How I Built This: Untuckit with Chris Riccobono

Podcast Information:

• Title: How I Built This with Guy Raz
• Host: Guy Raz | Wondery
• Episode: UNTUCKit: Chris Riccobono
• Release Date: June 23, 2025

Introduction

In this episode of How I Built This, host Guy Raz delves into the entrepreneurial journey of Chris Riccobono, the co-founder of Untuckit—a brand that revolutionized men's fashion by popularizing shirts designed to be worn untucked. Chris shares his path from a corporate sales representative to building a thriving apparel brand, highlighting the struggles, pivots, and resilience required to succeed in the competitive fashion industry.

Early Career and Initial Ideas

Background and Corporate Life

Chris grew up in New Jersey, excelling in sports during high school and pursuing a finance degree at Providence College. Post-college, he joined General Electric (GE) in the medical sales department, a role he endured for nearly a decade despite feeling out of place.

• Quote:
  [05:54] "I was so into it. I wanted to succeed in my life. But I knew it couldn't happen in corporate America." – Chris Riccobono

Exploring Entrepreneurship

While at GE, Chris explored various entrepreneurial ideas, including a wine vlog called "Pardon that Vine" and an online dating service for little people (L4LP). These early ventures, though unsuccessful, kept his entrepreneurial spirit alive.

• Quote:
  [14:19] "That's the problem with so many entrepreneurs is following through and actually finishing it and doing it." – Chris Riccobono

Founding Untuckit

Identifying the Problem

In 2010, frustrated with consistently finding dress shirts that fit perfectly when worn untucked, Chris identified a gap in the market. Traditional dress shirts were either too long or too short, leading to an inconsistent and often sloppy appearance when worn untucked.

• Quote:
  [17:41] "Every shirt came down to your mid-thigh unless it was an out of spec shirt. And I had one that fit perfectly." – Chris Riccobono

Developing the Product

Without prior experience in fashion, Chris partnered with Aaron San Andres, a finance professional from Columbia Business School, to co-found Untuckit. Their mission was simple: create high-quality shirts designed explicitly to be worn untucked.

• Quote:
  [21:38] "He's incredibly smart, always asks the most questions. He could put together a detailed financial model and a great PowerPoint." – Chris Riccobono

Overcoming Manufacturing Challenges

Chris faced significant hurdles in manufacturing. Initial batches from a Polish factory were subpar, with issues like shrinking fabrics and faulty buttons. Persistence paid off when they collaborated with Bjorn, a Swedish expert, who helped refine their production process.

• Quote:
  [35:06] "If you make 15,000 white medium shirts, and they put them into a washing machine, a massive tank... scaling makes consistency challenging." – Chris Riccobono

Early Struggles and Growth

Initial Sales and Customer Feedback

Despite manufacturing setbacks, Chris and Aaron sold their first batch of shirts directly from Chris's apartment. Customer feedback was mixed initially, with some using the shirts as rags due to quality issues. However, positive reviews continued to build momentum.

• Quote:
  [32:24] "When people started wearing them and saying they now use it for a rag for their car, that's when it really hit." – Chris Riccobono

Strategic Marketing and Branding

Untuckit gained traction through unconventional marketing strategies, including advertising on sports radio shows like Boomer and the Esiason New York show. Their bold marketing approach resonated with a broader audience, leading to exponential growth.

• Quote:
  [41:55] "You have this tagline, untuck it. Shirts designed to be worn untucked. That's all we had to put." – Chris Riccobono

Expanding Retail Presence

In 2015, Untuckit opened its first brick-and-mortar store in SoHo, New York City. The store's success validated the brand's concept, enabling further expansion to 80 stores and a growing wholesale business.

• Quote:
  [53:52] "The store did so well in SoHo that we opened 90 stores in two and a half years." – Chris Riccobono

Near Acquisition and the COVID-19 Crisis

Preparing for Acquisition

By 2019, Untuckit had established itself as a significant player in the men's apparel market, attracting acquisition interest from major brands. Chris shared his aspiration to sell the company for around $750 million to ensure its longevity.

• Quote:
  [66:24] "I really believe that this is going to be a billion-dollar brand." – Chris Riccobono

Impact of COVID-19

The onset of the COVID-19 pandemic in March 2020 dealt a severe blow to Untuckit. With virtually no new acquisitions materializing due to global uncertainties, the company experienced a drastic revenue decline of 40-50%, leading to financial distress.

• Quote:
  [69:38] "We are scrambling, what's our accounts payable, what's our debt?" – Chris Riccobono

Navigating Bankruptcy

Faced with mounting debts and impaired cash flow, Untuckit had to declare bankruptcy. Despite securing additional funding from their primary investor, Kleiner Perkins, the company struggled to stabilize during the pandemic-induced economic downturn.

• Quote:
  [70:57] "It was the hardest thing to end. We were days away from selling it for such a big number." – Chris Riccobono

Recovery and Current Success

Post-Pandemic Revival

Untuckit recovered by restructuring debts and cutting back on inventory. By 2023, the company reported its most profitable year, focusing on wholesale growth and expanding into international markets like Mexico City.

• Quote:
  [75:43] "We are now having a tremendous 25 and we are beginning our wholesale growth." – Chris Riccobono

Embracing Wholesale Channels

Transitioning from direct-to-consumer sales, Untuckit entered wholesale agreements with major retailers like Nordstrom and Macy’s. This strategic move facilitated broader market penetration and sustained growth.

• Quote:
  [76:09] "Wholesale is part of the long-term plan to scale to a billion-dollar brand." – Chris Riccobono

Sustaining Brand Legacy

Chris emphasizes his commitment to Untuckit’s long-term success, aiming to maintain its status as a beloved, enduring brand. He acknowledges the blend of hard work and luck in Untuckit’s journey, underscoring the importance of resilience and adaptability.

• Quote:
  [78:43] "It's a blend. I think there's no question the hard work, my vision and pushing through and just doing it." – Chris Riccobono

Reflections and Future Plans

Lessons Learned

Chris reflects on the importance of perseverance, adaptability, and strategic marketing in building Untuckit. He acknowledges the role of luck but credits the company's success primarily to relentless effort and the ability to navigate challenges.

• Quote:
  [78:43] "It's a blend of luck and hard work. You need both." – Chris Riccobono

Vision for the Future

Looking ahead, Chris plans to continue expanding Untuckit internationally and exploring new product lines. He remains dedicated to ensuring that Untuckit remains a significant and influential player in the fashion industry.

• Quote:
  [76:09] "I want this to be a brand that way outlives me." – Chris Riccobono

Conclusion

Chris Riccobono’s journey with Untuckit exemplifies the entrepreneurial spirit of identifying a niche problem, relentless pursuit of a solution, and the resilience to overcome significant challenges. From humble beginnings and manufacturing mishaps to near-acquisition and pandemic-induced setbacks, Chris's story is a testament to persistence and strategic innovation. Today, Untuckit stands as a successful brand that has not only carved out its unique space in the apparel market but also influenced broader fashion trends.

Notable Quotes

• "I knew I wanted to be an entrepreneur in college because I was scared about corporate America." – Chris Riccobono [05:54]

• "We play a role into the casualization of the United States." – Chris Riccobono [43:45]

• "Untuckit is like a Kleenex and a tissue and a Xerox machine." – Chris Riccobono [47:09]

This summary captures the essence of Chris Riccobono’s entrepreneurial journey with Untuckit, highlighting key moments, challenges, and triumphs that shaped the brand’s success.