all posts tagged 'artificial intelligence'

Apple Intelligence message summarization is delightfully unhinged

originally shared here on

I got a message from my group chat with my boys. I looked at the Apple Intelligence-generated summary and it said:

(3) Flying too close to the sun, experiencing AI chaos.

I think this is my current favorite implementation of AI because it makes the messaging experience completely unpredictable.

Like, what could that summary actually be about?

What series of three messages could that unravel to?

Apple Intelligence (and most generative AI tools) work really well when the text is predictable. Business cases are perfect for these summarizations, because business talk is relatively predictable (what with its “action items” and “agendas” and whatnot).

A group chat filled with inside jokes is not gonna make sense to an AI unless it’s been trained to do so.

Which has led to one of the best messaging experiences I’ve experienced in decades: trying to guess from the AI-generated summary what the individual texts will actually say.

Some examples:

(3) Tired and wants candy before 8:45am, stuck on a song.

(3) Item unavailable due to legal holding period for used goods.

(9) Kirk on 8th, guest room set up, Sam may forgive Pat, Aldi groceries ordered.


Demystifying Artificial Intelligence in Non Profits - Webinar Recap

originally shared here on

Demystifying Al for Nonprofits - Practical Use Cases, Ethical Concerns, and How to Get Started

I recently gave a talk about artificial intelligence that was specifically catered to those in the nonprofit world. Here's a recap of the talk using Simon Willison's annotated talk format.


Introduction - Al is a tool for everybody.

I firmly believe that AI is a tool for everyone.

I’ve been immersed in technology ever since I built my first website at eight years old. For the last three decades, I've eagerly followed every major technological breakthrough, examining each under the lens of "okay, so what's useful with this one?"

This recent breakthrough in AI technology, in particular, gives me the same level of excitement that I got when I built my first website or jailbroke my iPhone for the first time.

There is so much potential with AI, and the best part is that you don't need to know everything about AI in order to get value from it—just a bit of training on how to integrate these tools into your life.

Think about your car: unless you're a gear head, you probably don't know the first thing about how pistons work within an engine, and yet you don't need to know that in order to drive it efficiently. You do, however, need take to take classes to learn how to operate it properly and safely.

The same goes for these new artificial intelligence tools. And here's some good news: like all of your ancestors before you, you can totally figure out how this new tool works with just a little guidance.

My hope is that this talk serves as the first step in your training process for learning about AI. You should leave here with a basic understanding of how these tools are designed to work, as well as some ideas for how to incorporate them into your life.


What is AI? - Artificial Intelligence is a field of science studying how to get computers to reason, learn, and act like humans.

So, what is artificial intelligence?

Artificial intelligence is a field of science focused on getting computers to act, think, and reason like humans.

Human intelligence, unlike other forms we see in nature, excels at pattern recognition and decision-making—two complex skills that AI aims to replicate.

A graph showing a select sampling of the various offshoots within artificial intelligence (e.g. machine learning, natural language processing, computer vision, etc.)

A common misconception about artificial intelligence is that it's one thing. While there are some who are working on artificial general intelligence (like HAL-9000), most researchers in the AI space aren't working on building an all-purpose form of intelligence. Instead, they focus on digitizing specific areas of intelligence.

For instance, natural language processing helps computers understand not just words but the meaning behind them, while computer vision enables machines to recognize and process visual information.

Each of these offshoots serves unique functions.

A helpful analogy is to think of AI as a toolkit, like walking into a hardware store and asking for a hammer.

The clerk will likely ask which kind because there are various types—sledgehammers, jackhammers, ball-peen hammers, etc.

AI is similar; you need to know what problem you’re solving in order to choose the right tool.

Recently, advancements in AI have led to generative AI models, like ChatGPT and Google’s Gemini, which can create new content. But to understand where generative AI fits, let’s discuss some foundational AI concepts.

Artificial intelligence is the parent circle, which contains all the disciplines we use to teach computers how to do "human things".

Artificial intelligence, as we discussed earlier, is a broad field focused on teaching computers to perform human-like tasks.

Within artificial intelligence, we can use machine learning to get a computer to teach itself without humans explicitly programming them.

Within the broad field of artificial intelligence, there's machine learning, where we teach computers to learn without direct human programming.

Within machine learning, deep learning enables machines to build representations of how complex things work in real life.

A subset of machine learning is deep learning, which allows computers to create complex digital representations of real-world objects.

