The Business of Content

How the KC Sports Network is building a regional media empire Nov 14, 2024

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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.

How Lon Seidman used his tech YouTube channel to build a huge affiliate business Nov 08, 2024

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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.

How to market a book in the age of Tiktok Oct 24, 2024

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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.

How Alts.co monetizes its massive newsletter with an investor membership platform Oct 18, 2024

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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.

How Eric Siu leveraged his hugely popular podcasts to grow his ad agency Oct 17, 2024

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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.

How Keith Pepper turned an Atlanta newspaper chain into a digital-first media company Oct 10, 2024

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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.

How Block Club Chicago reached 20,000 paying subscribers Sep 24, 2024

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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.

How State House News charges $4,000 for access to its journalism Sep 18, 2024

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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.

How Stacker distributes sponsored content to thousands of publishers Sep 11, 2024

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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.

How Mignon Fogarty launched a massively successful series of online courses Sep 05, 2024

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.

How Andrew Curtin built Construction Wave, a B2B outlet covering the UK's construction industry Sep 04, 2024

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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.

How Tim Burrowes helped build Mumbrella into a $7 million media brand Aug 21, 2024

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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.

How Alex Halperin built WeedWeek, a B2B outlet that covers California's cannabis industry Aug 08, 2024

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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.

How Mission Local spun off from UC Berkeley and became a self-sustaining news outlet Aug 05, 2024

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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.

How Colossus built one of the largest investing-focused podcast networks Jul 31, 2024

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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.

How Gary Arndt built Everything Everywhere, a podcast with 1.5 million monthly downloads Jul 17, 2024

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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.

How Jared Newman built Cord Cutter Weekly, a TV streaming newsletter with 32,000 subscribers Jun 27, 2024

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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.

How Philip Taylor built FinCon, the leading conference for personal finance creators May 23, 2024

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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.

The economics of ghostwriting books May 09, 2024

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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.

How Ben McCarthy built a Salesforce-focused media company with 400,000 monthly readers Apr 25, 2024

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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.

How Joe Pulizzi built and sold The Tilt, a newsletter and conference business geared toward creators Apr 18, 2024

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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.”

How Brad Hargreaves built Thesis Driven, a newsletter and data product focused on real estate Apr 04, 2024

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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.

How Andreas Sator built one of the most popular podcasts in Austria Mar 27, 2024

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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.

How to grow your audience in a post-Facebook world Mar 21, 2024

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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:

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.

How William Knight built Early Morning Media, a B2B newsletter company Mar 19, 2024

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.

How Tom Arbuthnot built Empowering Cloud, a media comapany focused on Microsoft cloud products Mar 14, 2024

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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.

How CJ Gustafson built Mostly Metrics, a newsletter for CFOs Mar 07, 2024

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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.

How Sam Koslowski helped build The Daily Aus, a social first media outlet in Australia Feb 28, 2024

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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.

The state of newsletter advertising in 2024 Feb 21, 2024

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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.

How Riad Chikhani built GAMURS Group, one of the largest gaming media companies in the world Feb 16, 2024

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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.

How to monetize newsletters on LinkedIn Feb 12, 2024

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/

How Jack Kramer and Nick Martell sold their media company to Robinhood and then bought it back Feb 07, 2024

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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.

How Cityside built a sustainable model for local news Feb 02, 2024

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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.

How Lucas Grindley helped Next City grow to 1,000 paying members Jan 24, 2024

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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.

Will Spotify's audiobook streaming be good for authors? Jan 18, 2024

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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.

How Gabe Fleisher built Wake Up To Politics, a daily newsletter with over 50,000 subscribers Jan 17, 2024

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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.

The biggest difference between the Creator Economy and traditional media Jan 12, 2024

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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.

Will Buzzfeed file for bankruptcy in 2024? Jan 05, 2024

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 Kelsey Ogletree built Pitchcraft, a membership community for PR pros Jan 04, 2024

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.

How Ash Read built Living Cozy, a product review site monetized with ecommerce Dec 05, 2023

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.

How Dylan Bowman built Freetrail, a media outlet for trail runners Nov 16, 2023

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.

How B2B publisher Skift scaled its business by diversifying its revenue streams Sep 04, 2023

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.

How Starter Story ditched recurring payments and built a $1.5 million information product Aug 22, 2023

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.

