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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.