The Business of Content with Simon Owens

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.  

In this engaging discussion, Kathleen Schmidt, a seasoned book marketing expert with nearly two decades of experience, shares her insights on the evolving landscape of book promotion. She highlights the crucial role of social media, especially TikTok, in connecting authors with their audiences. Kathaleen discusses effective strategies for book cover design, influencer collaborations, and the importance of navigating a crowded market. She also touches on the challenges and opportunities faced by both traditional and self-published authors in this digital age.

Stefan von Imhof, co-founder of Alts.co, dives into the fusion of media and investment. He reveals how their newsletter, focused on alternative investments like art and baseball cards, evolved into the Altea membership community, providing serious investors with vetted deal access. The discussion includes their unique monetization strategies, from membership fees to management charges, and the transition from sponsored content to direct investment opportunities. Stefan also shares insights on navigating accredited investors and the importance of personalized experiences in investment ecosystems.

My newsletter: https://simonowens.substack.com/   Eric Siu has a pretty massive audience; his YouTube channel boasts 161,000 subscribers and his two podcasts – Marketing School and Leveling Up – have generated tens of millions of downloads.    But Eric doesn’t bother with traditional media monetization models like advertising or subscriptions. Instead, he leverages his influence to drive clients to Single Grain, a marketing agency he owns. As that business grew, he was able to acquire more agencies and add to Single Grain’s capabilities, and it now works with some of the world’s largest brands.   In a recent interview, Eric explained how he met his co-host, where he found his audience, and why he chose to monetize his content with a services business.  

My newsletter: https://simonowens.substack.com/   When Keith Pepper bought a chain of print newspapers back in 2020, he received an email from a columnist at the Atlanta Journal Constitution that basically asked if he was crazy. But Keith had a plan for taking a company that generated 98% of its revenue from print advertising and converting it into a digital-first media company.   And he’s done just that. Today, Rough Draft Atlanta generates 27% of its revenue from digital ads, and it managed this feat without seeing a significant decline in print advertising. This has allowed Keith to reinvest in the business by hiring more journalists, and it’s now stronger than ever.   In a recent interview, Ketih explained how he consolidated all the newspapers under a single brand, his strategy for attracting online ads, and why he’s avoided placing his content behind a paywall.  

My newsletter: https://simonowens.substack.com/   Layoffs in the local news sector are, sadly, a regular occurrence, but the founders of Block Club Chicago decided they weren’t going down without a fight.   In November 2017, the news startup DNA Info laid off its entire staff, and it was only a few months later that three of its editors launched a Kickstarter that raised over $183,000;  they used that capital to launch Block Club Chicago, a nonprofit that seeks to put a journalist in each of the city’s neighborhoods.   Flash forward six years, and Block Club has a robust news gathering operation that’s funded by 20,000 paying subscribers, foundation support, and a growing advertising business. In a recent interview, co-founder Stephanie Lulay walked me through the site’s launch strategy, its unique approach to neighborhood-based reporting, and why she thinks Block Club’s model can be replicated all across the US.  

My newsletter: https://simonowens.substack.com/   For much of its 130-year existence, State House News operated as a standard newswire service. Its journalists covered the Massachusetts state government and it then syndicated their content to regional and national newspapers.    But in the late 90s, owner Craig Sandler realized that internet distribution would allow him to sell direct digital subscriptions and vastly expand his customer base. Today, the service charges $4,000 a year to any company or organization whose business is directly influenced by the state’s government.   In a recent interview, Craig discussed how he built the direct subscription business, why he decided to sell a majority stake in the company, and whether State House News is shielded from the whims of large tech platforms and AI chatbots.