The Business of Content: Recent Episodes
Simon Owens, tech and media journalist
My newsletter: https://simonowens.substack.com/
The last few years have been pretty good to the Kansas City Chiefs, what with its multiple Super Bowl championships and a close association with the biggest pop star in the world, but BJ Kissel remembers what it was like to be a fan of the team long before it started regularly winning games. Back in the early 2010s, he began blogging for SB Nation, and he used his success there to eventually land a job as the Kansas City Chiefs in-house reporter. In that role, he did everything from writing web articles to serving as a sidelines correspondent for live game broadcasts.
In 2021, he struck off on his own and co-founded the KC Sports Network, a group of podcasts and YouTube channels that cover Kansas City Sports. Today, puts out 10 different shows and is monetized through a mixture of local and national advertisers.
In a recent interview, BJ explained why he left his job at the Chiefs, how he convinced local businesses to sponsor his shows, where he sees new opportunities for growth.
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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.
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Book publicity is a mixed bag these days. On the one hand, it’s never been easier for an author to form a direct relationship with their audience with tools like Substack and TikTok. On the other hand, more books are published each year than ever before, which means competition is fierce. Most newspapers have laid off most of their book critics, but at the same time there’s an ever expanding ecosystem of podcasts that are eager to have on book authors for longform interviews.
Probably nobody is more knowledgeable about marketing books in the modern age than Kathleen Schmidt. She spent nearly 20 years working for almost every major book publishing company, and she now runs her own firm that specializes in book marketing. She also writes Publishing Confidential, her insider account of how the book industry actually functions.
In a recent interview, Kathleen walked through nearly every aspect of selling books, from choosing the right cover to courting influencers to advertising on Amazon.
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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.
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Eric Siu has a pretty massive audience; his YouTube channel boasts 161,000 subscribers and his two podcasts – Marketing School and Leveling Up – have generated tens of millions of downloads.
But Eric doesn’t bother with traditional media monetization models like advertising or subscriptions. Instead, he leverages his influence to drive clients to Single Grain, a marketing agency he owns. As that business grew, he was able to acquire more agencies and add to Single Grain’s capabilities, and it now works with some of the world’s largest brands.
In a recent interview, Eric explained how he met his co-host, where he found his audience, and why he chose to monetize his content with a services business.
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When Keith Pepper bought a chain of print newspapers back in 2020, he received an email from a columnist at the Atlanta Journal Constitution that basically asked if he was crazy. But Keith had a plan for taking a company that generated 98% of its revenue from print advertising and converting it into a digital-first media company.
And he’s done just that. Today, Rough Draft Atlanta generates 27% of its revenue from digital ads, and it managed this feat without seeing a significant decline in print advertising. This has allowed Keith to reinvest in the business by hiring more journalists, and it’s now stronger than ever.
In a recent interview, Ketih explained how he consolidated all the newspapers under a single brand, his strategy for attracting online ads, and why he’s avoided placing his content behind a paywall.
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Layoffs in the local news sector are, sadly, a regular occurrence, but the founders of Block Club Chicago decided they weren’t going down without a fight.
In November 2017, the news startup DNA Info laid off its entire staff, and it was only a few months later that three of its editors launched a Kickstarter that raised over $183,000; they used that capital to launch Block Club Chicago, a nonprofit that seeks to put a journalist in each of the city’s neighborhoods.
Flash forward six years, and Block Club has a robust news gathering operation that’s funded by 20,000 paying subscribers, foundation support, and a growing advertising business. In a recent interview, co-founder Stephanie Lulay walked me through the site’s launch strategy, its unique approach to neighborhood-based reporting, and why she thinks Block Club’s model can be replicated all across the US.
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For much of its 130-year existence, State House News operated as a standard newswire service. Its journalists covered the Massachusetts state government and it then syndicated their content to regional and national newspapers.
But in the late 90s, owner Craig Sandler realized that internet distribution would allow him to sell direct digital subscriptions and vastly expand his customer base. Today, the service charges $4,000 a year to any company or organization whose business is directly influenced by the state’s government.
In a recent interview, Craig discussed how he built the direct subscription business, why he decided to sell a majority stake in the company, and whether State House News is shielded from the whims of large tech platforms and AI chatbots.
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Most people are familiar with newswires like the Associated Press and Reuters, but a much newer upstart called Stacker has devised a new business model for syndicating content. Rather than charging a fee for its articles, it instead gives away its data journalism to any publisher that wants it. It then charges brands a fee to create and distribute sponsored content across the thousands of media outlets that subscribe to its service.
In a recent interview, co-founder Noah Greenberg explained how Stacker works with publishers, its process for creating sponsored content, and why he has no interest in driving an audience to Stacker’s owned and operated website.
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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.
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Most companies buy advertising to drive sales of their products, but Andrew Curtin’s first sponsor mostly bought out of pity. It was May 2022 and he had just launched Construction Wave, a B2B outlet that covers the UK’s construction industry. He had absolutely no audience, but a major crane manufacturing company bought a $10,000 sponsorship anyway.
That $10,000 allowed him to hire his first editor, and over the next two years they built Construction Wave up into one of the leading publications in its sector. Its website is mainly monetized through high-priced sponsorships, and this year it hosted its first conference geared toward construction CFOs.
In an interview, Andrew explained how he got interested in the sector, where he found his initial readers, and why he thinks there’s an opportunity to launch a subscription data product for his industry.
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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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When Alex Halperin launched WeedWeek in 2015, he was entering an industry that had nothing but growth ahead of it. But what he didn’t expect was that the fragmented legalization across states meant that it’d be difficult to build a national audience. So a few years ago he pivoted to just covering California’s weed industry, and WeedWeek has since built a robust business monetized through both sponsorships and subscriptions.
In our interview, Alex walked me through what got him interested in the topic, why he built a customer publishing platform, and how he recently decided to team up with the LA Times on an investigative series.
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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.
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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.
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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.
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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.
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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.
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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.
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Ben McCarthy didn’t set out to create a media company focused on Salesforce, he just began blogging about his use of the product as a way to document the various use cases he encountered. As it turned out, there were thousands of other people who were encountering those same use cases, and via Google searches they began landing on Ben’s blog posts.
Fast forward 10 years, and he now runs a 20-person media company that generates over 1 million pageviews per month and is the most authoritative resource for Salesforce customers.
In our interview, we discussed why there’s such a huge audience for Salesforce content, how he monetizes with webinars and white papers, and whether he wants to launch more media outlets centered around other cloud technologies.
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When Joe Pulizzi launched The Tilt in 2021, he already had a pretty good idea of how to build a successful media company. Back in 2017, he had sold his previous media startup, The Content Marketing Institute, to one of the world’s largest event conglomerates.
Joe ran The Tilt with a very similar playbook – first starting with a weekly newsletter, and then expanding into an in-person conference called The Content Entrepreneur Expo, or CEX. The venture was so successful that he sold it to Lulu Press in 2023.
In our interview, Joe talked about his newsletter growth strategy, what it takes to put on a successful conference, and why he prefers the term “content entrepreneur” instead of “creator.”
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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.
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I spend most of my time on this show interviewing entrepreneurs who founded English-language media outlets – mostly because that’s the only language I speak – but that doesn’t mean I’m not interested in the media ecosystems from other regions in the world. That’s why I was super excited to talk to Andreas Sator, the host of one of the most popular podcasts in Austria.
Andreas got his start at a major newspaper, and after a few years at the outlet, he got to experiment with writing an explainer journalism column about personal finances. He found this sort of reporting to be much more enjoyable, so in 2018 he launched a podcast that roughly translates to “Explain The World to Me.”
In our interview, we discussed the Austrian podcast market, how he monetizes the podcast, and why he decided to launch a new show about climate change.
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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 into 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 some amazing questions. I then invited on Alexis Grant, the founder of They Got Acquired, to help me answer them.
We answered questions on a range of topics like:
- Which media companies are succeeding with native advertising
- The best ways for media outlets to run live events
- How to grow your audience in a world where Google and Facebook are sending less and less traffic
- What a Substack advertising platform would look like.
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.
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The rise of cloud computing introduced all sorts of benefits for the enterprise software space. Not only could license holders access their accounts from virtually anywhere, but it also allowed the software companies to issue updates on a more regular basis. But this also made the sector a lot more complicated and created a need for more experts who could educate cloud software customers about the intricacies of the tools.
Tom Arbuthnot is one of those experts. For over a decade, he’s been a Microsoft MVP and Microsoft Certified Master, and he spent a significant amount of time in the early 2010s educating the public about these products through blogging and conference talks. But then in early 2022 he realized that there was a market opportunity for a media company to cover these products. That year, he launched Empowering Cloud, an online community that produces a mixture of videos, live calls, and other educational materials centered around Microsoft’s cloud technology.
In my interview with Tom, we talked about the site’s launch, how he finds sponsors, and why he decided to lock most of the company’s content inside a community platform that requires a login.
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I think everyone likes to think of themselves as being financially savvy, especially if, like me, you write about business topics, but how many of us truly understand finance terms that are bandied about like gross profit and lifetime value. Like we may know that the term EBITDA stands for “earnings before interest, taxes, depreciation, and amortization,” but how many people actually know how to calculate it?
CJ Gustafson knows. After a decade in finance, he’s mastered all the accounting jargon, and a few years ago he realized that there was a market need for someone who could explain these terms in a way that’s both entertaining and informative. So he launched Mostly Metrics, a Substack newsletter about finance, strategy, and operations at startups.
CJ’s since grown the newsletter to over 42,000 subscribers, all while holding down his day job as a CFO at a tech startup. In my interview with him, we talked about why he launched the newsletter, how he balances his day job work and writing, and what his longterm plans are for the newsletter.
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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.
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Ask about just any media executive, and they’ll tell you that the year 2023 was not a good one for the advertising business. A combination of high interest rates and an uncertain economy made companies extremely skittish, and that caused them to pull back on their marketing spend.
There’s some recent signs that advertising spending is picking up in 2024, but it’s still too early to know how it will shake out.
But what about newsletter advertising? It’s seen some strong growth in recent years and brands have reported higher than average ROI due to the strong engagement that’s seen in the inbox. Has it suffered from the same macro economic forces that battered the larger ad industry?
To answer that question, I turned to Ryan Sager, the co-founder of Who Sponsors Stuff, a data platform that tracks sponsorships across hundreds of newsletters. Ryan dove deep into his own data to determine which sectors are investing big in newsletter ads and whether they’ve seen any slowdown in growth.
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By the time Riad Chikhani was 16 years old, he had already built a hugely successful online community for gamers and then sold it for a healthy sum. Two years later, he founded the company that would eventually become GAMURS Group, and while it took far longer to gain traction, it eventually grew into one of the largesting gaming media companies in the world, with outlets that include Dot Esports, Gamepur, and Gamer Journalist.
In my interview with Riad, we talked about his early business pivots, why he invested big in esports, and how he drives synergies between 17 different publications.
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 some amazing questions. I then invited on Alexis Grant, the founder of They Got Acquired, to help me answer them.
We answered questions on a range of topics like
- How to monetize newsletters on LinkedIn
- How we’d go about launching a local news outlet from scratch
- The future of paid newsletters
- How The Messenger should have spent its $50 million in VC cash.
This Q&A episode is actually part of an ongoing series. Every single month I’ll allow my subscribers to submit questions, and I’m going to do my very best to answer at least one question from every single subscriber. The only way to submit questions is by becoming a paid subscriber to my substack newsletter.
Subscribers also receive a calendly link from me that allows them to book a half-hour introductory phone call. Many of my subscribers use it as an opportunity to tell me about their own media businesses and pick my brain on strategy.
To subscribe, go to https://simonowens.substack.com/
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When Jack Karmer and Nick Martell launched their daily newsletter Market Snacks in 2011, they kept their names off the publication so that it wouldn’t jeopardize their finance day jobs. But once the newsletter started to attract readers and sponsorship revenue, they decided to come clean. Luckily, their bosses let them continue on with their side hustle.
Flash forward about a half decade, and Market Snacks had gained enough traction that they both decided to go to business school so they could learn to scale the company. Around that same time, they teamed up with a large podcast network to launch a daily companion show, and almost immediately it was featured on the Apple Podcast app.
This success didn’t go unnoticed. Robinhood, which at the time was a fast-growing stock trading app, came on at first as a sponsor, but a few months later decided to outright buy Market Snacks to leverage it as a marketing channel for the app.
Jack and Nick continued to host the podcast while managing the rest of the Market Snacks team, and then in 2022 they went to the Robinhood executive team with a radical proposition: they wanted to spin off the daily podcast and acquire it from Robinhood. Amazingly, their bosses went for it, and that year they renamed the podcast to The Best One Yet.
In my interview with Jack and Nick, we discussed how they came up with the idea for the newsletter, why Robinhood allowed them to take the podcast back, and what they’ve done with the company ever since they became full owners.
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It’s no secret that local journalism has struggled since the Great Recessions, with hundreds of newspapers shuttering and thousands of reporters losing their jobs. Over the past few years, entrepreneurs have launched dozens of local news startups to help fill in the gap, but there’s still an ongoing debate as to whether local news should be a for-profit or nonprofit industry.
Berkeleyside is one of the few organizations that has tried both models. For the first several years of its existence, it was a for-profit entity, but then in 2019 its founders switched it over to a nonprofit model, and it’s since expanded into three separate verticals that cover the bay area, with a fourth launch planned for 2024.
In an interview, co-founder Lance Knobel walked me through how Berkeleyside came to be, why it switched to a nonprofit model, and how it generates revenue through a combination of grants, memberships, sponsorships, and large donations.
