There is nothing like a pandemic to temporarily short-circuit a career, which Hayley Sperling well knows. But the experience of losing a job can convince someone to take a chance, which is what Sperling did when she joined Sam Hoisington on the Madison Minutes newsletter in 2021.
After just two years, Madison Minutes — a daily email newsletter focused on city news and events — netted about 18,000 subscribers, had an open rate of over 60%, and became an attractive acquisition target for City Cast, a national network of daily local news podcasts. City Cast executed an “acquihire,” part acquisition, part hire of Madison Minutes personnel in 2023. Its podcasts enabled Sperling, now executive producer, to drill deeper into local stories while continuing to grow the newsletter.
Hoisington left the organization last year, but not before establishing a promising business model with Sperling. A native of Minneapolis, she graduated from the University of Wisconsin–Madison in 2017 and fell in love with the city — so much so that she prefers the lifestyle here to that of New York City, one of her early career stops. In an interview, Sperling talked about life as an entrepreneur and explained why she favors the “Midwestern nice” of Madison.
You’ve come a long way since the pandemic, when both you and Sam lost your respective jobs. Give us an idea of what that two-year, bootstrapping period was like with Madison Minutes.
Yes, it was hard. I’m not going to lie. It was a lot of unpaid hours. … It’s easy to look back with rose-colored glasses and say we were having such a great time and we were doing what we always wanted to do, but that doesn’t negate the fact that we were working really hard.
Personally, I was burning the candle at both ends. I would wake up at 4 a.m. to write the newsletter, send it out by 8 a.m., and then I would go back to bed, take a little nap, and wake up in time for my shift at whatever restaurant I was working at the time. I worked at a few restaurants downtown, and that was also my first foray into the service industry, which actually was the first job that I got after I had lost my job during the pandemic in 2020. I wasn’t sure what to do. … I had some friends that worked at a restaurant in downtown Madison, and I was like, “Hey, will you hire me?” And they’re like, “Yes, you’re a competent human. Absolutely, we will hire you.” So, I got my foot in the door that way.
And then Madison Minutes was not necessarily this passion project that me and Sam were working on and wanted to make into this big business or this big enterprise. … In those two years, we went through a lot of iterations. We went through a lot of changes, a lot of growth, and a lot of learning.
Tell us about the acquihire with City Cast. Madison Minutes was something you and Sam built from scratch. Was it difficult to sell?
It hit us both in different ways and at different times. From the start, Sam and I were just building this and then ultimately growing it enough and selling it to someone who can make it even bigger and better. That was always the dream we had.
We had approached other industry outlets and said, “Hey, we have this opportunity. We have this option and if you’re interested, let us know.” But City Cast, it was just such a natural fit. We approached Andi McDaniel and David Plotz, who are two of the top folks at City Cast … [and said], you guys should really consider the Madison market for a City Cast podcast.
So, they came to Madison. They built up the podcast team. We partnered with them as their daily newsletter product. Madison Minutes wasn’t officially a City Cast product, but we sent out the podcast and we worked together tangentially in that way. And so then, Andi and David came to us in 2023 and said, “We want to have ownership of all of our products,” and we said, “That makes sense.” For us, it was really about looking at the bigger picture and saying, if we want this thing that we built to survive, it has the best chance with something like City Cast.
A newsletter and podcast format could be construed as new media challenging traditional forms of media. Do you consider what you’re doing to be disruptive or complementary?
Madison Minutes was always supposed to be complementary, and I’m talking specifically about the newsletter. Our goal was not to be a new newsroom. We’re not here to recreate the wheel. I do so much respect and value and have appreciation for the reporters that go and sit in City Council [meetings] because we didn’t have the time to do that.
The podcast is a little bit different because it is a new type of media. As far as I’m aware, there is not any other daily morning podcast that exists in the city of Madison, and so we are doing something new.
Being the executive producer of City Cast Madison has been a big adjustment for me because while I started my career at Wisconsin Public Radio [as an engagement editor and social media strategist], I have never actually worked in audio or with audio as a medium. So, it’s completely different going from writing an email newsletter every day to producing a podcast every day, and that is definitely not disruptive, but we’re adding to the media ecosystem in a way that hasn’t really been seen before in Madison.
You’re not a Madison native, but you attended school here, and you prefer the lifestyle here to that of New York City. Why?
When I graduated from UW, I had an internship at Vox Media — it’s Vox with a V, not Fox with an F. … I was 1,000 miles away doing my own thing and not having as much fun. I didn’t have that sense of community, and that’s what I really missed ultimately about Madison and about the Midwest. … I would love to go back and visit [New York]. It’s not a place that I necessarily want to live because I felt the cost of living both financially, but also spiritually, was too high.
