PE049: Nonprofit Podcasting with Stacy Massey from IJ Clinic on Entrepreneurship


“So this is just my advice for anyone who winds up with the exciting prospect of adding a podcast to whatever mix you’re already doing at work. It’s a good idea to be sort of protective of your time and not overcommit because then you’ll wind up doing poorly at your job and at the podcasting.”

Stacy Massey from How’s Business? by the IJ Clinic on Entrepreneurship

Question: What do podcasting, non-profit work, and local entrepreneurship have in common? 

Pick One:

a) They exist despite time & budget constraints
b) They require mad organizational skills & scrappiness
c) They’re fulfilling endeavors, not get-rich-quick schemes
d) All of the above

Answer: Yeah, it’s all of the above. 

Stacy Massey, formerly of the Institute for Justice Clinic on Entrepreneurship (aka IJ Clinic), joined me in the Podcast Envy studio (live! exciting!) for a dive into the d) end.

Our all of the above conversation is packed with tips from Stacy and lessons she learned at the helm of How’s Business?, IJ Clinic’s mission-driven podcast.

Like most non-profits (and podcasts), a majority of Chicago’s small businesses operate in the d) end; think the massage therapists, street vendors, and one-truck moving companies delivering vital services to our communities at razor-thin margins.

Enter IJ Clinic. Their volunteers – law students from the University of Chicago Law School – provide the city’s low-income entrepreneurs with free legal services.

How’s Business? was created to give a literal voice to those local entrepreneurs, documenting how this city’s policies affect their ability to earn a living. 

Read on for more…

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Article Cont’d


“First, I posted the opportunity on Upwork and I had never used Upwork to hire anyone for anything. And I don’t know that I will [again] because there’s so much power in getting a referral from someone that you’re familiar with.”

Stacy Massey, on hiring ME to be their producing editor

The show delivers focused content to a niche audience via eight to twenty-minute episodes – the amount of time IJ Clinic has to hold a policy maker’s attention and, possibly, influence future licensing regulations.  

Like most podcasts, How’s Business? began with big ideas. Those grand dreams were distilled into something nimble enough for a non-profit to develop yet potent enough to support the organization’s work. As a self-professed ham, Stacy leapt at the chance to participate — but she kept her feet firmly rooted in reality. Overseeing the podcast’s creation and hosting would come in addition to her 9-to-5 responsibilities at IJ Clinic, not instead of.

To stay on message and keep deliverables on track, she focused on a few key questions:

  • what does the organization hope to accomplish with a podcast? 
  • what style guidelines need to be followed? 
  • how do we measure success? 
  • which tasks will be accomplished in-house? 
  • should we hire an editor or producer? 

Full disclosure: I’m the show’s producing editor so, of course, I love that she included that last question in the mix. Finding a good collaborator can mean the difference between getting the show up and spending late nights learning a suite of editing tools you’ve no interest in. But I digress. 

By keeping the responses simple and flexible, Stacy was able to manage the project’s scope and create a show that does exactly what it set out to do: facilitate a dialogue between the people who work and the lawmakers who should work for them.

If your contemplating starting a show for your organization, this episode is a great example of the power of podcasting. How’s Business? has extended IJ Clinic’s reach and amplified its message, something I think the medium was born to do. 

Resources, Podcasts & Episodes Mentioned

Check out How’s Business? Podcast episodes:

Just Ice… coming soon! Subscribe so you don’t miss it.
Dearborn Denim

Follow How’s Business? on Instagram @howsbusiness_chi and at http://www.howsbusinesschi.com. If you are a Chicago-based business, reach out and submit your story.


Descript Transcription Software

IJ Clinic on Entrepreneurship

University Of Chicago Law School

Humans of New York

Snap Judgement Podcast

Just Ice, Inc.

The Plant Chicago

Dearborn Denim & Apparel

Cash Considerations: A Chicago Bulls Podcast

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