make a quality product and initially had limited resources, raising a modest amount of money to launch the brand.
3. Marketing Strategies and Growth: Untuckit adopted unconventional marketing strategies, such as radio ads and airline ads, to promote their unique product. The tagline "shirts designed to be worn untucked" resonated well with the audience. Despite the slow initial growth, Untuckit's brand strength and customer satisfaction led to significant success, with a focus on brick-and-mortar stores alongside online presence.
4. Impact of the COVID-19 Pandemic: The podcast covers the unexpected challenges Untuckit faced during the COVID-19 pandemic. The company went from a position of rapid growth to considering bankruptcy within a few months. Chris highlights the importance of resilience and adaptability in overcoming the challenges posed by the pandemic, which significantly impacted the fashion industry.
5. Current and Future Plans: Despite the challenges, Untuckit managed to survive and adapt. Chris discusses their recovery strategy, including negotiating with landlords and factories, raising debt, and ultimately becoming profitable again. Untuckit is optimistic about the future, planning to open 20-25 stores, exploring international markets, and diversifying into wholesale. The company aims to continue its growth trajectory and capitalize on its brand strength.
6. Efficient Store Strategy: Chris emphasizes the importance of efficient store design and operations. He prefers stores in the range of 1,200 to 1,500 square feet, with a focus on cost-effective buildouts. The goal is to provide a productive and efficient shopping experience.
7. Move Away from Large, Expensive Stores: Chris challenges the tradition...