The Long Story with Simon Owens (Simon Owens)

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.

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.

Visit https://theygotacquired.com/newsletter

When everyday people hear about space-related news, it’s usually in association with an organization like NASA or SpaceX. But while Elon Musk is great at grabbing headlines, the space industry actually comprises a vast constellation of companies that generate hundreds of billions of dollars a year. And it’s only set to expand; Morgan Stanley projects it’ll reach $1.25 trillion by 2040.

Given the size and growth of this industry, it’s probably a surprise to no one who listens to this podcast that there’s an enormous opportunity for the B2B media outlets that cover it. One of the most exciting entrants into that space is Payload, a daily newsletter that launched in 2021.

Though Payload was bootstrapped for its first several months, it announced a $650,000 seed round last year that was led by Winklevoss Capital, the venture firm run by Cameron and Tyler Winklevoss. It’s since hired an editorial staff and landed its first major sponsors.

Payload was founded by Mo Islam and Ari Lewis, and in December 2021 I interviewed Mo about the newsletter’s origin, its audience development strategy, and its plans to monetize its influential readership.

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.

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.

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.

As a CBS reporter in Los Angeles, Erica Mandy had a thriving career ahead of her in TV news. But in 2017 she quit her job and launched her own daily news podcast. It’s called The Newsworthy, and every morning it gives listeners a 12-minute rundown of the most important headlines. It also delivers weekend longform interviews with newsmakers. After four years in operation, it now generates over 800,000 downloads per month and has a growing team.

I spoke to Erica about why she made the jump from TV to podcasts, how she found her audience, and whether the daily news podcast space is becoming saturated.

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.

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.

Let’s say you have a pile of money you’re sitting on and you want to invest it. If you decide to invest it in stocks, then it’s incredibly easy to track the value of your investment on a minute by minute basis. But what if you want to invest in a less-regulated asset class like, say baseball cards or art? How do you even begin to assess the price of these assets, both before and after you’ve purchased them?

You’d probably turn to a guy like Stefan von Imhof. For the past few years, he and a co-founder have been running a newsletter focused on alternative investments. Its weekly installments go deep on various investment categories ranging from limited edition books to water rights, and it now reaches over 85,000 subscribers.

The newsletter is not only monetized through the traditional models, but it also launched a fund for accredited investors, and Stefan’s team has deployed millions of dollars across several asset classes.

In my interview with Stefan, we talked about how he got interested in alternative investments, the steps to launching a fund, and his strategy for acquiring other newsletters.

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Pat Walls’s most successful startup to date was born in the wake of a previous failed startup. Back in 2016 he and a couple other co-founders had been operating a B2B SaaS platform, but after it struggled to gain traction, they were forced to shut it down.

But Pat never lost the entrepreneurship itch, and in 2017 he started interviewing other startup founders on the phone and converting those interviews into case studies for a website called Starter Story. After a few of those case studies blew up on Reddit, Pat knew he was onto something, so he started publishing them with more frequency.

Flash forward a few years, and Starter Story now attracts over a million visitors a month, many from Google Searches. It also generates half a million dollars in annual revenue through a mixture of advertising, membership, and affiliate marketing.

It used to be if you wanted to break into broadcast media you first had to start small – by getting a job as a correspondent at a local news station and then working your way up to bigger and bigger markets.

That’s the career trajectory that Casey Keirnan followed. He started out covering high school sports in small towns and then eventually landed a job at CBS Interactive, which was trying to create an ESPN competitor for OTT streaming. But after only two years on the job, Casey’s contract wasn’t renewed, and he feared he would have to go back to local news.

But then he launched A.M. Hoops, an NBA-focused YouTube channel that ended up being so successful that he replaced his previous salary within a few months. Today, it boasts over 400,000 subscribers and 264 million channel views.

In our interview, Casey told me about his slow climb in local news, why he struggled at his CBS job, and what inspired him to strike off on his own to start a YouTube channel.

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When people sign up for the Alts.co newsletter, they’re looking to read its deep dives into alternative investments like art, baseball cards, and rare books. But the most serious investors in its audience want access to actual deal flow, and to gain that access they sign up for Altea, a high-priced membership community that actually vets potential deals and allows them to invest. Not only does Alts.co generate revenue through the annual membership, but it also charges for management fees and carried interest. In essence, Alts.co is a media company that monetizes via an investment firm.

