The Business of Content

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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 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.  

My newsletter: https://simonowens.substack.com/   For decades, Diane Salvatore helped lead some of America's most recognizable magazine brands, including Consumer Reports, where rigorous product testing and consumer safety were core to the mission. Now, as executive director of the MedShadow Foundation, she's applying that same watchdog mentality to one of the most opaque corners of the marketplace: prescription and over-the-counter drugs.    In a recent interview, Diane walked through how MedShadow operates as a nonprofit investigative newsroom, its expansion into social media video, and its plan to build a donor-supported model that funds independent health journalism.

My newsletter: https://simonowens.substack.com/   For today's episode I spoke to Jim Louderback, the writer behind a newsletter called Inside the Creator Economy   Jim is a longtime media veteran who started out in magazine publishing and then eventually made his way over to the Creator Economy. He spent several years running Vidcon, the annual event where the world's biggest YouTubers connect with their fans, and he now helps organize creator economy events all over the world, including the 1 Billion Followers summit in Dubai.   In our discussion, we covered a wide range of media topics. We discussed whether media companies were overreacting from the threat of Google Zero, why athletes are the new super creators, and how YouTube will slowly devour Hollywood.  

My newsletter: https://simonowens.substack.com/   Kit Chilvers started posting memes on Instagram when he was 14, treating the platform like a video game and obsessing over what made posts take off. A decade later, that experimentation has turned into Pubity Group, a bootstrapped social media company with roughly 170 million followers and hundreds of billions of annual views.    In a recent interview, Kit broke down how he cracked early Instagram growth, why wholesomeness turned out to be a massive business opportunity, and how he's trying to turn platform-native virality into durable media brands, original franchises, and real revenue.  

My newsletter: https://simonowens.substack.com/   In some ways, it's never been a better time to be a standup comedian. In previous eras, aspiring standups had to slowly make their way up through the industry by performing in open mic nights and small venues, but now a few viral video clips on Instagram or TikTok can instantly thrust a new comedian into the spotlight.   But even if a standup has millions of followers on social media, it can be difficult to monetize their fanbase. There's no easy way to alert followers in a certain geographic area that you're performing at a local venue, and social media moderation algorithms consistently throttle reach, especially if a comedian talks about controversial topics.   Danny Frenkel and a co-founder launched Punchup in 2023 to solve these problems. His platform allows comedians to place their video content behind a gate that collects users' email addresses and locations. It also allows venues to sell tickets to events directly through Punchup. Comedians can even directly sell their standup specials on the site. Punchup has already attracted several big name comedians to its network, including  Shane Gillis and Tom Segura,    In a recent interview, Danny walked through the economics of standup comedy, explained how his experience selling ads on Meta informed Punchup's service offerings, and outlined his longterm ambitions for the platform.  

My newsletter: https://simonowens.substack.com/   In today's episode, we're speaking to Suryansh Tibarewala, the co-founder of Essentially Sports.   EssentiallySports began in 2014 as a bootstrapped passion project started by Suryansh and his co-founders while they were college students in India. It started as a simple WordPress site focused on tennis and Formula One. The site ran for four to five years with virtually no revenue, relying largely on volunteer contributors.    But then in 2018, the site's founders decided to quit their day jobs and go all in. They expanded the sports coverage, found reliable advertising partners, and eventually grew EssentiallySports into one of the largest sports sites ranked by Comscore – all without raising outside capital.   In a recent interview, Suryansh walked through the site's early days, its expansion into US sports, and its B2B live events strategy.  

My newsletter: https://simonowens.substack.com/   Roca News was founded on a simple premise: so much of news now is consumed on social platforms, with fewer and fewer internet users clicking through to article pages. After launching in 2020, it gained its initial success on Instagram, where it amassed hundreds of thousands of followers by distilling important news stories into swipeable images. It then launched a daily newsletter that's since grown to over 200,000 subscribers.   Most recently, the company has invested heavily in its YouTube channel, sending its on-camera hosts to far-flung locations to interview everyday people about their unique experiences. Each video racks up hundreds of thousands of views, and the channel has grown to close to 600,000 subscribers in a little over a year.   In a recent interview, co-founders Max Towey and Max Frost recounted Roca's origin story, walked through its initial Instagram strategy, and explained how they invented a unique documentary format for their YouTube channel.  

