Explore every episode of the podcast The Business of Content with Simon Owens

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When Ramin Beheshti co-founded The News Movement in 2021, he wanted to build a news organization that could reach younger audiences without relying on traffic to a traditional website. Instead of trying to lure readers away from platforms like TikTok and Instagram, the company would produce journalism specifically designed for those platforms and figure out how to monetize the resulting audience. Five years later, that experiment has evolved into Caliber, a media holding company with more than 60 employees and a growing portfolio of brands that includes The Recount, Capsule, and a new news aggregation app called SaySo. Along the way, Beheshti has had to rethink everything from how his journalists produce videos to how the company's business model.

In a recent interview, Beheshti explained why Caliber abandoned its initial reliance on traditional sponsorships in favor of building a branded content agency, how it learned to turn shortform social audiences into viewers of longer YouTube videos, and why he believes the future of his company lies in helping independent creators build sustainable media businesses without giving up their independence.

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When the NBA teamed up with video game publisher Take-Two Interactive to launch an esports league in 2017, the idea was to replicate the traditional sports model within the world of competitive gaming. NBA teams would field their own esports franchises, recruiting elite gamers to compete in organized tournaments. But as the esports industry matured, it became clear that the biggest audiences weren't necessarily tuning in to watch professional gaming competitions. Instead, they were gravitating toward individual creators on platforms like Twitch and YouTube. Recognizing this shift, the NBA and Take-Two decided to rethink their joint venture, transforming it from a traditional esports league into a broader media company that produces creator-led competitions, original video series, and social content centered on basketball culture.

To lead this transformation, they hired Andrew Perlmutter, a media executive who previously worked at The Atlantic and The Daily Beast. Since becoming CEO of NBA Take-Two Media in 2023, Perlmutter has overseen the reinvention of the NBA 2K League while developing a slate of original programming designed to reach audiences well beyond hardcore basketball fans. 

In a recent interview, we discussed why the traditional esports business model struggled to gain traction, how the company is building a network of creator-led shows and social media franchises, and how it plans to turn that programming into a sustainable business through sponsorships, licensing, and other revenue streams.

Amy Suto spent years climbing the Hollywood ladder, eventually landing a writing credit on the TV series Condor. But by the time she achieved that milestone, she was already questioning whether she wanted to spend the rest of her career writing other people's stories. Meanwhile, she had built a lucrative side business ghostwriting memoirs for everyone from professional athletes to wealthy entrepreneurs. She eventually left Hollywood behind and began building a career that now spans multiple businesses, including a ghostwriting consultancy, a paid Substack newsletter, a freelance job board, and several self-published novels. She's also cultivated a large audience on TikTok, where she shares advice on how to make a living as a professional writer.

In a recent interview, Amy explained how she manages to juggle so many creative projects while still finding time to pursue new business opportunities, how she built a Substack with more than 1,000 paid subscribers by putting curated freelance job opportunities behind a paywall, and how she's using serialized fiction to generate recurring revenue while building an audience for her novels.

Despite producing critically acclaimed shows like Severance, Slow Horses, and The Morning Show, Apple TV remains one of the smallest players in the streaming industry. It also reportedly loses billions of dollars a year, which raises an interesting question: Does Apple actually care whether its streaming service turns a profit? Or is the company perfectly happy to subsidize expensive Hollywood productions if they help sell more iPhones and drive subscriptions to its broader services ecosystem? And if Apple does want to become a serious competitor to Netflix and Amazon, what would it need to change about its business strategy?

To help answer these questions, I invited back Jason Krebs, a media industry veteran who's held senior roles at The New York Times, Google, and Disney. We discussed why Apple has been so reluctant to embrace advertising, whether its limited content library is holding back subscriber growth, and how its investments in live sports might fit into its long-term ambitions.

We also talked about the growing number of traditional media companies launching newsletters on Substack. Once viewed primarily as a platform for independent journalists looking to escape legacy media, Substack is increasingly attracting established publishers like The Economist, The New Yorker, and The Ringer. What's driving this shift? Are these companies simply experimenting with a new distribution channel, or do they see Substack as a way to reach paying subscribers who would never visit their websites? And could these standalone newsletters eventually cannibalize their existing subscription businesses?

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After spending more than two decades touring with some of the biggest names in music — including the Jonas Brothers, John Legend, Eminem, and Selena Gomez — Benji Woerly decided it was time to build something of his own. He turned to an idea his father had dreamed up back in 1994: a fictional world populated by magical creatures called the Soovins. What began as a small passion project has evolved into an animated children's YouTube channel with more than 138,000 subscribers and several videos that have generated hundreds of thousands of views. And Woerly has much bigger ambitions. He wants to turn The Soovins into a global entertainment franchise that spans streaming platforms, music, merchandise, and live events.

In a recent interview, Woerly discussed how he assembled a production team with virtually no animation experience, why he's treating YouTube primarily as an audience-building platform rather than a major revenue source, and how he plans to leverage that audience into lucrative distribution and licensing deals.

