The Business of Content

My newsletter: https://simonowens.substack.com/   The podcast company Sonoro launched in 2020 with a relatively simple thesis: that there were very few media companies geared toward the 62 million latinos within the US. Over the next four years, it built out a stable of dozens of podcasts across several formats ranging from serialized nonfiction to personality-led chat shows. In addition to the standard podcast monetization models, it also sought to further capitalize its IP by selling adaptations to Hollywood studios and developing its own merch lines. Today, the network generates over 100 million monthly downloads and works with some of the world's biggest latino creators.   In a recent interview co-founder Joshua Weinstein explained how the company partners with talent and walked through all the ways it's monetizing its IP.  

My newsletter: https://simonowens.substack.com/   When the media covers business acquisitions, it's usually only for huge deals involving VC-backed companies. Coverage of mergers for small, bootstrapped businesses is almost nonexistent. That's where They Got Acquired comes in. Launched in 2021, it focuses on acquisitions in the $100,000 to $50 million range. Recently, it put out a detailed research report specifically focused on acquisitions of media outlets, which are typically sold at lower multiples than other kinds of online businesses.   In an interview, founder Alexis Grant walked through the experience she had selling two of her own media outlets and explained the steps a current media entrepreneur should take to maximize the selling price for their own business.  

My newsletter: https://simonowens.substack.com/ Given the tumultuous economic landscape for local news, many outlets are turning to nonprofit models because they offer increased flexibility for generating revenue. But while these outlets have been adept at attracting foundation grants and small donor memberships, they're not doing enough to cultivate relationships with the wealthy members of their own communities, many of whom can write much larger checks than your average reader.   At least that's the thesis of Julie Rafferty. She not only has a deep background in consulting with nonprofits, but she also played an instrumental role in co-founding Brookline News, a nonprofit media outlet that operates outside of Boston.    In a recent interview, Rafferty walked through how she got wealthy members of her city to fork over $100,000 before the outlet even launched, and she gave some good advice on how other nonprofit newsrooms can identify and reach out to rich people in their own communities.  

My newsletter: https://simonowens.substack.com/   If you work in the media industry, you're likely aware of The New York Times tremendous success with its gaming vertical; in fact, millions of people subscribe solely so they can play games like Wordle and Connections.   But it's not the only publisher that's incorporated games into its business strategy. Hundreds of outlets ranging from Morning Brew to The New Yorker utilize a platform called Amuse Labs to build everything from crosswords to sudoku. In a recent interview, co-founder John Temple explained how publishers can leverage games to increase everything including time on site, repeat visits, advertising revenue, and paid subscription conversions.  

My newsletter: https://simonowens.substack.com/   You've probably never heard of Schneps Media, but if you live in any of the five boroughs of New York, you've probably encountered its content. Started as a single Queens newspaper in 1985, the company gradually bought up community news outlets all across New York, and it's since expanded into Philadelphia and even Palm Beach, Florida. It not only targets audiences by locale, but also ethnicity. And most of its news is completely free to read.   How has the company continued to grow despite so many headwinds in local news? To answer this question, I spoke to CEO Josh Schneps. He told the story of how his mother launched that first Queens newspaper and explained why businesses continue to advertise with him despite having plenty of other options.  

My newsletter: https://thelongstory.substack.com/   Earlier this year, China crossed a major milestone when BYD, an electric car company based in its Shaanxi province, surpassed Tesla in total sales. What's more, most experts believe the country is only at the beginning of its EV dominance. In a recent Washington Post article titled “How China pulled ahead to become the world leader in electric vehicles,” journalist Christian Shepherd explained how the country's centralized, top-down government prioritized every level of the supply chain, from the building materials to the manufacturing to the charging stations.    In a recent interview, we discussed what decisions the country made over a decade ago to incentivize EV production, to the point where it can sell cars at nearly half the price of its non-Chinese competitors. We also explored what the US would have to do if it wants to catch up.  