In a recent interview, co-founder Stefan von Imhof explained why his company settled on this model, how it sources deals, and why he eventually wants to stop selling sponsorships within the newsletter.

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.

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.

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I’m sure just about everybody has had the experience of looking at a celebrity memoir and wondering: did they actually write that? In many cases, they didn’t, at least not by themselves. There’s actually an entire shadow economy of ghost writers who do the bulk of the work on these books – not just for celebrities, but all kinds of public figures ranging from big-name CEOs to politicians.

But how does one go about hiring a ghost writer? And what’s it like to work with one? To answer these questions, I turned to Dan Gerstein, the founder of Gotham Ghostwriters, an agency that specializes in connecting clients to professional ghostwriters.

Back in 2013, the Obama Administration rolled out a new version of Healthcare.gov, with disastrous results. It was the public unveiling of the Obamacare exchanges that would allow anyone to buy health insurance on the open market, and yet the website was almost impossible to navigate without encountering errors that would prevent you from signing up for insurance.

At the time, Charles Gaba was running a freelance web designer business in Michigan and writing for the liberal blog Daily Kos during his free time. Frustrated by the botched rollout and the amount of misinformation floating around about how many people had actually enrolled in the exchanges, he made a public call to other Daily Kos bloggers to help him count the number of Obamacare enrollees.

That project eventually evolved into ACAsignups.net, a standalone blog that eventually captured the attention of policymakers, journalists, and anyone interested in the state of U.S. healthcare. Traffic to his blog exploded, and he became an overnight celebrity in the healthcare space.

I interviewed Gaba about how he’s monetizing his website and the role he’s played in helping save Obamacare from GOP sabotage.

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.

Welcome to Night Vale. The Message. Steal the Stars. Homecoming. The Bright Sessions. All are fiction podcasts that have seen downloads in the millions. Some have been optioned for television or film adaptation. All were launched in just the last few years.

For much of the early to mid 20th century, millions of listeners tuned in each week to listen to radio dramas and fiction broadcasts in genres ranging from adventure (Superman) to science fiction (War of the Worlds) to crime noir (Dragnet).

But by the early 60s, due to the rise of television, the radio drama faded in popularity, and most were canceled by the end of 1962. Though some broadcasters continued to dabble in the medium, most people today have grown up without having listened to a single radio play.

Podcasting, however, has led to a resurgence in this kind of audio fiction, and a whole new generation of fans are tuning in to new episodes, attending live events, and ordering merchandise online.

Why are we seeing this resurgence in what was thought to be a bygone medium? To answer this, I interviewed Alasdair Stuart, the owner of Escape Artists Inc, which produces a number of popular fiction podcasts in the science fiction, fantasy, and horror genres.

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Mignon Fogarty isn’t just one of the world’s most popular podcasters, she’s also an incredibly innovative media entrepreneur. She launched her Grammar Girl podcast 18 years ago, and the success of that propelled her book onto the New York Times bestseller list. She also founded Quick & Dirty Tips, a media network she now runs in partnership with Macmillan Publishers.

To round out her media business even more, she’s launched around seven courses, all geared toward being a better communicator and writer. Thousands of customers have taken them, and they’ve opened her up to an entirely new customer base for her content.

In a recent interview, Mignon explained how she entered the courses market, what goes into putting together a course, and why she decided to partner with powerful distributors like LinkedIn Learning rather than create the courses by herself.

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.

Before William Knight launched Early Morning Media, he had worked for years at a company that specialized in sending press clippings to corporate clients. While these services were mostly utilized by a client’s internal communications team, William realized at some point that these same news curation practices would be appreciated by an external audience.

So in 2011, he launched B2B newsletters covering multiple industries. At first, these newsletters were monetized mostly through paid subscriptions, but as the company expanded he began to roll out free, ad-supported newsletters as well. Today, Early Morning Media operates over a dozen newsletters that are read by 500,000 industry professionals.

In our interview, William discussed the company’s origin story, its method for curating news, and the decision process for launching a new newsletter.

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.

For the past decade, publishers have utilized metered paywalls to grow their subscription businesses. Under that model, a reader gets to view a certain number of free articles before a paywall pops up and requires them to subscribe. 

But how many free articles should a user encounter before they hit a paywall?

Increasingly, the answer to that question is: It depends. Publishers are starting to roll out dynamic paywalls that assign varying weights to different kinds of stories. If you’re reading a business article, for instance, you may only get to read three free articles before hitting a paywall, but if you’re perusing real estate listings you might get unlimited free access.

