By Dan Michel


Million-dollar ideas don’t come around that often. And even when they do, countless roadblocks can keep entrepreneurs from bringing them to life. After UNTUCKit founder Chris Riccobono struggled to launch dozens of business ideas, he was ready to return to the finance world—until he had the idea to make shirts that look good untucked, a concept that was almost too simple to legitimize an entire business. Here, UNTUCKit's founder shares the genesis of his concept, how he funded his endeavor, and the roadblocks almost kept his untucked idea from taking off altogether.

Untucked Magazine: We heard you once started a wine blog. How do you go from that to starting an apparel company?

Chris Riccobono: I've always wanted to be an entrepreneur. I tried every idea that came to mind—reality television concepts, a sales consulting business, and even launching a dating website—and had zero luck. In 2008, I started a video wine blog called Pardon That Vine, which ended up going nowhere, but I learned 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. But I was still scared, as I didn’t have any experience in fashion or launching a company, which is the hurdle that holds back every entrepreneur.

Untucked: How does someone with zero experience in fashion start a clothing company?

CR: So, the first thing I did was try to make the actual shirt. I started wandering the fashion district to find people who would make this shirt for me, and it was way harder than I thought. I figured getting the right fit would take a month—it took a full year and more than a dozen shirtmakers to figure it out.

The next thing I did was call up Aaron Sanandres, our current CEO and a classmate of mine from Columbia Business School, and pitch this idea like I had all the others. Usually, he would say “terrible idea” and hang up. This time, he said he was in before I even finished talking. So, we began to build a business plan and raised $150,000 from friends and family. We found a small factory that could make the shirts, and we launched with ten. They were terrible. They shrunk. Buttons fell off. There were a lot of growing pains throughout the process, but we worked through them.

Untucked: When did you know you wanted to go all in on this company?

CR: Once we improved the shirts, we launched in June 2011. At this point, I was still working a full-time job, then going home at working on UNTUCKit. We had this great initial response. One out of every ten people who bought would email us to say, "You solved my problem. Thanks so much." The problem was we we weren't selling enough shirts because we weren't reaching anyone through marketing.

In 2013, we started a modest radio campaign—it was all we could afford. The response was incredible. We’d have 1,000 people come to the site after each read, and we sold out of shirts very quickly. Right then, we said, "Okay. We have something here."

Untucked: What was your biggest obstacle when launching this brand?

CR: There were a lot. Overall, the biggest obstacle was quality—meeting specs for the factories and making sure each was up to our standards. But also, starting an apparel company with no fashion experience. I was learning on the fly while trying to run a business. Learning about fabric, finding buttons, and even getting a factory to produce the shirts was a challenge.

Untucked: In your path to becoming a jack-of-all-trades, what was the toughest responsibility?

CR: Customer service and how you're supposed to handle customers in the age of social media. I did it full time for the first two or three years, and it was difficult because customers have a major voice with social. They can really impact your company. Their expectations are very high when it comes to shipping and the product itself. But with any small company, you're going to make mistakes.

Untucked: If you had to do it all again, what would you do the exact same? 

CR: We didn't rush out to get an expensive office just to feel good about ourselves. We worked 20 hour days, as opposed to hiring. We didn’t rush to raise a lot of outside money and therefore lose a lot of equity up front. Our plan was not to spend a lot of cash and fund from within. That's just in our DNA.

Untucked: What’s your advice to aspiring entrepreneurs?

CR: First, you need to differentiate yourself. It’s really easy to start a business now, but you need a major differentiator and you need a great marketing platform to broadcast it. If you can’t say in one sentence what makes you different from your competition, then you're wasting your time.

The second is to understand that when you're starting a company from scratch, there's going to be a lot of pain, and a lot of struggles. I only wish I had enjoyed that part of it more as opposed to getting upset and worrying. There's always gonna be a step back—that shirt that’s out of stock or that advertising that doesn't work. You have to learn from those mistakes, but you also need to enjoy the ride.