Every impressive person I've met shares a similar trait: they refuse to choose between thinking and building. Ask them if they are strategy or execution people, and they'll give you a quizzical look. It's a false choice. They are not one or the other, they're both.

When you look at the slate of things being built (and talked about) on social media today, you'll find the same smattering of things: a personal CRM, a travel itinerary builder, a recipe guide.

We finally received the magic wand to make anything, and we built more derivatives and declared that SaaS was dead.

Instead of exploring what is possible, we're creating (cheaper, better, faster, more personalized) copies of known objects. What a crisis of imagination.

I think of emerging technologies as a creative medium. The only way to fully understand what is possible or not is by actually building and playing with it.

Is it brittle or pliable? Is it hard or is it soft? Is it static or evolving?

So, what do you do?

Some people will say, build more and have more shots on goal. Others will say, pull back. Focus on what you should build and why. Spend more time thinking, exploring, researching, getting into the texture.

Again, these are false choices.

The best people will do both. Think deeply about what to build and why, and then quickly learn from what happens when you actually make it tangible. Then loop back.

It's not about picking one side or the other. It's about faster loops.

One list is of people she would love to hire.

The other list is of people she would love as a boss.

If you see that there are people who are on both of your lists, go find them and make some good trouble.

The thing that caught my eye was that OpenAI is planning on providing customized ChatGPT to citizens that is "of, by, and for the needs of each particular country, localized in their language and for their culture and respecting future global standards."

There's a lot baked in there.

When Anthropic worked with Collective Intelligence Project (CIP) back in 2023 on creating a collective constitutional AI, they incorporated input from 1,000 people in the US. CIP has continued this work and has launched Global Dialogues to scale this effort.

We're at an interesting moment as these models are being developed.

• How should these models incorporate values from different people?
• Is the play to have a company like OpenAI or Anthropic build single, universal models that reflect some combination of "universal" values or do we expect to see each country or region to have their own model?
• It's expensive to build and maintain your own frontier model. Will these countries look to customize open sourced models or will they look to purchase a top of the line model customized by the leading AI companies (this is what OpenAI is proposing)?
• Will we see some countries gravitate towards one model or the other - either by choice or mandate - thus in effect creating a country-model paradigm?
• But then again, is the country even the right unit to think about customization of a model? Is it geography? Language? Topic? Ethos? Something else?

These aren't just theoretical question. We're already seeing this play out today.

Earlier this year, DeepSeek (remember that?) made waves when it launched. Beyond the narrative of how it was developed (cheaper, faster), I was struck by how the model was developed to avoid certain topics. And instead of just avoiding the topic, it would strangely generate a response and then replace it with this text: Sorry, that's beyond my current scope. Let’s talk about something else. Weird.

In the design fiction piece, AI 2027, the authors position the future as US vs. China in an AI-arms race. The model landscape has consolidated into a nationalized US one and a nationalized Chinese one.

Here in May 2025, we don't have a clear winner yet and more money continues to be invested in research and development. We don't know yet what the future will look like, but I hope that it looks something like this:

Plurality of models: People should have genuine choice, not just different branding on the same underlying technology.

Models that can run locally on your machine: Critical AI tools shouldn't require an internet connection or cloud dependency. People should be able to run capable models on their own devices - whether for privacy, reliability, or simply because they live somewhere with poor internet connectivity.

Context Portability: You know the popular meme of asking ChatGPT a question baed on what it knows about you? Imagine if you could bring that context - the things that the model knows about you - with you to a different service. People don't want to be locked in.

No ads: Please don't inject ads - whether they are clearly called out or baked into the recommendations - into this. That's a quick way to destroy trust.

We're still in the early innings of figuring out how AI will meaningfully show up and shape our lives. And with each question that we answer, many more emerge.

Wild times, huh?

People

Like with most things, it starts with people. Are you working with brilliant, creative, hardworking, and kind people? It's tough to get all four at the same time. But when you do find it, it is like magic.

