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Good morning - Michael here, writing from the frontlines of Massif & Kroo: Here's what you need to pay attention to in media today:

That's how many paid subscriptions Substack says it reached in 2025 — and the number is still getting referenced in 2026 as proof the platform is now a real piece of the media business.

Here's the problem nobody talks about when they celebrate that number: subscription fatigue is getting worse. And that pressure hits the middle class of creators first.

Let me explain what I mean, because this is the tension sitting underneath the entire newsletter economy right now.

Deloitte's 2026 consumer data shows meaningful chunks of households cancel subscriptions every year, and "I'm paying for too much" is one of the most common reasons. That behavior doesn't stop at streaming. It spills directly into newsletters. People subscribe fast, get excited for a week, and then clean house when the inbox starts to feel like a second job.

So you get a paradox: Substack's top line can rise while most writers stall out.

Why? Because paid subscriptions don't distribute evenly. Reuters Breakingviews noted a rule of thumb: paid conversions tend to be a small slice of the total audience, and the winners capture the bulk of the money. A few names at the top pull in six and seven figures. Everyone else is publishing into a crowded mall where the same few stores get all the foot traffic.

Substack knows this. That's why it keeps pushing "platform" moves — Notes, video, and now a TV app — to drive more discovery and more time spent inside the ecosystem. The idea is to make Substack feel less like an email tool and more like a media destination.

The problem is: those moves also make the product noisier, more competitive, and more algorithmic. That helps a small group break out. It doesn't guarantee a living for everyone. A chunk of writers hated the TV app direction specifically because it signals "more platform, less writer-first." And the writers who built Substack into what it is — the ones publishing thoughtful, quiet, niche newsletters — are the ones who feel that shift most.

Beehiiv expects to nearly double its revenue to $50 million this year, and it's pulling creators from Substack by pitching a different deal entirely: flat fees instead of a 10% cut, plus a built-in ad network that lets writers make money without asking readers to pay. About one in seven new beehiiv writers comes directly from Substack.

That's what a mature market looks like. Creators aren't just picking a platform anymore — they're shopping for better economics. And that forces every platform to justify its take.

Here's the thing most people miss about the 5 million number: it doesn't tell you how many of those subscriptions renewed. It doesn't tell you how many were free trials that converted once and churned. It doesn't tell you how the money distributes. It tells you the platform is growing. It doesn't tell you the average creator is winning.

CivicScience tracking shows more paid subscribers — across categories, not just newsletters — saying they cancel because they feel overwhelmed. Different product, same muscle memory: "I'm paying for too much stuff." That's the headwind every subscription-based creator is running into, and it's not going away.

And it's not just a consumer feeling anymore. A bipartisan bill was reintroduced in Congress to make cancelling subscriptions easier — "click to cancel" — which tells you subscription fatigue isn't just vibes. It's becoming policy pressure.

I'm not saying Substack is broken. I'm saying the story is more complicated than "5 million paid subs" makes it sound. Substack can be bigger than ever and still feel brutal for most creators. That's not a contradiction. That's the model.

This year, for the first time ever, voters were required to actually watch every nominated film in a category before casting a ballot — which sounds obvious, but apparently wasn't the rule before. The Academy is tracking views through its screening platform to enforce it.

The race is genuinely wide open: "One Battle After Another" swept the Directors Guild and Producers Guild, but "Sinners" took the SAG ensemble prize and best actor on Sunday in what everyone's calling an upset. With 16 nominations — the most in Oscar history — "Sinners" is very much alive. The last time the precursors split this cleanly, the underdog won.

U.S. and Israeli forces struck targets across Iran last weekend, killing Supreme Leader Ayatollah Ali Khamenei and dozens of senior officials. Iran has retaliated with missile strikes across the Middle East. Oil prices jumped, markets are bracing, and Congress is debating a war powers resolution this week.

The media angle: this is the first major U.S. military operation where the primary information channels aren't CNN or broadcast networks — they're social feeds, group chats, and push notifications. President Trump announced the strikes in a prerecorded video posted to social media, not a live address from the Oval Office.

Real-time footage from Tehran has been circulating on X, Telegram, and TikTok faster than any newsroom can verify it. The news organizations we talked about earlier this week — the ones forming SPUR to fight AI scraping — are now covering a conflict in real time while competing with raw, unverified video that reaches millions before any journalist can confirm what's real. That tension between speed and trust is the defining media challenge of this moment, and it's playing out right now.

YOUR NEXT MOVE: Build like fatigue is guaranteed. If you're a creator, stop assuming "turn on paid" is the business model. Treat paid as the top of a ladder, not the first rung.

Keep a strong free layer to grow reach — most people will never pay, and that's fine. Use paid for a clear, specific upgrade — not "same thing, but behind a wall." Add retention tools: annual plans, bundles, and pause options instead of just cancel buttons. Recurly's 2026 benchmarks show the subscription game is now about retention and win-backs, not endless new signups.

And diversify how you make money. Paid subscriptions are one revenue line. Ads, sponsorships, products, consulting, community access — the creators who are building sustainable businesses in 2026 aren't relying on one income stream. They're stacking them.

Substack can celebrate 5 million. You should build like that number doesn't help you. Because for most creators, it doesn't.

Thanks for reading! I’ll see you on Monday.

Feedback, thoughts, suggestions? Hit the reply!

Michael Wildes is the founder and CEO of Drive Phase Holding Company, a permanent-capital firm focused on building category-defining companies across business, media (owner of Massif & Kroo), aviation, and impact. After leaving a career as a professional pilot, he spent a year as Business Editor at FLYING Magazine writing 330+ articles on aviation's transformation. Now he builds permanent-capital companies focused on long-term trends that compound over decades. Based in Arlington, Virginia.

Connect: mikewildes.com | [email protected]

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