The Business of Content with Simon Owens

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.

Before the major social platforms launch a new product, they'll often run small experiments within a subset of their users to test it out. More often than not, the first person to spot these new products is a guy named Matt Navarra, and his mini scoops have been cited in thousands of news articles over the years. Matt got his career start running the digital communications for the UK government and then later became the director of social media for The Next Web. In 2018, he struck off his own and launched his own marketing consultancy. It was that same year that he began writing Geekout, a weekly newsletter that curates emerging news and information around the marketing industry. Within a few months it amassed thousands of subscribers, and today it drives six figures in revenue, mostly through sponsorships. In my interview with Matt, we talked about where he gets his product scoops, his audience growth strategies, and how he built a six figure newsletter business as basically a side hustle.

We live in an era where every company is expected to operate as a media company and every business executive is expected to produce thought leadership content. Newsletters and blogs have become crucial mediums for establishing longterm relationships with customers, and you've probably noticed that your LinkedIn feed has been flooded with posts from CEOs and startup founders who want to share their expertise. But what happens when those CEOs don't have the time or the writing expertise needed to produce compelling content? They often turn to ghostwriters: trained journalists who are able to quickly distill executives' thoughts into shareable copy. These ghostwriters often work behind the scenes – in fact most people barely know they exist – and they can often make much more money than your average journalist. But how do you break into ghostwriting when they're effectively invisible, and what's the best way to work with clients? To answer this question, I assembled a panel of ghostwriting experts to share their experience from building their businesses.

When it comes to disruption, few industries have experienced as much upheaval over the past 20 years as the music industry. The lucrative CD era ended with the rise of Napster piracy, and the introduction of Apple's iTunes did little to stem the losses, It's only within the last decade, with the rise of streaming services like Spotify, that music revenue has begun to recover. Jay Gilbert had a frontrow seat to all of this turmoil. Working for companies like Warner Music and Universal Music Group, he got to know just about every facet of the music-making process. Then in 2015, he struck off on his own and launched a consulting business. To help raise awareness of his services, he began writing a weekly newsletter called Your Morning Coffee. What started out as an email sent out to a few hundred friends eventually grew to 15,000 readers, and it's now one of the most influential newsletters in the industry. In my interview with Jay, we talked about how the newsletter found an audience, its contribution to his consulting business, and why he doesn't want to scale it into a traditional media company.

By the time Emanuel Cinca launched his Stacked Marketer newsletter around five years ago, he already had a successful affiliate marketing business, but that business was largely dependent on the whims of other platforms like Facebook and Google. He wanted to build a product that he could monetize directly, and by that point he had grown to admire daily digest newsletters like Morning Brew and The Hustle. So Emanuel decided to niche down and launch a newsletter geared toward the marketing industry. To grow the newsletter, he leveraged his skills in paid media and marketing, and today it has over 30,000 subscribers. In 2022, it generated over half a million dollars through a mixture of paid subscriptions and sponsorships. In my interview with Emanuel, we went deep on how he designed the newsletter, his growth strategy, and how he approached monetization.

When it comes to distinctive newspaper designs, the print edition of The Financial Times stands out. The 135-year-old publication is instantly recognizable for its salmon pink paper, and it's become a status symbol for London's monied elite. The newspaper's web presence is extremely successful as well. In early 2022, it announced it surpassed 1 million digital subscribers, an especially impressive feat given its hefty price tag of over $400 a year. So given this success, why did the FT launch a mobile app last year that only costs around £5 a month? To answer this question, I turned to Malcolm Moore, a longtime Financial Times editor who was put in charge of FT Edit, which is the name for the new mobile app. We discussed why he was chosen to lead the initiative, what the app has to offer that differs from the main newspaper, and who the audience is for the product.

My newsletter: https://simonowens.substack.com/welcome As the media industry focuses on revenue diversification, more and more publishers are venturing into live events — both virtual and in-person. Not only can they be monetized in multiple ways, but a well-planned event can provide a great venue to forge a deeper connection with your most engaged audience. But events are tricky to pull off and can be intimidating for those who haven't hosted one before. For this episode, I pulled together a panel of people who run some of the most successful events companies in the world. They include: Chris Ferrell, CEO of Endeavor Business Media Bo Brustkern, co-founder of Fintech Nexus John Allsopp, who runs one of the most influential conferences for web designers, developers, and digital creatives Ross Douglas, founder of Autonomy Paris, a major trade show Sarah Peck, a podcaster who launched the Wise Women's Council Boye Fajinmi, co-founder of The Future Party And Randy Gage, a New York Times bestselling author In our discussion, we talked about everything including what to charge, picking a host city, finding sponsors, and negotiating with venues.

