The Business of Content with Simon Owens

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 businesses utilize Twitter. Recent guests have worked for Dungeons and Dragons, Grindr, and Dropbox. I recently interviewed Wadlington about his podcast strategy and the role the show plays in helping improve Twitter's bottom line.

Where you can subscribe to my newsletter: https://simonowens.substack.com/p/discount 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 spending more time on it. During a good month, I might put out a new episode each week, but I've had busy months where I was lucky if I could produce more than a single episode. If I can start making money from this podcast, then it'll be easier for me to justify spending more time on it, and then everyone gets to benefit. And I didn't want to do just a quick promo and then be done with it. Given that most of my listeners actually care about business models for content, I wanted to go deep on my decision making process, and to do that I enlisted the help of my friend Jaclyn Schiff. Jaclyn is a content expert like me who specializes in converting podcast episodes into shareable articles for clients. You can find her work at podreacher.com. She recently interviewed me about my history covering the business of content and how I came up with my monetization strategy.

There are few people as knowledgeable about web publishing as Scott Rosenberg. In 1995, he and a group of other San Francisco Examiner journalists launched Salon.com, one of the first online magazines. An early blogger, he wrote the definitive history of the blogosphere and published it as a book in 2009. Today, Rosenberg is the tech editor for Axios, a website launched in 2017 by Politico founders Mike Allen and Jim VandeHei. Since its debut, Axios has tried to upend the paradigm for how news can be delivered. Instead of adhering to the structure of the traditional news article, Axios reporters strive for succinctness by delivering information in a bulleted, just-the-facts-ma'am form. As co-founder Jim VandeHei explained in a 2017 interview, "Ninety percent of stories either shouldn't have been written or should have been 10 percent the length. Most people do not want to spend five minutes on 1500 words of mediocrity on something that has one interesting fact, figure or quote." In my interview with Scott Rosenberg, he told me about Salon's first viral story and explained why the online magazine was way ahead of its time, in both the way it delivered news and how it monetized content. We also discussed Axios's approach to news gathering and whether it's "Be smart" tagline is patronizing or enlightening.

In 2020, Netflix is projected to spend $17 billion on content. Disney will spend $24 billion and AT&T will shell out over $14 billion. With all that money on the line, there's an enormous amount of demand for new intellectual property that can be adapted into movies and TV shows, and a lot of that IP is being drawn directly from magazines. The Oscar-winning film Argo, for instance, is based on a 2007 Wired article, and the critically-acclaimed Netflix miniseries Unbelievable is based on a longform Propublica article published in 2015. This rising demand means that Hollywood is throwing larger and larger sums of money at journalists just to option their articles. All that money has had a distorting effect on the entire magazine industry, with writers increasingly pitching more narrative articles in the hopes of luring a Hollywood agent. At least that's according to journalist James Pogue, who recently wrote a piece for the Baffler about what he sees as the negative impact of the streaming wars on magazine journalism. I recently interviewed Pogue about this phenomenon and why he thinks it's changing longform reporting for the worse.

Of all the algorithms that influence our daily internet browsing habits, few are more closely scrutinized than the one that governs YouTube. Through the homepage, the recommendations that appear on the side of videos, and the trending tab, YouTube's algorithm has the ability to shower a video with millions of views and transform its unknown users into overnight stars. It's because of this very influence that so many people get angry about it. Whether it's YouTube stars who are worried about their ability to reach their fans or liberal critics who say YouTube promotes right-wing extremism, there are plenty of politicians, journalists, and activists who are up in arms and ready to accuse YouTube executives of all sorts of nefarious evil. But how many of these accusations are merely conspiracy theories born out of paranoia? To answer that question, I interviewed Chris Stokel-Walker, a journalist who covers YouTube for an online magazine called Fast Forward. Stokel-Walker and I went deep on the YouTube algorithm and the ways its biggest stars game it to their benefit.

I think it's safe to say at this point that digital publishers recognize the importance of email newsletters. In 2016, Facebook pulled the rug out from underneath a media industry that had, until then, relied on it for hockey stick growth, and over the next several years publishers generally warmed to the idea that the decentralized distribution offered by email newsletters would prove more reliable than the fickle whims of social media giants. Today, nearly every media company has a robust email marketing strategy, and some news startups interact with their readerships almost entirely within the inbox. We've also seen the launch of platforms that make it easier for individual writers to distribute their own newsletters and monetize them through paid subscriptions. So are newsletters reaching a saturation point? Are they generating real ad revenue? And can newsletters actually replace Facebook as a referral source? These are just some of the questions I put toward Ernie Smith, the creator and editor of Tedium, a fantastic newsletter that almost operates as a kind of Wikipedia of obscure topics. Smith also runs a popular Facebook group for the newsletter industry, and he's one of the most knowledgeable people I know when it comes to newsletter trends.

