Nate Sullivan

Beating the System

Fri, 18 Sep 2026 09:40:59 -0400

I find software and technology very interesting, and I’ve worked at related startup companies for most of my career. But I’ve become less and less interested in what most companies are building, and definitely less interested in what the companies I’ve gotten to work for have been building. For a long time, it’s been hard to explain what I find so uninteresting and occasionally distasteful about the direction of things. While there are plenty of well documented ill-effects of technology to talk about, even working on the inside (albeit not in consumer facing scenarios most of the time) it was hard to come up with a quasi-unified theory of what was poisoning everyone’s brain and the larger culture.

Then, I figured it out. I’m sure other people have, and have probably written about it more eloquently, but for my own mental health I thought I might try to articulate it here.

The theme, over and over again, is an escape from responsibility. At this point, almost every idea seems to be an attempt to take an existing task, or job, or function, and reinvent where the person who gets paid for doing it is somehow insulated from whatever effort or accountability existed in previous versions of said work. This is not a comprehensive list, but if you just follow the key innovations of the Millennial Internet Experience, this pattern becomes pretty obvious.

Napster: you get music, for free, from other people, through a platform that facilitates this exchange but takes no accountability for it, and denies that it exists to facilitate this exchange

Facebook: originally built for connection, Facebook quickly evolved into an information platform, where it distributed and actively promoted things to you that you would normally get from newspapers, television, magazines, etc. without any accountability for what those things were, whether they were stolen, false, scams, etc.

YouTube: exact same removal of accountability for distribution and promotion, but the main focus was on taking control of distribution rights from people who made video/film/tv content, and then negotiating a profit share with those owners from a position with all the leverage (i.e., “we made a million dollars off your movie, would you like $20k or not”)

Crypto: anonymous, unregulated money, mostly to commit crimes with

Gig Work: we don’t have employees, we just make money off of dashers and drivers and day laborers and everything else, but these people are not our responsibility in any way

Metaverse: what if there were no building permits, no infrastructure, hell, no physical environment at all? Everything is pretend, and pretend things don’t have rules!

LLMs: a little bit of YouTube (normalizing theft), and a little bit of Facebook (“we didn’t do anything, it’s the algorithm, here’s how you can nudge it slightly, so honestly this is actually mostly your fault”)

Which brings us to “Agents”. We’ve had automation forever — we used to call it “programming”, kids — but never for one second did we think that we weren’t responsible for automations we programmed and then deployed. Even for things more complicated than giant if/then decision trees, where our program “decided” something, like who was in a picture, or how aggressive to be in a board game simulation, obviously the guy who set all of those parameters and thresholds (and, in our weaker moments, random number generators) was actually responsible for what the software did, right?

… right?

I should have known, given the history of technology and my proximity to it, what everyone’s fever dream would be with something like this — total lack of any accountability whatsoever. After all, you can dodge a ton of responsibility by positioning yourself correctly as a “platform” that connects two sides of a transaction where you don’t actually do anything, but ultimately there’s also a limited amount you can claim to do, and thus charge money for. But what if you owned a piece of software that could do everything a person can do in a given situation, and was understood to be completely independent from you, but couldn’t be held accountable like one? Obviously you can’t be held accountable for the actions of a completely independent, decision-making entity working on behalf of someone else, right?

… right?

The utility of any of this has always been vaguer and murkier than the utility of not being responsible or accountable for anything your product does, even when your product is out there doing stuff in the real world. This isn’t a technology innovation as much as a societal one, and from a societal perspective, it’s a bad innovation. A world where no one is responsible for anything is a bad world, we know this, we’ve experienced it, and yet capital has this absolute obsession with getting itself there. It’s literally all they care about now.

How do you get people to accept an obviously crappier social dynamic, though? Well, go back to the list.

Napster: All the music that was made because people could pay for it — well, you can have it now! For free!

Facebook: See what your friends are up to! Maybe get famous!

YouTube: Watch and share whatever you want whenever you want! Maybe get famous!

Crypto: Commit crimes! Get rich by doing nothing!

Gig Work: Be your own boss!

Metaverse: Be what you wish you were, not what you are!

LLMs: Pretend to talk to someone who knows you! Generate tons of plausible looking stuff with no effort!

These are all carrots used to make it impossible to say no to a new arrangement (even if that new arrangement is logically dependent on the old arrangement like Napster was and YouTube probably is), just because the value is so high. Some of these carrots are better than others, and you can see their impact in the uptake of things. Crypto is sort of languishing in its normal niche of criminals and speculators because the mass market doesn’t really want to commit crimes or spend their money on confusing, erratic assets. The metaverse failed because it can’t actually deliver the experience it promised. YouTube took over the world because (a) an endless pipeline of every video you’d ever want to see is awesome, and (b) it inserted itself into the way video makes money, but didn’t completely undercut it right away, so there are still good videos to be had.

LLMs and other generative AI tools are testing their proposition now. I’d say it’s a mixed bag; the number of people who want to pretend their computer loves them is more than I’d like to see, but not high enough to build an empire. The benefit of shooting out effortless work paste at the click of a button is immediately and viscerally countered by the fact that you also get this crap from your bosses, co-workers, clients, etc., and in general people absorb more than they send so the sentiment appears to be pretty negative, and getting worse.

So back to Agents. In their own way, agents are supposed to remove most or all of the responsibility for taking action in the world, which is an absolutely massive societal change that, honestly, I think almost no one really wants. It doesn’t matter if an agent goes from 65% success to 95% success, the entire thing hinges on the fundamentals of who is responsible for the action being taken. If that were addressed to people’s satisfaction, there are a million things you’d accept a 65% success rate for. If it’s not addressed to people’s satisfaction, 99.95% is not going to be good enough, because these things are computers and are going to do trillions of things, which means it’s going to break fifty billion times or whatever and all those people are going to demand recourse.

If the capital and companies pushing Agent Society so hard had a clever answer for this, or were clearly running some sort of Manhattan-Project-style effort to figure one out, I’d probably be really interested in working on agents and both the technology and society behind them. But they don’t (otherwise we’d be hearing about it), and they aren’t working on it because they don’t care. The purpose of agents is to remove responsibility and accountability as efficiently as possible. If that means pushing it to you, or the government, or the legal system, so be it, but those chips are going to fall where they may, because like YouTube, the appeal of Agent Society is going to be so overwhelming to people and businesses that they’re going to accept it.

Now, you won’t be surprised to hear that I happen to think this is wrong. Not unlike the immediate negative counter response you get from sending lazy LLM slop to coworkers, where everyone ELSE uses LLMs to send YOU lazy LLM slop that you have to deal with, accountability-free Agents make you feel the pain of their existence pretty quickly. When you send an agent to buy something, and it buys the wrong thing with your money, are you getting a refund? Will the agent do it? Will it battle with another agent? What if it fails? What if it lies? What if it buys MORE stuff with your money? Who is paying for all of this?

Just keep following this down the obvious rabbit hole. Maybe you have to approve every purchase. Okay, fine, but obviously that cuts into the productivity benefit of this. And in that case… what else do you need to approve? Does it bring you hundreds of stupid little approvals? Does it go down stupid paths that burn compute, or worse, your actual real-world resources? If you need to approve while it’s asleep, what do you do? What if one approval is necessary at the very beginning of a time-sensitive project, and you leave your agent unattended? Were you aware of this? Is anyone responsible for making you aware of it? Not today!

Again, you could go on with this forever, and a world where we’re trying to figure this out or solve it in a more realistic way than “the model will be so good it will figure out how to solve it” is a world where I probably want to work on this stuff. But that’s not the world we live in, and it’s not why there’s such a maniacal focus on this particular set of technologies. “The model will become so good…” is the only real answer from the industry precisely because it’s the only one where they can all wipe their hands of responsibility and pass it off to something else — the technology itself. They’ll just own it, and rent it. You can argue with your computer about whose fault the bad outcomes are.

If it’s not obvious, (and I suspect it’s not) this is not an anti-AI rant. I have a lot of specific AI beef, but ultimately that comes with any technology. Instead, it’s almost just a sense of melancholy over the direction of my industry, and the realization that a lot of my friends and colleagues just don’t really care about any of this. For them, there’s no pattern here, no real intent — it’s just progress, and where the animal spirits have taken the world. You can be anti-AI, or anti-Big Tech, or whatever, and there’s a mental model for that just because so many people are angry and exhausted by the world today, and the world is dominated by a couple of key technology players. But the lack of character in the industry — not just outright morals, but like, I dunno, a shared sense of responsibility not just for world-ending science fiction scenarios, but basic decency in how what we do will impact the society we were able to grow up in — is just gross, and as somebody now in my mid-40s I can tell you that it’s slowly been getting worse for a very, very long time. It’s not that things shouldn’t evolve or change. It’s that changing them thoughtlessly, or making the consequences of those changes somebody else’s problem without telling them, is just a crappy thing to do, and that should be obvious.

After two decades of consistently doing so, I haven’t worked for a tech startup since the Summer of 2025. I’ve looked at a lot of jobs since then, and to be honest, the vast, vast majority of them feel gross and uninspiring. It turns out that being desperate to make ends meet really helps you look past a lot, and in that way, not being desperate has been a huge problem for me. Maybe that problem will get “fixed”, and good old “there but for the grace of God go I” American society will kick me in the crotch, as it often does to so many people. In that case, I’ll be back to making landing pages for AI-powered debt collection call centers or whatever because I can’t afford not to, and life will go on.

I’ll probably have to delete this post, though, if I’m being honest.

"Vote for This Sleazy Lunatic"

Mon, 01 Jun 2026 16:13:08 -0400

Maybe I should just continue endlessly posting societal questions that were answered thirty years ago by The Simpsons. It's a rich vein to mine, honestly.

At any rate, here's Spencer Pratt, a reality TV "actor"/producer who is almost my exact same age but who doesn't appear to have ever had a job of any sort, running for mayor of Los Angeles, because why not?

“On the phone a few minutes later, Pratt sounds relaxed, candidly acknowledging that he doesn’t have an “answer to every question. That’s why I go around and I try to talk to people and hear what people’s issues are.” He’s a neophyte politician but seems to have a natural ease when talking with voters. “I don’t ever feel like I can get trapped because I don’t know the answer to something. I’ll tell somebody, ‘I don’t have the answer to that. I’ll look into it. I’ll get back to you.’"

We've done this. Not just the whole "elect the reality TV guy because we're bored" thing, but more importantly, the "I am tired of dissatisfying answers, let's get some satisfying ones" protest votes. There's another line in that Post editorial where two voters agree that "at least he's change". Sure! Why not vote for a tree stump? The current mayor is not a tree stump! No mayor has EVER been a tree stump!

But don't take my word for it. Listen to Springfield Sanitation Commissioner Ray Patterson. I know we're going to continue falling for this over and over again, forever, because that's just what we do. But every once in a while I like to remind people that it is, technically, a choice we make.

Are they saying "boo" or "boo-urns?"

Mon, 18 May 2026 16:05:57 -0400

Sometimes I find it hard to motivate myself to put together my thoughts about society into thoughtful, coherent arguments simply because it's unnecessary — all you really need to do is watch the first 9 or so seasons of The Simpsons and you'll understand everything around you.

Do the people hate the movies? Maybe. Do the people hate Mister Burns? Probably, I guess? But it doesn't really matter, because they definitely hate movies that reflect everything they hate about Mister Burns.

On a completely related note, this exact scenario is happening all over the place as rich, powerful people lecture new graduates about artificial intelligence technology they, in all likelihood, understand very little about. Booing a commencement speaker isn't the kind of thing that gets me riled up one way or another, but I think the media reactions to this are a useful illustration of how everyone is interpreting what this kind of thing means, and I think they happen to be wrong about it.

For one, I don't think a lot of these kids are mad about AI taking jobs. I certainly don't think the idea, or the ceaseless messaging of it helps, but the idea of a career is still a weird, ill-formed thought when you're 22-ish and sitting at your graduation. Jobs come and go, and it's not like it's ever been especially easy for a new graduate to just jump into a job, let alone one they don't despise.

But I do think almost all normal people are absolutely done with being told how everything is going to work by a pretty small group of people who (a) don't have to live inside this new reality, whatever it ends up being, because they already have enough money to build whatever kind of life they want, and (b) never face any consequences for being wrong about these predictions, which they're constantly making. People like that talk a certain way, and it sounds like this:

“You can now assemble a team of AI agents to help you with the parts that you could never accomplish on your own. When someone offers you a seat on the rocket ship, you do not ask which seat. You just get on.”

This is an insane way to talk to anyone, but an especially insane way to talk to a bunch of people who just spent four years on college diplomas. Schmidt sounds like a third-world dictator, and if you've forgotten, those guys are not usually very popular. But I bet you're not allowed to boo him in most of the places he talks, so maybe he was caught off-guard by the reaction.

“Schmidt urged graduates to embrace freedom, open debate, equality and the willingness to engage with those they disagree with.”

I'm sure he did. And while I appreciate the sentiment, Eric Schmidt is not debating anything with these people — he's lecturing to them while they have to sit there and wait to get their diplomas! And just so it's clear I'm not picking on Eric here, this is how all these guys talk. Yes, they're excited about the technology, but much more than that, they're just obsessed with getting you to build your life around it. In case you're too young or have forgotten, we had lunatics pushing internet adoption back in the 90s, too. But that excitement was almost entirely powered by possibilities (and, not coincidentally, a bunch of non-profit, open source protocols and technologies owned by no one) and really didn't require anyone to do anything they didn't want to do. For every Comic Book Guy arrogantly telling you that you'd be buying your groceries on your computer, there were hundreds of nerds just excited to show you how a message board worked, or who were happy to simply use the internet without you.

This is what brings up people's guards, and eventually turns to anger. There is just an underlying lack of real, organic belief in this technology by its biggest advocates, and you can smell it a mile a way. It's a bunch of already rich guys telling you the world needs to change in a direction that benefits them even more, and that you really, really need to make it happen.