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Lucas Grindley knows something about building sustainable revenue streams for media companies. When he was hired to Here Media, a network of LGBT news outlets, it was losing money, but over a period of six years he nurtured it back to profitability.
Now he’s the executive director of Next City, a 20-year-old nonprofit magazine dedicated to urban policy and equitable cities. When he first joined, the publication was almost entirely reliant on large grants, but he’s since diversified its revenue by building up its ad sales and small-donor memberships. Recently, it crossed the threshold of 1,000 paying members.
In a recent interview, Lucas walked me through his successful tenure at Here Media and explained how he’s brought a similar playbook to Next City.
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It’s been nearly five years since Spotify announced it would diversify its audio offerings beyond music streaming, and while it spent most of that time building its podcast capabilities, it made no secret that it eventually wanted to get into audiobooks.
Then in 2022 it made its first move into the industry by acquiring an audiobooks distributor called Findaway. Later that year, it launched the ability to purchase audiobooks through spotify. And then finally in late 2023 it rolled out audiobook streaming as part of its paid subscription.
There’s been one group that’s watched these developments closely: audiobook authors. They’re understandably nervous about how Spotify’s bundled offering will affect their own income, and many are deeply skeptical of the company’s intentions.
So will Spotify’s audiobook streaming be good for authors? That’s a question I put to Jane Friedman, the writer behind the publishing industry newsletter The Hot Sheet. She walked me through the current landscape of digital audiobook sales and explained how Spotify’s revenue sharing arrangement works.
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There are plenty of popular politics newsletters out there, but none with the kind of unique origin story of Wake Up to Politics. It was started by Gabe Fleisher when he was only 9 years old. While the early editions were sent out by a Gmail account and only read by his mom, Gabe kept at it, waking up early every day before school to write the newsletter. Flash forward about a decade, and he’s now a senior at Georgetown and Wake Up to Politics has close to 50,000 subscribers.
In my interview with Gabe, we talked about what kept him motivated all these years, how he monetizes the newsletter, and what he plans to do with it once he graduates.
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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.
It’s been a bad few years for Buzzfeed. After a disastrous IPO in 2022, it’s faced a tanking stock price, declining revenue, and a shutdown of its news division.
But things only look to get worse in 2024. As Adweek’s Mark Stenberg reports, BuzzFeed faces a fiscal cliff where it’s in danger of being delisted from the NASDAQ stock exchange, which then would trigger a required payment on its debt. Such an event would be disastrous for the company’s future.
I recently interviewed Mark about the dangers of the fiscal cliff and how likely it is to happen. We also discussed all the mistakes BuzzFeed made that led it up to this position.
How do you write about the travel industry when people can’t fly on airplanes? That’s a question Kelsey Ogletree had to ask herself in 2020 at the beginning of the pandemic. By that point, she had worked for several years as a freelance travel writer, and like many of her colleagues, she didn’t know how the travel restrictions would affect her own career.
So she decided to do something about it. She announced on her newsletter that she was hosting a live Zoom call about the future of the travel industry, and hundreds of people signed up to join her. That call was so successful, in fact, that she began hosting several more of them. Eventually, this ad hoc service grew into Pitchcraft, a paid membership community that costs thousands of dollars a year to join.
In a recent interview I spoke to Kelsey and her husband Derrick about how they built their platform, what benefits they offer to paying members, and how they attract new customers.
Ash Read didn’t launch a review website about household products because of some lifelong interest in home decor; instead, his interest came about simply because he was moving into a new house and needed to furnish it.
While it was easy to search for products listed on retailers like Amazon and Walmart, he realized that there wasn’t a good directory for the direct-to-consumer goods that are sold directly through a company’s website. So he created a database of direct-to-consumer companies and published it to the web. The audience feedback was so strong that he decided to build out an entire website dedicated to covering and reviewing D2C home products.
Ash launched Living Cozy in 2020, and over the next few years he scaled the site to over 350,000 monthly pageviews. What started out as simple product curation soon led to an in-depth review process and him hiring a network of freelance writers to review items like sofas and beds.
How did Ash manage to break into such a saturated market category that was already dominated by much larger websites? In an interview, we talked about his introduction to direct-to-consumer products, his clever use of search keywords, and how he coordinated the shipment of large pieces of furniture to reviewers all over the world.
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.
In 2011, Rafat Ali launched Skift, a B2B publisher that covers the travel industry. At first, Skift was mainly monetized with advertising, but Rafat quickly realized that scaling a B2B niche outlet required a diverse set of business models that included memberships, research, events, and advertising. He also acquired multiple other media outlets that operated in adjacent industries.
In an interview, Rafat walked us through this journey and explained how he managed to simplify the company’s value proposition while embracing the complexity of multiple revenue models.
We also spoke to Walter Frick, who ran the membership program for business publisher Quartz for nearly three years. He answered our questions about what motivates readers to convert into subscribers and what he learned when Quartz made the radical decision to completely remove its website paywall.
Patrick Walls is the founder of Starter Story, an outlet that’s published thousands of case studies on how entrepreneurs built successful businesses. At one point, he was selling upward of $50k a month in sponsorships.
But earlier this year, he not only stopped selling advertising, he also switched from recurring subscriptions to a one-time payment that gave customers permanent access to his content archives. The move helped him grow to $1.5 million in annual revenue.
In a recent interview, he talked about why he got tired of chasing sponsors and his motivations for switching from subscriptions to one-time payments.
I also spoke to Bradley Hope, a former Wall Street Journal reporter and co-author of the New York Times bestselling book Billion Dollar Whale. In 2021, he co-founded Project Brazen, a production studio that creates narrative nonfiction across podcasts, books, newsletters, TV, and film.
He answered questions about how he chooses narrative projects to fund and the process for adapting a single piece of IP into multiple formats.
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.
If you run any sufficiently large organization, one of the biggest threats to your business is runaway costs. The largest companies can use upwards of thousands of suppliers for everything ranging from software technology to building materials, and how much you spend on all these suppliers can be the determining factor over whether you’re profitable or unprofitable.
That’s why most large businesses employ procurement specialists – people whose job it is to oversee and negotiate services with outside companies. It’s not the sexiest job in the world, but it’s incredibly important, and it’s the reason why the procurement services industry is worth $6 billion.
Philip Ideson runs a media company that covers this massive industry. After spending 15 years as a procurement specialist himself, he launched The Art of Procurement, a news and information resource that caters to procurement specialists. Over the past seven years, he’s built it into a business that’s monetized through live events, sponsorships, and consulting.
In our interview, he talked about his motivation to launch the company, how he built his audience, and why he struggled so long to find a viable business model.
There’s a common criticism lodged against Substack that its model of paid subscriptions could never support original journalism, and instead it only caters to the kind of opinion journalism that can be churned out at a high rate.
Eric Newcomer is proving this criticism wrong. After six years spent reporting at outlets like The Information and Bloomberg, he struck off on his own and launched a newsletter that covers startups and venture capital. Within months of his launch, he broke several major stories about top VC firms like Andreessen Horowitz and Sequoia.
In our interview, Eric talked about his motivation to leave his job in traditional media, his monetization strategy, and how he manages to break major stories at such a consistent rate.
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.
Today, Android is the number one operating system for smartphones, but when Google launched the product in 2008, the iPhone already had a huge head start. Most consumers didn’t know it existed, and even the tech press didn’t take it super seriously.
But JR Raphael was an early fan. A freelance tech journalist who wrote for publications like Fast Company and The Verge, JR pitched his editors at Computerworld on a regular column about Android, and though they were skeptical at first, they gave him the green light.
As Android grew into a major mobile operating system and eventually overtook the iPhone, JR became one of the leading authorities on the product. In 2018, he launched Android Intelligence, a supplementary newsletter that mostly linked to his column and other news items, but as it picked up steam, he began to introduce more and more monetization features. By 2023, Android Intelligence was generating the majority of his annual income.
In our interview, JR explained to me why he was such an early fan of Android, what motivated him to launch the newsletter, and how he turned it into a thriving business.
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.
When it comes to creating content for online audiences, few people are more experienced than Mark Talkington. He was one of the original editors of ESPN.com and then later spent 20 years as the news editor for MSN.com, the massive web portal owned by Microsoft.
But starting at the beginning of the pandemic, Mark began writing for a much smaller readership: the residents of Palm Springs, California. Taking advantage of the fact that most government meetings were now being broadcast online, he spent his nights and weekends writing a daily newsletter dedicated to keeping citizens informed about their local community.
The newsletter was called The Palm Springs Post, and it was an instant hit, growing to 13,000 subscribers in a little over a year. By 2022 he was able to hire another journalist and launch a second newsletter covering a nearby region. Earlier this year, he left his job at Microsoft to focus full-time on growing his company.
In our interview, Mark talked about how he produced the newsletter during his free time, his business model, and what other local news entrepreneurs can learn from his approach.
Of all the media revenue models, subscriptions can be the most tricky to execute well. There are just so many variables at play that impact a publisher’s ability to succeed. You have to figure out what to place both in front of and beyond your paywall, how to price your subscription, how to convert free readers into paid subscribers, and how to reduce your churn.
And that’s just scratching the surface. Getting one of these variables wrong can mean all the difference in determining whether a subscription business succeeds or fails.
That’s why I convened a panel of experts to dive into the nuances of subscription economics and identify the strategies that will increase your chances for success. They included:
Peter Ericson, CEO of the Leaky Paywall subscription platform, which helps publishers seamlessly build their audience and grow paid subscriptions
Michael Donoghue, CEO of Subtext, a platform that allows publishers to send text messages to their paid subscribers
Jane Friedman, founder of The Hot Sheet, the most successful paid newsletter that covers the book industry
Randy Cassingham, founder of This is True, possibly the world’s first paid email newsletter
The local news industry has seen better days. The last 15 years or so have been pockmarked with mass layoffs, shuttered newspapers, and growing news deserts.
But there have been bright spots in the local news landscape … lean media startups that aim to fill the gaps left by their legacy newspaper counterparts. One such startup is called City Cast. Founded by former Slate editor David Plotz, City Cast has a unique model in which it simultaneously launches both a daily newsletter and podcast in each city it covers.
For this episode, I spoke to Bryan Vance, City Cast’s director of newsletters. We discussed the company’s playbook for launching in new cities, how it creates synergies between its podcasts and newsletters, and its approach to gathering local news
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.
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.
While paid subscription models have been all the rage for the last decade, more and more creators are turning to online courses as a way to monetize their audiences. Their evergreen nature makes them ideal for generating passive income, and many creators have succeeded at selling them at relatively high price points.
But what’s the best way to develop a course that your audience will actually want? And how do you market it to that audience?
I recently convened a panel of professional course creators to answer these questions. We talked about everything including identifying course topics, setting prices, and choosing the best platform to host your course.
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.
Historically, foreign correspondents haven’t been the type of journalists who break major news stories in the countries they cover. That’s because they’re typically not as well sourced as the local reporters who grew up in a particular region and have an intimate knowledge of its issues.
But what would happen if you could take the work of local reporters and translate it for English-speaking readers? That’s the idea behind Worldcrunch, a media outlet that was founded in 2011. Rather than creating all of its own content, it syndicates articles from publications all around the world and then pays translators to adapt those articles for a Western audience.
In a recent interview, founder Jeff Israely talked about his years of work as a foreign correspondent for Time Magazine and how that fueled the idea for Worldcrunch. He also discussed the publication’s evolving business model as it moved from syndication to advertising and subscriptions.
Before the major social platforms launch a new product, they’ll often run small experiments within a subset of their users to test it out. More often than not, the first person to spot these new products is a guy named Matt Navarra, and his mini scoops have been cited in thousands of news articles over the years.
Matt got his career start running the digital communications for the UK government and then later became the director of social media for The Next Web. In 2018, he struck off his own and launched his own marketing consultancy.
It was that same year that he began writing Geekout, a weekly newsletter that curates emerging news and information around the marketing industry. Within a few months it amassed thousands of subscribers, and today it drives six figures in revenue, mostly through sponsorships.
In my interview with Matt, we talked about where he gets his product scoops, his audience growth strategies, and how he built a six figure newsletter business as basically a side hustle.
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 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.
By the time Emanuel Cinca launched his Stacked Marketer newsletter around five years ago, he already had a successful affiliate marketing business, but that business was largely dependent on the whims of other platforms like Facebook and Google. He wanted to build a product that he could monetize directly, and by that point he had grown to admire daily digest newsletters like Morning Brew and The Hustle.
So Emanuel decided to niche down and launch a newsletter geared toward the marketing industry. To grow the newsletter, he leveraged his skills in paid media and marketing, and today it has over 30,000 subscribers. In 2022, it generated over half a million dollars through a mixture of paid subscriptions and sponsorships.
In my interview with Emanuel, we went deep on how he designed the newsletter, his growth strategy, and how he approached monetization.
When it comes to distinctive newspaper designs, the print edition of The Financial Times stands out. The 135-year-old publication is instantly recognizable for its salmon pink paper, and it’s become a status symbol for London’s monied elite.
The newspaper’s web presence is extremely successful as well. In early 2022, it announced it surpassed 1 million digital subscribers, an especially impressive feat given its hefty price tag of over $400 a year.
So given this success, why did the FT launch a mobile app last year that only costs around £5 a month?
To answer this question, I turned to Malcolm Moore, a longtime Financial Times editor who was put in charge of FT Edit, which is the name for the new mobile app. We discussed why he was chosen to lead the initiative, what the app has to offer that differs from the main newspaper, and who the audience is for the product.
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As the media industry focuses on revenue diversification, more and more publishers are venturing into live events — both virtual and in-person. Not only can they be monetized in multiple ways, but a well-planned event can provide a great venue to forge a deeper connection with your most engaged audience.
