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Meet Danny Shapiro of Scofflaw Group in Logan Square

Today we’d like to introduce you to Danny Shapiro.

Danny, let’s start with your story. We’d love to hear how you got started and how the journey has been so far.
I came to Chicago in 2009 to do comedy writing in Second City. And, over time, I found myself deeper and deeper in the bar world. It was its own diverse community with a roster full of creative, funloving, hardworking, people. And, through this community and an educational class taught within it, I met my business partners. We found ourselves on the same page and an intriguing opportunity in front of us. That opportunity was Streetside, which we bought and turned into Scofflaw shortly thereafter.

So in 2012, Scofflaw was born. We had some idea of what we were doing and enough luck to carry us forward. From there, we opened Slippery Slope, then Sink|Swim, then The Heavy Feather, and The Moonlighter. I oversee the beverage programs and educational curriculum. I love the people in our company and I think that they are one of the best staffs ever assembled. One of the compliments we hear most frequently is how welcoming our staff is.

We’re all passionate about hospitality and I’d say that’s how we got to where we are today.

We’re always bombarded by how great it is to pursue your passion, etc – but we’ve spoken with enough people to know that it’s not always easy. Overall, would you say things have been easy for you?
It hasn’t always been a smooth road. Before we opened Scofflaw (while we were operating Streetside after purchasing it), we had no money and no patrons. We worked all the bar shifts and wondered when we’d be able to get to the next step. We ultimately decided to take a risk and close Streetside so that we could take whatever we could scrape together (in addition to elbow grease) and turn it into Scofflaw.

Sink|Swim was another struggle. We ended up closing it this year so that we could focus on our other businesses. The idea of doing a restaurant appealed to us at first, but the further we got, the more we realized we were out of our league. It was difficult to fail and find our limitations, but it taught us a lot.

So let’s switch gears a bit and go into the Scofflaw Group story. Tell us more about the business.
Our business is hospitality. Drinks and food are important, but I think where we excel is our ability to make people feel at home, whether that’s on a dance floor or a gin bar or 70s cocktail lounge. Our concepts are distinct, but you can always find good drinks that aren’t too fussy.

I think we got put on the map by offering high quality at a relatively low price point. When we first opened Scofflaw, the most expensive thing on the menu was $8. The value was always important to us and we’ve tried to maintain that affordability at each of our concepts. We want people to visit us without a second thought, regardless of income. We’re happy hosting anyone.

Has luck played a meaningful role in your life and business?
Luck always plays a significant role. It’s lucky that we met each other when we did and that Streetside was for sale. It’s lucky that I landed my first gig at a place with cocktails. It’s lucky that we’re living in an era where people care about cocktails. I feel lucky all the time.

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Image Credit:

Dan Segar, Jude Goergen

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