If your hand tightens around your wallet when you hear that kind of thing, no one should blame you.

Layoffs

Tue, 05 May 2026 21:53:08 -0400

To downsize, or not to downsize? That is the question, apparently.

See, my theory is that this is because tasers are real, and Coinbase is not. Real things — workers required. Pretend things? Sure, agents. Do everything with agents. Or don't! Who cares?

The Journey

Sun, 29 Mar 2026 18:29:03 -0400

Struggling to make software work is a really specific type of experience, and you either get that mental place or you don't. As an objectively poor developer, I avoid writing code whenever possible, which is why I spend a lot of time using stuff like Bubble. But I'm not vibe-coding — every time my application doesn't do what it was supposed to, it's because of me. And when I actually figure out what's wrong, and change it, it stays that way and I move onto something else.

I think one of the reasons I've found LLM-based vibe-coding so unsatisfying has been the fact that it fundamentally alters this experience. If you're purely looking to make a computer do something, and you're not very good at that (I qualify for that designation), I get that just asking for it to happen a couple times may be a faster and ultimately better way to make the computer do it.

(It's also entirely possible that it's not faster and/or not better — this is a different discussion, but an important one for another time.)

But... it's absolutely not flexing the same muscles as building with a deterministic system. It's not using them less, it's actually not using them at all. If you've never flexed them, you might not notice. You might have a long back and forth with a chatbot, iterating on some idea, and think you've entered the sort of "flow state" your developer friends have talked about. You have not. Seriously, I am telling you, you have totally not done this. You may be in some other sort of state, and maybe that state has value, or maybe it's the future of work, or maybe you're just a guy hitting "refresh" and hoping for a different outcome, but you are not doing the thing.

Again, it's not about code. It's about systems, learning them, altering them, and ultimately mastering them. You interact with a lot of systems with code, and I suck at that, and I know that I suck at it because I've done it more than I probably should have, and I've been evaluated and coached and critiqued (heavily) by people who are really good at it. For me, failure was common, but success did happen sometimes and it's an unforgettable feeling. When I vibe-code decent stuff, it doesn't feel anything like that.

The Agency Model

The best thing I can compare this sort of thing to is working with an agency. If you've never been able to hire one, suddenly having Claude or whatever at your beck and call is probably thrilling. And sure, you can tell a chatbot to interact with you a certain way, to "partner" with you, or pretend you're pair programming even if you don't know how to program, and it will indulge you. But guess what? So will a lot of agencies. You're the customer, dummy! They'll tell you whatever you want if you let them.

I've had more or less involved roles with different agencies. I've sat there and barked orders, I've been hands off, and I've tried to save money by doing pieces of the work myself. It doesn't matter — asking for stuff is different than figuring out stuff. Really building software is not asking for things; it's doing things and creating iron-clad decision trees for things and tweaking things so that they must do what you want. No one is coming to help you. No one is going to just make it work, especially not your computer.

It doesn't have to be about building apps, either. People configure complex IT or DevOps systems, CRMs, automations, and other stuff this way, and a lot of those people get the same runner's high when they master these systems and bend them to their will.

I can't predict the future. But I can't shake the feeling that regardless of how anyone feels about any given tool, moving these experiences, these journeys, to non-deterministic finger crossing is going to create more problems than it solves. I think there's a reason many of the people most excited about eliminating the journey are people who aren't on it very often.

Narratives

Tue, 17 Mar 2026 13:23:55 -0400

I've had a lot of fun and done some cool things working at companies that lose more money than they make, but I'm not going to sit here and tell you that it's the healthiest environment. It is — by definition — an inherently untenable situation, which creates both urgency and nagging sense of existential dread. Maybe you find that motivating (I do, sometimes!), but more often than not I've found it eventually lead to paranoia and panic.

Even weirder, success in this world is often more distorting than failure, because it's so tied to fundraising and valuations. That might seem reasonable enough, until you consider that the first thing is just "someone giving you money with no oversight or rules", and the second thing is using the first thing as proof that you're making progress.

I've been doing this for a long time now, but I've never quite seen an environment like this, where two companies operating entirely inside this sort of business mirror dimension are just throwing billion-dollar-losing haymakers at each other in the hopes of being... declared the winner, I guess?

As of this post in March of 2026, it seems clear to me that Anthropic is clearly winning the perception war. Maybe that's because they're inherently less shady (although possibly more fundamentally deluded) than OpenAI, or maybe it's because they were smart enough to focus on selling to non-users (business people) instead of today's broke-ass consumers. Or maybe it's that OpenAI has been around longer, burning money longer, and is simply closer to reaching the logical, obvious end state of a company like this where it starts flailing around and trying to monetize things people only like because they're free.

Either way, Anthropic is "winning", and that means OpenAI is "losing". Are they both losing unsustainable amounts of money? Yes! Are they both relying on fundamental changes to society that don't appear to be happening yet (mass AI adoption and huge productivity improvements across white-collar work), while ignoring fundamental changes to society that do appear to be happening right in front of us (the internet it needs to function/improve turning into a cesspool of AI spam)? Most certainly, yes!

But... Anthropic is winning, you see. They're WINNING! Claude is COOL, man! It's got momentum! Have you made your crappy single page custom notes app, yet?

(Oh, I have.)

Look, a lot of this is fine. Startups need to spend money, take big swings, and figure it out later. I myself have advocated for this many times, in fact. But this whole era is taking the concept beyond even my wild desires for the ambitions of venture backed companies, largely because I never envisioned the entire economy placing one large combined bet on, essentially, one technology spread out among maybe five companies, two of which have never been in the black for one second and have no clear path to ever getting there and seemingly feel no obligation to even consider the issue.

The "winning the narrative" thing is like "winning free agency" in sports. I get where it comes from, and I get why people get excited, and I get the relevance of the challenge on the actual results of the real games that occur several months later. But we give free agency the level of primacy it gets because we're bored and there are no games at the time. We don't just replace the season with it. There are actual games to be played that matter way more!

There's a lot of hand-waving going on with the AI industry, and tech in general right now, for sure. But even when Amazon was sinking money for years and years, they could very clearly and cogently explain that choice to you. The upsides, the downsides, and how if push came to shove they could pivot to making money in a matter of weeks or months.

That's just really different than where we are now. I kinda think the people in charge know that, but the longer this goes on, the less sure I am about it, and the less confident I am in any kind of graceful landing here.

Major Scale

Tue, 17 Feb 2026 17:14:53 -0400

One thing I think a LOT of smart people misunderstand is that the power of computers is always SCALE. Computers are very fast, don't get tired, and they have no shame. If you are smart, you can point those characteristics in useful directions — and people have been doing exactly that for decades.

Large language models — especially the really, really large language models that dominate discourse and investment in 2026 — are definitely an example of this. Computers can't understand things, but they can identify extremely subtle patterns in data sets that are too massive for a person to even comprehend, and then simply respond to inputs as those patterns would. How they use those patterns to formulate output can be tweaked, or adjusted, or even randomized because all of that is just math and computers will never get tired of doing math, no matter what boring or weird or disgusting thing you make them turn that math into.

People respond to patterns too, although people are both much better and much worse at pattern recognition. They're worse because they'll never operate at the scale of a computer network, but at the same time they are vastly better at finding patterns outside of prescribed data sets, or even working with completely unstructured data they've never worked with before.

Basically:

People are slow, but they can be "prompted" by literally anything, including things like feelings, instincts, and other elements of existence that we can't even fully articulate.

Computers are very fast, but you have to structure things for them (you can try to get a computer to structure things, and sometimes with enough patterns to consult it'll figure it out, but it'll miss tons and tons of relationships that are obvious to any person).

There's a huge mistake being made (and frequently published) by even very smart, often technically competent people. That mistake is believing that human thinking is simply this kind of pattern matching done at almost incomprehensible scale, but that if we're able to build software that can do it, we'll have computers that work like people. I'm not a neurologist (or whatever the appropriate discipline is) so I can't prove this point academically, but I have spent most of my time working with software engineers, data scientists, and venture capitalists, so I can tell you that this is exactly the kind of mistake these people have been making their entire careers.

But I'm not here to judge. Instead, I'm here to warn everyone — again — that the world-shaking impact of generative, model-based software ("AI") is not going to be its ability to replace what people do, because despite what everyone is extrapolating, we don't have a ton of evidence that a lot of important work can be done effectively by a pattern matching robot, no matter how much training data it has. I guess anything could happen, but the reason I'm not that interested in it is because "high competence" is not the most likely effect of scale. We didn't see it in cloud computing, social networking, cryptocurrency, or anything else we threw money at.

Instead, the most likely effect of scale is (1) more supply, and (2) more trash. It will probably become very, very, very cheap to get an image of basically anything you can describe generated by a computer using pattern matching. If you're willing to accept VC/hyperscaler-subsidized pricing, we're already there. An entirely separate question is "how good of an image can you get from pattern matching", which depends on everything from what the image is, to how you define "good", to whether you believe in the existence of any sort of intellectual property rights. That question is extremely important if you are looking to replace the actual image creation skills that exist today with cheap, high speed pattern matching, but it's not important at all if the goal involves making tons and tons of pattern-derived middling trash.

And that's the thing! There are many business models that involve leveraging the ability to make middling trash much more quickly and easily than before. The most obvious one is spam, which is both a huge business and something predicated entirely on scale, low-cost, and finding the minimum level of plausibility necessary to work. Sure, spam is also a huge social and economic problem because it exhausts people and erodes trust, but if you make money by making spam that's someone else's problem.

Music & Spam

Music now has a spam problem. More accurately, music's existing spam problem is now exponentially worse, to the point where it's challenging the viability of the entire economic enterprise. Now, I happen to think this will get slowed or resolved simply because there's so much money in music, and it's an industry that isn't new to the idea of protecting its intellectual property. Not all of that money is smart, but I think Spotify + Labels will be better at teaming up to protect their shared interests than an army of small-time grifters.

But there's a lesson here for other industries that might not be as ready to fight spam. This is the challenge that AI will create, and it's much scarier because unlike a lot of AI doom scenarios, it's not speculation or based on extrapolating massive capability improvements that don't exist yet but maybe seem possible if you squint or just raised a Series C. AI tools can generate better spam, more spam, and forms of spam that weren't viable five years ago, and it can do it right now. The spam is stupid, of course, but almost all spam is stupid, so it doesn't matter. In fact, while AI spam is stupid, it's often less stupid than non-AI spam, not because AI is so great but because spam is so bad. It's a legitimate revolution.

Honestly, I think the term "slop" for the AI detritus we're all seeing everywhere is pretty good, so I don't have a lot of pushback on it. But I do think we should remember that in most cases, slop has the same objectives as spam. It's not to replace the work we do, but instead to overwhelm society with scale so it can collect the economic value that ordinarily would go to the superior, "real" product. When spam succeeds, it's because it is so overwhelming that the distinctions between "good" and "merely plausible" go away, and whoever gets more at-bats wins by default. Spam always gets more at-bats than real work, and AI will always get more at bats than real content.

For all of the futurism and noodling about guaranteed income or whatever, there's no real reason to think this technology won't plug into actual, current economic behaviors and systems, and simply find the shortest path to money. That's how capitalism works, especially when unchecked, and the American capitalism of 2026 is more unchecked than any in my lifetime. So maybe AI will iterate for however long it takes to generate music as good as what people make, or to become a useful workflow tool that actually improves the work musicians do (please, please, learn to mix and EQ my tracks for me). But there's no maybe about it that AI will be used to extract value from existing markets at the expense of that market, its buyers, and its sellers by third parties, because it's an incredible tool for that.

It brings me no joy to predict this, but if I'm being honest, I expect this exact type of problem to be the defining legacy of everything we're calling "AI" today.

"Am I so out of touch?"

Thu, 05 Feb 2026 15:00:04 -0400

Some time around my freshman year of college, my Dad's company gave him a phone with Windows CE on it. It quickly became a running joke in my house, because the phone was both kind of incredible, and the dumbest thing in the world. Dad hated it, surely in part because he didn't like the idea of work trying to bother him at home, but also because he was an engineer and the phone was a truly bizarre collection of choices in resource allocation. It had a bunch of Windows-style bells and whistles that made it sort of feel like Windows, but was laughably bad at basically any task you'd ever actually want to do on the phone. It took forever to turn on. It was impossibly slow. Even getting and responding to an email was a huge chore with a fiddly little plastic stylus. If you had asked us in 2002 whether smartphones would take over the world in less than a decade, I think we would have had a good laugh.

The two major shifts that changed that trajectory were the Blackberry, and the iPhone. I never had a Blackberry, but I remember my wife's office giving her one temporarily for some reason, and the difference in philosophy was obvious. I have no idea how many different things the Blackberry did or presumed to do, but it was really, really good at reading and sending short emails. I know this because my wife (at the time) had zero experience doing anything productive on a smartphone — I'm not even sure we knew how to text each other yet — and within a couple hours she looked like a legislative aide trying to push a bill through committee. She was hooked to that thing, to the point that I made her promise not to keep it if they let her. But as a pure messaging product, the Blackberry was a home run because (at least at first) it made vastly better resource prioritization decisions and focused entirely on making the useful experience of triaging emails while on the go better.

The iPhone was an even more impressive achievement because it made Blackberry-level allocation and optimization decisions in service of Microsoft's much more ambitious goal, which was mobile, general purpose computing. And while, without a doubt, there were (and continue to be) amazing hardware innovations that made the iPhone idea work, they were all in service of software that was extraordinarily well-designed and built for the task. Multitouch hardware is cool, but multitouch hardware attached to an entire platform built around pinching and pulling and tapping actually solves many of the problems Windows CE simply stared at blankly and hoped people would accept.

