The Business of Content

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.

My newsletter: https://simonowens.substack.com/   Book publicity is a mixed bag these days. On the one hand, it’s never been easier for an author to form a direct relationship with their audience with tools like Substack and TikTok. On the other hand, more books are published each year than ever before, which means competition is fierce. Most newspapers have laid off most of their book critics, but at the same time there’s an ever expanding ecosystem of podcasts that are eager to have on book authors for longform interviews.   Probably nobody is more knowledgeable about marketing books in the modern age than Kathleen Schmidt. She spent nearly 20 years working for almost every major book publishing company, and she now runs her own firm that specializes in book marketing. She also writes Publishing Confidential, her insider account of how the book industry actually functions.   In a recent interview, Kathleen walked through nearly every aspect of selling books, from choosing the right cover to courting influencers to advertising on Amazon.

My newsletter: https://simonowens.substack.com/   When people sign up for the Alts.co newsletter, they’re looking to read its deep dives into alternative investments like art, baseball cards, and rare books. But the most serious investors in its audience want access to actual deal flow, and to gain that access they sign up for Altea, a high-priced membership community that actually vets potential deals and allows them to invest. Not only does Alts.co generate revenue through the annual membership, but it also charges for management fees and carried interest. In essence, Alts.co is a media company that monetizes via an investment firm.   In a recent interview, co-founder Stefan von Imhof explained why his company settled on this model, how it sources deals, and why he eventually wants to stop selling sponsorships within the newsletter.

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.

My newsletter: https://simonowens.substack.com/   Most people are familiar with newswires like the Associated Press and Reuters, but a much newer upstart called Stacker has devised a new business model for syndicating content. Rather than charging a fee for its articles, it instead gives away its data journalism to any publisher that wants it. It then charges brands a fee to create and distribute sponsored content across the thousands of media outlets that subscribe to its service.   In a recent interview, co-founder Noah Greenberg explained how Stacker works with publishers, its process for creating sponsored content, and why he has no interest in driving an audience to Stacker’s owned and operated website.

My Substack: https://simonowens.substack.com/   Mignon Fogarty isn’t just one of the world’s most popular podcasters, she’s also an incredibly innovative media entrepreneur. She launched her Grammar Girl podcast 18 years ago, and the success of that propelled her book onto the New York Times bestseller list. She also founded Quick & Dirty Tips, a media network she now runs in partnership with Macmillan Publishers.   To round out her media business even more, she’s launched around seven courses, all geared toward being a better communicator and writer. Thousands of customers have taken them, and they’ve opened her up to an entirely new customer base for her content.   In a recent interview, Mignon explained how she entered the courses market, what goes into putting together a course, and why she decided to partner with powerful distributors like LinkedIn Learning rather than create the courses by herself.

My newsletter: https://simonowens.substack.com/   Most companies buy advertising to drive sales of their products, but Andrew Curtin’s first sponsor mostly bought out of pity. It was May 2022 and he had just launched Construction Wave, a B2B outlet that covers the UK’s construction industry. He had absolutely no audience, but a major crane manufacturing company bought a $10,000 sponsorship anyway.   That $10,000 allowed him to hire his first editor, and over the next two years they built Construction Wave up into one of the leading publications in its sector. Its website is mainly monetized through high-priced sponsorships, and this year it hosted its first conference geared toward construction CFOs.   In an interview, Andrew explained how he got interested in the sector, where he found his initial readers, and why he thinks there’s an opportunity to launch a subscription data product for his industry.

My newsletter: https://simonowens.substack.com/   Like a lot of journalists in the mid-2000s, Tim Burrowes grew frustrated with his employer’s print mentality and its tendency to treat online publishing as an afterthought. At the time, he worked for an Australian trade magazine that covered that country’s media industry.   So in 2008, he and two co-founders decided to launch Mumbrella, a competing blog that published upwards of 15 times a day. Its gossipy comments section quickly attracted an audience of bored office workers, and within a few years it was hosting multiple industry events that collectively generated millions of dollars.   In a recent interview, Tim explained how Mumbrella made such a big splash so quickly, why he and his co-founders decided to sell it, and what he’s doing differently with his newest media startup.

My newsletter: https://simonowens.substack.com/   When Alex Halperin launched WeedWeek in 2015, he was entering an industry that had nothing but growth ahead of it. But what he didn’t expect was that the fragmented legalization across states meant that it’d be difficult to build a national audience. So a few years ago he pivoted to just covering California’s weed industry, and WeedWeek has since built a robust business monetized through both sponsorships and subscriptions.   In our interview, Alex walked me through what got him interested in the topic, why he built a customer publishing platform, and how he recently decided to team up with the LA Times on an investigative series.

My newsletter: https://simonowens.substack.com/   One of the great things about being a college journalism major today is that it’s incredibly easy for professors to build their own news sites and allow students to experience every aspect of the publishing process. Not that long ago, journalism students had few avenues for publication outside their college newspaper.   Lydia Chavez took advantage of this dynamic while teaching at UC Berkeley. In 2008, she and her colleagues launched Mission Local, a local news blog that covered San Francisco’s Mission District. It quickly gained traction within the community, and in 2014 Lydia spun it out into its own independent news organization. Today, it’s fully sustained by a mix of large and small donors.   In our interview, Lydia walked me through how she incorporated the site into her journalism curriculum, why she spun it out from the university, and whether she thinks Mission Local’s model can be replicated across the US.

My newsletter: https://simonowens.substack.com/   When Patrick O’Shaughnessy launched his podcast Invest Like the Best in 2016, he had no intention of building it into a media company. He just wanted to use it to interview the world’s best investing minds so that he could deepen his own understanding of the industry. But the show proved to be a huge hit, attracting some of the biggest names in finance. By 2020, he and a few co-founders launched Colossus, an investing-focused podcast network that now produces more than a half dozen shows across various finance niches.   In an interview, Colossus CEO Matt Reustle walked me through the vision behind the network, how it develops and promotes new shows, and why the company hasn’t yet launched video versions of its podcasts.

My newsletter: https://simonowens.substack.com/   What does a professional travel photographer do when all international flights are shut down due to a global pandemic? That’s a question Gary Arndt found himself asking in the early months of 2020. By that point, he had built up millions of social media followers and an entire career from snapping photos in exotic locales, and within a matter of weeks his income streams had completely dried up.   Luckily, he had already been batting around the idea for a podcast that didn’t require any travel. In July 2020, he started producing seven episodes a week of Everything Everywhere, an educational show about a diverse range of topics, and it immediately took off. Today, it generates 1.5 million monthly downloads and pulls in much more advertising income than Gary ever made as a travel photographer.   In our interview, Gary walked through how he found his audience, where he gets his ideas for new episodes, and why he weaned himself off the social media platforms that once delivered him huge reach.

My newsletter: https://simonowens.substack.com/   When Jared Newman launched his Cord Cutter Weekly newsletter back in 2016, the streaming TV market was much smaller than it is today, with most TV networks either not having their own streaming app or requiring a cable subscription to access it. But as it turned out, he timed his launch perfectly, as it was only a matter of years before virtually every Hollywood studio pivoted to streaming. Today, his newsletters has over 32,000 subscribers, and a spinoff newsletter that gives tech advice has also grown to 1,200 paying members.   In our interview, we discussed his motivation for launching the newsletter, why his editor let him promote it at the end of his columns, and whether he ever wants to leave his freelance career entirely to just focus on growing his two newsletters.