But events are tricky to pull off and can be intimidating for those who haven’t hosted one before. For this episode, I pulled together a panel of people who run some of the most successful events companies in the world. They include:
Chris Ferrell, CEO of Endeavor Business Media
Bo Brustkern, co-founder of Fintech Nexus
John Allsopp, who runs one of the most influential conferences for web designers, developers, and digital creatives
Ross Douglas, founder of Autonomy Paris, a major trade show
Sarah Peck, a podcaster who launched the Wise Women’s Council
Boye Fajinmi, co-founder of The Future Party
And Randy Gage, a New York Times bestselling author
In our discussion, we talked about everything including what to charge, picking a host city, finding sponsors, and negotiating with venues.
While podcasting has been around since the mid-aughts, it’s only within the last half decade that the industry started generating significant revenue, finally crossing $1 billion in 2021. And until recently, there were very few journalists who were solely dedicated to writing about podcasts. That’s a big part of the reason that in 2017 James Cridland decided to launch Podnews, a B2B newsletter that covers the industry.
A longtime radio veteran who once worked for the BBC, James realized that there was a major need for a daily news digest of all the various startups and media outlets that were operating in the space. And as his readership grew, he found that there were plenty of companies that were willing to pay to reach his hyper-niche audience.
In my interview with James, we talked about his approach to compiling his newsletter, his monetization strategy, and why he insists on coding most of his tools from scratch.
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.
B2B used to be the least sexy space in media, but in the last decade we’ve seen a new crop of B2B media companies that are proving to be far more innovative than their B2C peers. Recently, I convened a panel of experts to talk about all the various aspects of B2B media — including running events, launching paid subscriptions, finding sponsors, and building out niche editorial products.
What you’re about to listen to is a recording of a live Zoom call I had with my newsletter’s paid subscribers. I host these calls at least twice a month, and for each one I recruit some of the world’s foremost experts in media and content. If you want access to these calls, then you need to become a paid subscriber to my newsletter. Go to simonowens.substack.com. That’s simonowens.substack.com.
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Matt Brown didn’t set off to build his own solo newsletter business, but he fell into it after taking a buyout at Vox Media sports site SB Nation during the height of the pandemic – a period when very few media companies were hiring.
While his SB Nation beat covered all of college sports, Matt decided to niche down with his own newsletter – which was called Extra Points – to focus specifically on the business side of college athletics. This gave him the edge he needed to find a loyal audience, and he quickly scaled it up to thousands of readers.
In my interview with Matt, we talked about why he left Vox Media, how he monetized his newsletter, and what made him want to sell it to a larger media company.
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When the media outlet Roca News launched in the year 2020, it started creating just about every kind of content you can imagine. There was a newsletter, a podcast, and accounts on every single social media platform.
But this everything-but-the-kitchen sink approach didn’t seem to work, so the founders decided to focus mostly on a single platform: Instagram. Over the next two years, they leveraged Instagram’s visual storytelling features to deliver a digestible form of news to its young followers. This singular focus allowed it to grow to over 1.1 million followers.
Then, starting in 2022, it branched out into other mediums. It reinvested in its daily newsletter and also launched a TikTok account where it publishes more humorous, entertainment focused content. It also started building a dedicated mobile app, which it’s launching soon.
In this episode, I interviewed co-founder Max Towey about the Roca News origin story, its Instagram growth, and how it’s begun monetizing its content.
My newsletter: https://simonowens.substack.com/
You’ve probably noticed that true crime is having a bit of a moment right now. Podcasts dedicated to the genre dominate the charts, and every week there’s a new hit series on one of the major TV streaming services.
Jim Brown approached true crime from a different direction. Rather than launching a show, he used his tech and product skills to build a database of cold cases. Think of it as a kind of Wikipedia for unsolved crimes.
He then created ways for users to submit updates and participate in the discussion around these cases. The site, which is called Uncovered, now attracts tens of thousands of monthly visitors and recently played a key role in solving a cold case.
I spoke to Jim about building the site, how it attracted its initial visitors, and its monetization strategies.
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Louie Woodall knows his way around a financial disclosure document. Since graduating college, he’s worked for several media outlets that report on the intricacies of financial risk. In 2020, he decided to combine this expertise with his interest in climate change and launched Climate Risk Review, a Substack newsletter that analyzed climate disclosure documents published by major corporations around the world.
The newsletter was a side hustle, but it eventually amassed an influential readership of bankers and other finance professionals, many of whom converted into paying subscribers. Eventually, Louie realized he needed to make a decision: should he continue it as a side hustle or try to make it his fulltime job?
He decided on the latter option, and to help ease that transition he found a company that would not only acquire the newsletter, but also employ him to be its full time editor. In our interview, we talked about the newsletter’s origin story, his monetization strategy, and how the publication will evolve under the umbrella of a larger company.
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The podcast industry is around 17 years old, and Libsyn was among the first companies launched to service that industry. For most of that time, it focused on paid podcast hosting, but in recent years it’s acquired companies that specialize in podcast advertising and subscriptions.
Libsyn needs that more diverse product offering if it wants to compete with rising podcast behemoths like Spotify and SiriusXM. I recently sat down with Dave Hanley, who helps run its advertising operations. He told me the story behind Libsyn’s acquisition of his podcast advertising platform and the company’s strategy for recruiting the next generation of hit podcasts.
Check out the News Guest podcast: https://bit.ly/news-guest
When Boye Fajinmi started hosting parties with a few of his friends, he had no idea that it would become a sprawling events and media company. They were just looking for a fun way to network with other creative workers like themselves. At the time, Boye worked at Paramount Pictures and was pursuing a traditional Hollywood career, but the success of those early parties led him to believe that he could build something of his own.
Flash forward a decade, and The Future Party – which is what the company came to be called – now hosts dozens of events a year and works with some of the largest luxury brands in the world. It also publishes a daily newsletter that reaches 150,000 people.
Boye and I sat down to discuss The Future Party’s origin story, its monetization strategy, and why they decided to expand beyond events into media.
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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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In terms of career advancement, Brandi Kruse was at the top of her game. As a TV news correspondent in the large media market of Seattle, she was paid more than most of her industry peers, and she even hosted her own longform weekly talk show.
But in late 2021, she quit her job and immediately launched her own podcast called Undivided. Within weeks of the launch, she amassed over 2,000 paying subscribers on Patreon, and she now delivers her commentary and interviews to over 200,000 followers across Facebook, Twitter, and YouTube.
How did Brandi find this audience, and why did she ditch her well-paying job in TV? In our interview, she explained how she grew a large following on Facebook and used it as a launching pad for her independent career. She also told me about her efforts to expand beyond local news and into national politics.
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Over the past decade, several major media companies have invested in building out their data journalism operations. ABC News has FiveThirtyEight, The New York Times has The Upshot. And Vox Media runs Vox.com.
These outlets have leveraged publicly available data to explain complicated stories, and the infographics they create are easily shareable on social media.
But most media outlets don’t have the resources to hire an expensive data team, especially if they operate at the local level.
That’s where Stacker comes in. Rather than producing journalism for its owned and operated site, it distributes its content as a newswire that can be syndicated by any news company. What’s more, it doesn’t even charge for this service. That means virtually every news outlet has access to its top-quality reporting.
How can Stacker afford to give away its content for free? To answer that question, I brought on co-founder Noah Greenberg. He walked me through Stacker’s origin story, how it found its initial publishing partners, and how it developed its monetization strategy.
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If you’re aware of Morning Brew, it’s probably because of its daily business newsletter. Since its founding in 2015 by two college students, it’s grown to over 4 million subscribers, and its news digest format has been copied by dozens of other media startups.
But since getting acquired in 2020 by Business Insider, Morning Brew has expanded into new niches in verticals. Not only has it launched several B2B industry newsletters, but it also invested heavily in podcast and video production.
That’s where Dan Toomey comes in. After graduating college in 2020, he pitched Morning Brew’s founders on the idea of him coming on board to create video, and to his surprise, they went for it.
After experimenting with several different formats, Dan started creating sketch comedy videos for TikTok, and it worked. Every morning he woke up, scanned that day’s business news, and chose a topic to parody on video.
In our interview, Dan talked about how he came up with the format, his daily routine for writing scripts, and Morning Brew’s strategy to grow beyond TikTok and launch new video series.
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If there’s one thing Twitter’s known for, it’s character limits. It famously only allowed 140 of them and then later expanded to 280. In some ways, that forced brevity made Twitter what it is today: a real-time commentary on what’s going on in the world.
But for years, Twitter has been trying to expand beyond its own character limits, first by launching features like photos, gifs, and videos. It launched a threading tool that allows you to string several tweets together. In 2021, it acquired newsletter platform Revue.
And then just recently, it debuted a new tool called Notes. Though it’s still in the testing phase, Notes will allow users to publish longer blog posts within their Twitter feed.
But is this something users actually want? Or will it eventually join the very large graveyard of social media features that never caught on?
To answer this question, I brought on Ernie Smith. Not only is Ernie one of the foremost experts on publishing platforms and newsletters, he also got early access to Twitter Notes and tested them out for himself. He gave me his initial reactions to the tool and we discussed whether it would usher in an era of longform writing to Twitter.
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When Nick Meacham first joined SportsPro in 2010, it mainly existed as a B2B print magazine that monetized through advertising. The editorial staff was tiny and it didn’t have much of a web presence.
But after taking over the business operations, he rapidly expanded it into new ventures – first by launching a series of lucrative conferences that targeted multiple industries within pro sports, and then by rapidly building out its digital operations.
In an interview, Nick explained to me why he made such a big bet on events, how the company adapted during the pandemic shutdown, and where he sees more opportunities to monetize the outlet’s digital content – including his plans to launch a subscription paywall.
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During their combined 20 years at The Wall Street Journal, Bradley Hope and Tom Wright covered some of the most momentous stories to hit the financial world, but none were as consequential to their personal careers as their reporting on Jho Low, a Wharton grad who was caught stealing billions of dollars from investment funds. Their dogged investigation led to the publication of the book Billion Dollar Whale, an instant bestseller that transformed them into A-list writers, on par with Michael Lewis and Malcolm Gladwell.
Rather than simply returning to their newspaper jobs, they partnered on a new media entity called Project Brazen. Unlike most digital media companies, Project Brazen has no ambitions to churn out large quantities of web content. Instead, it only focuses on ambitious, investigative storytelling that can be adapted into multiple mediums that include podcasts, books, film, and television.
How does Project Brazen go about vetting and staffing these projects, and what are the best ways to monetize serialized storytelling? Those are some of the questions I put to co-founder Bradley Hope in today’s interview.
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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.
Visit https://www.transizion.com/
There were a lot of media companies that were vulnerable to the pandemic shutdown, but perhaps none more so than Pop Up Magazine. Not only was its content delivered through live performances, but the hosts made special care during each event to tell the audience that nothing that night would be recorded. Part of the magic, in other words, was the show’s ephemerality.
Of course, there was no way Pop Up Magazine could continue delivering on that promise once all in-person events went away. Instead, it had to adapt by somehow taking the magic of a live performance and delivering it over the internet.
Not only did the magazine succeed in this endeavor, but the new restraints forced it to diversify revenue and expand its audience. With live events now returning, it’s arguably stronger than ever.
How did its staff accomplish this? In an interview last year, founder Chas Edwards walked me through Pop Up Magazine’s pivot, from the hellish first weeks of the pandemic to its recent return to live events.
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David Kushner had the kind of mainstream success that most writers dream of. His writing regularly appeared in glossy print magazines like Wired and Rolling Stone. Several of his books became national bestsellers. And his work has even been adapted into multiple TV shows and movies.
But in 2021, David decided to bypass legacy media entirely and start publishing his work to a Substack newsletter. What drove him to do this? In our discussion, David explained how the changing norms over IP rights and his own desire to experiment with serialized storytelling motivated him to make the move.
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When Patrick Trousdale launched his newsletter The Daily Upside in 2019, he didn’t have much of a personal brand to build from. In fact, even today, his personal Twitter account has fewer than 300 followers.
What he did have was several years of experience in finance and the willingness to grind out the newsletter each day, even when it didn’t have much of a following. That kind of persistence netted him his first few hundred followers, and it also helped him get his foot in the door so he could pitch The Motley Fool, a popular finance website, on a content partnership.
That partnership paid off in a big way, and The Daily Upside quickly grew by tens of thousands of signups. Today, the newsletter has over 300,000 subscribers and has sold out its ad inventory for months in advance.
In our interview, Patrick walked me through his initial launch strategy, his business model, and how he convinced editors at The Motley Fool to take a chance on a partnership with an unknown entity.
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When Adam White graduated from the University of Miami in 2017, he had every intention of getting a job in sports administration. In fact, he went through several rounds of interviews at a major organization and was sure he’d get an offer.
But the job never actually materialized, and instead of applying to more open positions, Adam decided to double down on Front Office Sports, a website he had founded during his freshman year in college. For the next year or so, he worked part-time jobs while also spending his mornings, nights, and weekends interviewing top executives at the largest sports franchises all around the world.
His bet paid off in a big way. Not only did he manage to secure angel investment, but the site also started to attract major sponsors. Today, Front Office Sports is a powerhouse in the B2B sports media space, and it’s using its momentum to expand into new verticals.
In my interview with Adam, he explained to me what sparked his initial idea, how he became a better interviewer, and why he’d rather embrace slow growth than accept large VC investment.
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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.
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.
After graduating from Harvard Law School in the early 2000s, Maria Brito was poised to have a successful career as a corporate lawyer. There was just one catch: she hated practicing corporate law.
