It’s a bold move in a media landscape that has grown more cookie-cutter even as outlets and options have multiplied.
Steve Dahl, a legend of Chicago radio, will be charging $9.95 per month for his previously free podcast, starting on Aug. 1. Dahl currently attracts more than 17,000 daily downloads of his podcast — I’m among those fans. 
Dahl is most famous nationally for his role in the Disco Demolition fiasco of awesomeness in 1979.
He was essentially fired from CBS radio (while remaining under contract) a couple of years ago, and has been producing a daily podcast from his basement ever since, while paying for staff and technology out of his own pocket. Now that his contract is over, he’s moving to a paywall: $9.95 a month or just under $100 for a year’s worth of podcasts. Dahl has said that he is hoping for 10,000 subscribers in order to make the effort financially viable.
First, I am utterly fascinated to see if this will work. Dahl’s style is unique. The DahlCast is a daily 90-minute affair. It’s a show-within-a-show type of endeavor, with topical humor and a bit of media criticism thrown in (there’s plenty to criticize, especially in Chicago). At first, Dahl seemed to be framing the paywall argument in terms of affordability: almost everyone can afford 10 bucks a month, so, fans, why not sign up? But I think he’s realized that this is not the real issue. Fans aren’t asking themselves if they can afford $9.95 a month. They’re asking if Steve Dahl and his podcast are worth $9.95 a month.
That must be a humbling notion to a guy who has always been a popular and successful broadcaster on traditional radio. But the era of personality-driven over-the-air radio is on its way out. (Have you listened to the radio lately in Chicago, or elsewhere? For the most part, awful.)
In any event, the reaction from fans and media has been mixed. Some of the dumber arguments have taken place on Dahl’s Facebook fan page, although the supporters appear to have rallied and are often drowning out the naysayers at this point.
I’ve put up my $9.95, not only to offer support to The Stever after years of listening to him and his crew, but also to offer my support and encouragement for a bold new idea. It’s one thing to subscribe to the digital Wall Street Journal or something. Dahl connects with fans in a very personal way, and charging for his podcasts is a fundamental shift in how that connection is paid for. I hope it works, but even if it doesn’t, I salute this big leap.