The Globe and Mail has taken the idea of the dynamic paywall to the next level: it’s developed a sophisticated AI that’s able to analyze user behavior and determine the exact moment that a reader is most likely to subscribe. The AI is so powerful that the newspaper’s editors now allow it to automate the placement of stories on its homepage and social media.

I recently sat down with Gordon Edall, the person who runs the product team that developed the AI. We talked about how the paywall was initially designed, his experience recruiting data scientists, and why the Globe and Mail is licensing its AI product to other publishers.

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

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Lon Seidman doesn’t operate the largest gadget YouTube channel in the world, but he doesn’t need to in order to run a successful media business. That’s because he remains hyper focused on reviewing non-sexy products that sell in extremely high volumes. This has allowed him to build a highly lucrative affiliate business, not only on YouTube, but also on Amazon Video.

In a recent interview, Lon explained his methodology for picking products to review, how he optimizes his affiliate links, and why he’s spending more time posting his content to decentralized platforms.

When it comes to disruption, few industries have experienced as much upheaval over the past 20 years as the music industry. The lucrative CD era ended with the rise of Napster piracy, and the introduction of Apple’s iTunes did little to stem the losses, It’s only within the last decade, with the rise of streaming services like Spotify, that music revenue has begun to recover.

Jay Gilbert had a frontrow seat to all of this turmoil. Working for companies like Warner Music and Universal Music Group, he got to know just about every facet of the music-making process. Then in 2015, he struck off on his own and launched a consulting business. To help raise awareness of his services, he began writing a weekly newsletter called Your Morning Coffee. What started out as an email sent out to a few hundred friends eventually grew to 15,000 readers, and it’s now one of the most influential newsletters in the industry.

In my interview with Jay, we talked about how the newsletter found an audience, its contribution to his consulting business, and why he doesn’t want to scale it into a traditional media company.

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.

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.

When Jay Shabat launched his newsletter in 2004, he had absolutely no experience in journalism or in operating a media company. This was also long before the era when it became easy to distribute paid newsletters. But what Jay did have was a passionate fascination with the airline industry, and he leveraged that passion to build a loyal readership.

In our interview, we discussed how he found readers in a pre-social media age, his pricing strategy, and why he decided to sell the company in 2018.

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Like a lot of journalists in the mid-2000s, Tim Burrowes grew frustrated with his employer’s print mentality and its tendency to treat online publishing as an afterthought. At the time, he worked for an Australian trade magazine that covered that country’s media industry.

So in 2008, he and two co-founders decided to launch Mumbrella, a competing blog that published upwards of 15 times a day. Its gossipy comments section quickly attracted an audience of bored office workers, and within a few years it was hosting multiple industry events that collectively generated millions of dollars.

In a recent interview, Tim explained how Mumbrella made such a big splash so quickly, why he and his co-founders decided to sell it, and what he’s doing differently with his newest media startup. 

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It’s incredibly difficult to convert your audience from free readers/viewers/listeners into paying subscribers. In this meeting, we’re going to discuss all of the optimization strategies that increase conversion and reduce churn.

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One of the great things about being a college journalism major today is that it’s incredibly easy for professors to build their own news sites and allow students to experience every aspect of the publishing process. Not that long ago, journalism students had few avenues for publication outside their college newspaper.

Lydia Chavez took advantage of this dynamic while teaching at UC Berkeley. In 2008, she and her colleagues launched Mission Local, a local news blog that covered San Francisco’s Mission District. It quickly gained traction within the community, and in 2014 Lydia spun it out into its own independent news organization. Today, it’s fully sustained by a mix of large and small donors.

In our interview, Lydia walked me through how she incorporated the site into her journalism curriculum, why she spun it out from the university, and whether she thinks Mission Local’s model can be replicated across the US.

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.

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.

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.

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.

If you read articles about the state of local news, you’ll come away with a pretty pessimistic view of the industry. But while legacy newspapers have certainly faced a steep decline, there’s a burgeoning explosion of local media startups that are innovating in the space. 

One such company is Overstory Media. What started as a single local newsletter operating in Victoria has since expanded into 14 separate verticals operating all across Canada. In a recent interview, I spoke to CEO Farhan Mohamed about why he got into local news, his company’s acquisition strategy, and why he’s optimistic about the state of local news.

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.

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.