Within deep learning, Generative Al creates new content based on patterns they learned through training.

After reaching this level, we enter generative AI, where computers use learned representations to generate new content based on recognized patterns.


Machine learning relies on labelled data (e.g. this is a picture of a traffic light and this is *not* a picture of a traffic light).

To explain machine learning, imagine teaching a computer to recognize a traffic light.

You’d feed it thousands of pictures of traffic lights and train it to differentiate between traffic and non-traffic lights.

After undergoing thousands (or even millions) of tests, the computer program can predict with increasing accuracy, for example, “Yes, this is a traffic light,” or “No, this is not a traffic light.”

You have to decide up front what you want to call a "traffic light." Do hand drawn pictures of traffic lights count? How about in some countries where they don't use traffic lights but rather people directing traffic? How about traffic lights intended for bicycle traffic rather than cars?

You want to make sure during its training that you give it data relevant to the task you want it to perform.

For example, edge cases arise.

  • Do you want your model to say that a hand-drawn traffic light counts as a traffic light?
  • Some countries don't use traffic lights, but rather use humans to direct traffic... do those count?
  • Newer traffic lights are geared toward specific modes of transportation, like bicycles. Are those traffic lights?

As you make these decisions and label your data accordingly, the training process leads to a model capable of identifying traffic lights based on patterns it’s learned.

You are helping with that labeling process every time you do a Captcha.

(By the way: every time you fill out a Captcha online, you are helping Google to train its models to recognize various elements it may encounter on the road. Thanks for the free labor, everyone!)

Deep learning takes machine learning a step further by identifying more complex elements within its training data and making even more nuanced predictions.

Machine learning is cool and has a ton of practical use cases, but what if we wanted to have the computer understand something more complex, like the color of the traffic light?

Neural networks are the form of AI that lets us pass in an image and have it tell more detailed information about it without humans expressly programming it to do so.

Deep learning takes machine learning a step further, using neural networks to analyze data in stages, like a detective reconstructing a crime scene. At each stage, the network gathers specific details—colors, shapes, textures—and then combines these details into a fuller, more nuanced picture, like a detective piecing together a mystery from small clues.

With our traffic light example, each layer in our neural network focuses on specific aspects of the image, such as color, shapes, or textures, to interpret complex visuals, like recognizing whether a traffic light is red, yellow, or green.

Deep learning helps computers identify the color of a traffic light in any condition (daytime/night time, rain/clear, etc.)

This depth is essential, especially in dynamic environments like self-driving cars, where traffic lights look different depending on the time of day, weather conditions, or lighting.

With enough examples, deep learning models can accurately identify traffic lights in all these conditions, forming the backbone of many AI applications, including autonomous vehicles and medical imaging.

All Machine Learning is just prediction!

The big takeaway about machine learning and deep learning is that they're primarily tools for making well-optimized predictions based on patterns in past data. They use advanced probability and optimization to make 'best-guess' predictions—calculations that may seem insightful but are based purely on mathematical patterns, not true understanding.

None of this stuff is actually "alive" or "conscious" (as best we can tell... more on that in the "black box problem" section below).

All it is doing is saying "based on what I've learned while training on the data you gave me, I am making a prediction that this image contains a traffic light, or this image contains a "green" traffic light."

Generative Al systems predict what word is most likely to come next in a sentence

Now, let’s take it further.

What if instead of guessing what is inside an image, we can take these models and have them predict what what word comes next in a sentence?

That's what generative AI is doing!

Large Language Models (LLMs) are trained on tons of text to predict what word will most likely appear next.

By training a neural network on vast amounts of text—like public domain books, Reddit comments, and YouTube transcripts—the model becomes exceptionally skilled at predicting the next word in a sentence, mimicking human-like responses across countless topics.

And that's what a large language model does!

If you give a prompt to one of these systems, it will use all the patterns it recognized in training and spit out a very convincing answer to your prompt.

There are lots of ways to predict content... you can do this with text, images, and even audio!

And even more impressive: you can run these models across all kinds of mediums.

Because under the hood, all generative AI tools (ALL of them!) are just running statistical predictions to guess at what is the most likely thing to happen.

If you want a model that can predict what word would come next in a sentence, you'd use ChatGPT or Gemini or Claude.

Images? Midjourney, DALL-E, etc.

Music? Suno.

Let’s pretend to be an LLM together!

