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I'm a seasoned entrepreneur and technical co-founder who helps amazing people get their impactful organizations off the ground.
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Choosing to Stay Human

2026-05-29 20:22:06

A lot of the problem is going to come down to us. To be clear, I am cool with a lot of cognitive surrender. I don’t remember phone numbers anymore because my phone does that for me. I am happy my kids didn’t need to learn cursive. I am fine with calculators doing my daily math and my computer figuring out how to schedule my classes. These were once useful skills, but we were probably right to get rid of them.

AI is different because the technology is general enough that virtually any cognitive task can be offloaded into it to some degree. I don’t want to be too precious about writing: there is no principle that says a polished email draft has to come out of a human mind any more than a column of arithmetic has to. But we don’t want to give up everything, and that we mostly don’t know yet, for any specific task, what is important and what is not. Deciding that is going to be a real challenge.

My north star with technology is “am I making the computer do something useful to somebody?”

Useful, as Ethan Mollick touches on here, is the difference between “AI solved the problem for me” and “a personalized AI taught me this hard thing in a way that stuck for me.”

I’m not gonna dog on anyone who likes to write code. It’s therapeutic, it’s constant problem solving, it forces you to understand how something works.

I think software engineers tend to loudly express strong opinions that don’t meaningfully improve the problems that most people have.

AI, like every other tool, comes down to the human that is wielding it.

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Maybe Don’t Talk to the New York Times About Zohran Mamdani

2026-05-25 05:39:10

In contexts not concerning the elite private colleges of New England and their decades-old conflicts and syllabi and on-campus squabbles, this mode of prestige media procedure matters absolutely and enormously, at scales difficult to tabulate. It’s not hard to call them all to mind: “Climate change is increasingly lethal, though critics say… it is not.” Or, “Israel is murdering journalists in Gaza at historically unprecedented rates, though critics say… it is not.” Or, “Trans people claim to be real, though critics say…”

Every bit of this is disheartening on its face. But it’s actually worse than any first-blush irritation, that familiar annoyance that comes from encountering still another textbook exercise in witless triangulation. Because what this sort of reporting ultimately means is that if you have enough money to get somebody, anybody, to produce a white paper for you, which you can then put on some think-tank stationery? Then, my friend, you are ready to enter into the rushing current of elite reportage.

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Heavy metal is healing teens on the Blackfeet Nation

2026-05-13 11:02:10

This profile on the Fire in the Mountains Festival is a must-read.

I’ve been sinking deeper into a rabbit hole of punk, but this article made me want to move laterally toward exploring metal.

Tangentally related: I was browsing Apple Music the other day and saw they remastered Dethklok’s original album.

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I got a tattoo

2026-05-12 21:39:18

Me, wincing while getting my tattoo

The final product: a skull on my calf

It's not yet summer, but I'm declaring 2026 to be the summer where I "Do The Thing."

Shannon and I have been talking about getting tattoos for years now. We went to a friend's brewery's anniversary party this past weekend, and they had a tattoo pop-up stand. You could pick from one of roughly 30 tattoos.

Mine was a no brainer: skulls have been a big part of my aesthetic lately, and this one looked perfect. Slightly smiling, like I always seem to be.

Shannon's choice, a marshmallow roasting on a flame, was similarly the perfect fit for her.

I'm very motivated to make this summer memorable. We're off to a good start.

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they told me the internet was forever

2026-05-12 11:35:14

In thinking about protecting the past, I'm grateful to Brennan Brown for their post, "How are we preparing for the Long Web?," a great introduction to the web-preservation movement that's unfolding right now. I like that the tone of the post is mostly hopeful - it poises us as readers embarking on a project through time, a thought experiment into the future.

Personally, I find frameworks like React to be neat from a developer's perspective and obnoxious from nearly every single other metric.

I'm sure at some point I'll have cause to meaningfully invest time in learning a fancy Javascript front end framework, and maybe I'll eat my own hat. But boy, as the old man in the room, I have a hard time accepting that the benefits of a front end framework outweigh the downsides of increased pipeline complexity, page size, and third party dependency attack vectors.1

I say all that because I feel like React made the web more inhospitable. It's harder to archive. It requires browsers to require even more resources. It's just... greedy.

They point to some stats that highlight just how much has been lost over the past few years, one of the worst ones being that over 66.5% of links published in the last nine years are dead. Nine years. The stats can only be more devastating if we go back twenty. Brown's post hones in on the ways that digital history is disappearing & puts together a great list of the ways that webmasters and archivists can make their sites as future-proof as possible, namely by sticking to HTML/CSS3 & updating one file, not thousands. I won't re-hash Brown's entire post, but I bring it up here as an example of the ways that the decay of the internet is being stalled and how everyday webmasters are fighting back against it.

This post inspired me to go through my own links and do what I can to preserve the contents of them.

So I vibed up a feature that loops through all 700+ of my links and checks to see if they are still alive.

The results? Of the 626 links that were checked, my script couldn't access 83 links.

Of the 81 YouTube videos I've shared, six are broken.

Looking through the list of broken links made me realize I should do some more weeding around here.

Mostly I need to cut the links to topical hot takes. Sure, it was fun to dig on Sony for hiking the price of some Whitney Houston music hours after her death. But I don't need to remember that forever, right?2


  1. I accept that you could make that argument about a backend framework like Rails. Maybe I am more annoyed about the concept of an SPA? No. It's the React that's wrong. 

  2. The BBC apparently didn't, because that's one of the links that 404s. 

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“What have you tried?”

2026-05-11 08:30:56

Early on, I picked up the habit of checking with him when some technical thing or other wasn’t working the way I expected:

  • “I can’t connect to the thingamabob :(”
  • “The whatchamacallit isn’t working :(”
  • “How do I fix the doohickey?”
  • etc.

Without fail, James’s response would be not an answer but a question, one that has shaped my thinking ever since:

What have you tried?

I just stuck that on post it note and stuck it to my monitor for tomorrow morning.

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