For years, Facebook has steadily reduced the organic reach of businesses and publishers, forcing them to pay for advertising if they want to reach the audiences they've spent years building. Now Meta is taking things a step further by imposing what amounts to a link tax: Businesses that want to post more than two external links per month to their Facebook pages will have to pay at least $49.99 a month. News publishers are supposedly exempt from the new policy, but given Meta's history of broken promises, there's little reason for them to feel secure. At this point, is there any reason for a media company to maintain a Facebook presence at all?

To discuss this, I sat down with Jason Krebs, a media industry veteran who's held senior roles at Google, The New York Times, and Disney. Jason has spent decades navigating the complicated relationship between media companies and the technology platforms they depend on for distribution. We discussed why publishers continue investing resources into Facebook despite its dwindling organic reach, whether the platform still offers any meaningful value, and why media companies should be wary of building audiences they don't directly control.

We also turned our attention to Paramount Skydance's acquisition of Warner Bros. Discovery and the enormous challenges that lie ahead. David Ellison plans to combine Paramount+ and HBO Max into a single streaming service, but integrating millions of subscribers while managing $81 billion in debt could prove far more complicated than executives anticipate. We discussed whether the merger will deliver any meaningful benefits to consumers, why Ellison decided to keep Mark Thompson in charge of CNN, and whether the combined company has an opportunity to build a streaming platform that blends Hollywood productions with creator-generated content.

Condé Nast was once synonymous with the excesses of the magazine industry's golden age: chauffeured cars, lavish photo shoots, enormous expense accounts, and glossy titles that commanded both cultural influence and premium advertising dollars. That world is long gone, but Condé Nast itself has endured. With CEO Roger Lynch now leaving the company, it's a good moment to ask what remains of that old empire. Has Condé Nast successfully reinvented itself around subscriptions, events, and premium advertising, or has it simply become a smaller, less culturally relevant version of what it once was?

To talk through that question, I brought back Jason Krebs, a media veteran who has held senior roles at The New York Times, Google, and Disney. Jason also spent time at Condé Nast, giving him a firsthand view of how the company operated during an earlier era. We discussed how the publisher survived the collapse of the print advertising model, why its decision to avoid the programmatic advertising race mattered, and whether the next generation of leaders can keep brands like Vogue, The New Yorker, and Vanity Fair relevant.

We also dug into another question facing legacy media companies: Should the traditional wall between editorial and business still be quite so high? As creators build lucrative businesses around sponsorships, merchandise, and other direct monetization, many traditional publishers and TV networks still leave their biggest digital audiences largely in the hands of platform revenue shares. Jason and I discussed why editorial and commercial teams should be talking to each other more often, how those collaborations can happen without compromising journalistic independence, and what the media industry can learn from creators who have become much better at monetizing the trust and attention they've built.

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Startup CPG didn't begin as a media company. It started with Daniel Scharff inviting a few people from the consumer packaged goods industry to meet up at a bar in San Francisco. But those informal gatherings eventually grew into something much larger: a 40,000-member Slack community, dozens of in-person events, a podcast, webinars, newsletters, social channels, and an awards program for emerging brands. Along the way, Scharff realized he had effectively backed into building a media company — one whose audience consists of the founders, investors, retailers, and service providers powering the next generation of food, beverage, beauty, and wellness brands.

In a recent interview, Scharff explained how the pandemic helped transform a local events company into a national community, why Startup CPG keeps most of its products free while generating the bulk of its revenue from sponsorships, and how its events are increasingly designed to connect emerging brands directly with the retailers and investors who can accelerate their growth.

Sports betting has become one of the most important new revenue streams in sports media, but the relationship is quickly moving beyond simple advertising. News organizations and broadcasters are increasingly incorporating betting odds and prediction-market data directly into their coverage, blurring the line between journalism and gambling promotion. At the same time, legalized betting may be helping drive more attention toward live sports, giving fans a financial incentive to watch games they otherwise wouldn't care about — just as streamers like Amazon, Netflix and YouTube are bidding aggressively for sports rights and team valuations continue to climb.

To unpack all of this, I brought back Jason Krebs, a media veteran who has worked at Google, The New York Times and Disney. We discussed whether media companies can justify embedding prediction markets into their journalism, how sports betting has become intertwined with the economics of live sports, and whether the massive influx of streaming money is creating a bubble in sports rights and franchise valuations. 

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When Adam Ryan launched Workweek in 2021, the thesis was that some of the most valuable voices in B2B weren't professional journalists or full-time creators, but practitioners who had spent years accumulating expertise inside their industries. Rather than asking those people to quit their jobs and become media entrepreneurs, Workweek would give them the infrastructure to turn that expertise into newsletters and other content — then help them grow and monetize their audiences. Over the past several years, however, that model has evolved considerably. What started as a tightly curated group of creators is increasingly becoming something much closer to a network and publishing platform built specifically for business professionals.

I recently spoke to Ryan about how the company arrived at that model and where it goes from here. We discussed why Workweek believes B2B newsletters are better monetized through advertising than subscriptions, how its homegrown professional communities are designed to replace some of the functions once served by trade associations, and why the company is now letting far more practitioners launch their own newsletters instead of handpicking a small roster of creators.

The New York Times has become one of the few legacy media companies to successfully reinvent itself for the digital era, but that doesn't mean it's immune to disruption. One of its emerging problems is that some of the journalists it helps turn into stars can eventually make far more money by leaving and building independent businesses. The latest example is the team behind Hard Fork, whose hosts reportedly attracted multimillion-dollar offers to strike out on their own. So does the Times need to rethink how it compensates its biggest personalities? And as more journalists build audiences that can travel with them, how much power does the institution still hold over the talent?