My newsletter: https://thelongstory.substack.com/   They walk among us, almost completely undetected. If you notice them at all, it's because they're pulling a discreet tin out of their pockets so they can replace the small, white pouch hidden above or beneath their molars.   Yes, I'm talking about Zyn enthusiasts. Though the nicotine pouch came to our shores over a decade ago, it's only within the last few years that its reach expanded from the boiler rooms on Wall Street to the open office cubicles in Silicon Valley.   How did the product develop its obsessed fanbase? To answer that question, I turned to Carrie Battan, the author of a New Yorker piece titled “Zyn and the New Nicotine Gold Rush.” In our interview, she traced its origin as a Swedish cigarette replacement, explained why it has the potential to radically expand the nicotine-delivery industry in the US, and assessed the science as to whether nicotine is even bad for us when it's not absorbed through the lungs.  

My newsletter: https://thelongstory.substack.com/   Heading into 2025, we knew that MrBeast had a huge online following. After all, his main channel has grown to over 300 million subscribers and 74 billion views. He's built out an entire studio in North Carolina and is mobbed by legions of fans wherever he goes.   But what we didn't know was whether this online fame would translate into traditional Hollywood success. MrBeast famously signed a $100 million deal with Amazon to create one of the most ambitious game shows of all time, and it debuted in December with 1,000 contestants and $5 million in grand prize money.   Flash forward to today, and it's clear that the show was an unequivocal success, with Amazon claiming it reached record viewership numbers. Now, Hollywood studios are casting about for other projects that can be helmed by popular creators.   What will those projects look like? To answer that question, I spoke to Lucia Moses, the co-author of a Business Insider piece titled “What MrBeast can teach Hollywood.” We discussed why previous creator-led shows failed, how the Beast Games viewership compared to other popular shows, and whether MrBeast's production mishaps that led to a class action lawsuit will give studio executives any pause.  

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 editor at American Banker, he pitched his bosses on launching a print newsletter covering the mortgage securities market. When those bosses took too long to make a decision, he left his job to launch the newsletter on his own. Flash forward 30 years, and that newsletter has grown into Royal Media, a B2B media company that covers four niche industries.   In a recent interview, JJ explained where he found his initial subscribers for that first newsletter, how he expanded into new verticals, and why he's so focused now on building and selling access to data platforms.  

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 rejection of reality that's rampant in most pro-Trump media.   Flash forward to 2025, and that thesis has been vindicated. It recently crossed 45,000 paid subscribers without the help of huge VC investors. Now, it plans to diversify its revenue streams, and to accomplish that it brought on Mike Rothman, a longtime media veteran who helped build companies like Thrillist and Fatherly.   In a recent interview, Mike walked through his decision to join The Dispatch, what kind of advertising he wants to sell, and why brands are suddenly interested again in sponsoring politics media.  

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 Herrmann decided to replicate this model across other cities in the UK, and Mill Media now runs six publications that have collectively generated tens of thousands of paid subscribers. In a recent interview, Joshi discussed why he first got interested in local news, how he decided to expand to different cities, and whether he thinks his model can be replicated by other local news startups.  

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 scene, and so he approached 12 of his favorite restaurants with an interesting proposition: if they came on as annual sponsors, he would go above and beyond to feature them in his newsletter, and he wouldn't allow any other local businesses to advertise. This allowed him to focus on his reporting and not waste time on sales calls. The experiment was so successful that over half of the restaurants have already renewed for a second year.   In a recent interview, Matthew explained how he came up with the idea, what services he provides for these 12 restaurants, and why he thinks his model can be replicated by other local news startups.  

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 ruthless approach to unit economics that allowed 1440 to grow to over 4 million subscribers, all without raising any VC investment. In a recent interview, Huelskamp walked me through the original idea behind the company, how he and his co-founders generated their first few thousand subscribers, and why 1440 is now expanding beyond the inbox into topic-based explainer content.  

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 for significant growth in the coming years.   But if you run a small-to-mid-sized podcast, it's still incredibly difficult to make a living from your work. You need to join an advertising network to generate significant revenue, and most networks won't accept you unless you meet a minimum audience threshold.   To deal with these challenges, many podcasters turn to Scott Porch. Scott runs Big IP, a podcast management company that helps podcasters grow their audiences and monetize their content. In a recent interview, he explained how he chooses which podcasters to work with, what value he brings to the relationship, and why he's bullish on paid subscriptions for podcasts.  