Back in 2010, the world was still skeptical of Wikipedia. High school teachers and college professors warned students to never, ever use it for research. If you ever tried to cite it in an argument, your opponent would mock it as unreliable. Late night hosts like Stephen Colbert would enlist their audiences to flood a specific Wikipedia page and vandalize it. Celebrities and major companies would treat it as a vanity project, editing their own pages while making absolutely no effort to disclose their conflict of interest. Flash forward to 2020, and Wikipedia certainly has more respect. The Wikimedia Foundation, which acts as its official steward, has tens of millions of dollars in the bank. While college professors don't view it as a primary source for research, they'll sometimes endorse it as a starting point for said research. And nearly everyone recognizes it as one of the most influential websites on the internet. But though tens of millions of people use Wikipedia every day, most only have a passing understanding of how a core group of a few thousand volunteer editors perform the vast majority of contributions to its articles. One of those editors is Bill Beutler. For the past decade, Bill has consulted with hundreds of brands, helping them to edit their Wikipedia pages without running afoul of the platform's strict rules. I recently interviewed Bill about the problems that have plagued Wikipedia for the past decade and the issues its community will need to address in the decade to come.

Back in June, the Interactive Advertising Bureau released a report estimating that the podcast industry generated $479 million in 2018 and is projected to make $1 billion by 2021. Not only is this a tiny pittance compared to the money generated by other mediums like TV and search, but podcasting has also been limited by its over-reliance on advertising. Unlike, say, Netflix or The New York Times, most podcast companies have struggled to diversify their revenue beyond advertising, and most major podcast apps don't provide a way for podcasters to directly collect money from their listeners. But several companies, like Spotify and Luminary, are attempting to bundle exclusive podcasts and sell access to them behind a subscription paywall. Other platforms assist individual podcasters in converting their listeners into paying subscribers. The company Glow fits into the latter category. Founded a little over a year ago, Glow developed technology that allows a podcast's paying subscribers to listen to paywalled episodes on their podcast player of choice. I recently interviewed its co-founder Amira Valliani about how she's solving the paywall problem and why she thinks paid podcast subscriptions will eventually scale.

In November, a company called Minute Media announced it was acquiring The Players' Tribune, the website founded by Derek Jeter that regularly collaborates with pro sports athletes on first-person storytelling. Though the name Minute Media might not be familiar to most people, chances are you've encountered one of the sites it owns, especially if you follow sports. Over the past few years, it's slowly amassed an amalgam of sports properties that cover everything from global soccer to esports. It also owns Mental Floss, the quirky trivia magazine that was founded in 2001. I recently sat down with President and CRO Rich Routman to discuss why he thinks Minute Media is different from many of the other venture funded digital media sites out there. We talked about the company's video strategy, how it approaches advertising, and why it expanded into non-sports content when it acquired Mental Floss.

More than a decade ago, before most people even knew what a podcast was, Macmillan, one of the largest book publishers in the world, launched a podcast network. Called Quick and Dirty Tips, the network consisted of short, scripted podcasts that delivered evergreen, practical advice on a range of topics from grammar to money management. In the years since, Macmillan has continued to invest in its podcast division, expanding into narrative shows and even teleplays. For this episode, I interviewed Kathy Doyle, vice president of podcasting, about where the company has seen the most success and how podcasting allowed it to diversify its revenue.

Jane Friedman has spent almost the entirety of her professional career working in book publishing. In the mid-aughts, she began writing about the industry, both for professional outlets and her own blog. A few years ago, she launched a paid newsletter that now generates the majority of her income. I recently interviewed Friedman about her work. We discussed how she grew her newsletter into a sustainable business, and then we talked about the current state of book publishing. One aspect of this world that's long fascinated me is self-publishing, so I asked Friedman to fill me in on how this market is maturing and where self-published writers are seeing success.