To talk through those questions, I brought back Jason Krebs, a media veteran who has held senior roles at Disney, The New York Times, and Google. We discussed why legacy publishers still tend to treat journalists like salaried employees rather than talent — and whether they need to start offering revenue sharing, bigger incentives, or other compensation structures to keep their biggest stars from walking out the door.

We also explored why national newspaper chains like McClatchy continue to struggle with local news, whether private equity hollowed out those businesses without investing enough in new models, and why locally focused publishers may be better positioned to survive. Then we debated the escalating cost of sports rights, why Amazon can justify spending so aggressively, and whether traditional media companies have allowed leagues like the NFL to gain too much leverage over their businesses.

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Design Anthology was founded in 2014 around a simple idea: some of the most interesting design work in Asia-Pacific wasn't getting the attention it deserved. The magazine set out to give those designers a global platform, wrapping its journalism in a premium print product designed to be kept rather than discarded. Over time, it has grown into a broader media business spanning print, digital subscriptions, events, branded partnerships, and a YouTube channel with more than half a million subscribers.

Jeremy Smart joined Design Anthology in 2018 as an art director and gradually moved into editorial leadership, becoming its sole editor in chief last year. In a recent interview, we discussed why the company still sees premium print as central to its identity, how it has built an advertising business around long-term relationships rather than audience scale, and how its fast-growing YouTube presence serves as a gateway into the rest of the brand.

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In 2015, Reid Hailey started an anonymous Instagram meme page called Shithead Steve, mostly as a way to joke around with his friends. But once he began creating original memes, the account took off, eventually reaching a million followers and generating meaningful advertising revenue. Hailey soon teamed up with Derek Lucas, who was running his own fast-growing social accounts, and the two began building a portfolio of meme and user-generated-content pages across different niches. That collection of accounts eventually evolved into Doing Things, a social-first entertainment company behind shows and brands like Recess Therapy, Bob Does Sports, and Breezy Golf.

I recently spoke with Hailey, now the CEO of Doing Things, about how the company uses audience data to test and refine new shows, how it structures deals to keep creators invested in long-term success, and how it decides which properties have the potential to expand beyond content into products and other businesses.

The Wall Street Journal found itself at the center of an AI controversy after publishing an op-ed that billionaire investor Stanley Druckenmiller later acknowledged he had written with the help of AI. What made the episode especially notable wasn't the disclosure itself, but the Journal's reaction: Its opinion editor essentially shrugged, arguing that AI is now a fact of modern life and that what matters is whether the piece accurately reflects the author's views. So is this a watershed moment for mainstream newsrooms? And as AI becomes a routine part of the writing process, does it even make sense to require disclosures every time it lends a hand?

To talk through those questions, I brought back Jason Krebs, a media veteran who has held senior roles at Disney, The New York Times, and Google. We discussed whether using AI to write an op-ed is really all that different from the decades-old practice of executives relying on ghostwriters.

We also explored why fashion and lifestyle influencers have flocked to tennis — and why the U.S. Open in particular has become such a major cultural event for brands and creators. Then we unpacked the Good Good Golf controversy and what it reveals about the growing risks brands take when they move beyond simple creator sponsorships and build entire products and businesses around internet personalities.

There was a time when HuffPost and BuzzFeed looked like the future of digital media. Both mastered the mechanics of internet distribution, attracted enormous audiences, and convinced investors that scale itself could become a durable competitive advantage. So how did two of the defining brands of the digital-media era end up shrinking so dramatically? Was the underlying business model always flawed, or did a series of strategic mistakes — from costly acquisitions to overreliance on platforms like Facebook — turn these promising companies into cautionary tales?

To help answer these questions, I brought on Jason Krebs, a longtime media executive who has worked at some of the industry's biggest companies, including Google, Disney, The New York Times, and Condé Nast. He's spent decades watching media business models rise and fall, which makes him an especially useful person to talk to about an industry that keeps cycling through new theories about distribution and scale.

We also discussed two very different approaches to building subscription businesses. Jason weighed in on The New York Times' experiment with an AI chatbot trained on its own archives and whether the reputational risks are worth it. And we dug into MS NOW's new subscription product, debating whether personality-driven hosts like Rachel Maddow and Chris Hayes can convert their audiences into paying members.

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Jomboy Media began as a Yankees podcast launched by Jimmy O'Brien and Jake Storiale with a small investment from a friend. Since then, it has evolved into a much larger sports media company, with dozens of channels, a roster of full-time creators, its own in-house sales operation, and even an original sports league called Warehouse Games. Much of that growth accelerated after Courtney Hirsch joined the company in late 2020, first to build out its advertising business and eventually to become CEO.

In a recent interview, Hirsch explained why the company now builds around creators rather than individual shows, how Warehouse Games could evolve into a major entertainment franchise built on IP Jomboy owns outright, and why she believes apparel could become one of the company's biggest businesses.