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 the time Apple eventually eliminated that functionality, Money for the Rest of Us had built up a loyal audience that's since downloaded the show over 20 million times. His audience is so loyal, in fact, that it sustains a high-priced membership community that charges $450 a year and generates well into the six figures in revenue.   In a recent interview, David walked me through how he developed his investing expertise, what he offers to paying members, and why he launched his own premium investing app.  

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 sent his traffic plummeting. Without traffic, his advertising revenue crumbled.   So in an act of desperation, Ben pivoted his entire business model into paid subscriptions. Doing so forced him to slow down his publishing schedule and focus on serving his core audience. Slowly but surely, he built up a new revenue base, and in the last few months he passed the threshold of 1,000 paid subscribers.   In a recent interview, Ben explained how he executed on his pivot and why he's determined to never rely on a single large tech platform ever again.  

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 part of his business.   Today, Eric generates over $1.5 million a year from the Cerebral Valley AI Summit, a twice-a-year conference that he monetizes through a mixture of ticket sales and premium sponsorships. In a recent interview, he explained the conference's origin story, how he attracts the right mix of startup founders and VC investors, and why he thinks he can replicate its format across multiple tech industry niches.  

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 the early 2010s, he began blogging for SB Nation, and he used his success there to eventually land a job as the Kansas City Chiefs in-house reporter. In that role, he did everything from writing web articles to serving as a sidelines correspondent for live game broadcasts.   In 2021, he struck off on his own and co-founded the KC Sports Network, a group of podcasts and YouTube channels that cover Kansas City Sports. Today, puts out 10 different shows and is monetized through a mixture of local and national advertisers.   In a recent interview, BJ explained why he left his job at the Chiefs, how he convinced local businesses to sponsor his shows, where he sees new opportunities for growth.  

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 affiliate business, not only on YouTube, but also on Amazon Video.   In a recent interview, Lon explained his methodology for picking products to review, how he optimizes his affiliate links, and why he's spending more time posting his content to decentralized platforms.  

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 newspapers have laid off most of their book critics, but at the same time there's an ever expanding ecosystem of podcasts that are eager to have on book authors for longform interviews.   Probably nobody is more knowledgeable about marketing books in the modern age than Kathleen Schmidt. She spent nearly 20 years working for almost every major book publishing company, and she now runs her own firm that specializes in book marketing. She also writes Publishing Confidential, her insider account of how the book industry actually functions.   In a recent interview, Kathleen walked through nearly every aspect of selling books, from choosing the right cover to courting influencers to advertising on Amazon.  

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 membership community that actually vets potential deals and allows them to invest. Not only does Alts.co generate revenue through the annual membership, but it also charges for management fees and carried interest. In essence, Alts.co is a media company that monetizes via an investment firm.   In a recent interview, co-founder Stefan von Imhof explained why his company settled on this model, how it sources deals, and why he eventually wants to stop selling sponsorships within the newsletter.  

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, he leverages his influence to drive clients to Single Grain, a marketing agency he owns. As that business grew, he was able to acquire more agencies and add to Single Grain's capabilities, and it now works with some of the world's largest brands.   In a recent interview, Eric explained how he met his co-host, where he found his audience, and why he chose to monetize his content with a services business.  

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 digital-first media company.   And he's done just that. Today, Rough Draft Atlanta generates 27% of its revenue from digital ads, and it managed this feat without seeing a significant decline in print advertising. This has allowed Keith to reinvest in the business by hiring more journalists, and it's now stronger than ever.   In a recent interview, Ketih explained how he consolidated all the newspapers under a single brand, his strategy for attracting online ads, and why he's avoided placing his content behind a paywall.  

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 Kickstarter that raised over $183,000;  they used that capital to launch Block Club Chicago, a nonprofit that seeks to put a journalist in each of the city's neighborhoods.   Flash forward six years, and Block Club has a robust news gathering operation that's funded by 20,000 paying subscribers, foundation support, and a growing advertising business. In a recent interview, co-founder Stephanie Lulay walked me through the site's launch strategy, its unique approach to neighborhood-based reporting, and why she thinks Block Club's model can be replicated all across the US.  

