The Business of Content with Simon Owens

My newsletter: https://thelongstory.substack.com/   The Dispatch was launched in 2020 with a pretty straightforward thesis: that people would pay for quality, fact-based journalism. It certainly had a partisan lean – it was co-founded by conservative journalists Jonah Goldberg and Steve Hayes after all – but it steered clear of the wholesale rejection of reality that’s rampant in most pro-Trump media.   Flash forward to 2025, and that thesis has been vindicated. It recently crossed 45,000 paid subscribers without the help of huge VC investors. Now, it plans to diversify its revenue streams, and to accomplish that it brought on Mike Rothman, a longtime media veteran who helped build companies like Thrillist and Fatherly.   In a recent interview, Mike walked through his decision to join The Dispatch, what kind of advertising he wants to sell, and why brands are suddenly interested again in sponsoring politics media.  

My newsleter: https://thelongstory.substack.com/ When the Manchester Mill launched in 2020, it operated on a simple theory: that local audiences would pay for news as long as it was original and differentiated. It quickly proved that model out and was able to hire its first full-time employee within a matter of months. From there, founder Joshi Herrmann decided to replicate this model across other cities in the UK, and Mill Media now runs six publications that have collectively generated tens of thousands of paid subscribers. In a recent interview, Joshi discussed why he first got interested in local news, how he decided to expand to different cities, and whether he thinks his model can be replicated by other local news startups.  

My newsletter: https://simonowens.substack.com/   When Matthew Schniper launched his Colorado Springs food newsletter in 2023, he ran into a problem many local news entrepreneurs face: he didn’t have enough time to do his reporting and chase down advertisers.   Luckily, by that point he already had strong relationships in the Colorado Springs food scene, and so he approached 12 of his favorite restaurants with an interesting proposition: if they came on as annual sponsors, he would go above and beyond to feature them in his newsletter, and he wouldn’t allow any other local businesses to advertise. This allowed him to focus on his reporting and not waste time on sales calls. The experiment was so successful that over half of the restaurants have already renewed for a second year.   In a recent interview, Matthew explained how he came up with the idea, what services he provides for these 12 restaurants, and why he thinks his model can be replicated by other local news startups.  

My newsletter: https://simonowens.substack.com/ What’s the true monetary value of a newsletter subscriber? Tim Huelskamp knows the answer to that question. As the co-founder of the 1440 newsletter, he knows how many emails the average subscriber will open, how much money they’ll generate in ad revenue, and what it costs to acquire them. It’s this ruthless approach to unit economics that allowed 1440 to grow to over 4 million subscribers, all without raising any VC investment. In a recent interview, Huelskamp walked me through the original idea behind the company, how he and his co-founders generated their first few thousand subscribers, and why 1440 is now expanding beyond the inbox into topic-based explainer content.  

Scott Porch, founder of Big IP, has a dynamic background in law and journalism, now transforming the podcast landscape. He discusses the significant role podcasts played in the 2024 US presidential election and the tough monetization hurdles for indie podcasters. Scott shares his strategies for audience growth, the intricacies of podcast ad contracts, and the potential of paid subscriptions. He also dives into effective content creation on platforms like YouTube, balancing engagement with revenue, and the unique challenges faced by nonprofits in podcast advertising.

My newsletter: https://simonowens.substack.com/   David Stein had an innovative marketing hack for growing his investing podcast called Money for the Rest of Us. He put the names of other popular finance podcasts in his metadata, and Apple’s unsophisticated search algorithm would surface his show whenever people were searching for his competitors.   By the time Apple eventually eliminated that functionality, Money for the Rest of Us had built up a loyal audience that’s since downloaded the show over 20 million times. His audience is so loyal, in fact, that it sustains a high-priced membership community that charges $450 a year and generates well into the six figures in revenue.   In a recent interview, David walked me through how he developed his investing expertise, what he offers to paying members, and why he launched his own premium investing app.  

My newsletter: https://simonowens.substack.com/   In 2017, Ben Cohen was living the dream. His politics news site The Daily Banter was generating over 6 million visits a month and enough advertising revenue to support him and a small stable of writers. But then the floor fell out from under him virtually overnight; Facebook pivoted away from news and sent his traffic plummeting. Without traffic, his advertising revenue crumbled.   So in an act of desperation, Ben pivoted his entire business model into paid subscriptions. Doing so forced him to slow down his publishing schedule and focus on serving his core audience. Slowly but surely, he built up a new revenue base, and in the last few months he passed the threshold of 1,000 paid subscribers.   In a recent interview, Ben explained how he executed on his pivot and why he’s determined to never rely on a single large tech platform ever again.  

My newsletter: https://simonowens.substack.com/   Like a lot of journalists=turned-media–entrepreneurs, Eric Newcomer decided to launch a paid newsletter after leaving his job at Bloomberg in 2020. That model yielded 2,500 subscribers who collectively pay over $400,000 a year to access his newsletter about startups, but that’s no longer the biggest part of his business.   Today, Eric generates over $1.5 million a year from the Cerebral Valley AI Summit, a twice-a-year conference that he monetizes through a mixture of ticket sales and premium sponsorships. In a recent interview, he explained the conference’s origin story, how he attracts the right mix of startup founders and VC investors, and why he thinks he can replicate its format across multiple tech industry niches.  

My newsletter: https://simonowens.substack.com/   The last few years have been pretty good to the Kansas City Chiefs, what with its multiple Super Bowl championships and a close association with the biggest pop star in the world, but BJ Kissel remembers what it was like to be a fan of the team long before it started regularly winning games. Back in the early 2010s, he began blogging for SB Nation, and he used his success there to eventually land a job as the Kansas City Chiefs in-house reporter. In that role, he did everything from writing web articles to serving as a sidelines correspondent for live game broadcasts.   In 2021, he struck off on his own and co-founded the KC Sports Network, a group of podcasts and YouTube channels that cover Kansas City Sports. Today, puts out 10 different shows and is monetized through a mixture of local and national advertisers.   In a recent interview, BJ explained why he left his job at the Chiefs, how he convinced local businesses to sponsor his shows, where he sees new opportunities for growth.  

My newsletter: https://simonowens.substack.com/   Lon Seidman doesn’t operate the largest gadget YouTube channel in the world, but he doesn’t need to in order to run a successful media business. That’s because he remains hyper focused on reviewing non-sexy products that sell in extremely high volumes. This has allowed him to build a highly lucrative affiliate business, not only on YouTube, but also on Amazon Video.   In a recent interview, Lon explained his methodology for picking products to review, how he optimizes his affiliate links, and why he’s spending more time posting his content to decentralized platforms.