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Earlier this month, I sent a newsletter to my audience with the subject line: “Ask me a question.” Basically I told everyone to jump in the comments section of the post and ask me any questions they have about the media industry or creator economy.

Several of you did pipe in with questions, and so I spent a few hours jotting down notes and then recording this episode you’re about to consume.

I answered questions on a range of topics like the difference between a creator-led company and traditional media outlet, non-traditional media business models, my advice on launching a media business in 2024, and how long it takes to build a media business from scratch.

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.

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.

We live in an era where every company is expected to operate as a media company and every business executive is expected to produce thought leadership content. Newsletters and blogs have become crucial mediums for establishing longterm relationships with customers, and you’ve probably noticed that your LinkedIn feed has been flooded with posts from CEOs and startup founders who want to share their expertise.

But what happens when those CEOs don’t have the time or the writing expertise needed to produce compelling content? They often turn to ghostwriters: trained journalists who are able to quickly distill executives’ thoughts into shareable copy. These ghostwriters often work behind the scenes – in fact most people barely know they exist – and they can often make much more money than your average journalist.

But how do you break into ghostwriting when they’re effectively invisible, and what’s the best way to work with clients? To answer this question, I assembled a panel of ghostwriting experts to share their experience from building their businesses.

When 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.

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.

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.

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.

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.

My newsletter: https://simonowens.substack.com/

When it comes to knowing all the intricacies of real estate investment, few are more knowledgeable than Brad Hargreaves. In 2015 he founded Common, a company that manages rental properties and consults  with real estate investors on building design.

And then in 2022 Brad decided to begin sharing his knowledge through a paid newsletter called Thesis Driven. Within a matter of months, it was generating six figures in revenue, and he decided to step down from his role at Common so he could focus on building out a data platform geared toward real estate investors.

In our interview, we talked about why he launched Thesis Driven as a paid only newsletter, how his content is differentiated from most other real estate journalism, and why he think there’s an opportunity to build a Bloomberg Terminal for real estate investors.

My newsletter: https://simonowens.substack.com/

Today, the personal finance content niche is absolutely ginormous. You can’t open up YouTube, TikTok, or Instagram without encountering an influencer who gives advice on how to make and save money.

Today’s guest Philip Taylor anticipated this content explosion all the way back in 2011. That’s when he launched FinCon, a conference specifically designed for personal finance content creators. That first year he attracted around 250 attendees, but over the next decade it grew into the largest conference in this niche, attracting over 3,000 attendees a year.

In our interview, Philip walked us through how he got into the personal finance space, his strategy for growing the conference, and his ambitions for launching similar conferences in other niche categories.

For most of his career as professional ultra marathoner, Dylan Bowman didn’t have much of an online presence, but in 2019, he suddenly found himself with a lot of time on his hands after he broke his left ankle and had to take a year off from racing. That year, he launched a podcast where he interviewed his fellow pro runners, and it pretty quickly became a huge hit.

It didn’t take long for Bowman to realize that the podcast provided a huge opportunity for his post-racing career, so in late 2020 he and a co-founder launched Free Trail, a media outlet that operates a podcast network, a YouTube channel, and even its own ultramarathon races.

In an interview, Dylan walked me through how he built the company, his monetization strategy, and why it represents the future of sports media.

My newsletter: https://thelongstory.substack.com/

They walk among us, almost completely undetected. If you notice them at all, it’s because they’re pulling a discreet tin out of their pockets so they can replace the small, white pouch hidden above or beneath their molars.

Yes, I’m talking about Zyn enthusiasts. Though the nicotine pouch came to our shores over a decade ago, it’s only within the last few years that its reach expanded from the boiler rooms on Wall Street to the open office cubicles in Silicon Valley.

How did the product develop its obsessed fanbase? To answer that question, I turned to Carrie Battan, the author of a New Yorker piece titled “Zyn and the New Nicotine Gold Rush.” In our interview, she traced its origin as a Swedish cigarette replacement, explained why it has the potential to radically expand the nicotine-delivery industry in the US, and assessed the science as to whether nicotine is even bad for us when it’s not absorbed through the lungs.

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.

For the past several years, Twitter’s been a punching bag, both for tech writers and Wall Street analysts. It remained unprofitable, was a magnet for trolls, and, worst of all, its user growth came to a halt.

But in just the past few months we’ve seen some meaningful signs of life at the embattled social network. For one, it had its first profitable quarter in, well, forever. But it also saw growth in other areas. For one, though monthly active user growth is flat, it saw a sharp increase in daily active users. Also, a report from Social Flow found that Twitter traffic to news sites has increased while Facebook referral traffic has fallen.

