Billy Dec, the hardest working man in Chicago

If a Chicago version of “Where’s Waldo?” was ever created, it likely would feature a middle-aged, baby-faced man with dimples who wears a hat and gym shoes instead of a red and white sweater. And of course, it would have to be called “Where’s Billy?” 

That’s because Billy Dec is all over the place, all the time. At 42, Dec is a veteran of the restaurant and nightclub scene, working his way from doorman at Shelter while in law school at Chicago Kent College of Law, to CEO and founder of Rockit Ranch Productions; which owns Rockit Bar & Grill, Sunda, Rockit Burger Bar, Underground, ¡AY CHIWOWA OUTTA BIZ! and Bottlefork. In addition, Dec is a regular on Windy City Live, Good Morning America and has been acting for years — mostly in bit parts thus far but with an eye on larger roles. A Filipino-American and tireless philanthropist, Dec has done a lot of charitable work over the years and last May was appointed by President Obama to the White House Advisory Commission on Asian Americans and Pacific Islanders. 

Currently Dec’s latest project, “Big Night Out,” will premiere July 9 on the FYI network.  “Big Night Out” is a show where Dec and co-host Camille Ford must eat and drink their way through a city in 24 hours, relying solely on  recommendations from social media while avoiding tourist traps.  The first episode takes place in Portland, Maine.

Dec recently spoke with The Chicago Ambassador about “Big Night Out” and all his projects in a rare, in-depth discussion that went beyond promoting anything. The hardest working man in Chicago talked about his early days, how he learned from past failures, why he chose the entertainment business instead of working as a lawyer, gave advice to the next Billy Dec and answered the question ‘What’s with the hat?’ 

Interviewed by Bob Chiarito for The Chicago Ambassador.

CA) You always seem to be everywhere, involved with countless projects. Do you ever have a night where you stay home and watch a movie? 

DEC) You know what’s so bad? I do have movies built up that I want to see, and I watch them all when I’m sick. Every once in awhile, I run myself into the ground, which is bad. Especially being out in restaurants and clubs all the time, sometimes you get a cold or whatever and your body just shuts down. That’s when I’ll stay home and catch up. I’m actually pretty organized with my schedule. I really protect private time. I have scheduled hours for non-work time. It seems like I’m doing a lot because I have really awesome partners. I have an amazing assistant for the last ten years; my partners have been with me for 17 years, so that’s really rare. I’m blessed in that regard. But don’t get me wrong, I often do work 24/7.

CA) Your latest thing is “Big Night Out,” which premieres July 9. What is that all about?

DEC) It’s on FYI Network, a travel/cocktail show.

CA) How did that come about?

DEC)  I was on the Today Show cooking and one of the producers saw me and Googled me. He saw a TV reel of mine and called me to see if I’d be interested. I’ve been working for awhile on shows like that, things that came up that never really panned out. Chicago is a wonderful, amazing market that producers keep their eyes on and pay attention to Chicagoans and Chicago things.

CA) As far as your acting, are you still auditioning and working with an acting coach?

DEC)  Yes, a lot. I just auditioned for “American Crime Story,” the Travolta/Cuba Gooding Jr. show. They are doing the O.J. story. I just sent in tape yesterday. I’m grinding from the bottom.

CA) You are also a co-producer of the planned film about the Warehouse with Joe Shanahan and Bob Teitel?

DEC) Bob Teitel is just an awesome Chicago filmmaker. He’s in Hollywood but still calls himself a Chicago filmmaker. Bob and George Tillman have probably made 15 movies now. So, we teamed up with Randy Crumpton, who was Frankie Knuckle’s friend and attorney.

CA) We interviewed Joe Shanahan about a month ago and at the time you guys were still looking for a screenwriter. Have you found one yet?

DEC) Yeah, it’s hard. We haven’t found one yet. It’s hard because we want a Chicagoan, someone who has a tremendous connection to Chicago.

CA) Was House music a passion of yours?

DEC) Yeah. I was born and raised in the city. I went to Saint Clement’s grade school and I remember coming home at 3 p.m., I’d get my homework done so I could hear the “Mix at 6” and my friends and I would tape it on our little ghetto blaster that we had. We’d decorate the tapes and trade them at school. That was my experience. Shanahan at the time was at the Warehouse. I kind of came up behind him.

CA) Everyone knows about a lot of your successful projects. Any that have failed that come to mind?

