How the NBA's esports league reinvented itself as a media company

Instagram is making another push into longform video, hoping to convince YouTubers and podcasters to upload their content to its platform. There's just one problem: Unlike YouTube, Instagram has no established revenue-sharing program that would compensate these creators for the advertising revenue their videos generate. Instead, Meta seems to be betting that the promise of exposure will be enough to attract creators who are already monetizing their content elsewhere. But will that strategy actually work, or will Meta eventually be forced to share more of its revenue with the people who make its platforms valuable? To discuss this, I invited back Jason Krebs, a media industry veteran who's held senior positions at companies like The New York Times, Google, and Disney. We discussed why Meta has been so reluctant to embrace revenue sharing, whether that strategy has contributed to its negative public reputation, and what it would take for the company to finally change course. We also turned our attention to Netflix, which has experienced some executive upheaval as it struggles to keep subscribers engaged with its content. With YouTube capturing an increasingly large share of television viewing, Netflix has been experimenting with new formats like video podcasts in an effort to compete. But is the company doing enough to adapt to a world where consumers have access to virtually unlimited free entertainment? Jason and I debated whether Netflix should introduce a completely free, advertising-supported tier, whether it should open its platform to user-generated content, and what its future might look like as it evolves from a high-growth technology company into a more traditional media business.  

My newsletter: https://simonowens.substack.com/ When Nicole Hunn launched the blog Gluten Free on a Shoestring in 2009, she wasn't a professional chef or an experienced media entrepreneur. She was a recently laid-off lawyer who had spent years experimenting with gluten-free recipes after her son was diagnosed with celiac disease. Frustrated by the high prices and poor quality of gluten-free products, she saw an opportunity to build a business around helping families like hers. Nearly two decades later, she's built a thriving recipe website supported by programmatic advertising, amassed an email list of 130,000 subscribers, and published six cookbooks. But like many independent publishers, she's also had to contend with unpredictable platform algorithms, declining referral traffic, and the challenges of diversifying beyond advertising revenue. In a recent interview, Hunn explained why traditional cookbook publishing never generated the kind of revenue she'd hoped for, how Google's changing search ecosystem has forced her to rethink her business strategy, and why she's now betting on direct-to-consumer products to build a more sustainable future.  

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

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

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

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