The Business of Content with Simon Owens

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.

Sign up for my newsletter: https://simonowens.substack.com/ It's been nearly five years since Spotify announced it would diversify its audio offerings beyond music streaming, and while it spent most of that time building its podcast capabilities, it made no secret that it eventually wanted to get into audiobooks. Then in 2022 it made its first move into the industry by acquiring an audiobooks distributor called Findaway. Later that year, it launched the ability to purchase audiobooks through spotify. And then finally in late 2023 it rolled out audiobook streaming as part of its paid subscription. There's been one group that's watched these developments closely: audiobook authors. They're understandably nervous about how Spotify's bundled offering will affect their own income, and many are deeply skeptical of the company's intentions. So will Spotify's audiobook streaming be good for authors? That's a question I put to Jane Friedman, the writer behind the publishing industry newsletter The Hot Sheet. She walked me through the current landscape of digital audiobook sales and explained how Spotify's revenue sharing arrangement works.

Subscribe to my newsletter: https://simonowens.substack.com/ There are plenty of popular politics newsletters out there, but none with the kind of unique origin story of Wake Up to Politics. It was started by Gabe Fleisher when he was only 9 years old. While the early editions were sent out by a Gmail account and only read by his mom, Gabe kept at it, waking up early every day before school to write the newsletter. Flash forward about a decade, and he's now a senior at Georgetown and Wake Up to Politics has close to 50,000 subscribers. In my interview with Gabe, we talked about what kept him motivated all these years, how he monetizes the newsletter, and what he plans to do with it once he graduates.

Subscribe to 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 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 questions, and so I spent a few hours jotting down notes and then recording this episode you're about to consume. I answered questions on a range of topics like the difference between a creator-led company and traditional media outlet, non-traditional media business models, my advice on launching a media business in 2024, and how long it takes to build a media business from scratch.

It's been a bad few years for Buzzfeed. After a disastrous IPO in 2022, it's faced a tanking stock price, declining revenue, and a shutdown of its news division. But things only look to get worse in 2024. As Adweek's Mark Stenberg reports, BuzzFeed faces a fiscal cliff where it's in danger of being delisted from the NASDAQ stock exchange, which then would trigger a required payment on its debt. Such an event would be disastrous for the company's future. I recently interviewed Mark about the dangers of the fiscal cliff and how likely it is to happen. We also discussed all the mistakes BuzzFeed made that led it up to this position.

How do you write about the travel industry when people can't fly on airplanes? That's a question Kelsey Ogletree had to ask herself in 2020 at the beginning of the pandemic. By that point, she had worked for several years as a freelance travel writer, and like many of her colleagues, she didn't know how the travel restrictions would affect her own career. So she decided to do something about it. She announced on her newsletter that she was hosting a live Zoom call about the future of the travel industry, and hundreds of people signed up to join her. That call was so successful, in fact, that she began hosting several more of them. Eventually, this ad hoc service grew into Pitchcraft, a paid membership community that costs thousands of dollars a year to join. In a recent interview I spoke to Kelsey and her husband Derrick about how they built their platform, what benefits they offer to paying members, and how they attract new customers.

Ash Read didn't launch a review website about household products because of some lifelong interest in home decor; instead, his interest came about simply because he was moving into a new house and needed to furnish it. While it was easy to search for products listed on retailers like Amazon and Walmart, he realized that there wasn't a good directory for the direct-to-consumer goods that are sold directly through a company's website. So he created a database of direct-to-consumer companies and published it to the web. The audience feedback was so strong that he decided to build out an entire website dedicated to covering and reviewing D2C home products. Ash launched Living Cozy in 2020, and over the next few years he scaled the site to over 350,000 monthly pageviews. What started out as simple product curation soon led to an in-depth review process and him hiring a network of freelance writers to review items like sofas and beds. How did Ash manage to break into such a saturated market category that was already dominated by much larger websites? In an interview, we talked about his introduction to direct-to-consumer products, his clever use of search keywords, and how he coordinated the shipment of large pieces of furniture to reviewers all over the world.

