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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. 

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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.

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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.

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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.

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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:

1. Which media companies are succeeding with native advertising

2. The best ways for media outlets to run live events

3. How to grow your audience in a world where Google and Facebook are sending less and less traffic

4. 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.

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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.

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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.

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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

1. How to monetize newsletters on LinkedIn

2. How we’d go about launching a local news outlet from scratch

3. The future of paid newsletters

4. 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/

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.

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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.

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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.

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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.

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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.

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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.

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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.

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.

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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.

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.

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.

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.