If you listen to the podcast called Startup, then you've heard host Alex Blumberg go into exquisite detail about the trials and tribulations of launching a VC-funded podcast network. In earlier seasons, we got a firsthand look about what it was like to pitch venture capitalists, hire talent, and grow the business. In the final season of Startup, Blumberg walked us through Spotify's $230 million acquisition of Gimlet. But what about bootstrapped podcast networks that don't have access to millions of dollars of venture capital money? How do they get off the ground and scale? To answer these questions, I spoke to Jeff Umbro, the founder of the Podglomerate. We talked about his early mistakes in trying to partner with shows for his network and why it can be incredibly difficult to monetize a show with a small audience.

Advance Publications is one of the largest media companies in the world. It owns dozens of newspapers, the Conde Nast magazine empire, and even Reddit. A few years ago, it launched the Alpha Group, a tech incubator that would launch small startups and try to grow them into thriving, standalone businesses. One of those startups was called The Tylt, a platform that allows its users to participate in online opinion polls on a wide range of issues. The Tylt was successful enough that Alpha Group spun it off as its own company. Recently, The Tylt hired Selena Roberts, a seasoned journalist who's written for The New York Times and Sports Illustrated, to serve as its executive editor. I recently sat down with Roberts to learn about the site's editorial ambitions and whether online, unscientific polls have any journalistic value.

Agnes Kozera knows a thing or two about helping content creators monetize their content. In 2013, she and a co-founder launched Famebit, a platform that helped YouTubers match with brands that were willing to sponsor their videos. The company was so successful that it was eventually acquired by YouTube in 2016. This year, Kozera and that same co-founder are launching Podcorn, a platform designed to help podcasters monetize their shows. Like Famebit, it will serve as an online marketplace where brands can post RFPs for projects and be matched with participating podcasters. I interviewed Kozera about why such a platform is needed, how the current podcast advertising landscape is flawed, and why podcasters with small-to-mid-sized audiences currently have such a difficult time finding sponsors.

Clive Thompson has the kind of career that most writers would envy. He's written two books for major publishing houses. He has a monthly column at Wired magazine. And he writes regular features for The New York Times Magazine and other glossy magazines. But that kind of success didn't come to him overnight. In fact, Thompson spent years toiling away writing for small publications making very little money. I recently interviewed him to discuss how he made his big break, what it takes to write the perfect magazine pitch, and why book publishers are more likely to award contracts to established journalists.

These days, nearly every major news organization employs multiple reporters who aggressively cover the tech industry, but a decade ago tech coverage was dominated by blogs like TechCrunch, Mashable, and VentureBeat. Back then, these blogs churned out scoop after scoop, competed for traffic, and sometimes even went to war with each other. Among the earliest of these blogs was ReadWriteWeb. Launched in 2003, it was founded by Richard MacManus, a New Zealander who was inspired to launch a site after reading the work of blog pioneer Dave Winer. Within a few years, MacManus began selling ads and was able to hire a global staff of reporters. I recently interviewed MacManus about the early days of tech blogging and why, for his latest writing project, he decided to eschew blogging entirely and launch a newsletter instead.

In 2005, a computer software engineer named Gabe Rivera launched the site that would eventually become Techmeme. Governed by algorithms, Techmeme aggregated the day's tech news, and it eventually became so influential that bloggers and journalists would vie to get their articles featured on the site. Flash forward to 2018, and Techmeme announced that it would expand its news curation into a daily podcast. I recently sat down with host Brian McCullough to talk about how he came up with the idea for a daily tech podcast and what he's doing to expand it into an entire podcast network.

The last decade hasn't been kind to local newspapers. According to one study, 1,800 newspapers have shut down since 2004, and many of those that survived are facing tighter margins, layoffs, and corporate consolidation. There are myriad reasons for this retrenchment. Part of the blame is on hedge funds that buy up local media companies and then squeeze them dry. Others point to major platforms like Facebook, Google, and Craigslist, all of which have siphoned away a large portion of the local advertising newspapers traditionally relied on. Despite these headwinds, we've seen a few digital-first upstarts thrive in the local news market. One such company is Village Media, which started out as a single news site in an Ontario city and has since grown to 11 sites spread out across Canada. I recently interviewed Jeff Elgie, Village Media's CEO, about the company's history and how it's succeeded where so many legacy newspapers have struggled or failed.