DEC) My first two or three places were social successes but on paper, they were horrible. Back in my 20s, I was doing it to pay for law school. All I needed to do was put food on the table and pay my law school bills and I was happy because I was going to be a lawyer. So I was filling my nightclubs up to do that, but in reality I was running them like a poor businessman because I wasn’t maximizing potential. I realized that I wasn’t strong in the back of the house. I wasn’t a great manager, I wasn’t great at accounting, I wasn’t great at inventory and labor. I was great at marketing and public relations and because I was not good in so many critical areas, my places were closing within two years. By the way, 80 to 90 percent of places close in the first year or two, and I was definitely one of them. These were actually failures looking back on them, but they were great lessons. They taught me that I wasn’t good in certain areas and it led me to finding amazing partners like Brad Young and Arturo Gomez who are super strong in those areas. We’ve been together for 17 years. And it taught me that I needed to go back to school, so after law school I went to the Harvard Business School and I learned how to keep a company going, management structures, mission…

CA) Do you ever use your law degree?

DEC)  I have a great ability to understand what’s going on business-wise and see what I want in a contract or lease. I can communicate how I want to see it to my lawyers, which is nice advantage. I don’t actually practice. The reason why I’m not practicing law is because I don’t like it and I’m not that good at it. You have to be invested. I know what I’m good at and know what I’m not good at.

CA) Last year, you were appointed by President Obama to the advisory commission of the White House Initiative on Asian Americans and Pacific Islanders. What was that like, and what is your role?

DEC) It was surreal. My mom was born and raised in the Philippines and I grew up in a Filipino household. I’m super proud of my family and heritage and have been back and forth to the Philippines quite a bit. I’m really integrated into the Filipino community in the Chicagoland area and have been so. About 12 years ago I was introduced to this commission that the White House had and at the time I was really shocked that they had something like that. I always felt like an outsider, a minority that no one really paid much attention to. In the 80s it wasn’t cool to be Filipino or Asian. I look ethnically ambiguous. When I go on acting auditions I ‘m playing Latinos, whites, American Indians. I’ve played blacks, I’m never playing Asians. So, it’s cool that the White House has this commission. I stayed in touch with them and I like it also because it lasts past whoever is President. I let them know what I was doing, like when the typhoons hit the Philippines, I was doing quite a bit of fundraising and went there to help build houses. I think they caught wind of it and quite honestly, I think they wanted someone from the midwest on the commission.

CA) Does the commission take up a lot of your time?

DEC)  It does but doesn’t feel like it because it’s full of passion and current events. I even signed up for extra things. I joined the White House Bullying Prevention Task Force and there is quite a bit of reading, speaking at schools, writing emails, conference calls, but it doesn’t feel like work. I’ve been bullied, I know bullying is 20 times or more worse than it was when I was in school because of social media. Somewhere along the line, probably three or four years ago, I was doing quite a bit of philanthropic work and I felt like I was helping but not really going all-in. I was looking around Chicago and trying to think of something that I could do and then I learned about this White House Commission. It’s so nice.

CA) I saw a picture of you at the White House and it was a rare occasion that you weren’t wearing a hat. What’s the deal with the hat, Billy?

DEC) I just like hats. I like hats and gym shoes. I was in law school by day and night clubs by night; not sleeping, I didn’t have a couch or TV for seven years. I just ran in and out of my house to shower and would throw on a ball-cap and gym shoes on. That’s how people got to know me and they accepted it. People let me be what I wanted to be and if they didn’t, then maybe I didn’t like that place. I just felt like being comfortable. I think it’s kinda like a chef coat. Some chefs wear them when they aren’t cooking. The best part though is that If I go to a grocery store or walk by people without a hat, I’m not bothered.

CA) Not bothered if you’re not wearing it?

DEC)  Yeah.

CA) Because it’s kind of become your trademark?

DEC) I guess.

CA) Do you ever worry that you are involved in too much and that you’ll neglect something?

DEC)  Yes. You know, I’ve learned in school and also by trial and error and failing like the stories I’ve told you. I will neglect if I take on too much which is why I tend to keep bringing on partners who are better than me. For instance, I started a film company called Elston Films to help bring more films to Chicago because I was tired of all these projects not picking Chicago and those that did would cast all the leads and bring all the back of the house into our city to make these movies, leaving people like myself and all these amazing local actors to only have tiny parts. So I created this company to help bring more directors to Chicago and I have a couple great partners to help me with it.


Scenes from “Big Night Out,” which makes its premiere on July 9

CA) As successful as your business ventures have been, you’ve always been very into charity work. Why is that important to you?

DEC) My family came from nothing and then they made a lot and then they lost a lot. We were comfortable and then we weren’t comfortable. There came a time when my dad and my brother eventually got sick and I lost them early on. I was the man of the house and I took care of everyone early on, from the time I was a senior in high school. It felt like we had one to two people in the hospital at any time, and there was no money. I was working in restaurants partially to take leftovers home and it just sucked. I hid that for a long time and I hid it because I was scared. I was building an image in a business where business matters. So I hid it, not that it was anyone’s business. But the people who were good to me were the people in the restaurant business. They would take the time to give me extra work, extra shifts. They would teach me things. I just realized Chicago, being a relationship-based city, very communicative and welcoming and very midwestern, allowed me to work my ass off to gain more opportunities. So, in a sense people gave me a shot. If I didn’t get shots or opportunities from people who could afford it in time or money or whatever, I honestly have no idea where I’d be right now. I’d be in really big trouble. So, I made it out by the skin of my teeth and know I’m very blessed.