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 distribution would allow him to sell direct digital subscriptions and vastly expand his customer base. Today, the service charges $4,000 a year to any company or organization whose business is directly influenced by the state's government.   In a recent interview, Craig discussed how he built the direct subscription business, why he decided to sell a majority stake in the company, and whether State House News is shielded from the whims of large tech platforms and AI chatbots.  

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 then charges brands a fee to create and distribute sponsored content across the thousands of media outlets that subscribe to its service.   In a recent interview, co-founder Noah Greenberg explained how Stacker works with publishers, its process for creating sponsored content, and why he has no interest in driving an audience to Stacker's owned and operated website.  

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 media network she now runs in partnership with Macmillan Publishers.   To round out her media business even more, she's launched around seven courses, all geared toward being a better communicator and writer. Thousands of customers have taken them, and they've opened her up to an entirely new customer base for her content.   In a recent interview, Mignon explained how she entered the courses market, what goes into putting together a course, and why she decided to partner with powerful distributors like LinkedIn Learning rather than create the courses by herself.  

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 manufacturing company bought a $10,000 sponsorship anyway.   That $10,000 allowed him to hire his first editor, and over the next two years they built Construction Wave up into one of the leading publications in its sector. Its website is mainly monetized through high-priced sponsorships, and this year it hosted its first conference geared toward construction CFOs.   In an interview, Andrew explained how he got interested in the sector, where he found his initial readers, and why he thinks there's an opportunity to launch a subscription data product for his industry.  

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-founders decided to launch Mumbrella, a competing blog that published upwards of 15 times a day. Its gossipy comments section quickly attracted an audience of bored office workers, and within a few years it was hosting multiple industry events that collectively generated millions of dollars.   In a recent interview, Tim explained how Mumbrella made such a big splash so quickly, why he and his co-founders decided to sell it, and what he's doing differently with his newest media startup.   

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 California's weed industry, and WeedWeek has since built a robust business monetized through both sponsorships and subscriptions.   In our interview, Alex walked me through what got him interested in the topic, why he built a customer publishing platform, and how he recently decided to team up with the LA Times on an investigative series.  

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 college newspaper.   Lydia Chavez took advantage of this dynamic while teaching at UC Berkeley. In 2008, she and her colleagues launched Mission Local, a local news blog that covered San Francisco's Mission District. It quickly gained traction within the community, and in 2014 Lydia spun it out into its own independent news organization. Today, it's fully sustained by a mix of large and small donors.   In our interview, Lydia walked me through how she incorporated the site into her journalism curriculum, why she spun it out from the university, and whether she thinks Mission Local's model can be replicated across the US.  

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 hit, attracting some of the biggest names in finance. By 2020, he and a few co-founders launched Colossus, an investing-focused podcast network that now produces more than a half dozen shows across various finance niches.   In an interview, Colossus CEO Matt Reustle walked me through the vision behind the network, how it develops and promotes new shows, and why the company hasn't yet launched video versions of its podcasts.  

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 photos in exotic locales, and within a matter of weeks his income streams had completely dried up.   Luckily, he had already been batting around the idea for a podcast that didn't require any travel. In July 2020, he started producing seven episodes a week of Everything Everywhere, an educational show about a diverse range of topics, and it immediately took off. Today, it generates 1.5 million monthly downloads and pulls in much more advertising income than Gary ever made as a travel photographer.   In our interview, Gary walked through how he found his audience, where he gets his ideas for new episodes, and why he weaned himself off the social media platforms that once delivered him huge reach.  

My newsletter: https://simonowens.substack.com/   When Jared Newman launched his Cord Cutter Weekly newsletter back in 2016, the streaming TV market was much smaller than it is today, with most TV networks either not having their own streaming app or requiring a cable subscription to access it. But as it turned out, he timed his launch perfectly, as it was only a matter of years before virtually every Hollywood studio pivoted to streaming. Today, his newsletters has over 32,000 subscribers, and a spinoff newsletter that gives tech advice has also grown to 1,200 paying members.   In our interview, we discussed his motivation for launching the newsletter, why his editor let him promote it at the end of his columns, and whether he ever wants to leave his freelance career entirely to just focus on growing his two newsletters.  