Today, it's easy enough to think about my Dad's old phone (or "Pocket PC", or whatever it was called back then) and think that Microsoft basically had this right and just dropped the ball. But they never actually had it, because their "it" was just "small computers". They could have banged away at that for another twenty years with incrementally better hardware and made the horrendous, Start-menu-clicking Windows CE experience marginally better, but they never actually would have figured out what we have today. They were never going to solve a problem that required transcendently great software because they make shitty software and they don't think that's a problem. Instead, their solution was to push their laughably bad devices (sorry, "partner devices") to corporate customers and try to pressure the world into adopting them. In fact, it's a credit to Microsoft's incredible sales and distribution skills that people like my Dad even had these devices in their hands at all, as they provided almost zero utility, were pretty expensive, and generated absolutely no mainstream, organic demand. They were stupid, fundamentally broken, almost nobody wanted them, and yet through sheer force of dollars and executive desire, they were a real product category and frequently discussed in business media as "the future".

Sound familiar?

"No... it's the children who are wrong."

Ultimately, I think mobile "happened" because the software that powered it and defined the experience for the people using it made those massive leaps. The Blackberry made people realize the "tiny Windows PC" concept was stupid and insufficiently useful, and the iPhone gave people a fundamentally different way to interact with small devices that made them not just usable, but so usable that people became comfortable using them instead of desktops and laptops in many (most?) circumstances. There was no "adoption" problem because the products made obvious sense. In fact, at the enterprise level, the problem was backwards — companies didn't know how to deal with the fact that everyone wanted to use their mobile device for work, and they actually dragged their feet and tried to slow the whole thing down.

One of the massive red flags about this generation of "AI" technology is the increasingly frequent (to the point of being almost constant now) reference to those pesky "adoption" problems. I get a little salty about "adoption" because it's the kind of thing people complain to Product Marketing about, and feel like my team should be able to fix, or have prevented in the first place. And sure, every so often, there's an awareness or education problem, and that's something we can tackle. But much more frequently, people are aware of what we want them to do, and they do know how to do it. They just don't want to do it, dislike the process of doing it, or don't think it's worth the effort. As a last ditch effort, I can always argue with them about it, but the honest truth is that if you're arguing, you're losing. We probably just made something no one wants or needs, or maybe even something that is actively bad.

Windows CE had adoption problems, too. I guess we could have written op-eds about how the world of 2002 needed to "transform itself" into a "mobile-first" world — I assume people wrote these, honestly — but none of that actually happened because the world wasn't going to reorganize itself to mitigate the problems of new, unproven products caused by shitty, uncreative software. In reality, the world only grudgingly adapted once transcendently great software made these products shockingly, undeniably useful for interacting with the world around them. Adaptation is a reaction, after all. Businesses don't preemptively adapt to anything unless they really enjoy wasting time and money.

If generative AI actually matters, its utility or ease of use will force the changes today's investors and consultants are insistent that we make ahead of time — a trail to be blazed, so to speak, versus a red carpet to be rolled out. To the extent those changes exist today, they have very little to do with legitimate business and a lot more to do with society, as generative AI's most dramatic efficiency improvement so far has been the creation of spam, slop, and disinformation. The world really is scrambling to adapt to massive adoption of the technology by bad actors, because their preferred workflows really are better with software that uses this technology. It's disgusting and gross, but it's not illogical, and it doesn't require think pieces on adoption.

But these use cases, in addition to being socially dubious, are also pretty niche in the grand scheme of things. For returns that justify the investments being made, it's going to take great, innovative software that turns whatever value exists in probability-based asset generation into something useful and accessible to people. Hilariously though, the one legitimate area this technology seems to be impacting is... creative software development! That's right — creating derivative, marginally customized versions of software that have existed forever is now incredibly cheap, and incredibly compelling to companies. So while what the industry desperately needs is a completely new set of original software ideas, that same industry is aggressively discouraging craft and originality in software. In short, I don't believe generative AI will really matter to the broader economy (outside of unsustainable data center expenditures) by remixing old ideas and conventions. It's just not that kind of innovation. We got away with — and I personally profited from — twenty years of building cloud-based versions of things that we knew people wanted and needed. And while it didn't work every time, there were tons and tons AND TONS of cases where that made sense, and simply bolting "internet" onto something useful made it better for a variety of reasons. That same approach is clearly being taken by today's AI founders (stick AI onto things), but the benefits of AI are way, way more nebulous, the downsides more obvious, and the costs higher than anything in the cloud era, and you're seeing that manifest in the "adoption problem" that simply isn't going away.

There's some amount of time you can just charge ahead and hope some version of Moore's Law becomes apparent and everything just becomes easier on its own. That certainly seems to be the plan, albeit one crafted and promoted by a bunch of executives my age and younger who have been drafting off of the actual Moore's Law their entire professional lives. I'm not sure they know what else to try, which is yet another reason why I think this is going to end very, very badly.

Push, push, push

Tue, 03 Feb 2026 22:00:39 -0400

Football has always had problems, but from a fan experience perspective, it was basically the perfect setup for a long, long time. The sport simply owned Sunday afternoons, and in many ways, Monday night, not just because it was popular, but because it was so well engineered. No baseball/basketball/hockey-style fatigue or regular season grind, everything happening at once, everything important all the time. The league printed money, dominated TV and culture, and set whatever terms it wanted in everything it did.

But... it wasn't enough. And it never will be. Now, football is on too much. Thursday night games suck. There are random bad games in Europe at odd hours. The 16 game schedule is now 17 games, with a corresponding increase in injuries that make the results a little less about skill, and a little more about depth and attrition. Instead of just being "on", games are gated behind stupid services like Peacock, and Amazon Prime. Things are basically the same, just a little bit worse every year.

People can feel it. Football is still a dominant money machine, but almost no one is a fan of the direction the league is moving. And even that's not enough, because nothing is enough. Now the owners want 18 games, consequences be damned.

"I want to tell you guys that we're going to push like the dickens now to make international [games] more important with us," Kraft told the "Zolak & Bertrand" show. "Every team will go 18 [regular-season games] and two [preseason games] and eliminate one of the preseason games, and every team every year will play one game overseas."

I gotta tell you, I hate that everything is like this. We sometimes reprimand my intense, ambitious daughter for constantly pushing the envelope in an attempt to get the most out of things, or move them in the direction she wants. "Push, push, push", my wife will say, to remind her how exhausting it is to have even wonderful things stretched and exploited and distorted until they become frustrating facsimiles of themselves.

For our sake, we hope she reigns it in as she grows up, but if I'm being honest, I don't think it's a quality that will keep her from being successful. Maybe she'll own an NFL team.

Abolishing Things

Wed, 21 Jan 2026 15:48:16 -0400

I get why people are hesitant to abolish large parts of the government. I also get why, despite this, more and more people want to abolish the Immigration, Customs, and Enforcement (ICE) agency.

While ICE's recent psychopathic-clown-show tactics have put it under a particularly bright spotlight, ultimately I think people want to "abolish" it for the same reasons some people wanted to "abolish" various local police organizations in 2020. At some point, it starts to feel like the safeguards on positions of state power are entirely voluntary, and that the people with that state-granted power are the ones who get to decide whether to obey them or not. Those aren't really safeguards! For all the talk of rounding up people who "broke the law", regular-ass Dads like me have been watching videos of morons in tactical gear blatantly violating a wide variety of rules, laws, and even Constitutional rights with absolutely no consequences whatsoever, let alone appropriate ones.

For instance, I'm sure I have seen over a hundred videos in the last six months of ICE and CBP employees doing something that made me think "that guy should go to prison for that", or maybe even "I think you're supposed to go to prison for that", and none of those guys are going to go to prison for those things, or even lose their jobs. Personally, I don't think it's weird for someone, at a certain point, to just say "the hell with all of this" and demand a fundamental rewrite of this part of the social contract.

Immunity as a Given

Many policy debates are essentially an exercise in trying to make people accept certain "givens". One given that's been pushed forever is the idea that law enforcement, for the most part, needs to be in charge of regulating itself. If someone from the government with a gun does something that looks or feels illegal, it should basically be up to a bunch of people who have the same job to decide whether there should be any repercussions, and usually the answer is "no".

Now, you can make an argument for this. You can say a world where law enforcement is held accountable by some other function, and not allowed to be given vast immunity to a host of otherwise criminal actions, would be a world where laws could not be enforced, and everything would go to shit. You can say that if police, or ICE agents, or whomever is zip-tying you today could not operate with absolute confidence that if they get scared, it's okay for them to shoot whatever they are scared of, that there would functionally be no policing at all. You can argue that! However, I do not find it especially compelling.

What I think is much, much more likely is that most people have done some math in their head that goes something like this. If a policy makes the police 5% more effective at protecting you from things you don't like, but 5000% more likely to hurt, rob, or kill innocent people while they do so, that seems like a bad trade. BUT, if you think the 5000% increase in abuse will happen exclusively to people who you are not concerned about, that trade seems fine. I mean, it shouldn't really seem fine, morally, but I would guess that it probably does, in fact, seem pretty fine to a lot of people. But this is just run of the mill "leopards eating faces" stuff. The point isn't "no real-world accountability breeds bad outcomes for state power", even though that's also true. The point is "if you've removed all real-world accountability you can't fix bad outcomes by adjusting the particulars of accountability".

In this case, that's the whole "do we fix ICE or get rid of it?" argument, which is a good argument to have. From my perspective, though, it's also not a very complicated one. ICE — and unfortunately, most 21st century law enforcement — have insisted on building policy around the idea that law enforcement cannot be held accountable the way regular people are, and in fact need to be fundamentally immune to almost all of the consequences a normal person would face for doing various violent or grossly illegal things to another normal person. That's non-negotiable, apparently. And now, with that principle in place, let's make some rules!

See why this is a waste of time? There are already lots of rules! They're simply being ignored because they can be ignored, and the only answer we can come up with are more rules that will also be ignored, because underneath it all too many of us still think law enforcement should get to decide if it did something bad or not.

In my heart of hearts, I think this is what animates people who want to abolish various law enforcement functions. I don't actually think — in most cases — it's some hippy-dippy belief that crime doesn't exist (although it really would help if the police solved more crimes) or that there is no need for law enforcement of any sort. Instead, it's a rejection of the idea that these organizations should exist as so many of them do — self-regulated, armed, well-funded, unionized, highly political groups that receive massive judicial and legislative deference in almost every scenario.

I think a world where turning off your legally-required body camera, for instance, and then arresting someone, was potentially a form of criminal negligence is absolutely unthinkable to a lot of people. But I think that position understates the seriousness of the task given to armed agents of the state. I didn't invent it, but I think the idea of "higher standards + real accountability + much higher salaries" isn't crazy even though it's not a panacea and the devil's in the details. Law enforcement is hard, but so is nuclear physics — and we don't let nuclear power plants self-regulate or operate with the knowledge that everyone working there will be immune from almost any criminal charge if they decide to kill a bunch of people.

And those are real cops! ICE makes the disconnect here even more obvious. What utility are we even getting out of these goons? I'm not going to stand around and listen to a theoretical argument about utility ICE might have if the people who work for it did their job in a completely different manner than the way — given carte blanche to do whatever they want and total deference from local authorities — they choose to actually do it. I'm going to take it as it is. They don't follow rules. They lie constantly. They willfully commit sociopathic violence with no consequences. Logically, how would you even fix that? Find some magic politician who will be our benevolent dictator and use his unaccountable army thoughtfully?

We had versions of that for a long time. No, not an actually benevolent ICE (imagine that, lol), but one that put at least some limits on itself because the idea of just telling the public, in every... single... interaction, to eat shit and die seemed... unseemly. But it was only a matter of time before thugs and goons would be drawn to the warm flame of unaccountable, masked violence and bullying, and now ICE simply is what it is — a relationship defined by its lack of boundaries, which means we can't fix it with boundaries. It just has to go, and then we try again with something completely different.

Resolution 2026: Like The Phoenix Except It's Still Currently in The Ashes

Mon, 22 Dec 2025 15:15:10 -0400

It's been a while, hasn't it? Well, not much has changed. Resolution remains stable, functional, and operated by a non-business that loses an extremely small amount of money every month. For anyone poking at Resolution in 2026, go nuts! Everything still works, and will continue to work unless... I dunno, something important breaks? The internet ends? At any rate, Stripe handles payments and they're not going anywhere either (I don't have or want your credit card information), so this thing pretty much runs itself at this point.

That being said, as I hunker down for a long, unprofitable future of running this thing for no reason other than ego, pride, and a stubborn sense that I'm still right and everyone else is still wrong, I've taken a few cost-reduction maneuvers.

All my awesome walkthroughs have been deactivated. This is a huge bummer because they're all really good and hilarious (says me!), and run by a great service called Product Fruits. Unfortunately, it was costing me $100 a month which is, by far, the most expensive part of Resolution (lol). So now you'll see the still very functional Model Index where you used to see the Examples page.

I canceled Sentry. Sentry is enormous and doesn't need my endorsement, but it worked really well, especially when we were mucking with things. Not so much mucking anymore, and I save thirty bucks a month.

That's basically it! All I really do now is pay Fly.io like, 20 bucks a month and a little bit for web hosting. We're good. Until this thing becomes too popular for basic infrastructure, everything should be solid for your model-making needs. And so far, obscurity is something Resolution has been able to count on!

Is there a future, here?

There's always a future, friends! Seriously, though, I am a non-developer trying to build software, which means I need a lot of money or to become way, way smarter than I am. If I'm being honest, neither of those seem even remotely likely anytime soon. I think about Resolution all the time — and not fantasies of it being popular or anything, but actual use cases, improvements, etc. — but some ideas just have very high bars for minimum viable product and I clearly don't have the resources/skills/wherewithal to brute force that.