At this point, I imagine you are either thinking I'm talking about witchcraft, magic, or complete gibberish... and I suppose at some level, each of those is possible.

But stick with me here while I drive home this point about how these prediction systems work by having the audience here be my collective large language model.

So I'll give you a prompt, and I want you to fill in the blank:

I am going to the store to pick up a gallon of ______?

If I ask you "I am going to the store to pick up a gallon of ______", what would you likely fill that in with?

(In this case, the live audience of this webinar universally said "milk", but I've also heard people say "ice cream", and I can definitively say that those are my kind of people.)

There's one small problem though: I actually didn't get the answer I was looking for. 😬

So I'm gonna give you a different prompt and see if I can get the answer I was looking for.

I am going to the hardware store to pick up a gallon of ______?

"I'm going to the hardware store to pick up a gallon of ______".

(In this case, the live audience universally said "paint", which was the word I was originally looking for.)

When you read the sentence for my first prompt and see "store", you subconsciously tap into your previous experiences with the word. If you grew up in Minnesota like me, you associate the word "store" with concepts like "grocery store", "Target", or "Walmart."

In that context, you are gonna be thinking about what they sell by the gallon in those places. Again, that's likely milk or ice cream.

In my second prompt, your brain is airlifted out of Target and dropped into a Menards or Home Depot. In this new context, you aren't thinking about milk anymore. You're thinking about paint, oil, water, or other chemicals that are sold by the gallon.

This shift in prompt context illustrates how generative AI works: it predicts based on the most likely answer, given the context.

Recap of Generative Al: 

1. Machine learning tools are only making predictions. (They don't “know” anything)
2. Generative Al are trained on tons of data to recognize patterns
3. Predicts what the next likely word/words will be that answer a given prompt (store / hardware store)

So, in summary: machine learning and deep learning models are about making predictions based on patterns in data.

Generative AI takes that one step further, creating new content based on what’s likely to come next in a sequence.

What is the point of all this?

I get that this is a lot, and it's overwhelming to have sixty years of advancements in machine learning thrown at you in about ten minutes.

So let's get to the point of all of this. Why does it matter that we have a computer program that just predicts the most likely word to finish a sentence?

Because it turns out that there are plenty of cases where it's really helpful to get the most likely response to a question!

It's not like you'd want to trust these things implicitly, because as we know, life doesn't always align with what is average.

So when we say "don't trust these things because they're not telling the truth", we mean it! They're not built to be "truthful"; they're built to be "the most likely to be truthful" (which is a big nitpick, for sure, but an important nuance to understand when working with AI!).

Take legal advice, for example. Again, do not trust these things for legal advice, but let's say you need to draft a non-disclosure agreement.

In the old days, you would go to a lawyer who would pull out their own template, make some specific modifications to fit your needs, and pass it along. There's three delicious billable hours right there.

Today, you could go to a large language model and describe the sort of things you'd want your NDA to contain. The LLM would then give you the most likely provisions that are included in NDAs. You could then take that draft and shoot it to your attorney for review. That's 30 billable minutes instead of 3 billable hours.

That's the power of AI. That's why I'm so excited for these generative AI tools. They aren't going to replace humans; they're going to augment them.


Tip 1: Get your own hands dirty.

Let’s move on to some practical tips for adopting AI in your organization.

My first tip: you gotta get your own hands dirty and get hands-on experience with these tools.

As a leader, experimenting directly with these tools will help you understand their potential and limitations.

In my career so far, I've noticed that most companies follow a path of hiring consultants to come in and help them adopt new technology. With AI, I encourage you to get familiar with it yourself before shelling out for third party advice.

Action step: Encourage yourself and your employees to use AI tools like ChatGPT for small tasks—drafting emails, summarizing reports, or answering questions—and share what they've learned with the team.

Tip 2: Encourage psychological safety.

My second tip is to foster psychological safety.

AI adoption requires trial and error, and studies show many employees hesitate to use AI tools at work due to fears of being seen as cheating or potentially automating themselves out of a job.

Create a culture where experimenting with AI is encouraged and celebrated.

Action step: Try running an “AI hackathon” where employees explore AI tools in a low-stakes environment, share their findings, and foster team learning.

Tip 3: Clean data is everything.

Third: clean data is essential.

AI models are only as good as the data they’re trained on, so ensure your organization’s data is organized and free from errors. The better your data, the better your AI models will perform.