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Over the past year, book publishers have repeatedly found themselves caught in controversies over authors' use of AI. Social media sleuths run books through AI-detection tools, accusations start flying, and in some cases publishers cancel a book's publication altogether. But how much should readers actually care if an author uses AI for research, editing, or polishing prose? And are publishers genuinely concerned about the technology, or are they simply trying to avoid the backlash that comes with it?

To talk through those questions, I spoke with media veteran Jason Krebs, whose career has spanned some of the industry's biggest companies and smallest startups. He's worked across media, advertising, and content at companies including Google, Disney, The New York Times, and Condé Nast. 

We also spent a large portion of the conversation digging into YouTube's evolving strategy. The platform is making it harder for smaller creators to qualify for ad revenue, setting an especially high bar for Shorts monetization, and increasingly positioning itself as a competitor to traditional television and streaming services. Jason and I debated what these moves say about YouTube's advertising ambitions, why Shorts may function more as a hedge against TikTok than a standalone creator business, and what happens as YouTube and Netflix increasingly encroach on each other's turf.

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For years, micropayments have been one of those ideas that repeatedly resurface in the publishing industry without ever seeming to gain much traction. The theory is simple: instead of forcing every reader into a recurring subscription, let them pay a few dollars for a single article or a short period of access. But previous experiments have often struggled with payment friction, weak economics, and fears that cheaper options would cannibalize subscriptions. 

The Washington Post has spent the past two years trying to solve those problems, running more than 30 tests to determine which products, prices, and audiences make flexible access work.

The person leading this experimentation is Anjali Iyer, the Post's global head of subscription marketing. In a recent interview, she discussed why the Post believes technology has finally made micropayments viable, how it discovered that anonymous visitors are the ideal audience for flexible access, and why offering a cheaper short-term option can actually improve both subscription conversion and retention. 

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Nate Stone was still in high school when he built a YouTube channel with hundreds of thousands of subscribers by filming science and engineering experiments in his garage. But unlike many creators who stumble into a large audience, Stone never had much interest in turning that audience into a full-fledged media business. He eventually walked away from YouTube, studied physics, math, and computer science, worked on AI at Amazon, and then teamed up with his brother to build DittoDub, an AI-powered dubbing platform designed to help YouTubers reach audiences in dozens of languages.

In a recent interview, Stone explained how his frustrations as a teenage YouTuber helped inspire DittoDub, why the company focused on winning over large creators through product quality and word of mouth, and how multilingual audio can trigger enormous audience growth on YouTube.

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When Ellen Hyslop and her co-founders launched The Gist in 2017, none of them had worked in media or the sports industry. They were young professionals in financial services who had grown frustrated with a sports media ecosystem that largely catered to men while overlooking millions of potential female fans. What began as a side project built during evenings and Sundays has since grown into a sports media brand with more than 1 million newsletter subscribers, hundreds of thousands of social followers, a podcast, paid community, proprietary games, and partnerships with major advertisers.

In a recent interview, Hyslop explained how scrappy marketing helped attract The Gist's first subscribers, why social media became an important source of revenue, and how the company is expanding into a paid community and launching its own games. 

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Founded in a Detroit garage in the early 2010s, Benzinga started as a scrappy finance blog for everyday stock market enthusiasts. Over the next decade, it grew into a major digital media platform, carving out a niche by sending detailed stock analysis directly to retail investors and major brokerage apps like Robinhood and Fidelity. Following a majority acquisition by private equity firm Beringer Capital in 2021, the company entered a new era of growth, hiring former Bloomberg editor Brad Olesen as its first Chief Content Officer to bring its news, video, and data teams together under one roof.

In a recent interview, Olesen broke down what it takes to run a modern, multi-channel financial news operation, why Benzinga treats social media as a brand-building tool instead of a website traffic driver,  and how the company balances free, ad-supported news with premium subscription products.

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For most of her career, Ashanti Bentil-Dhue didn't have a social media presence. But after spending a decade running a consulting business, she moved from the UK to New York and decided to start sharing her ideas publicly for the first time. Armed with little more than an iPhone, she began posting unscripted TikTok videos about the experiences of single women. Within months, she had built an audience of hundreds of thousands of followers and expanded into a media business that now includes a Substack publication, YouTube channel, and consulting.

In a recent interview, Bentil-Dhue explained how she built a large audience despite having no prior social media experience, why she believes consistency matters more than high-end production, and how she's turning her growing platform into a sustainable business.

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For years, the audiobook industry was defined by a single dominant player and a purchasing model that asked listeners to commit to an entire book before they knew whether they would enjoy it. Spotify is betting that there's a better way. By folding audiobooks into its subscription service and using the same discovery engine that powers its music and podcast recommendations, the company is trying to transform audiobooks from a niche product for avid readers into a mainstream entertainment format. Duncan Bruce, Spotify's director of audiobooks partnerships and licensing, has been at the center of that effort, working with publishers to build the company's licensing strategy and expand its catalog from 150,000 titles at launch to more than 700,000 today.

In this interview, Bruce explained how Spotify convinced publishers to embrace a radically different distribution model, why casual sampling is unlocking new audiences for authors, and how the company is using AI and product innovation to make audiobooks more accessible without replacing human creativity.