Instead, her true passion was art. Throughout the early 2000s she started visiting New York galleries and even started to recommend pieces for purchase to her friends. Eventually, it dawned on her that high net worth individuals would pay her for the recommendations that she was giving out for free.
In 2009, Maria quit her law firm job and launched a new career as an art buying consultant. She also invested a significant portion of her time into creating online content, first with a blog and then later on social media. She eventually grew her audience to over 200,000 followers across Instagram, Facebook, Twitter, and email, and she’s leveraged this audience to sign book deals, run brand sponsorship campaigns, and bring in dozens of wealthy clients that include Gwyneth Paltrow and Sean "Diddy" Combs.
In a recent interview, she explained to me her content creation process, her philosophy on Instagram sponsorship deals, and why so many high net worth individuals trust her to buy art for their collections, often after seeing only a static iPhone photo of the piece she’s recommending for purchase.
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.
The Guardian recently announced it reached 1 million paying digital subscribers. What's most incredible about the accomplishment is that the newspaper reached that number without using a paywall. Does that mean that paywalls are overrated? I sat down with Ben Cohen, editor of The Banter, to discuss whether publishers should keep all their content free.
In 2014, Owen Walker faced a predicament. He was a sports scientist at a professional football club, and his manager asked him if they should buy expensive wearable technology that would help with the team’s training. Walker turned to the internet to research whether this kind of technology was effective, but he found there wasn’t much good sports science information online.
That realization eventually led to the launch of Science for Sport, one of the leading information hubs that translates peer-reviewed sports science for a lay audience. The outlet has been embraced as a resource by pro and college teams, and Owen recently sold it to one of the world’s largest sports technology companies.
In our interview, Owen walked me through how he built the site’s audience, his monetization strategies, and why he never focused on building his own personal brand.
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.
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.
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.
Google has a long and complicated relationship with news publishers. On the one hand, it sends billions of visitors to their websites every year through its main search engine, Google News, and other products. On the other hand, some publishers believe that the Mountain View company has siphoned away ad revenue on the back of their content.
Amy Adams Harding, Google’s director of analytics and revenue optimization for news and publishing, believes the search giant has the potential to provide a net benefit to publishers. Over the past several years, her team has developed a suite of tools aimed at helping media outlets to optimize their content so it reaches a bigger audience and drives more revenue.
In our interview, Amy walked me through these tools and explained how they work. She also talked about why publishers need to adopt many of the strategies that ecommerce platforms developed over a decade ago.
Snigdha Sur’s first idea for a media startup was a kind of Netflix-for-Bollywood streaming service, but when she spoke to investors about the idea, they all pointed out that it would be too easy for Netflix to simply copy her strategy.
Though she quickly scrapped that idea, she still wanted to launch some sort of outlet that would service South Asian Americans, a group that she felt was underrepresented in mainstream media. This led to the launch of a free weekly newsletter that amassed several hundred readers.
That free newsletter eventually evolved into The Juggernaut, a subscription-funded publisher that has a dedicated and growing fan base. I interviewed Snigdha about how she convinced YCombinator to let in a media startup, why she launched a hard paywall, and whether she’ll ever introduce advertising into her revenue mix.
Most subscription strategies have a pretty straightforward value exchange: in exchange for a monthly payment, the subscriber gains access to premium content that’s locked behind some kind of paywall.
But what if you want to keep all your best content in front of the paywall? What could you still offer to your audience to make a monthly subscription payment worth the price of admission?
Thousands of content creators have turned to platforms like Subtext, a tool that allows them to exchange text messages with their fans. Creators can either send mass texts out to their entire audience or get into individual conversations with subscribers.
I’ve tried out the tool myself, and it’s truly innovative. For this episode, I spoke to Subtext CEO Mike Donoghue. We talked about how his team developed the application and the different ways creators use it to generate revenue.
Most major media companies are focused on scale. They want to reach ever larger audiences and then leverage that reach to drive more revenue. To accomplish this, they invest time and resources to create content across all major social platforms, from YouTube to TikTok to Snapchat.
The Art of Manliness isn’t that kind of media company. Let me give you an example of what I mean: it managed to build its YouTube channel to 1.2 million subscribers, an impressive feat, only to mostly abandon the channel several years ago. In a 2017 video, founder Brett McKay explained that there were other projects he’d rather devote his time to -- projects like writing a book, lifting weights, and producing his podcast.
According to Jeremy Anderberg, the Art of Manliness’s managing editor and one of only three full time employees, this kind of narrow focus is part of the company’s ethos. It purposefully didn’t try to scale like the BuzzFeeds and Vox Medias of the world. Instead, its team devotes nearly all of its energy into writing articles and producing a podcast, the latter of which has an incredibly loyal audience. That audience is so loyal that thousands have signed up for a 12-week bootcamp the company runs for “those who wish to revolt against our age of ease, comfort, and existential weightlessness.”
Anderberg spoke to me about how The Art of Manliness built its audience, why it launched its bootcamp, and what it’s like to work for a media company that purposefully stays small.
In the spirit of Mental Floss’s 20th anniversary, let me give you a few pieces of trivia about the magazine. It made a cameo in two episodes of Friends and an episode of Netflix’s The OA. It started as a print magazine but discontinued its print edition in 2016. In addition to its web content, it produces several popular video series on YouTube. And in 2018, it was acquired by Minute Media, a conglomerate that mostly consists of sports media sites.
Suffice it to say, the Mental Floss of 2020 looks a lot different than when it was a magazine published out of the dorm room of two Duke University students. I recently sat down with its editor in chief Erin McCarthy to talk about its post-print strategy and why a sports media company was interested in a publisher that specializes in history trivia.
By the time Richard Rushfield launched his newsletter The Ankler in 2017, he had held journalism jobs at several major media companies that included The Los Angeles Times, BuzzFeed, and Gawker. But because he served as a behind-the-scenes editor in most of these roles, he didn’t have much of a personal brand to speak of, which meant he needed to build a newsletter readership from the ground up.
Despite these headwinds, Richard managed to replace his full-time salary within about two years, and The Ankler is now a must-read for virtually every Hollywood studio executive. In our interview, he explained how he built his audience and why he prefers his life as an independent writer much more than his past career as a traditional journalist.
If you’re in the media, then you’re probably aware of The Daily, the massively successful podcast produced by The New York Times. It now receives over 4 million downloads a day and generates eight figures in revenue for the newspaper.
But is it possible to replicate The Daily’s success without the institutional support? That’s the question Jamie East set out to answer. A year ago, he and a few colleagues launched The Smart 7, a 7-minute podcast that’s published each weekday at 7 a.m. Its relatively simple format and consistency made it easy for listeners to build it into their daily habits, and within its first year it hit five million downloads.
I recently interviewed Jamie about why he struck off into indie podcasting when he already had a successful career in traditional broadcasting, and he explained how he plans to build an entire network of niche daily podcasts.
If you look at the Apple and Spotify podcast charts that track the most downloaded shows every week, you’ll notice that many of the most popular podcasts belong to large networks. Organizations like Gimlet Media, Wondery, and NPR are able to pool their resources to promote their content, and this gives their shows a distinct advantage over independent podcasts, even those of similar quality.
That’s why some indie podcasters have formed collectives. These entities provide many of the same benefits of a network while still allowing for the podcaster to own their intellectual property. To get a better perspective how these collectives work, I interviewed Amanda McLoughlin, the founder of a collective called Multitude.
In our interview, Amanda explained her process for recruiting shows to join Multitude, the collective’s business model, and why podcasters shouldn’t be timid about asking their audience for financial support.
David Harper wrote hundreds of thousands of words over a five-year period without making a single penny from his comic book criticism. In 2009, he and a couple friends launched Multiversity Comics, a fan website that went on to be nominated for an Eisner Award, which is basically the comic book equivalent of an Oscar.
In 2015, David struck off on his own, launching an incredibly popular podcast and website. As his audience grew, he began to think about ways he could monetize it, and he eventually rolled out a paid subscription model. In my interview with David, we talked about the origin of his comic book fandom, where he found his audience, and how he designed his subscription offering.
Every morning, tens of thousands of people who live in cities like Miami, Portland, and Pittsburg receive a conversational email that updates them on the latest news within their city. These newsletters don’t often contain any original reporting, but they’ve been embraced by their local communities because they’re so effective at distilling dozens of newspaper articles, social media posts, and government announcements into an easy-to-read digest.
These newsletters are owned and operated by a company WhereBy.US. Launched in 2014, the company built out a scalable model that includes newsletters, self-service ads, and paid memberships. I recently interviewed its founder Christopher Sopher about how he built the company, its role within local journalism, and why he decided to spin off a SaaS publishing product that he sells to other media entrepreneurs.
Daniel Orubo had no intention of becoming a media personality when he graduated with an engineering degree in 2013, but his funny tweets just happened to catch the eye of a Nigerian publishing executive who planned to launch a BuzzFeed-like website called Zikoko.
Daniel started out as a senior writer, crafting humorous listicles like the “12 characteristics of Nigerian mothers,” but over the next half decade he helped transform Zikoko into a cultural force that’s willing to discuss hot-button issues around sexuality -- the kind of issues that are typically considered taboo in conservative Nigeria.
Daniel is now the editor-in-chief of Zikoko, and we recently sat down to discuss how the website found its audience and why it expanded beyond funny memes so it could tackle controversial topics.
These days, nearly every digital publisher utilizes some kind of reader revenue strategy, but when Jessica Lessin quit her Wall Street Journal job and launched The Information in 2013, it was still a novel concept. At that time, the paywalls that existed were usually metered, but Jessica was among the first to place her website’s entire library of content behind a hard paywall. If you wanted to access to any of its articles, you needed to fork over up to $400 a year for the privilege.
In our interview, I asked Jessica about why she chose that model, how her journalists compete with much larger publishers for scoops, and what marketing strategies drive the most paid conversions.
https://simonowens.substack.com/
I just passed my one-year anniversary of launching my paid newsletter, so I decided to dive into some of the biggest lessons I learned during that time.
If you review Kevin Jones’s resume on LinkedIn, it’s easy to see why he ended up founding a sports podcast network. He’s worked in virtually every sector of the sports media industry, from creating content for pro football teams to reporting for traditional radio stations to writing for sports news sites. He also launched Striking Gold, a 49ers-focused podcast that eventually accrued several thousand listeners.
But Kevin wasn’t content with simply being a podcast personality. Back in 2018, he began to notice that there were a lot of people like him -- podcasters with extremely passionate fan bases but no way to convert that fandom into actual revenue. So he began pitching them one by one on joining Blue Wire Podcasts, a network that would help them produce their shows and sell advertising in exchange for a cut of the revenue.
Flash forward two years, and Blue Wire has since taken on several million dollars in investment, is now producing narrative documentary podcasts, and recently signed a huge deal with one of Las Vegas’ biggest hotels.
I recently sat down with Kevin to discuss how he convinced podcasters to join his network, his approach to working with talent, and why he’s doubling down on longform narrative series.
Over the past year, thousands of journalists have announced the launch of their paid newsletters, which are often hosted on platforms like Substack. Writers with already-existing large audiences have seen immense success with this strategy, pulling in six figures incomes within weeks of debuting their new newsletters.
But the vast majority of writers don’t have huge Twitter followings to promote their newsletters to. For them, growing a sustainable media business can take years of work, and many don’t have enough savings in the bank to hold out for that long.
That’s why we’re seeing a new trend in which writers team up to launch bundled subscriptions. This approach allows writers to cross pollinate their audience growth and ramp up content production to make a subscription much more worthwhile. Publications that include Defector, the Discourse Blog, Brickhouse, and Every have seen tremendous success with this model.
To understand how these writer cooperatives work, I spoke to Mark Stenberg. Stenberg runs his own Substack newsletter and has spent the last few months reporting on the creator economy for Business Insider. He recently moved over to Adweek to cover the media beat.
The last 15 years have not been kind to the local news industry, with thousands of newspapers either reducing staff or closing down entirely. But not all newspapers have been affected equally, and some of the hardest hit chains were owned by hedge funds and private equity firms that had no actual interest in investing in journalism.
Family-owned newspapers seemed to have fared better, and that seems to be the case for Forum Communications, a chain of newspapers and other media outlets situated in the midwest. A few years ago, the company’s newspapers rolled out a digital subscription model, and so far it seems to be performing above expectations.
I recently interviewed Stephanie Schroeder, Forum’s Chief Digital Marketing Officer, about the gargantuan amount of work that went into this pivot and what strategies resulted in the most success.
According to some estimates, corporations across the world spend upwards of $42 billion a year on content marketing, and they do so with the philosophy that by acting like media companies, they can engender trust with potential customers and drive sales.
One of the people who helped sell the corporate world on this marketing philosophy is Joe Pulizzi. In 2007, Joe founded the Content Marketing Institute, and through its constellation of articles, videos, courses, and conferences, it convinced thousands of executives that the frictionless distribution of the internet allowed virtually everyone to become a media company.
I recently interviewed Joe about his journey. We discussed whether freelance journalists should take on content marketing gigs, which companies have been particularly good at content marketing, and whether we’re currently in a content bubble.
Like a lot of people on the political Left, Geoff Sharpe grew frustrated by how successful conservatives were on Facebook. For years, he watched as right leaning conservative groups built huge Facebook followings, which allowed them to promote their highly partisan views to millions of Canadian citizens.
So Geoff and his colleagues decided to do something about it. They initially launched their own left-leaning Facebook page, growing it to hundreds of thousands of followers. But they then wanted to pivot to something even more ambitious: a standalone website that published original content from leading progressive voices.