How Casey Keirnan built A.M. Hoops, a basketball YouTube channel with over 400,000 subscribers Jul 25, 2023

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.

How Philip Ideson built The Art of Procurement, a B2B outlet that covers a $6 billion industry Jul 19, 2023

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.

How Eric Newcomer built his tech newsletter up to over 65,000 subscribers Jul 11, 2023

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.

How Jay Shabat built Airline Weekly, one of the earliest newsletters covering the travel industry Jul 06, 2023

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.

How JR Raphael built Android Intelligence, a thriving newsletter Jun 28, 2023

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.

Simon answers your questions May 31, 2023

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This YouTuber used his channel to launch a teaching platform May 23, 2023

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.

This veteran journalist launched a thriving local news outlet May 17, 2023

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.

Taking your subscription business to the next level May 09, 2023

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

Has City Cast invented a new model for delivering local news? May 03, 2023

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

This college professor built an incredibly popular newsletter about web tools Apr 25, 2023

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.

How The Reload newsletter became a leading authority on gun policy Apr 19, 2023

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.

How to monetize with online courses Apr 11, 2023

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.

This newsletter launched its own investment fund Apr 04, 2023

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.

How Worldcrunch is bringing non-English content to a Western audience Mar 29, 2023

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.

How Matt Navarra turned his marketing newsletter into a six-figure business Mar 22, 2023

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.

How to build a career as a professional ghostwriter Mar 14, 2023

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.

How Jay Gilbert built his influential music industry newsletter Mar 08, 2023

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.

How Stacked Marketer grew to over $600k in revenue Feb 22, 2023

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.

Why The Financial Times launched an inexpensive mobile app Feb 15, 2023

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.

How to launch a successful events business Feb 08, 2023

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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.

How James Cridland built the most influential newsletter within the podcast industry Jan 31, 2023

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.

Overstory is one of the fastest-growing media companies in Canada Jan 24, 2023

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.

How to build a successful B2B media company Jan 06, 2023

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.

How Matt Brown built a thriving newsletter around the business of college sports Nov 30, 2022

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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.

How Roca News grew to 1.1 million Instagram subscribers Oct 26, 2022

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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.

Uncovered is building the largest community for true crime enthusiasts Oct 19, 2022

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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.

He sold his newsletter to a climate tech company Sep 28, 2022

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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.

How Libsyn plans to challenge Spotify for podcast dominance Sep 14, 2022

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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.

How The Future Party grew its newsletter to 150,000 subscribers Aug 31, 2022

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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.

How publishers can drive more subscription revenue Aug 28, 2022

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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.

Why Brandi Kruse left her lucrative TV news career to launch her own podcast Aug 17, 2022

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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.

How Stacker created a newswire for data journalism Aug 03, 2022

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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.

Inside Morning Brew's video strategy Jul 20, 2022

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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.

Do people want longform Twitter content? Jun 30, 2022

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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.

He transformed a B2B sports magazine into a thriving media company Jun 16, 2022

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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.

Why two star WSJ reporters left to launch their own media company Jun 01, 2022

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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.

How Payload became the leading space industry newsletter May 18, 2022

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.

How Pop Up Magazine survived the pandemic May 06, 2022

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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.

Why a bestselling author moved to Substack Apr 20, 2022

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David Kushner had the kind of mainstream success that most writers dream of. His writing regularly appeared in glossy print magazines like Wired and Rolling Stone. Several of his books became national bestsellers. And his work has even been adapted into multiple TV shows and movies.

But in 2021, David decided to bypass legacy media entirely and start publishing his work to a Substack newsletter. What drove him to do this? In our discussion, David explained how the changing norms over IP rights and his own desire to experiment with serialized storytelling motivated him to make the move.

How an investing newsletter reached 300,000 subscribers Apr 06, 2022

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When Patrick Trousdale launched his newsletter The Daily Upside in 2019, he didn’t have much of a personal brand to build from. In fact, even today, his personal Twitter account has fewer than 300 followers.

What he did have was several years of experience in finance and the willingness to grind out the newsletter each day, even when it didn’t have much of a following. That kind of persistence netted him his first few hundred followers, and it also helped him get his foot in the door so he could pitch The Motley Fool, a popular finance website, on a content partnership.