For most of his career as professional ultra marathoner, Dylan Bowman didn't have much of an online presence, but in 2019, he suddenly found himself with a lot of time on his hands after he broke his left ankle and had to take a year off from racing. That year, he launched a podcast where he interviewed his fellow pro runners, and it pretty quickly became a huge hit. It didn't take long for Bowman to realize that the podcast provided a huge opportunity for his post-racing career, so in late 2020 he and a co-founder launched Free Trail, a media outlet that operates a podcast network, a YouTube channel, and even its own ultramarathon races. In an interview, Dylan walked me through how he built the company, his monetization strategy, and why it represents the future of sports media.

In 2011, Rafat Ali launched Skift, a B2B publisher that covers the travel industry. At first, Skift was mainly monetized with advertising, but Rafat quickly realized that scaling a B2B niche outlet required a diverse set of business models that included memberships, research, events, and advertising. He also acquired multiple other media outlets that operated in adjacent industries. In an interview, Rafat walked us through this journey and explained how he managed to simplify the company's value proposition while embracing the complexity of multiple revenue models. We also spoke to Walter Frick, who ran the membership program for business publisher Quartz for nearly three years. He answered our questions about what motivates readers to convert into subscribers and what he learned when Quartz made the radical decision to completely remove its website paywall.

Patrick Walls is the founder of Starter Story, an outlet that's published thousands of case studies on how entrepreneurs built successful businesses. At one point, he was selling upward of $50k a month in sponsorships. But earlier this year, he not only stopped selling advertising, he also switched from recurring subscriptions to a one-time payment that gave customers permanent access to his content archives. The move helped him grow to $1.5 million in annual revenue. In a recent interview, he talked about why he got tired of chasing sponsors and his motivations for switching from subscriptions to one-time payments. I also spoke to Bradley Hope, a former Wall Street Journal reporter and co-author of the New York Times bestselling book Billion Dollar Whale. In 2021, he co-founded Project Brazen, a production studio that creates narrative nonfiction across podcasts, books, newsletters, TV, and film. He answered questions about how he chooses narrative projects to fund and the process for adapting a single piece of IP into multiple formats.

It used to be if you wanted to break into broadcast media you first had to start small – by getting a job as a correspondent at a local news station and then working your way up to bigger and bigger markets. That's the career trajectory that Casey Keirnan followed. He started out covering high school sports in small towns and then eventually landed a job at CBS Interactive, which was trying to create an ESPN competitor for OTT streaming. But after only two years on the job, Casey's contract wasn't renewed, and he feared he would have to go back to local news. But then he launched A.M. Hoops, an NBA-focused YouTube channel that ended up being so successful that he replaced his previous salary within a few months. Today, it boasts over 400,000 subscribers and 264 million channel views. In our interview, Casey told me about his slow climb in local news, why he struggled at his CBS job, and what inspired him to strike off on his own to start a YouTube channel.

If you run any sufficiently large organization, one of the biggest threats to your business is runaway costs. The largest companies can use upwards of thousands of suppliers for everything ranging from software technology to building materials, and how much you spend on all these suppliers can be the determining factor over whether you're profitable or unprofitable. That's why most large businesses employ procurement specialists – people whose job it is to oversee and negotiate services with outside companies. It's not the sexiest job in the world, but it's incredibly important, and it's the reason why the procurement services industry is worth $6 billion. Philip Ideson runs a media company that covers this massive industry. After spending 15 years as a procurement specialist himself, he launched The Art of Procurement, a news and information resource that caters to procurement specialists. Over the past seven years, he's built it into a business that's monetized through live events, sponsorships, and consulting. In our interview, he talked about his motivation to launch the company, how he built his audience, and why he struggled so long to find a viable business model.

There's a common criticism lodged against Substack that its model of paid subscriptions could never support original journalism, and instead it only caters to the kind of opinion journalism that can be churned out at a high rate. Eric Newcomer is proving this criticism wrong. After six years spent reporting at outlets like The Information and Bloomberg, he struck off on his own and launched a newsletter that covers startups and venture capital. Within months of his launch, he broke several major stories about top VC firms like Andreessen Horowitz and Sequoia. In our interview, Eric talked about his motivation to leave his job in traditional media, his monetization strategy, and how he manages to break major stories at such a consistent rate.