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The war in Ukraine has given rise to an entirely new generation of independent media organizations, but few have a backstory as unusual as The Counteroffensive. Founded by veteran journalist Tim Mak after more than a decade covering politics, national security, and investigations for outlets including NPR, Politico, and The Daily Beast, the publication began as a one-man Substack chronicling life inside wartime Ukraine. In just a few years, it has evolved into a growing media company with multiple publications, a team of reporters across Europe, and an expanding portfolio that spans consumer journalism, defense intelligence, and postwar reconstruction.

In our interview, Mak explained how an unexpected career pivot led him to launch a newsroom from Kyiv, why he believes text-based journalism—not podcasts or video—remains the strongest engine for paid subscriptions, and how he's building a diversified media business designed to outlast the war itself.

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For more than a decade, Erin Millar has been trying to answer a question that has plagued the journalism industry: What should replace the local newspaper model after it collapses? Her first attempt came with The Discourse, a Canadian media company that experimented with new approaches to community-driven reporting before eventually evolving into a network of local news outlets. But along the way, Millar realized that the biggest opportunity wasn't necessarily building another media chain — it was creating the infrastructure that could help hundreds of independent publishers thrive.

That insight led to the launch of Indiegraf, a software and services company that now supports 180 local communities across North America and beyond. In a recent interview, Millar explained why she believes the future of local news will be built around networks rather than traditional chains, how Indiegraf helps publishers generate revenue, and why consolidation may actually strengthen independent media.

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When Mike Rogge purchased Mountain Gazette in early 2020, he wasn't acquiring a thriving media business. For $5,000 and the cost of a couple beers, he bought a dormant outdoor magazine brand whose main assets consisted of a URL, a trademark, decades of archives, and boxes of old issues sitting in storage. But Rogge believed the magazine's legacy — which included contributions from writers like Hunter S. Thompson and Edward Abbey — still carried meaning. At a time when many publishers were chasing algorithms and scale, he wanted to prove there was still a market for a beautifully designed print publication built around passionate readers rather than fleeting clicks.

Five years later, Mountain Gazette has grown into a profitable independent magazine with tens of thousands of subscribers who pay for two oversized print issues a year. In our interview, Rogge explained why he rejected the traditional ad-driven media model, how a subscriber-first approach allowed him to invest more into writers and photographers, and why he believes print's resurgence is tied to a broader backlash against an increasingly digital world.

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For years, HubSpot was known as a pioneer of content marketing, building a huge library of articles that helped attract potential customers to its software products. But more recently, the company has expanded far beyond blog posts. It now owns newsletters, podcasts, YouTube channels, and creator-led media brands that reach millions of people every month.

Jonathan Hunt, HubSpot's VP of media, has helped oversee this evolution after working at companies like Vice, Vox Media, National Geographic, and Complex. In our interview, he explained why HubSpot is investing so heavily in media, how it turns content audiences into software customers, and why it sees creators as a major part of its growth strategy.

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When Aaron Wilbur launched The Coaches Site in 2010, he simply wanted to solve a problem he kept seeing in hockey: the best coaches were constantly sharing ideas with each other, but that knowledge rarely made its way to coaches at lower levels of the sport. What started as a small coaching conference eventually turned into a subscription platform with more than 41,000 coaches across 54 countries and over $1.5 million in annual recurring revenue.

In my interview with Wilbur, we discussed how he turned conference videos into a subscription product, why evergreen content works so well for coaching education, and how he's building a platform that allows coaches across all sports to share and monetize their expertise.

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When Will Richards first started compiling news about startups, he wasn't trying to launch a media company. He was working at a family office and needed a better way to track what was happening across the Australian startup ecosystem. After realizing there wasn't a single place that aggregated all this information, he began sending out a weekly email. That side project eventually evolved into Overnight Success, a newsletter read by thousands of founders, investors, and startup operators.

But Richards didn't stop at building a newsletter. He's since expanded Overnight Success into a broader business that includes sponsorships, a startup database, and an investment syndicate. In our interview, we discussed how he grew within such a narrow niche, why a small audience can still attract major sponsors, and how he's turning years of startup coverage into a valuable data product.

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When Sipho Kings and his co-founder Simon Allison launched The Continent in 2020, they wanted to rethink how journalism is distributed online. Instead of chasing search traffic and social algorithms, they created a weekly PDF newspaper designed specifically for smartphones and distributed it through platforms like WhatsApp, Signal, Telegram, and email. The idea was to bring back the simplicity of a curated newspaper while adapting it to how people actually consume information today. Six years later, The Continent reaches tens of thousands of readers across Africa and around the world.

In a recent interview, Kings explained how the publication grew entirely through word of mouth, why its unusual PDF format created a deeper relationship with readers, and how it's building a sustainable media business outside the traditional web ecosystem.

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For years, Hollywood writer Aaron Tracy built his career inside the traditional television system, writing for shows like Law & Order and navigating the endless cycle of pilots, canceled series, and development purgatory that defines much of the TV business. But over the last several years, Tracy has quietly carved out a very different kind of entertainment career: producing serialized audio dramas for platforms like Audible and iHeart. Along the way, he's worked with everyone from Aaron Paul to Lizzy Caplan to Glenn Powell, helping pioneer a form of storytelling that sits somewhere between television, audiobooks, and podcasting.

