How a few local meetups spawned an entire B2B media company

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.  

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.   

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

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

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.