When Jay Shabat launched his newsletter in 2004, he had absolutely no experience in journalism or in operating a media company. This was also long before the era when it became easy to distribute paid newsletters. But what Jay did have was a passionate fascination with the airline industry, and he leveraged that passion to build a loyal readership. In our interview, we discussed how he found readers in a pre-social media age, his pricing strategy, and why he decided to sell the company in 2018.

Today, Android is the number one operating system for smartphones, but when Google launched the product in 2008, the iPhone already had a huge head start. Most consumers didn't know it existed, and even the tech press didn't take it super seriously. But JR Raphael was an early fan. A freelance tech journalist who wrote for publications like Fast Company and The Verge, JR pitched his editors at Computerworld on a regular column about Android, and though they were skeptical at first, they gave him the green light. As Android grew into a major mobile operating system and eventually overtook the iPhone, JR became one of the leading authorities on the product. In 2018, he launched Android Intelligence, a supplementary newsletter that mostly linked to his column and other news items, but as it picked up steam, he began to introduce more and more monetization features. By 2023, Android Intelligence was generating the majority of his annual income. In our interview, JR explained to me why he was such an early fan of Android, what motivated him to launch the newsletter, and how he turned it into a thriving business.

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In some ways, Rahul Pandey's career as a YouTuber has been pretty typical. After several years working at large tech companies like Pinterest and Facebook, he started uploading videos that gave career advice to other engineers who are trying to break into the industry. Then once he built a significant following, he left his full-time job in 2022 to focus on this type of educational content full-time. But where he differs from other YouTubers is his choice of business model. Rather than going the typical route of securing brand sponsorships, he instead co-founded Taro, an online community platform where engineers can collaborate and share career advice. The company monetizes through a monthly subscription, and to date it's mentored thousands of engineers through its community. In our interview, we discussed how Rahul built his channel, why he launched a tech platform, and what his future on YouTube now looks like.

When it comes to creating content for online audiences, few people are more experienced than Mark Talkington. He was one of the original editors of ESPN.com and then later spent 20 years as the news editor for MSN.com, the massive web portal owned by Microsoft. But starting at the beginning of the pandemic, Mark began writing for a much smaller readership: the residents of Palm Springs, California. Taking advantage of the fact that most government meetings were now being broadcast online, he spent his nights and weekends writing a daily newsletter dedicated to keeping citizens informed about their local community. The newsletter was called The Palm Springs Post, and it was an instant hit, growing to 13,000 subscribers in a little over a year. By 2022 he was able to hire another journalist and launch a second newsletter covering a nearby region. Earlier this year, he left his job at Microsoft to focus full-time on growing his company. In our interview, Mark talked about how he produced the newsletter during his free time, his business model, and what other local news entrepreneurs can learn from his approach.

Of all the media revenue models, subscriptions can be the most tricky to execute well. There are just so many variables at play that impact a publisher's ability to succeed. You have to figure out what to place both in front of and beyond your paywall, how to price your subscription, how to convert free readers into paid subscribers, and how to reduce your churn. And that's just scratching the surface. Getting one of these variables wrong can mean all the difference in determining whether a subscription business succeeds or fails. That's why I convened a panel of experts to dive into the nuances of subscription economics and identify the strategies that will increase your chances for success. They included: Peter Ericson, CEO of the Leaky Paywall subscription platform, which helps publishers seamlessly build their audience and grow paid subscriptions Michael Donoghue, CEO of Subtext, a platform that allows publishers to send text messages to their paid subscribers Jane Friedman, founder of The Hot Sheet, the most successful paid newsletter that covers the book industry Randy Cassingham, founder of This is True, possibly the world's first paid email newsletter

The local news industry has seen better days. The last 15 years or so have been pockmarked with mass layoffs, shuttered newspapers, and growing news deserts. But there have been bright spots in the local news landscape … lean media startups that aim to fill the gaps left by their legacy newspaper counterparts. One such startup is called City Cast. Founded by former Slate editor David Plotz, City Cast has a unique model in which it simultaneously launches both a daily newsletter and podcast in each city it covers. For this episode, I spoke to Bryan Vance, City Cast's director of newsletters. We discussed the company's playbook for launching in new cities, how it creates synergies between its podcasts and newsletters, and its approach to gathering local news