That partnership paid off in a big way, and The Daily Upside quickly grew by tens of thousands of signups. Today, the newsletter has over 300,000 subscribers and has sold out its ad inventory for months in advance.

In our interview, Patrick walked me through his initial launch strategy, his business model, and how he convinced editors at The Motley Fool to take a chance on a partnership with an unknown entity.

How Front Office Sports carved out a B2B niche Mar 23, 2022

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When Adam White graduated from the University of Miami in 2017, he had every intention of getting a job in sports administration. In fact, he went through several rounds of interviews at a major organization and was sure he’d get an offer.

But the job never actually materialized, and instead of applying to more open positions, Adam decided to double down on Front Office Sports, a website he had founded during his freshman year in college. For the next year or so, he worked part-time jobs while also spending his mornings, nights, and weekends interviewing top executives at the largest sports franchises all around the world.

His bet paid off in a big way. Not only did he manage to secure angel investment, but the site also started to attract major sponsors. Today, Front Office Sports is a powerhouse in the B2B sports media space, and it’s using its momentum to expand into new verticals.

In my interview with Adam, he explained to me what sparked his initial idea, how he became a better interviewer, and why he’d rather embrace slow growth than accept large VC investment.

His case studies generate 1 million visitors per month Mar 09, 2022

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Pat Walls’s most successful startup to date was born in the wake of a previous failed startup. Back in 2016 he and a couple other co-founders had been operating a B2B SaaS platform, but after it struggled to gain traction, they were forced to shut it down.

But Pat never lost the entrepreneurship itch, and in 2017 he started interviewing other startup founders on the phone and converting those interviews into case studies for a website called Starter Story. After a few of those case studies blew up on Reddit, Pat knew he was onto something, so he started publishing them with more frequency.

Flash forward a few years, and Starter Story now attracts over a million visitors a month, many from Google Searches. It also generates half a million dollars in annual revenue through a mixture of advertising, membership, and affiliate marketing.

How The Information covers the Creator Economy Feb 17, 2022

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When it comes to coverage of the tech sector, few publications can match the journalistic heft of The Information. Launched by former Wall Street Journal reporter Jessica Lessin in 2013, The Information quickly became an industry powerhouse, attracting some of the world’s best journalists who broke many of the biggest scoops over the past decade. If there’s a major story in tech, chances are that an Information reporter is chasing it.

So it wasn’t exactly a surprise when, in January 2021, the publication put out a job ad for a Creator Economy reporter. With an estimated $100 billion in annual revenue, the Creator Economy has not only launched the careers for thousands of creators, but it’s also become the core focus for many of the world’s largest tech platforms. Venture capitalists are now pouring billions of dollars into Creator Economy startups, and creators themselves are upending entire industries that include beauty, commerce, health, and entertainment.

In April 2021, The Information announced that it had hired Kaya Yurieff, a former CNN tech reporter, to helm its Creator Economy coverage, and she’s since launched a daily newsletter that, in addition to publishing regular feature stories, also rounds up deals, trends, and product launches.

Given the relative newness of the Creator Economy beat, I wanted to get a better idea of how Yurieff shapes her coverage. In a recent interview, she walked me through her weekly routine for news gathering, her methods for assessing startup founders’ claims, and where she thinks the industry is heading in the near future.

Building a 7-figure consulting business through Instagram Jan 27, 2022

After graduating from Harvard Law School in the early 2000s, Maria Brito was poised to have a successful career as a corporate lawyer. There was just one catch: she hated practicing corporate law.

Instead, her true passion was art. Throughout the early 2000s she started visiting New York galleries and even started to recommend pieces for purchase to her friends. Eventually, it dawned on her that high net worth individuals would pay her for the recommendations that she was giving out for free.

In 2009, Maria quit her law firm job and launched a new career as an art buying consultant. She also invested a significant portion of her time into creating online content, first with a blog and then later on social media. She eventually grew her audience to over 200,000 followers across Instagram, Facebook, Twitter, and email, and she’s leveraged this audience to sign book deals, run brand sponsorship campaigns, and bring in dozens of wealthy clients that include Gwyneth Paltrow and Sean "Diddy" Combs.

In a recent interview, she explained to me her content creation process, her philosophy on Instagram sponsorship deals, and why so many high net worth individuals trust her to buy art for their collections, often after seeing only a static iPhone photo of the piece she’s recommending for purchase.

