(Disclosure: I was a writer and editor with Chicagoist from 2004 to 2007 and stayed in close communication with people who worked there up until the time it was sold to DNAinfo. While some of the below is based on knowledge gleaned during that time, none of this is based on off-the-record conversations. For my full ethics disclosure statement, read this.)

Last week, Chance the Rapper announced he’d purchased Chicagoist, a website which covers Chicago news and culture, from WNYC, which bought it from DNAInfo/Gothamist after the local news sites were shut down in the wake of a unionization effort.

Why? And what’s next?

Owning the medium to own the message?

A brief announcement about the sale divulged little about Chance’s plans, but lyrics in a simultaneously released song called “I Might Need Security” perhaps shed some light on his intentions:

I missed a Crain’s interview, they tried leaking my addy
I donate to the schools next, they call me a deadbeat daddy
The Sun-Times gettin’ that Rauner business
I got a hit-list so long I don’t know how to finish
I bought the Chicagoist just to run you racist bitches out of business

Genius can give you the background on the media beefs above and the Chicago Reader’s Leor Galil goes deeper into the issues between Chicago media and Chicago hip-hop.

Of greater concern for Chance’s new venture is the moment last year when Chance pressured MTV News to remove an essay from its website that he and his manager Pat Corcoran “both agreed that the article was offensive,” in Corcoran’s words.

Suffice it to say Chance keeps the media at arm’s length and has been savvy about managing his image, going all the way back to 2013 in this Chicago magazine piece from Jessica Hopper (who coincidentally was MTV News’s editorial director last year):

Chance the Rapper doesn’t want to show me his hood. The burgeoning hip-hop star sits in my car behind the Harold Washington Library issuing a flurry of excuses: It’s too hot. Chatham, the South Side neighborhood where he grew up and filmed his viral video “Hey Ma” (it’s on YouTube), is too far. He has to be at the studio in an hour. Anyway, that place isn’t really his story, he insists. His story is “here,” he says, motioning toward the library.

On one hand, you could imagine Chance is tired of being misrepresented by “the media” and like other savvy cultural creators he’s taken the means of production into his hands to exert more control over his image. The MTV News blow-up, the “Security” lyrics and the Chicago magazine excerpt all lend some credence to this theory.

Also of note is Corcoran’s $15,000 founding member donation to Block Club Chicago, the new hyperlocal Chicago news organization (disclosure: I am also a member of BCC but at 1% of that amount). Considering Chance’s philanthropic endeavors and he and Corcoran’s recent interactions with journalism it’s tough to know whether this is more in line with the former or an attempt to hedge bets on the latter.

To be taken seriously as a funder of independent journalism, he’ll need to address the questions around all of the above. But if I had to guess, I’d imagine he’ll be a media owner more in the mold of a Mansueto or Bezos than an Adelson.

Chance has been an undeniable force for good in Chicago culture. The erstwhile Chancellor Jonathan Bennett is the son of politically active parents whose lives have been devoted to public service. He is seemingly a devoted father, philanthropist and community advocate who has donated upwards of two million dollars to Chicago’s public schools, testified at the Chicago City Council and supported voter registration efforts. When we talk about a music community, it looks a lot like what Chance creates in Chicago by investing in its people.

Chance’s familiar critique of mass media is that it too often misses nuance in favor of an easy-to-swallow narratives and elevates conflict over conversation. Buying Chicagoist could be a way to put create another independent media organization in Chicago, albeit one run by a well-heeled single investor, that serves as a catalyst for the kind of social change he’s been creating.

A business plan for a business, man

Mike Fourcher, a former Chicagoist colleague and also the former publisher of a few hyperlocal news and politics sites, delves into the business and audience side of things in this post. In short, re-building Chicagoist won’t be easy. The business model it had as part of the Gothamist network is lost as a standalone site. With an increasingly mobile audience accessing news via phones, local news sites are competing for attention with not just national publications but also everything that’s in app form whether it’s Facebook, Netflix, Fortnite or text threads.

But with this sale, Chance and Chicagoist will have some valuable assets most startups don’t. When it was shut down, Chicagoist had a sizable social media audience of 500,000 across Facebook, Twitter and Instagram, monthly unique visitors of 700,000 and an email list of 29,000 subscribers. All that’s waiting to be reactivated.

One possible way for Chicagoist to start re-engaging and building on its previous audience is to act as an amplifier/partner of news from the startups who cover underserved-by-news neighborhoods still trying to get to Chicagoist’s size like City Bureau and The Triibe Chicago. This isn’t about aggregating the work of others, but using Chicagoist’s already existing audience to support community engagement.

