What I'm Reading, Saving, and Rethinking - July 11th, 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

TL;DR: Uber. Stripe. Reddit. Airbnb. OpenAI. We worship these brands and try to model their growth strategies. But how these brands got traction had more to do with walking a fine ethical line. Uber's Greyball helped them dodge raids and shutdowns in restricted markets. Reddit founders created hundreds of fake accounts, posting and replying among themselves to build the illusion of community. And Airbnb built a bot to scour Craigslist for housing posts and redirect users to Airbnb while using fake emails and photos to increase engagement.

Why It's Worth Your Time: This isn't to glorify bad behavior. It's to say: sometimes founders have their ethics questioned during growth or scale phase. And maybe the traditional startup advice of "build something great, listen to your users, scale organically and thoughtfully" should be questioned. We can't copy what Uber or Airbnb did (it might be illegal), but we can copy their way of thinking about a problem.

One Quote to Chew On:

"Some of the biggest companies alive today grew by playing close to the edge, they gamed distribution, hijacked attention, impersonated users, scraped what wasn’t theirs, spammed what they could, and manipulated just enough to avoid leaving a trace.”

ye_stack, r/startups

How I'm Thinking About This: These growth "hacks" were clever. Potentially illegal, but clever. And they worked. I'm reminded of the book Just Evil Enough by Alistair Croll and Emily Ross. Challenger brands make systems behave in ways its creators did not intend by finding an exploit and capitalizing on the vulnerability. "Hacking a system means wandering off the beaten path to subvert norms."

TL;DR: Most companies chase growth by layering on more…more products, more features, more audiences. But the greatest strategic move could be actually subtraction. The author argues that narrowing your focus i.e. cutting things that don't serve your core is the most powerful, underused lever in business strategy. It's how companies like IKEA (no delivery), Zara (no advertising), and Costco (limited SKUs) became dominant.

Why It's Worth Your Time: Most strategy tends to get laid on top of the basic "generic business model" common to the vertical you're in. Founders start as an undifferentiated foundation and then apply creative thinking to surface-level features. This forces them into the "cheap" vs. "premium" dichotomy. The goal, if there is already a cheap or premium player in your vertical, is to be "premium cheap."

One Quote to Chew On:

"The detail isn't really important – what's important is just the basic principle of doing strategy work at a more foundational level in order to correct legacy issues present in the wider category."

Alex M H Smith, Basic Arts

How I'm Thinking About This: We bolt strategy on top of default thinking instead of questioning the foundation itself. This article reminded me to ask:

  • What default assumptions have we accepted without critique?

  • Where are we adding complexity to solve clarity problems?

  • What would we do if we could only do one thing extremely well?

TL;DR: Ben Thompson argues that the dominant tech companies of each era emerged by riding and redefining the philosophical shift of their time. Microsoft thrived on the personal computing wave. Google won by organizing the internet. Apple succeeded by merging tech with lifestyle. Now, AI introduces a new philosophical frontier: tools that do things for you. The opportunity is not to "build with AI," but to rethink what users even need to do.

Why It's Worth Your Time: Most startups treat AI as a feature. The actual strategic unlock is philosophical. AI is ushering in a new user expectation: don't just help me do it faster, do it for me. That demands entirely new product categories, business models, and user interfaces. If you're still layering AI on top of traditional workflows, you're missing the point.

One Quote to Chew On:

"Every major shift in tech has created an opening for a new kind of company that better reflects the new philosophy of computing."

Ben Thompson, Stratechery

How I'm Thinking About This: This reset my bar for what qualifies as an "AI product." A thin GPT wrapper isn't it. A productivity tool that assumes the user still needs to do all the work, but now with smarter autocomplete, isn't it either. The winners will rethink from the ground up:

  • What's the job-to-be-done…if the user never lifts a finger?

  • What interfaces disappear?

  • What trust models need to evolve when machines act instead of assist?

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.