My newsletter: https://simonowens.substack.com/   When Shane Greer took over the magazine Campaigns & Elections in 2011, it was in a sorry state.    Founded back in 1980, the outlet had once been the gold standard for reporting on the political operatives who help candidates and corporations influence elections.   But by 2011, the magazine was limping along, with its print edition and events struggling to break even. That year, it was acquired by a private equity firm, which installed Greer to run it. In a very short period of time, he killed the print edition, expanded its online reach, and revived its events business.   Then in 2015 he and his business partner Shane D'Aprile acquired Campaigns & Elections, and they immediately set about expanding the company into new niches and regions. Today, there's not only Latin American version of C&E, but the company also bought a B2B media outlet that covers the cannabis industry.   In a recent interview, the two Shanes walked me through their initial strategies for righting the C&E ship, explained why they acquired the magazine, and outlined their plans to build out a B2B media empire.  

My newsletter: https://simonowens.substack.com/   The Kyiv Independent launched in 2021, and its timing was in some ways fortuitous, since it was only a few months later that Russia launched a full-scale invasion in Ukraine. Suddenly, the entire world was paying attention to the country, and the Kyiv Independent happened to be the most authoritative English-language outlet to be reporting on the ground. This attention not only resulted in a massive amount of traffic, but also a surge in membership donations as sympathetic Westerners sought out ways to support Ukraine's cause.   In a recent interview, Chief Operating Officer Zakhar Protsiuk discussed the early days of getting the Kyiv Independent off the ground, its shift from one-time donations to recurring memberships, and why the outlet has begun producing longform documentaries.  

My newsletter: https://simonowens.substack.com/   What if you took Morning Brew's approach to newsletter writing and applied it to local news? That was the original idea behind 6AM City, a company that launched its first newsletter in Greenville, South Carolina in 2016 and gradually expanded into over a dozen cities.   For most of its history, 6AM City's approach was to hire a handful of editors in each city and then gradually build up an audience and advertiser base. But in the last year, it developed a playbook for using AI to launch newsletters in smaller, less populated areas, with the goal of eventually hiring human editors once those newsletters reached certain thresholds.   In a recent interview, co-founder Ryan Heafy explained how these AI newsletters actually work, where they get their information, and what guardrails the company has put in place to ensure quality control.  

My newsletter: https://simonowens.substack.com/   When the media holding company Woven Digital purchased BroBible in 2012, the idea was that the guy-focused publisher would benefit from all the business synergies that come from being part of a larger media network. Instead, BroBible was neglected and undermonetized. So when Woven began unraveling its holdings in 2018, BroBible's staff banded together and bought it back. And what started out as a staff of seven has grown to 16 today, and the business is diversified across programmatic advertising, events, and sponsored social media posts.   In a recent interview, publisher Brandon Wenerd walked through Brobible's early blogging days, its transformation into a real business, and how breaking free of its parent company allowed it to adapt to the current media climate.  

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/   When Tomiwa Aladekomo took over Big Cabal Media eight years ago, the company was little more than two promising publications that were read mostly within Nigeria. He stepped in not as a founder, but as someone who had spent years inside every corner of the media world, including music, advertising, brand strategy, and digital publishing. And he saw, even then, that Big Cabal had the potential to diversify its revenue and scale up into one of the most influential media companies in Africa.  In a recent interview, Tomiwa walked through how that early instinct turned into a 100-person company that now stretches across multiple countries and several lines of business. He also discussed how Big Cabal is navigating the same headwinds facing publishers everywhere—including shrinking social traffic and the rise of AI—while also confronting challenges unique to African media.