What

Are you working on projects that matter to you? This is highly specific to the person and will most often change. That's a good thing!

How

Are you working in a life-giving way? Whether you fall in the work-life balance camp or in the work-life integration one, it's clear that work has an outsized impact on how you experience life. Pay attention to this. Every day won't be perfect, but the aggregate should be revealing.

Learning / Growing

Are you learning and growing? Treading water can easily drain your energy and motivation. I love being in positions where I am constantly learning - about new topics, new capabilities, new technologies - and am in a position to grow and try out new things.

Valued

Are you and your work seen and valued? You can be doing some killer work, but if it isn't seen or valued, something needs to change. You shouldn't live or die by external validation, but be in a place that knows how to celebrate the wins along the way.

How you can use it

In the past, I've used this rubric to conduct regular check-ins with myself. I've experimented with answering these questions with both "Low, Medium, High" options and on a scale of 1 to 5, and I tend to like the 5-point scale. I've also used this to help assess different job options.

We're all at different points in our career and our lives, and different parts of the rubric may be more important to you than others. You may even be tempted to think about weighting these elements differently so that you can get a more "accurate" score.

Don't do it.

Don't overengineer it or overthink it.

This should be a quick, pulse check that can give you some light structure to reflect on what is and isn't going well - both at the moment and even over time.

George Box said: all models are wrong, but some are useful.

Similarly, focus on the utility of this rubric and less on the accuracy of it. Trust your gut.

The Opportunity

Imagine waking up to a message like this. One million dollars! Your mind immediately races to all the possibilities. The performing arts center desperately needs a new HVAC system. That ancient playground equipment by the elementary school has been an eyesore (and honestly, a safety hazard) for years. Maybe a scholarship fund for local students? Or why not just divide it equally among all residents?

But before any of these ideas can be debated, there's that one condition to consider: the town needs to agree on how it will make these decisions. At first glance, this might not seem like much of an obstacle. We'll just vote, right?

Then you run into your neighbor at the grocery store. "A vote? No way! If this money is for the entire town, everyone should agree on how we use it." Later that afternoon at the coffee shop, another neighbor corners you. "You know what? We should do a lottery! Put all the proposals in a hat and let fate decide." Another neighbor comes up and says, "What we need is a committee of experts. People who understand urban planning, education, and community development. Let them make an informed decision for all of us."

Ok, so maybe we won't jump to a vote just yet.

Invisible Systems

This dilemma is telling. We often jump to making decisions that we rarely step back to consider and examine the systems - the rules, rituals, and norms - that shape how they're made in the first place. Like fish questioning water, the very act of examining how we decide to decide can feel disorienting.

The recent US presidential election offers a ready example of how we simultaneously use multiple decision-making frameworks. We accept the popular vote for local measures, count the popular vote for presidential candidates, but only accept the results of the Electoral College for presidential contests. And when you realize that states have different ways of deciding the primaries - some allowing only party-affiliated voters to select from their small consideration set and others going for open primaries with ranked choice voting - you quickly realize that the way we decide things can seem quite random. Why should people in Maine have a different way of electing their candidates from people in Washington state? Then again, why shouldn't they?

In The Dawn of Everything, anthropologists David Graeber and David Wengrow argue that:

the ultimate question of human history, as we'll see, is not our equal access to material resources (land, calories, means of production), much though these things are obviously important, but our equal capacity to contribute to decisions about how to live together.

This point, that we, humans, are incredibly creative and have experimented with different ways of organizing and being and will continue to do so, is often forgotten. It's easy to assume things are the way they are for a reason. And when people do point out the invisible systems around them, it can easily fall into the trap of seeming like you're nitpicking a theoretical question and not focusing on the substance itself. We have the power to reexamine and try out new ways of making decisions together. All we have to do is look at history and around the world today to see a diverse range of these types of governance experiments.

