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The Business of Content

Technology Podcasts

The podcast about how publishers create, distribute, and monetize digital content.

The podcast about how publishers create, distribute, and monetize digital content.


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The podcast about how publishers create, distribute, and monetize digital content.








He generates a six-figure income through Patreon and Substack

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...


This business-focused newsletter grew to over 50,000 subscribers

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...


He launched several local news sites around Washington, DC

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...


He ran the newsletter strategy for BuzzFeed and The New Yorker

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...


How to launch a hit audiobook

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...


Can Digg return to its former glory?

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...


His video game song adaptations generated millions of views

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.


Inside The LA Times's podcast strategy

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...


How a pencil artist generated millions of views on YouTube

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...


A local media company built on email newsletters

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...


Monetizing a political newsletter during an election year

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...


She built three successful media ventures from the ground up

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...


How the site Amazing Ribs amassed 15,000 paying subscribers

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 almost...


Why every comedian hosts a podcast

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...


A publishing platform built for independent writers

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....


This guy built a B2B media empire

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...


How BuzzFeed is monetizing its travel vertical

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...


How to convert your audience into paying subscribers

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...


Why Twitter is launching its own podcasts

In its most recent earnings report, Twitter revealed that it has over 139 million daily users, but the company’s first podcast it launched in 2019 was designed to only appeal to a tiny fraction of those users. The show is called Character Count and is hosted by Joe Wadlington, a creative lead in the department that helps educate small businesses on how to leverage Twitter in their marketing. And that’s the focus of Character Count, highlighting some of the most effective ways in which...


How I plan to monetize this podcast

Where you can subscribe to my newsletter: So this is the 68th episode of my podcast, and if you’ve been listening to it for any amount of time, you’d know that it never has ads. And while I don’t have anything against podcasts that have advertising, I don’t envision a future for this podcast where I’m reading promos for Squarespace of Mailchimp. But at the same time, I’d like for this podcast to contribute to my income, mostly so I can justify...