Software is in a weird place anyways, as not just the investment zeitgeist but even user culture has really moved away from tinkering and exploring and into basically barking demands at various devices and expecting an answer, which is exactly the opposite of not only how Resolution works, but how it's supposed to work even it's sexiest, theoretically VC-fueled form. So as a technology innovator, I may just be one of those guys my Dad always referred to as "rubber roads, cement tires".

I am very interested in open-sourcing Resolution. Like, very interested. But I don't really know how to do that right, so it's not going to happen on its own. If anyone is good at that / aware of the potential pitfalls, please reach out. Maybe there's a future here after all, even if it doesn't involve me looking down disdainfully at everyone from a private jet with my face on the tail.

Actually, Hacks are Bad

Fri, 12 Dec 2025 12:58:45 -0400

If I may — a "hack" is not a good thing. At their best, hacks are clever, temporary exploits that get you where you need for the time being, or if you're a criminal, a way to bypass security that (by definition) you aren't supposed to be bypassing. Most hacks are just crappy, lazy, unrealistic implementations that obscure cost, sometimes deferring it but also usually increasing it in the process. The worst ones are literally scams.

Don't aspire to come up with hacks. There are way too many hacks already. Aspire to come up with real, thoughtful solutions, and advocate for the time and resources to execute them.

Rage as a Service

Wed, 03 Dec 2025 11:18:37 -0400

Trolling people is easier than being funny or clever. This is not a new challenge, but here we are, once again pretending that failing at it is a tactic and not a weakness.

“Some advertising and marketing agencies are now intentionally leaning into the volatility of the current political climate, not to take a stand but to manufacture outrage,” said Mikah Sellers, an advertising consultant who has worked with major brands including Booz Allen Hamilton and Carfax. Companies are tapping into cultural rifts and driving wedges in hopes of capitalizing on the strife, he said.

How will they capitalize on pissing people off? Unclear! In fact, here are the companies (sometimes a generous classification) referenced in this article that are allegedly getting exactly what they want from this tactic:

Friend
Nucleus Genomics
Skims (Kim Kardashian's clothing brand)
Sabrina Carpenter
Pippa
Cluely
Clad Labs
Artisan

Leave the pop musician and the reality star aside, because I understand the commercial viability of trolling in those industries. But the rest? These companies are not successful. They can scream all they’d like about how they’re getting what they want as they slowly (or quickly) go out of business, but this largely startup-fueled delusion that life is either TikTok or the Trump administration, and you basically need attract eyeballs at any cost and then go from there is not actually backed up by the facts or financials.

And the thing is, the smart counter to bland, play-it-safe branding isn’t stupid, insecure edge-lording. It’s staring you right in the face — it’s CostCo, dammit! If you want to be edgy, get your name in a story like this, which has spread around the internet organically so much on its own that it has its own Snopes article confirming its authenticity:

"I came to (Jim Sinegal) once and I said, 'Jim, we can't sell this hot dog for a buck fifty. We are losing our rear ends.' And he said, 'If you raise the effing hot dog, I will kill you. Figure it out."

Just an incredible quote. No notes. This is the kind of shit people want. That they feel. It's not generation or culture-coded, other than the fact that people are constantly being screwed by companies acting in their rational, best financial interests at our expense, and here's a guy running a company who is just MAD about it, stomping on everyone's least favorite title ("CEO") and even threatening (tongue-in-cheek) violence over it!

None of this is new. How about this Dollar Shave Club launch ad, from over a decade ago?

It's the same thing. It works because (1) it's violently pro-customer, and (2) it's about what the company actually does to/for those customers. The edgy tone is fine, but the cause of that edginess feels more like genuine excitement about what they're able to do for customers, and anger at the worst, most anti-customer aspects of their competitors.

When everyone was watching this ad and talking about how they needed one just like it, we didn't have to figure out what percentage of them were hate-watching it, because it was zero. In fact, when everyone tried to do this, the problem they ran into was (a) they weren't actually this passionate about their business or, more specifically, their differentiator, and (b) they're not fun, creative, or funny!

Conversely, this latest run of pathetically click baiting people into looking at you for a second, rolling their eyes, and then, as they walk away, shouting "Ha! You're in the funnel now!" completely misses the point. It fees like it comes from a generation of attention-grabbers who have spent too much of their lives on phones, in feeds, and quantifying every aspect of their social experiences. And while generational preferences adjust (I'm sure much of their audience is afflicted by this same problem), we're not talking about music and language choices here. We're talking about whether people want to feel happy or angry, like a great new day is dawning or the dumbest, most obviously wrong person in the world just slid into their DMs.

Nobody wants that. My kids don't want to feel that way, and neither do their friends. When they do feel that way, sure, it's hard to escape. But they hate it, and banking on people who hate you and what you represent to become customers (let alone repeat customers) is insane.

Accountablli-Buddy

Thu, 20 Nov 2025 00:07:56 -0400

My Theory of Productivity

Allow me a theory. I probably didn't invent this, but if I did, bully for me.

Work output, when increased beyond the amount of available accountability, without a matching increase the available accountability, will never generate a lasting increase in productivity.

Here's what I mean by all these terms. Work output is the amount of stuff you make or things you get done. Maybe you make toys, maybe you insure businesses against floods, maybe you send emails. Work output is necessary but not sufficient to generate productivity, which is often why doing actual, productive work is challenging. If all you needed was raw work output, you could just jam out whatever all day as quickly and easily as possible and solve lots of problems. Nothing works this way.

This is why we have accountability. Accountability, in my parlance, is sort of a backstop against work output. It doesn't necessarily guarantee that all work output is good (that would be "micromanagement", which is a great way to drive work output to zero), but it ensures that for every kind of bad output, there is time, energy, and brainpower available to figure out why that's happening and take on the responsibility of preventing it. In other words, mistakes are okay, but just making the same ones over and over again at similar (or increasing) rates is not.

Productivity is when these two things align. If work output goes up, and a person, system, or process is available to make sure that work output is positive (or at least not negative), you will almost always see a commensurate improvement in productivity. I define that as whatever positive outcome your organization is trying to accomplish (usually whatever gets us paid — the insuring, the toys, the emails, etc.)

Accountability as a Limiting Factor

As we are frequently reminded by people trying to get us to invest in ~~insane~~ exciting things, the world has gone through many productivity revolutions thanks to various technological innovations. While some of things improved the quality of things, or the safety of the people making them, the most obvious impact of the biggest ones is a large, comparatively inexpensive increase in work output. My new factory can make a thousand pairs of pants in the time it used to make a hundred, resulting in both cheaper pants and higher margins for me. Everyone wins. My new corn can grow on land that used to be barren, and using water from far away brought in by pumps that didn't exist before. More corn, less useless land, everyone wins, at least until I start growing fake, inedible corn to take advantage of massive agricultural subsidies.

I am a huge fan of these developments in general, and always have been, even though I am not an industrialist but merely a simple 21st century office drone. I am constantly seeking ways for technology to improve my work output, because when I succeed at this, I usually receive praise (and occasionally promotions!) for actually doing less work. It's fantastic, and if you'll allow me, just very American in the best way.

(music swells)

But there's a catch. I mean, it's not really a catch so much as a limiting factor. My technological innovation can't increase my work output beyond my ability to make sure my work output isn't actively harmful. Have you ever sent out an automated email to a large customer base that said "Hi, {FIRST NAME}"? Obviously I haven't, I am totally asking for a friend. But that's an example of the risk of increasing work output beyond accountability bandwidth.

Now, in the case of the embarrassing auto-email, we make that tradeoff 10 times out of 10, but there's still accountability. Just ask... my friend! When you send that stupid email, you're going to hear about it. Recipients will respond and yell at you, co-workers will forward angry customer replies, and eventually you're going to hear about it from your boss. If they are a bad boss, they will tell you this is unacceptable and maybe call you an idiot and then walk away and start working on your Performance Improvement Plan so they can fire you. If they are a good boss, they will help you figure out some way to audit the "Name" information in the CRM, or use "no data fallback" feature in your email designer. But either way, these emails will not just blast out with FIRST NAME on them forever. And that, my friends... is accountability.

Innovations that increase work output must, by the rules of my theory, be paired with innovations in accountability, or else that automation will not generate productivity.

By and large, this is exactly what has happened with most work output-increasing technological innovations, otherwise they would never have stuck around. Various technologies have improved our ability to review things, reduce random errors, and more quickly and easily work with various problem solving experts in the event that something goes wrong. These are good things, even though they are less sexy than, you know, the cotton gin or the assembly line or whatever. Hell, unions are an accountability innovation in a lot of ways; an organizational check on the staggering increase in work output (and some of the resulting bad effects) resulting from the Industrial Revolution.

First Salads, Then Robots

Okay, so as legally required by Internet Rules of 2025, let's now apply this to artificial intelligence, or more accurately, large language models, image generators, and maybe (if you squint) "agents". There is a funny little dance going on when we talk about these things, because we can't quite decide if they are supposed to replace us, or be used by us. In general, I find that the conversation — whether about society in general or in a sales pitch for some AI tool — tends to start with replacing, only to then inevitably downshift to "it's a just a tool/massive force multiplier/etc." as details and reality begin to weigh down the conversation. The tech industry has been able to dodge a lot of difficult logical questions by flipping this bit back and forth as it suits them.

"Layoffs in the streets, force multiplier in the sheets", if you will.

But here's the thing — it actually doesn't matter because accountability is the limiting factor in either case. Think of it this way. You'd never hire someone with zero accountability. Maybe their accountability is generous, or forgiving (maybe they're a cousin, I don't know, I'm from Rhode Island), but unless you're talking about a legitimate charity case, there's gotta be some. Even something as simple as saying "if you screw up badly enough, you'll get fired and then the paychecks will stop" (again, optional in Rhode Island) is a form of accountability, however crude.

So there's at least an element of accountability in every function, or it's simply not a productive job, because if there's no accountability, you're effectively saying the output doesn't matter. And that means the accountability bandwidth thing comes into play with every function as well. Somebody was responsible for every caesar salad I made in the summer of 2001 at 22 Bowen's Bar & Grill. Mostly it was me, but it was also my boss. That doesn't mean I couldn't make a mistake on any given salad (oh Lord did I make those), just that you could take any one of those mistakes and say "who is dealing with this by either fixing the cause of this or leaving the organization?" and there'd be an answer every single time. But the system we had in place was predicated on three college kids making every salad to order, by hand. There were only so many we could make, and thus there was a hard cap on both our possible work output and the accountability needed to ensure the value/utility of our output. In short, three college kids who didn't want to get yelled at or fired in the middle of the summer, plus a full time assistant chef who really didn't want to get fired, together, could handle the task.

If for some reason the restaurant exploded in popularity and we needed ten guys making salads at once like a Chopt in Midtown, or if the three of us got magic AI salad machines that let us spit out hundreds or thousands of salads a minute, this system would need to evolve for us to use it. Either those machines would need iron-clad safeguards in them (making them effectively error-proof), or you'd need a massive investment in quality control to hold yourself accountable for making good, edible salads. You wouldn't just 10x the process and say "look how productive we're being" without anything in place to make sure people weren't just getting dirty bowls hastily filled with handfuls of chick peas.

Okay, Now Robots

The fundamental business promise of generative AI has a giant, accountability sized hole in it. So far, many vendors have dodged this by making accountability sound like ethics, which many companies will discard for a big enough ROI, but this is a major misread of how business works. Accountability can be about ethics, but it's really just about outcomes, and there is no reason to think that businesses are willing to throw away their control over outcomes because generating a lot of arbitrary, uncontrolled outcomes now requires little to no human effort.

Bluntly, if you're selling a massive increase in work output without some way to also massively increase accountability bandwidth, you're essentially proposing one (or maybe more) of four possibilities:

1. Workers have plenty of unused accountability bandwidth now, so a huge increase in work output is actually great

This doesn't sound like 2025 to me. Companies have been finding new and more creative ways to avoid being held accountable for things for decades now, with "innovations" ranging from binding arbitration clauses, to liability shield laws, to shutting down support lines and dumping people into user forums. The accountability that remains is almost entirely related to raw financial performance. Companies have been talking about "doing more with less" for years now; I find it hard to believe people are sitting around checking their work twice for lack of anything else to do.

2. It's worth it for businesses to pay increase accountability bandwidth to meet the huge increase in cheap work output

Is it, though? Every marketing department has to figure out things like "the right number of campaigns to run" precisely because it's often not worth the cost of installing sufficient accountability. It wouldn't be worth the cost of doing thousands of additional hours in post-mortems and data analysis just because you could now afford to spin up those campaigns for zero dollars. Then again if we're not 100x-ing our output here, what's the value of this innovation? What I could really use is one automated campaign manager who was just as accountable as my human ones...

3. Accountability bandwidth can be increased with the same types of technologies that increase work output

... but that is not a thing, because computers are not accountable. They don't care. They don't need to eat. They don't need to make their parents proud. They don't need anything, because they're not alive, and being alive is a non-negotiable part of giving a shit about anything. You can program rules into software, but rules are not the same thing as giving a shit, which you will immediately realize if you ever have to work with someone who doesn't give a shit about work, but is sufficiently capable of following rules. In some ways that kind of person is just a slow computer, but more importantly, every computer is just a really, really fast version of that annoying employee. There are lots of ways to get different kinds of people to give a shit about different kinds of things (this process is called "middle management", ask ChatGPT about it), but there zero ways to make computers give a shit about anything. In fact, one of the reasons software can work/write/execute a decision tree so quickly is that it doesn't give a shit about literally anything, so nothing slows it down.

