The Business of Content with Simon Owens

By the time Richard Rushfield launched his newsletter The Ankler in 2017, he had held journalism jobs at several major media companies that included The Los Angeles Times, BuzzFeed, and Gawker. But because he served as a behind-the-scenes editor in most of these roles, he didn't have much of a personal brand to speak of, which meant he needed to build a newsletter readership from the ground up. Despite these headwinds, Richard managed to replace his full-time salary within about two years, and The Ankler is now a must-read for virtually every Hollywood studio executive. In our interview, he explained how he built his audience and why he prefers his life as an independent writer much more than his past career as a traditional journalist.

If you're in the media, then you're probably aware of The Daily, the massively successful podcast produced by The New York Times. It now receives over 4 million downloads a day and generates eight figures in revenue for the newspaper. But is it possible to replicate The Daily's success without the institutional support? That's the question Jamie East set out to answer. A year ago, he and a few colleagues launched The Smart 7, a 7-minute podcast that's published each weekday at 7 a.m. Its relatively simple format and consistency made it easy for listeners to build it into their daily habits, and within its first year it hit five million downloads. I recently interviewed Jamie about why he struck off into indie podcasting when he already had a successful career in traditional broadcasting, and he explained how he plans to build an entire network of niche daily podcasts.

If you look at the Apple and Spotify podcast charts that track the most downloaded shows every week, you'll notice that many of the most popular podcasts belong to large networks. Organizations like Gimlet Media, Wondery, and NPR are able to pool their resources to promote their content, and this gives their shows a distinct advantage over independent podcasts, even those of similar quality. That's why some indie podcasters have formed collectives. These entities provide many of the same benefits of a network while still allowing for the podcaster to own their intellectual property. To get a better perspective how these collectives work, I interviewed Amanda McLoughlin, the founder of a collective called Multitude. In our interview, Amanda explained her process for recruiting shows to join Multitude, the collective's business model, and why podcasters shouldn't be timid about asking their audience for financial support.

David Harper wrote hundreds of thousands of words over a five-year period without making a single penny from his comic book criticism. In 2009, he and a couple friends launched Multiversity Comics, a fan website that went on to be nominated for an Eisner Award, which is basically the comic book equivalent of an Oscar. In 2015, David struck off on his own, launching an incredibly popular podcast and website. As his audience grew, he began to think about ways he could monetize it, and he eventually rolled out a paid subscription model. In my interview with David, we talked about the origin of his comic book fandom, where he found his audience, and how he designed his subscription offering.

Every morning, tens of thousands of people who live in cities like Miami, Portland, and Pittsburg receive a conversational email that updates them on the latest news within their city. These newsletters don't often contain any original reporting, but they've been embraced by their local communities because they're so effective at distilling dozens of newspaper articles, social media posts, and government announcements into an easy-to-read digest. These newsletters are owned and operated by a company WhereBy.US. Launched in 2014, the company built out a scalable model that includes newsletters, self-service ads, and paid memberships. I recently interviewed its founder Christopher Sopher about how he built the company, its role within local journalism, and why he decided to spin off a SaaS publishing product that he sells to other media entrepreneurs.

Daniel Orubo had no intention of becoming a media personality when he graduated with an engineering degree in 2013, but his funny tweets just happened to catch the eye of a Nigerian publishing executive who planned to launch a BuzzFeed-like website called Zikoko. Daniel started out as a senior writer, crafting humorous listicles like the "12 characteristics of Nigerian mothers," but over the next half decade he helped transform Zikoko into a cultural force that's willing to discuss hot-button issues around sexuality -- the kind of issues that are typically considered taboo in conservative Nigeria. Daniel is now the editor-in-chief of Zikoko, and we recently sat down to discuss how the website found its audience and why it expanded beyond funny memes so it could tackle controversial topics.

These days, nearly every digital publisher utilizes some kind of reader revenue strategy, but when Jessica Lessin quit her Wall Street Journal job and launched The Information in 2013, it was still a novel concept. At that time, the paywalls that existed were usually metered, but Jessica was among the first to place her website's entire library of content behind a hard paywall. If you wanted to access to any of its articles, you needed to fork over up to $400 a year for the privilege. In our interview, I asked Jessica about why she chose that model, how her journalists compete with much larger publishers for scoops, and what marketing strategies drive the most paid conversions.

https://simonowens.substack.com/ I just passed my one-year anniversary of launching my paid newsletter, so I decided to dive into some of the biggest lessons I learned during that time.

