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

In 2008, Wade Wallace found himself living in Australia and laid off from the company that moved him there in the first place. With his visa in limbo, and not much else to do, he launched CyclingTips, a blog that covered both the professional and amateur aspects of the sport. What started out as a hobby eventually grew into a fully-staffed news website, one that eventually sold to the investment firm that owned Outside Magazine.

Then in 2022 he quit CyclingTips, raised some investment money, and then launched Escape Collective, which covers the exact same beat. Unlike CyclingTips, Escape Collective is fully funded through paid subscriptions, and when we recorded this interview it was on the verge of profitability.

In a recent interview, Wade walked through his early days building CyclingTips, why he grew unhappy at Outside, and how he grew Escape Collective to 15,000 paying members.

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

There was a time 20 years ago where if you filmed a horror movie on a tight enough budget, you could plausibly turn a profit from the DVD sales alone. Unfortunately for Chris Sharpe, his entry into the horror genre came just as the DVD market was collapsing, and so his career as a movie director fizzled out after he made only one film. 

Luckily, one of the stars of that film, Hilah Johnson, had a strong onscreen presence and a penchant for cooking, and together they launched Hilah Cooking, a YouTube channel that eventually grew to over 450,000 subscribers. Then a few years later Chris teamed up with another co-star from that movie, Adriene Mishler, to launch Yoga With Adriene, which now has over 13 million subscribers on YouTube.

In a recent interview, Chris walked through how he and his collaborators launched both channels, why Hilah decided to eventually end her channel, and the massive success they've seen building a yoga streaming app.

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

If you ask Dave Anderson what he does for a living, he'll probably tell you he's retired, but that's not entirely true. While he did leave his last full-time job at Amazon back in 2020, he still writes a weekly newsletter on Substack about tech leadership. And even though he only works on the newsletter part time, it currently has over 2,000 paid subscribers. It turns out a lot of people want to tap into his insights gleaned from 20 years working in the tech industry, including over 10 at Amazon.

In a recent interview, Dave discussed the newsletter's origin story, how it found its audience, and why he doesn't have any ambitions to scale it into a larger 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.

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

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.

Visit https://memberful.com/simonowens

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.

Visit Memberful: http://memberful.com/simonowens

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.

Visit https://signup.whosponsorsstuff.com/sales-pro/?source=simonowenspodcast

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.

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

Andrew Fogliato never set out to be a marketing consultant. He was simply trying to succeed as a real estate agent and began creating local online content to promote his listings. His colleagues at RE/MAX quickly noticed that his marketing savvy gave him an edge, and soon he was training other agents across Canada. Eventually, he left RE/MAX to launch his own marketing agency, where he built a strong business helping agents run Facebook ads.

In 2022, Andrew saw an even bigger opportunity. He purchased Real Estate Magazine, Canada's largest industry trade publication, and immediately began expanding its online presence. In a recent interview, he discussed why he bought the magazine, his approach to monetization, and why he isn't in a hurry to expand into the U.S. market.

Visit Memberful: https://memberful.com/simonowens

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.

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.

Get a 10% discount on a subscription: https://simonowens.substack.com/a30836c1

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.

Visit Memberful: https://memberful.com/simonowens

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.

Visit Memberful: http://memberful.com/simonowens

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.

Visit SparkLoop: https://sparkloop.app/partner-network?utm_campaign=simonowens

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.

Visit SparkLoop: https://sparkloop.app/?utm_campaign=simonowens

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.

Visit Video Husky: https://bit.ly/vh-simon-owens-pod

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. 

Visit Video Husky: https://bit.ly/vh-simon-owens-pod

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. 

Visit https://theygotacquired.com/newsletter

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

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

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

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

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

SailGP is only a little over five years old, and yet the competitive sailing league has already built out a substantial fan base all across the world. Not only are its competitions broadcast on linear TV channels, it also produces an impressive amount of content that includes YouTube videos, social media clips, and podcasts. In 2022, it hired Melissa Lawton, a longtime sports broadcast producer, to run its content operations, and she's invested heavily in everything from live streaming to highly-produced docuseries.

In a recent interview, Melissa explained how SailGP's media operations fit within its larger business and walked through her team's approach to producing both shortform and longform content.

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.

Sign up at https://cex.events/ and use coupon code "Simon"

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.

Sign up at https://cex.events/ and use coupon code "Simon"

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.

Sign up at https://cex.events/ and use coupon code "Simon"

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.

Get your tickets at https://cex.events/ and use coupon code "Simon"

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.

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.

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

When Eli Woolery and Aarron Walter launched the Design Better podcast, they did it on behalf of InVision, a tech platform used by designers and other creatives. Aaron was the head of content at the company, and the goal of the podcast was to educate the designer community while also raising awareness of the InVision brand.

But when InVision decided to wind down its content operations, Eli and Aarron negotiated to take over Design Better, and now it's a thriving standalone business. In a recent interview, Eli talked through everything from the evolving format of the show to how it became an independent media business to its current monetization models.

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.

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

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.

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

When Kevin Raposo launched KnowTechie in 2014, he had no idea it would grow into a thriving tech news outlet – he just wanted journalists to answer his emails. He was working as a PR consultant and figured reporters would be more receptive to his pitches if they considered him to be one of their peers.

But after three years of running the site, its audience blew up, and Kevin was able to hire several writers to expand its coverage. And while the rise of generative AI has eaten into its traffic, KnowTechie continues to drive meaningful revenue.

In a recent interview, Kevin walked me through his accidental entry into content marketing, his strategy for growing KnowTechie's audience, and how running the site impacts his day job as a tech PR consultant.

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.