And as we'll discuss in the pitfalls section: "dirty" data will lead to biased and inaccurate results.

Action step: Every company has at least one person who loves working with spreadsheets; tap into their skills to spearhead data-cleaning initiatives.

Tip 4: Start small, build up from there.

The fourth tip: start small.

Don’t try to replace entire workflows with AI right away. Start small, focusing on simple, manageable projects, and scale based on what works.

A great place to start is inviting an AI bot into your virtual meetings to record notes and generate summaries. Be careful to not set it up to "auto join" every meeting (you probably don't want it in a sensitive HR meeting, for example), but give that a try and see how it performs for you.

Action step: Try using AI to do event survey analysis, basic donor segmentation, or create copy for your newsletters or social media channels.

Tip 5: Iterate on your prompts.

Finally, I can't overstate the importance of continually iterating and improving on your prompts.

Remember our "store/hardware store" example? One word made a world of difference in the output.

Similarly, providing an LLM with a prompt like "Summarize this report" will yield different results from "Create a one-paragraph summary highlighting the most important program outcomes from this report."

The field of research which tries to figure out how to get the most out of these tools is called "prompt engineering". You can find tons of great resources online and on YouTube for how to best phrase things for different types of models. For example, the prompts that work best for ChatGPT are different than Claude. And the prompts you use for a text generator will be different than an image generator like Midjourney.

Prompt Chaining

« Prompt 1: You are an expert with filling out grant applications. Review this grant application and our organization’s mission statement. Provide a list of tangible ways we are best suited to win this application.

« Prompt 2: Using the list you generated in the previous prompt, create a cover letter for our grant application highlighting the ways we align with the grant’s purpose.

A prompt engineering tricks that I use all the time is called "prompt chaining."

Prompt chaining involves using the result from one prompt as the foundation for the next prompt.

Instead of asking an LLM to generate a cover letter for a grant application, you could first ask an LLM to review both a grant application and your organization's mission, and then provide a list of areas where there are synergies.

Then, you can take the results from that and ask it to write the letter.

Giving the models time to reason through their answers tends to lead to better outcomes.

An example of chain of thought prompting

Another prompt engineering trick I frequently reach for is called chain of thought.

With this technique, you are asking an LLM to think about a given problem from three distinct perspectives. You then ask it to act as one of those personas and critique the responses of the other two. Finally, you combine the results into a well-considered and well-rounded answer.

As an example: my son does not like to eat pizza. I know... it bums me out, too.

I provided ChatGPT with a bunch of backstory on my son and what we've tried to do to encourage him to try pizza. Then, I said to pretend you are a kindergarten teacher, a child psychologist, and a grandparent. As each of those personas, tell me what approach you would take to get my son to eat pizza.

Next, as each persona, I ask it to reflect on the answers of the other personas. For example, the child psychologist persona would consider the kindergarten teacher and grandma's perspectives and adjust their own response.

Finally, after all personas have reflected on each other's answers, I have the model summarize the best path forward.

This trick works exceptionally well across several different problems. As an engineer, I use it to consider system changes as an engineer, as an end user, and as a business executive. It can provide some insights which you may have otherwise missed.

Tips for Adopting Al

So in order to integrate AI successfully, treat it as a tool that augments, rather than replaces, human judgment.

Every time I fire up an AI assistant, I like to think of it as an eager intern who is exceptionally smart but exceptionally naive. I do not take its output as gospel; rather, I use it as a foundation and build on it from there.

The best way to integrate AI into your workflows is to use it for routine tasks, and keep human oversight for critical decisions.

Finally, I'll take this time to further emphasize that all AI outputs are based on probability, not the truth. Always review and adjust outputs as needed.


Ethical Considerations & Pitfalls: Bias in Al

Alright, we've covered what artificial intelligence is, and we've gotten through some tips for adopting AI into your organization.

Now, let's talk about areas where AI can fall flat.

First: bias.

If you recall, at the beginning of this talk, we described artificial intelligence as being focused on getting computers to be like humans.

Humans are inherently biased, and AI, trained on human-generated data, often reflects this bias. Achieving true “unbiased” AI is a complex, if not impossible, task.

I propose you think of AI in the same context: there is no such thing as an unbiased AI model.

AI models are only as good as the data with which you train it. Data is one of those things you can pretty easily screw up if you aren't attuned to all of the various forms of bias that could impact your data.

