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, di...
May 19, 2026•47 min
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 ...
May 14, 2026•1 hr 2 min
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 ...
May 12, 2026•1 hr 3 min
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 exe...
May 07, 2026•55 min
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 lo...
May 05, 2026•35 min
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 ...
Apr 30, 2026•58 min
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...
Apr 28, 2026•57 min
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...
Apr 21, 2026•58 min
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 histor...
Apr 16, 2026•45 min
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 flip...
Apr 14, 2026•41 min
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 heav...
Apr 07, 2026•49 min
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...
Mar 31, 2026•55 min
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 ...
Mar 12, 2026•1 hr 3 min
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 found...
Mar 10, 2026•53 min
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 n...
Mar 05, 2026•46 min
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...
Mar 03, 2026•51 min
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 t...
Feb 26, 2026•42 min
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 hi...
Feb 25, 2026•42 min
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 creat...
Feb 18, 2026•1 hr 5 min
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 ...
Feb 16, 2026•1 hr 4 min
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 Billi...
Feb 13, 2026•1 hr
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 b...
Feb 09, 2026•49 min
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...
Jan 28, 2026•1 hr
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'...
Jan 27, 2026•55 min
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 c...
Jan 21, 2026•1 hr 6 min
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 ...
Jan 19, 2026•59 min
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...
Dec 17, 2025•42 min
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 develo...
Dec 12, 2025•56 min
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 busine...
Dec 08, 2025•1 hr 1 min
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 qui...
Dec 05, 2025•56 min