Is this the sign of a company turnaround? Or just a temporary blip at an otherwise struggling company? I recently discussed these questions with Jonathan Rick, a digital media consultant based in Washington, DC.

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.

For more than a decade, publishers attempted to grow ad-supported businesses that depended on massive scale and distribution of free content, but in recent years, many have acknowledged that purely advertising-based business models simply don’t work in a world in which Facebook and Google are vacuuming up nearly all ad dollars that migrate online. So they’ve begun asking their readers to pony up, launching various forms of paywalls that require paid subscriptions for those wanting to access gated content.

There are three kinds of paywalls that have emerged: there’s the hard paywall where virtually all content is gated off. There’s the metered paywall, where the user gets access to a certain number of free articles before the paywall is triggered. And then there’s the freemium model, where a publisher will publish most of its content for free while reserving extra goodies for those willing to pony up money.

So what should these extra goodies be? Discounted tickets to live events? Access to a private Slack channel? Physical objects? Or just exclusive content? To answer this question, I interviewed Adam Rowe, a journalist for Tech.Co. Rowe recently wrote about subscription services and argued that publishers should put their best content in front of the paywall. He explained his reasoning in our interview.

Over the past few years, dozens of star journalists at mainstream media outlets announced that they were quitting their jobs to launch their own ventures, usually on platforms like Substack. As a result, some have drastically increased their income, sometimes into the seven figures. 

As more and more writers defected, I and others wondered how legacy media outlets would respond. Would they adapt their business models so that their writers could capture more of the value that they generate?

Last week, The Atlantic announced that it's partnering with about a dozen writers to author standalone newsletters for the magazine. Though the partnership details are somewhat vague, they could provide a framework for how media outlets will compete with platforms like Substack moving forward.

To discuss these moves, I sat down with communications consultant Jonathan Rick. We dove into The Atlantic's newsletter strategy and discussed whether it's effective enough to lure independent journalists back into the warm embrace of legacy media.

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 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.

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.

There’s this common saying you hear in academia: those who can’t do, teach. But that axiom certainly doesn’t apply to Jeremy Caplan. Not only did he have a decade of reporting experience before he started teaching entrepreneurial journalism at the City University of New York, but in 2020 he launched his own entrepreneurial media outlet: Wonder Tools.

Wonder Tools is a free weekly newsletter that highlights the most useful websites and apps to make your life and career easier. Since launching on Substack, it’s grown to over 23,000 subscribers and it’s generated a million visits in the last year.

In my interview with Jeremy, we talked about his journalism career, why he went into teaching, and what compelled him to launch his own media outlet.

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.

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.

Over the past several weeks, Spotify made several major announcements in the podcast space.

It opened up its advertising ecosystem to anyone who hosts their podcasts on Anchor. It launched the ability for podcast hosts to create video versions of its podcasts. And it reported two major milestones on its quarterly earnings call: that it grew its podcast advertising revenue by 100% over the last year and that it surpassed Apple as the #1 podcast player in the U.S.

What do all these announcements mean for the podcast industry? To figure it out, I invited on Jaclyn Schiff, CEO of a company called Podreacher. We discussed whether Spotify is a threat to the open podcast ecosystem and if it can become the YouTube of podcasting.

My newsletter: https://simonowens.substack.com/

What does a professional travel photographer do when all international flights are shut down due to a global pandemic? That’s a question Gary Arndt found himself asking in the early months of 2020. By that point, he had built up millions of social media followers and an entire career from snapping photos in exotic locales, and within a matter of weeks his income streams had completely dried up.

Luckily, he had already been batting around the idea for a podcast that didn’t require any travel. In July 2020, he started producing seven episodes a week of Everything Everywhere, an educational show about a diverse range of topics, and it immediately took off. Today, it generates 1.5 million monthly downloads and pulls in much more advertising income than Gary ever made as a travel photographer.

In our interview, Gary walked through how he found his audience, where he gets his ideas for new episodes, and why he weaned himself off the social media platforms that once delivered him huge reach.

This week I interviewed a guy named Ernie Smith.

Why do I think Smith is so fascinating? Because over the past decade he’s created two successful media properties, each with the absolute opposite goal of the other.