There's this common saying you hear in academia: those who can't do, teach. But that axiom certainly doesn't apply to Jeremy Caplan. Not only did he have a decade of reporting experience before he started teaching entrepreneurial journalism at the City University of New York, but in 2020 he launched his own entrepreneurial media outlet: Wonder Tools. Wonder Tools is a free weekly newsletter that highlights the most useful websites and apps to make your life and career easier. Since launching on Substack, it's grown to over 23,000 subscribers and it's generated a million visits in the last year. In my interview with Jeremy, we talked about his journalism career, why he went into teaching, and what compelled him to launch his own media outlet.

It's not very easy to find online coverage of the gun industry that isn't hyper polarized. The issue is dominated by a mix of NRA members and gun control activists, and even the traditional media does little more than play referee between these two sides. When Stephen Gutowski launched The Reload in 2021, his aim was to cut through this noise. Stephen had spent several years covering the issue for The Washington Free Beacon, and despite his background in conservative media, his work has been widely praised by both centrist and left-of-center journalists. In 2022, CNN hired him to serve as an on-air analyst around gun policy issues. In my conversation with Stephen, we talked about why he struck off on his own, how he monetized his newsletter, and what role his cable news career plays in building his audience.

While paid subscription models have been all the rage for the last decade, more and more creators are turning to online courses as a way to monetize their audiences. Their evergreen nature makes them ideal for generating passive income, and many creators have succeeded at selling them at relatively high price points. But what's the best way to develop a course that your audience will actually want? And how do you market it to that audience? I recently convened a panel of professional course creators to answer these questions. We talked about everything including identifying course topics, setting prices, and choosing the best platform to host your course.

Let's say you have a pile of money you're sitting on and you want to invest it. If you decide to invest it in stocks, then it's incredibly easy to track the value of your investment on a minute by minute basis. But what if you want to invest in a less-regulated asset class like, say baseball cards or art? How do you even begin to assess the price of these assets, both before and after you've purchased them? You'd probably turn to a guy like Stefan von Imhof. For the past few years, he and a co-founder have been running a newsletter focused on alternative investments. Its weekly installments go deep on various investment categories ranging from limited edition books to water rights, and it now reaches over 85,000 subscribers. The newsletter is not only monetized through the traditional models, but it also launched a fund for accredited investors, and Stefan's team has deployed millions of dollars across several asset classes. In my interview with Stefan, we talked about how he got interested in alternative investments, the steps to launching a fund, and his strategy for acquiring other newsletters.

Historically, foreign correspondents haven't been the type of journalists who break major news stories in the countries they cover. That's because they're typically not as well sourced as the local reporters who grew up in a particular region and have an intimate knowledge of its issues. But what would happen if you could take the work of local reporters and translate it for English-speaking readers? That's the idea behind Worldcrunch, a media outlet that was founded in 2011. Rather than creating all of its own content, it syndicates articles from publications all around the world and then pays translators to adapt those articles for a Western audience. In a recent interview, founder Jeff Israely talked about his years of work as a foreign correspondent for Time Magazine and how that fueled the idea for Worldcrunch. He also discussed the publication's evolving business model as it moved from syndication to advertising and subscriptions.

Before the major social platforms launch a new product, they'll often run small experiments within a subset of their users to test it out. More often than not, the first person to spot these new products is a guy named Matt Navarra, and his mini scoops have been cited in thousands of news articles over the years. Matt got his career start running the digital communications for the UK government and then later became the director of social media for The Next Web. In 2018, he struck off his own and launched his own marketing consultancy. It was that same year that he began writing Geekout, a weekly newsletter that curates emerging news and information around the marketing industry. Within a few months it amassed thousands of subscribers, and today it drives six figures in revenue, mostly through sponsorships. In my interview with Matt, we talked about where he gets his product scoops, his audience growth strategies, and how he built a six figure newsletter business as basically a side hustle.

