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Over the last few years, I’ve frequently wished for dumber colleagues. Each of my fellow laborers on the S.S. Every is a kind, intelligent spirit, devoted to their craft. They work incredibly hard.But wouldn’t it be better if it didn’t take a team of exclusively smart people to keep the ship afloat? Every is successful, but it's taken us working hard every single day for years to make it happen. Where I should probably want to work is Warren Buffet’s description of an investable business, one “that can be run by a ham sandwich.”
A good business has long-term defensible assets, generous profit margins, unique distribution, and, most importantly, a sense that it controls its own density. And, unfortunately, media usually has none of those things.
Internet platforms like Google and Facebook act as intermediaries between publishers and audiences, forcing media companies to constantly pivot their product on the whims of the platforms’ algorithms. Many wonderful media outfits flourished during the internet age, but most of the value that once upon a time might’ve gone to them has instead accrued to companies that aggregate consumer attention.
My colleagues have to be smart because otherwise we would get steamrolled by our market’s competitive dynamics. We have to be the best just to survive. Operationally, this means there is always the go-to media playbook: an established set of strategies and actions that are rewarded until the next technological shift. Sometimes they last a minute (like a popular meme format), sometimes for years (like the current podcast wave), but media companies live or die on the timing and speed with which they utilize trends.
In the runup to Covid, and certainly ever since, you could summarize the meta with one word: email. Email is the one distribution pipeline that isn’t owned by some mega-corporation. It gave publishers a direct method by which to communicate with users. Publishers mostly controlled the experience that readers had and knew that if they sent something, everyone on their email list would receive it. I was one of the first few employees at Substack, the platform that helped kickstart the email newsletter revolution, and I witnessed firsthand how many people were using email to build incredible businesses. The trend was so compelling that I quit my cushy tech job and became one of those people building a newsletter company. By 2025, that had led to a flourishing of niche media publications devoted to specialized topics, and new outfits like The Free Press raising a $15 million round of funding at a $100 million valuation. Just this week, Substack announced it had 5 million paid subscriptions on its platform.
However, in multiple private conversations with CEOs who run email-centered media companies over the last few months, I have heard the same thing—the era of newsletters is ending, and the media meta is shifting. The problem (and the opportunity) is AI.
Content to zero
There are four big simultaneous changes happening:
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- How the newsletter era is ending as AI reshapes media economicsCombining AI-powered content with human relationships to winSoftware as content becoming the new media bundling strategy
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