The first was a Tumblr account called ShortFormBlog. It amassed over 140,000 followers and was one of the hyperreactive news aggregators that thrived in the aughts. Every single day Smith logged in and plucked the most interesting quotes and stats from news stories and served them up in a tightly-packaged news product. The blog was so successful that it was covered in the pages of both Newsweek and Time (back when these were still relevant publications).

And then just when ShortFormBlog was at the height of its popularity, Smith abandoned it and launched a newsletter called Tedium. Unlike ShortFormBlog, Tedium would only be published twice a week and, instead of chasing headlines, it would tackle the most boring subjects imaginable and try to make them interesting. Several of its issues have gone incredibly viral and the newsletter now has over 10,000 subscribers.

Smith and I talked about why he made the switch and whether it’s possible to run a profitable independent newsletter.

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.

My newsletter: https://simonowens.substack.com/

When Patrick O’Shaughnessy launched his podcast Invest Like the Best in 2016, he had no intention of building it into a media company. He just wanted to use it to interview the world’s best investing minds so that he could deepen his own understanding of the industry. But the show proved to be a huge hit, attracting some of the biggest names in finance. By 2020, he and a few co-founders launched Colossus, an investing-focused podcast network that now produces more than a half dozen shows across various finance niches.

In an interview, Colossus CEO Matt Reustle walked me through the vision behind the network, how it develops and promotes new shows, and why the company hasn’t yet launched video versions of its podcasts.

My newsletter: https://simonowens.substack.com/

For most of Instagram’s existence, it wasn’t thought of as a platform for distributing news, but a growing number of media entrepreneurs have figured out ways to leverage its photo and video features to deliver engaging news digests.

One of those entrepreneurs is Sam Koslowski. Back in 2017, he and his co-founder launched The Daily Aus, a social first news outlet that’s grown its Instagram account to over 500,000 followers. As it ramped up its audience on the app, it began to diversify its content offerings across newsletters, podcasts, and YouTube.

In my interview with Sam, we discussed why Instagram was the ideal platform for launching the company, how it monetizes its content, and where he hopes to expand in the coming years.

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.

In some ways, Rahul Pandey’s career as a YouTuber has been pretty typical. After several years working at large tech companies like Pinterest and Facebook, he started uploading videos that gave career advice to other engineers who are trying to break into the industry. Then once he built a significant following, he left his full-time job in 2022 to focus on this type of educational content full-time.

But where he differs from other YouTubers is his choice of business model. Rather than going the typical route of securing brand sponsorships, he instead co-founded Taro, an online community platform where engineers can collaborate and share career advice. The company monetizes through a monthly subscription, and to date it’s mentored thousands of engineers through its community.

In our interview, we discussed how Rahul built his channel, why he launched a tech platform, and what his future on YouTube now looks like. 

My newsletter: https://thelongstory.substack.com/

Earlier this year, China crossed a major milestone when BYD, an electric car company based in its Shaanxi province, surpassed Tesla in total sales. What’s more, most experts believe the country is only at the beginning of its EV dominance. In a recent Washington Post article titled “How China pulled ahead to become the world leader in electric vehicles,” journalist Christian Shepherd explained how the country’s centralized, top-down government prioritized every level of the supply chain, from the building materials to the manufacturing to the charging stations. 

In a recent interview, we discussed what decisions the country made over a decade ago to incentivize EV production, to the point where it can sell cars at nearly half the price of its non-Chinese competitors. We also explored what the US would have to do if it wants to catch up.

Will Sommer grew up in a conservative household and garnered an early interest in Rush Limbaugh and other right wing media figures. When he went to college, his politics changed, but his obsession with conservative media never went away.

In late 2016, that obsession paid off. Sommer was one of the first reporters to write about Pizzagate, the conspiracy theory that a DC pizza parlor was the home of a child sex ring. After a man was arrested for firing a gun inside the restaurant, his reporting gained national relevance.

Shortly afterward, he launched Right Richter, and he soon became one of the foremost experts on the obscure right wing media outlets that, in some cases, produce conspiracies that bubble all the way up to Donald Trump’s Twitter account.

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.

If you run a hit podcast, you might have a couple avenues open to your for monetization. You could host live events and charge admissions, like what we’ve seen with Slate’s Political Gabfest and Pod Save America. You could, like Gimlet Media, launch a membership program and charge $60 a year for free tshirts, exclusive bonus content, and access to a private slack channel. Or you might turn to running sponsored ads within your podcasts, an approach that generated $220 million for podcasts in 2017.

