Claim OwnershipThe Business of Content with Simon Owens
Subscribed: 105Played: 4,170
Subscribe
© Simon Owens 2025
Description
The show about how publishers create, distribute, and monetize their digital content.
249 Episodes
Reverse
My newsletter: https://simonowens.substack.com/ The Coppell Chronicle isn’t your average Substack newsletter. For one, the headlines are incredibly boring. Secondly, there’s really no free version of it, since every issue that’s sent out includes a paywall. But perhaps the most remarkable thing about it is that it’s managed to convert upwards of 40% of its email list into paid subscribers, which is a conversion rate at least 10 times higher than the average Substack newsletter. What’s more, its owner Dan Koller achieved all this while maintaining his full time job. In a recent interview, Dan explained how he launched the newsletter, why it took off in his Dallas suburb, and whether he thinks other wannabe local news entrepreneurs could copy his model.
My newsletter: https://simonowens.substack.com/ If you ask Dave Anderson what he does for a living, he’ll probably tell you he’s retired, but that’s not entirely true. While he did leave his last full-time job at Amazon back in 2020, he still writes a weekly newsletter on Substack about tech leadership. And even though he only works on the newsletter part time, it currently has over 2,000 paid subscribers. It turns out a lot of people want to tap into his insights gleaned from 20 years working in the tech industry, including over 10 at Amazon. In a recent interview, Dave discussed the newsletter’s origin story, how it found its audience, and why he doesn’t have any ambitions to scale it into a larger media company.
My newsletter: https://simonowens.substack.com/ Andrew Fogliato never set out to be a marketing consultant. He was simply trying to succeed as a real estate agent and began creating local online content to promote his listings. His colleagues at RE/MAX quickly noticed that his marketing savvy gave him an edge, and soon he was training other agents across Canada. Eventually, he left RE/MAX to launch his own marketing agency, where he built a strong business helping agents run Facebook ads. In 2022, Andrew saw an even bigger opportunity. He purchased Real Estate Magazine, Canada’s largest industry trade publication, and immediately began expanding its online presence. In a recent interview, he discussed why he bought the magazine, his approach to monetization, and why he isn’t in a hurry to expand into the U.S. market.
My newsletter: https://simonowens.substack.com/ SailGP is only a little over five years old, and yet the competitive sailing league has already built out a substantial fan base all across the world. Not only are its competitions broadcast on linear TV channels, it also produces an impressive amount of content that includes YouTube videos, social media clips, and podcasts. In 2022, it hired Melissa Lawton, a longtime sports broadcast producer, to run its content operations, and she’s invested heavily in everything from live streaming to highly-produced docuseries. In a recent interview, Melissa explained how SailGP’s media operations fit within its larger business and walked through her team’s approach to producing both shortform and longform content.
My newsletter: https://simonowens.substack.com/ When Eli Woolery and Aarron Walter launched the Design Better podcast, they did it on behalf of InVision, a tech platform used by designers and other creatives. Aaron was the head of content at the company, and the goal of the podcast was to educate the designer community while also raising awareness of the InVision brand. But when InVision decided to wind down its content operations, Eli and Aarron negotiated to take over Design Better, and now it’s a thriving standalone business. In a recent interview, Eli talked through everything from the evolving format of the show to how it became an independent media business to its current monetization models.
My newsletter: https://simonowens.substack.com/ When Kevin Raposo launched KnowTechie in 2014, he had no idea it would grow into a thriving tech news outlet – he just wanted journalists to answer his emails. He was working as a PR consultant and figured reporters would be more receptive to his pitches if they considered him to be one of their peers. But after three years of running the site, its audience blew up, and Kevin was able to hire several writers to expand its coverage. And while the rise of generative AI has eaten into its traffic, KnowTechie continues to drive meaningful revenue. In a recent interview, Kevin walked me through his accidental entry into content marketing, his strategy for growing KnowTechie’s audience, and how running the site impacts his day job as a tech PR consultant.
My newsletter: https://simonowens.substack.com/ By the time Amy Wilson and Margaret Ables came together to launch a parenting podcast in 2016, both had already achieved some mainstream success in traditional Hollywood. Amy landed multiple roles in TV sitcoms and Margaret had worked for several years as a senior writer at Nickelodeon. They teamed up on the podcast, which is called What Fresh Hell, because it offered them more creative freedom and ownership over their work. Within years, advertisers were beating down their door to reach their enormous audience, which mostly consists of moms. In 2022, they leveraged that success to launch Adalyst Media, a podcast network that sells ads for other shows targeting female audiences. In a recent interview, Amy walked me through why she left traditional Hollywood, their decision to launch a network, and how she thinks the podcast industry will evolve in the coming years.
