On November 18, Chris Riccobono, founder of the shirt company UNTUCKit, was the guest speaker at the Delbarton Fathers & Friends annual Night of Dialog. The annual event was a great evening out for Delbarton dads and sons who, after a quick pizza dinner, settled into the Fine Arts Center theater to hear words of wisdom from a classic entrepreneur.

Ken Lain P'27, President of Fathers & Friends, pictured below on left, welcomed guests and shared the stage with Riccobono to field questions from the audience.  “This was an amazing night spent with Chris Riccobono and Delbarton Fathers and Sons, learning about how education, entrepreneurship and work ethic lead to success in the business world,” said Lain.

Riccobono graduated from Providence College and earned an MBA from Columbia in 2007.  A serial entrepreneur, he tried launching dozens of business ideas, including reality television concepts, a sales consulting business, even a dating website.  In 2008, he started a video wine blog called Pardon That Vine which, although a failure, taught him how to launch a website, use social media, and leverage Facebook marketing. “That—plus coming up with the name UNTUCKit—gave me to confidence to go forward with my idea to create shirts that look good untucked,” he says on his website.

But first, he needed a shirt. Other than wearing clothes himself he had zero fashion experience. Developing the prototype took a year of trial and error, and a business school classmate, Aaron Sanandres, the company’s current CEO, helped him develop a business plan and raise $150,000 from friends and family.

The first ten shirts were a total bust – they shrank, buttons fell off – but the team navigated through each problem while still working full-time jobs.

It was clear from the start that people loved the untucked shirt idea. “What a concept, Mom, I don’t have to tuck in my shirt!” The next challenge was marketing the product. In 2013, a modest radio campaign reaped impressive results and the shirt inventory quickly sold out. That’s when Riccobono knew he was on to something.

Quality was the biggest obstacle, then customer service, including how to handle social media customers who, of course, are vocal, both positively and negatively. The company was generating over $20 million in sales by the time Riccobono left his day job. Covid was a challenge, forcing store closures and reducing demand for button-down shirts as people worked from home in PJs. UNTUCKit survived and continued to grow.

Things Riccobono did right: no fancy office space at first, working 20-hour days (instead of hiring more people) and self-funding as much as possible. No rush to raise outside money protected valuable equity up front. “That’s just in our DNA”, says Chris on his website.

His advice to aspiring entrepreneurs is clear.  Rule #1: differentiate yourself. What makes your product unique? Now say it in one sentence. Then find a great marketing platform to broadcast your good news. If you can’t say something different from competitors, find a new idea. The fact that UNTUCKit’s name describes the original product’s main benefit = genius.

Starting a company is hard and painful – like giving birth, gents.  There will always be struggles and, when it comes to entrepreneurs, only the strong survive. They learn to accept and build from their reversals and missteps. Of equal importance, they enjoy the ride, value their autonomy and have a high tolerance for risk.

Today, UNTUCKit’s product line includes pants, sweaters, tees and henleys, sports coats, jackets, vests, shoes and accessories, as well as women’s fashions. Over the years, the company has raised $30 million in funding yet remains privately held, and Riccobono is also a co-founder of the athletic apparel brand Greatness Wins, with athletes Derek Jeter, Wayne Gretsky and Misty Copland.    

We thank Chris Riccobono for sharing his experiences and advice with Delbarton fathers and sons. Surely, some young, aspiring Delbarton entrepreneurs left with far more practical knowledge than they arrived with.