But Macmillan’s podcast network is more diversified than most. The book publisher has been producing podcasts since 2007, and in addition to selling host-read sponsorships, it’s also generated revenue from running programmatic ads on its website. But what’s perhaps most interesting is how it’s leveraged podcasts to elevate the brands of its authors in order to sell more books and audiobooks.

I recently sat down and interviewed Kathy Doyle, vice president of podcasting at Macmillan, about the publisher’s strategy heading into 2018 as it expands its podcast lineup.

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.

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.

If you want to subscribe and listen to podcasts, there are dozens of apps to choose from, including podcast-specific apps like Stitcher and even music streaming apps like Spotify.

But anyone who works in the industry knows that Apple is the king of podcasts; its podcast app, which it spun off from iTunes a few years ago, accounts for more than 50 percent of all podcast use.

This is why Apple’s podcast rankings can be so important for driving discovery and downloads. There’s one master list of the top 200 most popular podcasts at any given moment, and then there are also dozens of content categories, each with its own top 200 list. Making it to the top of one of these lists can drive thousands of fresh downloads and put a podcast on the map.

But how does Apple rank its podcasts? And what’s the best way to make it onto one of its lists? To answer this question, I interviewed Dan Misener, the head of audience development at a company called Pacific Content, which specializes in helping brands develop their own podcasts.

For over a year, Misener ran an experiment in which he took snapshots of the Apple podcast charts and kept track of which content categories showed up most consistently. I interviewed Misener about his findings and what strategies his company uses to get a client podcast ranked.

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. 

My newsletter: https://simonowens.substack.com/

David Stein had an innovative marketing hack for growing his investing podcast called Money for the Rest of Us. He put the names of other popular finance podcasts in his metadata, and Apple’s unsophisticated search algorithm would surface his show whenever people were searching for his competitors.

By the time Apple eventually eliminated that functionality, Money for the Rest of Us had built up a loyal audience that’s since downloaded the show over 20 million times. His audience is so loyal, in fact, that it sustains a high-priced membership community that charges $450 a year and generates well into the six figures in revenue.

In a recent interview, David walked me through how he developed his investing expertise, what he offers to paying members, and why he launched his own premium investing app.

It’s not very easy to find online coverage of the gun industry that isn’t hyper polarized. The issue is dominated by a mix of NRA members and gun control activists, and even the traditional media does little more than play referee between these two sides.

When Stephen Gutowski launched The Reload in 2021, his aim was to cut through this noise. Stephen had spent several years covering the issue for The Washington Free Beacon, and despite his background in conservative media, his work has been widely praised by both centrist and left-of-center journalists. In 2022, CNN hired him to serve as an on-air analyst around gun policy issues.

In my conversation with Stephen, we talked about why he struck off on his own, how he monetized his newsletter, and what role his cable news career plays in building his audience.

According to Alexa, Wikipedia is the sixth most visited website in the U.S. and the fifth most visited in the world. When you Google famous people, places, or companies, their Wikipedia pages usually come up as the first or second result. If you’re a company that already has a Wikipedia page, then monitoring what’s written on it is vital to your reputation management strategy. If you don’t have your own Wikipedia page, then you may aspire to create one for yourself.

But this is where companies often get into trouble. Wikipedia has strict conflict of interest rules, and the site’s army of dedicated editors and admins are often quick to reverse undisclosed edits from conflicted parties. Abuse the rules too much, and you may get yourself banned or, even worse, attract attention to your page from activists who want to do your brand harm.

So what’s a company to do if it wants to edit its Wikipedia page without running afoul of Wikipedia’s rules? You’ll want to call a guy like Bill Beutler. Beutler, founder of a company called Beutler Ink, has been conducting Wikipedia consulting for almost a decade and led a coalition of PR firms in developing a code of ethics for Wikipedia editing. I spoke to Bill about how he fell into his line of work and how he navigates Wikipedia’s regulations on behalf of clients.

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.

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.

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.

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.

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.

Sign up for my course: http://contentbusiness.org/

When it comes to coverage of the tech sector, few publications can match the journalistic heft of The Information. Launched by former Wall Street Journal reporter Jessica Lessin in 2013, The Information quickly became an industry powerhouse, attracting some of the world’s best journalists who broke many of the biggest scoops over the past decade. If there’s a major story in tech, chances are that an Information reporter is chasing it. 