To do this, they launched a crowdfunding campaign, and over the last year they’ve rolled out a membership offering that helps generate recurring revenue. I interviewed Geoff about why the political Right does so well on Facebook, how he designed the membership program, and what impact his site has had on Canadian politics.
There’s a common misperception that many non-lawyers have about how legal contracts are written. Most people probably assume that a lawyer writes each contract from scratch, but in reality the lawyer is most likely copy and pasting clauses and sections from already-existing contracts and modifying them for their particular client.
One of the resources lawyers often turn to for this is Law Insider. Founded in 2010, Law Insider indexes the millions of contracts that have been uploaded to the SEC website by publicly traded companies. It generates over 4 million monthly pageviews and has over 250,000 registered users, about 5,000 of which pay $30 a month to access its archives.
I recently interviewed the site’s co-founder Preston Clark about how he and his partner came up with the idea, what they did to build up its massive audience, and why they’re expanding into a full-fledged media company that produces everything from articles to YouTube videos.
Over the past year, dozens of writers have left their mainstream media jobs to launch their own standalone newsletters and publications. In almost every case, the writer monetized his content through paid subscriptions, usually with a tool like Substack.
Rick Ellis never bothered with paid subscriptions. Instead, his website AllYourScreens.com generates so much traffic each month that he’s able to make a good living mostly through programmatic advertising.
Ellis has been operating AllYourScreens.com off and on since the early 2000s, but a few years ago he decided to abandon traditional media completely to focus on the site full-time. I recently interviewed him about how he found his audience, what his weekly writing schedule looks like, and why he has no interest in building out a paid subscription business.
Max Rofagha didn’t have a background in media prior to launching Finimize. He also didn’t have a background in finance for that matter. It was while conducting research on how to manage his own investments that he saw an opportunity for a daily newsletter aimed at helping millennials become more literate in finance.
Flash forward four years and Finimize now has over 1 million subscribers, a staff of financial analysts, and a worldwide community of young professionals who often meet up for in-person events.
I recently interviewed Max about his early audience development strategy, how his subscribers organize their own in-person events, and why he decided to launch a subscription-funded mobile app.
Per Grankvist had the kind of media career most journalists only dream of. He was a high-profile columnist for a leading newspaper and a regular face on one of Sweden’s top broadcast networks. But over time he grew disillusioned with mainstream media and its tendency to dumb down coverage of complicated policy issues.
So Per quit his traditional media jobs and launched his own outlet. It started with just an Instagram account that explained thorny election issues, but from there it blossomed into an entire media outlet that spanned across social media, podcasts, and newsletters.
I recently interviewed Per about how he built the company, his approach to monetization, and whether he misses working for mainstream media publications.
Peruse a newsstand full of men’s magazines and you’ll probably notice a few common themes. The cover either features a bikini model or a suit-clad male celebrity. Inside, you’ll find stories meant to appeal to what many in the mid-20th century would have considered the “ideal” man -- articles about scotch, cigars, and custom suits.
You won’t find many of those kinds of features in MEL Magazine, a digital-only publication that launched in 2015. Owned and operated by Dollar Shave Club, MEL aims its content at the under-40, educated, likely-urban male...a man less inclined to traditional gender roles who is much more in touch with his feelings and spends an inordinate amount of time on the internet.
I recently interviewed editor-in-chief Josh Schollmeyer about how he came to define this 21st century male, where his staff sources its article ideas, and how Dollar Shave Club will profit from its investment in the magazine.
Lon Seidman didn’t launch on YouTube with the goal of becoming a top gadget reviewer. In fact, he stumbled upon that aspect of his career while struggling to run a video local news startup in Connecticut. Almost on a whim, he recorded a video review about one of the cameras he bought for his startup, and to his surprise, the video blew up.
Flash forward a decade, and Lon now has tens of millions of views across YouTube and Amazon. He managed to carve out a niche among a crowded field of gadget reviewers, and he’s now making a pretty good living through a mixture of YouTube advertising, affiliate sales, and Patreon subscriptions. We walked through how he accomplished all this in our interview.
If you had to make a list of technologies that are most important to the average person’s day-to-day life, data centers would sit near the top of that list, and yet chances are you know very little about them. There are a few reasons for this. For one, they’re not sexy in the way that an iPhone or a cutting-edge drone is sexy. But also the people and companies who run data centers are fairly secretive, mostly to protect their machines from any sort of attack.
This combination of secrecy and obscurity has made Rich Miller’s expertise very lucrative. He’s spent the last two decades covering data center tech for various news outlets he’s owned. His current site, Data Center Frontier, is a must-read for anyone working in the $60 billion+ industry.
I interviewed Rich about how he accidentally fell into the beat, why he sold his first data center site, and what made him want to start a brand new one from scratch.
Back in late 2019, nearly all the writers for the beloved sports site Deadspin resigned en masse after butting heads with the private equity executives who owned the website.
After they left, there was lots of speculation about where those writers would turn up. Would they simply get new jobs, or would they band together to create their own site?
And then in July 2020 we got our answer: they launched Defector, an employee-owned publication that would be monetized mostly through paid subscriptions. To build the site, they turned to a guy named Austin Smith. Austin is the founder of an agency called Alley Interactive, and over the past decade he’s helped build and maintain the websites of many of the most well-known news publishers in the world.
I sat down and interviewed Austin about his career in media, what goes into building a good publishing platform, and why he’s recently begun working with news startups like Defector to help them get off the ground.
Abby Glassenberg runs a trade association called the Craft Industry Alliance. It has over 1,600 paying members who work in the arts and crafts industry. It hosts conferences, schedules networking events, publishes industry news, and provides ongoing education. Pretty much the kind of services that most trade associations offer.
But unlike most trade associations, this one grew out of a one-person blog. Abby started it as a hobby, but it soon amassed a large audience, which then led to a book deal, a thriving Etsy store, and a popular podcast.
I recently interviewed Abby about why she went the trade association route and how she’s growing its revenue by 20% a month.
In just about every article about TikTok, it’s portrayed as a video repository created by and for teens. Indeed, nearly every single one of its top-earning creators are under the age of 20, and polls have found that it ranks second only to Snapchat as U.S. teens’ favorite social media app.
Zarna Garg is an exception to the rule in multiple ways. For one, she’s a 45-year-old mom who barely even knew TikTok existed a year ago. And while most top users traffic in dance videos, lip syncs, and comedy sketches, Zarna’s specialty is standup comedy. Many of her jokes aim to capture the South Asian immigrant experience, and she says she’s carved out a niche explored by very few comedians, both inside the U.S. and in India.
I interviewed Zarna about how she cracked the TikTok algorithm, what impact her success has had on her comedy career, and how she’s leveraging that success to try to break into Hollywood.
If you traveled back in time 100 years and perused your average newsstand, you’d find dozens of magazines that published serialized fiction. Millions of subscribers eagerly awaited new installments from their favorite authors, and a serialized story in a high circulation magazine could launch a new writer’s career.
But by the turn of the century, serialized fiction was all but gone. Or at least it was in written and audio form. TV shows, on the other hand, began to adopt complex, serialized narratives, and by 2015 these kinds of shows were dominating both online and offline discussion. That’s the same year a new app called Serial Box launched.
Serial Box operates a lot like a TV studio. Its stories are delivered in weekly installments. Each series is written by a collaborative writers room. The most successful series will often continue for multiple seasons. There’s only one major difference: instead of producing TV shows, Serial Box publishes text and audio stories that could be read or listened to in the same way you consume a novel.
I recently interviewed co-founder Molly Barton about Serial Box’s origin story, how the company produces new series, and why she’s pursuing adaptations outside of the Serial Box app.
Polina Marinova had the kind of media career that many journalists dream of. After a brief stint at a media startup, she landed a job at Fortune Magazine and eventually got the role of head writer for Term Sheet, its daily newsletter on deals and dealmakers. After six years there, her resume and profile probably could have gotten her any mainstream media job she wanted.
But instead, she left that steady job in March -- in the beginning of a massive recession -- to focus on her Substack newsletter full-time. The newsletter is called The Profile, and though she was running it as a side hustle while working at Fortune, she didn’t debut the paid version until after she left.
I recently interviewed Polina about why she decided to make the jump during such uncertain economic times, how she differentiates the free from the paid content, and her strategy for growing the newsletter’s audience these past six months.
My newsletter: https://simonowens.substack.com/
So the format to this podcast is pretty straightforward and consistent. I bring on a media entrepreneur or executive and interview them about their craft. But I’m also sort of a media entrepreneur myself, in that six months ago I launched a paid Substack newsletter that I hope to grow into a full-time job.
Growth has been slow but steady, and over the six-month period I’ve experimented with a number of strategies to boost signups. Some worked, others didn’t.
I’ve still got a ways to go before it’s completely replaced my consulting income, but I think I’ve made enough progress that it’s worth pausing and looking back at some of the lessons I’ve learned along the way.
So strap yourself in, because we’re about to dive deep on my paid newsletter strategy.
With the journalism industry in freefall, there’s a good chance that your local newspaper is experimenting with some kind of digital subscription offering. In many cases, this involves some kind of metered paywall where you’re expected to start paying after consuming a pre-determined number of articles. Hundreds of newspapers have installed paywalls like this, but they’ve seen mixed results, with many reporting disappointing revenue numbers.
But is content the only thing an audience will pay for? That’s a question Doug Lesmerises, a Cleveland.com sports columnist, sought to answer. A few years ago he co-founded a popular sports podcast but had a difficult time attracting advertisers. Then some executives from his newspaper’s parent company approached him with a new product called Subtext. It provides a simple way to allow paying subscribers to exchange text messages with Doug and other hosts.
The service was a surprise hit, and Doug now uses the app to crowdsource questions for the podcast and send his paying subscribers quick-hit analysis when Ohio sports news breaks. I interviewed Doug about how he incorporated texting into his show and what other local journalism outfits can learn from his success.
When Naoise McNally and her business partner launched One Fab Day, neither of them had any experience working for a media company. Naoise didn’t even have much knowledge of the wedding industry outside of planning her own wedding. But the lack of wedding-focused internet resources in Ireland presented a clear market opportunity, so they went for it.
Flash forward several years, and the site now has a full time staff and an interesting business model. Instead of relying on traditional advertising, it charges wedding vendors to be listed in an index it curates for readers.
I recently interviewed Naoise about One Fab Day’s founding, how she settled on a business model, and what she hopes the site can accomplish now that it’s owned by a major media company.
Quick question: how big do you think the global freight industry is? If your guess is in the billions, then you’re aiming too low. According to some estimates, global logistics generate somewhere in the range of $8 and $12 trillion annually.
For Craig Fuller, that number represents a massive opportunity. His company Freight Waves covers this industry across text, video, and podcasts. But Freight Waves is a lot more than just a trade publication; it also delivers data and intelligence. In fact, it’s much more analogous to a Bloomberg LP, which in addition to its massive media business also generates billions of dollars a year from its expensive Bloomberg terminals.
I interviewed Craig about how he built his expertise in freight, where the company sources its data, and why it recently took on venture capital investment.
When Terrell Johnson launched on Substack, he had no intention of rolling out a paid newsletter. He was just trying to escape Mailchimp’s expensive fees and liked that Substack would send his newsletter for free. About a decade earlier, Terrell had created HalfMarathons.net, a running focused website that grew so popular that at one point it was generating six figures in revenue just from Google Adsense.
His free newsletter served mostly as a form of marketing for the website, but he eventually began to wonder if his most engaged readers would be willing to pay for it. So he flipped on Substack’s payment features, and while it wasn’t an overnight success, he’s gradually grown it into an impressive community of paid subscribers.
I interviewed Terrell about where he got the idea for HalfMarathons.net, how he built up an audience, and why he eventually grew to distrust Google as his primary traffic driver.
Josh Spector was blogging before most people even knew what a blog was. Over the span of a decade, he started and abandoned several of them, often before they had a chance to amass much of an audience. But in 2011 he got more serious about audience growth for a blog he ran that focused on teaching standup comedians how to market themselves, and to help drive traffic to it he launched a newsletter.
Pretty quickly, he grew addicted to the newsletter medium, and a few years later he merged a couple of newsletters he was running into a single list and renamed it For the Interested. Since 2016, he’s been sending out new issues each week featuring ideas to help creators to produce, promote, and profit from their creations. For the Interested now has over 25,000 subscribers, and Josh recently launched a paid spinoff newsletter.
I recently interviewed Josh about how he grew his audience, the role his newsletter plays in his consulting business, and why he thinks so many writers are approaching paid newsletters the wrong way.
A year ago, Jesse Singal had a very traditional freelance writing career. When he wasn’t working on his book, he’d write articles for places like The Atlantic and New York magazine. The mixture of book advance and freelance revenue provided a reasonably stable income.
Today, the economic climate for journalism is much more dire. The Covid-induced recession has led to mass layoffs and a squeeze on freelancer budgets. Some publications have closed up shop completely. But in many ways, Jesse’s income streams are more secure than ever. That’s because he launched a paid newsletter through Substack and co-hosts a hit podcast that monetizes through Patreon. Together, these two sources generate a nice six-figure income for him.
I recently interviewed Jesse about why he decided to monetize his audience directly, how he designed his paid offerings, and whether he thinks platforms like Substack and Patreon can replace the income for laid-off and underemployed journalists.
When Tyler Morin was in high school, he dreamed of going into journalism, but his parents convinced him to major in finance instead. After graduating, he went into the financial sector, but he never lost his ambition to work in media, and he became obsessed with daily newsletters like Morning Brew and theSkimm. After experimenting with a group sports blog, he pivoted to launching a daily newsletter called The Water Coolest.
