The Business of Content with Simon Owens

Kelsey Ogletree, freelance travel writer and founder of Pitchcraft, discusses how she built a membership community for PR pros. Topics include adapting to the travel industry during the pandemic, the concept of press trips, selling out paid workshops, and creating a membership community for PR pros and freelance writers.

Ash Read didn’t launch a review website about household products because of some lifelong interest in home decor; instead, his interest came about simply because he was moving into a new house and needed to furnish it.   While it was easy to search for products listed on retailers like Amazon and Walmart, he realized that there wasn’t a good directory for the direct-to-consumer goods that are sold directly through a company’s website. So he created a database of direct-to-consumer companies and published it to the web. The audience feedback was so strong that he decided to build out an entire website dedicated to covering and reviewing D2C home products.   Ash launched Living Cozy in 2020, and over the next few years he scaled the site to over 350,000 monthly pageviews. What started out as simple product curation soon led to an in-depth review process and him hiring a network of freelance writers to review items like sofas and beds.    How did Ash manage to break into such a saturated market category that was already dominated by much larger websites? In an interview, we talked about his introduction to direct-to-consumer products, his clever use of search keywords, and how he coordinated the shipment of large pieces of furniture to reviewers all over the world.  

For most of his career as professional ultra marathoner, Dylan Bowman didn’t have much of an online presence, but in 2019, he suddenly found himself with a lot of time on his hands after he broke his left ankle and had to take a year off from racing. That year, he launched a podcast where he interviewed his fellow pro runners, and it pretty quickly became a huge hit.   It didn’t take long for Bowman to realize that the podcast provided a huge opportunity for his post-racing career, so in late 2020 he and a co-founder launched Free Trail, a media outlet that operates a podcast network, a YouTube channel, and even its own ultramarathon races.   In an interview, Dylan walked me through how he built the company, his monetization strategy, and why it represents the future of sports media.  

In 2011, Rafat Ali launched Skift, a B2B publisher that covers the travel industry. At first, Skift was mainly monetized with advertising, but Rafat quickly realized that scaling a B2B niche outlet required a diverse set of business models that included memberships, research, events, and advertising. He also acquired multiple other media outlets that operated in adjacent industries. In an interview, Rafat walked us through this journey and explained how he managed to simplify the company’s value proposition while embracing the complexity of multiple revenue models. We also spoke to Walter Frick, who ran the membership program for business publisher Quartz for nearly three years. He answered our questions about what motivates readers to convert into subscribers and what he learned when Quartz made the radical decision to completely remove its website paywall.

Patrick Walls, founder of Starter Story, discusses his transition from selling advertising to offering one-time payments for permanent access to his content archives, helping him achieve $1.5 million in annual revenue. Bradley Hope shares insights on funding and adapting narrative projects across multiple formats. The podcast explores Starter Story's evolution, revenue diversification, and the success of mid-roll ads. It also delves into the costs of producing a narrative podcast and the challenges of optioning intellectual property in the film industry.

It used to be if you wanted to break into broadcast media you first had to start small – by getting a job as a correspondent at a local news station and then working your way up to bigger and bigger markets.   That’s the career trajectory that Casey Keirnan followed. He started out covering high school sports in small towns and then eventually landed a job at CBS Interactive, which was trying to create an ESPN competitor for OTT streaming. But after only two years on the job, Casey’s contract wasn’t renewed, and he feared he would have to go back to local news.   But then he launched A.M. Hoops, an NBA-focused YouTube channel that ended up being so successful that he replaced his previous salary within a few months. Today, it boasts over 400,000 subscribers and 264 million channel views.   In our interview, Casey told me about his slow climb in local news, why he struggled at his CBS job, and what inspired him to strike off on his own to start a YouTube channel.  

If you run any sufficiently large organization, one of the biggest threats to your business is runaway costs. The largest companies can use upwards of thousands of suppliers for everything ranging from software technology to building materials, and how much you spend on all these suppliers can be the determining factor over whether you’re profitable or unprofitable.   That’s why most large businesses employ procurement specialists – people whose job it is to oversee and negotiate services with outside companies. It’s not the sexiest job in the world, but it’s incredibly important, and it’s the reason why the procurement services industry is worth $6 billion.   Philip Ideson runs a media company that covers this massive industry. After spending 15 years as a procurement specialist himself, he launched The Art of Procurement, a news and information resource that caters to procurement specialists. Over the past seven years, he’s built it into a business that’s monetized through live events, sponsorships, and consulting.   In our interview, he talked about his motivation to launch the company, how he built his audience, and why he struggled so long to find a viable business model.  

There’s a common criticism lodged against Substack that its model of paid subscriptions could never support original journalism, and instead it only caters to the kind of opinion journalism that can be churned out at a high rate.   Eric Newcomer is proving this criticism wrong. After six years spent reporting at outlets like The Information and Bloomberg, he struck off on his own and launched a newsletter that covers startups and venture capital. Within months of his launch, he broke several major stories about top VC firms like Andreessen Horowitz and Sequoia.   In our interview, Eric talked about his motivation to leave his job in traditional media, his monetization strategy, and how he manages to break major stories at such a consistent rate.  

When Jay Shabat launched his newsletter in 2004, he had absolutely no experience in journalism or in operating a media company. This was also long before the era when it became easy to distribute paid newsletters. But what Jay did have was a passionate fascination with the airline industry, and he leveraged that passion to build a loyal readership.   In our interview, we discussed how he found readers in a pre-social media age, his pricing strategy, and why he decided to sell the company in 2018.  

Today, Android is the number one operating system for smartphones, but when Google launched the product in 2008, the iPhone already had a huge head start. Most consumers didn’t know it existed, and even the tech press didn’t take it super seriously.   But JR Raphael was an early fan. A freelance tech journalist who wrote for publications like Fast Company and The Verge, JR pitched his editors at Computerworld on a regular column about Android,  and though they were skeptical at first, they gave him the green light.   As Android grew into a major mobile operating system and eventually overtook the iPhone, JR became one of the leading authorities on the product. In 2018, he launched Android Intelligence, a supplementary newsletter that mostly linked to his column and other news items, but as it picked up steam, he began to introduce more and more monetization features. By 2023, Android Intelligence was generating the majority of his annual income.   In our interview, JR explained to me why he was such an early fan of Android, what motivated him to launch the newsletter, and how he turned it into a thriving business.