4. Accountability is irrelevant if you scale work output enough, or it's just irrelevant in general

Lastly, despite it being a running joke for — I dunno — a hundred years or so, there's an increasingly weird, inexplicable interest in the "a thousand monkeys on a thousand typewriters will eventually write the greatest novel ever" approach to work. Maybe it's because some of the world's most successful high margin businesses are automated, algorithmic trash dispensers with seemingly no limit to how big they can scale. Maybe it's because we've over-financialized basically everything at this point, and we can't conceive of any system where "N" has some sort of fundamental limit. Maybe it's something else! But I'm here to tell you that you can't scale any work output to the point where nothing matters. Facebook is certainly going to try, but for the rest of us, there are only so many places to show your infinite, dynamic ad variations. So even if the numbers are large, they are still numbers, and they still require some form of boring old accountability for results.

Good Automation is Still Good, Bad Automation is Still Bad

Automation is an incredibly valuable thing, but one of the many downsides of the blind rush to automate anything we can find is that some of the most important skills in making automation decisions seem to be atrophying as we race to lower the marginal cost of arbitrary work output. For instance, my little event management project automates the gathering and tracking of events and their related deadlines. You just give it a website, and it goes and finds all the events, all the deadlines, and organizes everything. I hate doing this, it takes me forever, and I make a lot of mistakes, so in general I like this painless increase in work output.

But there's obviously an accountability issue here as well that I don't want to ignore. No one is going to want my application to automatically grab tons of irrelevant events and deadlines and shove them into the system. They won't even want me to automatically grab events and deadlines that are sort of relevant. They want the right ones and only the right ones and since events are not labeled on the internet as "ones you should care about", there is no ironclad, computer-powered way to do this with 100% certainty, which pushes accountability to my user. So I actually throttle the process by (a) separating the process of finding events from finding deadlines, and (b) making you confirm which ones you want in each process. I could increase the number of events and deadlines you find, and reduce the time and effort it takes to do so (wheeee, work output!), but that would be dumb and counter-productive because it would ignore how difficult that makes the unavoidable challenge of making sure those things are correct and useful.

This is a really simple, small example, and it's not something I'm doing because I'm some product genius or especially sensitive to user needs (history would indicate that I am quite bad at this, actually). I'm doing it because I actually care about the true productivity of using this application, because when I originally needed it, I was held accountable for effective, intelligent event management and having good, accurate answers to logistical questions. No one cared how long my little tracker spreadsheet was, or how many columns it had, or whether I knew the load-in dates for events we shouldn't be going to.

The problem 99% of generative AI uses cases I see have is that they don't really care about true, accountability-supported productivity and outcomes, primarily because they don't have an answer to the accountability bandwidth problem they themselves are creating, and their business models and cap tables dictate they make a 1000% impact, not a 50% impact, so being held back by the bandwidth is simply unacceptable.

But that's a vendor/product/business model problem, not the market's. If you're trying to sell these things as solutions to actual, functioning organizations who care about outcomes, or ideally, thinking though how to build them before you do that, I'd keep that top of mind.

Sure, Jan

Fri, 03 Oct 2025 11:32:08 -0400

The story of 2025 continues to be — never concede anything. Just stare ahead as you plow into the merge and the other guy will yield.

In that spirit, here's Sam Altman, turning up the music and accelerating as he rapidly approaches the oncoming produce truck of reality.

As if this wasn't hand-wavy enough, keep in mind I'm reading this the day after OpenAI launched, with great fanfare, Sora 2 — "deepfake TikTok", if you will — which is literally just a slop machine for making fake AI videos of "your friends", which actually means "people you want to see in fake videos".

This company is the mullet of technology. Business in the front, party in the back. Scientific discovery in the streets, ShitTok in the sheets. Whichever one of those things gives them enough money to survive (the Department of Defense, or advertisers) first will be what they claim is what they wanted to do all along.

And if, as more than a few people are starting to suspect, neither one happens? Well, it's... it's gonna get real ugly.

Incredulity

Thu, 11 Sep 2025 11:28:08 -0400

Every day, there are many things I don't do because I think they are fundamentally wrong. Some of those things might get me something I want, or closer to something I want, or away from something I don't want to do, but I find them wrong so I don't do them. This does not make me special, this just makes me a functional, civilized adult.

However, I don't see myself as some inherently perfect paragon of virtue. I really do try to operate outside of simple, transactional self-interest, but simple, transactional self-interest does affect me. For example, my very self-righteous, Protestant-work-ethic desire to be employed and financially productive has wavered in direct response to how badly I need money. I measure my words online and at the office in large part because I (reasonably) fear the short and long term consequences of saying whatever I think whenever I think it.

In other words, I do a lot of things the right way because I have morals, but there's a gray area where even I don't know if I do some things because they are right, or because they are safe. That's why, as a society, we try to make the right things safe, and the wrong things dangerous. It's moral hazard!

Steve Ballmer and Moral Hazard

Steve Ballmer bought the Los Angeles Clippers a few years ago because he has effectively an unlimited amount of money. Despite this, he can't just do whatever he wants with his team (like spend his infinite money to just sign all the best players), because he's part of an association that has rules and restrictions on that sort of thing. Ballmer is in trouble because through some excellent journalism, it's come to light that his star player Kawhi Leonard has been getting huge amounts of endorsement money from a weird, unprofitable startup owned by Ballmer and his Clippers ownership partner, for doing nothing. Effectively, this looks like money laundering to avoid the rules on how much teams can spend on their salaries, which is a pretty massive deal in the NBA.

Ballmer has denied everything and pleads ignorance on everything from his investment in this company to the particulars of how Leonard was compensated, but as more evidence is revealed each day, things are looking worse and worse for him and the team. Like, a lot worse.

When this story initially broke, one of the loudest forms of skepticism that I heard can basically be paraphrased as such — "Steve Ballmer is really smart, and this whole scheme seems incredibly stupid. While it's nominally money laundering, it's lazy, ham-fisted, and the idea that a kajillionaire business magnate who clearly loves owning and operating his basketball team would risk so much strains credulity."

On the one hand, this is a pretty reasonable take. But it's actually just a great reminder that culturally and morally, there is a huge disconnect between our expectations for how the world should/will work, and what's required to ensure that it does that. While there's this sort of baked-in assumption that these activities are risky for people like Ballmer, is that assumption actually valid? One of the first social science things I learned in college that really raised eyebrows was that while people spent a lot of time arguing about criminal punishments, the real driver for crime was whether people got caught at all. We focused on sentencing because it's easy -- those people have been found and convicted, so putting them in prison for any amount of time is trivially easy. One year, five years, a hundred years, whatever! However, actually catching people who commit crimes is much, much harder than you would think. It requires more than power and authority; it requires skill, resources, and lots of hard, boring work.

It's hard to catch — really catch — people doing bad things, which is why so many bad things have been discouraged with penalties like shame, embarrassment, and reputational damage that don't necessarily require a famous or powerful person to get truly, legally, undeniably caught. Historically, simply being associated with something like a corrupt, self-dealing cryptocurrency or shady real-estate scam has been harmful to people with big ambitions, regardless of whether it's been specifically proven that they did whatever bad thing that association implies. It's not "go to jail" harmful, and it never should be — the power of the state to take someone's freedom away is enormous, and dangerous. But one of the reasons people lost their minds over "cancel culture" is because the non-legal, indirect consequences of people believing you are bad are really potent, and people don't like when they have to pay them.

(As an aside, as with many social punishments, I don't have a fundamental problem with "cancelling" famous people from fame and media exposure. I just sometimes have a problem — as many/most people do — with when we do it and who we do it to. That's a boring answer, but I'm quite confident that it's the correct one. The idea that as a culture, we should continue to focus our attention on the same people even if they say or do awful things is obviously stupid. It has nothing to do with free speech, and everything to do with bad, unprincipled editorial choices.)

But here's the thing — just like we lack the physical resources to bring every criminal accusation to trial (and thus depend on a system of plea bargains just to keep the lights on), we lack the same resources to adjudicate every terrible thing that powerful people are capable of doing, so we depend on shame and yes, the threat of being "canceled" (it's just... such an eye-rolling term, my God) to keep the world working the way we expect it to. In a shameless world, though, the system starts to break, and it makes sense for people with a ton of resources to simply fold their arms, deny everything, and demand the system adjudicate everything to the full extent of whatever the law is, because the law alone is actually pretty easy to survive if you are rich and powerful.

So I don't know what Steve Ballmer did or didn't do in this case, but I do agree he's not stupid. However, given what a ruthless, smart, powerful person might see as his best option to move forward in 2025, I think Ballmer's savvy might be as much of a potential explanation for his guilt as his innocence, which is a bad sign for everyone.

Real-World Vibe Coding

Tue, 02 Sep 2025 15:17:45 -0400

It's been a couple years since I took my first look at generative AI and concluded that the most likely use case for this kind of technology, by far, was "better" spam. Since then, despite all the activity, investment, discussion, and model releases, nothing has really fundamentally changed my mind about that. While image generation is dramatically better, text generation is dramatically cheaper, and the tooling for all of it is simpler and more available, this stuff continues to be an inch deep and a mile wide. The strongest utopians and doomers share a tendency to see revolutionary changes to work they don't actually do themselves, or even understand, and much less impact to things that they have real working knowledge of or true responsibility for.

Charlie Warzel wrote a few days back about an idea that I've felt has been inevitable for a long time — what if this technology is basically mature?

"This is the language that the technology’s builders and backers have given us, which means that discussions that situate the technology in the future are being had on their terms. This is a mistake, and it is perhaps the reason so many people feel adrift. Lately, I’ve been preoccupied with a different question: What if generative AI isn’t God in the machine or vaporware? What if it’s just good enough, useful to many without being revolutionary? Right now, the models don’t think—they predict and arrange tokens of language to provide plausible responses to queries. There is little compelling evidence that they will evolve without some kind of quantum research leap. What if they never stop hallucinating and never develop the kind of creative ingenuity that powers actual human intelligence?"

I think this is exactly right, and I think it's been inevitable almost from day one given what this stuff fundamentally is underneath. Warzel then gets into the part that's probably way more important, which is the socio-emotional impact of this stuff being everywhere and baked into everything (the whole piece is very good), but I'm going to stick with answering a much simpler question — what's a potentially valuable use case from plausible looking, computer generated content with no guaranteed connection to reality?

The Test Data Robot

My latest half-baked idea involves LLM parsing of emails, and spitting them out as structured data. It's a potentially dubious concept at its core due to all of the apparent limitations of this technology described above, but it's one of those interesting "well, maybe it'll work?" concepts that you really have to try to understand. Unfortunately, since we can never really understand if a logical prompt "works" or not (because no matter how carefully we write it, our prompt is not programming — it's just natural language going into a black box, and then something comes out of the box), the best thing we can do is test the hell out of it. Give it tons and tons of emails, see what it spits out each time. You're unlikely to get to the root cause of those test outcomes (because again, there is no root cause), but you can get the success/failure rate and see if you're comfortable with it.

Now, while it often feels like I have an unlimited number of event emails in my inbox, this is not literally the case. I also don't feel like making them up for test purposes, certainly not with all of the fluff and structure that makes them look, feel, and function like real test data, and at the scale that I need them for testing. But you know what has plenty of time on its hands? Yeah you do.

Just Prompts (v1.0)

I started out the way most people probably do, by simply talking to Gemini and asking it to make me these sort of emails. The output was... kind of annoying, and didn't look or feel like ones I actually got at work. In the spirit of giving the LLM as much to work with as possible, I proceeded to feed it a bunch of actual emails from work, hoping that it would pick up some patterns. While this sounds like a good idea, there's a pretty big difference between being a machine learning engineer writing custom models, and shoving a bunch of stuff into a chatbot, and the results certainly bore that out.

While I got some initially promising results, there was a clear drop-off once I gave it around five emails where it started to ignore previous ones in the "training set" (I know, I know, this is not an actual "training set" of anything) and it became clear it was just aping whatever I gave it.

I started over, and this time, I didn't give it any training material at all. Instead I just said what I wanted, had it write examples, and corrected a few bad tendencies or examples of it ignoring my requirements. The emails are still obviously, almost painfully fake, but structurally they're fine (if a bit unrealistically repetitive) and I actually started testing our event, task, and date extraction with them.

The Infinite Garbage Machine (v2.0)

If you've tried any of the many productivity hacks floating around the internet these days, many of them involve working directly in ChatGPT or something similar. One fairly major annoyance, though, is the end state of whatever you make — the bot can't do very much, so you're often given something and told to copy and paste it somewhere else. So when I got tired of asking for ten HTML emails at a time, scrolling around to find the right one, pasting it into a text file, renaming the file with an .HTML extension, opening the file in a browser, copying the rendered HTML out, and pasting it into an email to send, I decided to try something slightly more sophisticated.

Behold.

This version does a couple of things that are legitimately useful for me:

It generates an entire event "object" (for lack of a better word") that I can then generate additional "deadlines" for.
It lets me make multiple emails that reference the same event.
It lets me make a deadline specific email.
It lets me assign dates and URLs to the event and its deadlines.
It lets me provide custom instructions for any given email (very helpful for testing).
Gives me a button to download the .HTML directly (which I then have to open, copy, and paste into an email, but still)

To be clear, these emails are still hot garbage. They are barely plausible, fairly repetitive, have the absolute bare minimum of design to them, and the little event fantasy world I'm asking it to maintain in the background often devolves into nonsense with deadlines occurring in implausible orders or having ridiculously short or long amounts of time between two given deadlines.

But... that's okay! I'm not sending these to anyone. They're just to test my application's ability to extract and structure information correctly, and while ultimately what matters is my ability to extract real information from real emails, this is a great combination of pretty easy and clearly better than nothing. So I am declaring success with this project, and labeling this as an actually useful implementation of vibe-coding that was totally worth the cost of... well, I got Gemini Pro included with the Workspace package I needed to buy in order to turn on the domain-wide authentication my experiment requires. So basically, the marginal cost was nothing, but... the utility was real!