While podcasting has been around since the mid-aughts, it's only within the last half decade that the industry started generating significant revenue, finally crossing $1 billion in 2021. And until recently, there were very few journalists who were solely dedicated to writing about podcasts. That's a big part of the reason that in 2017 James Cridland decided to launch Podnews, a B2B newsletter that covers the industry. A longtime radio veteran who once worked for the BBC, James realized that there was a major need for a daily news digest of all the various startups and media outlets that were operating in the space. And as his readership grew, he found that there were plenty of companies that were willing to pay to reach his hyper-niche audience. In my interview with James, we talked about his approach to compiling his newsletter, his monetization strategy, and why he insists on coding most of his tools from scratch.

If you read articles about the state of local news, you'll come away with a pretty pessimistic view of the industry. But while legacy newspapers have certainly faced a steep decline, there's a burgeoning explosion of local media startups that are innovating in the space. One such company is Overstory Media. What started as a single local newsletter operating in Victoria has since expanded into 14 separate verticals operating all across Canada. In a recent interview, I spoke to CEO Farhan Mohamed about why he got into local news, his company's acquisition strategy, and why he's optimistic about the state of local news.

B2B used to be the least sexy space in media, but in the last decade we've seen a new crop of B2B media companies that are proving to be far more innovative than their B2C peers. Recently, I convened a panel of experts to talk about all the various aspects of B2B media — including running events, launching paid subscriptions, finding sponsors, and building out niche editorial products. What you're about to listen to is a recording of a live Zoom call I had with my newsletter's paid subscribers. I host these calls at least twice a month, and for each one I recruit some of the world's foremost experts in media and content. If you want access to these calls, then you need to become a paid subscriber to my newsletter. Go to simonowens.substack.com. That's simonowens.substack.com.

Visit https://memberful.com/simonowens Matt Brown didn't set off to build his own solo newsletter business, but he fell into it after taking a buyout at Vox Media sports site SB Nation during the height of the pandemic – a period when very few media companies were hiring. While his SB Nation beat covered all of college sports, Matt decided to niche down with his own newsletter – which was called Extra Points – to focus specifically on the business side of college athletics. This gave him the edge he needed to find a loyal audience, and he quickly scaled it up to thousands of readers. In my interview with Matt, we talked about why he left Vox Media, how he monetized his newsletter, and what made him want to sell it to a larger media company.

Visit Memberful: http://memberful.com/simonowens When the media outlet Roca News launched in the year 2020, it started creating just about every kind of content you can imagine. There was a newsletter, a podcast, and accounts on every single social media platform. But this everything-but-the-kitchen sink approach didn't seem to work, so the founders decided to focus mostly on a single platform: Instagram. Over the next two years, they leveraged Instagram's visual storytelling features to deliver a digestible form of news to its young followers. This singular focus allowed it to grow to over 1.1 million followers. Then, starting in 2022, it branched out into other mediums. It reinvested in its daily newsletter and also launched a TikTok account where it publishes more humorous, entertainment focused content. It also started building a dedicated mobile app, which it's launching soon. In this episode, I interviewed co-founder Max Towey about the Roca News origin story, its Instagram growth, and how it's begun monetizing its content.

My newsletter: https://simonowens.substack.com/ You've probably noticed that true crime is having a bit of a moment right now. Podcasts dedicated to the genre dominate the charts, and every week there's a new hit series on one of the major TV streaming services. Jim Brown approached true crime from a different direction. Rather than launching a show, he used his tech and product skills to build a database of cold cases. Think of it as a kind of Wikipedia for unsolved crimes. He then created ways for users to submit updates and participate in the discussion around these cases. The site, which is called Uncovered, now attracts tens of thousands of monthly visitors and recently played a key role in solving a cold case. I spoke to Jim about building the site, how it attracted its initial visitors, and its monetization strategies.

Visit https://signup.whosponsorsstuff.com/sales-pro/?source=simonowenspodcast Louie Woodall knows his way around a financial disclosure document. Since graduating college, he's worked for several media outlets that report on the intricacies of financial risk. In 2020, he decided to combine this expertise with his interest in climate change and launched Climate Risk Review, a Substack newsletter that analyzed climate disclosure documents published by major corporations around the world. The newsletter was a side hustle, but it eventually amassed an influential readership of bankers and other finance professionals, many of whom converted into paying subscribers. Eventually, Louie realized he needed to make a decision: should he continue it as a side hustle or try to make it his fulltime job? He decided on the latter option, and to help ease that transition he found a company that would not only acquire the newsletter, but also employ him to be its full time editor. In our interview, we talked about the newsletter's origin story, his monetization strategy, and how the publication will evolve under the umbrella of a larger company.

