The Business of Content with Simon Owens

You can’t write a history of Web 2.0 without including the contributions of Brian Alvey. After getting his start doing design work for traditional publications like TV Guide and BusinessWeek, Alvey teamed up with his childhood friend Jason Calacanis to launch a series of online publications. Eventually, the two created Weblogs, Inc, a blog network that went on to be sold to AOL. The content management system Alvey built would eventually power AOL’s portal and much of its websites. But Alvey didn’t stop there; he’d go on to build publishing platforms that would power everything from TMZ to Rupert Murdoch’s ambitious iPad app The Daily. I interviewed Alvey about what it was like to run a blog network in Web 2.0’s early days, how he ended up in a 45 minute meeting with Jeff Bezos, and why the iPad failed to save the media industry.

In 2014, Ben Thompson, a blogger who writes about the business of technology, announced he was quitting his job so he could write full time. His business model? He would send out four newsletters a week. One of those newsletters would be free, and if you wanted access to the other three, then you had to pay $10 per month. Within a year, Thompson had 2,000 subscribers, which, if you do the math, means he was generating $200,000 a year. At that point, he stopped publicly disclosing his subscriber numbers, but some predict that he’s increased his subscriber numbers by several thousand. Thompson was an early pioneer in the realm of paid newsletters, and since then there have been several other writers who struck out on their own with similar models. There’s Nick Quah’s podcast newsletter Hot Pod. There’s political writer Judd Legum’s Popular Information. Many of these newsletter writers have had to string together multiple services, from Mailchimp to Stripe, in order to manage their businesses. Now we’re seeing a few new companies on the market that want to serve as all-in-one platforms for paid email newsletters. Once such platform is called Substack, and it recently surpassed 25,000 paying subscribers for its participating newsletter writers. I interviewed the company’s cofounder Hamish McKenzie about the rise of paid newsletters, how to convert readers of a free newsletter into paying subscribers, and why his service is preferable to other membership platforms like Patreon.

Monica Reinagel had no background in broadcasting or radio when she launched a podcast called Nutrition Diva in 2008, but she was a trained nutritionist, had published several books, and was writing a regular column at a popular health website, and this was just the sort of background that Quick and Dirty Tips, a podcast network run by the book publisher Macmillan, was looking for when she reached out to it to ask if the company would consider taking her on. Flash forward a decade, and Reinagel now has over 500 episodes under her belt, and they’ve generated a collective 35 million downloads. I sat down with her recently to discuss how she benefited from joining a podcast network, where she gets the ideas for new topics, and why she has to be super picky when choosing which brands she’ll allow to sponsor her show.

Just about everyone’s experienced a scenario like this: you read a highly-nuanced article on a topic you find interesting. You then decide to share it on Facebook. Within minutes, a Facebook friend leaves a comment arguing with the premise of the article, and it’s immediately obvious that this person hasn’t actually read the piece in question. In fact, the vast majority of social media users will interact with content without actually clicking through and consuming it. One study from Columbia University found that 59 percent of links shared on social media aren’t even clicked on. Data collected from Hubspot found that “there is no correlation between retweets and clicks.” So what does this really mean for how we absorb information on social media? And how are we impacted by the commentary that social media users will often add when they’re sharing a link?York College political science professor Nick Anspach wanted to answer these questions, so he devised an experiment to find out what information is retained when social media users see a post but don’t click through to the source article. I interviewed Anspach about his results and whether social media has generated a net negative effect on how we monitor current events.

Sam Parr never set out to launch a media company. A few years ago, he was fresh from selling a company he had founded and was looking for something else to do. He decided to recruit about a dozen entrepreneurs as speakers and hosted an event he called Hustlecon. The event was a success, and Parr expanded it into a media website that published daily content. But while the site generated some viral hits, Parr eventually became convinced that the email inbox would produce a much more intimate experience and a better delivery system, so he relaunched The Hustle as a standalone newsletter. Since then, The Hustle has amassed a growing number of diehard followers who evangelize the newsletter to their friends, converse in a private Facebook group, and even meet up in person. I interviewed Parr about what strategies he used to grow the subscriber base, how his editorial team goes about picking daily topics, and what kind of companies like to advertise on a newsletter.