Deciding How to Decide

When presenting this million-dollar scenario in various settings, I've noticed how quickly people jump to imagining how they would use the funds before grappling with the meta-question at hand. And I get it: it's much more fun to think of the different ways to use those funds - who amongst us hasn't daydreamed about what they would do if they won the lottery - than it is to think about how we would decide as a group.

A fairer interpretation might be that by getting specific about what we're deciding, it can help us choose how we might make that decision. Choosing what to have for dinner versus who we want as our leader have different implications for our lives. One might need a random selection and another might need more deliberation. (I'll leave it up to you to see which goes with which.)

The thing is, we have a bunch of different ways to collectively make decisions. For example, here is a starting point of different ways of making decisions:

• Majority Vote: The classic "50% plus one" approach—a proposal needs more than half the votes to win, ensuring broad support but potentially leaving a large minority unsatisfied.
• Plurality Vote: Whoever gets the most votes wins, even without a majority—simple and quick, but could result in decisions that most people actually oppose (imagine a 35% "winner" when the other 65% is split among alternatives).
• Consensus: Everyone needs to agree, or at least not actively object—it can take longer but builds stronger buy-in and often leads to more creative solutions that address everyone's concerns.
• Citizen Assemblies: A randomly selected group of residents, given time and expert input, deliberates on behalf of the community.
• Representation: Elected officials or appointed experts make decisions on behalf of others—efficient but removes direct citizen participation and can concentrate power.
• Liquid Democracy: People can either vote directly or delegate their vote to someone they trust on specific issues—imagine being able to delegate your vote on environmental projects to a local ecologist while keeping your direct vote on education matters.
• Sortition: Random selection of decision-makers from the population, like jury duty—gives everyone an equal chance to participate and can lead to surprisingly thoughtful outcomes when people are given proper support and information.
• Token-Weighted Voting: Voting power is proportional to the number of tokens each person holds—common in cryptocurrency organizations where accounts with more tokens get more say.
• Autocratic: One person makes all the decisions—the fastest option by far, and sometimes surprisingly effective (think of a skilled curator or artistic director), but requires immense trust and raises obvious concerns about power and accountability.

Unfortunately, we don't have clear guidance on when to use certain types of methods.

Why this matters

This thought experiment arrives at a moment when many people are questioning the fundamentals of how we make decisions together. From ranked-choice voting initiatives sprouting up across the United States to experiments with participatory budgeting in cities like Seattle and Boston to citizen assemblies being used in countries like Ireland and Austria and companies like Anthropic and Meta, there's a growing recognition that the how of decision-making might be as crucial as the what.

This is an opportunity to exercise our civic muscles and shape how we want to live together. And like any muscle, our ability to make decisions together grows stronger with practice. At a time when many communities feel fractured and democratic institutions face mounting challenges, we need these capabilities more than ever.

The potential impact of getting this right extends beyond just making better decisions. When communities actively engage in designing and practicing how they decide together, several important shifts can occur.

First, the process connects us to each other and to causes that matter. Working together on decisions forces us to listen to different perspectives and understand the complex web of needs in our community when deliberating together.

Second, it helps us appreciate pluralism: the idea that people can hold different, even competing, yet equally valid views about what's best for their community. There might be multiple "right" answers, and the challenge lies in finding ways to honor and sit amidst the diversity of perspectives.

Third, successfully making decisions together builds capability, confidence, and trust. Each time a community navigates a complex decision, it creates a positive feedback loop, strengthening our capacity to tackle even bigger challenges together. And when people start believing that their voice and actions matter, it can kickstart a virtuous cycle.

Looking Ahead

At this point, this is just a thought exercise to help us reflect on the meta question of figuring out how a group of people would decide how to make decisions together.

But it doesn't have to stop there.

I'd love to explore a few directions:

• Group Workshops: Bringing communities together to see how they would approach this scenario and identify what kind of information, assets, or guidance could help
• Game Development: Building simulations that let people play around with different decision-making frameworks
• Experiment: Designing studies—from controlled lab settings to real-world trials—to understand how people decide how to decide and how that potentially changes with different sets of inputs

For those intrigued by these questions of collective decision-making - whether you're interested in developing decision-making frameworks, creating simulations, or simply exploring how your own community makes choices - I invite you to join this exploration.