Visit Memberful: https://memberful.com/simonowens The podcast industry is around 17 years old, and Libsyn was among the first companies launched to service that industry. For most of that time, it focused on paid podcast hosting, but in recent years it's acquired companies that specialize in podcast advertising and subscriptions. Libsyn needs that more diverse product offering if it wants to compete with rising podcast behemoths like Spotify and SiriusXM. I recently sat down with Dave Hanley, who helps run its advertising operations. He told me the story behind Libsyn's acquisition of his podcast advertising platform and the company's strategy for recruiting the next generation of hit podcasts.

Check out the News Guest podcast: https://bit.ly/news-guest When Boye Fajinmi started hosting parties with a few of his friends, he had no idea that it would become a sprawling events and media company. They were just looking for a fun way to network with other creative workers like themselves. At the time, Boye worked at Paramount Pictures and was pursuing a traditional Hollywood career, but the success of those early parties led him to believe that he could build something of his own. Flash forward a decade, and The Future Party – which is what the company came to be called – now hosts dozens of events a year and works with some of the largest luxury brands in the world. It also publishes a daily newsletter that reaches 150,000 people. Boye and I sat down to discuss The Future Party's origin story, its monetization strategy, and why they decided to expand beyond events into media.

Get a 10% discount on a subscription: https://simonowens.substack.com/a30836c1 It's incredibly difficult to convert your audience from free readers/viewers/listeners into paying subscribers. In this meeting, we're going to discuss all of the optimization strategies that increase conversion and reduce churn.

Visit Memberful: https://memberful.com/simonowens In terms of career advancement, Brandi Kruse was at the top of her game. As a TV news correspondent in the large media market of Seattle, she was paid more than most of her industry peers, and she even hosted her own longform weekly talk show. But in late 2021, she quit her job and immediately launched her own podcast called Undivided. Within weeks of the launch, she amassed over 2,000 paying subscribers on Patreon, and she now delivers her commentary and interviews to over 200,000 followers across Facebook, Twitter, and YouTube. How did Brandi find this audience, and why did she ditch her well-paying job in TV? In our interview, she explained how she grew a large following on Facebook and used it as a launching pad for her independent career. She also told me about her efforts to expand beyond local news and into national politics.

Visit Memberful: http://memberful.com/simonowens Over the past decade, several major media companies have invested in building out their data journalism operations. ABC News has FiveThirtyEight, The New York Times has The Upshot. And Vox Media runs Vox.com. These outlets have leveraged publicly available data to explain complicated stories, and the infographics they create are easily shareable on social media. But most media outlets don't have the resources to hire an expensive data team, especially if they operate at the local level. That's where Stacker comes in. Rather than producing journalism for its owned and operated site, it distributes its content as a newswire that can be syndicated by any news company. What's more, it doesn't even charge for this service. That means virtually every news outlet has access to its top-quality reporting. How can Stacker afford to give away its content for free? To answer that question, I brought on co-founder Noah Greenberg. He walked me through Stacker's origin story, how it found its initial publishing partners, and how it developed its monetization strategy.

Visit SparkLoop: https://sparkloop.app/partner-network?utm_campaign=simonowens If you're aware of Morning Brew, it's probably because of its daily business newsletter. Since its founding in 2015 by two college students, it's grown to over 4 million subscribers, and its news digest format has been copied by dozens of other media startups. But since getting acquired in 2020 by Business Insider, Morning Brew has expanded into new niches in verticals. Not only has it launched several B2B industry newsletters, but it also invested heavily in podcast and video production. That's where Dan Toomey comes in. After graduating college in 2020, he pitched Morning Brew's founders on the idea of him coming on board to create video, and to his surprise, they went for it. After experimenting with several different formats, Dan started creating sketch comedy videos for TikTok, and it worked. Every morning he woke up, scanned that day's business news, and chose a topic to parody on video. In our interview, Dan talked about how he came up with the format, his daily routine for writing scripts, and Morning Brew's strategy to grow beyond TikTok and launch new video series.

Visit SparkLoop: https://sparkloop.app/?utm_campaign=simonowens If there's one thing Twitter's known for, it's character limits. It famously only allowed 140 of them and then later expanded to 280. In some ways, that forced brevity made Twitter what it is today: a real-time commentary on what's going on in the world. But for years, Twitter has been trying to expand beyond its own character limits, first by launching features like photos, gifs, and videos. It launched a threading tool that allows you to string several tweets together. In 2021, it acquired newsletter platform Revue. And then just recently, it debuted a new tool called Notes. Though it's still in the testing phase, Notes will allow users to publish longer blog posts within their Twitter feed. But is this something users actually want? Or will it eventually join the very large graveyard of social media features that never caught on? To answer this question, I brought on Ernie Smith. Not only is Ernie one of the foremost experts on publishing platforms and newsletters, he also got early access to Twitter Notes and tested them out for himself. He gave me his initial reactions to the tool and we discussed whether it would usher in an era of longform writing to Twitter.