In a recent interview, Tracy explained why audio dramas offer writers far more creative freedom than television, how he packages and sells narrative shows to platforms like Audible and iHeart, and the surprisingly lean production process behind large-scale audio series.

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After spending several years helping launch food and travel magazines in London, Krista Faist returned to Toronto with a simple idea: replicate the free magazine model that was thriving across the UK transit system. In 2015, she launched Twenty Two Media Group and started building two media outlets into lifestyle brands focused on food, travel, and culture. What began as a one-person operation has since grown into a media company spanning print, digital, events, and now shortform video.

In a recent interview, Faist explained how she landed major advertisers before the first print issue even launched, why she still believes premium print magazines have real value in a digital-first media landscape, and how Twenty Two Media Group is expanding into vertical video and creator partnerships while keeping print at the center of the business.

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James Capo has spent much of the last decade helping publishers solve one of the industry's biggest challenges: how to better understand and monetize their audiences. As CEO of Omeda, he oversees a platform that powers subscription management, email marketing, audience data, and paywall tools for many of the world's largest media companies.

In a recent interview, Capo explained why he believes many publishers have made audience management far more complicated than it needs to be, how AI could soon help publishers better predict churn and improve subscriptions, and why media companies should build more niche products and verticals around loyal audiences.

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Straight Arrow News was founded around a simple idea: a lot of Americans feel like they're living in completely different realities depending on where they get their news. The company grew out of conversations between founder Joe Ricketts and media executive Jonathan Harding, who come from different political viewpoints but realized they were often consuming very different versions of the same stories. Their goal was to build a digital news outlet focused on politically unbiased reporting and a clearer separation between news and opinion. Over the past year, that mission has increasingly been shaped by chief content officer Derek Mead, the former Vice editor who helped oversee that company's international expansion and also ran its US newsroom.

In a recent interview, Mead explained why the company is moving away from high-volume aggregation and investing more heavily in original journalism, how it's using video and social distribution to reach audiences fatigued by partisan news, and why he believes there's still room for a new national media brand built around trust instead of outrage.

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There's a certain irony that one of the most influential publications covering Australia's telecommunications industry still arrives each morning as a daily PDF. But that format has become central to the success of Communications Day, the niche B2B outlet founded by Grahame Lynch in 1994. What began as a fax-delivered newsletter covering the early deregulation of Australia's telecom market evolved into an indispensable industry briefing read by executives, regulators, infrastructure providers, and tech companies across Australia and New Zealand. While much of digital media spent the last two decades chasing pageviews, social traffic, and algorithmic distribution, Lynch built a highly profitable subscription business by doing almost the opposite: keeping his journalism off the open web, tightly controlling distribution, and turning Communications Day into a daily habit for nearly everyone working in the sector.

In a recent interview, Lynch explained why Communications Day still distributes its journalism as a PDF despite the rise of blogs and social media, how he built a subscription business with near-total market penetration in a niche B2B sector, and why conferences now account for nearly half the company's revenue.

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The TV advertising business has changed dramatically over the past two decades. What used to be a relationship-driven industry built around upfront presentations and manual negotiations has turned into a fast-moving, highly automated digital marketplace. As ad dollars have shifted to streaming, the system has become more complex, introducing new challenges like hidden fees and widespread ad fraud.

Matt Wasserlauf, the founder of Blockboard and a longtime veteran of both traditional TV and digital video, has had a front-row seat to that evolution. In a recent interview, he explained why ad fraud has ballooned into a nine-figure problem for the industry, how blockchain-based verification aims to ensure ads are actually reaching real humans, and why he believes as much as 90% of ad spend is lost to fraud and intermediary fees combined.

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Before launching his own media company, Andrew Palermo spent years working in marketing, where he saw firsthand how affiliate deals between brands and publishers actually worked. That experience sparked the realization that many of the sites earning commissions weren't producing especially helpful or original content. In 2018, he decided to test whether he could do it better, launching Prudent Reviews as a side project. He started with products he already owned, with a focus on detailed, hands-on reviews. Flash forward eight years, and Prudent Reviews is not only one of the most authoritative home appliance review websites, but it also reaches a half million subscribers across YouTube, Tiktok, and Instagram.

In a recent interview, Andrew explained how his background in affiliate marketing shaped his approach to building Prudent Reviews, why Google's shifting algorithms and the rise of AI forced him to rethink his entire traffic strategy, and how video ultimately became the foundation of a more durable media brand, one that's mostly protected from AI chatbots.

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Digital advertising has long been shaped by a David-versus-Goliath dynamic, with publishers struggling to compete against tech platforms that control better data, more powerful ad tools, and vastly larger pools of advertiser demand. That raises a few big questions: Why have publishers struggled to close that gap despite the promise of programmatic advertising? What advantages do platforms like Google and Meta have that the open web still lacks? And as AI takes on a larger role in ad buying, could it help level the playing field — or further entrench the dominance of the largest platforms?

Rick Erwin, CEO of Adstra and a longtime ad tech executive, has spent decades working at the center of these shifts. In a recent interview, he explained why tech platforms have built such a durable advantage over publishers, how advertisers decide who sees their ads, and why he believes AI could fundamentally change how ad campaigns are planned and executed.