The Interactive Advertising Bureau recently estimated that podcast industry revenue grew by 53 percent last year and is projected to reach $1 billion by 2021. With so much year-over-year growth, it shouldn't be any surprise that many media companies are aggressively expanding their podcast operations. This is certainly true for Vox Media, which over the past few years has launched over 150 podcasts on topics that include technology, politics, and sports. The audio medium is now an eight-figure business for Vox. I recently sat down with Marty Moe, the head of Vox Media Studios, to talk about how the company is monetizing these podcasts, what he thinks about Spotify's entry into podcasting, and why he thinks he can grow Vox's podcast revenue from eight to nine figures.

Back in 2011, LinkedIn announced that it was hiring Dan Roth, who was then the editor of Fortune.com, to serve as its editor in chief. Given LinkedIn's then role as mostly a repository for online resumes, the move had many scratching their heads. Over the next few years, though, Roth's team would roll out a number of editorial products. It started by curating outside news sources, sending LinkedIn users to articles published by business publications like The Wall Street Journal and Business Insider. Then it rolled out a blogging platform that was only available to influential users like Richard Branson and Bill Gates. Eventually, it then opened up its blogging platform to all users. During all this time, LinkedIn was steadily hiring journalists from some of the world's top business publications, including The Wall Street Journal, Forbes, and Fortune. Today, it has an editorial staff of 60, and these editors are responsible for everything from curating user content to producing their own original reporting.I recently sat down with Linkedin senior editor at large Isabelle Roughol. I asked her about how LinkedIn editors go about curating content, how they distribute this content on LinkedIn, and how they approach original reporting projects.

For a few years, Ben Cohen was living the dream. His political opinion site, The Daily Banter, was growing in leaps and bounds, generating enough traffic and ad revenue to support several full-time writers. At its height, the site was getting upwards of 6 million unique visitors a month, fueled in large part by readers sharing his content on Facebook. But you probably know what happened next. In January 2018, Mark Zuckerberg announced that Facebook was pivoting away from news, and that publishers would see a decline in exposure in the Newsfeed. Virtually overnight, Cohen saw his Facebook traffic drop by 90%. He tried to hold out as long as he could, but eventually Cohen reached a point where he either had to radically change his business model or shut down the website completely. In the end, he did both. He shut down his website and launched a newsletter. Sign up, and you received two free newsletters a week. Pay a little extra, and you got two additional newsletters. I recently interviewed Cohen about what went into his decision to pivot and how his readership responded to the announcement.

With social platforms like Facebook throttling distribution for news and the online ad market collapsing, more and more writers are turning to paid newsletters as a way to make a living. In a November 2018 episode of this podcast, I interviewed Hamish McKenzie, the co-founder of Substack, a platform that made it easy for writers to launch newsletters and charge subscribers to receive exclusive issues of those newsletters. At the time, McKenzie said that Substack writers had converted a combined 25,000 readers into paying subscribers. Flash forward to today, and that number is up to 40,000. In fact, BuzzFeed recently reported that the 12 top writers on Substack make over $160,000 a year each. For this week's episode, I interviewed one of those writers: Robert Cottrell. Ten years ago, Cottrell founded a website called The Browser. He would comb through thousands of articles a day and pick the five he found most interesting, adding a dash of commentary to go along with each pick. As time wore on, he began to notice that many of his readers were signing up for an email digest of his daily recommendations. In 2013, he launched a paid version of the newsletter, and in the intervening years it's grown to over 10,000 subscribers. I interviewed Cottrell about how he goes about choosing articles every day, what his longterm ambitions are for the newsletter, and why he recently hired a CEO.

It seems like not a week goes by without another online publisher announcing a subscription paywall, but that didn't make me any less surprised when Business Insider debuted its own paid subscription product. Founded in 2007 by Henry Blodget, Business Insider took boring, staid business reporting and curated it with a bloggy, conversational voice. Funded by digital advertising, BI tested the theory that a digital media company could scale its way to profitability with free content. But in 2015, Business Insider was acquired by Axel Springer, a German media company that fiercely protects its intellectual property and is a firm believer that consumers should pay for content. In 2017, Business Insider launched Prime, a subscription product which places some of this site's daily reporting behind a paywall. Though it still publishes plenty of free content, you'll have to cough up around $10 a month if you want to access its most deeply-reported articles. To get insights into Business Insider's paywall strategy, I interviewed Claudius Senst, its head of consumer subscriptions. I asked him how editors decide whether to place an article behind the paywall, what converts readers into paying subscribers, and why Business Insider didn't follow in the footsteps of The Washington Post and New York Times by launching a metered paywall.