Why a TV news reporter launched her own daily podcast Jan 12, 2022

As a CBS reporter in Los Angeles, Erica Mandy had a thriving career ahead of her in TV news. But in 2017 she quit her job and launched her own daily news podcast. It’s called The Newsworthy, and every morning it gives listeners a 12-minute rundown of the most important headlines. It also delivers weekend longform interviews with newsmakers. After four years in operation, it now generates over 800,000 downloads per month and has a growing team.

I spoke to Erica about why she made the jump from TV to podcasts, how she found her audience, and whether the daily news podcast space is becoming saturated.

Are paywalls overrated? Dec 20, 2021

The Guardian recently announced it reached 1 million paying digital subscribers. What's most incredible about the accomplishment is that the newspaper reached that number without using a paywall. Does that mean that paywalls are overrated? I sat down with Ben Cohen, editor of The Banter, to discuss whether publishers should keep all their content free.

How Science for Sport became one of the leading sports science resources Dec 09, 2021

In 2014, Owen Walker faced a predicament. He was a sports scientist at a professional football club, and his manager asked him if they should buy expensive wearable technology that would help with the team’s training. Walker turned to the internet to research whether this kind of technology was effective, but he found there wasn’t much good sports science information online.

That realization eventually led to the launch of Science for Sport, one of the leading information hubs that translates peer-reviewed sports science for a lay audience. The outlet has been embraced as a resource by pro and college teams, and Owen recently sold it to one of the world’s largest sports technology companies.

In our interview, Owen walked me through how he built the site’s audience, his monetization strategies, and why he never focused on building his own personal brand.

Can the mainstream media compete with Substack? Nov 09, 2021

Over the past few years, dozens of star journalists at mainstream media outlets announced that they were quitting their jobs to launch their own ventures, usually on platforms like Substack. As a result, some have drastically increased their income, sometimes into the seven figures.

As more and more writers defected, I and others wondered how legacy media outlets would respond. Would they adapt their business models so that their writers could capture more of the value that they generate?

Last week, The Atlantic announced that it's partnering with about a dozen writers to author standalone newsletters for the magazine. Though the partnership details are somewhat vague, they could provide a framework for how media outlets will compete with platforms like Substack moving forward.

To discuss these moves, I sat down with communications consultant Jonathan Rick. We dove into The Atlantic's newsletter strategy and discussed whether it's effective enough to lure independent journalists back into the warm embrace of legacy media.

How The Globe and Mail uses AI to drive engagement Nov 04, 2021

For the past decade, publishers have utilized metered paywalls to grow their subscription businesses. Under that model, a reader gets to view a certain number of free articles before a paywall pops up and requires them to subscribe.

But how many free articles should a user encounter before they hit a paywall?

Increasingly, the answer to that question is: It depends. Publishers are starting to roll out dynamic paywalls that assign varying weights to different kinds of stories. If you’re reading a business article, for instance, you may only get to read three free articles before hitting a paywall, but if you’re perusing real estate listings you might get unlimited free access.

The Globe and Mail has taken the idea of the dynamic paywall to the next level: it’s developed a sophisticated AI that’s able to analyze user behavior and determine the exact moment that a reader is most likely to subscribe. The AI is so powerful that the newspaper’s editors now allow it to automate the placement of stories on its homepage and social media.

I recently sat down with Gordon Edall, the person who runs the product team that developed the AI. We talked about how the paywall was initially designed, his experience recruiting data scientists, and why the Globe and Mail is licensing its AI product to other publishers.

Spotify is the newly crowned king of podcasting Nov 01, 2021

Over the past several weeks, Spotify made several major announcements in the podcast space.

It opened up its advertising ecosystem to anyone who hosts their podcasts on Anchor. It launched the ability for podcast hosts to create video versions of its podcasts. And it reported two major milestones on its quarterly earnings call: that it grew its podcast advertising revenue by 100% over the last year and that it surpassed Apple as the #1 podcast player in the U.S.

What do all these announcements mean for the podcast industry? To figure it out, I invited on Jaclyn Schiff, CEO of a company called Podreacher. We discussed whether Spotify is a threat to the open podcast ecosystem and if it can become the YouTube of podcasting.