The Water Coolest found an audience and quickly grew to tens of thousands of subscribers. I recently interviewed Tyler about the founding of his company, how he found his first advertisers, and why he decided to launch a paid version.
Arlington Country, Virginia is a suburb of DC. It has over 236,000 residents, thousands of local businesses, and an average household income north of $100,000. With those sorts of attributes, you’d think it would have a vibrant daily newspaper, but instead its citizens mostly rely on the Washington Post metro section and a few weekly newspapers to get their news.
Or at least that’s all they had up until about a decade ago. In January 2010, a former TV news producer named Scott Brodbeck launched Arlington Now, an online only news site dedicated specifically to Arlington. It quickly grew an audience and revenue base, and Scott has since launched several other sites covering Northern Virginia.
I recently interviewed Scott about the founding of Arlington Now, how his journalists approach their coverage, and why he doesn’t consider Google and Facebook to be much of a threat to his advertising revenue.
Dan Oshinsky didn’t apply for an open position to run BuzzFeed’s newsletter operations. He just happened to reach out to editor Ben Smith back when BuzzFeed was hiring a bunch of people with weird internet obsessions, and the company hired him without a clearly defined role.
This dynamic granted Dan a lot of leeway in terms of how he approached BuzzFeed’s newsletters, and he went on to launch several products, including multiple online courses and the newsletter This Week In Cats. A few years later he got hired to run newsletters at The New Yorker, which was focused on building out its paid digital subscriptions. Recently, he left that job to run his own newsletter consultancy.
I recently interviewed Dan about how he built out BuzzFeed’s newsletter strategy, the role of newsletters in driving paid subscriptions, and why he left such a prestigious job to strike off on his own.
The audiobook market is massive, with sales projected to hit $3.5 billion this year. What used to be a niche, expensive product is now one of the fastest growing mediums. In fact, The New York Times recently reported that audiobooks are one of the only book formats still growing in sales during the current pandemic-induced recession.
But what does it take to launch a hit audiobook? How does the choice in narrator influence sales? And are book publishers worried about the market dominance of Amazon-owned Audible? These are all questions I put to Scott Dickey, the CEO of a company called Podium Audio.
Podium is an audiobook studio that specializes in signing deals with self-published authors. It was the studio that produced the audiobook version of The Martian, the book that was made into a hit film starring Matt Damon.
In the mid-2000s, Digg was one of the most powerful websites on the internet. Powered by its army of users, the platform would send gargantuan amounts of server-crushing traffic to any content featured on its front page. Millions of people visited it each day and it turned its founder Kevin Rose into an internet celebrity.
But you probably know what came next. A misguided redesign triggered a user revolt, and its audience abandoned it for Reddit and other platforms. Before long, it seemed destined to follow in the footsteps of Myspace and Friendster.
Its story didn’t end there. In 2012, the site sold to the startup studio Betaworks, which immediately went about trying to revive the Digg brand. In 2018, it was purchased by a company called BuySellAds.
I recently interviewed Todd Garland, Digg’s new owner and CEO. We discussed its current editorial operations, its monetization strategy, and his plans to restore Digg to its former glory.
I first discovered Gil Assayas, the musician otherwise known as GLASYS, when one of his YouTube videos made it to the front page Reddit. His amazing keyboard set up and sophisticated musical adaptations of well-known video game soundtracks caught the attention of several gamer subcultures, who then shared his videos widely across social media.
I recently sat down with Gil and asked him about how he grew his fanbase and in what ways his viral videos have translated into career success.
The New York Times gets a lot of credit within the media industry for the blockbuster success of its podcast The Daily, but The Los Angeles Times was also an early pioneer within the medium. Its narrative true crime podcast Dirty John generated over 30 million downloads and was adapted into a TV show for Bravo. The newspaper has since gone on to launch ambitious shows chronicling the criminal trial of Bill Cosby and the famous murders committed by Betty Broderick.
I recently interviewed Clint Schaff, VP of strategy and development, about the paper’s podcast productions. He walked me through how shows get made, their monetization strategy, and his views on selling IP to TV studios and Spotify.
Jono Dry is the type of artist whose work is sold in European galleries by art dealers. He only finishes a few pieces a year, and most of his purchased pieces likely reside in the private collections of rich people, closed off from the public.
But that hasn’t stopped millions of people from viewing his work. That’s because Jono films himself drawing each piece and uploads gorgeous time-lapse videos to platforms like Facebook, Instagram, and YouTube. On YouTube alone these videos have generated over 8 million views, and his success on social media has transformed him into a world-famous artist.
I recently interviewed Jono about how he built his following and in what ways he’s been able to leverage that following to advance his career.
We’ve seen several media companies launch over the past few years that specialize in sending out newsletters that summarize each day’s news. Newsletters like theSkimm, The Hustle, and Morning Brew speak to their readers in a conversational style and have been embraced by millions of loyal subscribers.
The folks behind 6AM City took that model and applied it to local news. Operating out of cities like Greenville, SC and Chattanooga, TN, each newsletter mines local newspapers, businesses, and social media accounts to produce a daily snapshot of the goings on in that urban center. To date, it’s grown to over 230,000 subscribers and monetizes primarily through custom, native ads.
I recently interviewed co-founder Ryan Johnston about how each newsletter operates and whether he thinks his company is producing quality local news.
Ben Cohen isn’t the world’s biggest fan of Facebook. The founder of a political news website called The Daily Banter, Ben worked hard to build up his reach on Facebook, and for a few years he made a decent living selling advertising against his content.
But after the 2016 election, Facebook pivoted away from news, and virtually overnight The Daily Banter lost 90% of its traffic. Not only could he no longer pay his own salary, but he was also struggling to keep his stable of writers on board.
Out of desperation, he moved the Banter over to Substack and doubled down on paid subscriptions. That was in early 2019. I recently checked in with Ben to see how his efforts are going and how a presidential election year affects subscription growth for a political newsletter.
Alexis Grant didn’t start her career with the goal of building several media businesses. She simply wanted work as a reporter. After college, she got a job at the Houston Chronicle and then later accepted a role editing the careers section at US News & World Report.
But something about the business of media intrigued her, and while at US News & World Report she launched a side hustle running social media and blogs for corporate clients. Eventually, she drummed up enough business to quit her day job and focus on content marketing full time. In fact, she launched an entire marketing agency that specialized in producing branded content.
One of her clients was a personal finance website called The Penny Hoarder, and she was so successful at growing its audience that the company eventually acquired her agency and installed her as its editor in chief. By the time she left The Penny Hoarder a few years later, it was generating tens of millions of dollars in annual revenue.
I recently interviewed Alexis about how she helped scale these companies and what she plans to do next.
Because I write and podcast so much about the business of media, I regularly get emails from founders of niche media companies who want to tell me about their successful ventures. A few months ago, I received an email from a guy who identified himself only as Meathead, and after reading only a few paragraphs I knew I wanted to have him as a guest for my podcast.
Meathead, who’s been writing about food on the internet since the days of dial-up AOL, started the website AmazinRibs.com almost as a lark. Flash forward 15 years, and it’s the preeminent authority on all things barbecue. It generates a healthy mix of revenue from advertising, affiliate sales, books, and paid subscriptions, and it grew its business without help from any venture backing.
I recently interviewed Meathead about writing for AOL when it was the biggest game in town, running the third most popular wine magazine, and stumbling into a website venture that made him one of the most famous people within the barbecue scene.
If you wanted to become a professional standup comedian in the 1990s, the path was pretty straightforward. You started by going to amateur open mic nights, where you would hone your act. Eventually, you’d develop five to 10 minutes of solid material and maybe get a slot opening for a bigger comedian. From there you’d work yourself up to bigger and bigger gigs, and if you were really talented and lucky, you’d land a slot on a late-night talk show, or, even better, get signed to an hour-long special for HBO.
These days, the path for the aspiring comedian is completely different. Sure, there’s still the open mic nights and the club gigs. But there’s also a bevvy of online platforms that you can leverage to sharpen your craft and build a following. You might collaborate with other comedians and write sketches for a YouTube channel. You can practice your one-liners on Twitter. And you’ll definitely want to launch a podcast.
As a full-time standup comedian, Joel Byars has employed several of these strategies. I interviewed Byars about how comedians market themselves in this golden age of standup comedy and asked him why he decided to self-produce his own comedy special.
Let’s say you’re a writer who wants to publish your work to the web and eventually monetize it. These days you have plenty of options. You might open a Medium account and join the platform’s partner program. Or maybe you launch a Substack newsletter. If you’re really ambitious, you could throw together a Wordpress website and integrate it with a payment tool like Stripe.
Or you could just launch an account on Ghost, a publishing platform created a few years ago by a guy named John O’Nolan. Before founding Ghost, John was the deputy head of design at Wordpress, and though he was always a fan of the open source CMS, he thought he could create something a little bit better.
So John launched a Kickstarter campaign, and after raising tens of thousands of dollars, he developed Ghost. Today, it’s used by some of the world’s largest brands, and his hope now is that independent writers will use it to monetize their content. I spoke to John about the platform and why he thinks a writer should choose it over a competitor like Substack or Patreon.
When we talk about the media industry, we’re usually discussing publishers that are geared toward a broad audience -- outlets like The New York Times or CNN or NPR. Even more niche publications like The Verge or Bon Appetit are designed to attract tens of millions of readers each month.
But there’s also an entire ecosystem of business-oriented publishers that operate in extremely narrow niches -- outlets aimed at sewage workers, electricians, and grocery store executives. Though their readerships are relatively small, they represent industries that collectively generate hundreds of billions of dollars each year. Because of this, B2B niche publishers, when run well, can be immensely profitable.
Industry Dive is one such B2B publisher. Founded in 2012, the company now produces publications that cover over a dozen industries. I sat down with one of its co-founders Sean Griffey to talk about Industry Dive’s origin story and how it bootstrapped its way to north of $22 million in annual revenue.
BuzzFeed CEO Jonah Peretti has expressed a lot of frustration with the large platforms that dominate our online browsing. In 2018, for instance, he complained that Facebook captures a lot of value from publishers and argued that it should share more of its revenue with them. That same year, he floated a merger of several digital media companies so they’d have more bargaining power against the platforms.
And then recently he wrote a memo in which he lamented that publishers didn’t receive enough credit for the consumer purchases they drive. “The two most important players in this chain are the publisher who inspired a consumer to take action and the companies that actually deliver the product But most of the profit is captured by digital middlemen who didn’t create much value.” In the memo, he promised that BuzzFeed was working hard to solve this attribution problem.
To get an idea of how BuzzFeed plans to solve this problem, I recently spoke to Rich Reid, its senior vice president of global content. We talked about Bring Me, BuzzFeed’s travel vertical that publishes a wide range of video and text content across its website and social channels. Recently, Bring Me formed an ad partnership with Hilton, and I asked Reid about how his team designed the campaign so that BuzzFeed gets full credit for any business it sends Hilton’s way.
It’s been nearly a decade since The New York Times launched its metered paywall, and its success has spurred just about every digital publisher to test out some form of reader revenue strategy. Many have followed in the Times’s footsteps and debuted metered paywalls. Others have rolled out various membership options, offering everything from behind-the-scenes footage to exclusive commenting features to convince readers to open their wallets.
But which tactics actually work? And how should publishers determine what to charge? To answer these questions, I spoke to Jacob Donnely. Donnely is the managing director of audience and growth at Coindesk, one of the leading cryptocurrency publishers, and runs his own paid newsletter about the publishing industry. We talked about how to design the perfect subscription offering and debated whether subscription fatigue is actually real.
In its most recent earnings report, Twitter revealed that it has over 139 million daily users, but the company’s first podcast it launched in 2019 was designed to only appeal to a tiny fraction of those users. The show is called Character Count and is hosted by Joe Wadlington, a creative lead in the department that helps educate small businesses on how to leverage Twitter in their marketing.
And that’s the focus of Character Count, highlighting some of the most effective ways in which businesses utilize Twitter. Recent guests have worked for Dungeons and Dragons, Grindr, and Dropbox.
I recently interviewed Wadlington about his podcast strategy and the role the show plays in helping improve Twitter’s bottom line.
Where you can subscribe to my newsletter: https://simonowens.substack.com/p/discount
So this is the 68th episode of my podcast, and if you’ve been listening to it for any amount of time, you’d know that it never has ads. And while I don’t have anything against podcasts that have advertising, I don’t envision a future for this podcast where I’m reading promos for Squarespace of Mailchimp.
But at the same time, I’d like for this podcast to contribute to my income, mostly so I can justify spending more time on it. During a good month, I might put out a new episode each week, but I’ve had busy months where I was lucky if I could produce more than a single episode.
If I can start making money from this podcast, then it’ll be easier for me to justify spending more time on it, and then everyone gets to benefit.
And I didn’t want to do just a quick promo and then be done with it. Given that most of my listeners actually care about business models for content, I wanted to go deep on my decision making process, and to do that I enlisted the help of my friend Jaclyn Schiff.
Jaclyn is a content expert like me who specializes in converting podcast episodes into shareable articles for clients. You can find her work at podreacher.com.
She recently interviewed me about my history covering the business of content and how I came up with my monetization strategy.
There are few people as knowledgeable about web publishing as Scott Rosenberg. In 1995, he and a group of other San Francisco Examiner journalists launched Salon.com, one of the first online magazines. An early blogger, he wrote the definitive history of the blogosphere and published it as a book in 2009. Today, Rosenberg is the tech editor for Axios, a website launched in 2017 by Politico founders Mike Allen and Jim VandeHei.