As we all look to the future of democracy here in the United States and beyond, I have a sense that figuring out how a bunch of neighbors can come together - and continue to come together - to solve problems relevant to them might just be the thing that can make a world of difference.

Big thank you to Joe Gerber, Becca Carroll, Debi Blizard, and Ben Koppelman for their comments and review of this note.

As impressive as these capabilities are, something about this feels off to me. Instead of building agents to interact with the internet as people currently do, shouldn't we be designing agents to interact with the internet in an agent-native way?

Websites are representations of information, and they are rendered with people in mind. That's why we have big bold copy above the fold, a clear CTA, good spacing between elements, visual elements to add interest, etc.

The thing is, the same information can be easily represented as a .txt file or as a JSON or as a RSS feed or as an API.

Instead of taking a human-centered design approach to designing websites, what would it look like if we took an agent-centered approach?

What would usability and desirability even look like in this context?

Will everything be shuffled into a renewed robots.txt file?

Will everything behave like a market?

At best, I think of these examples as stepping stones to the frontier of the new B2B - Bot to Bot - economy.

I think it's neat that agents can control the browser, but it feels like a strange ouija board experience. Do we really need to show the mouse sloooooowly moving across the screen or can we fast forward to the agent negotiating and completing a purchase of a Japanese mini truck on my behalf?

What's clear is that we're designing a way for agents to interact with our version of the internet. We'll see if they will design a way for us to interact with theirs.

On one hand, it feels like you're bashing your head against the wall because you have to make the business case for something like this. On the other hand, you can occasionally break through.

Collectively building towards "a world where our commercial systems reinforce the world we want to live in" shouldn't be radical - it should be common sense.

And remember to:

1. Appreciate the thing
2. Send the nice email
3. Put up a dang portfolio
4. Go down all the rabbit holes

And yes, the moment when the selected organization is revealed feels just like this:

Chiming in from January 2026: This has not aged well.

In our first season (2021 to 2022), we donated to eight non-profit organizations:

• Mannahatta Fund
• Fund Texas Choice
• RIP Medical Debt
• Mary's Place
• Coalition for the Homeless
• Chicago Recovery Alliance
• PASE
• Trevor Project

During our second season (2022 - 2023), we donated to 10 non-profit organizations:

• Center for Black Educator Development
• Kawerak
• Williams Institute at UCLA
• LEAP NYC
• APNA Brooklyn
• Landmine Relief Fund
• Apex for Youth
• Bronx Green Machine
• Hawai'i Community Foundation
• Hope Chicago
• Washington Douglass Chorale

We are in our third season (2024 - 2025), and we have already donated to organizations tackling a wide range of critical topics like food security, LGBTQ+ protections, civil / immigration rights, environment, and more.

Giving circles, in one form or another, have been around for hundreds of years. At its core, a group of people come together, pool their funds, and decide how to allocate the pooled capital.

This model of collective capital allocation exists across the globe with slight variations. Whether they are called ROSCAS, ASCAS, savings groups, village savings and loans associations (VSLAs), tandas, gehs, or SHGs, people come together, put their money into a collective pot¹, and decide how to use those funds. Giving circles are unique in that instead of the group's members saving or borrowing from the group, they are pooling their funds to donate to different impact causes.

There are essentially a few variables to consider:

• Pooling Frequency: How often do you pool funds? (money comes in)

• Donation Frequency: How often do you donate the funds? (money goes out)

• Selection Process: How do you choose where to donate the funds? There are typically two methods: Rotate (each member takes turns picking a cause and organization for the group to donate to) or Vote (people suggest organizations, then the group votes on which one(s) to support).

• Donation Amount: How much is each individual contributing each cycle?

Our giving circle looks like this:

• Pooling Frequency: monthly

• Donation Frequency: monthly

• Selection Process: rotate

• Donation Amount: $100 per person (and when we can take advantage of any matching funds, we do that too!)