So it wasn’t exactly a surprise when, in January 2021, the publication put out a job ad for a Creator Economy reporter. With an estimated $100 billion in annual revenue, the Creator Economy has not only launched the careers for thousands of creators, but it’s also become the core focus for many of the world’s largest tech platforms. Venture capitalists are now pouring billions of dollars into Creator Economy startups, and creators themselves are upending entire industries that include beauty, commerce, health, and entertainment.

In April 2021, The Information announced that it had hired Kaya Yurieff, a former CNN tech reporter, to helm its Creator Economy coverage, and she’s since launched a daily newsletter that, in addition to publishing regular feature stories, also rounds up deals, trends, and product launches. 

Given the relative newness of the Creator Economy beat, I wanted to get a better idea of how Yurieff shapes her coverage. In a recent interview, she walked me through her weekly routine for news gathering, her methods for assessing startup founders’ claims, and where she thinks the industry is heading in the near future. 

My newsletter: https://simonowens.substack.com/

When Jared Newman launched his Cord Cutter Weekly newsletter back in 2016, the streaming TV market was much smaller than it is today, with most TV networks either not having their own streaming app or requiring a cable subscription to access it. But as it turned out, he timed his launch perfectly, as it was only a matter of years before virtually every Hollywood studio pivoted to streaming. Today, his newsletters has over 32,000 subscribers, and a spinoff newsletter that gives tech advice has also grown to 1,200 paying members.

In our interview, we discussed his motivation for launching the newsletter, why his editor let him promote it at the end of his columns, and whether he ever wants to leave his freelance career entirely to just focus on growing his two newsletters.

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.

Every year we get new articles questioning whether “email is dead.” With the proliferation of social media and messaging apps, it seems only natural to ask what will replace a decades-old electronic messaging system that really hasn’t changed much in all the years we’ve used it.

But email has remained resilient, and it’s even experienced a renaissance of sorts lately. In the wake of Facebook’s algorithm changes that are designed to hurt content providers, more and more publishers are launching new email newsletter products. It’s impossible these days to fire up a podcast or watch a YouTube video without encountering an ad for Mailchimp.

And of all the email providers, Gmail is king. The Google-operated service has over 1 billion users and is one of the few major email platforms that is actually continuing to innovate. In 2014, it opened up its API to developers, allowing them to build new products that Gmail users can install.

It was around this time that Ajay Goel was on the lookout for an opportunity to launch a new business. It was while he was looking around for a tool that would send mass emails that he came up with the idea for Gmass, an add-on that allows users to schedule and send mass emails directly from their Gmail accounts.

I interviewed Goel about his long career of building email-based tools and why he doesn’t think email’s going away anytime soon.

My newsletter: https://simonowens.substack.com/

My newsletter: https://simonowens.substack.com/

In 2017, Ben Cohen was living the dream. His politics news site The Daily Banter was generating over 6 million visits a month and enough advertising revenue to support him and a small stable of writers. But then the floor fell out from under him virtually overnight; Facebook pivoted away from news and sent his traffic plummeting. Without traffic, his advertising revenue crumbled.

So in an act of desperation, Ben pivoted his entire business model into paid subscriptions. Doing so forced him to slow down his publishing schedule and focus on serving his core audience. Slowly but surely, he built up a new revenue base, and in the last few months he passed the threshold of 1,000 paid subscribers.

In a recent interview, Ben explained how he executed on his pivot and why he’s determined to never rely on a single large tech platform ever again.

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.

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.

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.

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. 

The influencer marketing industry is estimated to generate $2 billion a year, with $1.6 billion coming from Instagram influencers alone. That number is only set to increase, with 39 percent of marketers saying they plan to increase their influencer marketing budget this year.

It’s now pretty much impossible to open up Instagram or YouTube without seeing #sponsored posts popping up from your favorite stars, from Kim Kardashian all the way down to food Instagrammers who only have a few thousand followers.

But whenever there’s this much money on the line, you always have people who are trying to game the system. It’s incredibly easy these days to inflate your follower count by purchasing bots or engaging in other kinds of shady activity. If you’re a company who’s thinking of hiring a social media influencer, how can you ensure that their followers are real?

Well, you’ll probably turn to someone like Erick Schwab, the COO of a company called SYLO. SYLO is a tech platform that can scan social media accounts and detect fraudulent activity. I interviewed Schwab about the state of social media influencer fraud and how his platform is able to tell when an Instagram account is propped up by an army of bots.