Welcome! I'm Simon Owens and this is my media industry newsletter. If you've received it, then you either subscribed or someone forwarded it to you.

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Freelance journalism doesn’t pay

A Substack writer wrote about why he has repeatedly passed up on opportunities to write for the New York Times:

Those with bylines in the Times, those who have so much cultural power, are not really reaping significant personal benefits outside of sporting a pretty halo of prestige. In fact, if you were a freelancer who relied on publications like the Times, you’d be at risk of being flat broke.

A former travel writer named Gary Arndt expanded on this notion in my private Facebook group:

I have a good friend from back in my travel writing days who had all the credentials. He had high-profile positions at Lonely Planet and National Geographic.

However, he didn't make much money. In fact, he was complaining about money all the time, how he wasn't getting paid by publishers and was always on the verge of ruin.

One night at a conference in Namibia, we were up late at the hotel bar throwing a few back, and I tried to convince him to start his own content business. I explained to him how it worked and that he could actually make a lot more money.

He was extremely resistant to the idea even though he acknowledged he would be financially better off.

In the end, he explicitly said that writing for the New York Times and other prestigious publications was really his biggest priority. To create his own online publishing business would lower his status among other writers because that wasn't something that high-status writers did.

After that, I realized that he and other writers I knew were never really writing for an audience. They had no connection to their actual audience. They write for other writers to achieve status in their eyes.

It’s still entirely possible to make a pretty good living as a freelance writer, but not if you want to derive most of your revenue from traditional journalism outlets. In fact, the main incentive for writing for these outlets is so that you can namecheck them when pitching yourself to potential clients. Back when I was a freelancer, the vast majority of my income came from companies that wanted me to leverage my journalism skills to write for their blogs and other content verticals, and my traditional journalism credentials merely provided me a way to differentiate myself from the competition.

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

For most of his career as a 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 Freetrail, a media outlet that operates a podcast network, a YouTube channel, and even its own ultramarathon races.

Watch our discussion in the video embedded below:

If video embeds don’t work in your inbox, go here.

ICYMI: How an interest in whiskey birthed a thriving media company

The Whiskey Wash capitalized on the rise of craft distilleries and is almost entirely funded through digital advertising.

Buzzfeed pivots from social media

I remember when BuzzFeed executives bragged that they were agnostic as to whether their audience consumed their content on social platforms vs the BuzzFeed website. Now it's shifting its focus to delivering more direct traffic:

“BuzzFeed Inc. has been, from the beginning, premised on the idea of a large network that is powerful and valuable,” [publisher Dao Nguyen] said.

“But what has happened in the past two years is that with the fragmentation of audiences, the advertising market challenges and that squeeze from the big tech platforms, the network’s value, and specifically the value of distributed-only audiences, has been rapidly diminishing, and now it’s approaching zero, and some might argue that its value is in fact negative.”

The New York Times’s blockbuster success with AI

Most of the coverage of the NYT's subscription success has focused on its content strategy, but it's also implemented an increasingly sophisticated paywall that attempts to predict the exact moment a reader is most likely to subscribe:

The model learns from the first-party engagement data of registered users and determines the appropriate metre limit to optimise for one or more business KPIs (key performance indicators) …

… The Dynamic Meter is a prescriptive machine learning model that learns the causal effect of assigning different meter limits on each user’s engagement and subscription likelihood. A weight factor combines these two objectives and can be adjusted based on business requirements, allowing the model to change the desired conversion rate flexibly.

I’m looking for more media entrepreneurs to feature on my newsletter and podcast

One of the things I really pride myself on is that I don’t just focus this newsletter on covering the handful of mainstream media companies that every other industry outlet features. Instead, I go the extra mile to find and interview media entrepreneurs who have been quietly killing it behind the scenes. In most cases, the operators I feature have completely bootstrapped their outlets.

In that vein, I’m looking for even more entrepreneurs to feature. Specifically, I’m looking for people succeeding in these areas:

• Niche news sites

• Video channels like YouTube, TikTok, and Instagram Reels

• Podcasts

• Newsletters

• Affiliate/ecommerce

Interested in speaking to me? You can find my contact info over here. (please don’t simply hit reply to this newsletter because that’ll go to a different email address. )

Henry Blodget’s vindication

Business Insider founder Henry Blodget is stepping down from his role as CEO:

He and former DoubleClick CEO Kevin Ryan co-founded the digital-media outlet in 2007, after Ryan suggested launching a “TechCrunch for New York.” The publication was first named Silicon Alley Insider, after an area in Manhattan with a large concentration of tech startups. The duo quickly ditched the New York focus after witnessing a traffic surge for stories about Apple, Blodget recalled, and the name was eventually changed to Business Insider.

Of all the media entrepreneurs to emerge out of the mid-2000s blog era — Arianna Huffington, Jonah Peretti, Nick Denton, Michael Arrington — Henry Blodget ended up being one of the most savvy. His execution wasn't flawless, but he rode the shifting waves of the digital media landscape fairly well and came out of it with a great exit and a solid reputation.

Why so many publisher ecommerce verticals produce such mediocre results

Over the last few years, nearly every mainstream publisher has launched some kind of product recommendation vertical in order to capitalize on affiliate sales, but most went about it pretty lazily:

“The truth is, most players in this space don’t test products at all,” Ben Frumin, Wirecutter’s editor in chief, told me. “Most players in the online product review and affiliate revenue space are kind of skeezy. They have a certain cynicism for their readers, and they’re like, ‘Here’s some stuff we found on Amazon without ever physically interrogating these products.’”

Do you sell a product targeted toward marketers, media executives, or professional creators?

What a coincidence! That’s exactly who reads my newsletter. You can find out how to reach them over here.

Want a daily dose of media industry news?

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