If you review Kevin Jones's resume on LinkedIn, it's easy to see why he ended up founding a sports podcast network. He's worked in virtually every sector of the sports media industry, from creating content for pro football teams to reporting for traditional radio stations to writing for sports news sites. He also launched Striking Gold, a 49ers-focused podcast that eventually accrued several thousand listeners. But Kevin wasn't content with simply being a podcast personality. Back in 2018, he began to notice that there were a lot of people like him -- podcasters with extremely passionate fan bases but no way to convert that fandom into actual revenue. So he began pitching them one by one on joining Blue Wire Podcasts, a network that would help them produce their shows and sell advertising in exchange for a cut of the revenue. Flash forward two years, and Blue Wire has since taken on several million dollars in investment, is now producing narrative documentary podcasts, and recently signed a huge deal with one of Las Vegas' biggest hotels. I recently sat down with Kevin to discuss how he convinced podcasters to join his network, his approach to working with talent, and why he's doubling down on longform narrative series.

Over the past year, thousands of journalists have announced the launch of their paid newsletters, which are often hosted on platforms like Substack. Writers with already-existing large audiences have seen immense success with this strategy, pulling in six figures incomes within weeks of debuting their new newsletters. But the vast majority of writers don't have huge Twitter followings to promote their newsletters to. For them, growing a sustainable media business can take years of work, and many don't have enough savings in the bank to hold out for that long. That's why we're seeing a new trend in which writers team up to launch bundled subscriptions. This approach allows writers to cross pollinate their audience growth and ramp up content production to make a subscription much more worthwhile. Publications that include Defector, the Discourse Blog, Brickhouse, and Every have seen tremendous success with this model. To understand how these writer cooperatives work, I spoke to Mark Stenberg. Stenberg runs his own Substack newsletter and has spent the last few months reporting on the creator economy for Business Insider. He recently moved over to Adweek to cover the media beat.

The last 15 years have not been kind to the local news industry, with thousands of newspapers either reducing staff or closing down entirely. But not all newspapers have been affected equally, and some of the hardest hit chains were owned by hedge funds and private equity firms that had no actual interest in investing in journalism. Family-owned newspapers seemed to have fared better, and that seems to be the case for Forum Communications, a chain of newspapers and other media outlets situated in the midwest. A few years ago, the company's newspapers rolled out a digital subscription model, and so far it seems to be performing above expectations. I recently interviewed Stephanie Schroeder, Forum's Chief Digital Marketing Officer, about the gargantuan amount of work that went into this pivot and what strategies resulted in the most success.

According to some estimates, corporations across the world spend upwards of $42 billion a year on content marketing, and they do so with the philosophy that by acting like media companies, they can engender trust with potential customers and drive sales. One of the people who helped sell the corporate world on this marketing philosophy is Joe Pulizzi. In 2007, Joe founded the Content Marketing Institute, and through its constellation of articles, videos, courses, and conferences, it convinced thousands of executives that the frictionless distribution of the internet allowed virtually everyone to become a media company. I recently interviewed Joe about his journey. We discussed whether freelance journalists should take on content marketing gigs, which companies have been particularly good at content marketing, and whether we're currently in a content bubble.

Like a lot of people on the political Left, Geoff Sharpe grew frustrated by how successful conservatives were on Facebook. For years, he watched as right leaning conservative groups built huge Facebook followings, which allowed them to promote their highly partisan views to millions of Canadian citizens. So Geoff and his colleagues decided to do something about it. They initially launched their own left-leaning Facebook page, growing it to hundreds of thousands of followers. But they then wanted to pivot to something even more ambitious: a standalone website that published original content from leading progressive voices. To do this, they launched a crowdfunding campaign, and over the last year they've rolled out a membership offering that helps generate recurring revenue. I interviewed Geoff about why the political Right does so well on Facebook, how he designed the membership program, and what impact his site has had on Canadian politics.