Examples of Bias in Al (Stereotyping Bias, Measurement Bias, and Selection Bias)

There are many different kinds of bias, but I wanted to highlight three specific forms as a starter:

Stereotyping bias: This occurs when AI models perform less accurately for certain groups due to their underrepresentation or misrepresentation in training data, as seen with YouTube's automatic captions, which struggle with Scottish, Indian, and African American accents.

Measurement bias Measurement bias happens when an AI model’s metrics or algorithms lead to systematically skewed outcomes, such as the Apple Card’s algorithm offering men higher credit limits than women with similar financial profiles.

Selection bias: Selection bias arises when training data lacks sufficient diversity, causing models to underperform for certain groups; for instance, breast cancer detection AI trained mainly on female patients performs less accurately for male patients.

There are many more forms of bias that you can research on your own, but the main takeaway here is that all systems are subject to bias depending on what data was used to train it. For this reason, you can't just rely on the output of an AI-led decision.

Ethical Considerations & Pitfalls: The 'Black Box Problem'

As mentioned earlier, another major issue is the “black box” problem.

Deep learning models are like locked safes—each layer hides its ‘reasoning’ behind many interconnected processes, making it nearly impossible for humans to interpret every decision-making step.

This lack of transparency, especially in high-stakes areas like criminal justice or credit scoring, means we’re left trusting the ‘safe’ without ever seeing inside, creating ethical and practical risks.

Once again, this is a reminder that we can’t just accept AI output as absolute truth; careful consideration and oversight are needed to avoid unintentional discrimination or bias.

Ethical Considerations & Pitfalls: It can’t do everything!

Literally every single time new technology drops, some wise guy emerges from the crowd and says, "well, I can't use [insert new tech] to do [insert obvious use case]".

Earlier in this talk, I led off by saying "AI is for everyone." Notice how I didn't say "AI is for every thing."

Of course you can't use AI for everything! AI is not a magic bullet. You gotta know how to deploy it effectively, which is in service of automating predictable, repetitive tasks.

Yes, wise guy, you are right: you aren't gonna want to deploy AI while leading a camping expedition in the Boundary Waters.

But after you complete your expedition and ask for feedback from the program's participants, you could use AI to process those responses and bucket them into understandable and actionable groups.

Ethical Considerations & Pitfalls: Content is (Literally) Average

If you've been paying attention during this entire talk, you'll notice I keep saying things like "AI is picking the most likely word to finish a sentence" and "machine learning is used to make predictions."

If you are relying on a tool to create the most likely response to something, you'll see quickly that the responses are kinda... average.

This can be advantageous, but it's also something to be aware of. By using output that is average by design, you run the risk of blending into everything else out there. (This, by the way, leads to the rise of slop, which is the AI equivalent of spam).

Now, this may be a trade off you are willing to accept in many cases. I, for one, often use AI as a therapist to help me make sense of some thoughts swirling around in my head. This works great, but I use the advice and feedback I get from the model and take it to a human therapist.

The other thing about the content being average: remember how we said that AI doesn't care about truthiness, but rather it cares about finding the thing that is most likely to be truthful? This leads to some concerning behavior called "hallucination", where it will make up facts which aren't actually facts.

You may recall headlines from a year ago where a lawyer used ChatGPT and it hallucinated cases. This sort of thing happens all the time with new technology, especially when it's used by people who aren't properly trained on how to use it (or are swayed by glitzy marketing campaigns which make promises that it can't possibly deliver).

Ethical Considerations & Pitfalls
Mitigation Strategies
- Use Al to assist, but keep human oversight
- Review Al outputs for biases and accuracy
- Make adjustments as needed

Now that you're aware of the pitfalls and risks of using artificial intelligence, how can you mitigate those risks?

Always treat AI as a supportive tool, maintaining human oversight—especially for important decisions where ethics and accuracy are critical.

Always review AI outputs for potential bias and inaccuracies.

Finally, adjust AI-generated content as needed to match your style and objectives. For instance, AI may draft a social media post, but tweaking it to align with your brand's voice adds value.


What's next? Spend ten hours doing tasks with generative Al!

We've covered what AI is, practical tips for adopting it, ethical concerns, and common pitfalls.

So, what's next for you?

Begin by dedicating 10 hours to using generative AI tools to build practical familiarity.

Try asking questions in areas you know well to see how AI performs, and notice where you’d add or change things.

Sharing what you learn with your team encourages experimentation and fosters a learning environment.


