With all the tumultuous change occurring in news media, Chicago appears to find its own unique way to challenge the status quo. Seeing sites such as the Windy Citizen and Chicago Now, it is quite evident that our city is close to the forefront of the future format of news and information. Funsherpa sits down with the brains behind the Windy Citizen, Brad Flora, Princeton and Northwestern alum, Chicago resident, and local entrepreneur. In this feature we learn about the local startup scene, and the future of news from the eyes of the Windy Citizen.
F: How has the concept of the Windy Citizen evolved over time?
B: The Windy Citizen has always been about helping Chicagoans find new things that you otherwise wouldn’t know about. We started with doing editorials through a team of bloggers who would post links and write short articles. We’ve since moved to letting our readers post the links and vote them up and down. We’ve gone from an editorial model to a crowd-sourced model!
F: Anything surprising you’ve discovered about local Chicagoans through the site?
B: I think we tapped into a well of city pride and found there’s a whole scene of people who follow what’s going on in the city – so it has really been fun to see that and provide these people with a forum to share their knowledge.
F: What’s your take on entrepreneurship in the Windy City?
B: There are a good number of people doing interesting things. The environment in Chicago is quite difficult. Chicago is known to be a good place to bootstrap a business. As you get to know people who are starting projects or new ventures, it is pretty rare to find someone who has successfully raised money or even intends to raise money. A lot of cool stuff is happening, but the approach to how you fund and finance that is very different from a lot of other cities.
F: Has there been a time when you just wanted to give up? How’d you resolve that?
B: There are quite a few times that I’ve wanted to give up. I’ve been working on the Windy Citizen for about a year and a half and for the first year or so I wasn’t making any money – so that was a very difficult time for me. It is very easy to get discouraged when you are creating something that you think is cool but nobody else is seeing it. There was a time when the content and design was always changing and I am very grateful to my friends and contributors who have stuck with the Citizen. The thing that really kept me going was finding a couple of people who supported me in developing the concept.
F: Any advice you’d like to share with entrepreneurs?
B: Do your homework. Figure out what you want to do and find the market opportunity. You don’t want to be caught flat footed and not know what your audience really wants!
F: What have you learned from starting up a local media site?
B: One of them is that the market opportunity is a lot smaller than most people think. A lot of people don’t want to think about geography. Their interest is in national stories and national news. Having a population of three million people in a city, doesn’t mean you have a market opportunity of three million people – the audience for us is a bit smaller. At the same time though our audience cares a lot more about what’s going on in the city. It is a smaller market, but we cater to people who are more passionate about things going on locally.
F: With all the talk about new media taking over traditional print, how do you think papers like the Tribune will survive in the midst of bloggers, 24×7 online news sites?
B: Well, The Tribune Company is being very aggressive in the market. They have a Chicago Now site which they’ve turned into a morning radio show. They’ve scooped up a lot of people and are trying to do something interesting.
My expectation is that newspapers will continue trimming costs up to the point they can be profitable. We’ll see smaller more nimble newspapers that may even be published a bit less but they will be profitable.
F: Who are your favorite columnists? What do you like about them?
B: I really enjoy Robert Feder from the Vocalo website. He was the media critic for the Sun Times for 20 years and has now come back to write. His stuff is excellent. Also, I enjoy reading Eric Zorn’s columns. He’s not always covered stuff I’m super interested in, but I’ve really enjoyed what he does. He’s the best and most consistent columnist. John Kass is great too, because he really goes after the creeps.
F: How do you cope with Chicago winters?
B: Working from home is a big start. Its nice when you don’t have to go out in the snow. Second I have a trusty overcoat that I bought in Pittsburg years ago. Between the two of those, I seem to manage them quite well.
F: Can you share with us some of your favorite places to grab a drink in Chicago?
B: I live in Old town. I love going to the Old Town Ale House. At first I was creeped out by the creepy paintings on the walls. I am still creeped out by it. But its got an atmosphere!