There's a common misperception that many non-lawyers have about how legal contracts are written. Most people probably assume that a lawyer writes each contract from scratch, but in reality the lawyer is most likely copy and pasting clauses and sections from already-existing contracts and modifying them for their particular client. One of the resources lawyers often turn to for this is Law Insider. Founded in 2010, Law Insider indexes the millions of contracts that have been uploaded to the SEC website by publicly traded companies. It generates over 4 million monthly pageviews and has over 250,000 registered users, about 5,000 of which pay $30 a month to access its archives. I recently interviewed the site's co-founder Preston Clark about how he and his partner came up with the idea, what they did to build up its massive audience, and why they're expanding into a full-fledged media company that produces everything from articles to YouTube videos.

Over the past year, dozens of writers have left their mainstream media jobs to launch their own standalone newsletters and publications. In almost every case, the writer monetized his content through paid subscriptions, usually with a tool like Substack. Rick Ellis never bothered with paid subscriptions. Instead, his website AllYourScreens.com generates so much traffic each month that he's able to make a good living mostly through programmatic advertising. Ellis has been operating AllYourScreens.com off and on since the early 2000s, but a few years ago he decided to abandon traditional media completely to focus on the site full-time. I recently interviewed him about how he found his audience, what his weekly writing schedule looks like, and why he has no interest in building out a paid subscription business.

Subscribe to my newsletter: https://simonowens.substack.com/

Max Rofagha didn't have a background in media prior to launching Finimize. He also didn't have a background in finance for that matter. It was while conducting research on how to manage his own investments that he saw an opportunity for a daily newsletter aimed at helping millennials become more literate in finance. Flash forward four years and Finimize now has over 1 million subscribers, a staff of financial analysts, and a worldwide community of young professionals who often meet up for in-person events. I recently interviewed Max about his early audience development strategy, how his subscribers organize their own in-person events, and why he decided to launch a subscription-funded mobile app.

Per Grankvist had the kind of media career most journalists only dream of. He was a high-profile columnist for a leading newspaper and a regular face on one of Sweden's top broadcast networks. But over time he grew disillusioned with mainstream media and its tendency to dumb down coverage of complicated policy issues. So Per quit his traditional media jobs and launched his own outlet. It started with just an Instagram account that explained thorny election issues, but from there it blossomed into an entire media outlet that spanned across social media, podcasts, and newsletters. I recently interviewed Per about how he built the company, his approach to monetization, and whether he misses working for mainstream media publications.

Peruse a newsstand full of men's magazines and you'll probably notice a few common themes. The cover either features a bikini model or a suit-clad male celebrity. Inside, you'll find stories meant to appeal to what many in the mid-20th century would have considered the "ideal" man -- articles about scotch, cigars, and custom suits. You won't find many of those kinds of features in MEL Magazine, a digital-only publication that launched in 2015. Owned and operated by Dollar Shave Club, MEL aims its content at the under-40, educated, likely-urban male...a man less inclined to traditional gender roles who is much more in touch with his feelings and spends an inordinate amount of time on the internet. I recently interviewed editor-in-chief Josh Schollmeyer about how he came to define this 21st century male, where his staff sources its article ideas, and how Dollar Shave Club will profit from its investment in the magazine.

Lon Seidman didn't launch on YouTube with the goal of becoming a top gadget reviewer. In fact, he stumbled upon that aspect of his career while struggling to run a video local news startup in Connecticut. Almost on a whim, he recorded a video review about one of the cameras he bought for his startup, and to his surprise, the video blew up. Flash forward a decade, and Lon now has tens of millions of views across YouTube and Amazon. He managed to carve out a niche among a crowded field of gadget reviewers, and he's now making a pretty good living through a mixture of YouTube advertising, affiliate sales, and Patreon subscriptions. We walked through how he accomplished all this in our interview.

If you had to make a list of technologies that are most important to the average person's day-to-day life, data centers would sit near the top of that list, and yet chances are you know very little about them. There are a few reasons for this. For one, they're not sexy in the way that an iPhone or a cutting-edge drone is sexy. But also the people and companies who run data centers are fairly secretive, mostly to protect their machines from any sort of attack. This combination of secrecy and obscurity has made Rich Miller's expertise very lucrative. He's spent the last two decades covering data center tech for various news outlets he's owned. His current site, Data Center Frontier, is a must-read for anyone working in the $60 billion+ industry. I interviewed Rich about how he accidentally fell into the beat, why he sold his first data center site, and what made him want to start a brand new one from scratch.