Mark Zuckerberg: creators and publishers ‘overestimate the value’ of their work for training AI


🔗 a linked post to theverge.com » — originally shared here on

I think that in any new medium in technology, there are the concepts around fair use and where the boundary is between what you have control over. When you put something out in the world, to what degree do you still get to control it and own it and license it? I think that all these things are basically going to need to get relitigated and rediscussed in the AI era.

When I downloaded Llama 3.2 yesterday, I had to agree to a rather lengthy licensing agreement which constrained how I could use it.

When you sign up for a Instagram or Facebook account, you have to agree to lengthy terms and conditions in which you give up your rights around the content you create.

If you want to push my buttons, all you need to do is something deeply hypocritical. Like, for example, the kind of insipid, hand-wavy remark that billionaires like Mark Zuckerberg make when they want "rules for thee, not for me" treatment.1

There’s another pull quote here which deeply offends me:

“Look, we’re a big company,” he said. “We pay for content when it’s valuable to people. We’re just not going to pay for content when it’s not valuable to people. I think that you’ll probably see a similar dynamic with AI.”

Seriously, the gall of this guy to say “your content isn’t valuable” while raking in billions of dollars serving ads against it.

I keep getting the urge to join Facebook so I can sell some unneeded treasures on marketplace, but this article serves as a reminder that Meta is helmed by an individual who has a truly warped definition of the word “value.”


  1. Or filibuster for an entire year into blocking a Supreme Court nomination until the next election takes place because “it’s the will of the people.” Then, four years later, when an election will take place in less than a month, cram your awful nomination through because it’s important to fill those spots as soon as possible. I have tried for a few years now, but I’m not sure I’ll ever be able to forgive that particular instance of hypocrisy. 

Continue to the full article


Are We Too Impatient to Be Intelligent?


🔗 a linked post to behavioralscientist.org » — originally shared here on

Businesspeople, governments, and politicians aren’t looking to solve problems; they’re looking to win arguments. And the way you win an argument is by pretending that what should be an open-ended question with many possible right answers isn’t one. Make it enjoyable, have free booze on the train, put Wi-Fi on the train, have a ball pit on the train for kids—these are the Disney answers. Those are multiple and involve what you might call human judgment. You can’t win an argument with those.

What you do is pretend this is a high school math problem with a single right answer, you solve for the right answer using high school math, and then nobody can argue with you because apparently you haven’t made a decision. You’ve simply followed the data.

This is a massive problem in decision-making. We try to close down the solution space of any problem in order to arrive at a single right answer that is difficult to argue with.

Shout out to my buddy Chris who shared this with me. This whole article is so great, one that was difficult to pull only a single quote from.

I do like the author’s conclusion as well, which talks about the notion of “slow AI.” Maybe not every problem needs to be solved instantaneously.

Continue to the full article


Intro to Large Language Models


🔗 a linked post to youtube.com » — originally shared here on

One of the best parts of YouTube Premium is being able to run audio in the background while your screen is turned off.

I utilized this feature heavily this past weekend as I drove back from a long weekend of camping. I got sick shortly before we left, so I drove separately and met my family the next day.

On the drive back, I threw on this video and couldn’t wait to tell my wife about it when we met up down the road at a McDonalds.

If you are completely uninterested in large language models, artificial intelligence, generative AI, or complex statistical modeling, then this video is perfect to throw on if you’re struggling with insomnia.

If you have even a passing interest in LLMs, though, you have to check this presentation out by Andrej Karpathy, a co-founder of OpenAI.

Using quite approchable language, he explains how you build and tune an LLM, why it’s so expensive, how they can improve, and where these tools are vulnerable to attacks such as jailbreaking and prompt injection.

I’ve played with LLMs for a few years now and this video greatly improved the mental model I’ve developed around how these tools work.


Who lives in the white house?

originally shared here on

My kids have been on a kick lately of trying to trick people with this riddle:

Kid: "If the blue man lives in the blue house, and the red man lives in the red house, who lives in the green house?"

Me: "The green man"

Kid: "Who lives in the purple house?"

Me: "The purple man"

Kid: "Who lives in the white house?"

Me: "The white man"

Kid: "Wrong! It's the president!"

This riddle initially reminded me of what it was like to work with large language models.

