The Business of Content with Simon Owens – Details, episodes & analysis

My newsletter: https://simonowens.substack.com/

Like a lot of journalists in the mid-2000s, Tim Burrowes grew frustrated with his employer’s print mentality and its tendency to treat online publishing as an afterthought. At the time, he worked for an Australian trade magazine that covered that country’s media industry.

So in 2008, he and two co-founders decided to launch Mumbrella, a competing blog that published upwards of 15 times a day. Its gossipy comments section quickly attracted an audience of bored office workers, and within a few years it was hosting multiple industry events that collectively generated millions of dollars.

In a recent interview, Tim explained how Mumbrella made such a big splash so quickly, why he and his co-founders decided to sell it, and what he’s doing differently with his newest media startup. 

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When Alex Halperin launched WeedWeek in 2015, he was entering an industry that had nothing but growth ahead of it. But what he didn’t expect was that the fragmented legalization across states meant that it’d be difficult to build a national audience. So a few years ago he pivoted to just covering California’s weed industry, and WeedWeek has since built a robust business monetized through both sponsorships and subscriptions.

In our interview, Alex walked me through what got him interested in the topic, why he built a customer publishing platform, and how he recently decided to team up with the LA Times on an investigative series.

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When it comes to knowing all the intricacies of real estate investment, few are more knowledgeable than Brad Hargreaves. In 2015 he founded Common, a company that manages rental properties and consults  with real estate investors on building design.

And then in 2022 Brad decided to begin sharing his knowledge through a paid newsletter called Thesis Driven. Within a matter of months, it was generating six figures in revenue, and he decided to step down from his role at Common so he could focus on building out a data platform geared toward real estate investors.

In our interview, we talked about why he launched Thesis Driven as a paid only newsletter, how his content is differentiated from most other real estate journalism, and why he think there’s an opportunity to build a Bloomberg Terminal for real estate investors.

My newsletter: https://simonowens.substack.com/

I spend most of my time on this show interviewing entrepreneurs who founded English-language media outlets – mostly because that’s the only language I speak – but that doesn’t mean I’m not interested in the media ecosystems from other regions in the world. That’s why I was super excited to talk to Andreas Sator, the host of one of the most popular podcasts in Austria.

Andreas got his start at a major newspaper, and after a few years at the outlet, he got to experiment with writing an explainer journalism column about personal finances. He found this sort of reporting to be much more enjoyable, so in 2018 he launched a podcast that roughly translates to “Explain The World to Me.”

In our interview, we discussed the Austrian podcast market, how he monetizes the podcast, and why he decided to launch a new show about climate change.

My newsletter: https://simonowens.substack.com/

Earlier this month, I sent a newsletter to my audience with the subject line: “Ask me a question.” Basically I told everyone to jump into the comments section of the post and ask me any questions they have about the media industry or creator economy.

Several of you did pipe in with some amazing questions. I then invited on Alexis Grant, the founder of They Got Acquired, to help me answer them.

We answered questions on a range of topics like:

1. Which media companies are succeeding with native advertising

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

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

4. What a Substack advertising platform would look like.

Before William Knight launched Early Morning Media, he had worked for years at a company that specialized in sending press clippings to corporate clients. While these services were mostly utilized by a client’s internal communications team, William realized at some point that these same news curation practices would be appreciated by an external audience.

So in 2011, he launched B2B newsletters covering multiple industries. At first, these newsletters were monetized mostly through paid subscriptions, but as the company expanded he began to roll out free, ad-supported newsletters as well. Today, Early Morning Media operates over a dozen newsletters that are read by 500,000 industry professionals.

In our interview, William discussed the company’s origin story, its method for curating news, and the decision process for launching a new newsletter.

My newsletter: https://simonowens.substack.com/ 

The rise of cloud computing introduced all sorts of benefits for the enterprise software space. Not only could license holders access their accounts from virtually anywhere, but it also allowed the software companies to issue updates on a more regular basis. But this also made the sector a lot more complicated and created a need for more experts who could educate cloud software customers about the intricacies of the tools.

Tom Arbuthnot is one of those experts. For over a decade, he’s been a Microsoft MVP and Microsoft Certified Master, and he spent a significant amount of time in the early 2010s educating the public about these products through blogging and conference talks. But then in early 2022 he realized that there was a market opportunity for a media company to cover these products. That year, he launched Empowering Cloud, an online community that produces a mixture of videos, live calls, and other educational materials centered around Microsoft’s cloud technology.

In my interview with Tom, we talked about the site’s launch, how he finds sponsors, and why he decided to lock most of the company’s content inside a community platform that requires a login.

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I think everyone likes to think of themselves as being financially savvy, especially if, like me, you write about business topics, but how many of us truly understand finance terms that are bandied about like gross profit and lifetime value. Like we may know that the term EBITDA stands for “earnings before interest, taxes, depreciation, and amortization,” but how many people actually know how to calculate it?

CJ Gustafson knows. After a decade in finance, he’s mastered all the accounting jargon, and a few years ago he realized that there was a market need for someone who could explain these terms in a way that’s both entertaining and informative. So he launched Mostly Metrics, a Substack newsletter about finance, strategy, and operations at startups. 

CJ’s since grown the newsletter to over 42,000 subscribers, all while holding down his day job as a CFO at a tech startup. In my interview with him, we talked about why he launched the newsletter, how he balances his day job work and writing, and what his longterm plans are for the newsletter.

My newsletter: https://simonowens.substack.com/

For most of Instagram’s existence, it wasn’t thought of as a platform for distributing news, but a growing number of media entrepreneurs have figured out ways to leverage its photo and video features to deliver engaging news digests.

One of those entrepreneurs is Sam Koslowski. Back in 2017, he and his co-founder launched The Daily Aus, a social first news outlet that’s grown its Instagram account to over 500,000 followers. As it ramped up its audience on the app, it began to diversify its content offerings across newsletters, podcasts, and YouTube.

In my interview with Sam, we discussed why Instagram was the ideal platform for launching the company, how it monetizes its content, and where he hopes to expand in the coming years.

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Ask about just any media executive, and they’ll tell you that the year 2023 was not a good one for the advertising business. A combination of high interest rates and an uncertain economy made companies extremely skittish, and that caused them to pull back on their marketing spend.

There’s some recent signs that advertising spending is picking up in 2024, but it’s still too early to know how it will shake out.

But what about newsletter advertising? It’s seen some strong growth in recent years and brands have reported higher than average ROI due to the strong engagement that’s seen in the inbox. Has it suffered from the same macro economic forces that battered the larger ad industry?

To answer that question, I turned to Ryan Sager, the co-founder of Who Sponsors Stuff, a data platform that tracks sponsorships across hundreds of newsletters. Ryan dove deep into his own data to determine which sectors are investing big in newsletter ads and whether they’ve seen any slowdown in growth.