Back in late 2019, nearly all the writers for the beloved sports site Deadspin resigned en masse after butting heads with the private equity executives who owned the website. After they left, there was lots of speculation about where those writers would turn up. Would they simply get new jobs, or would they band together to create their own site? And then in July 2020 we got our answer: they launched Defector, an employee-owned publication that would be monetized mostly through paid subscriptions. To build the site, they turned to a guy named Austin Smith. Austin is the founder of an agency called Alley Interactive, and over the past decade he's helped build and maintain the websites of many of the most well-known news publishers in the world. I sat down and interviewed Austin about his career in media, what goes into building a good publishing platform, and why he's recently begun working with news startups like Defector to help them get off the ground.

Abby Glassenberg runs a trade association called the Craft Industry Alliance. It has over 1,600 paying members who work in the arts and crafts industry. It hosts conferences, schedules networking events, publishes industry news, and provides ongoing education. Pretty much the kind of services that most trade associations offer. But unlike most trade associations, this one grew out of a one-person blog. Abby started it as a hobby, but it soon amassed a large audience, which then led to a book deal, a thriving Etsy store, and a popular podcast. I recently interviewed Abby about why she went the trade association route and how she's growing its revenue by 20% a month.

In just about every article about TikTok, it's portrayed as a video repository created by and for teens. Indeed, nearly every single one of its top-earning creators are under the age of 20, and polls have found that it ranks second only to Snapchat as U.S. teens' favorite social media app. Zarna Garg is an exception to the rule in multiple ways. For one, she's a 45-year-old mom who barely even knew TikTok existed a year ago. And while most top users traffic in dance videos, lip syncs, and comedy sketches, Zarna's specialty is standup comedy. Many of her jokes aim to capture the South Asian immigrant experience, and she says she's carved out a niche explored by very few comedians, both inside the U.S. and in India. I interviewed Zarna about how she cracked the TikTok algorithm, what impact her success has had on her comedy career, and how she's leveraging that success to try to break into Hollywood.

If you traveled back in time 100 years and perused your average newsstand, you'd find dozens of magazines that published serialized fiction. Millions of subscribers eagerly awaited new installments from their favorite authors, and a serialized story in a high circulation magazine could launch a new writer's career. But by the turn of the century, serialized fiction was all but gone. Or at least it was in written and audio form. TV shows, on the other hand, began to adopt complex, serialized narratives, and by 2015 these kinds of shows were dominating both online and offline discussion. That's the same year a new app called Serial Box launched. Serial Box operates a lot like a TV studio. Its stories are delivered in weekly installments. Each series is written by a collaborative writers room. The most successful series will often continue for multiple seasons. There's only one major difference: instead of producing TV shows, Serial Box publishes text and audio stories that could be read or listened to in the same way you consume a novel. I recently interviewed co-founder Molly Barton about Serial Box's origin story, how the company produces new series, and why she's pursuing adaptations outside of the Serial Box app.

Polina Marinova had the kind of media career that many journalists dream of. After a brief stint at a media startup, she landed a job at Fortune Magazine and eventually got the role of head writer for Term Sheet, its daily newsletter on deals and dealmakers. After six years there, her resume and profile probably could have gotten her any mainstream media job she wanted. But instead, she left that steady job in March -- in the beginning of a massive recession -- to focus on her Substack newsletter full-time. The newsletter is called The Profile, and though she was running it as a side hustle while working at Fortune, she didn't debut the paid version until after she left. I recently interviewed Polina about why she decided to make the jump during such uncertain economic times, how she differentiates the free from the paid content, and her strategy for growing the newsletter's audience these past six months.

