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Hey—it’s Matt.
GPT-5. Claude 4.1. Cursor CLI. All dropped this week on a random Thursday.
I’ve been trying to put words to the speed and weirdness of this moment, but Greg Isenberg already nailed it (thanks, Greg). His mini-essay on this fleeting window is worth a read—and if you’re like me, it’ll make you want to double down and build.
Have a great weekend and enjoy Edition #116.
MOST INTERESTING
Flounder Mode
Kevin Kelly didn’t optimize. He “wandered with intention.” This profile breaks down how embracing detours and creative side quests helped him build a life of deep impact, without ever chasing the “next big thing.”
TOOLS + RESOURCES
Priority Compass
A deceptively simple prioritization tool that forces clarity—especially when your to-do list is starting to feel like a bug tracker. sake, more genuine habit formation. Think of it as quietly upgrading your OS.
Kyoshi
Playful pixel fonts in eight styles, full of gradients and video game nostalgia. Useful for brand moments that don’t take themselves too seriously.
Boring Websites
A curated collection of low-profile, high-margin websites. Proof that you don’t need a big swing to make meaningful revenue—you just need a useful corner of the internet.
SIGNAL + OBSERVATIONS
GPT-5
Simon Willison breaks down the new flagship LLM with a 272k context window, hybrid model lineup, and a 50% price cut over GPT-4o. It’s not just faster or cheaper—it’s the new default. And it’s very, very good.
We Are Still the Web
A welcome reminder that the open web is still alive—even if platforms want you to forget. Kevin Kelly’s 2005 essay still holds, and this follow-up proves it: user-created weirdness is still the engine.
The Design Talent Crisis
Ström calls out what a lot of design leads are quietly admitting: layoffs gutted the bench. Super ICs are doing all the work, and the next generation’s nowhere in sight. Long-term risk, short-term pressure.
CLOSING THOUGHT
The pace of change is dizzying. But the leverage to be had is real. What a time to be alive.
Stay sharp, stay building, and I’ll see you next week.
Cheers,
Matt Downey
digitalnative.news • 𝕏 • Threads
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MY STACK
These are the tools that help me run my business every day. I happily pay for each of them—they’re worth every penny. I hope you find them useful, too.
- Beehiiv → How I send this newsletter every week. 10/10 would recommend.
- Brain.fm → How I kickstart my productivity and find flow-state.
- Mercury → The best business banking I’ve ever used.
- Screen Studio → How I record engaging videos.
- Typefully → How I post content to my socials.
- Kick → My bookkeeping on auto-pilot.