Madison Minutes, a Small-City Indie Newsletter, Joins the Local Media Network City Cast

What Sold, and Who Bought It

Madison Minutes is a local newsletter covering Madison, Wisconsin (population roughly 270,000). It carved “city news” (city hall, development projects, restaurant openings and closings) into terse bullet points and delivered them on weekdays, alongside a comprehensive local events calendar, becoming part of local residents’ morning routine. It launched in April 2021. In July 2023, it was sold for a six-figure sum (low-to-mid six figures, roughly ¥15M+ at ¥150/$1) to City Cast, which operates a nationwide network of city-specific podcasts and newsletters. At the time of the sale, subscribers numbered 18,500, of whom 700 were paying members. The deal was structured less as a business acquisition than an acqui-hire, a buy aimed primarily at bringing on the people, and both co-founders became full-time City Cast employees.

Two People Who Used to Write Cover Letters Together

The co-founders were Hayley Sperling and Sam Hoisington. Sperling graduated from a university in Madison and moved to New York, but never felt at home there; a job opening at Wisconsin Public Radio brought her back to Madison. Hoisington lived in Washington, DC, a city he describes as “expensive just to be alive in”, working remotely for the journalism nonprofit News Revenue Hub, until he moved to Madison in the summer of 2019, a city he’d “always loved” since spending a summer there as a student. The two connected through a Slack community for audience-engagement professionals, and in 2018 Hoisington had already invited Sperling into a Twitter DM group for young journalists. Online friends became residents of the same city.

The turning point came in the fall of 2020. Sperling had left journalism that year for a marketing role at a local tech company, but COVID-19 cost them both their jobs. “He’d come over to my apartment and we’d write cover letters together. We were glued to LinkedIn around the clock. Having a companion helped, but it was an endlessly frustrating time,” Sperling recalls. Applications went nowhere, and in April 2021 Hoisington launched his own outlet, Madison Minutes. “There was a real opportunity for the kind of newsletter that was happening in a lot of other cities, and Madison didn’t have one. I wanted to build the morning newsletter I’d want to read myself.” Sperling joined as co-founder a few weeks later.

The Household Economics of a 3.8% Conversion Rate

Lining up the numbers at sale time shows the business’s real shape. Against 18,500 subscribers, only 700 were paying members, a conversion rate of about 3.8%. That’s not a scale that supports two people’s living expenses on subscription revenue alone. In fact, in the early days the two supported themselves with side work: Hoisington through freelancing and COVID testing, Sperling through service-industry jobs like food service. When money got tight, Hoisington even drew down his 401(k), a US retirement account, taking advantage of pandemic-era withdrawal-penalty relief (Sperling is careful to note, “I did not recommend that”).

What actually kept the business running wasn’t subscription revenue. It was “the ability to secure outside funding.” They landed funding through Facebook’s (Meta’s) Bulletin program for local outlets that covered Sperling’s stipend, secured journalism grants, and from June 2022 a Poynter-Koch Fellowship, found by Hoisington, applied for by Sperling, supported her going full-time. Sperling describes her partner as “genuinely good at finding money.” At the same time, they never sold any equity. Threading together America’s patchwork of local-journalism funding infrastructure (platform support grants, foundation grants, fellowships) while never giving up ownership is exactly the design that let the two of them keep 100% of the sale proceeds two years later.

Advertising revenue didn’t come easily either. “The only way to know what people would want to buy was to actually try selling something,” Hoisington says. Through trial and error, both display advertising and sponsored content eventually sold, and with no competing local newsletter in the market, they could charge a premium. Revenue figures were never disclosed.

What City Cast Actually Bought

The buyer, City Cast, is a national network running a local podcast plus newsletter in each city. The relationship didn’t start as an acquisition. It began with Madison Minutes reaching out with “want to do this together in Madison?” City Cast hires its own local podcast team in each market and operates alongside outlets like Madison Minutes as an independent partner. “We were kind of like journalism best friends,” says Sperling.

In the spring of 2023, City Cast made its first acquisition offer. The two talked to other potential buyers before choosing City Cast. “It was clear they wanted not just the Madison Minutes brand, but us.” After the acquisition, Sperling continued writing Madison Minutes as a City Cast employee, and Hoisington became the company’s membership director companywide, tasked with rolling out the model that produced 700 paying members in one city across the other 11 cities in the network. “Two people who were unemployed in 2020 are now fully employed, with health insurance, at a new company we’re genuinely excited about”. That’s the substance of this exit. Entering a new city by buying an established local list and writer is faster and more reliable than building from zero, which is why outlets like Madison Minutes find buyers. Including 6AM City, which bought Austonia (Austin), multiple companies in the US are now racing to roll up local media.

“A Bad Time to Sell Media” — In the Founders’ Own Words

Reading this as a straightforward success story requires some caveats. Both founders acknowledge this deal was an exception in their industry. “It’s a pretty bad time to sell media businesses,” says Hoisington. Media companies could once sell for 3–5x revenue. Deals like that have become rare. This one happened because of an existing relationship built through partnership, plus the coincidence that City Cast happened to be hiring for a head of membership at exactly that moment, for other media entrepreneurs, his own read is that finding a local partner is a more realistic path than a sale.

The six-figure consideration bottoms out around $100,000 (roughly ¥15M). Split two ways, that’s not a large sum for 2 years and 3 months of labor and unemployment risk. The essence of an acqui-hire is a “transfer package that comes bundled with employment terms”. It can’t be read as a standalone valuation of the business. And a scale of 18,500 subscribers with 700 paying members never reached the line of independent sustainability. A structure whose continuation was at risk the moment time-limited outside funding like Bulletin or the fellowship ran out. The sale was a win in one sense, and in another, the flip side of a thin outlook for staying independent.

The shift from entrepreneur to employee wasn’t unconditionally happy either. “I didn’t realize at first how much adjustment this would require. Still, for both of us as people and for Madison Minutes as a business, this was the best choice,” Sperling says. The two counsel founders considering a sale to prepare for the emotional side of letting go of a business.

The barrier to entry in local media is peculiar. It requires neither technology nor capital, but living in the town, walking its streets, and building relationships cannot be replicated from outside. In other words, it’s a game of musical chairs with only one or two seats per city, whoever sits down first wins. But that seat isn’t one you can eat from just by sitting in it, Madison Minutes’ numbers show that honestly.

What’s Missing If You Bring This to Japan

In Japan, regional newspapers are declining more slowly than in the US, but the same void is steadily widening. A national network of city-specific newsletters doesn’t exist yet in Japan. That puts the country where the US was ten years before this case, and makes the model well worth watching as a highly transplantable one.

But the conditions for reproducing this need discounting. The funding infrastructure that supported this deal (Meta’s outlet-support program, journalism grants, fellowships) barely exists in Japan, and there’s no standing buyer like City Cast either. Doing the same thing in Japan would require a design that survives the first two years on subscriptions and local advertising alone, a materially harder bar. What generalizes: “the hole left by newspapers can be filled by individuals” and “the know-how of running paid membership is itself sellable.” Reproducing the exit itself, though, is for now something specific to the US.

Related Reading

• Austonia — the same type of local-media sale (a different buyer)
• Microgrid Knowledge — a comparable sale of a niche specialist outlet