My newsletter: https://simonowens.substack.com/ So the format to this podcast is pretty straightforward and consistent. I bring on a media entrepreneur or executive and interview them about their craft. But I'm also sort of a media entrepreneur myself, in that six months ago I launched a paid Substack newsletter that I hope to grow into a full-time job. Growth has been slow but steady, and over the six-month period I've experimented with a number of strategies to boost signups. Some worked, others didn't. I've still got a ways to go before it's completely replaced my consulting income, but I think I've made enough progress that it's worth pausing and looking back at some of the lessons I've learned along the way. So strap yourself in, because we're about to dive deep on my paid newsletter strategy.

With the journalism industry in freefall, there's a good chance that your local newspaper is experimenting with some kind of digital subscription offering. In many cases, this involves some kind of metered paywall where you're expected to start paying after consuming a pre-determined number of articles. Hundreds of newspapers have installed paywalls like this, but they've seen mixed results, with many reporting disappointing revenue numbers. But is content the only thing an audience will pay for? That's a question Doug Lesmerises, a Cleveland.com sports columnist, sought to answer. A few years ago he co-founded a popular sports podcast but had a difficult time attracting advertisers. Then some executives from his newspaper's parent company approached him with a new product called Subtext. It provides a simple way to allow paying subscribers to exchange text messages with Doug and other hosts. The service was a surprise hit, and Doug now uses the app to crowdsource questions for the podcast and send his paying subscribers quick-hit analysis when Ohio sports news breaks. I interviewed Doug about how he incorporated texting into his show and what other local journalism outfits can learn from his success.

When Naoise McNally and her business partner launched One Fab Day, neither of them had any experience working for a media company. Naoise didn't even have much knowledge of the wedding industry outside of planning her own wedding. But the lack of wedding-focused internet resources in Ireland presented a clear market opportunity, so they went for it. Flash forward several years, and the site now has a full time staff and an interesting business model. Instead of relying on traditional advertising, it charges wedding vendors to be listed in an index it curates for readers. I recently interviewed Naoise about One Fab Day's founding, how she settled on a business model, and what she hopes the site can accomplish now that it's owned by a major media company.

Quick question: how big do you think the global freight industry is? If your guess is in the billions, then you're aiming too low. According to some estimates, global logistics generate somewhere in the range of $8 and $12 trillion annually. For Craig Fuller, that number represents a massive opportunity. His company Freight Waves covers this industry across text, video, and podcasts. But Freight Waves is a lot more than just a trade publication; it also delivers data and intelligence. In fact, it's much more analogous to a Bloomberg LP, which in addition to its massive media business also generates billions of dollars a year from its expensive Bloomberg terminals. I interviewed Craig about how he built his expertise in freight, where the company sources its data, and why it recently took on venture capital investment.

When Terrell Johnson launched on Substack, he had no intention of rolling out a paid newsletter. He was just trying to escape Mailchimp's expensive fees and liked that Substack would send his newsletter for free. About a decade earlier, Terrell had created HalfMarathons.net, a running focused website that grew so popular that at one point it was generating six figures in revenue just from Google Adsense. His free newsletter served mostly as a form of marketing for the website, but he eventually began to wonder if his most engaged readers would be willing to pay for it. So he flipped on Substack's payment features, and while it wasn't an overnight success, he's gradually grown it into an impressive community of paid subscribers. I interviewed Terrell about where he got the idea for HalfMarathons.net, how he built up an audience, and why he eventually grew to distrust Google as his primary traffic driver.

Josh Spector was blogging before most people even knew what a blog was. Over the span of a decade, he started and abandoned several of them, often before they had a chance to amass much of an audience. But in 2011 he got more serious about audience growth for a blog he ran that focused on teaching standup comedians how to market themselves, and to help drive traffic to it he launched a newsletter. Pretty quickly, he grew addicted to the newsletter medium, and a few years later he merged a couple of newsletters he was running into a single list and renamed it For the Interested. Since 2016, he's been sending out new issues each week featuring ideas to help creators to produce, promote, and profit from their creations. For the Interested now has over 25,000 subscribers, and Josh recently launched a paid spinoff newsletter. I recently interviewed Josh about how he grew his audience, the role his newsletter plays in his consulting business, and why he thinks so many writers are approaching paid newsletters the wrong way.