Visit Video Husky: https://bit.ly/vh-simon-owens-pod When Nick Meacham first joined SportsPro in 2010, it mainly existed as a B2B print magazine that monetized through advertising. The editorial staff was tiny and it didn't have much of a web presence. But after taking over the business operations, he rapidly expanded it into new ventures – first by launching a series of lucrative conferences that targeted multiple industries within pro sports, and then by rapidly building out its digital operations. In an interview, Nick explained to me why he made such a big bet on events, how the company adapted during the pandemic shutdown, and where he sees more opportunities to monetize the outlet's digital content – including his plans to launch a subscription paywall.

Visit Video Husky: https://bit.ly/vh-simon-owens-pod During their combined 20 years at The Wall Street Journal, Bradley Hope and Tom Wright covered some of the most momentous stories to hit the financial world, but none were as consequential to their personal careers as their reporting on Jho Low, a Wharton grad who was caught stealing billions of dollars from investment funds. Their dogged investigation led to the publication of the book Billion Dollar Whale, an instant bestseller that transformed them into A-list writers, on par with Michael Lewis and Malcolm Gladwell. Rather than simply returning to their newspaper jobs, they partnered on a new media entity called Project Brazen. Unlike most digital media companies, Project Brazen has no ambitions to churn out large quantities of web content. Instead, it only focuses on ambitious, investigative storytelling that can be adapted into multiple mediums that include podcasts, books, film, and television. How does Project Brazen go about vetting and staffing these projects, and what are the best ways to monetize serialized storytelling? Those are some of the questions I put to co-founder Bradley Hope in today's interview.

Visit https://theygotacquired.com/newsletter When everyday people hear about space-related news, it's usually in association with an organization like NASA or SpaceX. But while Elon Musk is great at grabbing headlines, the space industry actually comprises a vast constellation of companies that generate hundreds of billions of dollars a year. And it's only set to expand; Morgan Stanley projects it'll reach $1.25 trillion by 2040. Given the size and growth of this industry, it's probably a surprise to no one who listens to this podcast that there's an enormous opportunity for the B2B media outlets that cover it. One of the most exciting entrants into that space is Payload, a daily newsletter that launched in 2021. Though Payload was bootstrapped for its first several months, it announced a $650,000 seed round last year that was led by Winklevoss Capital, the venture firm run by Cameron and Tyler Winklevoss. It's since hired an editorial staff and landed its first major sponsors. Payload was founded by Mo Islam and Ari Lewis, and in December 2021 I interviewed Mo about the newsletter's origin, its audience development strategy, and its plans to monetize its influential readership.

Visit https://www.transizion.com/ There were a lot of media companies that were vulnerable to the pandemic shutdown, but perhaps none more so than Pop Up Magazine. Not only was its content delivered through live performances, but the hosts made special care during each event to tell the audience that nothing that night would be recorded. Part of the magic, in other words, was the show's ephemerality. Of course, there was no way Pop Up Magazine could continue delivering on that promise once all in-person events went away. Instead, it had to adapt by somehow taking the magic of a live performance and delivering it over the internet. Not only did the magazine succeed in this endeavor, but the new restraints forced it to diversify revenue and expand its audience. With live events now returning, it's arguably stronger than ever. How did its staff accomplish this? In an interview last year, founder Chas Edwards walked me through Pop Up Magazine's pivot, from the hellish first weeks of the pandemic to its recent return to live events.

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.

For the past decade, publishers have utilized metered paywalls to grow their subscription businesses. Under that model, a reader gets to view a certain number of free articles before a paywall pops up and requires them to subscribe. But how many free articles should a user encounter before they hit a paywall? Increasingly, the answer to that question is: It depends. Publishers are starting to roll out dynamic paywalls that assign varying weights to different kinds of stories. If you're reading a business article, for instance, you may only get to read three free articles before hitting a paywall, but if you're perusing real estate listings you might get unlimited free access. The Globe and Mail has taken the idea of the dynamic paywall to the next level: it's developed a sophisticated AI that's able to analyze user behavior and determine the exact moment that a reader is most likely to subscribe. The AI is so powerful that the newspaper's editors now allow it to automate the placement of stories on its homepage and social media. I recently sat down with Gordon Edall, the person who runs the product team that developed the AI. We talked about how the paywall was initially designed, his experience recruiting data scientists, and why the Globe and Mail is licensing its AI product to other publishers.