My newsletter: https://simonowens.substack.com/ Spencer Macnaughton doesn’t believe there’s a lack of LGBTQ-focused journalism in the mainstream media; as a former producer for both 60 Minutes and the Wall Street Journal, he saw a willingness from these outlets to cover anti gay and trans hate movements. He launched Uncloseted Media last year, though, because he thinks there’s a need for more concentrated, investigative reporting on this type of discrimination, and he convinced several wealthy donors to contribute hundreds of thousands of dollars to help him get it off the ground. Today, it publishes up to two investigative articles per week and has been syndicated by some of the world’s largest media outlets. In a recent interview, Spencer walked me through how he pitched these donors, why he went the non-profit route, and how he works with other news outlets to amplify his team’s reporting.
My newsletter: https://simonowens.substack.com/ You’ve probably seen headlines by now declaring 2024 to be the podcast election. It certainly did seem like a breaking out point that established podcasts as important messaging vehicles for any future presidential candidates. But back in 2015, podcasts had far less clout, and most of the political shows that did gain traction were produced in DC and New York. That didn’t stop Sarah Stewart Holland and Beth Silvers, two Kentuckians with very little media experience, from launching Pantsuit Politics, a show that quickly amassed an audience of listeners that were spread out all across the US. They eventually built out a well diversified business that includes advertising, paid subscriptions, and live events, and they’re now trying to expand their reach on YouTube. In a recent interview, Sarah and Beth explained how they came up with the idea for the show, where they found their audience, and why they don’t host their events in large cities.
My newsletter: https://simonowens.substack.com/ Jonathan Skogmo has been working with user generated content since before the term “user generated content” even existed. Back in the 2000s, he moved to Hollywood and worked for what were called “clip shows,” where viewers would physically mail in funny home videos to have them compete for cash prizes. As it turned out, Jonathan’s entry into the industry coincided almost perfectly with the launch of YouTube. He was eventually able to leverage his skills to find viral clips on YouTube and license them to the media companies and brands that wanted to use them. His company Jukin Media eventually paid out over $50 million in royalties and in 2021 was acquired by the company that owns Readers Digest. Now, Jonathan is building a new company focused on travel, and rather than growing it from scratch he’s acquired several existing media brands. In a recent interview, he walked me through his acquisition strategy and explained why physical travel guidebooks still have currency in an era where influencers seem to have captured the market.
My newsletter: https://simonowens.substack.com/ If you work in the live music business, there’s a decent chance you know of Josh Weidling, even though you probably wouldn’t recognize his face. That’s because he’s almost always been behind the camera as he interviewed literally thousands of musicians touring through the midwest. Josh launched his YouTube channel Digital Tour Bus in 2009, and over the next 15 years he dutifully uploaded upwards of five fresh interviews a week with musicians who walked the viewer through their tour bus and explained how they chose their musical instruments and gear. In a recent interview, Josh dove into the origin story of the YouTube channel and explained how he turned it into a business. He also discussed why he decided to keep his day job rather than go all in on the franchise.
My newsletter: https://simonowens.substack.com/ Of all the media outlets to have launched in the last decade, Morning Brew has had one of the most impressive growth trajectories. Not only did it build its main newsletter to millions of subscribers, but it also spun off multiple B2B niche verticals and has had enormous success on platforms like YouTube and TikTok. So it’s not surprising that when three of its early employees left to launch their own media company, there were plenty of high profile creators eager to work with them. Under the banner of Smooth Media Creative Holdings, these alums have built out an influencer marketing agency and also their own niche outlets. In a recent interview, co-founder Josh Kaplan delved deeper into Smooth Media’s strategy, explained how it works with big YouTubers, and discussed why the company decided to acquire a 30-year-old B2B media brand.
My newsletter: https://simonowens.substack.com/ Food content is now a major staple on YouTube, but when baker Gemma Stafford launched her channel in 2014 there were hardly any professional chefs on the platform. This early mover advantage allowed her and her husband Kevin Kurtz to build up a massive audience that used Gemma’s tutorials in their own baking efforts. Then a few years ago they teamed up with media veteran Ronald Pruett, Jr. to launch the Bold Baking Network, a streaming platform that syndicates content from hundreds of baking creators all across the world. In a recent interview, Kevin and Ron walked through the company’s origin story, how they monetized Gemma’s videos, and why they decided to expand beyond YouTube and build their own platform.