Vibe-Coding Reality Check

It was certainly kind of funny to use completely black-box vibe coding to build a tool designed to help us build an application we were developing in a much more traditional manner (with Python and Bubble) at the same time. Progress on the "real" app was often painful, slow, and required thinking through what wasn't working and why. Progress on the Infinite Garbage Machine was sometimes incredibly fast, but totally unpredictable, and the results were almost always exciting at first, and then slightly disappointing once the reality of what had been delivered set in. And while the whole point (as far as I understand it) of vibe coding is to not have any idea how anything works, there are a few development concepts you should be aware of if you're going to try anything like this.

Version control. The default Gemini interface is pretty capable, even though as mentioned, it's sort of odd to run everything in the little "Canvas" widget. (I very lightly kicked the tires on Google's "Opal", which is apparently intended specifically for this sort of application development, but it didn't do a very good job of interpreting my requirements and I gave up.) But one enormous problem I ran into was the lack of an easy way to go back to prior versions of your application. This is especially important because you really have no idea how any request you make will be interpreted, what it will do, or whether it will completely wreck what you have. I didn't find an easy, obvious, reliable way to "undo", which made me very hesitant to change things if they were working at all.

Things fall apart. In a related vein, my vibe-coding experiences faced a bit of a paradox where iteration was clearly the only way to get what you really wanted, but that the more you iterated, the more the system started to lose sight of other, older, but no less critical requirements. That's not really iterating, then, is it? It got bad enough that even though there are obvious ways I'd like to improve the Infinite Garbage Machine, I feel like it's reached the optimal point of maturity and that the risks of asking for refinement outweigh the benefits.

It's not very good software. My application barely does anything and it still feels like it's stuck in the mud. The interface is crappy and very brute-force reliant, the whole thing is ugly, and whatever it's doing with Gemini in the background to generate things is a lot slower than doing it directly in the app. In theory, I could try to refine these things, but I guess my application is complicated enough that when I started trying to do that, it began to generate worse, more repetitive emails. It's fine as is, given what I'm going for, but I do think if you expect people to use your vibe-coded tools (I certainly don't, this garbage is for ME and me alone), you may be surprised by how frustrating and generally poor the end-user experience is, and I don't know if bragging that you don't even know how to code will make that any easier for your audience to handle.

In conclusion...

Like "AI", "vibe-coding" means way too many things and is too often discussed by people who don't know enough about the source material, and it's hard to have a real discussion about a vague topic with slippery definitions. That being said, I certainly found "non-deterministic, natural language application generation" to be useful in the fairly narrow, but non-trivial niche of generating simulated test content that met a bunch of relatively simple but important requirements.

So basically:

would it help to have a computer do something?
is the accuracy & precision of the "something" not really the point?
is the user experience basically just "put stuff in, different stuff come out"
is there some prior arrangement that makes this cost-effective for you (i.e., you already have access to a decent LLM)?

... if so, you should give it a try, at least before the bubble bursts and the price of doing all of this explodes.

Uneventful

Fri, 22 Aug 2025 13:20:14 -0400

For the last year, I've had to do a bunch of event logistics for work, and... I really did not enjoy doing this work. It's not a huge deal or anything (I wasn't exactly working in a bauxite mine), and it really was the most useful thing I could have been doing in my function, so I did it. That's startup land. But the work is a combination of uninteresting, repetitive, bespoke, and relatively easy to screw up in impactful ways that make it not really great for anyone, but especially challenging for me.

As I worked on this stuff, the most frustrating thing was that I didn't really seem to be getting that much better or more efficient at it, mostly because it's just not that kind of work. Unlike production processes where there are creative and technical workflows that can be improved and a level of quality you can aim to surpass with each project (even if you don't have to), event logistics are often about just not forgetting some stupid little thing you have to do, or making some small resource allocation decision that no one probably cares about but maybe someone really cares about.

To make this even worse, one thing about me that I usually keep close to the vest at work is that I absolutely loathe letting people down. It's a huge source of stress for me, particularly when I find the work I'm doing itself to be uninteresting, and the main thing driving me forward is just the intrinsic need to be a good teammate and keep other people from getting blocked. And when it comes to third-party event attendance or exhibiting, the pain you -- or your colleague who's sitting in some convention center in the middle of nowhere -- feel when things don't go right is a lot greater than the joy you feel when things go okay.

Despite all of this, events were not going away, because in the space we were in events are how you talk to buyers. It's just that simple. While the direct, dollar-in/dollar-out justification of any given event remains incredibly hard to track (as with anything that isn't PPC, it seems), the long arc of lead-generation, deal-closing, and account renewing really did seem to validate the effort and cost of going to a lot of these events. So I decided to, in my spare time, start thinking about what (if anything) would make this work easier, since no one was coming to take it off my plate anytime soon.

The Problems

System of Record

As with a lot of information entry and retrieval jobs, one of the obvious sources of stress I had was no single, central workspace to wrap my arms around. I had a huge email inbox full of mostly junk, but also a bunch of really important stuff, a couple clumsy Google sheets of dubious reliability, and the information discovery nightmare known as Slack. We weren't doing tons of tons of events -- a busy month maybe had two, and whole months would go by where we didn't have any -- but many of them would have anywhere from five to twenty individual tasks with their own deadlines that had to get done over the course of several weeks or maybe months. So there were these sort of streams of activity that went on for months with long stretches of inactivity for any given event, but really no break from always needing to have a firm grip on what was going on with events in general. Tasks tended to sit around, too, because they often required some vendor to respond to a question or blocker, or an internal (non-me) person to make a decision or commitment that they'd refuse to make a decision on for weeks or longer. Normal stuff, but when you add it up it's just incredibly easy to lose track of some dumb thing and end up paying a late fee for renting a power strip or whatever.

Now, where I've been doing this work, we have basically no central project management of any sort besides people's random spreadsheets, which didn't help matters. I ended up building out my own system using Airtable, which definitely helped, but Airtable had a lot of extra cruft and didn't let me do exactly what I wanted to. It was really hard to make certain bits of information stand out, or feel like I was showing things in the context I wanted to. It felt like I was putting in enough work to design the custom front-end of an application without the actual benefits of having a custom application. I'm a little bit of a nut about this stuff, but then again that's the only reason I was willing to put in the effort to build something with Airtable, so if it's not working for me I'm not sure it's really working for anyone.

Extraction

My Airtable task list held up okay when things came to me in the form of URLs, usually from coworkers in Slack. It wasn't great, but at least it gave me an anchor to put in my task list ("see if we want to go to _____") so I didn't forget about it.

Unfortunately, most things came via emails that contained more than one thing to do, more than one URL, or maybe no sufficiently comprehensive URL at all. In other words, I basically need the email, or I need to transfer a bunch of information from the email into a bunch of different fields in my system of record. This is... well, it's really boring work for starters, and it's also easy to forget to do, or to screw up. This is especially true as stuff changes, and suddenly I'm rooting around for an email from a month ago that I think I got but can't seem to find.

Basically, I want the process of extracting useful information from emails and putting that information in a permanently relevant, highly structured place to be as effortless as possible.

Event-Adjacent Information

Customizing the crap out of an Airtable instance gives you ability to literally map almost any kind of relationship -- this is why I like Airtable -- but I had to admit that it all felt a little cold and removed from my actual, real world of work. With events, I basically have to keep track of three types things:

the event itself (sponsorship, registration, rules, submissions, scheduling)
any people involved (their availability, their status, anything they need to do)
any of our related physical assets (signage, laptops, booth material, collateral, swag)

Then, of course, I have to keep track of the money attached to any of those things. And this is all just to know what we're putting into this!

I haven't even started talking about measuring or assessing outcomes, which is a whole different conversation between you, me, and your CRM. But even then, I'm going to need to get back to this information. So the point is that we're talking about a lot of funny little categories of things that have really specific relationships to the events. There are a bunch of dedicated micro-workflows and views I want of this stuff so I can decide what our options for a 10x10 booth are, or whether it makes sense to ship a bunch of stuff to Florida.

Is this actually a technology problem? And if so, does anyone want to solve it?

This is a question I ask myself all the time, mostly because I already did the "I have this problem, and I built something to solve it" thing with Resolution, only to find out that what I had done was (a) solve my problem, and (b) make something that would solve a problem I have with other people if they used my product, which they probably won't.

As I did this work from 9 to 5 every day over the weeks and months, it didn't get any more interesting, but I started to have more and more conviction in what the fundamental jobs-to-be-done were, or more accurately, the job-to-be-done. Bluntly, that job is automated, comprehensive data extraction, assuming extraction includes both pulling data out and sticking it somewhere permanently actionable (my definition does include both of these, but I'm not a computer scientist so apologies to any of them reading this if I stepped on a reserved word there). That's it. And since I was extracting natural language, and we have all these fancy, highly-subsidized large language models out there, I figured I'd give it a try.

The other thing I learned from Resolution is that while this breaks my heart, it's just really hard to go to market with a general purpose business product. It's not impossible, but I'm not very good at it and I don't really want to spend any money on this, so if this is going to do any good for anyone else, the best thing I could do was focus on a niche. In this case, I'm okay with that because I actually believe that while a VC-targeted macro-solution ("automatic extraction and data structuring FOR ANYTHING") sounds sexy, like most things the utility here is heavily dependent on nailing the last mile, which is turning your structured data into really useful, workflow-specific interfaces for people to actually click on. So while I'm not really an events guy by choice, I decided to keep the focus there instead of trying to generalize the problem into something I had to explain.

How Uneventful Works

Uneventful is a basic, browser-based CRUD application I built with Bubble. You can do a bunch of normal things in there, like add/create/edit your upcoming events, add deadlines and expenses to any event, manage sponsorship options, or assign people to go. This is the system of record part. There is nothing particularly special about it other than that it's built specifically to stay on top of managing a bunch of third party events for your organization.
In the background, Uneventful is connected to an email inbox. If you send it an email, Uneventful will use an LLM (and a bunch of custom code, more on this in a second) to pull out any events or event related deadlines, structure them, and add them to your account.

Basically, you can shovel all your annoying transactional emails to Uneventful, and you'll end up with a list of places you need to be and things you need to do, organized by when they have to be done. The system also grabs things like associated URLs and basic descriptions so it's a little easier to do whatever you need to do, and even grabs a copy of the email that you can reference to double check any deadline or event in your list. I basically copied this idea from Rippling, except they do it with expenses, and it was an absolute life-saver for me.

For now, that's it. As Uneventful stands right this second, it's already a big improvement for me, but there are a number of useful things I'd like to expand on that aren't outside the realm of technical possibility, even for our crack team of "one burned out product marketing guy" and "a retired electrical engineer". These include:

a web scraper where you throw a URL at it, and Uneventful grabs the event and a bunch of related information about the event.
event discovery based on what you do and what events have worked for you
"reporting" (eww, lame), but actually good -- this is an example of where this is pointless if you just do standard stuff but could be awesome if you really get biz-dev events
some way to manage contacts and interactions at a given event; maybe it's just raw numbers because I don't foresee this little guy becoming a CRM, but you never know.
related but different -- some sense of goals and goal management. Since numbers weren't always a good indicator of value, we'd often try to set up specific goals for an event ("talk to the assistant secretary of ____") because it was actually easier to quantify revenue impact that way.

"DOES IT AI?" (sigh)

Uneventful does use an LLM in the form of the Google Gemini API. When I first started trying to do this as simply as possible, I rigged Airtable's new-ish "AI features" to go and grab me descriptions from events I gave it, and it sort of worked. But that was just spitting out a text description for a human to read -- it couldn't really "break" or "fail".

Uneventful is much more ambitious, and our original plan was to use Gemini to both (a) extract relevant objects from an email, and (b) determine whether those objects were new, existing, or existing and sufficiently different to be updated. As it turns out, Gemini is pretty damn good at the first thing, and maddeningly inconsistent but generally pretty bad at the second thing, even in really simple scenarios where we were using structured schema output from our extraction sequence, and then basically asking Gemini to simply compare two (very, very simple) JSON files. Maybe we're stupid, but despite trying this over and over again, tweaking prompts, and doing as much debugging as a black box LLM will let you do ("please explain your justification for each conclusion you make and put it in this field"), we just couldn't get this to work consistently. My Dad -- my go to technical resource for all my random projects -- is both less cynical about AI than I am (mostly because he's 75 and doesn't give a shit about the tech industry one way or the other) and much more comfortable than I am gritting his teeth and solving problems with brute force Python. He went from being pretty enamored with Gemini to borderline disgusted by this failing as it became apparent that we just couldn't rely on it to perform comparisons. However, it works really nicely for extraction and now that we've built out our own comparison logic everything is cheaper and more efficient, so it's probably for the best.

The front-end of this is all Bubble, which I really think more people should play with. As discussed ad-nauseam here, I am both very much not a real developer AND someone who has taken some computer science classes and written a decent amount of terrible code across BASIC, Pascal, Java, Python, and weird stuff like ActionScript. I can look over my Dad's shoulder and help him figure out what a loop is doing, but I'll be damned if I can actually make what I want with code. It's just too hard for me. If you're stubborn enough to code and build out data structures, but suffer from the same sort of code-blindness that I do, Bubble is weirdly perfect. You get to wire things up, define objects, build logic and workflows, and even make API calls, but it's all through configuration panels and settings. There's a real learning curve, to be certain -- this is my second major Bubble effort and I did a bunch of small, broken experiments before I got to those -- but I really think it's worth it. You can make cool stuff, and do many of the fun internet web/app things everyone is talking about. I could never build something like Resolution with Bubble, as it's impossible to make truly unique, custom UI objects with this approach, but most applications aren't like that and you get a surprising amount of flexibility.

Want to try it?

Now that it works, I'm interested in getting other people responsible for this sort of work to try it out in a controlled environment (i.e., no more than like, ten of you, and all people comfortable enough to let me fix things, rescue lost data, etc.) to see if this is really useful, or even if it's close enough to being really useful that I should put more time into it. If that describes you, let me know at hello@resolution.biz and I'll get you set up!