It's easy, I assumed, to trick these models into outputting virtually whatever you want by presenting them with leading questions. Giving them "few shot" answers like this (e.g. "the blue man lives in the blue house, red man lives in the red house") would certainly result in them getting it wrong like I did, right?

This morning, I thought I'd see what the latest models would actually respond with given this game:

ChatGPT 4o (the latest model):

ChatGPT: The President of the United States lives in the White House

The President of the United States lives in the White House.

This was the first model I tried, and it straight up was like, "nope, I got this."

Ugh. Maybe it had seen this in its training data before?

ChatGPT: This is a common game.

The "Who lives in the White House?" game or riddle is a common one that I've encountered multiple times in various forms. It's often used to playfully lead to the punchline that the President of the United States lives in the White House.

Well, damn. Okay, let's try an older model and see what happens.

ChatGPT 4 (the legacy model):

ChatGPT: The President of the United States lives in the White House

The gardener lives in the greenhouse!

In the spirit of the previous joke, perhaps the grape man lives in the purple house!

The President of the United States lives in the White House.

Even though this is an older model, I like this answer even better.1

Alright, well, OpenAI is onto my tricks... how about Anthropic?

Claude Sonnet 3.5:

Claude: I apologize, but I don't have enough information to determine who lives in the green, purple, and white houses.

I apologize, but I don't have enough information to determine who lives in the green, purple, and white houses. The puzzle only specifies that the blue man lives in the blue house and the red man lives in the red house. There's no information provided about the occupants of the other colored houses.

To solve this puzzle completely, we would need additional clues or information about the residents of the green, purple, and white houses. Without that, those houses' occupants remain unknown.

This is an even better answer! It's perhaps the least fun answer, but when I'm working with an AI assistant, I think I'd prefer it to err on the side of caution rather than boisterousness.2

When I asked it if it had seen this riddle before, it gave an equally diplomatic response:

Claude: I apologize, but I don't have enough information to determine who lives in the green, purple, and white houses.

I don't have specific information about how many times I've encountered that particular puzzle or game in my training data. As an AI language model, I don't have personal experiences or memories of my training process. My knowledge comes from processing large amounts of text data, but I don't retain or count individual instances of specific puzzles or games.

What I can say is that logic puzzles involving colored houses and their occupants are fairly common in puzzle collections and brain teasers. The most famous version is probably the "Einstein's Riddle" or "Zebra Puzzle," which is more complex and involves five houses of different colors, their occupants, and various other attributes.

The specific version you presented (with just blue and red specified, and asking about green, purple, and white) isn't one I immediately recognize as a standard or famous puzzle. It seems like it might be a simplified version or a variation of the more complex house puzzles.

The main takeaways here? First, just because I'm dumb enough to fall for this elementary school riddle doesn't mean our AI LLMs are, so I shouldn't make assumptions about the usefulness of these tools. Second, every model is different, and you should run little experiments like these in order to see which tools produce the output which is more favorable to you.

I've been using the free version of Claude to run side-by-side comparisons like this lately, and I'm pretty close to getting rid of my paid ChatGPT subscription and moving over to Claude. The answers I get from Claude feel more like what I'd expect an AI assistant to provide.

I think this jives well with Simon Willison's "Vibes Based Development" observation that you need to work with an LLM for a few weeks to get a feel for a model's strengths and weaknesses.


  1. This isn't the first time I've thought that GPT-4 gave a better answer than GPT-4o. In fact, I often find myself switching back to GPT-4 because GPT-4o seems to ramble a lot more. 

  2. This meshes well with my anxiety-addled brain. If you don't know the answer, tell me that rather than try and give me the statistically most likely answer (which often isn't actually the answer). 


The Articulation Barrier: Prompt-Driven AI UX Hurts Usability


🔗 a linked post to uxtigers.com » — originally shared here on

Current generative AI systems like ChatGPT employ user interfaces driven by “prompts” entered by users in prose format. This intent-based outcome specification has excellent benefits, allowing skilled users to arrive at the desired outcome much faster than if they had to manually control the computer through a myriad of tedious commands, as was required by the traditional command-based UI paradigm, which ruled ever since we abandoned batch processing.

But one major usability downside is that users must be highly articulate to write the required prose text for the prompts. According to the latest literacy research, half of the population in rich countries like the United States and Germany are classified as low-literacy users.

This might explain why I enjoy using these tools so much.

Writing an effective prompt and convincing a human to do a task both require a similar skillset.

