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.  

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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.