How Google collaborates with news publishers Oct 19, 2021

Google has a long and complicated relationship with news publishers. On the one hand, it sends billions of visitors to their websites every year through its main search engine, Google News, and other products. On the other hand, some publishers believe that the Mountain View company has siphoned away ad revenue on the back of their content.

Amy Adams Harding, Google’s director of analytics and revenue optimization for news and publishing, believes the search giant has the potential to provide a net benefit to publishers. Over the past several years, her team has developed a suite of tools aimed at helping media outlets to optimize their content so it reaches a bigger audience and drives more revenue.

In our interview, Amy walked me through these tools and explained how they work. She also talked about why publishers need to adopt many of the strategies that ecommerce platforms developed over a decade ago.

The Juggernaut is hyper focused on an underrepresented market Sep 29, 2021

Snigdha Sur’s first idea for a media startup was a kind of Netflix-for-Bollywood streaming service, but when she spoke to investors about the idea, they all pointed out that it would be too easy for Netflix to simply copy her strategy.

Though she quickly scrapped that idea, she still wanted to launch some sort of outlet that would service South Asian Americans, a group that she felt was underrepresented in mainstream media. This led to the launch of a free weekly newsletter that amassed several hundred readers.

That free newsletter eventually evolved into The Juggernaut, a subscription-funded publisher that has a dedicated and growing fan base. I interviewed Snigdha about how she convinced YCombinator to let in a media startup, why she launched a hard paywall, and whether she’ll ever introduce advertising into her revenue mix.

Content creators are charging their fans for text messages Sep 08, 2021

Most subscription strategies have a pretty straightforward value exchange: in exchange for a monthly payment, the subscriber gains access to premium content that’s locked behind some kind of paywall.

But what if you want to keep all your best content in front of the paywall? What could you still offer to your audience to make a monthly subscription payment worth the price of admission?

Thousands of content creators have turned to platforms like Subtext, a tool that allows them to exchange text messages with their fans. Creators can either send mass texts out to their entire audience or get into individual conversations with subscribers.

I’ve tried out the tool myself, and it’s truly innovative. For this episode, I spoke to Subtext CEO Mike Donoghue. We talked about how his team developed the application and the different ways creators use it to generate revenue.

Yes, I'm still here Jul 15, 2021

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How the Art of Manliness monetizes its loyal audience May 28, 2021

Most major media companies are focused on scale. They want to reach ever larger audiences and then leverage that reach to drive more revenue. To accomplish this, they invest time and resources to create content across all major social platforms, from YouTube to TikTok to Snapchat.

The Art of Manliness isn’t that kind of media company. Let me give you an example of what I mean: it managed to build its YouTube channel to 1.2 million subscribers, an impressive feat, only to mostly abandon the channel several years ago. In a 2017 video, founder Brett McKay explained that there were other projects he’d rather devote his time to -- projects like writing a book, lifting weights, and producing his podcast.

According to Jeremy Anderberg, the Art of Manliness’s managing editor and one of only three full time employees, this kind of narrow focus is part of the company’s ethos. It purposefully didn’t try to scale like the BuzzFeeds and Vox Medias of the world. Instead, its team devotes nearly all of its energy into writing articles and producing a podcast, the latter of which has an incredibly loyal audience. That audience is so loyal that thousands have signed up for a 12-week bootcamp the company runs for “those who wish to revolt against our age of ease, comfort, and existential weightlessness.”

Anderberg spoke to me about how The Art of Manliness built its audience, why it launched its bootcamp, and what it’s like to work for a media company that purposefully stays small.

How Mental Floss evolved over its 20-year history May 24, 2021

In the spirit of Mental Floss’s 20th anniversary, let me give you a few pieces of trivia about the magazine. It made a cameo in two episodes of Friends and an episode of Netflix’s The OA. It started as a print magazine but discontinued its print edition in 2016. In addition to its web content, it produces several popular video series on YouTube. And in 2018, it was acquired by Minute Media, a conglomerate that mostly consists of sports media sites.

Suffice it to say, the Mental Floss of 2020 looks a lot different than when it was a magazine published out of the dorm room of two Duke University students. I recently sat down with its editor in chief Erin McCarthy to talk about its post-print strategy and why a sports media company was interested in a publisher that specializes in history trivia.

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