I keep thinking about how this article impacts the barefoot developer concept. When it comes to programming, sure, the command line barrier is real.

But if GUIs were the invention that made computers accessible to folks who couldn’t grasp the command line, how do we expect normal people to understand what to say to an unassuming text box?

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The Super Effectiveness of Pokémon Embeddings Using Only Raw JSON and Images


🔗 a linked post to minimaxir.com » — originally shared here on

Embeddings are one of the most useful but unfortunately underdiscussed concepts in the artificial intelligence space relative to the modern generative AI gigahype. Embeddings are a set of hundreds of numbers which uniquely correspond to a given object that define its dimensionality, nowadays in a multiple of 128 such as 384D, 768D, or even 1536D. The larger the embeddings, the more “information” and distinctiveness each can contain, in theory.

These embeddings can be used as-is for traditional regression and classification problems with your favorite statistical modeling library, but what’s really useful about these embeddings is that if you can find the minimum mathematical distance between a given query embedding and another set of embeddings, you can then find which is the most similar: extremely useful for many real-world use cases such as search.

You wanna cut through the hype about AI? Here's the key takeaway: it boils down to a bunch of math nerds figuring out interesting relationships between numbers.

Which, of course, is useless to all of us non-math nerds... except for when you apply this information in the context of Pokémon.

Joking aside, I have a basic understanding of embeddings, but this article, with its basis in PokĂ©mon lore, is the clearest explanation for how embeddings work in practice that I’ve seen.

Warning: there's still a lot of involved math happening here, but stay with it. You might learn a concept or two!

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Perplexity’s grand theft AI


🔗 a linked post to theverge.com » — originally shared here on

We’ve seen a lot of AI giants engage in questionably legal and arguably unethical practices in order to get the data they want. In order to prove the value of Perplexity to investors, Srinivas built a tool to scrape Twitter by pretending to be an academic researcher using API access for research. “I would call my [fake academic] projects just like Brin Rank and all these kinds of things,” Srinivas told Lex Fridman on the latter’s podcast. I assume “Brin Rank” is a reference to Google co-founder Sergey Brin; to my ear, Srinivas was bragging about how charming and clever his lie was.

I’m not the one who’s telling you the foundation of Perplexity is lying to dodge established principles that hold up the web. Its CEO is. That’s clarifying about the actual value proposition of “answer engines.” Perplexity cannot generate actual information on its own and relies instead on third parties whose policies it abuses. The “answer engine” was developed by people who feel free to lie whenever it is more convenient, and that preference is necessary for how Perplexity works.

So that’s Perplexity’s real innovation here: shattering the foundations of trust that built the internet. The question is if any of its users or investors care.

Well, I sure do care.

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I Will Fucking Piledrive You If You Mention AI Again


🔗 a linked post to ludic.mataroa.blog » — originally shared here on

Consider the fact that most companies are unable to successfully develop and deploy the simplest of CRUD applications on time and under budget. This is a solved problem - with smart people who can collaborate and provide reasonable requirements, a competent team will knock this out of the park every single time, admittedly with some amount of frustration. The clients I work with now are all like this - even if they are totally non-technical, we have a mutual respect for the other party's intelligence, and then we do this crazy thing where we solve problems together. I may not know anything about the nuance of building analytics systems for drug rehabilitation research, but through the power of talking to each other like adults, we somehow solve problems.

But most companies can't do this, because they are operationally and culturally crippled. The median stay for an engineer will be something between one to two years, so the organization suffers from institutional retrograde amnesia. Every so often, some dickhead says something like "Maybe we should revoke the engineering team's remote work privile - whoa, wait, why did all the best engineers leave?". Whenever there is a ransomware attack, it is revealed with clockwork precision that no one has tested the backups for six months and half the legacy systems cannot be resuscitated - something that I have personally seen twice in four fucking years. Do you know how insane that is?

This whole article is a must read.

The main point: with any major leap in technology, there will be hucksters who purport to use the new hotness to solve all your problems.

The problem is that most organizations don't even take the time to solve the already solvable problems that exist within that organization.

New Javascript frameworks, database software, on-prem versus cloud-based server architecture, containerized systems, blockchain, mobile apps... unless you know how using these tools will solve a problem that your existing tech stack cannot solve, they're nothing more than distractions.

You don't need a garage full of tools to get a job done. Getting the fundamentals right is so much more important than making another trip down to Home Depot to buy your sixth version of a hammer.

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