My newsletter: https://simonowens.substack.com/   Today, the personal finance content niche is absolutely ginormous. You can't open up YouTube, TikTok, or Instagram without encountering an influencer who gives advice on how to make and save money.   Today's guest Philip Taylor anticipated this content explosion all the way back in 2011. That's when he launched FinCon, a conference specifically designed for personal finance content creators. That first year he attracted around 250 attendees, but over the next decade it grew into the largest conference in this niche, attracting over 3,000 attendees a year.   In our interview, Philip walked us through how he got into the personal finance space, his strategy for growing the conference, and his ambitions for launching similar conferences in other niche categories.  

My newsletter: https://simonowens.substack.com/   I'm sure just about everybody has had the experience of looking at a celebrity memoir and wondering: did they actually write that? In many cases, they didn't, at least not by themselves. There's actually an entire shadow economy of ghost writers who do the bulk of the work on these books – not just for celebrities, but all kinds of public figures ranging from big-name CEOs to politicians.   But how does one go about hiring a ghost writer? And what's it like to work with one? To answer these questions, I turned to Dan Gerstein, the founder of Gotham Ghostwriters, an agency that specializes in connecting clients to professional ghostwriters.  

My newsletter: https://simonowens.substack.com/   Ben McCarthy didn't set out to create a media company focused on Salesforce, he just began blogging about his use of the product as a way to document the various use cases he encountered. As it turned out, there were thousands of other people who were encountering those same use cases, and via Google searches they began landing on Ben's blog posts.    Fast forward 10 years, and he now runs a 20-person media company that generates over 1 million pageviews per month and is the most authoritative resource for Salesforce customers.    In our interview, we discussed why there's such a huge audience for Salesforce content, how he monetizes with webinars and white papers, and whether he wants to launch more media outlets centered around other cloud technologies.  

Get $100 your CEX tickets by entering the discount code OWENS100   My newsletter: https://simonowens.substack.com/   When Joe Pulizzi launched The Tilt in 2021, he already had a pretty good idea of how to build a successful media company. Back in 2017, he had sold his previous media startup, The Content Marketing Institute, to one of the world's largest event conglomerates.   Joe ran The Tilt with a very similar playbook – first starting with a weekly newsletter, and then expanding into an in-person conference called The Content Entrepreneur Expo, or CEX. The venture was so successful that he sold it to Lulu Press in 2023.   In our interview, Joe talked about his newsletter growth strategy, what it takes to put on a successful conference, and why he prefers the term “content entrepreneur” instead of “creator.”  

My newsletter: https://simonowens.substack.com/   When it comes to knowing all the intricacies of real estate investment, few are more knowledgeable than Brad Hargreaves. In 2015 he founded Common, a company that manages rental properties and consults  with real estate investors on building design.   And then in 2022 Brad decided to begin sharing his knowledge through a paid newsletter called Thesis Driven. Within a matter of months, it was generating six figures in revenue, and he decided to step down from his role at Common so he could focus on building out a data platform geared toward real estate investors.   In our interview, we talked about why he launched Thesis Driven as a paid only newsletter, how his content is differentiated from most other real estate journalism, and why he think there's an opportunity to build a Bloomberg Terminal for real estate investors.  

My newsletter: https://simonowens.substack.com/   I spend most of my time on this show interviewing entrepreneurs who founded English-language media outlets – mostly because that's the only language I speak – but that doesn't mean I'm not interested in the media ecosystems from other regions in the world. That's why I was super excited to talk to Andreas Sator, the host of one of the most popular podcasts in Austria.   Andreas got his start at a major newspaper, and after a few years at the outlet, he got to experiment with writing an explainer journalism column about personal finances. He found this sort of reporting to be much more enjoyable, so in 2018 he launched a podcast that roughly translates to “Explain The World to Me.”   In our interview, we discussed the Austrian podcast market, how he monetizes the podcast, and why he decided to launch a new show about climate change.  

My newsletter: https://simonowens.substack.com/   Earlier this month, I sent a newsletter to my audience with the subject line: “Ask me a question.” Basically I told everyone to jump into the comments section of the post and ask me any questions they have about the media industry or creator economy.   Several of you did pipe in with some amazing questions. I then invited on Alexis Grant, the founder of They Got Acquired, to help me answer them.   We answered questions on a range of topics like:   Which media companies are succeeding with native advertising The best ways for media outlets to run live events How to grow your audience in a world where Google and Facebook are sending less and less traffic What a Substack advertising platform would look like.  

