What I'm Reading, Saving, and Rethinking - June 6th, 2025

Practical marketing insights from the trenches: summarized, questioned, and ready for action.

Happy Friday! Every week, I save dozens of posts, articles, and newsletters that challenge my thinking. Here's what stood out this week and why I think it's worth your time too.

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🔥 This Week's Saves

Summary: The internet didn’t “sin” by choosing ads. That’s revisionist history. Ben Thompson says advertising wasn’t a mistake. Rather, it was the only monetization path that scaled when no one could pay for content directly. It funded the explosion of the web. But now the game is changing. AI agents are becoming your new browser, your new user, your new middleman. They're not clicking banner ads or watching your pre-roll. They’re reading, parsing, transacting…without human eyes.

So here’s the problem: the original ad-based web can’t survive in a world run by agents. And the new proposals to build the “agentic web” are missing the most important ingredient…payments.

Why It Matters: AI agents don’t impulse-buy. They don’t fall for clever headlines. They don’t “convert.” They just get the job done. So if we build a web optimized for them but don’t redesign the economics then we kill the incentive to create great content. No money, no media. Just a blank internet full of smart robots with nothing to read. And all those creators, publishers, and tool builders? Left holding the bag.

My Take: Ben nailed it, but I’d push harder. If AI agents are the new consumer class, then the old monetization rules are dead. Not dying. Dead. This is a once-in-a-decade unlock to fix the broken economics of the web. But instead of real innovation, we’re watching the same tech giants build protocols without profit models. We need an economic layer baked in. The solution should be invisible, programmatic, and native to the protocol. Like Stripe meets RSS meets GPT rather than 25 popups begging for Patreon donations.

Bottom Line: The agentic web is coming. Your next customer might be an LLM, not a human. If you want that future to be rich with ideas, tools, and real creators and not just corporate content farms, you better care about how they get paid.

Summary: Silicon Valley has entered its “AI Glasses Era.” Everyone, from OpenAI to Apple to Meta to Google and even Warby Parker, is building computers for your face or “AI companions” for your pocket. They share the same hallucination…that the future of consumer tech lives outside our phone. The problem is that nobody asked for this. Most of these devices are solutions in search of problems, powered more by FOMO than product-market fit.

Why It Matters: This is how tech dies, with a neck-mounted ChatGPT that can’t tell a garbage truck from a convertible. It’s not about innovation but desperation. Big Tech hasn’t had a true consumer hardware hit since the iPhone. And that’s a problem when your growth model depends on new platforms to sell new ad inventory, capture more data, and lock you deeper into their ecosystem. The scary thing is they’re spending billions betting you’ll adopt something you don’t actually want because they need a new iPhone moment.

My Take: This is classic techno-narcissism: build the thing, then pray someone finds it useful. There’s a reason these demos always take place at curated conferences with pre-approved coffee cups and polite basketball players. In the wild, these devices glitch, drain batteries, and confuse hot dogs with Labradoodles.

And yet…the valley keeps building them.

Why? Because hardware is how you capture platform power. Whoever builds the next interface sets the rules. But unlike the iPhone, these glasses aren’t solving real problems yet. They’re hoping to invent them later.

Bottom Line: Big Tech is drunk on nostalgia. They want the iPhone moment without the iPhone utility. Until these devices are:

  • cheaper than your ego,

  • more useful than your phone,

  • and cooler than looking like a cyborg tourist…

They’re toys for nerds with demo reels.

Summary: You think you’re in control of your Meta Ads account. You’re not. Jon Loomer dismantles the fantasy that manual targeting, exclusions, and placement controls give you precision. In reality? Meta’s AI takes your inputs as “suggestions,” not commands. Turning off Advantage+ or disabling AI-enhanced placements often just tanks performance and boosts your ego. The truth: you think you know more than the algorithm because of your first party data. Wrong…the algorithm knows more than you do.

Why It Matters: If you're running a startup, here’s the red pill: You’re wasting time trying to outsmart a system that’s already optimized to beat you.

  • Meta doesn’t want your micromanagement.

  • It wants your data and a clear goal.

  • Your job is direction, not domination.

You didn’t hire a world-class engineer to override their every decision, so why are you doing it to Meta’s machine?

My Take: Old-school media buyers crave control. But founders who win in 2025? They build systems. Don’t waste cycles pruning placements or toggling knobs that don’t move the needle. Focus where it counts:

  • Creative that hooks

  • Goals that align with business outcomes

  • Conversion flows that don’t leak trust

Let Meta’s black box cook. Your edge is not in micromanagement. It’s in momentum.

Bottom Line: Stop playing puppet master in a system that doesn’t need strings.

  • Meta’s AI isn’t your intern, it’s your co-pilot.

  • Focus on feeding it better creative, cleaner signals, and tighter goals.

  • Let go of the illusion of control and embrace the compounding effect of clarity + delegation.

(Don’t) fight the power!

This newsletter is for you. What marketing challenges are you facing in your marketing journey? Reply directly to this email with your questions or topics you'd like to see covered in future issues.

Until next week,

P.S. Found this helpful? Forward it to another founder who might benefit—we're all in this together.