Hayley Sperling and Sam Hoisington didn’t plan to live long-term in Madison, Wisconsin.

Sperling had gone to school in Madison, and moved to New York City after graduating. She didn’t love the city, and hadn’t loved the West Coast, either, so when a job at Wisconsin Public Radio opened up in Madison, it felt like the perfect opportunity.

Hoisington, meanwhile, was living in Washington, DC, “where it was simply too expensive to be alive,” he said. The two were journalists who had met in a Slack channel for audience engagement professionals.

In 2018, Hoisington invited Sperling to join a Twitter DM group for young journalists. And in the summer of 2019, while working remotely for the News Revenue Hub, Hoisington decided to move to Madison. He’d spent a summer there during college and “just always really loved it,” he said.

The two internet friends connected IRL. In 2020, Sperling left her journalism job for a marketing position at a local tech startup. Then COVID hit, and by the fall of 2020, Sperling and Hoisington had both lost their jobs.

“He would come over to my apartment and we would work on our cover letters together,” Sperling told They Got Acquired. “We were just on LinkedIn 24-7. It was nice to have someone to go through that with, but it was also so incredibly frustrating.”

In April 2021, after applying to many jobs without success, Hoisington decided to start a local Madison newsletter, and called it Madison Minutes.

“I saw a real opportunity in Madison to do a newsletter like what was happening in many other cities,” he said. “I wanted to create the morning newsletter I wanted to read.” Hoisington offered Sperling some work writing the newsletter, and within a few weeks, they decided she would join the business as a co-founder.

And two years later, in July 2023, they sold Madison Minutes for 6 figures via an acquihire with national news chain City Cast.

Finding money to grow their local newsletter

Hoisington and Sperling bootstrapped their new business while both were initially working other jobs: Hoisington was freelancing and working as a COVID tester, and Sperling was working in the service industry. With restrictions on withdrawals from 401(k)s relaxed due to the pandemic, Hoisington also pulled some money out of his retirement savings. (“I did not advise you to do that,” Sperling noted.)

“If there’s one thing that Sam’s really good at, it’s finding money,” Sperling told us. They joined the Facebook Bulletin program, which provided enough funding to pay Sperling for her work. They also secured some grant funding, yet never sold any stake in the company, Hoisington said. In June 2022, Sperling was able to go full time at Madison Minutes, thanks to a fellowship that Hoisington found and Sperling applied for, the Poynter-Koch Media and Journalism Fellowship.

Sperling broke down each day’s local news and information into easy-to-digest bullet points. They also started a comprehensive local events calendar.

It took some time to generate steady advertising revenue. “The only way to figure out what people want to buy was to try to sell something to them,” Hoisington said. Eventually, they were able to sell both display ads and sponsored content, for which they could charge a premium since there were no comparable newsletters in the local market, Hoisington said. The founders declined to disclose revenue figures.

Growing subscribers on a path to acquihire

Hoisington also developed a successful membership program for Madison Minutes, which grew to about 700 paying members. This put them on a strong footing when they approached City Cast, a network of local podcasts, about potentially working together on a Madison operation.

City Cast ended up hiring out a local podcast team and working with Madison Minutes as an independent partner. “We were like news best friends,” Sperling said.

In the spring of 2023, City Cast made their initial acquisition offer. “It was very clear that they didn’t just want the Madison Minutes brand, they wanted us as people,” Sperling said. She said they did shop around for other offers, but ultimately decided that the City Cast offer was a great fit.

The 6-figure deal was structured as an acquihire, with Sperling continuing to write the Madison Minutes newsletter as a City Cast employee, and Hoisington becoming the director of membership for City Cast, where he’ll build on the Madison Minutes model to grow membership programs in City Cast’s 11 other markets.

“The two of us went from being unemployed in 2020 to fully employed with healthcare benefits at a new company that we’re both really excited about,” Sperling said.

Hoisington and Sperling acknowledge that their acquisition is an anomaly in the media space.

“It’s a pretty bad time to sell a media business,” Hoisington said. In the past, media companies might have sold for 3x to 5x revenue, but those deals have become more rare. The City Cast deal worked because of their previous relationship and because City Cast was looking to hire a director of membership, Hoisington said. Other media entrepreneurs would likely be better served looking for partners in their local markets, he said.

In general, Hoisington and Sperling said that founders should prepare themselves for the emotional side of selling a business and transitioning from entrepreneur to employee.

“At first I didn’t appreciate how big of an adjustment it would be,” Sperling said. “But ultimately, it was not only the best move for Sam and I as humans, but it was the best move for Madison Minutes as a business.”