Before William Knight launched Early Morning Media, he had worked for years at a company that specialized in sending press clippings to corporate clients. While these services were mostly utilized by a client's internal communications team, William realized at some point that these same news curation practices would be appreciated by an external audience.   So in 2011, he launched B2B newsletters covering multiple industries. At first, these newsletters were monetized mostly through paid subscriptions, but as the company expanded he began to roll out free, ad-supported newsletters as well. Today, Early Morning Media operates over a dozen newsletters that are read by 500,000 industry professionals.   In our interview, William discussed the company's origin story, its method for curating news, and the decision process for launching a new newsletter.  

My newsletter: https://simonowens.substack.com/    The rise of cloud computing introduced all sorts of benefits for the enterprise software space. Not only could license holders access their accounts from virtually anywhere, but it also allowed the software companies to issue updates on a more regular basis. But this also made the sector a lot more complicated and created a need for more experts who could educate cloud software customers about the intricacies of the tools.   Tom Arbuthnot is one of those experts. For over a decade, he's been a Microsoft MVP and Microsoft Certified Master, and he spent a significant amount of time in the early 2010s educating the public about these products through blogging and conference talks. But then in early 2022 he realized that there was a market opportunity for a media company to cover these products. That year, he launched Empowering Cloud, an online community that produces a mixture of videos, live calls, and other educational materials centered around Microsoft's cloud technology.   In my interview with Tom, we talked about the site's launch, how he finds sponsors, and why he decided to lock most of the company's content inside a community platform that requires a login.  

My newsletter: https://simonowens.substack.com/   I think everyone likes to think of themselves as being financially savvy, especially if, like me, you write about business topics, but how many of us truly understand finance terms that are bandied about like gross profit and lifetime value. Like we may know that the term EBITDA stands for “earnings before interest, taxes, depreciation, and amortization,” but how many people actually know how to calculate it?   CJ Gustafson knows. After a decade in finance, he's mastered all the accounting jargon, and a few years ago he realized that there was a market need for someone who could explain these terms in a way that's both entertaining and informative. So he launched Mostly Metrics, a Substack newsletter about finance, strategy, and operations at startups.    CJ's since grown the newsletter to over 42,000 subscribers, all while holding down his day job as a CFO at a tech startup. In my interview with him, we talked about why he launched the newsletter, how he balances his day job work and writing, and what his longterm plans are for the newsletter.  

My newsletter: https://simonowens.substack.com/   For most of Instagram's existence, it wasn't thought of as a platform for distributing news, but a growing number of media entrepreneurs have figured out ways to leverage its photo and video features to deliver engaging news digests.   One of those entrepreneurs is Sam Koslowski. Back in 2017, he and his co-founder launched The Daily Aus, a social first news outlet that's grown its Instagram account to over 500,000 followers. As it ramped up its audience on the app, it began to diversify its content offerings across newsletters, podcasts, and YouTube.   In my interview with Sam, we discussed why Instagram was the ideal platform for launching the company, how it monetizes its content, and where he hopes to expand in the coming years.  

Subscribe to my newsletter: https://simonowens.substack.com/   Ask about just any media executive, and they'll tell you that the year 2023 was not a good one for the advertising business. A combination of high interest rates and an uncertain economy made companies extremely skittish, and that caused them to pull back on their marketing spend.   There's some recent signs that advertising spending is picking up in 2024, but it's still too early to know how it will shake out.   But what about newsletter advertising? It's seen some strong growth in recent years and brands have reported higher than average ROI due to the strong engagement that's seen in the inbox. Has it suffered from the same macro economic forces that battered the larger ad industry?   To answer that question, I turned to Ryan Sager, the co-founder of Who Sponsors Stuff, a data platform that tracks sponsorships across hundreds of newsletters. Ryan dove deep into his own data to determine which sectors are investing big in newsletter ads and whether they've seen any slowdown in growth.  