A year ago, Jesse Singal had a very traditional freelance writing career. When he wasn't working on his book, he'd write articles for places like The Atlantic and New York magazine. The mixture of book advance and freelance revenue provided a reasonably stable income. Today, the economic climate for journalism is much more dire. The Covid-induced recession has led to mass layoffs and a squeeze on freelancer budgets. Some publications have closed up shop completely. But in many ways, Jesse's income streams are more secure than ever. That's because he launched a paid newsletter through Substack and co-hosts a hit podcast that monetizes through Patreon. Together, these two sources generate a nice six-figure income for him. I recently interviewed Jesse about why he decided to monetize his audience directly, how he designed his paid offerings, and whether he thinks platforms like Substack and Patreon can replace the income for laid-off and underemployed journalists.

When Tyler Morin was in high school, he dreamed of going into journalism, but his parents convinced him to major in finance instead. After graduating, he went into the financial sector, but he never lost his ambition to work in media, and he became obsessed with daily newsletters like Morning Brew and theSkimm. After experimenting with a group sports blog, he pivoted to launching a daily newsletter called The Water Coolest. The Water Coolest found an audience and quickly grew to tens of thousands of subscribers. I recently interviewed Tyler about the founding of his company, how he found his first advertisers, and why he decided to launch a paid version.

Arlington Country, Virginia is a suburb of DC. It has over 236,000 residents, thousands of local businesses, and an average household income north of $100,000. With those sorts of attributes, you'd think it would have a vibrant daily newspaper, but instead its citizens mostly rely on the Washington Post metro section and a few weekly newspapers to get their news. Or at least that's all they had up until about a decade ago. In January 2010, a former TV news producer named Scott Brodbeck launched Arlington Now, an online only news site dedicated specifically to Arlington. It quickly grew an audience and revenue base, and Scott has since launched several other sites covering Northern Virginia. I recently interviewed Scott about the founding of Arlington Now, how his journalists approach their coverage, and why he doesn't consider Google and Facebook to be much of a threat to his advertising revenue.

Dan Oshinsky didn't apply for an open position to run BuzzFeed's newsletter operations. He just happened to reach out to editor Ben Smith back when BuzzFeed was hiring a bunch of people with weird internet obsessions, and the company hired him without a clearly defined role. This dynamic granted Dan a lot of leeway in terms of how he approached BuzzFeed's newsletters, and he went on to launch several products, including multiple online courses and the newsletter This Week In Cats. A few years later he got hired to run newsletters at The New Yorker, which was focused on building out its paid digital subscriptions. Recently, he left that job to run his own newsletter consultancy. I recently interviewed Dan about how he built out BuzzFeed's newsletter strategy, the role of newsletters in driving paid subscriptions, and why he left such a prestigious job to strike off on his own.

The audiobook market is massive, with sales projected to hit $3.5 billion this year. What used to be a niche, expensive product is now one of the fastest growing mediums. In fact, The New York Times recently reported that audiobooks are one of the only book formats still growing in sales during the current pandemic-induced recession. But what does it take to launch a hit audiobook? How does the choice in narrator influence sales? And are book publishers worried about the market dominance of Amazon-owned Audible? These are all questions I put to Scott Dickey, the CEO of a company called Podium Audio. Podium is an audiobook studio that specializes in signing deals with self-published authors. It was the studio that produced the audiobook version of The Martian, the book that was made into a hit film starring Matt Damon.

In the mid-2000s, Digg was one of the most powerful websites on the internet. Powered by its army of users, the platform would send gargantuan amounts of server-crushing traffic to any content featured on its front page. Millions of people visited it each day and it turned its founder Kevin Rose into an internet celebrity. But you probably know what came next. A misguided redesign triggered a user revolt, and its audience abandoned it for Reddit and other platforms. Before long, it seemed destined to follow in the footsteps of Myspace and Friendster. Its story didn't end there. In 2012, the site sold to the startup studio Betaworks, which immediately went about trying to revive the Digg brand. In 2018, it was purchased by a company called BuySellAds. I recently interviewed Todd Garland, Digg's new owner and CEO. We discussed its current editorial operations, its monetization strategy, and his plans to restore Digg to its former glory.

