The Business of Content with Simon Owens

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In some ways, Rahul Pandey’s career as a YouTuber has been pretty typical. After several years working at large tech companies like Pinterest and Facebook, he started uploading videos that gave career advice to other engineers who are trying to break into the industry. Then once he built a significant following, he left his full-time job in 2022 to focus on this type of educational content full-time.   But where he differs from other YouTubers is his choice of business model. Rather than going the typical route of securing brand sponsorships, he instead co-founded Taro, an online community platform where engineers can collaborate and share career advice. The company monetizes through a monthly subscription, and to date it’s mentored thousands of engineers through its community.   In our interview, we discussed how Rahul built his channel, why he launched a tech platform, and what his future on YouTube now looks like.   

When it comes to creating content for online audiences, few people are more experienced than Mark Talkington. He was one of the original editors of ESPN.com and then later spent 20 years as the news editor for MSN.com, the massive web portal owned by Microsoft.   But starting at the beginning of the pandemic, Mark began writing for a much smaller readership: the residents of Palm Springs, California. Taking advantage of the fact that most government meetings were now being broadcast online, he spent his nights and weekends writing a daily newsletter dedicated to keeping citizens informed about their local community.   The newsletter was called The Palm Springs Post, and it was an instant hit, growing to 13,000 subscribers in a little over a year. By 2022 he was able to hire another journalist and launch a second newsletter covering a nearby region. Earlier this year, he left his job at Microsoft to focus full-time on growing his company.   In our interview, Mark talked about how he produced the newsletter during his free time, his business model, and what other local news entrepreneurs can learn from his approach.  

Of all the media revenue models, subscriptions can be the most tricky to execute well. There are just so many variables at play that impact a publisher’s ability to succeed. You have to figure out what to place both in front of and beyond your paywall, how to price your subscription, how to convert free readers into paid subscribers, and how to reduce your churn.   And that’s just scratching the surface. Getting one of these variables wrong can mean all the difference in determining whether a subscription business succeeds or fails.    That’s why I convened a panel of experts to dive into the nuances of subscription economics and identify the strategies that will increase your chances for success. They included:   Peter Ericson, CEO of the Leaky Paywall subscription platform, which helps publishers seamlessly build their audience and grow paid subscriptions Michael Donoghue, CEO of Subtext, a platform that allows publishers to send text messages to their paid subscribers Jane Friedman, founder of The Hot Sheet, the most successful paid newsletter that covers the book industry Randy Cassingham, founder of This is True, possibly the world’s first paid email newsletter  

The local news industry has seen better days. The last 15 years or so have been pockmarked with mass layoffs, shuttered newspapers, and growing news deserts.   But there have been bright spots in the local news landscape … lean media startups that aim to fill the gaps left by their legacy newspaper counterparts. One such startup is called City Cast. Founded by former Slate editor David Plotz, City Cast has a unique model in which it simultaneously launches both a daily newsletter and podcast in each city it covers.    For this episode, I spoke to Bryan Vance, City Cast’s director of newsletters. We discussed the company’s playbook for launching in new cities, how it creates synergies between its podcasts and newsletters, and its approach to gathering local news  

There’s this common saying you hear in academia: those who can’t do, teach. But that axiom certainly doesn’t apply to Jeremy Caplan. Not only did he have a decade of reporting experience before he started teaching entrepreneurial journalism at the City University of New York, but in 2020 he launched his own entrepreneurial media outlet: Wonder Tools.   Wonder Tools is a free weekly newsletter that highlights the most useful websites and apps to make your life and career easier. Since launching on Substack, it’s grown to over 23,000 subscribers and it’s generated a million visits in the last year.   In my interview with Jeremy, we talked about his journalism career, why he went into teaching, and what compelled him to launch his own media outlet.  

It’s not very easy to find online coverage of the gun industry that isn’t hyper polarized. The issue is dominated by a mix of NRA members and gun control activists, and even the traditional media does little more than play referee between these two sides.   When Stephen Gutowski launched The Reload in 2021, his aim was to cut through this noise. Stephen had spent several years covering the issue for The Washington Free Beacon, and despite his background in conservative media, his work has been widely praised by both centrist and left-of-center journalists. In 2022, CNN hired him to serve as an on-air analyst around gun policy issues.   In my conversation with Stephen, we talked about why he struck off on his own, how he monetized his newsletter, and what role his cable news career plays in building his audience.  

While paid subscription models have been all the rage for the last decade, more and more creators are turning to online courses as a way to monetize their audiences. Their evergreen nature makes them ideal for generating passive income, and many creators have succeeded at selling them at relatively high price points.   But what’s the best way to develop a course that your audience will actually want? And how do you market it to that audience?    I recently convened a panel of professional course creators to answer these questions. We talked about everything including identifying course topics, setting prices, and choosing the best platform to host your course.  

Let’s say you have a pile of money you’re sitting on and you want to invest it. If you decide to invest it in stocks, then it’s incredibly easy to track the value of your investment on a minute by minute basis. But what if you want to invest in a less-regulated asset class like, say baseball cards or art? How do you even begin to assess the price of these assets, both before and after you’ve purchased them?   You’d probably turn to a guy like Stefan von Imhof. For the past few years, he and a co-founder have been running a newsletter focused on alternative investments. Its weekly installments go deep on various investment categories ranging from limited edition books to water rights, and it now reaches over 85,000 subscribers.   The newsletter is not only monetized through the traditional models, but it also launched a fund for accredited investors, and Stefan’s team has deployed millions of dollars across several asset classes.   In my interview with Stefan, we talked about how he got interested in alternative investments, the steps to launching a fund, and his strategy for acquiring other newsletters.

Historically, foreign correspondents haven’t been the type of journalists who break major news stories in the countries they cover. That’s because they’re typically not as well sourced as the local reporters who grew up in a particular region and have an intimate knowledge of its issues.   But what would happen if you could take the work of local reporters and translate it for English-speaking readers? That’s the idea behind Worldcrunch, a media outlet that was founded in 2011. Rather than creating all of its own content, it syndicates articles from publications all around the world and then pays translators to adapt those articles for a Western audience.   In a recent interview, founder Jeff Israely talked about his years of work as a foreign correspondent for Time Magazine and how that fueled the idea for Worldcrunch. He also discussed the publication’s evolving business model as it moved from syndication to advertising and subscriptions.