Competence Theater

Mon, 07 Jul 2025 15:14:00 -0400

I have worked at many places. Without exception, the biggest challenge every one of them faced during my time there was either:

not enough people wanted what we were selling, or didn't want it badly enough
collectively, we continually did stupid things, or did good/neutral things in stupid ways

That's it. When we addressed these things, we did better. When we didn't, we did worse. Heck, even my own company was like this! I continually refused to address the first problem, and as a result, my company was not (and continues to not be, to this day!) very successful.

Thing number one really is an important problem, but to be fair, it's also hard to solve. You have to know what to make (anyone saying "JUST LISTEN TO THE CUSTOMER" can log off right now and go back to LinkedIn, thank you very much), be able to make it, and be willing to make it. Man, I get tired just writing that and thinking about it. Thing number two — doing stupid things, or doing non-stupid things poorly, or in a stupid way — isn't as existential or exciting, but it's usually more solvable, and boy is it absolutely everywhere.

My hilarious, fulfilled, and generally very successful Dad has given me various bits of advice over the years, but none better or more applicable to everyday life than my favorite:

"Don't be an idiot".

It's really an amazing philosophy, and I've put a lot of effort into living it every day, even in the face of investors, coworkers, managers, customers, vendors, and countless others almost constantly pressuring me to, in fact, be an idiot in some way. It doesn't always make me the easiest person in the world to work with, but in the end my dogged insistence on not being an idiot has done wonders for me and many — if not all! — of the companies I've worked for.

Despite this, "don't be an idiot" has not caught on with the business community. Maybe it's not sexy enough. Maybe it sounds too harsh (although I thought it was cool to be harsh again, I dunno). Maybe, just maybe, high-visibility business ventures increasingly require key stakeholders to act like idiots more than we'd like to admit. But either way, "stop doing important things in stupid ways" just doesn't seem to be a rallying cry employers are comfortable building their workplace cultures around. Instead...

For whatever reason, we keep coming back to this fantasy that if people work EXTREMELY HARD (not just "hard", but "so hard that a description of the work makes the Wall Street Journal think people will stop and read about this and feel like something significant is occurring in the world") the things they do will be extremely, powerfully not-stupid, and thus those things will have value and progress the business forward towards, you know, glory and what-have-you.

Well... let me assure you, as a seasoned professional with 20 (!) years of high-tech (well, mostly high-tech), growth company experience — working super hard and being a counterproductive idiot are not, I repeat, not mutually exclusive. In fact, the whole reason work-life balance even exists in a country where everyone is obsessed with their career and terrified of not being rich in the event they ever encounter even a moderate medical challenge, is because working too hard actually causes you to become an idiot and do stupid, counterproductive things at work. These things range from bad ideas, to yelling at people, to forgetting important things, to major industrial accidents, to being Boeing. All of them are bad, and businesses would almost certainly make more money and deliver improved customer experiences if we did/had less of them.

"Companies are in control again!" Eh, I dunno. I think companies were kind of always in control, since most people work for companies not because it's fun, but because they are financially dependent on those companies for survival. Really, companies have just gotten tired of trying to create environments where their employees don't do stupid things, probably because doing so is a vague, difficult and emotionally unsatisfying process.

Sending a picture of yourself pretending to sleep in your office to the Wall Street Journal is pretty stupid — you might even say "idiotic" in the context of building a successful technology product — but it's not vague, it's not especially difficult, and to people who feel limited in their ability to actually improve the performance of their businesses, it's probably somewhat satisfying.

Again, I've been working for a long time. And I know that overworking can be a thing really competent, awesome people do that, if managed very carefully, sometimes leads to amazing results that are hard to get in normal working cadences. I totally concede this, and I have allowed myself, my wife, and even some direct reports to occasionally overwork, knowing that I am running the risk of encouraging idiocy in myself or the people I care about. I do understand the tradeoff, I have pulled all-nighters, and I have in fact produced things that came out so good, and so cool, that they made me laugh deliriously at some ungodly hour of the morning. I'm sure I sounded not unlike... an idiot.

BUT, in general, most idiotic things aren't the wild-eyed second-order effects of genius leaving the body. They are just... stupid, and bad. Things like the worst kind of bloated PowerPoint, hundreds of poorly considered, off-the-cuff Google Doc comments, charts in SaaS apps that don't make any sense, the entire HubSpot user interface, and other unfortunate outcomes.

Making overworking a requirement, instead of something to manage effectively and with some degree of caution, doesn't open the floodgates to genius. It opens the floodgates to charlatans and delusional go-getters who are willing to sleep in the office after a long, exhausting day of making bad, impulsive decisions and generally making everything harder for everyone else, including you and your customers. If that's what you're going for in 2025, I'm neither all that surprised nor especially interested in hitching my wagon to your future success.

Work is Weird, Weird is Hard

Tue, 01 Jul 2025 14:53:20 -0400

One cool thing about life, or at least my life, is that as I've gotten older and moved around, I've gotten to know some people who do jobs that I've always been aware of, but actually know very little about. The challenge with these kinds of jobs (and there are a lot of them) is that people tend to conflate awareness that the job exists with any sort of actual knowledge about how to do the job, or at least what the challenges of doing the job are. In reality, other than things that affect all jobs ("we are overworked, our boss is an idiot who hates us", etc.), most of us have no idea.

"Air traffic controller" is a great example of a job like this, although to my knowledge, I don't personally know an air traffic controller. But it checks all the right boxes for confusing the public -- air traffic control as a concept makes sense, we've all been affected by it directly, it's in the news, it's in movies, we play little video games about it, and so forth. When I think "yeah, I get what they're going through up there" (and sometimes I do this) I'm obviously wrong about that, but I think my misplaced confidence is at least understandable.

The thing is, I'm just a guy. The fact that I lack high-level self-awareness of my gaps in how the national air traffic controller network works (or does not work) is not a huge problem for society, as long as I don't vote for idiots, I guess. Unfortunately, there ARE people who are in charge of large, sweeping decisions that affect — and are affected by — the actual work of being an air traffic controller. It does matter if they lack this kind of situational awareness, and according to the Verge, evidently they do.

Because of this whirlwind of activity, Rocheleau expected that Newark would soon be able to increase its flight volume by 25 percent, or nearly 12 additional flights per hour.

Or, as Kirby put it, “This is such a seminal turning point for not just the near term but the long term of Newark.”

Within two days, all three men were proven wrong. On the evening of June 4th, a shortage of air traffic controllers forced Newark to issue a ground stop, delaying more than 100 flights for several hours. Another staffing-related delay occurred four days later. Optimism alone cannot solve infrastructure problems that have been decades in the making.

The Verge piece continues, explaining that despite a brief, reactive surge of technical resources and equipment, a massive shortage of air traffic controllers — people — ultimately took down the system almost immediately.

"If your job is so complicated, how come you work for me?"

People's fundamental misunderstanding of on-the-ground effort feels like the root of so many problems today. We have strong opinions about manufacturing, but we don't know how actual things get made. We have strong opinions about immigration, but we don't know who these people actually are or what they actually do. The management class (a group I belong to, theoretically) is in the throes of a truly bizarre delusion that has them convinced content parsing and generating algorithms are about to take over useful, necessary work from people, and have actually started preemptively reducing headcount needed to do this work today.

The blind spot I'm describing is really just human nature, I guess, but it does seem to dominate problem-solving more than ever before. Some potential social factors encouraging this are well-documented, like the fact that modern America was built by a generation that collectively participated in a giant global conflict where everyone left was just glad they didn't die, whereas today the military is highly professionalized and most people never serve in it at all. Maybe that's it — Stephen A. Smith Hot Take Culture (tm) and every other modern example of people popping off without feeling the need to really understand the topic at hand can all be traced back to that, but I don't know, and it does seem like it's getting worse. Algorithmic, short-form-video-world isn't helping, but I can't tell if it's a cause, or an effect of this whole thing that just happens to reinforce the trends that inspired it.

I'm not sure what the solution here is. It's equally absurd to restrict opinions or observations to people with direct experience in something, so to me that's a non-starter. We can't all become experienced in everything (this is why the "I do my own research" thing is such a problem), either. For me, getting into management was really helpful because it was in a field and with a team that had me as a direct contributor, so I was under no illusion I suddenly knew how to do my former peers' jobs better than they did (they were also not under this illusion, and more than happy to express it to me when I needed to hear it). But authority actually seems to have the opposite effect on a lot of people, where it instead makes them comfortable dictating the larger strategy or resources behind a function without even a basic, existential awareness of the work itself. For me, leadership was consistently very humbling, but instead I frequently see leaders using their position as a leader itself to justify whatever their decisions turn out to be.

And maybe that's ultimately the issue. There will always be a need for someone to make decisions they don't have a lot of first-hand experience with. How things go for a business, or a society, or even a family are going to be determined in large part by how those decisions get made, and more specifically how those decision makers handle not knowing enough to make the right one.

Life is not a real-time-strategy game. It's not designed to be solved by one, brilliant person. The pieces are way more complicated, and unique, and weird, and sometimes the same piece that literally doesn't do anything for half the game becomes incredibly, existentially important when you least expect it. So many things that need to get done are weird, and specific, or stupid and broken and require someone to make a decision or concoct a good-enough solution that simply doesn't exist in any "training data", whether its used by a machine learning model or an MBA candidate. Trust me, I work in digital marketing right now. If I'm being honest, I do a lot of repetitive administrative work that should be automated, in theory, but the reality is that most of the automations built (by me or by vendors) with the intention of doing so are broken and unreliable because the inputs (and outputs) are bespoke and inconsistent. No one wants to do this work less than me, but I keep doing it, because I know how to ingest a typically random scenario and cobble together an environmentally-appropriate answer. Whether you're sponsoring an event or landing a plane, that's... that's the work, man! Forget it at your peril.

The Nothing App

Sun, 04 May 2025 09:12:31 -0400

I'm 43 years old, and I've been consuming technology products and working in tech basically my entire life, minus a year and a half where I worked for a catalog that sold garden gnomes. Nobody's perfect.

But the "tech industry", if that's still a thing we can demarcate, has some real existential problems right now, the main one being that it appears to be completely out of ideas. Well, maybe not so much out of ideas, but out of ideas that aren't just various commercialized versions of tech products and platforms senior executives read about or saw in movies as kids.

Elon Musk and Sam Altman are two of the most well-capitalized guys on the planet. No matter how much money they lose, for whatever reason investors are happy to continue shoveling money into whatever they want to do, and that comes at a pretty significant opportunity cost -- try getting a job in technology right now that isn't about generative AI, for instance. It's doable (I did it!), but it's really, really hard. But these two guys are really sucking up just an almost incomprehensible amount of venture capital and pouring it into... I guess NVIDIA? And that definitely has a non-trivial effect on the marketplace of available ideas.

Still, the worst part is that... none of this is going anywhere, at all. These companies will probably, for a fairly long time, have really high paper values that these two guys (and others) will be able to use as collateral to borrow money, avoid taxes, and live like kings forever, sure. People will use ChatGPT, other people (probably less) will post on Twitter, and all of those people will make stupid cartoon pictures of themselves through prompts. Musk is cynical enough to know he needs to be integrated with the government -- and in particular, defense -- to generate the guaranteed, endless revenue stream he needs to finance his nerd fantasies, and he may succeed at that.

But... "the everything app" these guys are obsessed with is not coming. They're not going to build it. No one is! There's been a lot of corporate consolidation over the years (too much, in fact), but one thing that remains extremely numerous are apps. In the 2010s, Facebook clearly wanted to be "the everything app" — maybe it still does! But they had years to figure it out, infinite money, and an ambitious, sociopathic super-dork running the show, just like these guys -- and they got nowhere at all with that.

We don't need an everything app. We have an everything device, the phone. And all this capital is going towards trying to put an unnecessary, platform eliminating app layer on top of it even though (a) there's nothing in it for consumers, who control some parts of their phone experience, and (b) there's nothing in it for Apple or Google, who control the rest. The most incredible achievement Sam Altman has pulled off is convincing Wall Street (and the media, and even Apple and Google to some extent) that chatbots somehow undermine this moat, when they do not, at all, in any way. I mean... Facebook even tried to make a phone! They knew what was up!

(Search is different. Google dropped the ball on search and now their offering is bad enough, and hard enough to get value from, that ChatGPT's bullshit machine is good enough for people, which is just an incredibly damning sign for the quality of search in 2025. But there's actually money to be made/lost in someone getting search right, or at least less wrong than it is right now.)

This whole Ready-Player-One everything app idea is just a giant waste of money that will never turn into anything real. And real, interesting ideas and iterative improvements to things you're actually going to use will continue to wither on the vine until we accept it and move on.

Wholly Lawless

Sun, 06 Apr 2025 21:17:37 -0400

This is an insane sentence to read in a story on a federal court ruling:

There is little to no evidence to support a “vague, uncorroborated” allegation that Kilmar Abrego Garcia was once in the MS-13 street gang, U.S. District Judge Paula Xinis wrote. And in any case, she said, an immigration judge had expressly barred the U.S. in 2019 from deporting Abrego Garcia to El Salvador, where he faced likely persecution by local gangs.

“As defendants acknowledge, they had no legal authority to arrest him, no justification to detain him, and no grounds to send him to El Salvador — let alone deliver him into one of the most dangerous prisons in the Western Hemisphere,” Xinis wrote.

I'll put this bluntly. There are many policy positions you can hold that — even if crazy — can fit inside the framework of American society and government prescribed by the U.S. Constitution. You can call different ideas "left-wing", or "right-wing", or talk about the importance of "liberty" or "security", and in most cases that can fit inside some still-defensible idea of how the United States could/would work.