I first discovered Gil Assayas, the musician otherwise known as GLASYS, when one of his YouTube videos made it to the front page Reddit. His amazing keyboard set up and sophisticated musical adaptations of well-known video game soundtracks caught the attention of several gamer subcultures, who then shared his videos widely across social media. I recently sat down with Gil and asked him about how he grew his fanbase and in what ways his viral videos have translated into career success.

The New York Times gets a lot of credit within the media industry for the blockbuster success of its podcast The Daily, but The Los Angeles Times was also an early pioneer within the medium. Its narrative true crime podcast Dirty John generated over 30 million downloads and was adapted into a TV show for Bravo. The newspaper has since gone on to launch ambitious shows chronicling the criminal trial of Bill Cosby and the famous murders committed by Betty Broderick. I recently interviewed Clint Schaff, VP of strategy and development, about the paper's podcast productions. He walked me through how shows get made, their monetization strategy, and his views on selling IP to TV studios and Spotify.

Jono Dry is the type of artist whose work is sold in European galleries by art dealers. He only finishes a few pieces a year, and most of his purchased pieces likely reside in the private collections of rich people, closed off from the public. But that hasn't stopped millions of people from viewing his work. That's because Jono films himself drawing each piece and uploads gorgeous time-lapse videos to platforms like Facebook, Instagram, and YouTube. On YouTube alone these videos have generated over 8 million views, and his success on social media has transformed him into a world-famous artist. I recently interviewed Jono about how he built his following and in what ways he's been able to leverage that following to advance his career.

We've seen several media companies launch over the past few years that specialize in sending out newsletters that summarize each day's news. Newsletters like theSkimm, The Hustle, and Morning Brew speak to their readers in a conversational style and have been embraced by millions of loyal subscribers. The folks behind 6AM City took that model and applied it to local news. Operating out of cities like Greenville, SC and Chattanooga, TN, each newsletter mines local newspapers, businesses, and social media accounts to produce a daily snapshot of the goings on in that urban center. To date, it's grown to over 230,000 subscribers and monetizes primarily through custom, native ads. I recently interviewed co-founder Ryan Johnston about how each newsletter operates and whether he thinks his company is producing quality local news.

Ben Cohen isn't the world's biggest fan of Facebook. The founder of a political news website called The Daily Banter, Ben worked hard to build up his reach on Facebook, and for a few years he made a decent living selling advertising against his content. But after the 2016 election, Facebook pivoted away from news, and virtually overnight The Daily Banter lost 90% of its traffic. Not only could he no longer pay his own salary, but he was also struggling to keep his stable of writers on board. Out of desperation, he moved the Banter over to Substack and doubled down on paid subscriptions. That was in early 2019. I recently checked in with Ben to see how his efforts are going and how a presidential election year affects subscription growth for a political newsletter.

Alexis Grant didn't start her career with the goal of building several media businesses. She simply wanted work as a reporter. After college, she got a job at the Houston Chronicle and then later accepted a role editing the careers section at US News & World Report. But something about the business of media intrigued her, and while at US News & World Report she launched a side hustle running social media and blogs for corporate clients. Eventually, she drummed up enough business to quit her day job and focus on content marketing full time. In fact, she launched an entire marketing agency that specialized in producing branded content. One of her clients was a personal finance website called The Penny Hoarder, and she was so successful at growing its audience that the company eventually acquired her agency and installed her as its editor in chief. By the time she left The Penny Hoarder a few years later, it was generating tens of millions of dollars in annual revenue. I recently interviewed Alexis about how she helped scale these companies and what she plans to do next.

Because I write and podcast so much about the business of media, I regularly get emails from founders of niche media companies who want to tell me about their successful ventures. A few months ago, I received an email from a guy who identified himself only as Meathead, and after reading only a few paragraphs I knew I wanted to have him as a guest for my podcast. Meathead, who's been writing about food on the internet since the days of dial-up AOL, started the website AmazinRibs.com almost as a lark. Flash forward 15 years, and it's the preeminent authority on all things barbecue. It generates a healthy mix of revenue from advertising, affiliate sales, books, and paid subscriptions, and it grew its business without help from any venture backing. I recently interviewed Meathead about writing for AOL when it was the biggest game in town, running the third most popular wine magazine, and stumbling into a website venture that made him one of the most famous people within the barbecue scene.

