My newsletter: https://thelongstory.substack.com/ When JJ Hornblass got his first journalism job in the 1990s, his dad made a deal with him: he could spend a few years as a reporter, but he had to eventually make his way over to the revenue side of the media business. It only took JJ a few years to follow through on that deal. While working as an e…

My newsletter: https://thelongstory.substack.com/ The Dispatch was launched in 2020 with a pretty straightforward thesis: that people would pay for quality, fact-based journalism. It certainly had a partisan lean – it was co-founded by conservative journalists Jonah Goldberg and Steve Hayes after all – but it steered clear of the wholesale rejectio…

My newsleter: https://thelongstory.substack.com/ When the Manchester Mill launched in 2020, it operated on a simple theory: that local audiences would pay for news as long as it was original and differentiated. It quickly proved that model out and was able to hire its first full-time employee within a matter of months. From there, founder Joshi Her…

My newsletter: https://simonowens.substack.com/ When Matthew Schniper launched his Colorado Springs food newsletter in 2023, he ran into a problem many local news entrepreneurs face: he didn’t have enough time to do his reporting and chase down advertisers. Luckily, by that point he already had strong relationships in the Colorado Springs food scen…

My newsletter: https://simonowens.substack.com/ What’s the true monetary value of a newsletter subscriber? Tim Huelskamp knows the answer to that question. As the co-founder of the 1440 newsletter, he knows how many emails the average subscriber will open, how much money they’ll generate in ad revenue, and what it costs to acquire them. It’s this r…

My newsletter: https://simonowens.substack.com/ 2024 was a big year for the podcast industry. Not only were there several huge deals signed, but podcasts wielded significant influence in the US presidential election. These days it’s impossible to open YouTube, TikTok, or Instagram without coming across podcast clips, and the market is still poised …

My newsletter: https://simonowens.substack.com/ David Stein had an innovative marketing hack for growing his investing podcast called Money for the Rest of Us. He put the names of other popular finance podcasts in his metadata, and Apple’s unsophisticated search algorithm would surface his show whenever people were searching for his competitors. By…

My newsletter: https://simonowens.substack.com/ In 2017, Ben Cohen was living the dream. His politics news site The Daily Banter was generating over 6 million visits a month and enough advertising revenue to support him and a small stable of writers. But then the floor fell out from under him virtually overnight; Facebook pivoted away from news and…

My newsletter: https://simonowens.substack.com/ Like a lot of journalists=turned-media–entrepreneurs, Eric Newcomer decided to launch a paid newsletter after leaving his job at Bloomberg in 2020. That model yielded 2,500 subscribers who collectively pay over $400,000 a year to access his newsletter about startups, but that’s no longer the biggest p…

My newsletter: https://simonowens.substack.com/ The last few years have been pretty good to the Kansas City Chiefs, what with its multiple Super Bowl championships and a close association with the biggest pop star in the world, but BJ Kissel remembers what it was like to be a fan of the team long before it started regularly winning games. Back in t…

My newsletter: https://simonowens.substack.com/ Lon Seidman doesn’t operate the largest gadget YouTube channel in the world, but he doesn’t need to in order to run a successful media business. That’s because he remains hyper focused on reviewing non-sexy products that sell in extremely high volumes. This has allowed him to build a highly lucrative …

My newsletter: https://simonowens.substack.com/ Book publicity is a mixed bag these days. On the one hand, it’s never been easier for an author to form a direct relationship with their audience with tools like Substack and TikTok. On the other hand, more books are published each year than ever before, which means competition is fierce. Most newspap…

My newsletter: https://simonowens.substack.com/ When people sign up for the Alts.co newsletter, they’re looking to read its deep dives into alternative investments like art, baseball cards, and rare books. But the most serious investors in its audience want access to actual deal flow, and to gain that access they sign up for Altea, a high-priced me…

My newsletter: https://simonowens.substack.com/ Eric Siu has a pretty massive audience; his YouTube channel boasts 161,000 subscribers and his two podcasts – Marketing School and Leveling Up – have generated tens of millions of downloads. But Eric doesn’t bother with traditional media monetization models like advertising or subscriptions. Instead, …

My newsletter: https://simonowens.substack.com/ When Keith Pepper bought a chain of print newspapers back in 2020, he received an email from a columnist at the Atlanta Journal Constitution that basically asked if he was crazy. But Keith had a plan for taking a company that generated 98% of its revenue from print advertising and converting it into a…

My newsletter: https://simonowens.substack.com/ Layoffs in the local news sector are, sadly, a regular occurrence, but the founders of Block Club Chicago decided they weren’t going down without a fight. In November 2017, the news startup DNA Info laid off its entire staff, and it was only a few months later that three of its editors launched a Kick…

My newsletter: https://simonowens.substack.com/ For much of its 130-year existence, State House News operated as a standard newswire service. Its journalists covered the Massachusetts state government and it then syndicated their content to regional and national newspapers. But in the late 90s, owner Craig Sandler realized that internet distributio…

My newsletter: https://simonowens.substack.com/ Most people are familiar with newswires like the Associated Press and Reuters, but a much newer upstart called Stacker has devised a new business model for syndicating content. Rather than charging a fee for its articles, it instead gives away its data journalism to any publisher that wants it. It the…

My Substack: https://simonowens.substack.com/ Mignon Fogarty isn’t just one of the world’s most popular podcasters, she’s also an incredibly innovative media entrepreneur. She launched her Grammar Girl podcast 18 years ago, and the success of that propelled her book onto the New York Times bestseller list. She also founded Quick & Dirty Tips, a med…

My newsletter: https://simonowens.substack.com/ Most companies buy advertising to drive sales of their products, but Andrew Curtin’s first sponsor mostly bought out of pity. It was May 2022 and he had just launched Construction Wave, a B2B outlet that covers the UK’s construction industry. He had absolutely no audience, but a major crane manufactur…

My newsletter: https://simonowens.substack.com/ Like a lot of journalists in the mid-2000s, Tim Burrowes grew frustrated with his employer’s print mentality and its tendency to treat online publishing as an afterthought. At the time, he worked for an Australian trade magazine that covered that country’s media industry. So in 2008, he and two co-fou…

My newsletter: https://simonowens.substack.com/ When Alex Halperin launched WeedWeek in 2015, he was entering an industry that had nothing but growth ahead of it. But what he didn’t expect was that the fragmented legalization across states meant that it’d be difficult to build a national audience. So a few years ago he pivoted to just covering Cali…

My newsletter: https://simonowens.substack.com/ One of the great things about being a college journalism major today is that it’s incredibly easy for professors to build their own news sites and allow students to experience every aspect of the publishing process. Not that long ago, journalism students had few avenues for publication outside their c…

My newsletter: https://simonowens.substack.com/ When Patrick O’Shaughnessy launched his podcast Invest Like the Best in 2016, he had no intention of building it into a media company. He just wanted to use it to interview the world’s best investing minds so that he could deepen his own understanding of the industry. But the show proved to be a huge …

My newsletter: https://simonowens.substack.com/ What does a professional travel photographer do when all international flights are shut down due to a global pandemic? That’s a question Gary Arndt found himself asking in the early months of 2020. By that point, he had built up millions of social media followers and an entire career from snapping pho…