Going back to Mike’s post, he ends it this way:

Maybe Mr. Bennett wants to turn Chicagoist into a kind of “Players Tribune” for entertainers. Maybe he’d like to use the title as platform for something other than news. Perhaps he is thinking of creating a site about the experience of Black Chicago, a sorely under-reported topic. “Chicagoist” could mean so many things. We shouldn’t limit ourselves to what it’s meant in the past.

All of which leads to one a couple key questions: What is Chicagoist’s voice going to become and what does its audience need and want?

I have a few thoughts on how to answer that.

What could Chicagoist be?

If he has the time, team and treasure to invest, Chance’s Chicagoist could be an exploration of, and a check on, emerging power in Chicago: who has it, how they use it and what are the ways that power affects the everyday lives of Chicagoans, particularly those on the South and West sides who often find a surge of interest in their concerns when something goes wrong, but not as often when something goes right. How is power being used for good as well as for destruction?

It shouldn’t be another variation on “watchdog” reporting though. It can, and should, be celebratory. Imagine this article as an ongoing content vertical with products and events built around it. Billy Penn is already doing something like this with Who’s Next in food, music, the law, education, schools, etc. Someone else will try it here if Chance/Chicagoist doesn’t.

Crain’s Chicago Business covers established power with a specific downtown focus and a high-income audience. Daily papers do this for politics and big business. Local publications cover some of this in a breaking-news, scoop-driven way. But it’s rare to see, for example, a deep dive into the history of a longtime neighborhood developer building condos with first-floor retail in a neighborhood that isn’t on a “hot” list. Not to mention those just coming up.

There’s also something to be said about being a voice for those whose views often go underrepresented in this city. Chicagoist could be the source that represents Pilsen and Humboldt Park and Jackson Park in the way that the Tribune represents…well, often, the western suburbs, bridging the gap between young progressives and older, passionate Chicagoans. It’ll mean taking stands, reflecting the grit of the city, avoiding both the middle ground and “both sides” reporting – pointing out truth, lies and agendas.

This kind of voice would mean elevating people on the front lines of these community issues, making sure the audience sees itself reflected in what’s discussed and giving the readers a stake in it, which increases relevancy, word of mouth and audience size.

We see these voices all over social media. They are guiding the conversation and too often the traditional news media products are playing catch-up to them or just throwing up a screenshot without delving into context. They should be a part of what Chicagoist does, even if, or perhaps especially if, it doesn’t involve traditional journalists.

While the Tribune seems to have cornered the market on op-eds by people who are leaving Chicago and Illinois, Chicagoist has an opportunity to talk about why people stay here and build. Young entrepreneurs who have never set foot in 1871 are creating businesses here. The national political organization Run for Something had an event here last year that was even larger than one in D.C. Who attended, why are they running? Can we track their campaigns in a way that is shows the path and doesn’t follow the patterns of who’s-winning-who’s-losing, horse-race journalism?

When we do this, we find:

• The next lead-contaminated pipes before they harm the brains of our kids and make them more susceptible to violence
• The next models for entrepreneurship in neighborhoods which others can replicate and build a hyperlocal economy
• The next political movement leaders
• The next…Chance the Rapper

It’s about giving the audience an understanding of power and how it’s used but also in reinvigorating the trust between reader and publisher by demonstrating that we’re listening to what they need, not just telling them what we think they need. Hearken, a Chicago startup with national reach, has been pioneering this approach. I’m surprised more newsrooms aren’t using their tech and process. Also, City Bureau’s public newsroom collaborations have showed that developing news products side-by-side with readers has tremendous value for the end product and develops audience loyalty.

This starts with research on not just on the previous Chicagoist audience, but also its potential readers – the ones who stepped away from Chicagoist and the ones it never appealed to – as well as the places they live. The geographic communities and the psychographic communities – their interests and needs. What do they need out of a media publisher vs. a mobile website vs. an email product vs. a social feed vs. ongoing coverage of a topic that’s created for the place in which it appears.

But more importantly, it allows Chicagoist to own the relationship with its readers and reinvigorate the entire model of useful products and information given to readers in exchange for trust, money and information about themselves. It takes work, but it’s how you develop a true business model.

It also makes the content actionable for the audience. For someone with Chance’s philanthropic leanings, a media organization that consistently says “If this is important to you, here’s what you can do…” could be an important next step.

Correction: A previous version of this article listed Pat Corcoran’s Block Club Chicago contribution as $10,000 based on this page. Block Club Chicago Director of Strategy Jen Sabella says the actual amount was $15,000 and said that “Pat’s contribution to BCC was not on behalf of Chance…he just liked/missed his neighborhood news and wanted to help us get going again.”

Image of Chance the Rapper by Flickr user Julio Enriquez licensed through Creative Commons