How a former Yahoo Sports editor built his own paid newsletter

Simon Owens
Mar 1 · 6 min read

Kevin Kaduk didn’t know in advance that he’d get laid off from Yahoo Sports, but he always understood that such an outcome was more than possible. After all, he’d spent pretty much the entirety of his career watching friends and colleagues lose their media jobs. “I think when you’re a modern day journalist, you’re always thinking one or two steps ahead,” he told me.

Kaduk’s focus at Yahoo spanned across all major sports, but he’d always been particularly obsessed with Chicago athletics, and over the years he toyed with the idea of launching a publication called Midway Minute — a reference to one of Chicago’s international airports. So in October of 2019, just a few short months before he received his pink slip, he approached a cousin who worked in graphic design. “I said, ‘look, I’ve got this idea. I’ve got this name. Can you work up a logo for it?’” he recalled. “That way it’d be ready if there ever came a day when I needed it.”

As it turned out, that day came sooner than he anticipated. By that December Kaduk was laid off from Yahoo, and just under two months later he announced his newly-launched publication on Substack.

Building an early audience

Kaduk readily admits that he didn’t have a fully coherent business strategy when he launched. “I knew what the newsletter wanted to be, but I don’t think I quite mapped out everything from its marketing to audience growth strategy at that point,” he said. “I kind of wish I would’ve taken maybe another month or two to really dig into it and talk to people who’ve already done it.”

Still, Kaduk had a pretty strong grasp of how online audiences consume sports journalism. He’s been in that world for over 20 years, starting off as a columnist for various daily newspapers before landing at Yahoo. He was hired on there as a baseball blogger and then gradually moved up into a managerial role that involved overseeing a team of bloggers, making videos, and starting up a podcast network.

Kaduk also had the benefit of an already-existing brand and network. Not only did he have a 10,000+ Twitter following to promote his new newsletter to, but several of his colleagues, each of whom had huge social media audiences of their own, plugged Midway Minute after its launch. He collected several hundred email signups before he even sent out his first issue.

Of course, his timing was a bit awkward; Kaduk announced Midway Minute on February 10, and it was almost exactly a month later when he sent out an issue titled “Things are getting pretty real.” The day before, Jazz center Rudy Gobert had tested positive for Covid-19, and everyone quickly recognized that live sports were pretty much over for the foreseeable future. Kaduk suddenly found himself trying to grow a sports newsletter without any actual sports to cover.

Oddly enough, however, he still found plenty of stuff to write about. “I used it as an opportunity to write more featurey, nostalgia-based stuff,” Kaduk said. In April, for instance, ESPN debuted The Last Dance, its blockbuster Chicago Bulls documentary mini-series. With each new episode airing on a Sunday, that provided him with five straight weeks of Monday newsletters to discuss the show. “At this point, sports have been back for about six months,” he said in our recent phone call, “but I almost kind of feel like it was easier to write about sports when there were no sports going on.”

Pivoting from Substack

Kaduk quickly fell into a writing cadence, publishing upwards of six times a week. As his email list slowly-but-steadily grew, he began to think through how a paid subscription offering would work. It didn’t take him long to conclude that he didn’t want to build the paid version on Substack. “I just didn’t really like the look of it,” he said. “I wanted a custom domain, and this was before they provided that option. I wanted the ability to segment my audiences. I wanted the ability to run a referral system. I also didn’t think they were providing enough to earn a 10% cut of my earnings.”

So in early August he moved off Substack, using instead a cobbled-together tech stack that included Squarespace, MailerLite, and Stripe. He also adopted a tool called SparkLoop, which allowed him to set up a referral program to incentivize his followers into recommending his newsletter to others. Essentially how it works is that participating subscribers are given their own personalized referral link that tracks how many signups they drive, and once they hit a certain number they’re then asked to enter in their mailing address so Kaduk can send them Midway Minute-branded stickers, koozies, and mugs. He attributes about 10% of his list growth to this program.

Rolling out a paid newsletter

Kaduk landed on a fairly straightforward paywall strategy: he would continue publishing five or six times a week and simply move a handful of those issues behind the paywall. He decided to price the subscription at $50 a year, but after launching the paid newsletter in the early Fall he immediately wished he’d done more research ahead of time. “If I were to do it over again, I would’ve liked to do a survey to figure out what this was worth to people, and how many would consider paying for it. It ended up feeling like I was building the plane while I was already in the air. It was crazy.”

As Kaduk works on converting more and more free subscribers into paid, he continues to tap into new growth channels. He counts himself lucky that he’s regularly invited onto local radio shows to provide commentary — he estimated that each appearance drives up to 10 new subscribers — and he recently teamed up with a friend of his to launch a YouTube channel. “We’ve been doing Bears game recaps every Sunday night and game previews every Friday,” he said. “I’m old, I’m not really a YouTube person, but I’ve been really shocked at the amount of engagement and number of views that we’ve seen. It’s not like it’s in the tens of thousands, but I’m shocked that we’ll get up to 1,800 views on a channel that we just started with no promotion. I guess it’s just the YouTube algorithm and people typing ‘Bears and Packers’ into the search bar.”

Now that Kaduk is approaching the one-year anniversary of his newsletter’s launch, he’s starting to feel more confident that he’s producing real value for his readers. “2020 was about learning how this works and building the brand,” he said. “And I think 2021 is really going to be a lot about fine tuning the strategy. I think it’s sustainable, and my challenge moving forward is just really reaching that regular fan and getting in front of them and demonstrating this newsletter really should be part of their media diet.”

I asked Kaduk if The Athletic or the Chicago Tribune came to him tomorrow and offered him a job, would he take it? “I’m open to any offers I think, but I am really loving working for myself and seeing my own dream take root,” he said. “I think part of the reason that I did go down this route instead of looking for another job was because I didn’t like the feeling of working someplace for 12 years, only to see a line drawn through my name. At some point you just want to have something to call your own.”

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