We live in an era where every company is expected to operate as a media company and every business executive is expected to produce thought leadership content. Newsletters and blogs have become crucial mediums for establishing longterm relationships with customers, and you've probably noticed that your LinkedIn feed has been flooded with posts from CEOs and startup founders who want to share their expertise. But what happens when those CEOs don't have the time or the writing expertise needed to produce compelling content? They often turn to ghostwriters: trained journalists who are able to quickly distill executives' thoughts into shareable copy. These ghostwriters often work behind the scenes – in fact most people barely know they exist – and they can often make much more money than your average journalist. But how do you break into ghostwriting when they're effectively invisible, and what's the best way to work with clients? To answer this question, I assembled a panel of ghostwriting experts to share their experience from building their businesses.

When it comes to disruption, few industries have experienced as much upheaval over the past 20 years as the music industry. The lucrative CD era ended with the rise of Napster piracy, and the introduction of Apple's iTunes did little to stem the losses, It's only within the last decade, with the rise of streaming services like Spotify, that music revenue has begun to recover. Jay Gilbert had a frontrow seat to all of this turmoil. Working for companies like Warner Music and Universal Music Group, he got to know just about every facet of the music-making process. Then in 2015, he struck off on his own and launched a consulting business. To help raise awareness of his services, he began writing a weekly newsletter called Your Morning Coffee. What started out as an email sent out to a few hundred friends eventually grew to 15,000 readers, and it's now one of the most influential newsletters in the industry. In my interview with Jay, we talked about how the newsletter found an audience, its contribution to his consulting business, and why he doesn't want to scale it into a traditional media company.

By the time Emanuel Cinca launched his Stacked Marketer newsletter around five years ago, he already had a successful affiliate marketing business, but that business was largely dependent on the whims of other platforms like Facebook and Google. He wanted to build a product that he could monetize directly, and by that point he had grown to admire daily digest newsletters like Morning Brew and The Hustle. So Emanuel decided to niche down and launch a newsletter geared toward the marketing industry. To grow the newsletter, he leveraged his skills in paid media and marketing, and today it has over 30,000 subscribers. In 2022, it generated over half a million dollars through a mixture of paid subscriptions and sponsorships. In my interview with Emanuel, we went deep on how he designed the newsletter, his growth strategy, and how he approached monetization.

When it comes to distinctive newspaper designs, the print edition of The Financial Times stands out. The 135-year-old publication is instantly recognizable for its salmon pink paper, and it's become a status symbol for London's monied elite. The newspaper's web presence is extremely successful as well. In early 2022, it announced it surpassed 1 million digital subscribers, an especially impressive feat given its hefty price tag of over $400 a year. So given this success, why did the FT launch a mobile app last year that only costs around £5 a month? To answer this question, I turned to Malcolm Moore, a longtime Financial Times editor who was put in charge of FT Edit, which is the name for the new mobile app. We discussed why he was chosen to lead the initiative, what the app has to offer that differs from the main newspaper, and who the audience is for the product.

My newsletter: https://simonowens.substack.com/welcome As the media industry focuses on revenue diversification, more and more publishers are venturing into live events — both virtual and in-person. Not only can they be monetized in multiple ways, but a well-planned event can provide a great venue to forge a deeper connection with your most engaged audience. But events are tricky to pull off and can be intimidating for those who haven't hosted one before. For this episode, I pulled together a panel of people who run some of the most successful events companies in the world. They include: Chris Ferrell, CEO of Endeavor Business Media Bo Brustkern, co-founder of Fintech Nexus John Allsopp, who runs one of the most influential conferences for web designers, developers, and digital creatives Ross Douglas, founder of Autonomy Paris, a major trade show Sarah Peck, a podcaster who launched the Wise Women's Council Boye Fajinmi, co-founder of The Future Party And Randy Gage, a New York Times bestselling author In our discussion, we talked about everything including what to charge, picking a host city, finding sponsors, and negotiating with venues.

While podcasting has been around since the mid-aughts, it's only within the last half decade that the industry started generating significant revenue, finally crossing $1 billion in 2021. And until recently, there were very few journalists who were solely dedicated to writing about podcasts. That's a big part of the reason that in 2017 James Cridland decided to launch Podnews, a B2B newsletter that covers the industry. A longtime radio veteran who once worked for the BBC, James realized that there was a major need for a daily news digest of all the various startups and media outlets that were operating in the space. And as his readership grew, he found that there were plenty of companies that were willing to pay to reach his hyper-niche audience. In my interview with James, we talked about his approach to compiling his newsletter, his monetization strategy, and why he insists on coding most of his tools from scratch.