CA) Because you’re involved in so many projects, what would you say is your number-one passion?

DEC) They all sort of revolve around our mission statement which has to do with delivering elevated entertainment experiences. At one point we didn’t really know what we sold. We orchestrate thousands of different things with amazing teams of top talent, we deliver an entire entertainment experience that is elevated above and beyond what people can get elsewhere. At least that’s what we shoot for. So once I discovered that, I felt like, ‘Wow, that’s it.’ That’s what drives us as a company and what drives me. I try to deliver elevated entertainment experiences every time I’m on Windy City Live or the Today Show. The thing I say to myself before I go on TV in front of 5 million people, about everyone watching, is that I just want to deliver an entertainment experience that is a bit more elevated than what they had before. So, the same with acting, the same with hosting.

CA) That answers my next question which was basically about what connects everything in your mind.

DEC)  Yeah. I thankfully passed the bar on the first try and everything about the way I was conditioned was that ‘You have to become an attorney’ instead of this job that you used to become an attorney, which was working in restaurants.  You put yourself through school to become your profession, it’s what you do for the rest of your life. But it didn’t feel right immediately when I became a lawyer. I kind of broke it down and realized I really like the emotional reaction of people and their faces when I do something nice for them. And I was doing a ton of that in restaurants and bars. I was constantly doing something nice for people and the emotional reaction and immediate gratification was awesome. I learned as a lawyer that you don’t actually deliver that at all, or very rarely. You’re not solving problems quickly. So, it was a choice that I had to make and I knew that I couldn’t do both well. I learned that the hard way because I was sucking at both, but I could have been awesome at either if I just focused. I had to choose one and I chose to give up being a lawyer and took a really big risk on this random idea of, at the time, to elevate the level of hospitality and entertainment in Chicago. I really had a chip on my shoulder back then because I was thinking that New York gets all this attention, along with Miami and Las Vegas and I wondered, ‘Why is Chicago being left in the dust?’ It really pissed me off, it really did and I basically vowed to elevate things, and we did. We went in across from Cabrini Green in the Weed Street district when we opened Dragon Room and Circus. The area was totally defunct. Same with River North. There was nothing at Rockit. It was the only cheap area with rent that I could afford and there was a male prostitute strip on the street. Every night we begged people to come to that area of town, we’d have to call cabs to pick them up at the end of the night because they wouldn’t come there. Now you can’t even park on the streets because there are too many cabs. And that was just a decade ago. We set out to elevate the level of hospitality and I really think River North is not only the greatest entertainment district in Chicago, but probably in the country. That’s literally something we set out to do and whether we did it or not, it was something we set out to do a decade ago.

CA) Is there anyone that you could point to and say you’ve modeled yourself or business model on?

DEC)  No, but I’ve taken a piece from a thousand people. All the networking and relationship building is the entire reason the business and I even exist. When I was a doorman I shook everyone’s hand for a reason. It wasn’t because I was going to be a jerk doorman behind a chain. I met everyone and wanted to be their friend because having nothing, you want to have future relationships and potential jobs in the future. I’ve heard a lot of amazing things while interacting with people and I just absorb, I listen. I take bits and pieces from everyone, there are so many great people. I get inspired by so many people. You’ll be surprised, I might take something from you.

CA) Do you ever see yourself leaving Chicago?

DEC) I don’t think so. I’ve had enough temptations over the years. I haven’t because I love it so much but now that this company is not about me anymore, it’s about my partners, I’ll support what they want to do if they want to start opening in different places. I don’t know, but you never know.

CA) What would you tell an 18-year-old who has aspirations of being the next Billy Dec?

DEC) Network your ass off. Today, focus on being in front of as many people as possible and network. Make sure people know you, like you and trust you, which is really hard to do. That’s what I always tried to do. First I’d try to make people know me by initiating kindness, and then they would like you because you’re offering value and they trust you because you’re doing it consistently and not for any other reason but to just give. That’s what I did and that’s what leads to education and the whole part about how I took a bit from everyone and learned. It opens doors for jobs, community building, relationships, it teaches you how to talk and work with people with all different types of backgrounds without a keyboard. That’s what I would do and work for free as much as possible. Don’t be afraid of it. Some kids these days don’t understand why they should do an internship for no money. In my day that’s what we did. I would do three per summer, meet everyone I could, learn as much as I could and be thankful that I had the opportunity to be around people who were actually doing business related things.

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