If you've been working in local news over the past decade, chances are that your job hasn't felt very secure. One study estimated that as many 1,800 local newspapers have shut down since 2004, and those that have survived have faced steep budget cuts and layoffs. Hedge funds have been purchasing newspapers, saddling them with debt, and bleeding them dry, while the Facebook/Google duopoly have diverted more and more local advertising toward their own services. Last year, Facebook launched a feature that would allow users to be shown more local news in their Newsfeed, but it recently admitted that one in three U.S. users lived in areas that didn't produce enough local news for Facebook to curate. But not all local news operations have struggled. A New Jersey based media company called TAPinto has launched 81 local news sites and is still growing. While most of those sites are located in New Jersey, the company has recently branched out into Pennsylvania, South Carolina, and Florida. I recently interviewed Mike Shapiro, TAPinto's founder, and asked him about why his model seems to be working. We also discussed other failed local news projects and whether Facebook's efforts to boost local news are actually working. To see my previous interview with Shapiro, go here: https://bit.ly/2Wdvhl4

Back in January, I wrote an article for New York magazine asking whether it's time for the U.S. government to enact stricter regulation on social media influencers. I pointed to investigations from news outlets like The New York Times that uncovered companies that have sold hundreds of millions of fake followers to willing buyers, most of whom wanted to inflate their online influence. In many cases, these fake followings were then used to dupe unsuspecting brands into purchasing sponsored Instagram posts. The rising prevalence of fraud within the Instagram influencer community has led to greater scrutiny and efforts to detect such fraud. To do so, brands now often use software like HypeAuditor, which scans an influencer's account in search of automated and fraudulent activity. HypeAuditor recently leveraged its data to generate a report on the current state of Instagram influencer fraud. I interviewed Yaro Pat, HypeAuditor's product owner, about the results of the report and how Instagram fraudsters are getting more sophisticated in how they game the Instagram algorithm.

John Yedinak didn't have a traditional journalism background when he started his media company. He was working in the mortgage industry when he read an interview with TechCrunch founder Michael Arrington. The interview inspired him to launch his own blog on the reverse mortgage industry, and as the blog's audience grew, he began to realize that there was a massive market out there for niche, B2B publications. In 2012, he officially launched the Aging Media Network, a constellation of sites that cover the businesses that service the aging population, from hospice care to senior housing. I recently sat down with Yedinak to talk about how his team built the audience for the publications, how they monetize the sites, and why they focus on advertising instead of paid subscriptions.

Peruse through the vast video archive at The New York Times, and you'll come across plenty of your standard short documentary films, the kinds with voiceover, b-roll footage, and original interviews. But you'll also encounter some experimental fare. There's the fake infomercial advertising a phone hotline for racists. There's an entire animated series geared toward parents. And then there's the ongoing series, called Diary of a Song, which uses a mixture of low quality Skype footage and animation to walk the viewer through how a hit song was made. Overseeing much of this production is Nancy Gauss, executive director of video at The New York Times. I recently interviewed Gauss about her team's approach to video creation and how it fits in with The Times's larger goals in driving brand loyalty and paid subscriptions.

Advance Publications is one of the world's largest media companies. It owns Conde Nast, home to magazines like The New Yorker and Vogue, as well as dozens of newspapers across the U.S. It even has a majority stake in Reddit. A few years ago, it launched Alpha Group, an incubator meant to launch brand new tech products and grow them into fully functional companies. Rather than acting like a traditional media company, Alpha Group takes a much more expansive view as to what constitutes a 21-century media company, and its products span a wide range of functions, from a social polling app to a Facebook chat bot. I sat down with David Cohn, a senior director at Alpha Group, to talk about how the company comes up with new product ideas and what it's like to try to launch multiple tech companies from scratch.

Founded in 1998, MoveOn.org started as a progressive email group and pioneered political online advocacy. Over the past two decades it's leveraged its massive email list to raise millions of dollars for left-wing candidates and push for a number of progressive legislative issues. As the internet evolved, so did MoveOn, and today its reach spans millions of followers across the web's biggest social platforms. In recent years, it's placed significant emphasis on creating online video, and its videos now generate millions of views each week across Facebook, Instagram, and Twitter. I recently sat down with Sara Kenigsberg, MoveOn's senior video producer. I asked about why MoveOn's videos aren't designed well for YouTube, how she chooses her video topics, and which social platform is best for broadcasting live video.