If you read articles about the state of local news, you'll come away with a pretty pessimistic view of the industry. But while legacy newspapers have certainly faced a steep decline, there's a burgeoning explosion of local media startups that are innovating in the space. One such company is Overstory Media. What started as a single local newsletter operating in Victoria has since expanded into 14 separate verticals operating all across Canada. In a recent interview, I spoke to CEO Farhan Mohamed about why he got into local news, his company's acquisition strategy, and why he's optimistic about the state of local news.

B2B used to be the least sexy space in media, but in the last decade we've seen a new crop of B2B media companies that are proving to be far more innovative than their B2C peers. Recently, I convened a panel of experts to talk about all the various aspects of B2B media — including running events, launching paid subscriptions, finding sponsors, and building out niche editorial products. What you're about to listen to is a recording of a live Zoom call I had with my newsletter's paid subscribers. I host these calls at least twice a month, and for each one I recruit some of the world's foremost experts in media and content. If you want access to these calls, then you need to become a paid subscriber to my newsletter. Go to simonowens.substack.com. That's simonowens.substack.com.

Visit https://memberful.com/simonowens Matt Brown didn't set off to build his own solo newsletter business, but he fell into it after taking a buyout at Vox Media sports site SB Nation during the height of the pandemic – a period when very few media companies were hiring. While his SB Nation beat covered all of college sports, Matt decided to niche down with his own newsletter – which was called Extra Points – to focus specifically on the business side of college athletics. This gave him the edge he needed to find a loyal audience, and he quickly scaled it up to thousands of readers. In my interview with Matt, we talked about why he left Vox Media, how he monetized his newsletter, and what made him want to sell it to a larger media company.

Visit Memberful: http://memberful.com/simonowens When the media outlet Roca News launched in the year 2020, it started creating just about every kind of content you can imagine. There was a newsletter, a podcast, and accounts on every single social media platform. But this everything-but-the-kitchen sink approach didn't seem to work, so the founders decided to focus mostly on a single platform: Instagram. Over the next two years, they leveraged Instagram's visual storytelling features to deliver a digestible form of news to its young followers. This singular focus allowed it to grow to over 1.1 million followers. Then, starting in 2022, it branched out into other mediums. It reinvested in its daily newsletter and also launched a TikTok account where it publishes more humorous, entertainment focused content. It also started building a dedicated mobile app, which it's launching soon. In this episode, I interviewed co-founder Max Towey about the Roca News origin story, its Instagram growth, and how it's begun monetizing its content.

My newsletter: https://simonowens.substack.com/ You've probably noticed that true crime is having a bit of a moment right now. Podcasts dedicated to the genre dominate the charts, and every week there's a new hit series on one of the major TV streaming services. Jim Brown approached true crime from a different direction. Rather than launching a show, he used his tech and product skills to build a database of cold cases. Think of it as a kind of Wikipedia for unsolved crimes. He then created ways for users to submit updates and participate in the discussion around these cases. The site, which is called Uncovered, now attracts tens of thousands of monthly visitors and recently played a key role in solving a cold case. I spoke to Jim about building the site, how it attracted its initial visitors, and its monetization strategies.

Visit https://signup.whosponsorsstuff.com/sales-pro/?source=simonowenspodcast Louie Woodall knows his way around a financial disclosure document. Since graduating college, he's worked for several media outlets that report on the intricacies of financial risk. In 2020, he decided to combine this expertise with his interest in climate change and launched Climate Risk Review, a Substack newsletter that analyzed climate disclosure documents published by major corporations around the world. The newsletter was a side hustle, but it eventually amassed an influential readership of bankers and other finance professionals, many of whom converted into paying subscribers. Eventually, Louie realized he needed to make a decision: should he continue it as a side hustle or try to make it his fulltime job? He decided on the latter option, and to help ease that transition he found a company that would not only acquire the newsletter, but also employ him to be its full time editor. In our interview, we talked about the newsletter's origin story, his monetization strategy, and how the publication will evolve under the umbrella of a larger company.

