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

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

In 2008, Wade Wallace found himself living in Australia and laid off from the company that moved him there in the first place. With his visa in limbo, and not much else to do, he launched CyclingTips, a blog that covered both the professional and amateur aspects of the sport. What started out as a hobby eventually grew into a fully-staffed news website, one that eventually sold to the investment firm that owned Outside Magazine.

Then in 2022 he quit CyclingTips, raised some investment money, and then launched Escape Collective, which covers the exact same beat. Unlike CyclingTips, Escape Collective is fully funded through paid subscriptions, and when we recorded this interview it was on the verge of profitability.

In a recent interview, Wade walked through his early days building CyclingTips, why he grew unhappy at Outside, and how he grew Escape Collective to 15,000 paying members.

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

There was a time 20 years ago where if you filmed a horror movie on a tight enough budget, you could plausibly turn a profit from the DVD sales alone. Unfortunately for Chris Sharpe, his entry into the horror genre came just as the DVD market was collapsing, and so his career as a movie director fizzled out after he made only one film. 

Luckily, one of the stars of that film, Hilah Johnson, had a strong onscreen presence and a penchant for cooking, and together they launched Hilah Cooking, a YouTube channel that eventually grew to over 450,000 subscribers. Then a few years later Chris teamed up with another co-star from that movie, Adriene Mishler, to launch Yoga With Adriene, which now has over 13 million subscribers on YouTube.

In a recent interview, Chris walked through how he and his collaborators launched both channels, why Hilah decided to eventually end her channel, and the massive success they've seen building a yoga streaming app.

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

If you ask Dave Anderson what he does for a living, he'll probably tell you he's retired, but that's not entirely true. While he did leave his last full-time job at Amazon back in 2020, he still writes a weekly newsletter on Substack about tech leadership. And even though he only works on the newsletter part time, it currently has over 2,000 paid subscribers. It turns out a lot of people want to tap into his insights gleaned from 20 years working in the tech industry, including over 10 at Amazon.

In a recent interview, Dave discussed the newsletter's origin story, how it found its audience, and why he doesn't have any ambitions to scale it into a larger media company.

By the time Emanuel Cinca launched his Stacked Marketer newsletter around five years ago, he already had a successful affiliate marketing business, but that business was largely dependent on the whims of other platforms like Facebook and Google. He wanted to build a product that he could monetize directly, and by that point he had grown to admire daily digest newsletters like Morning Brew and The Hustle.

So Emanuel decided to niche down and launch a newsletter geared toward the marketing industry. To grow the newsletter, he leveraged his skills in paid media and marketing, and today it has over 30,000 subscribers. In 2022, it generated over half a million dollars through a mixture of paid subscriptions and sponsorships.

In my interview with Emanuel, we went deep on how he designed the newsletter, his growth strategy, and how he approached monetization.

When it comes to distinctive newspaper designs, the print edition of The Financial Times stands out. The 135-year-old publication is instantly recognizable for its salmon pink paper, and it's become a status symbol for London's monied elite.

The newspaper's web presence is extremely successful as well. In early 2022, it announced it surpassed 1 million digital subscribers, an especially impressive feat given its hefty price tag of over $400 a year.

So given this success, why did the FT launch a mobile app last year that only costs around  £5 a month?

To answer this question, I turned to Malcolm Moore, a longtime Financial Times editor who was put in charge of FT Edit, which is the name for the new mobile app. We discussed why he was chosen to lead the initiative, what the app has to offer that differs from the main newspaper, and who the audience is for the product.

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

As the media industry focuses on revenue diversification, more and more publishers are venturing into live events — both virtual and in-person. Not only can they be monetized in multiple ways, but a well-planned event can provide a great venue to forge a deeper connection with your most engaged audience.

But events are tricky to pull off and can be intimidating for those who haven't hosted one before. For this episode, I pulled together a panel of people who run some of the most successful events companies in the world. They include:

Chris Ferrell, CEO of Endeavor Business Media

Bo Brustkern, co-founder of Fintech Nexus

John Allsopp, who runs one of the most influential conferences for web designers, developers, and digital creatives

Ross Douglas, founder of Autonomy Paris, a major trade show

Sarah Peck, a podcaster who launched the Wise Women's Council

Boye Fajinmi, co-founder of The Future Party

And Randy Gage, a New York Times bestselling author

In our discussion, we talked about everything including what to charge, picking a host city, finding sponsors, and negotiating with venues.

While podcasting has been around since the mid-aughts, it's only within the last half decade that the industry started generating significant revenue, finally crossing $1 billion in 2021. And until recently, there were very few journalists who were solely dedicated to writing about podcasts. That's a big part of the reason that in 2017 James Cridland decided to launch Podnews, a B2B newsletter that covers the industry.

A longtime radio veteran who once worked for the BBC, James realized that there was a major need for a daily news digest of all the various startups and media outlets that were operating in the space. And as his readership grew, he found that there were plenty of companies that were willing to pay to reach his hyper-niche audience.

In my interview with James, we talked about his approach to compiling his newsletter, his monetization strategy, and why he insists on coding most of his tools from scratch.

If you read articles about the state of local news, you'll come away with a pretty pessimistic view of the industry. But while legacy newspapers have certainly faced a steep decline, there's a burgeoning explosion of local media startups that are innovating in the space. 

One such company is Overstory Media. What started as a single local newsletter operating in Victoria has since expanded into 14 separate verticals operating all across Canada. In a recent interview, I spoke to CEO Farhan Mohamed about why he got into local news, his company's acquisition strategy, and why he's optimistic about the state of local news.

B2B used to be the least sexy space in media, but in the last decade we've seen a new crop of B2B media companies that are proving to be far more innovative than their B2C peers. Recently, I convened a panel of experts to talk about all the various aspects of B2B media — including running events, launching paid subscriptions, finding sponsors, and building out niche editorial products.

What you're about to listen to is a recording of a live Zoom call I had with my newsletter's paid subscribers. I host these calls at least twice a month, and for each one I recruit some of the world's foremost experts in media and content. If you want access to these calls, then you need to become a paid subscriber to my newsletter. Go to simonowens.substack.com. That's simonowens.substack.com.

Visit https://memberful.com/simonowens

Matt Brown didn't set off to build his own solo newsletter business, but he fell into it after taking a buyout at Vox Media sports site SB Nation during the height of the pandemic – a period when very few media companies were hiring.

While his SB Nation beat covered all of college sports, Matt decided to niche down with his own newsletter – which was called Extra Points – to focus specifically on the business side of college athletics. This gave him the edge he needed to find a loyal audience, and he quickly scaled it up to thousands of readers.

In my interview with Matt, we talked about why he left Vox Media, how he monetized his newsletter, and what made him want to sell it to a larger media company.