UNTUCKit: Chris Riccobono

It's funny, I knew I wanted to be an entrepreneur in college because I was scared of corporate America. I experienced a lot of anxiety in interviews. In my first interview ever, the interviewer at Providence stopped the interview because he could literally hear my heart beating. He said, "I can hear your heart beating. Let's just talk now." So, I was very worried about my career. I kept telling myself, "I'm going to find a way out of this." That was always my approach to post-college life. I planned to get a job, and then focus on finding my own path. I got nervous thinking, "How am I going to work my way up through an organization?" I'm not a great public speaker. I'm not great at Excel or PowerPoint, or all the socializing you need to do to advance. That just wasn't my thing. I knew I wasn't good at it.

Most people hated the name. I came up with it while walking out in front of my parents' shore house. I hadn't even launched the brand yet, but I decided that's why I was doing it. I came up with that name, and I'm going forward with this because I love it. Untuckit. Untuckit is the reason we took off; I truly believe that. The reason it wasn't sophisticated, people would say, is that they're going to think the product isn't great. That's why I said we've got to make the greatest shirt you've ever worn. It has to be perfect. You've got it. Because when you open that box, your mindset is going to be, 'This isn't a super high-quality product because it's a gimmick,' right? That was my fear. So, I needed you right away to say, 'Wow, this is an amazing shirt.' And it washes well, and it holds up because of the name. That was the negative of the name. The positive of the name is now if anyone's wearing an untucked shirt, people call it an Untuckit, period. It's like Kleenex and tissue, or a Xerox machine. That's a great moment as a brand. And by the way, it annoyed so many people in fashion, which is...

Oh my gosh, it was so hard giving up that job. I had a car, I had a job. My parents, my wife, everyone was asking, "Are you going to leave?" I was scared to say, "Okay, I officially don't have a job. I am now an Untuckit employee." The worst part was, it got so bad at GE that it started bothering me. Most people didn't like me. By the way, they didn't dislike me because I was a bad guy. They disliked me because I wasn't going the extra mile, doing a quote right. I was leaning on people. I wouldn't go to meetings because I now had a business. This business, by the way, wasn't doing a lot at that time. It was doing, let's say, 6 or 7 million. And I was like, "But there's a chance here." So I left in 2015. I was flying to our sales meeting, which I did not have time for, because Untuckit was now really taking off. In the magazine was a big picture of me, with the caption: "Shirts designed to be worn untucked. Founded by Chris R. Kobono." When I got there, I guess everyone saw it on the way to Phoenix for the sales meeting.

We were so close. I owned a significant portion of the company because when Kleiner invested $8 million, our main investor was very adamant. They said, "This company is doing well. Do not dilute; let's just raise with debt." So, we took on debt because we had a plan, but we had very little cash compared to what was needed to get through COVID. The bad news was that everything shut down. The worst news was suddenly scrambling to manage accounts payable, debt, and other obligations. Our sales numbers started to drop significantly. The biggest realization was that we had significant cash issues, and they were escalating quickly. Because stores were closing, that meant a very large monthly expense.

I'm a big believer in the importance of luck. It's crucial in every area of life. There isn't a single successful person who hasn't benefited from it. I believe a massive amount of luck was involved in my case because I launched at a time that allowed me to make mistakes and still leverage paid social. One could argue that this was strategy, not luck, but I think it's a blend of both. There's no question that my hard work, vision, and persistence played a significant role. I'd emphasize the importance of simply taking action. So many people just don't do things. Being an entrepreneur is incredibly draining, but it's a mix of luck and hard work. You need both.

We had to sell them; that was the point. Today, that wouldn't happen. I filled my third bedroom with shirts, bought a UPS printer, and we grew from there. I shipped every night from my apartment. We remained positive because customers' excitement was palpable when they received their shirts. We got paragraph-long emails from customers who discovered the brand, saying, "Thank you! I've been looking for this. I can't believe I didn't do it myself. This has been an industry problem." No one writes paragraphs to clothing stores, yet we received them constantly. When the next line came out, I got the first shirt. While measuring it, I noticed a small issue with a button. I pulled it, and it fell off. The next button did the same. I realized the factory forgot to properly tie on the buttons; the machine was broken on every shirt. So, we sold them, then emailed everyone: "Hey, we're reimbursing your account $5. There was an issue with our machine. Take your shirt to the dry cleaner and get them put back on."