Visit Memberful: https://memberful.com/simonowens The podcast industry is around 17 years old, and Libsyn was among the first companies launched to service that industry. For most of that time, it focused on paid podcast hosting, but in recent years it's acquired companies that specialize in podcast advertising and subscriptions. Libsyn needs that more diverse product offering if it wants to compete with rising podcast behemoths like Spotify and SiriusXM. I recently sat down with Dave Hanley, who helps run its advertising operations. He told me the story behind Libsyn's acquisition of his podcast advertising platform and the company's strategy for recruiting the next generation of hit podcasts.

Check out the News Guest podcast: https://bit.ly/news-guest When Boye Fajinmi started hosting parties with a few of his friends, he had no idea that it would become a sprawling events and media company. They were just looking for a fun way to network with other creative workers like themselves. At the time, Boye worked at Paramount Pictures and was pursuing a traditional Hollywood career, but the success of those early parties led him to believe that he could build something of his own. Flash forward a decade, and The Future Party – which is what the company came to be called – now hosts dozens of events a year and works with some of the largest luxury brands in the world. It also publishes a daily newsletter that reaches 150,000 people. Boye and I sat down to discuss The Future Party's origin story, its monetization strategy, and why they decided to expand beyond events into media.

Get a 10% discount on a subscription: https://simonowens.substack.com/a30836c1 It's incredibly difficult to convert your audience from free readers/viewers/listeners into paying subscribers. In this meeting, we're going to discuss all of the optimization strategies that increase conversion and reduce churn.

Visit Memberful: https://memberful.com/simonowens In terms of career advancement, Brandi Kruse was at the top of her game. As a TV news correspondent in the large media market of Seattle, she was paid more than most of her industry peers, and she even hosted her own longform weekly talk show. But in late 2021, she quit her job and immediately launched her own podcast called Undivided. Within weeks of the launch, she amassed over 2,000 paying subscribers on Patreon, and she now delivers her commentary and interviews to over 200,000 followers across Facebook, Twitter, and YouTube. How did Brandi find this audience, and why did she ditch her well-paying job in TV? In our interview, she explained how she grew a large following on Facebook and used it as a launching pad for her independent career. She also told me about her efforts to expand beyond local news and into national politics.

Visit Memberful: http://memberful.com/simonowens Over the past decade, several major media companies have invested in building out their data journalism operations. ABC News has FiveThirtyEight, The New York Times has The Upshot. And Vox Media runs Vox.com. These outlets have leveraged publicly available data to explain complicated stories, and the infographics they create are easily shareable on social media. But most media outlets don't have the resources to hire an expensive data team, especially if they operate at the local level. That's where Stacker comes in. Rather than producing journalism for its owned and operated site, it distributes its content as a newswire that can be syndicated by any news company. What's more, it doesn't even charge for this service. That means virtually every news outlet has access to its top-quality reporting. How can Stacker afford to give away its content for free? To answer that question, I brought on co-founder Noah Greenberg. He walked me through Stacker's origin story, how it found its initial publishing partners, and how it developed its monetization strategy.

Visit SparkLoop: https://sparkloop.app/partner-network?utm_campaign=simonowens If you're aware of Morning Brew, it's probably because of its daily business newsletter. Since its founding in 2015 by two college students, it's grown to over 4 million subscribers, and its news digest format has been copied by dozens of other media startups. But since getting acquired in 2020 by Business Insider, Morning Brew has expanded into new niches in verticals. Not only has it launched several B2B industry newsletters, but it also invested heavily in podcast and video production. That's where Dan Toomey comes in. After graduating college in 2020, he pitched Morning Brew's founders on the idea of him coming on board to create video, and to his surprise, they went for it. After experimenting with several different formats, Dan started creating sketch comedy videos for TikTok, and it worked. Every morning he woke up, scanned that day's business news, and chose a topic to parody on video. In our interview, Dan talked about how he came up with the format, his daily routine for writing scripts, and Morning Brew's strategy to grow beyond TikTok and launch new video series.