It started in 2009 in San Francisco. A couple of journalists got the idea of putting together a magazine, but instead of setting it to print, they would perform it live. Pop-Up Magazine, as the event was called, was a huge hit, and the founders had to seek out larger and larger theaters in order to meet demand. In 2015, they decided to take the show on the road, touring Pop-Up Magazine across several major cities. I recently sat down with Chas Edwards, co-founder and president of Pop-Up Magazine. I asked him about the logistics of creating a live magazine from scratch, how the company makes money, and what the future holds for it now that it's been purchased by the Emerson Collective.

The Atlantic may be a 160-year-old institution, but it isn't shy about experimenting with new things. It was one of the first traditional publications to go all-in on digital media in the late-aughts and managed to achieve profitability from the move pretty quickly. It experimented with brand new verticals like The Atlantic Wire and Quartz. Recently, it was acquired by Laurene Powell Jobs's Emerson Collective, which has been investing in forward-thinking media sites. And since 2012, it's been running an in-house creative agency called Atlantic 57. The idea is simple: let's take the editorial insights we've gleaned from running a magazine for 160 years and use that to launch online publications for major brands and non-profits. I recently interview Margaret Myers, a longtime journalist who works on one of these editorial projects for insurance company Allstate. I asked her about her past life as a traditional journalist and how she leverages that expertise in developing content for The Renewal Project, the online publication she manages for Allstate.

When Ben Collins launched his blog about Google Sheets, which is basically Google's version of Excel, he didn't intend for it to become a full-time business. He was just documenting his learning process and hoped the blog would serve as an online portfolio for when he went out to seek full-time employment. But he was surprised to learn that there was an actual audience for his blog posts, and within six months he had thousands of visitors flooding his website searching for how to perform specific actions within Google Sheets. Eventually, this led to his first paying client, and before he knew it Collins had more incoming business than he knew what to do with. But he wanted to create something a little more scalable, so he started developing an online course for those looking to master the Google Sheets platform. Within months of launching this course, he was generating thousands of dollars a month in passive income. I interviewed Collins about how he designed his course, how he marketed it, and how he decided on how to price it.

In 2017, The Wall Street Journal published an op-ed titled "How Antitrust Undermines Press Freedom." It was written by David Chavern, the head of the News Media Alliance, a trade group that represents over 2,000 publishers. In it, he argues that Facebook and Google have effectively cornered the digital ad market, eating up all its growth, and that this has come at the expense of the very content creators that these two companies rely on, content creators Facebook and Google refuse to fairly compensate. "The only way publishers can address this inexorable threat is by banding together," wrote Chavern. "If they open a unified front to negotiate with Google and Facebook—pushing for stronger intellectual-property protections, better support for subscription models and a fair share of revenue and data—they could build a more sustainable future for the news business." Earlier this decade, several book publishers banned together to negotiate ebook prices with Apple in a direct effort to undermine Amazon's command of the market, and they were slapped with a lawsuit from the Department of Justice for violating antitrust laws, hence why the News Media Alliance is seeking a special exemption. But do publishers deserve one? And even if they do, would they be able to get such legislation passed through such a divided Congress? These are the questions I asked David Chavern for this week's episode.

Name just about any media beat, and you'll find plenty of people trying to predict the future. Political pundits argue over who will win the next election. Finance journalists report on economic forecasts and claims from analysts over where a stock will be six months from now. Even entertainment bloggers will try to hash out which film, song, or TV show will win at the next awards ceremony. But in most cases, those predictions will be wrong. In fact, many studies have shown that a crowd of everyday people will, on average, make better predictions than the experts who work in that particular field. That's why a lot of attention has been paid lately to betting markets, which can provide real-time odds for any particular outcome ranging from a presidential election to winner of the best picture Oscar. There's just one problem: most states outlaw online gambling, meaning many of the most well-known betting markets don't operate within the U.S. But a relatively new prediction market app, called Futuur, gets around this hurdle by using fictional currency. I interviewed Tom Bennett, the founder of Futuur, about how his app works and how its predictions matched up against those made by other famous forecasters like FiveThirtyEight.