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Jessica Dante didn't set out to build a multi-platform travel media company—she set out to escape one. After an early career managing social media for corporate travel brands, she quickly grew frustrated with the slow-moving, top-down decision-making that defined the industry. So she struck out on her own, initially experimenting with blogging before discovering a more powerful insight: travelers weren't reading—they were watching. That realization led her to launch a YouTube channel focused on hyper-specific, highly practical London travel advice, a niche that was both underserved and endlessly in demand. Over the next several years, that channel evolved into Dante Media, a business spanning YouTube, Instagram, TikTok, email newsletters, and a suite of high-margin digital travel products.

In a recent interview, Jessica explained how she identified a scalable content niche that didn't require constant travel, why a "drive-by" audience can be more valuable than loyal fans in certain contexts, and how the rise of AI-generated travel planning is beginning to erode one of her most important revenue streams, forcing her to rethink what parts of her business can still command a premium.

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For most brands, TV advertising has long operated as an opaque, high-stakes gamble—an expensive channel dominated by middlemen, limited measurement, and a reliance on blunt audience estimates. That's the system Philip Inghelbrecht set out to disrupt when he co-founded Tatari. Tatari is attempting to rebuild the TV ad stack from the ground up—bringing automation, outcome-based measurement, and software-driven media buying to a medium that has historically lagged far behind digital.

In a recent interview, Philip explained how Tatari is turning TV into a performance channel that more closely resembles digital advertising, why the company has rejected the programmatic-heavy approach in favor of direct publisher integrations, and how falling cost barriers are opening the door for a new class of advertisers to enter the TV market.

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The rise of "sleep podcasts" has quietly reshaped a corner of the audio industry, turning bedtime into a high-engagement listening moment. Few creators have benefited more from that shift than Kathryn Nicolai, whose Nothing Much Happens podcast has grown from a scrappy 2018 experiment into what she describes as the largest sleep podcast in the world. Drawing on decades of experience as a yoga and meditation teacher, Katyrhn built a format that flips traditional storytelling on its head—stories designed not to captivate listeners through to the end, but to gently lull them to sleep. Along the way, she's expanded the concept into books, subscriptions, and a growing ecosystem of products built around relaxation and habit formation.

In a recent interview, Kathryn explained how she accidentally helped define an entirely new podcast genre, why word-of-mouth drove her early growth, and how she's built a monetization strategy around an audience that's literally falling asleep.

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Axios Local began as an experiment in translating a national media brand's playbook into the fragmented world of city-level journalism. After acquiring the Charlotte Agenda, Axios used it as a template to launch a network of local newsletters built around a simple idea: hire well-connected reporters, deliver concise, high-signal updates directly to readers' inboxes, and monetize through a mix of local and national advertising. The model leaned heavily on email as a distribution channel and "smart brevity" as a product philosophy, allowing Axios to build strong brand awareness in early markets while sidestepping many of the traffic and platform challenges that have plagued traditional local news.

In a recent interview, executive editor Holly Moore explains how Axios is using AI to shrink newsroom staffing requirements in smaller markets, why the company is experimenting with regional coverage models that stretch a single reporter across multiple geographies, and how its long-term ambition could see it expand into hundreds of cities. 

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Robbie Daymond is best known as a prolific voice actor, the kind of performer whose work spans anime, video games, and animation without ever putting his face front and center. After slowly breaking into the industry in the late 2000s and early 2010s, he built a rare, multi-disciplinary voiceover career—one that includes everything from audiobooks to major gaming franchises. He also spends up to 30 weekends a year attending fan conventions where he engages directly with audiences in what has quietly become one of the most lucrative and meaningful parts of his business.

That creator-first ethos has increasingly shaped his ambitions beyond acting. In recent years, Daymond co-founded Sassy Chap Games, an independent studio that turned a quirky concept into one of the fastest-selling dating sims ever, fueled largely by viral user-generated content rather than traditional marketing. The project offers a window into how modern creative careers are evolving by blending IP ownership with direct-to-consumer distribution models.

In a recent interview, Robbie explained how fan conventions have quietly become a major revenue engine for creators, why you don't always need a huge social media presence to build a large audience, and how revenue-sharing models can unlock top-tier creative talent.

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For most of his career, Scott Brown has operated at the crossroads of Hollywood and the creator economy. After first breaking into digital media during the early days of web series, Scott went on to work across a wide swath of the modern media ecosystem. His résumé includes producing hundreds of hours of Larry King programming for streaming platforms, helping Dwayne Johnson launch a YouTube channel that quickly surpassed a million subscribers, and even producing large-scale stunts for MrBeast. Throughout that journey, Scott developed a front-row seat to how digital platforms were steadily reshaping the economics and creative possibilities of entertainment.

Today Scott believes the next major shift is already underway: the rise of microdramas—short, vertically shot scripted series designed for smartphones and often monetized episode-by-episode inside dedicated apps. 

In our conversation, Scott explained how he stumbled upon the emerging format, why he believes it represents the first truly native form of scripted storytelling for phones, and how his own microdrama projects are helping push the medium toward higher production quality. 