My newsletter: https://simonowens.substack.com/   By the time Riad Chikhani was 16 years old, he had already built a hugely successful online community for gamers and then sold it for a healthy sum. Two years later, he founded the company that would eventually become GAMURS Group, and while it took far longer to gain traction, it eventually grew into one of the largesting gaming media companies in the world, with outlets that include Dot Esports, Gamepur, and Gamer Journalist.   In my interview with Riad, we talked about his early business pivots, why he invested big in esports, and how he drives synergies between 17 different publications.  

Earlier this month, I sent a newsletter to my audience with the subject line: “Ask me a question.” Basically I told everyone to jump in the comments section of the post and ask me any questions they have about the media industry or creator economy.   Several of you did pipe in with some amazing questions. I then invited on Alexis Grant, the founder of They Got Acquired, to help me answer them.   We answered questions on a range of topics like   How to monetize newsletters on LinkedIn How we'd go about launching a local news outlet from scratch The future of paid newsletters How The Messenger should have spent its $50 million in VC cash.   This Q&A episode is actually part of an ongoing series. Every single month I'll allow my subscribers to submit questions, and I'm going to do my very best to answer at least one question from every single subscriber. The only way to submit questions is by becoming a paid subscriber to my substack newsletter.    Subscribers also receive a calendly link from me that allows them to book a half-hour introductory phone call. Many of my subscribers use it as an opportunity to tell me about their own media businesses and pick my brain on strategy.   To subscribe, go to https://simonowens.substack.com/  

My newsletter: https://simonowens.substack.com/   When Jack Karmer and Nick Martell launched their daily newsletter Market Snacks in 2011, they kept their names off the publication so that it wouldn't jeopardize their finance day jobs. But once the newsletter started to attract readers and sponsorship revenue, they decided to come clean. Luckily, their bosses let them continue on with their side hustle.   Flash forward about a half decade, and Market Snacks had gained enough traction that they both decided to go to business school so they could learn to scale the company. Around that same time, they teamed up with a large podcast network to launch a daily companion show, and almost immediately it was featured on the Apple Podcast app.   This success didn't go unnoticed. Robinhood, which at the time was a fast-growing stock trading app, came on at first as a sponsor, but a few months later decided to outright buy Market Snacks to leverage it as a marketing channel for the app.   Jack and Nick continued to host the podcast while managing the rest of the Market Snacks team, and then in 2022 they went to the Robinhood executive team with a radical proposition: they wanted to spin off the daily podcast and acquire it from Robinhood. Amazingly, their bosses went for it, and that year they renamed the podcast to The Best One Yet.   In my interview with Jack and Nick, we discussed how they came up with the idea for the newsletter, why Robinhood allowed them to take the podcast back, and what they've done with the company ever since they became full owners.  

My newsletter: https://simonowens.substack.com/   It's no secret that local journalism has struggled since the Great Recessions, with hundreds of newspapers shuttering and thousands of reporters losing their jobs. Over the past few years, entrepreneurs have launched dozens of local news startups to help fill in the gap, but there's still an ongoing debate as to whether local news should be a for-profit or nonprofit industry.   Berkeleyside is one of the few organizations that has tried both models. For the first several years of its existence, it was a for-profit entity, but then in 2019 its founders switched it over to a nonprofit model, and it's since expanded into three separate verticals that cover the bay area, with a fourth launch planned for 2024.   In an interview, co-founder Lance Knobel walked me through how Berkeleyside came to be, why it switched to a nonprofit model, and how it generates revenue through a combination of grants, memberships, sponsorships, and large donations.  

Subscribe to my newsletter: https://simonowens.substack.com/   Lucas Grindley knows something about building sustainable revenue streams for media companies. When he was hired to Here Media, a network of LGBT news outlets, it was losing money, but over a period of six years he nurtured it back to profitability.    Now he's the executive director of Next City, a 20-year-old nonprofit magazine dedicated to urban policy and equitable cities. When he first joined, the publication was almost entirely reliant on large grants, but he's since diversified its revenue by building up its ad sales and small-donor memberships. Recently, it crossed the threshold of 1,000 paying members.   In a recent interview, Lucas walked me through his successful tenure at Here Media and explained how he's brought a similar playbook to Next City.