My newsletter: https://simonowens.substack.com/ The podcast company Sonoro launched in 2020 with a relatively simple thesis: that there were very few media companies geared toward the 62 million latinos within the US. Over the next four years, it built out a stable of dozens of podcasts across several formats ranging from serialized nonfiction to personality-led chat shows. In addition to the standard podcast monetization models, it also sought to further capitalize its IP by selling adaptations to Hollywood studios and developing its own merch lines. Today, the network generates over 100 million monthly downloads and works with some of the world’s biggest latino creators. In a recent interview co-founder Joshua Weinstein explained how the company partners with talent and walked through all the ways it’s monetizing its IP.
My newsletter: https://simonowens.substack.com/ When the media covers business acquisitions, it’s usually only for huge deals involving VC-backed companies. Coverage of mergers for small, bootstrapped businesses is almost nonexistent. That’s where They Got Acquired comes in. Launched in 2021, it focuses on acquisitions in the $100,000 to $50 million range. Recently, it put out a detailed research report specifically focused on acquisitions of media outlets, which are typically sold at lower multiples than other kinds of online businesses. In an interview, founder Alexis Grant walked through the experience she had selling two of her own media outlets and explained the steps a current media entrepreneur should take to maximize the selling price for their own business.
My newsletter: https://simonowens.substack.com/ Given the tumultuous economic landscape for local news, many outlets are turning to nonprofit models because they offer increased flexibility for generating revenue. But while these outlets have been adept at attracting foundation grants and small donor memberships, they’re not doing enough to cultivate relationships with the wealthy members of their own communities, many of whom can write much larger checks than your average reader. At least that’s the thesis of Julie Rafferty. She not only has a deep background in consulting with nonprofits, but she also played an instrumental role in co-founding Brookline News, a nonprofit media outlet that operates outside of Boston. In a recent interview, Rafferty walked through how she got wealthy members of her city to fork over $100,000 before the outlet even launched, and she gave some good advice on how other nonprofit newsrooms can identify and reach out to rich people in their own communities.
My newsletter: https://simonowens.substack.com/ If you work in the media industry, you’re likely aware of The New York Times tremendous success with its gaming vertical; in fact, millions of people subscribe solely so they can play games like Wordle and Connections. But it’s not the only publisher that’s incorporated games into its business strategy. Hundreds of outlets ranging from Morning Brew to The New Yorker utilize a platform called Amuse Labs to build everything from crosswords to sudoku. In a recent interview, co-founder John Temple explained how publishers can leverage games to increase everything including time on site, repeat visits, advertising revenue, and paid subscription conversions.
My newsletter: https://simonowens.substack.com/ You’ve probably never heard of Schneps Media, but if you live in any of the five boroughs of New York, you’ve probably encountered its content. Started as a single Queens newspaper in 1985, the company gradually bought up community news outlets all across New York, and it’s since expanded into Philadelphia and even Palm Beach, Florida. It not only targets audiences by locale, but also ethnicity. And most of its news is completely free to read. How has the company continued to grow despite so many headwinds in local news? To answer this question, I spoke to CEO Josh Schneps. He told the story of how his mother launched that first Queens newspaper and explained why businesses continue to advertise with him despite having plenty of other options.
My newsletter: https://thelongstory.substack.com/ Earlier this year, China crossed a major milestone when BYD, an electric car company based in its Shaanxi province, surpassed Tesla in total sales. What’s more, most experts believe the country is only at the beginning of its EV dominance. In a recent Washington Post article titled “How China pulled ahead to become the world leader in electric vehicles,” journalist Christian Shepherd explained how the country’s centralized, top-down government prioritized every level of the supply chain, from the building materials to the manufacturing to the charging stations. In a recent interview, we discussed what decisions the country made over a decade ago to incentivize EV production, to the point where it can sell cars at nearly half the price of its non-Chinese competitors. We also explored what the US would have to do if it wants to catch up.
My newsletter: https://thelongstory.substack.com/ They walk among us, almost completely undetected. If you notice them at all, it’s because they’re pulling a discreet tin out of their pockets so they can replace the small, white pouch hidden above or beneath their molars. Yes, I’m talking about Zyn enthusiasts. Though the nicotine pouch came to our shores over a decade ago, it’s only within the last few years that its reach expanded from the boiler rooms on Wall Street to the open office cubicles in Silicon Valley. How did the product develop its obsessed fanbase? To answer that question, I turned to Carrie Battan, the author of a New Yorker piece titled “Zyn and the New Nicotine Gold Rush.” In our interview, she traced its origin as a Swedish cigarette replacement, explained why it has the potential to radically expand the nicotine-delivery industry in the US, and assessed the science as to whether nicotine is even bad for us when it’s not absorbed through the lungs.
Comments
Download from Google Play
Download from App Store
United States