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Pat Walls didn't originally set out to build a media company. In 2017, he was simply interviewing founders as a side project while working a full-time job, hoping the conversations might spark his next startup idea. But those interviews—published as detailed case studies on a blog called Starter Story—slowly evolved into something much bigger. Over the next eight years, Pat bootstrapped the site into a media business built around thousands of founder stories, growing its audience through a series of distribution pivots that ranged from Reddit to SEO to YouTube. That journey culminated recently in a major milestone: the sale of Starter Story to HubSpot Media for what Pat describes as a "life-changing" amount.

In a recent interview, Pat explained how Starter Story transformed from a scrappy side project into a profitable media brand, why video ultimately became the company's biggest growth engine, and his decision to shift away from advertising toward higher-priced products and boot camps.

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Founded during the pandemic, the The News Movement set out with a simple but radical premise: what if journalism were designed entirely for the platforms where younger audiences already consume information? Rather than trying to pull readers back to a website, the company built a newsroom that publishes directly to TikTok, Instagram, and YouTube Shorts, translating the conventions of traditional reporting into vertical video, carousels, and other native formats. 

In a recent interview, editor-in-chief Rebecca Hutson explained how the outlet approaches platform-first journalism, why its reporters function as "triple-threat" video journalists who can shoot, edit, and publish their own stories, and how the company tailors coverage differently for each social platform.

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In 2004, Eric Hochberger co-founded Mediavine, which would eventually become one of the most influential ad management companies on the open web. The company didn't start as an ad tech firm — it began as a scrappy collection of SEO-fueled fan sites, built by three founders chasing traffic in the early blogosphere. While selling $50 sidebar ads and offering SEO consulting services, Eric and his partners learned firsthand how fragile and inconsistent early digital advertising could be. That experience ultimately pushed Mediavine to build its own header bidding system in 2014, a move that quadrupled the company's ad revenue and transformed it from a publisher into an ad management platform.

Today, Mediavine represents roughly 17,000 publishers and operates with a 140-person team, primarily serving independent creators rather than legacy media brands. In a recent interview, Eric pulled back the curtain on how programmatic advertising actually works, why "made-for-advertising" sites are siphoning off industry dollars, and how Google's AI Overviews are reshaping traffic patterns — sometimes wiping out entire businesses overnight.

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Michael Fritzell doesn't fit the typical profile of a newsletter writer. Before launching Asian Century Stocks, he spent 15 years inside the machinery of global finance — working in investment banking and eventually managing money for a wealthy family in Singapore. A Swedish native who studied Chinese at Peking University, Michael built a career analyzing overlooked equities across China and Southeast Asia. When he struck out on his own to launch the Asian Century Stocks newsletter in 2021, he wasn't experimenting with a side hustle — he was walking away from a traditional finance track to build a niche media business focused on Asian stocks that most Western investors ignore

Launched on Substack and now operating independently, Asian Century Stocks sells in-depth, 40- to 60-page research reports to paying subscribers, many of whom are professional investors accustomed to paying banks tens of thousands of dollars a year for comparable research. Michael positioned himself as a bridge between local Asian markets and global capital — offering deeply reported, independent analysis without the conflicts that often accompany sell-side research.

In an interview, he explained how he went from anonymous finance professional to six-figure recurring revenue newsletter operator, why he ultimately left Substack for Ghost, and what it takes to monetize serious financial research in a tightly regulated industry.

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

Michael Fritzell doesn't fit the typical profile of a newsletter writer. Before launching Asian Century Stocks, he spent 15 years inside the machinery of global finance — working in investment banking, buy-side firms, and eventually managing money for a wealthy family in Singapore. A Swedish native who studied Chinese at Peking University, Michael built a career analyzing overlooked equities across China and Southeast Asia. When he struck out on his own to launch the Asian Century Stocks newsletter in 2021, he wasn't experimenting with a side hustle — he was walking away from a traditional finance track to build a niche media business focused on Asian stocks that most Western investors ignore

Launched on Substack and now operating independently, Asian Century Stocks sells in-depth, 40- to 60-page research reports to paying subscribers, many of whom are professional investors accustomed to paying banks tens of thousands of dollars a year for comparable research. Michael positioned himself as a bridge between local Asian markets and global capital — offering deeply reported, independent analysis without the conflicts that often accompany sell-side research. 

In an interview, he explained how he went from anonymous finance professional to six-figure recurring revenue newsletter operator, why he ultimately left Substack for Ghost, and what it takes to monetize serious financial research in a tightly regulated industry.

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

In 2011, as the golden era of glossy newsweeklies was fading, former Time correspondent Nathan Thornburgh made a bet that serious journalism didn't have to look the way it always had. Alongside food writer Matt Goulding, he launched Roads & Kingdoms as a scrappy Tumblr experiment, using food as a gateway into geopolitics, history, and culture

Over the next decade, Roads & Kingdoms evolved from a bootstrapped digital publication into a creative hub for Anthony Bourdain—who invested in the company and used it as a base for ambitious editorial and branded projects. After Bourdain's death in 2018, the outlet was forced to reinvent itself. Nathan and Matt shrank the operation and rebuilt it around high-end culinary travel experiences. Now, they're relaunching the media arm with a membership-driven model and an annual print magazine

In a recent interview, Nathan reflected on the collapse of legacy media, the perils and possibilities of brand-funded journalism, and why he believes independent, reader-supported publishing offers a more durable path forward.