Since its debut, Axios has tried to upend the paradigm for how news can be delivered. Instead of adhering to the structure of the traditional news article, Axios reporters strive for succinctness by delivering information in a bulleted, just-the-facts-ma’am form. As co-founder Jim VandeHei explained in a 2017 interview, “Ninety percent of stories either shouldn’t have been written or should have been 10 percent the length. Most people do not want to spend five minutes on 1500 words of mediocrity on something that has one interesting fact, figure or quote.”
In my interview with Scott Rosenberg, he told me about Salon’s first viral story and explained why the online magazine was way ahead of its time, in both the way it delivered news and how it monetized content. We also discussed Axios’s approach to news gathering and whether it’s “Be smart” tagline is patronizing or enlightening.
In 2020, Netflix is projected to spend $17 billion on content. Disney will spend $24 billion and AT&T will shell out over $14 billion.
With all that money on the line, there’s an enormous amount of demand for new intellectual property that can be adapted into movies and TV shows, and a lot of that IP is being drawn directly from magazines. The Oscar-winning film Argo, for instance, is based on a 2007 Wired article, and the critically-acclaimed Netflix miniseries Unbelievable is based on a longform Propublica article published in 2015.
This rising demand means that Hollywood is throwing larger and larger sums of money at journalists just to option their articles. All that money has had a distorting effect on the entire magazine industry, with writers increasingly pitching more narrative articles in the hopes of luring a Hollywood agent.
At least that’s according to journalist James Pogue, who recently wrote a piece for the Baffler about what he sees as the negative impact of the streaming wars on magazine journalism. I recently interviewed Pogue about this phenomenon and why he thinks it’s changing longform reporting for the worse.
Of all the algorithms that influence our daily internet browsing habits, few are more closely scrutinized than the one that governs YouTube. Through the homepage, the recommendations that appear on the side of videos, and the trending tab, YouTube’s algorithm has the ability to shower a video with millions of views and transform its unknown users into overnight stars.
It’s because of this very influence that so many people get angry about it. Whether it’s YouTube stars who are worried about their ability to reach their fans or liberal critics who say YouTube promotes right-wing extremism, there are plenty of politicians, journalists, and activists who are up in arms and ready to accuse YouTube executives of all sorts of nefarious evil.
But how many of these accusations are merely conspiracy theories born out of paranoia? To answer that question, I interviewed Chris Stokel-Walker, a journalist who covers YouTube for an online magazine called Fast Forward. Stokel-Walker and I went deep on the YouTube algorithm and the ways its biggest stars game it to their benefit.
I think it’s safe to say at this point that digital publishers recognize the importance of email newsletters. In 2016, Facebook pulled the rug out from underneath a media industry that had, until then, relied on it for hockey stick growth, and over the next several years publishers generally warmed to the idea that the decentralized distribution offered by email newsletters would prove more reliable than the fickle whims of social media giants.
Today, nearly every media company has a robust email marketing strategy, and some news startups interact with their readerships almost entirely within the inbox. We’ve also seen the launch of platforms that make it easier for individual writers to distribute their own newsletters and monetize them through paid subscriptions.
So are newsletters reaching a saturation point? Are they generating real ad revenue? And can newsletters actually replace Facebook as a referral source?
These are just some of the questions I put toward Ernie Smith, the creator and editor of Tedium, a fantastic newsletter that almost operates as a kind of Wikipedia of obscure topics. Smith also runs a popular Facebook group for the newsletter industry, and he’s one of the most knowledgeable people I know when it comes to newsletter trends.
Back in 2010, the world was still skeptical of Wikipedia. High school teachers and college professors warned students to never, ever use it for research. If you ever tried to cite it in an argument, your opponent would mock it as unreliable. Late night hosts like Stephen Colbert would enlist their audiences to flood a specific Wikipedia page and vandalize it. Celebrities and major companies would treat it as a vanity project, editing their own pages while making absolutely no effort to disclose their conflict of interest.
Flash forward to 2020, and Wikipedia certainly has more respect. The Wikimedia Foundation, which acts as its official steward, has tens of millions of dollars in the bank. While college professors don’t view it as a primary source for research, they’ll sometimes endorse it as a starting point for said research. And nearly everyone recognizes it as one of the most influential websites on the internet.
But though tens of millions of people use Wikipedia every day, most only have a passing understanding of how a core group of a few thousand volunteer editors perform the vast majority of contributions to its articles.
One of those editors is Bill Beutler. For the past decade, Bill has consulted with hundreds of brands, helping them to edit their Wikipedia pages without running afoul of the platform’s strict rules. I recently interviewed Bill about the problems that have plagued Wikipedia for the past decade and the issues its community will need to address in the decade to come.
Back in June, the Interactive Advertising Bureau released a report estimating that the podcast industry generated $479 million in 2018 and is projected to make $1 billion by 2021. Not only is this a tiny pittance compared to the money generated by other mediums like TV and search, but podcasting has also been limited by its over-reliance on advertising.
Unlike, say, Netflix or The New York Times, most podcast companies have struggled to diversify their revenue beyond advertising, and most major podcast apps don’t provide a way for podcasters to directly collect money from their listeners.
But several companies, like Spotify and Luminary, are attempting to bundle exclusive podcasts and sell access to them behind a subscription paywall. Other platforms assist individual podcasters in converting their listeners into paying subscribers.
The company Glow fits into the latter category. Founded a little over a year ago, Glow developed technology that allows a podcast’s paying subscribers to listen to paywalled episodes on their podcast player of choice. I recently interviewed its co-founder Amira Valliani about how she’s solving the paywall problem and why she thinks paid podcast subscriptions will eventually scale.
In November, a company called Minute Media announced it was acquiring The Players’ Tribune, the website founded by Derek Jeter that regularly collaborates with pro sports athletes on first-person storytelling.
Though the name Minute Media might not be familiar to most people, chances are you’ve encountered one of the sites it owns, especially if you follow sports. Over the past few years, it’s slowly amassed an amalgam of sports properties that cover everything from global soccer to esports. It also owns Mental Floss, the quirky trivia magazine that was founded in 2001.
I recently sat down with President and CRO Rich Routman to discuss why he thinks Minute Media is different from many of the other venture funded digital media sites out there. We talked about the company’s video strategy, how it approaches advertising, and why it expanded into non-sports content when it acquired Mental Floss.
More than a decade ago, before most people even knew what a podcast was, Macmillan, one of the largest book publishers in the world, launched a podcast network. Called Quick and Dirty Tips, the network consisted of short, scripted podcasts that delivered evergreen, practical advice on a range of topics from grammar to money management.
In the years since, Macmillan has continued to invest in its podcast division, expanding into narrative shows and even teleplays. For this episode, I interviewed Kathy Doyle, vice president of podcasting, about where the company has seen the most success and how podcasting allowed it to diversify its revenue.
Jane Friedman has spent almost the entirety of her professional career working in book publishing. In the mid-aughts, she began writing about the industry, both for professional outlets and her own blog. A few years ago, she launched a paid newsletter that now generates the majority of her income.
I recently interviewed Friedman about her work. We discussed how she grew her newsletter into a sustainable business, and then we talked about the current state of book publishing. One aspect of this world that’s long fascinated me is self-publishing, so I asked Friedman to fill me in on how this market is maturing and where self-published writers are seeing success.
If you listen to the podcast called Startup, then you’ve heard host Alex Blumberg go into exquisite detail about the trials and tribulations of launching a VC-funded podcast network. In earlier seasons, we got a firsthand look about what it was like to pitch venture capitalists, hire talent, and grow the business. In the final season of Startup, Blumberg walked us through Spotify’s $230 million acquisition of Gimlet.
But what about bootstrapped podcast networks that don’t have access to millions of dollars of venture capital money? How do they get off the ground and scale? To answer these questions, I spoke to Jeff Umbro, the founder of the Podglomerate. We talked about his early mistakes in trying to partner with shows for his network and why it can be incredibly difficult to monetize a show with a small audience.
Advance Publications is one of the largest media companies in the world. It owns dozens of newspapers, the Conde Nast magazine empire, and even Reddit.
A few years ago, it launched the Alpha Group, a tech incubator that would launch small startups and try to grow them into thriving, standalone businesses. One of those startups was called The Tylt, a platform that allows its users to participate in online opinion polls on a wide range of issues. The Tylt was successful enough that Alpha Group spun it off as its own company.
Recently, The Tylt hired Selena Roberts, a seasoned journalist who’s written for The New York Times and Sports Illustrated, to serve as its executive editor. I recently sat down with Roberts to learn about the site’s editorial ambitions and whether online, unscientific polls have any journalistic value.
Agnes Kozera knows a thing or two about helping content creators monetize their content. In 2013, she and a co-founder launched Famebit, a platform that helped YouTubers match with brands that were willing to sponsor their videos. The company was so successful that it was eventually acquired by YouTube in 2016.
This year, Kozera and that same co-founder are launching Podcorn, a platform designed to help podcasters monetize their shows. Like Famebit, it will serve as an online marketplace where brands can post RFPs for projects and be matched with participating podcasters. I interviewed Kozera about why such a platform is needed, how the current podcast advertising landscape is flawed, and why podcasters with small-to-mid-sized audiences currently have such a difficult time finding sponsors.
Clive Thompson has the kind of career that most writers would envy. He’s written two books for major publishing houses. He has a monthly column at Wired magazine. And he writes regular features for The New York Times Magazine and other glossy magazines.
But that kind of success didn’t come to him overnight. In fact, Thompson spent years toiling away writing for small publications making very little money. I recently interviewed him to discuss how he made his big break, what it takes to write the perfect magazine pitch, and why book publishers are more likely to award contracts to established journalists.
These days, nearly every major news organization employs multiple reporters who aggressively cover the tech industry, but a decade ago tech coverage was dominated by blogs like TechCrunch, Mashable, and VentureBeat. Back then, these blogs churned out scoop after scoop, competed for traffic, and sometimes even went to war with each other.
Among the earliest of these blogs was ReadWriteWeb. Launched in 2003, it was founded by Richard MacManus, a New Zealander who was inspired to launch a site after reading the work of blog pioneer Dave Winer. Within a few years, MacManus began selling ads and was able to hire a global staff of reporters.
I recently interviewed MacManus about the early days of tech blogging and why, for his latest writing project, he decided to eschew blogging entirely and launch a newsletter instead.
In 2005, a computer software engineer named Gabe Rivera launched the site that would eventually become Techmeme. Governed by algorithms, Techmeme aggregated the day’s tech news, and it eventually became so influential that bloggers and journalists would vie to get their articles featured on the site.
Flash forward to 2018, and Techmeme announced that it would expand its news curation into a daily podcast. I recently sat down with host Brian McCullough to talk about how he came up with the idea for a daily tech podcast and what he’s doing to expand it into an entire podcast network.
The last decade hasn’t been kind to local newspapers. According to one study, 1,800 newspapers have shut down since 2004, and many of those that survived are facing tighter margins, layoffs, and corporate consolidation.
There are myriad reasons for this retrenchment. Part of the blame is on hedge funds that buy up local media companies and then squeeze them dry. Others point to major platforms like Facebook, Google, and Craigslist, all of which have siphoned away a large portion of the local advertising newspapers traditionally relied on.
Despite these headwinds, we’ve seen a few digital-first upstarts thrive in the local news market. One such company is Village Media, which started out as a single news site in an Ontario city and has since grown to 11 sites spread out across Canada.
I recently interviewed Jeff Elgie, Village Media’s CEO, about the company’s history and how it’s succeeded where so many legacy newspapers have struggled or failed.
The Interactive Advertising Bureau recently estimated that podcast industry revenue grew by 53 percent last year and is projected to reach $1 billion by 2021.
With so much year-over-year growth, it shouldn’t be any surprise that many media companies are aggressively expanding their podcast operations. This is certainly true for Vox Media, which over the past few years has launched over 150 podcasts on topics that include technology, politics, and sports. The audio medium is now an eight-figure business for Vox.
I recently sat down with Marty Moe, the head of Vox Media Studios, to talk about how the company is monetizing these podcasts, what he thinks about Spotify’s entry into podcasting, and why he thinks he can grow Vox’s podcast revenue from eight to nine figures.
Back in 2011, LinkedIn announced that it was hiring Dan Roth, who was then the editor of Fortune.com, to serve as its editor in chief. Given LinkedIn’s then role as mostly a repository for online resumes, the move had many scratching their heads.
Over the next few years, though, Roth’s team would roll out a number of editorial products. It started by curating outside news sources, sending LinkedIn users to articles published by business publications like The Wall Street Journal and Business Insider. Then it rolled out a blogging platform that was only available to influential users like Richard Branson and Bill Gates. Eventually, it then opened up its blogging platform to all users.
During all this time, LinkedIn was steadily hiring journalists from some of the world’s top business publications, including The Wall Street Journal, Forbes, and Fortune. Today, it has an editorial staff of 60, and these editors are responsible for everything from curating user content to producing their own original reporting.
I recently sat down with Linkedin senior editor at large Isabelle Roughol. I asked her about how LinkedIn editors go about curating content, how they distribute this content on LinkedIn, and how they approach original reporting projects.
For a few years, Ben Cohen was living the dream. His political opinion site, The Daily Banter, was growing in leaps and bounds, generating enough traffic and ad revenue to support several full-time writers. At its height, the site was getting upwards of 6 million unique visitors a month, fueled in large part by readers sharing his content on Facebook.
But you probably know what happened next. In January 2018, Mark Zuckerberg announced that Facebook was pivoting away from news, and that publishers would see a decline in exposure in the Newsfeed. Virtually overnight, Cohen saw his Facebook traffic drop by 90%.
