The Business of Content with Simon Owens

Sign up at https://cex.events/ and use coupon code "Simon" David Kushner had the kind of mainstream success that most writers dream of. His writing regularly appeared in glossy print magazines like Wired and Rolling Stone. Several of his books became national bestsellers. And his work has even been adapted into multiple TV shows and movies.    But in 2021, David decided to bypass legacy media entirely and start publishing his work to a Substack newsletter. What drove him to do this? In our discussion, David explained how the changing norms over IP rights and his own desire to experiment with serialized storytelling motivated him to make the move.

Sign up at https://cex.events/ and use coupon code "Simon"   When Patrick Trousdale launched his newsletter The Daily Upside in 2019, he didn’t have much of a personal brand to build from. In fact, even today, his personal Twitter account has fewer than 300 followers.   What he did have was several years of experience in finance and the willingness to grind out the newsletter each day, even when it didn’t have much of a following. That kind of persistence netted him his first few hundred followers, and it also helped him get his foot in the door so he could pitch The Motley Fool, a popular finance website, on a content partnership.   That partnership paid off in a big way, and The Daily Upside quickly grew by tens of thousands of signups. Today, the newsletter has over 300,000 subscribers and has sold out its ad inventory for months in advance.   In our interview, Patrick walked me through his initial launch strategy, his business model, and how he convinced editors at The Motley Fool to take a chance on a partnership with an unknown entity.

Sign up at https://cex.events/ and use coupon code "Simon"   When Adam White graduated from the University of Miami in 2017, he had every intention of getting a job in sports administration. In fact, he went through several rounds of interviews at a major organization and was sure he’d get an offer.   But the job never actually materialized, and instead of applying to more open positions, Adam decided to double down on Front Office Sports, a website he had founded during his freshman year in college. For the next year or so, he worked part-time jobs while also spending his mornings, nights, and weekends interviewing top executives at the largest sports franchises all around the world.   His bet paid off in a big way. Not only did he manage to secure angel investment, but the site also started to attract major sponsors. Today, Front Office Sports is a powerhouse in the B2B sports media space, and it’s using its momentum to expand into new verticals.   In my interview with Adam, he explained to me what sparked his initial idea, how he became a better interviewer, and why he’d rather embrace slow growth than accept large VC investment.

Get your tickets at https://cex.events/ and use coupon code "Simon"   Pat Walls’s most successful startup to date was born in the wake of a previous failed startup. Back in 2016 he and a couple other co-founders had been operating a B2B SaaS platform, but after it struggled to gain traction, they were forced to shut it down.   But Pat never lost the entrepreneurship itch, and in 2017 he started interviewing other startup founders on the phone and converting those interviews into case studies for a website called Starter Story. After a few of those case studies blew up on Reddit, Pat knew he was onto something, so he started publishing them with more frequency.   Flash forward a few years, and Starter Story now attracts over a million visitors a month, many from Google Searches. It also generates half a million dollars in annual revenue through a mixture of advertising, membership, and affiliate marketing.

Sign up for my course: http://contentbusiness.org/ When it comes to coverage of the tech sector, few publications can match the journalistic heft of The Information. Launched by former Wall Street Journal reporter Jessica Lessin in 2013, The Information quickly became an industry powerhouse, attracting some of the world’s best journalists who broke many of the biggest scoops over the past decade. If there’s a major story in tech, chances are that an Information reporter is chasing it.    So it wasn’t exactly a surprise when, in January 2021, the publication put out a job ad for a Creator Economy reporter. With an estimated $100 billion in annual revenue, the Creator Economy has not only launched the careers for thousands of creators, but it’s also become the core focus for many of the world’s largest tech platforms. Venture capitalists are now pouring billions of dollars into Creator Economy startups, and creators themselves are upending entire industries that include beauty, commerce, health, and entertainment.   In April 2021, The Information announced that it had hired Kaya Yurieff, a former CNN tech reporter, to helm its Creator Economy coverage, and she’s since launched a daily newsletter that, in addition to publishing regular feature stories, also rounds up deals, trends, and product launches.    Given the relative newness of the Creator Economy beat, I wanted to get a better idea of how Yurieff shapes her coverage. In a recent interview, she walked me through her weekly routine for news gathering, her methods for assessing startup founders’ claims, and where she thinks the industry is heading in the near future. 

After graduating from Harvard Law School in the early 2000s, Maria Brito was poised to have a successful career as a corporate lawyer. There was just one catch: she hated practicing corporate law. Instead, her true passion was art. Throughout the early 2000s she started visiting New York galleries and even started to recommend pieces for purchase to her friends. Eventually, it dawned on her that high net worth individuals would pay her for the recommendations that she was giving out for free. In 2009, Maria quit her law firm job and launched a new career as an art buying consultant. She also invested a significant portion of her time into creating online content, first with a blog and then later on social media. She eventually grew her audience to over 200,000 followers across Instagram, Facebook, Twitter, and email, and she’s leveraged this audience to sign book deals, run brand sponsorship campaigns, and bring in dozens of wealthy clients that include Gwyneth Paltrow and Sean "Diddy" Combs. In a recent interview, she explained to me her content creation process, her philosophy on Instagram sponsorship deals, and why so many high net worth individuals trust her to buy art for their collections, often after seeing only a static iPhone photo of the piece she’s recommending for purchase.

As a CBS reporter in Los Angeles, Erica Mandy had a thriving career ahead of her in TV news. But in 2017 she quit her job and launched her own daily news podcast. It’s called The Newsworthy, and every morning it gives listeners a 12-minute rundown of the most important headlines. It also delivers weekend longform interviews with newsmakers. After four years in operation, it now generates over 800,000 downloads per month and has a growing team. I spoke to Erica about why she made the jump from TV to podcasts, how she found her audience, and whether the daily news podcast space is becoming saturated.

The Guardian recently announced it reached 1 million paying digital subscribers. What's most incredible about the accomplishment is that the newspaper reached that number without using a paywall. Does that mean that paywalls are overrated? I sat down with Ben Cohen, editor of The Banter, to discuss whether publishers should keep all their content free.

In 2014, Owen Walker faced a predicament. He was a sports scientist at a professional football club, and his manager asked him if they should buy expensive wearable technology that would help with the team’s training. Walker turned to the internet to research whether this kind of technology was effective, but he found there wasn’t much good sports science information online. That realization eventually led to the launch of Science for Sport, one of the leading information hubs that translates peer-reviewed sports science for a lay audience. The outlet has been embraced as a resource by pro and college teams, and Owen recently sold it to one of the world’s largest sports technology companies.  In our interview, Owen walked me through how he built the site’s audience, his monetization strategies, and why he never focused on building his own personal brand.

Over the past few years, dozens of star journalists at mainstream media outlets announced that they were quitting their jobs to launch their own ventures, usually on platforms like Substack. As a result, some have drastically increased their income, sometimes into the seven figures.  As more and more writers defected, I and others wondered how legacy media outlets would respond. Would they adapt their business models so that their writers could capture more of the value that they generate? Last week, The Atlantic announced that it's partnering with about a dozen writers to author standalone newsletters for the magazine. Though the partnership details are somewhat vague, they could provide a framework for how media outlets will compete with platforms like Substack moving forward. To discuss these moves, I sat down with communications consultant Jonathan Rick. We dove into The Atlantic's newsletter strategy and discussed whether it's effective enough to lure independent journalists back into the warm embrace of legacy media.