Over the past several weeks, Spotify made several major announcements in the podcast space. It opened up its advertising ecosystem to anyone who hosts their podcasts on Anchor. It launched the ability for podcast hosts to create video versions of its podcasts. And it reported two major milestones on its quarterly earnings call: that it grew its podcast advertising revenue by 100% over the last year and that it surpassed Apple as the #1 podcast player in the U.S. What do all these announcements mean for the podcast industry? To figure it out, I invited on Jaclyn Schiff, CEO of a company called Podreacher. We discussed whether Spotify is a threat to the open podcast ecosystem and if it can become the YouTube of podcasting.

Google has a long and complicated relationship with news publishers. On the one hand, it sends billions of visitors to their websites every year through its main search engine, Google News, and other products. On the other hand, some publishers believe that the Mountain View company has siphoned away ad revenue on the back of their content. Amy Adams Harding, Google's director of analytics and revenue optimization for news and publishing, believes the search giant has the potential to provide a net benefit to publishers. Over the past several years, her team has developed a suite of tools aimed at helping media outlets to optimize their content so it reaches a bigger audience and drives more revenue. In our interview, Amy walked me through these tools and explained how they work. She also talked about why publishers need to adopt many of the strategies that ecommerce platforms developed over a decade ago.

Snigdha Sur's first idea for a media startup was a kind of Netflix-for-Bollywood streaming service, but when she spoke to investors about the idea, they all pointed out that it would be too easy for Netflix to simply copy her strategy. Though she quickly scrapped that idea, she still wanted to launch some sort of outlet that would service South Asian Americans, a group that she felt was underrepresented in mainstream media. This led to the launch of a free weekly newsletter that amassed several hundred readers. That free newsletter eventually evolved into The Juggernaut, a subscription-funded publisher that has a dedicated and growing fan base. I interviewed Snigdha about how she convinced YCombinator to let in a media startup, why she launched a hard paywall, and whether she'll ever introduce advertising into her revenue mix.

Most subscription strategies have a pretty straightforward value exchange: in exchange for a monthly payment, the subscriber gains access to premium content that's locked behind some kind of paywall. But what if you want to keep all your best content in front of the paywall? What could you still offer to your audience to make a monthly subscription payment worth the price of admission? Thousands of content creators have turned to platforms like Subtext, a tool that allows them to exchange text messages with their fans. Creators can either send mass texts out to their entire audience or get into individual conversations with subscribers. I've tried out the tool myself, and it's truly innovative. For this episode, I spoke to Subtext CEO Mike Donoghue. We talked about how his team developed the application and the different ways creators use it to generate revenue.

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Most major media companies are focused on scale. They want to reach ever larger audiences and then leverage that reach to drive more revenue. To accomplish this, they invest time and resources to create content across all major social platforms, from YouTube to TikTok to Snapchat. The Art of Manliness isn't that kind of media company. Let me give you an example of what I mean: it managed to build its YouTube channel to 1.2 million subscribers, an impressive feat, only to mostly abandon the channel several years ago. In a 2017 video, founder Brett McKay explained that there were other projects he'd rather devote his time to -- projects like writing a book, lifting weights, and producing his podcast. According to Jeremy Anderberg, the Art of Manliness's managing editor and one of only three full time employees, this kind of narrow focus is part of the company's ethos. It purposefully didn't try to scale like the BuzzFeeds and Vox Medias of the world. Instead, its team devotes nearly all of its energy into writing articles and producing a podcast, the latter of which has an incredibly loyal audience. That audience is so loyal that thousands have signed up for a 12-week bootcamp the company runs for "those who wish to revolt against our age of ease, comfort, and existential weightlessness." Anderberg spoke to me about how The Art of Manliness built its audience, why it launched its bootcamp, and what it's like to work for a media company that purposefully stays small.

In the spirit of Mental Floss's 20th anniversary, let me give you a few pieces of trivia about the magazine. It made a cameo in two episodes of Friends and an episode of Netflix's The OA. It started as a print magazine but discontinued its print edition in 2016. In addition to its web content, it produces several popular video series on YouTube. And in 2018, it was acquired by Minute Media, a conglomerate that mostly consists of sports media sites. Suffice it to say, the Mental Floss of 2020 looks a lot different than when it was a magazine published out of the dorm room of two Duke University students. I recently sat down with its editor in chief Erin McCarthy to talk about its post-print strategy and why a sports media company was interested in a publisher that specializes in history trivia.