While it seems like every publisher, from The New York Times to Vox, is making significant investments in podcasting, one could argue that Slate was the earliest to invest in the medium. It launched the Slate Political Gabfest -- a panel show with three regular hosts -- all the way back in 2005. Since then, Slate has debuted dozens of new podcasts, which collectively generate millions of downloads each month. And starting in 2009, shortly after President Barack Obama’s inauguration, it started hosting live events centered around these podcasts. Slate has since expanded its live events business, and it now hosts sold-out shows in cities all across the U.S. I recently sat down with Faith Smith, the executive producer for Slate Live. We discussed how her team selects which cities to tour in, how she negotiates with event venues, and what podcast fans are willing to pay in order to watch a live podcast recording.

Chris Grady didn’t know much about the webcomic world when he launched Lunarbaboon, a semi-autobiographical comic about family and parenthood. But shortly after launching the comic, he started sharing it to Reddit, and suddenly Lunarbaboon was being seen and shared by tens of thousands of people. Flash forward a few years, and Lunarbaboon has over a million followers on Facebook. Grady generates $1,500 a month on Patreon and has launched several successful Kickstarter projects related to his comic. His latest Kickstarter, this one for a board game he helped illustrate and create, has already generated $50,000 in backing. I interviewed Grady about what it takes to maintain a successful webcomic, how he grew his audience, and why popular webcomics often make much more money from merchandise than they do from ads.

Would you read a 1,300-word newsletter about garden sheds? What about a 1,400-word piece on lettuce? A little over a year ago, the business-focused publication Quartz made a bet that you would, launching a daily newsletter called Quartz Obsession. The aim of the product? Take the most mundane topics imaginable and -- through narration, numbers, and quotes -- prove to the reader that these topics are not mundane at all. Unlike many publication newsletters that simply round up links to articles on the publication’s site, Quartz Obsession is a standalone newsletter that can be completely consumed within the inbox. It’s seen open rates as high as 80 percent and thousands of readers have written in to suggest topics. Why did Quartz launch a product that steered clear of the editorial topics it usually covers on its website? And how does it pick each day’s topics? To answer these questions, I turned to Jessanne Collins, who edits the newsletter.

Recently, an industry website called The Drum reported that The Financial Times, the London-based business publication, is projected to hit 1 million paying digital subscribers by next year. This is impressive, not just because only a handful of publications have hit this milestone, but also because The Financial Times has done so while maintaining a hard paywall. Unlike companies that use metered paywalls like The New York Times and Washington Post,  The Financial Times hits users with a subscriber login page on the vast majority of its articles. This presents a challenge for a social media editor: how do you promote content when most of your followers won’t be able to see it? To get an overview of The Financial Times’ social media strategy, I interviewed Jake Grovum, its head of social. He told me about how the Times’ has leveraged Instagram stories, what metrics his team is judged by, and why the newspaper hasn’t invested resources into Snapchat.

Long before Facebook started generating billions of dollars on self-service native ads, Henry Copeland had invented a self-service native advertising platform for blogs. And he was building early content management systems for newspapers well before products like Wordpress would go on to power much of the internet. These days, Copeland is focused on augmented reality, and he think that today’s AR products are the equivalent of the blog advertising widgets he was developing in the early 2000s. In other words, we haven’t even hit the tipping point that will make AR ubiquitous, woven into the fabric of our daily lives. What will that world look like? And what technologies still need to be invented before we can reach that point? I asked Copeland about these topics, and given his previous track record of spotting trends that would go on to sprout multi-billion dollar industries, I think we should listen to what he has to say.