Subscriptions are all the rage in the media industry right now. Facing diminishing ad rates, publishers have turned to the paid subscription model as a way to draw revenue directly from the users that consume their content. Publishers ranging from The New York Times to The Washington Post to The Financial Times have announced they've reached north of a million subscribers. It seems like every day a different publisher is announcing the launch of a metered paywall or membership service. But getting a news consumer to actually open up their wallet and subscribe is harder than it looks, and the space is only getting more competitive as publishers continue to launch subscription offerings. So what are the actions a publisher can take to make it more likely for a casual reader to convert into a paying subscriber? A new study from digital publishing platform Twipe sought to answer this question. Researcher Mary-Katharine Phillips surveyed 4,000 news consumers across Europe and the U.S. to gain a better understanding of how they consume the news and what drives their news diet. I interviewed Phillips about what percentage of news consumers are willing to pay for digital news, what drives them to subscribe, and what kind of news formats they prefer.

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.

If you follow the digital media sector, you've likely noticed that advertising as a business model is on the wane. With the Facebook and Google duopoly sucking up just about all the advertising money flowing online, publishers have been forced to find alternate revenue sources to fund their content. One such source: subscriptions. More and more publishers are rolling out subscription and membership programs, and many have been successful. One such success? Innovation Leader, a small business-focused publication that launched in 2013. It carries no advertising, has a hard paywall, and charges subscribers $695 a year. I recently sat down with one of its cofounders, Scott Kirsner, and asked him about why he settled on such a high price point, how the publication markets to new subscribers, and how it approaches content development.

In 2010, a college dropout named Kyle Taylor launched a blogspot account. He was taking on odd side jobs in an attempt to crawl his way out of debt, and the blog was a way to write about lessons he learned on making and saving money. Traffic was scarce, at first, but over a period of years the blog slowly gained an audience. Eventually, brands started approaching Taylor about publishing sponsored posts, and revenue for the site, which was called The Penny Hoarder, quickly grew. Flash forward a few more years, and The Penny Hoarder now has a huge audience, dozens of full-time staffers, and millions in annual revenue. To get a better understanding of how the site grew this big, I interviewed John Schlander, The Penny Hoarder's managing editor. I asked him about how his staff develops its story ideas, how the site makes money, and whether the rise of the gig economy plays a part in its success. Let's jump right into it.

When Christopher Wink graduated college in 2008, he had no intention of launching a media company. He just wanted an entry level journalism job that would allow him to work his way up within the industry. But back then, when newspapers were hemorrhaging revenue and announcing mass layoffs, there weren't a lot of journalism jobs to pass around. So, out of desperation, he and a couple other college friends launched a Wordpress blog called Technically Philly. It covered the local tech scene, an industry that at the time was largely ignored by regional news organizations. Eventually, the blog gained traction and profitability, and the growth allowed Wink and his friends to launch local tech blogs in Brooklyn, Baltimore, DC, and Delaware. I interviewed Wink about the early days of running an unknown tech blog, what it takes to launch a site in a new city, and why he's never been all that interested in building out an advertising business.

Back in January, Facebook made an announcement that shocked the publishing world: It was tweaking its Newsfeed algorithm so there would be less emphasis on Facebook pages and more focus on what your friends were sharing. Reach for Facebook pages was expected to plummet, and publishers that had grown addicted to Facebook's free referral traffic girded themselves for an all-out decimation of their businesses. But while there have been some clear victims of the algorithm change, the actual data for who's been hurt by it is noisy. Some publishers have seen a dip in Facebook engagement, while others have remained steady or even improved. That's the case for U.S. publishers, at least. But what about Europe? To find out, I interviewed Steve El-Sharawy, head of innovation at EzyInsights, a platform that tracks Facebook engagement for publishers. I asked El-Sharawy about how European publishers reacted to the announced algorithm changes and whether there are any clear winners and losers in the ordeal.

It's impossible to know which company launched the first branded podcast, but one of the earliest well known examples was GE's The Message. Produced in collaboration with Panoply, The Message was a science fiction documentary that generated millions of downloads and a rabid fanbase. Ever since GE's runaway success with the medium, other major brands have waded into the podcast waters, with large companies like Walmart and Goldman Sachs launching their own shows in recent years. But what makes a branded podcast good? How do you avoid making it sound like just another ad? And how does a successful podcast help a company's bottom line? To answer these questions, I interviewed Rachael King, founder of the podcast consulting company Pod People. She recently helped produce podcasts for companies like Samsung and Medium, and we talked about the rise in demand for the services she offers and how one develops the skillset needed to become a podcast consultant.