Well, hello there. I know, I know, it’s been a while. Life is good. My daughter is now 3, and my wife is due with our second this month. I’m still having a ton of fun at Workweek and spend most of my days studying and operating the intersection of content, community, and commerce.
So, why did I decide to come out of retirement? Partially because of why I named this newsletter Perpetual. The media industry is perpetually evolving and the swings back and forth are inevitable. My goal with this newsletter was to help people like you navigate those changes and, hopefully, help us build a better and more thriving industry. Today, I’m going to dive into what I believe is the next big change in the media industry. And this one hurts. |
The Next Media Shift Is Here |
Every decade, media goes through a massive shift. What worked before stops working. The best operators see it coming and adapt before it happens. The next shift? It’s already here, and if you're not preparing, you’re already behind. |
Almost 10 years ago, I met with my number one client from my days at Spiceworks. She had huge budgets and worked for a Fortune 100 company that spent hundreds of millions in advertising each year. I remember her calling me on the last day of her quarter, saying she had to spend $150K that day. Later, when I was moonlighting for The Hustle in our earliest days, I pitched her an ad package in our daily newsletter. I told her to think of it as “a newspaper for a tech-interested audience, delivered straight to the inbox, in the voice of Jon Stewart.” I asked for $50K for the year and promised the value it would bring. Her response? "Newsletters? Like the product that is value-added on most IOs we do together?"
Back then, newsletters were at the bottom of the food chain. No one believed they could build habits or create real relationships with readers.
Fast forward a decade, and that perception has flipped. Industry Dive, Morning Brew, theSkimm, The Hustle, and a few others paved the way, proving that the inbox wasn’t just a marketing channel—it was a daily habit. Today, brands like Netflix, Microsoft, and Facebook sponsor newsletters. Industry Dive had a massive exit. And just this week, I saw two newsletters hit 1 million subscribers. When The Hustle hit 1 million, it felt like we were on the Mount Rushmore of newsletters. Now, two companies hit that milestone in a week.
So, the futurist in me begs the question: When do the good times end? |
How We Got Here: The Shopify of Newsletters |
The rise of newsletters wasn’t an accident. It was built on a wave of democratization. The most important shift? Lowering the barrier to entry. |
Beehiiv did for newsletters what Shopify did for e-commerce.
- Shopify: Before Shopify, e-commerce was hard. You needed engineers, logistics, and payment processing. Shopify made it easy.
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Beehiiv: Before Beehiiv, running a newsletter at scale required custom engineering, growth teams, and expensive data tools. Beehiiv made those available with a click of a button.
For $99 a month, any newsletter operator can now get cohort analysis, referral tracking, and automation tools—things that used to take teams of engineers to build.
This led to mass adoption. More people started newsletters, just like more people started e-commerce brands after Shopify. More newsletters meant more competition.
And what happened in e-commerce is now happening in newsletters. |
The Danger of Mass Adoption |
Shopify empowered the bottom half of the e-commerce market but also flooded the space. That hurt the top players.
Brands like Casper, Leesa, and Allbirds got crushed as new competitors emerged. The market became saturated. Most e-commerce companies sell commodities, like mattresses, shoes, sunglasses. With Shopify making it easy to launch a brand, the big players lost their competitive edge. Suddenly, anyone could sell the same thing with similar sophistication. |
The same oversaturation is happening in newsletters and every established player should feel threatened.
Last week, I met with one of the most prominent newsletter growth agency owners because he was in Austin for a newsletter conference (yes, there are 2 of those now). He told me he’s making money hand over fist, as is almost every other agency right now.
All I could think about was this Warren Buffett quote: "Be fearful when others are greedy, and be greedy when others are fearful."
Everyone is making money on newsletters these days, which means the market is about to shift. And it won’t be in favor of operators. |
The Shift That Will Break Newsletters |
I’ve written before about the Ponzi scheme of newsletter growth, the Leaky Bucket Problem, and why together they’ve created an unsustainable path for newsletter businesses. But now there’s a bigger problem.
The way people consume information is about to change.
In e-commerce, more competition meant better options for consumers. But with newsletters, more competition isn’t necessarily good.
People don’t want more information. They want less noise.
Which is why AI-powered curation will be the next major shift in media. |
The End of the Open Inbox |
Soon, AI will decide which emails you actually see.
Think about what Gmail already does with "Promotions" and "Primary" tabs. Now take it a step further. AI will analyze which emails you open most, then create a single, personalized digest of only the most relevant content.
At first, you might say, “Not me! My newsletter has a 50% open rate!” I don’t care. Think about what you just said. At best, half of your audience isn’t opening your emails. And AI will notice. Instead of seeing 7–10 newsletters in an inbox, users will get one summary email with only the most relevant content. Instead of clicking through multiple newsletters, they’ll skim a digest. Almost like what USPS does with their preview email. |
Here’s what that means: - Email open rates will drop as people consume summaries instead of full emails.
- Ad clicks will collapse as fewer people see newsletter ads.
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The entire value of an “owned audience” declines if AI decides what gets surfaced.
If this happens, most newsletters will disappear overnight. Not dissimilar to the brands like Chegg that are getting eaten alive by the AI Overview by Google. Which brings us to the most important question: How do you avoid getting crushed? |
If AI is going to curate inboxes, you have one job as a media operator.
Be indispensable.
The best newsletters will always get through because users actively seek them out. You need to be part of their daily habit. Here’s how you protect yourself: 1. Create Content That Can’t Be Summarized - The best newsletters make readers stop scrolling.
- If your content can be boiled down to one bullet point, AI will do it for you.
- Build habit-driven content that people want to open, not just skim.
2. Own the Relationship Beyond An Email Address -
Email alone is not ownership. If AI controls inboxes, your list means nothing.
- Build SMS lists, community spaces, and direct relationships where you control distribution.
3. Don’t Be a Commodity - Most e-commerce brands failed because they sold generic products.
- Most newsletters will fail for the same reason. If you aren’t differentiated, you will be replaced.
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Have an individual at the forefront. People are unique and are memorable, most brands aren’t. Lean into creators and talented individuals to be the face of your content.
The goal is not just to “own” an audience. The goal is to be so essential that AI can’t filter you out. |
This shift is coming. AI will change how people engage with email. That means the era of high-growth newsletters is ending. The ones who survive will be the ones who own their audience relationships, create habit-driven content, and build businesses beyond the inbox. Someone on this list won’t believe me, but ask yourself, are you ready to become the Little Things of newsletters? |
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Hear from top media executives on my Perpetual podcast. |
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