However, the idea that the executive branch can unilaterally declare someone removable from the country, provide no proof, ignore the laws and procedures that legally require them do so, send them to a prison in El Salvador, and then declare that the person cannot be returned because they are now outside U.S. jurisdiction is fundamentally incompatible with not only the U.S. Constitution, but the basics of western law and morality that predate the formation of the country. It is, with zero exaggeration, a blank check for the administration to do anything they want to anyone with no repercussions. They just have to say you are in this gang, and you can be whisked away and never seen again.

For America to function as you expect it to (whether you are aware of this or not), the executive branch absolutely must provide some justification for what they are doing, and there absolutely must be a defined, pre-described forum for providing it and allowing for some form of pushback or counter-argument from the person that it is being done to, and all of this must be overseen and adjudicated by someone who is not the executive branch. It doesn't matter if the person is a citizen or not, because if the government isn't required to do this for everyone, they can just declare that someone is not a citizen and do whatever they want to them, because in that world ICE or the Army or the State Department or the USDA or whoever would apparently have the right to simply take any action they want and then wash their hands of the situation because the person has been sent off to some godforsaken prison hundreds or thousands of miles away.

This is so stupid and obvious I can't even believe it needs to be stated. If you can't understand this, I sort of feel bad for you, but mostly I am enraged you are such a useless, non-contributing member of our democracy, because it is so unbelievably uncomplicated that I struggle to see any reason other than willful, borderline malicious ignorance for not finding this completely outrageous and unacceptable. You absolutely do not need to be some political egghead to wrap your arms around the idea that the people and institutions who get the guns and the keys to the prisons need to have absolutely ironclad limitations placed on them and that those limitations cannot be defined or interpreted by them. If a bunch of farmers and shopkeepers and blacksmiths were able to figure this out and do something about it 300 years ago (at tremendous personal risk!), I feel like you can get there too.

And hey, if for some reason you can't get around the idea of non-citizens having rights of any sort (that's your problem to figure out, but I won't die on that hill here), remind yourself that this is not about anyone's positive rights, this is about fundamental restrictions on what the government can do. It's a check on them, you dummies, not a perk of being a citizen, because if they can do this they can just take away your perks whenever they want and they don't have to give a reason or explain anything about that reason to you, a judge, or your freaking family, who will never see you again.

Good lord. I spent four years sort of lazily piling up credits and stumbling out of college with a political science degree, and for the most part I felt silly because it seemed like all I learned was "how America works", which I sort of knew anyways, and which seemed like something everyone here would have to learn just walking around and living life, or else society would collapse. And maybe I was right, because now that most people don't seem to know any of this, the Republic does actually appear to be in some form of collapse.

Intentionally Spread Thin

Thu, 23 Jan 2025 19:01:11 -0400

OpenAI is shoving more stuff out the door that seems very early, very ambitious, and very janky.

OpenAI is releasing a “research preview” of an AI agent called Operator that can “go to the web to perform tasks for you,” according to a blog post. “Using its own browser, it can look at a webpage and interact with it by typing, clicking, and scrolling,” OpenAI says. It’s launching first in the US for subscribers of OpenAI’s $200 per month ChatGPT Pro tier.

Operator relies a “Computer-Using Agent” model that combines GPT-4o’s vision capabilities with “advanced reasoning through reinforcement learning” to be able to interact with GUIs, OpenAI says. “Operator can ‘see’ (through screenshots) and ‘interact’ (using all the actions a mouse and keyboard allow) with a browser, enabling it to take action on the web without requiring custom API integrations,” according to OpenAI.

One thing I learned working in all these tech startups is that the easiest way to solve extremely difficult "last mile" problems is to get distracted by something else and work on that instead.

The Employees You Want

Mon, 13 Jan 2025 22:14:34 -0400

Max Read has a secondary potential motivation (other than sucking up to an incoming Presidential administration) for Mark Zuckerberg suddenly reinventing himself as the least intimidating, least plausible right-wing tough-guy reactionary ever conceived:

"News on Friday that Meta is ending its D.E.I. program should be seen in this context--as not just another way to cozy up to the Trump administration, but as another sally in a war against a workforce that tech management has come to see as dangerously left-wing. I’ve argued before that the hard-right turn of investors like Marc Andreessen should be seen in part as a kind of marketing strategy, an attempt to find founders and workers whose politics make them less likely to jeopardize profits with workplace action.2I suspect that Zuck’s makeover functions at least in part in the same way. I don’t think Republican electeds much care if Zuck is cageside at M.M.A. matches or using right-wing slang like “legacy media” and “virtue-signaling”--but I think the kinds of employees he might like to attract probably do (As do, from the other direction, the kinds of employees he would like to attrite)."

Honestly, I have no real reason not believe this. It's not a stupid theory — it's a fairly compelling theory proposing that someone weird (and maybe, in their own way, stupid) is doing something stupid.

It's stupid for a couple reasons. It's stupid because you can already get whatever kind of workforce you want, and Facebook has been hiring what it wants for twenty years now. It wants "100x engineers", best in class, A-player, blah blah blah. That's what it's been hiring for better or worse. Never in Facebook's notoriously money and power hungry history has it said "we want this place staffed by a bunch of bleeding heart liberals". That was always the price of getting the people they wanted, and it was a price they paid happily to print money for, again, two decades.

This bring us to the second reason this is stupid. This is America — as much as corporations (especially tech companies, for whatever reason) seem to love coming up with elaborate, too-cute-by-a-half justifications for dumping workers, it's not really necessary. Americans have very few labor protections, and it's not hard to get rid of tens of thousands of workers. Traditionally, that sort of thing has hurt the stock price of public companies, but who knows if that would even happen now. So if you don't want most of your employees to be Facebook employees anymore (and the posturing of the last two years sure makes it look like he doesn't), just do your job and get rid of them. You don't even have to pay severance! I'm sure most of these people, like me, are at-will employees.

But... there is one little problem. These are still the kinds of workers you want — you just don't want them to be annoying or have principles or make you consider things you don't like. You want truly talented engineers and smart, technical business people who just love money and winning and crushing it, but... also people who thrive working inside a massive organization with huge egos, interdepartmental conflict, and often incoherent or incompetent upper management.

See where this is going? The first set of problems is very real, I get it. I once watched an intern launch into a rant at an all-hands meeting about how our executive team's answer on diversity "was frankly not good enough", and she was only there for the summer and didn't even do any work. But that's an extreme outlier. I've been working at tech companies for almost as long as Facebook has existed, and the best, most innovative, most effective employees I worked with (other than the occasional ruthless salesperson or actively hostile DevOps guy) were all basically kind, thoughtful, intelligent people. There's a type, man, and it's not AI-crypto-libertarian edgelord. Some of those people really are very intelligent and potentially very productive, but they generally don't scale well, they hate the bureaucracy and rules inherent in running a billion dollar business, and honestly, they're just a different kind of a pain-in-the-ass, and one you tend to run into a lot quicker. In other words, they'd all love to work with Mark Zuckerberg, as long as they can have his job where they can say and do whatever they want, change their mind on a whim, and never be held accountable for anything. As my uncle reportedly said when they reinstated the draft — "sure, I'll go to Vietnam. Just make me a general."

That's not who Zuckerberg and the rest of the "I'm a libertarian because I'm winning" crew actually want as mid-level product managers and data scientists. It'd be chaos, and far more insufferable than the occasionally eye-rolling left-wing status quo. Instead, these guys are just delusionally pining for their manic pixie dream girl — in their case, a brilliant, kind, innovative, competent professional who puts customers first, is willing to disagree and commit, and who also has absolutely no problem watching terrible, amoral shit go down on their watch as long as their boss says it's fine.

A few of these magical employees might exist, but there aren't nearly enough of them to staff Silicon Valley, which is why the only fantasy more appealing to these guys than a tech company staffed by obedient, professional, submissive right wing sociopaths is one staffed by large language mod-- sorry, I mean "AI Agents".

Three Pointers and The Angry Mob

Tue, 24 Dec 2024 16:01:20 -0400

John Hollinger is the first big, respected basketball name I've seen take a counterpunch at the puzzling (and omnipresent) narrative that the NBA is in some kind of death spiral.

Declining TV ratings. Endless fourth quarters thanks to timeouts, replays and clock stoppages. One-sided blowouts. A new December tournament format struggling to compete with the NFL colossus.

I’m talking, of course, about college football. Back in my day, there was real variety — Oklahoma won a national title running the wishbone! — but now everyone plays the same way. It’s all about passing, and whoever throws it better wins. No wonder ratings are down.

(*Sound of record scratching*)

I've been a pretty avid NBA fan for a long time, now. That includes some stretches where the basketball was... not very good. The immediate post-Jordan years, watching my 2002-era Celtics grind out brutal 81-78 playoff victories against the likes of the Al Harrington Pacers and the Jason Kidd Nets, the non-beautiful version of the Spurs (the Bruce Bowen era), and so forth. For the life of me, I just can't understand how any quasi-serious fan of the game could take this three point panic seriously, given the various ups and downs the league has been through over the years.

As with a lot of things, a big part of the problem is just a failure to accurately assess the situation. There are a lot more three pointers being taken now than even just a few years ago. That's an objective fact. But I definitely get the sense from people who are concerned about this trend that they either assume or believe from limited amount of game footage and YouTube clips that "three pointer" means basically pulling it up and chucking from far away, as some sort of alternative to traditional offense where you try to find an open shot.

If that were actually the case, I'd agree that there really was a problem. In fact, that really is my least favorite kind of basketball, but it's not limited to three pointers. It's iso-ball, a style best (and most efficiently) represented by peak-James Harden and recent-vintage Luka Doncic dribbling around with four guys spread around the court and looking to make something happen (and often succeeding). There are a lot of threes in that style, especially of the step-back variety. Just as importantly, there are a lot of foul shots, which are way more boring than threes. Worst of all, there's a tremendous amount of everyone else standing around.

But that's not the only way to shoot threes, and it's not powering the increase in threes we're seeing today. Instead, as Hollinger points out, a bunch of high usage players have started shooting 24 foot threes instead of 20 foot twos, with similar success rates but a lot more points. Hollinger also notes that spreads the floor for other things, to wit:

This is an important distinction when people talk about “too many 3s”: Shots at the basket are the same, and dunks — the most exciting play in the game — are the same 4.7 per team per game that they’ve been for the past two seasons. That may seem counterintuitive, but more 3s equal more spacing, which in turn equals more runway for dunks.

Look at the Celtics. When they lean on "dribble dribble shoot", it occasionally works, but most of the time the offense grows stagnant and they're beatable. But when they play basketball -- as they usually do -- their ability to hit threes turns into something almost indescribable.

You can see the way the aggressive use of three pointers befuddles even hardworking, hustling defenses, but it certainly isn't somebody scared of contact resorting to "dribble dribble shoot".

And while there are definitely loud, "too many threes" critics who are also pretty sophisticated basketball fans, I'd be lying if I said I didn't notice a correlation between much of the "too many threes" crew and the equally angry "the league is too soft" crew. But Hollinger addresses this as well -- after an initial gasp at the sudden physicality added to the game in the middle of the season last year, everyone seems to have forgotten about that and simply moved on to complaining about threes again.

I feel like I’ve seen my fair share of awesome games this season, both in-person and on TV, and that’s pretty much been the case ever since the league decided at last season’s All-Star break that it was going to chill on calling so many fouls when players drive to the basket. The result has been some of the most watchable, entertaining and stoppage-free basketball of the last quarter century.

That, to me, is the story: that the league enacted a fairly sudden change to make its product massively better. An underwhelming postseason likely prevented many people from noticing, especially the generalists who parachute into the NBA in April.

I actually think there's a relationship here, but it's not what the overlapping part of the too-soft/too-many-threes Venn diagram wants to hear. I think the two trends are actually related -- the more physicality you allow near the basket, the more it makes sense to shoot threes. Allowing defenders to grab and pull underneath the basket makes driving to the basket or playing in the post more difficult, and less efficient. It might hurt three point shooting a little bit, by simply allowing defenses to focus more on threes, knowing they are more likely to get away with simply clobbering anyone who gets by them, but it impedes the things people claim to want to see even more. At some point, I'm not sure what some of these casual fans even want, or if they'd recognize it if they got it. If you want to see Shaq post up and run people over, I mean... we've got Giannis, right? He's a different player than Shaq, but he's incredibly well-known, one of the leading scorers in the league, and he absolutely lives in the paint!

(I know this clip is old, but nothing's changed here -- if anything he's even better at this now.)

Would it somehow be better if somebody like Nikola Jokic couldn't shoot threes? Wouldn't not being a threat from all around the court just make him a less interesting passer (Arvydas Sabonis was amazing, for instance, but Jokic is just a better, more broadly effective offensive player)? And can you seriously make the case that modern guards and wings are somehow less broadly skilled than prior generations, or unable to do anything besides cower behind the line and heave up prayers?

This just seems like yet another one of these "I know it when I see it" complaints about the NBA that the league seems inherently susceptible to. I'm not interested in hockey, and I tend to get bored when I watch it, but I don't have some laundry list of things I think the NHL is doing wrong, nor do I think the NHL has "lost their way" and needs to return to some glorious prior age. I have lots of thoughts on pass interference and offensive holding occurring on every play, but until ex-players actually started killing themselves and leaving behind suicide notes begging their families to have their brains examined for traumatic damage, I didn't think the NFL was in some existential crisis.

But everyone has a hot take on basketball. It's hard for me to believe that for many people, there isn't some unspoken, subconscious connection between how undeniably minority powered the league is (the biggest stars and best players are generally black americans, europeans, or increasingly, black europeans) and how endlessly critical and pearl-clutching we always seem to be about the direction the game is going, no matter what that direction is. For years, grumpy old white Dads would complain that no one could shoot. Today, those same grumpy Dads see the proliferation of exceptional long-distance shot making not as a return to graceful, skill-driven basketball, but as something that needs to be stopped by any means necessary.