Just seven years ago, Chris Riccobono was selling medical equipment and, in his spare time, producing a wine-focused video blog, Pardon That Vine. Today, UNTUCKit, the apparel company he and buddy Aaron Sanandres founded in 2011 with $250,000 from friends and family, is poised to top $100 million in annual sales, according to Forbes. But it\u2019s still wine, more than button-downs, that gets Riccobono most jazzed. Here\u2019s the story of a wine-obsessed Jersey Boy making good.\r\n\r\nThe names of many of UNTUCKit\u2019s shirts sound like they\u2019re from a wine encyclopedia.\r\n\r\nA lot of them were, in fact. We are approaching 500 different styles, and we\u2019ve pretty much expired every known grape type and wine region. When we got going, I could pick up a shirt and tell you the name. Oh, that\u2019s Carter, or that\u2019s Sangiovese. I can\u2019t do that anymore.\r\n\r\nHow did UNTUCKit come about?\r\n\r\nI knew that a career in corporate America wasn\u2019t for me. But you have to find your way, and one day I called a friend from business school and asked him, \u2018Do you ever wear your shirt untucked?\u2019 And that\u2019s how it began. We launched a line of men\u2019s shirts meant to be worn out while not looking baggy and sloppy.\r\n\r\n\u00a0I really prefer to do my serious wine drinking at home.\r\n\r\nUNTUCKit began as strictly an online retailer. Now you are opening stores at breakneck speed. How have you evolved so quickly from internet-only to clicks and bricks?\r\n\r\nWe started with maybe 10 designs, which were pretty terrible because they shrunk and the buttons all popped. Back then, I was cruising around New York\u2019s Garment District, trying to find somebody on 37th Street to make shirts for us. I knew nothing then about prewashing and preshrinking. Now we work with factories [around the world]. We also recently received $30 million in venture capital, which has helped us expand into women\u2019s wear and clothes for kids. We\u2019re naming the children\u2019s line after cheeses.\r\n\r\nHow were you able to get the word out about UNTUCKit?\r\n\r\nWe started at the bottom of the barrel in terms of advertising: local sports radio and inflight magazines. Our first celebrity endorser was the NHL player Brad Richards. Then Patrick Kane of the Chicago Blackhawks started to wear our shirts. The word got out. Guys started to take notice.\r\n\r\nHow did you get into wine?\r\n\r\nMy father went to medical school in Bologna, Italy, so wine was part of my childhood. But that eureka moment took place right after I graduated from Providence College and before I went for my MBA at Columbia. I was invited to dinner at an older cousin\u2019s house, and he has a nice wine collection. He let me pick the Champagne to start the night, then a white wine, then a couple of reds and finally, a dessert wine. That was my moment of awakening. I was done with vodka and light beer, and I started learning about wine and reading about it. I became obsessed. It\u2019s what ultimately led me to doing Pardon That Vine out [of] my apartment [in Hoboken, New Jersey].\r\n\r\nAnd what are you drinking today?\r\n\r\nI collect mostly Napa Cabs, Barolos and Bordeaux, so I\u2019d say I\u2019m more mainstream in my tastes. I also love Amarone and some Spanish wines. To me, the perfect wine would be if you could take some weight off a Napa Cabernet and add some fruit to Bordeaux, then blend them together.\r\n\r\n\r\n\r\nHow big is your wine collection?\r\n\r\nI\u2019m at about 1,300 bottles, but that\u2019s because I\u2019m out of room. Otherwise, I\u2019d have more. I really prefer to do my serious wine drinking at home. Going out to drink aged Bordeaux or a top Napa Cab just isn\u2019t feasible, unless money is no matter. I\u2019m not at that point.\r\n\r\nWhat would be your perfect vacation?\r\n\r\nFall in Piedmont, eating pasta buried in truffles and drinking Barolo. My wife loves Pinot Noir, so I suppose we need to go to Burgundy someday. But honestly, I don\u2019t love Pinot. I prefer Cabernets like Spottswoode, Pride, Larkmead and Carter from Napa. From Barolo, hands down my favorite is Bartolo Mascarello. They have avoided any semblance of going modern. Solaia, Tignanello and Quintarelli are also tops on my Italian list. My dad\u2019s favorite wine on earth is Quintarelli\u2019s Alzero. It\u2019s made like classic Amarone, but from Cabernet Sauvignon, Cab Franc and Merlot. I think Amarone is the one wine that even wine experts don\u2019t fully understand and can\u2019t explain. It\u2019s magical.\r\n\r\nDo you see yourself doing more with wine in the future, maybe even investing in a winery?\r\n\r\nI definitely want the next generation to have a greater knowledge base of wine than I had. And that\u2019s already happening. Every young person seems to know something about wine. To me, wine is the new golf. Maybe I\u2019ll go back and get a degree in wine education or enology. Maybe I\u2019ll resurrect Pardon That Vine and put some real money into it.\r\n\r\nIf you could tell a neophyte one thing about wine, what would that be?\r\n\r\nThat wine turns an average night into a great night. I love something that you can talk about for hours without getting bored.