If you wanted to become a professional standup comedian in the 1990s, the path was pretty straightforward. You started by going to amateur open mic nights, where you would hone your act. Eventually, you'd develop five to 10 minutes of solid material and maybe get a slot opening for a bigger comedian. From there you'd work yourself up to bigger and bigger gigs, and if you were really talented and lucky, you'd land a slot on a late-night talk show, or, even better, get signed to an hour-long special for HBO. These days, the path for the aspiring comedian is completely different. Sure, there's still the open mic nights and the club gigs. But there's also a bevvy of online platforms that you can leverage to sharpen your craft and build a following. You might collaborate with other comedians and write sketches for a YouTube channel. You can practice your one-liners on Twitter. And you'll definitely want to launch a podcast. As a full-time standup comedian, Joel Byars has employed several of these strategies. I interviewed Byars about how comedians market themselves in this golden age of standup comedy and asked him why he decided to self-produce his own comedy special.

Let's say you're a writer who wants to publish your work to the web and eventually monetize it. These days you have plenty of options. You might open a Medium account and join the platform's partner program. Or maybe you launch a Substack newsletter. If you're really ambitious, you could throw together a Wordpress website and integrate it with a payment tool like Stripe. Or you could just launch an account on Ghost, a publishing platform created a few years ago by a guy named John O'Nolan. Before founding Ghost, John was the deputy head of design at Wordpress, and though he was always a fan of the open source CMS, he thought he could create something a little bit better. So John launched a Kickstarter campaign, and after raising tens of thousands of dollars, he developed Ghost. Today, it's used by some of the world's largest brands, and his hope now is that independent writers will use it to monetize their content. I spoke to John about the platform and why he thinks a writer should choose it over a competitor like Substack or Patreon.

When we talk about the media industry, we're usually discussing publishers that are geared toward a broad audience -- outlets like The New York Times or CNN or NPR. Even more niche publications like The Verge or Bon Appetit are designed to attract tens of millions of readers each month. But there's also an entire ecosystem of business-oriented publishers that operate in extremely narrow niches -- outlets aimed at sewage workers, electricians, and grocery store executives. Though their readerships are relatively small, they represent industries that collectively generate hundreds of billions of dollars each year. Because of this, B2B niche publishers, when run well, can be immensely profitable. Industry Dive is one such B2B publisher. Founded in 2012, the company now produces publications that cover over a dozen industries. I sat down with one of its co-founders Sean Griffey to talk about Industry Dive's origin story and how it bootstrapped its way to north of $22 million in annual revenue.

BuzzFeed CEO Jonah Peretti has expressed a lot of frustration with the large platforms that dominate our online browsing. In 2018, for instance, he complained that Facebook captures a lot of value from publishers and argued that it should share more of its revenue with them. That same year, he floated a merger of several digital media companies so they'd have more bargaining power against the platforms. And then recently he wrote a memo in which he lamented that publishers didn't receive enough credit for the consumer purchases they drive. "The two most important players in this chain are the publisher who inspired a consumer to take action and the companies that actually deliver the product But most of the profit is captured by digital middlemen who didn't create much value." In the memo, he promised that BuzzFeed was working hard to solve this attribution problem. To get an idea of how BuzzFeed plans to solve this problem, I recently spoke to Rich Reid, its senior vice president of global content. We talked about Bring Me, BuzzFeed's travel vertical that publishes a wide range of video and text content across its website and social channels. Recently, Bring Me formed an ad partnership with Hilton, and I asked Reid about how his team designed the campaign so that BuzzFeed gets full credit for any business it sends Hilton's way.

It's been nearly a decade since The New York Times launched its metered paywall, and its success has spurred just about every digital publisher to test out some form of reader revenue strategy. Many have followed in the Times's footsteps and debuted metered paywalls. Others have rolled out various membership options, offering everything from behind-the-scenes footage to exclusive commenting features to convince readers to open their wallets. But which tactics actually work? And how should publishers determine what to charge? To answer these questions, I spoke to Jacob Donnely. Donnely is the managing director of audience and growth at Coindesk, one of the leading cryptocurrency publishers, and runs his own paid newsletter about the publishing industry. We talked about how to design the perfect subscription offering and debated whether subscription fatigue is actually real.