Visit SparkLoop: https://sparkloop.app/?utm_campaign=simonowens If there's one thing Twitter's known for, it's character limits. It famously only allowed 140 of them and then later expanded to 280. In some ways, that forced brevity made Twitter what it is today: a real-time commentary on what's going on in the world. But for years, Twitter has been trying to expand beyond its own character limits, first by launching features like photos, gifs, and videos. It launched a threading tool that allows you to string several tweets together. In 2021, it acquired newsletter platform Revue. And then just recently, it debuted a new tool called Notes. Though it's still in the testing phase, Notes will allow users to publish longer blog posts within their Twitter feed. But is this something users actually want? Or will it eventually join the very large graveyard of social media features that never caught on? To answer this question, I brought on Ernie Smith. Not only is Ernie one of the foremost experts on publishing platforms and newsletters, he also got early access to Twitter Notes and tested them out for himself. He gave me his initial reactions to the tool and we discussed whether it would usher in an era of longform writing to Twitter.

Visit Video Husky: https://bit.ly/vh-simon-owens-pod When Nick Meacham first joined SportsPro in 2010, it mainly existed as a B2B print magazine that monetized through advertising. The editorial staff was tiny and it didn't have much of a web presence. But after taking over the business operations, he rapidly expanded it into new ventures – first by launching a series of lucrative conferences that targeted multiple industries within pro sports, and then by rapidly building out its digital operations. In an interview, Nick explained to me why he made such a big bet on events, how the company adapted during the pandemic shutdown, and where he sees more opportunities to monetize the outlet's digital content – including his plans to launch a subscription paywall.

Visit Video Husky: https://bit.ly/vh-simon-owens-pod During their combined 20 years at The Wall Street Journal, Bradley Hope and Tom Wright covered some of the most momentous stories to hit the financial world, but none were as consequential to their personal careers as their reporting on Jho Low, a Wharton grad who was caught stealing billions of dollars from investment funds. Their dogged investigation led to the publication of the book Billion Dollar Whale, an instant bestseller that transformed them into A-list writers, on par with Michael Lewis and Malcolm Gladwell. Rather than simply returning to their newspaper jobs, they partnered on a new media entity called Project Brazen. Unlike most digital media companies, Project Brazen has no ambitions to churn out large quantities of web content. Instead, it only focuses on ambitious, investigative storytelling that can be adapted into multiple mediums that include podcasts, books, film, and television. How does Project Brazen go about vetting and staffing these projects, and what are the best ways to monetize serialized storytelling? Those are some of the questions I put to co-founder Bradley Hope in today's interview.

Visit https://theygotacquired.com/newsletter When everyday people hear about space-related news, it's usually in association with an organization like NASA or SpaceX. But while Elon Musk is great at grabbing headlines, the space industry actually comprises a vast constellation of companies that generate hundreds of billions of dollars a year. And it's only set to expand; Morgan Stanley projects it'll reach $1.25 trillion by 2040. Given the size and growth of this industry, it's probably a surprise to no one who listens to this podcast that there's an enormous opportunity for the B2B media outlets that cover it. One of the most exciting entrants into that space is Payload, a daily newsletter that launched in 2021. Though Payload was bootstrapped for its first several months, it announced a $650,000 seed round last year that was led by Winklevoss Capital, the venture firm run by Cameron and Tyler Winklevoss. It's since hired an editorial staff and landed its first major sponsors. Payload was founded by Mo Islam and Ari Lewis, and in December 2021 I interviewed Mo about the newsletter's origin, its audience development strategy, and its plans to monetize its influential readership.

Visit https://www.transizion.com/ There were a lot of media companies that were vulnerable to the pandemic shutdown, but perhaps none more so than Pop Up Magazine. Not only was its content delivered through live performances, but the hosts made special care during each event to tell the audience that nothing that night would be recorded. Part of the magic, in other words, was the show's ephemerality. Of course, there was no way Pop Up Magazine could continue delivering on that promise once all in-person events went away. Instead, it had to adapt by somehow taking the magic of a live performance and delivering it over the internet. Not only did the magazine succeed in this endeavor, but the new restraints forced it to diversify revenue and expand its audience. With live events now returning, it's arguably stronger than ever. How did its staff accomplish this? In an interview last year, founder Chas Edwards walked me through Pop Up Magazine's pivot, from the hellish first weeks of the pandemic to its recent return to live events.