The Business of Content with Simon Owens

My newsletter: https://simonowens.substack.com/   One day in the 1990s, Alan Jay received a surprising phone call at work from Jeff Bezos’s assistant, who said the Amazon founder wanted to meet with him during an upcoming trip to the UK. That meeting would eventually lead to Amazon acquiring IMDB, the movie database Alan had co-founded.   After the acquisition, Alan didn’t rest on his laurels; over the next two decades, he went on to co-found two other media companies – one in entertainment and the other sports – both of which had their own successful exits. In a recent interview, Alan told the origin story of IMDB, walked through how he built the two other media properties, and explained why it’s much harder to launch a media business today compared to 20 years ago.  

Stuart Schuffman, the witty founder of Broke-Ass Stuart, recounts his journey from an early 2000s DIY zine to a beloved local media brand in San Francisco. He shares how he self-distributed his first guide while juggling day jobs, leading to a book deal and media recognition. The conversation dives into evolving into online content, navigating ad sales, and embracing video formats. Stuart also discusses his recent venture into local news and activism, as well as maintaining community engagement through Patreon and events.

My newsletter: https://simonowens.substack.com/   By the time Eric Coffie launched his YouTube channel in 2016, he was already one of the most successful federal government contractors in the US and employed an entire team that specialized in erecting steel buildings. The YouTube channel came out of his frustration of having to repeat the same advice over and over again to those wanting to break into the industry; he figured he could just record some video explainers and send them to people.   But the success of the channel led to him expanding into podcasts, and then before he knew it Eric was operating an entire media company that spanned across video, podcasts, online courses, coaching, events, and even a paid community.   In a recent interview, Eric explained how he found an audience by going extremely niche and why he wants to shut down most of his media revenue streams so he can regrow his contracting business.  

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.

In this vibrant discussion, Eli Woolery, a Stanford lecturer and co-host of the Design Better podcast, shares insights into transforming their show from an InVision initiative to an independent venture. He elaborates on the challenges of audience engagement and monetization, and the complexities of balancing valuable content with marketing goals. Eli also explores their evolving subscription models and innovative distribution strategies, shedding light on the future of live podcasts and potential collaborations in the design community.

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.