He tried to hold out as long as he could, but eventually Cohen reached a point where he either had to radically change his business model or shut down the website completely. In the end, he did both. He shut down his website and launched a newsletter. Sign up, and you received two free newsletters a week. Pay a little extra, and you got two additional newsletters.
I recently interviewed Cohen about what went into his decision to pivot and how his readership responded to the announcement.
With social platforms like Facebook throttling distribution for news and the online ad market collapsing, more and more writers are turning to paid newsletters as a way to make a living. In a November 2018 episode of this podcast, I interviewed Hamish McKenzie, the co-founder of Substack, a platform that made it easy for writers to launch newsletters and charge subscribers to receive exclusive issues of those newsletters. At the time, McKenzie said that Substack writers had converted a combined 25,000 readers into paying subscribers.
Flash forward to today, and that number is up to 40,000. In fact, BuzzFeed recently reported that the 12 top writers on Substack make over $160,000 a year each. For this week’s episode, I interviewed one of those writers: Robert Cottrell.
Ten years ago, Cottrell founded a website called The Browser. He would comb through thousands of articles a day and pick the five he found most interesting, adding a dash of commentary to go along with each pick. As time wore on, he began to notice that many of his readers were signing up for an email digest of his daily recommendations.
In 2013, he launched a paid version of the newsletter, and in the intervening years it’s grown to over 10,000 subscribers. I interviewed Cottrell about how he goes about choosing articles every day, what his longterm ambitions are for the newsletter, and why he recently hired a CEO.
It seems like not a week goes by without another online publisher announcing a subscription paywall, but that didn’t make me any less surprised when Business Insider debuted its own paid subscription product.
Founded in 2007 by Henry Blodget, Business Insider took boring, staid business reporting and curated it with a bloggy, conversational voice. Funded by digital advertising, BI tested the theory that a digital media company could scale its way to profitability with free content.
But in 2015, Business Insider was acquired by Axel Springer, a German media company that fiercely protects its intellectual property and is a firm believer that consumers should pay for content. In 2017, Business Insider launched Prime, a subscription product which places some of this site’s daily reporting behind a paywall. Though it still publishes plenty of free content, you’ll have to cough up around $10 a month if you want to access its most deeply-reported articles.
To get insights into Business Insider’s paywall strategy, I interviewed Claudius Senst, its head of consumer subscriptions. I asked him how editors decide whether to place an article behind the paywall, what converts readers into paying subscribers, and why Business Insider didn’t follow in the footsteps of The Washington Post and New York Times by launching a metered paywall.
If you’ve been working in local news over the past decade, chances are that your job hasn’t felt very secure. One study estimated that as many 1,800 local newspapers have shut down since 2004, and those that have survived have faced steep budget cuts and layoffs. Hedge funds have been purchasing newspapers, saddling them with debt, and bleeding them dry, while the Facebook/Google duopoly have diverted more and more local advertising toward their own services. Last year, Facebook launched a feature that would allow users to be shown more local news in their Newsfeed, but it recently admitted that one in three U.S. users lived in areas that didn’t produce enough local news for Facebook to curate.
But not all local news operations have struggled. A New Jersey based media company called TAPinto has launched 81 local news sites and is still growing. While most of those sites are located in New Jersey, the company has recently branched out into Pennsylvania, South Carolina, and Florida. I recently interviewed Mike Shapiro, TAPinto’s founder, and asked him about why his model seems to be working. We also discussed other failed local news projects and whether Facebook’s efforts to boost local news are actually working.
To see my previous interview with Shapiro, go here: https://bit.ly/2Wdvhl4
Back in January, I wrote an article for New York magazine asking whether it’s time for the U.S. government to enact stricter regulation on social media influencers. I pointed to investigations from news outlets like The New York Times that uncovered companies that have sold hundreds of millions of fake followers to willing buyers, most of whom wanted to inflate their online influence.
In many cases, these fake followings were then used to dupe unsuspecting brands into purchasing sponsored Instagram posts. The rising prevalence of fraud within the Instagram influencer community has led to greater scrutiny and efforts to detect such fraud.
To do so, brands now often use software like HypeAuditor, which scans an influencer’s account in search of automated and fraudulent activity. HypeAuditor recently leveraged its data to generate a report on the current state of Instagram influencer fraud. I interviewed Yaro Pat, HypeAuditor’s product owner, about the results of the report and how Instagram fraudsters are getting more sophisticated in how they game the Instagram algorithm.
John Yedinak didn’t have a traditional journalism background when he started his media company. He was working in the mortgage industry when he read an interview with TechCrunch founder Michael Arrington. The interview inspired him to launch his own blog on the reverse mortgage industry, and as the blog’s audience grew, he began to realize that there was a massive market out there for niche, B2B publications.
In 2012, he officially launched the Aging Media Network, a constellation of sites that cover the businesses that service the aging population, from hospice care to senior housing. I recently sat down with Yedinak to talk about how his team built the audience for the publications, how they monetize the sites, and why they focus on advertising instead of paid subscriptions.
Peruse through the vast video archive at The New York Times, and you’ll come across plenty of your standard short documentary films, the kinds with voiceover, b-roll footage, and original interviews. But you’ll also encounter some experimental fare. There’s the fake infomercial advertising a phone hotline for racists. There’s an entire animated series geared toward parents. And then there’s the ongoing series, called Diary of a Song, which uses a mixture of low quality Skype footage and animation to walk the viewer through how a hit song was made.
Overseeing much of this production is Nancy Gauss, executive director of video at The New York Times. I recently interviewed Gauss about her team’s approach to video creation and how it fits in with The Times’s larger goals in driving brand loyalty and paid subscriptions.
Advance Publications is one of the world’s largest media companies. It owns Conde Nast, home to magazines like The New Yorker and Vogue, as well as dozens of newspapers across the U.S. It even has a majority stake in Reddit.
A few years ago, it launched Alpha Group, an incubator meant to launch brand new tech products and grow them into fully functional companies. Rather than acting like a traditional media company, Alpha Group takes a much more expansive view as to what constitutes a 21-century media company, and its products span a wide range of functions, from a social polling app to a Facebook chat bot.
I sat down with David Cohn, a senior director at Alpha Group, to talk about how the company comes up with new product ideas and what it’s like to try to launch multiple tech companies from scratch.
Founded in 1998, MoveOn.org started as a progressive email group and pioneered political online advocacy. Over the past two decades it’s leveraged its massive email list to raise millions of dollars for left-wing candidates and push for a number of progressive legislative issues.
As the internet evolved, so did MoveOn, and today its reach spans millions of followers across the web’s biggest social platforms. In recent years, it’s placed significant emphasis on creating online video, and its videos now generate millions of views each week across Facebook, Instagram, and Twitter.
I recently sat down with Sara Kenigsberg, MoveOn’s senior video producer. I asked about why MoveOn’s videos aren’t designed well for YouTube, how she chooses her video topics, and which social platform is best for broadcasting live video.
It started in 2009 in San Francisco. A couple of journalists got the idea of putting together a magazine, but instead of setting it to print, they would perform it live. Pop-Up Magazine, as the event was called, was a huge hit, and the founders had to seek out larger and larger theaters in order to meet demand.
In 2015, they decided to take the show on the road, touring Pop-Up Magazine across several major cities.
I recently sat down with Chas Edwards, co-founder and president of Pop-Up Magazine. I asked him about the logistics of creating a live magazine from scratch, how the company makes money, and what the future holds for it now that it’s been purchased by the Emerson Collective.
The Atlantic may be a 160-year-old institution, but it isn’t shy about experimenting with new things. It was one of the first traditional publications to go all-in on digital media in the late-aughts and managed to achieve profitability from the move pretty quickly. It experimented with brand new verticals like The Atlantic Wire and Quartz. Recently, it was acquired by Laurene Powell Jobs’s Emerson Collective, which has been investing in forward-thinking media sites.
And since 2012, it’s been running an in-house creative agency called Atlantic 57. The idea is simple: let’s take the editorial insights we’ve gleaned from running a magazine for 160 years and use that to launch online publications for major brands and non-profits.
I recently interview Margaret Myers, a longtime journalist who works on one of these editorial projects for insurance company Allstate. I asked her about her past life as a traditional journalist and how she leverages that expertise in developing content for The Renewal Project, the online publication she manages for Allstate.
When Ben Collins launched his blog about Google Sheets, which is basically Google’s version of Excel, he didn’t intend for it to become a full-time business. He was just documenting his learning process and hoped the blog would serve as an online portfolio for when he went out to seek full-time employment.
But he was surprised to learn that there was an actual audience for his blog posts, and within six months he had thousands of visitors flooding his website searching for how to perform specific actions within Google Sheets.
Eventually, this led to his first paying client, and before he knew it Collins had more incoming business than he knew what to do with. But he wanted to create something a little more scalable, so he started developing an online course for those looking to master the Google Sheets platform.
Within months of launching this course, he was generating thousands of dollars a month in passive income. I interviewed Collins about how he designed his course, how he marketed it, and how he decided on how to price it.
In 2017, The Wall Street Journal published an op-ed titled “How Antitrust Undermines Press Freedom.” It was written by David Chavern, the head of the News Media Alliance, a trade group that represents over 2,000 publishers.
In it, he argues that Facebook and Google have effectively cornered the digital ad market, eating up all its growth, and that this has come at the expense of the very content creators that these two companies rely on, content creators Facebook and Google refuse to fairly compensate.
“The only way publishers can address this inexorable threat is by banding together,” wrote Chavern. “If they open a unified front to negotiate with Google and Facebook—pushing for stronger intellectual-property protections, better support for subscription models and a fair share of revenue and data—they could build a more sustainable future for the news business.”
Earlier this decade, several book publishers banned together to negotiate ebook prices with Apple in a direct effort to undermine Amazon’s command of the market, and they were slapped with a lawsuit from the Department of Justice for violating antitrust laws, hence why the News Media Alliance is seeking a special exemption.
But do publishers deserve one? And even if they do, would they be able to get such legislation passed through such a divided Congress? These are the questions I asked David Chavern for this week’s episode.
Name just about any media beat, and you’ll find plenty of people trying to predict the future. Political pundits argue over who will win the next election. Finance journalists report on economic forecasts and claims from analysts over where a stock will be six months from now. Even entertainment bloggers will try to hash out which film, song, or TV show will win at the next awards ceremony.
But in most cases, those predictions will be wrong. In fact, many studies have shown that a crowd of everyday people will, on average, make better predictions than the experts who work in that particular field. That’s why a lot of attention has been paid lately to betting markets, which can provide real-time odds for any particular outcome ranging from a presidential election to winner of the best picture Oscar.
There’s just one problem: most states outlaw online gambling, meaning many of the most well-known betting markets don’t operate within the U.S. But a relatively new prediction market app, called Futuur, gets around this hurdle by using fictional currency.
I interviewed Tom Bennett, the founder of Futuur, about how his app works and how its predictions matched up against those made by other famous forecasters like FiveThirtyEight.
Subscriptions are all the rage in the media industry right now. Facing diminishing ad rates, publishers have turned to the paid subscription model as a way to draw revenue directly from the users that consume their content. Publishers ranging from The New York Times to The Washington Post to The Financial Times have announced they’ve reached north of a million subscribers. It seems like every day a different publisher is announcing the launch of a metered paywall or membership service.
But getting a news consumer to actually open up their wallet and subscribe is harder than it looks, and the space is only getting more competitive as publishers continue to launch subscription offerings. So what are the actions a publisher can take to make it more likely for a casual reader to convert into a paying subscriber?
A new study from digital publishing platform Twipe sought to answer this question. Researcher Mary-Katharine Phillips surveyed 4,000 news consumers across Europe and the U.S. to gain a better understanding of how they consume the news and what drives their news diet.
I interviewed Phillips about what percentage of news consumers are willing to pay for digital news, what drives them to subscribe, and what kind of news formats they prefer.
You can’t write a history of Web 2.0 without including the contributions of Brian Alvey. After getting his start doing design work for traditional publications like TV Guide and BusinessWeek, Alvey teamed up with his childhood friend Jason Calacanis to launch a series of online publications. Eventually, the two created Weblogs, Inc, a blog network that went on to be sold to AOL. The content management system Alvey built would eventually power AOL’s portal and much of its websites.
But Alvey didn’t stop there; he’d go on to build publishing platforms that would power everything from TMZ to Rupert Murdoch’s ambitious iPad app The Daily.
I interviewed Alvey about what it was like to run a blog network in Web 2.0’s early days, how he ended up in a 45 minute meeting with Jeff Bezos, and why the iPad failed to save the media industry.
In 2014, Ben Thompson, a blogger who writes about the business of technology, announced he was quitting his job so he could write full time. His business model? He would send out four newsletters a week. One of those newsletters would be free, and if you wanted access to the other three, then you had to pay $10 per month.
Within a year, Thompson had 2,000 subscribers, which, if you do the math, means he was generating $200,000 a year. At that point, he stopped publicly disclosing his subscriber numbers, but some predict that he’s increased his subscriber numbers by several thousand.
Thompson was an early pioneer in the realm of paid newsletters, and since then there have been several other writers who struck out on their own with similar models. There’s Nick Quah’s podcast newsletter Hot Pod. There’s political writer Judd Legum’s Popular Information.
Many of these newsletter writers have had to string together multiple services, from Mailchimp to Stripe, in order to manage their businesses. Now we’re seeing a few new companies on the market that want to serve as all-in-one platforms for paid email newsletters.
Once such platform is called Substack, and it recently surpassed 25,000 paying subscribers for its participating newsletter writers. I interviewed the company’s cofounder Hamish McKenzie about the rise of paid newsletters, how to convert readers of a free newsletter into paying subscribers, and why his service is preferable to other membership platforms like Patreon.