I love our giving circle for a bunch of reasons, but here are my top three.

It's an excuse to get together with your friends and have conversations that go beyond the usual shenanigans. Each month, we learn more about different causes and organizations that matter to each person. And all too often, you see a direct link between a person's story and the cause and organization that has been nominated. When it feels like your group chats are just memes and old jokes, it is refreshing and life giving to have deeper, slower, more heartfelt conversations with old friends.

It helps you learn about causes and organizations you typically wouldn’t have found on your own. I have a hunch that more people would love to donate more and more often, but they often get stuck in not knowing who to donate to. By coming together as a group, everyone benefits from each person’s journey of selecting a cause and organization and can learn faster. The broad range of organizations that are selected is a feature, not a bug of our giving circle.

You start thinking about your own giving plan and how you want to show up as a good neighbor. Having a monthly cadence to learn about different organizations and causes establishes a great rhythm for reflection and consideration. But boy, you definitely feel a certain pressure when it is your turn to present to the group. I’ve found that this small deadline is just the right amount of pressure that I need to get over the hump of wanting to donate and be more involved to actually doing it.

I know that a lot of people want to donate more and more often, but may not know where to begin. I think starting a giving circle with a group of friends may be a great way to just get started. I guarantee that you and your friends will surprise each other. There are a bunch of resources out there, and I'm happy to help as well.

A few parting thoughts:

1. Donate to these organizations. They are all doing incredible work, and we are proud to have selected them. And for my onchain / crypto / web3² friends, you can donate to all of the organizations grouped by season (thank you Splits and Endaoment for making this so easy). For season 1, you can send funds to 0x1AB9938B1503d7EB7DD45833449C4Ea04a4B5146. For season 2, you can send funds to 0x61659C08CCcCc373C1f120B34eD31910E8C586DD.

2. Donate with us. If you'd like to donate alongside our giving circle, please reach out. We'll share how you can do that.

3. Join or start a giving circle for at least one season. It is one of those no-regret moves.

4. Learn more about giving circles. Philanthropy Together has assembled a bunch of fantastic resources.

I'd ask him every so often about how to make his kimchi stew, but he would just smile and tell me to eat up. I had looked up all of the recipes and tutorials online, but they never hit the mark. You just can't find 손맛 (son mat) online.

What did dad do to make that stew?

Perhaps it's time to just ask him. The thing is, it has been a few years since dad passed away.

Should I boot him up?

A lot of ink has been spilled to describe why one should write.

We've all heard that you should write to think. Thoughts and opinions are a lot messier than we'd like to admit and exist in a quantum state until we wrangle them down.

My friend, David Sasaki, describes his newsletter as a time capsule to remember what it was like to live in the 2020s. He offers a more reflective take and writes:

I’m doing this to prompt meaningful conversations. To foster community. To stay curious.

Henrik Karlsson writes:

A blog post is a search query. You write to find your tribe; you write so they will know what kind of fascinating things they should route to your inbox.

Winnie Lim writes:

This website is essentially a repository of my memories, lessons I’ve learnt, insights I’ve discovered, a changelog of my previous selves. Most people build a map of things they have learnt, I am building a map of how I have come to be, in case I may get lost again.

I agree with David, Henrik, and Winnie: writing is like building a time capsule, finding community, and building a map.

I've been thinking about another reason to write.

What if writing is a way to create a dataset to train a future model of yourself?

In the not so distant future, will your kids be disappointed that you didn't create a dataset that they could use to boot up an AI represenation of yourself? I know that I cherish old voicemails that exist so ephemerally on my phone because I can listen to a loved one's voice. Will people want to do something similar, but with different technology?

As they say, follow the goat paths.

If talking to an AI-version of your parents and friends becomes normalized, how will those models be trained¹?

How will this affect our ability to process and grow? Will we be able to learn and grow from the past if we can always go back to it? Will this lead to the closure we've been looking for or will this just result in a doom loop²?

What will be the new norms and taboos? Will this be more like a seance or a moving photograph from Harry Potter?

It's one thing to talk to an AI-version of Albert Einstein. It's another to talk to an AI-version of your dad. Will there be controls on who has access to these characters (people? golems? representations? simulacra?)?

One way or another, we are entering an Overton window of weirdness. Get ready for the weird and sublime.

Note: the passage about my dad is fictional and speculative. His kimchi stew is ok.

You send me your shit, we'll send you ours.

It turns out that North Korea may not be as locked down as we expected.

According to The New York Times:

North Korea’s trash balloons have provided clues to life in the isolated North, South Korean officials said. 

The cargo has included patched-up socks and discarded clothes, some with images of Mickey Mouse and Hello Kitty, despite Pyongyang’s tirade against outside influence.

While reading this article, I was reminded of Robin Nagle's work. Robin is an anthropology professor at NYU and NYC's Department of Sanitation's anthropologist-in-residence. She conducted long-term, ethnographic research on garbage, which you can learn more about in her TED talk and her book, Picking Up.

In her words:

I consider the category of material culture known generically as waste, with a specific emphasis on the infrastructures and organizational demands that municipal garbage imposes on urban areas. Within this broad perspective, I’m especially interested in the people, history, and politics that are always inherent to labors of waste, and in the many ways that the form of waste we call garbage is implicated in every contemporary environmental crisis. I also consider mechanisms of evaluation that determine how and when a particular example of material culture is defined as “trash” and the varied consequences, in many contexts, of such a definition.

Like any good anthropologist, you can ponder the universe's biggest questions with the most quotidian of things.

What does our trash reveal about us? Our values? Our visible and invisible systems?

What does our digital trash look like? We have the wonderfully quaint, skeuomorphic trash bucket and recycling bin in our operating systems, but I'd bet that people's digital "trash" is all over people's desktops, folders, and drives.

How should we reconcile the permanent ephemera or ephemeral permanence of digital objects? Do things really go away? Do things really stick around?

Anyway, countries are sending shit through the skies and air(waves). It seems that propaganda comes in many flavors.

TV programming got unbundled through streaming, only to be rebundled into Netflix, Apple TV, Hulu, Disney+, and Amazon Prime.

CDs were unbundled into MP3s and rebundled into Spotify.

Fashion from the gloriously awkward 90s are now back en vogue to the amusement of many elder millennials like myself.

I've long had a fascination with the back and forth of the pendulum. Instead of feeling trapped by the inevitable ebb and flow, I've found a certain comfort in the paradox of the inevitability of change. This, too, shall change. And change. And change.

The movement of a pendulum can be represented as a sine wave, with the x-axis representing time.

However, I've always had a hunch that unlike the mathematical representation of a pendulum, an idea moves from one end to the other on a slightly different path. Ideas have a different set of physics to them, and they come back with a certain spin that wobbles and moves as it carries along the context of the particular moment.

So instead of imagining a wave going back and forth in perpetuity, I like to think that ideas look more like spirals. Yes, they move back and forth, but they're not trapped in an endless cycle. Things still move forward and progress, propelled by each cycle's particular logic and flavor.

In the visual below, click on the animate button to see how a wave can transform into a spiral. You can also play around with the different sliders to manipulate the wave / spiral. This will make more sense on a desktop device.

But what causes this transformation?

I like to think that within a complex system of infinite, interwoven relationships of causes and effects, our creativity, ingenuity, and healthy doses of serendipity come together to create a force that opens up new possibilities and futures.

We know that progress is possible, but not inevitable. It's up to us and our collective ability to learn from the past, fiercely imagine new possibilities, and build our way forward from a wave to a spiral.

And who knows? Maybe JNCO jeans will be back in 2044. Or maybe they never really went away in the first place.

Btw, if you liked the animation of the wave transforming into a spiral, you can collect it as an NFT here.

::ducks for cover::