Tag: Chaotic Capital

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Media Politics Startups

Day 1941 and Uneven Off The Bars

It’s been such a crazy week. I don’t “feel the AGI” only because I am mired in the give and take of living in America where we still have businesses to run and a lot of regular people committed to actual civics. Progress is fast but implementation is slow.

And then above our daily lives we are actively in the middle of a kinetic war that our population is only dimly watching. The information environment being irradiated by foreign propoganda. I am astonished to read regular blatant campaigns that no one questions. I get ads for Chinese phone companies on Twitter.

It doesn’t even need to be about any of the active campaigns maybe a New York Times reader would pay attention to. Lots of regional political issues go uncovered. The impolite “nobody reads the Africa pages” is a very indelicate joke for readers of international newspapers. Americans often don’t even get them delivered.

As an example. What does an American understand about Mali anyway? I’ve got like a half dozen friends who care about French colonialism (and the sins of Nicholas Sarkozy) so it’s a niche Francophone thing. The stuff you maybe picked up from those who lived abroad.

No real tangible value there that isn’t social, but lots of Americans used to study with French families so you might be dimly exposed.

You’d be shocked at how much we’ve cut back on education in the liberal arts. Just as America has her very own Sicilian expedition we stop bothering to teach Thucydides. I’m in my Allen Bloom season.

I have been trying to keep my cool as a week of progress is just so fast in very real world situations. I am relishing the success of Valar Atomics as they continue own progress. We are going to need a lot more power to meet needs and meet them cleanly so I am honestly wishing for a boom in nuclear.

All the pissing and moaning about the ethics of artificial intelligence misses the point that we need to supply a lot more power for both consumer and defense needs so we might as well suit up. We have to manage what might happen with our physical reality. Like physics bro.

So this week was wild to watch as the labs stand off with fast releases. It’s very herky jerky the progress from OpenAI. The enthusiasm around Codex is very real even as no one entirely trusts the even management. Still it was fun to have two new models from OpenAI in a week. It’s funny how running a big startup is still largely product management.

Which sounds cute I realize. That I am charmed by progress in energy and algorithms while we test being under a kind of network attack with a very naive and easily swayed online population.

I like to think Americans are independent but we are not doing as much as we could to enable good governance. Americans have a say and plenty understand “right to compute” just as they did the “right to repair” but somenof government is actual hard power types. Did no one do any of the reading? I thought everyone was all about the Powerbroker for like a decade.

But we seem to have some real second order effect issues being missed entirely by the labs. Like maybe we are bad at politics? I know it’s a cheap shot but I spend so much of my private time as a citizen doing mop up companies whose management is under stress.

And being transactional with people isn’t very effective for revealed preferences. You can’t buy people and Americans don’t like the implication it sends about being treated like you can.

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Startups

Day 1936 and Life Inside The Jackpot or I Remain An Optimist

I did not expect to spend so much of my time on politics. Or maybe that’s the wrong word. I look being in voluntary service to American governance as my civic obligation. It can look like politics even when it’s mostly trying to be helpful to the running of our polity.

After 2016 I felt regular citizens like myself needed to recall Kennedy’s patriotic inaugural address from 1961. “Ask not what your country could do for you, but what you can do for your country.” America is a complicated place but we get a say in it. And I’d like to help people understand what I know so it might be useful in serving America in very strange times.

My mother loved Kennedy’s profiles in courage. Boomers have beautiful mythos on facing the new world together. He was the first president born in the 20th century. The social compact of America changed quite a bit then. I wonder who the first president born in the 21st century will be. Maybe it will be another young Catholic man.

The optics of progress aside, it was clear as a new generation in Kennedy’s era took on a new obligation to come together when the American experiment felt at risk. So much about who benefit from the military industrial complex rested in the transition from Eisenhower to Kennedy.

I think the context is a little different when progress feels inevitable. Our moment is scary. Though the Cold War was not primarily optimism. They experienced as many breaks with institutional trust as we do in 2026.

Tines are different but I do not think the prescription is different. We owe it to each other to embrace change together. What can we do for America?

I am not the son of a mobster nor am I a nepo-baby of America’s great cultural surplus. I wish. I’m not presidential material or Tiktok star material.

I do have some singular cultural advantages. I am a regular person from slightly unusual circumstances that happened to enjoy some upwardly mobility which let me to participate as an equal in an important transition point. I am actually rather surprised to matter at all. But I do and I intend to advocate for America succeeding together in this change.

I do take technology as a force in society seriously. I believe surplus is an amazing thing. My life is completely different than my biological history. Given how my human DNA was programmed and what I can do daily beyond that you bet I take artificial intelligence seriously. Material progress is real.

I take the physics of demand seriously. It seems like not everyone is confident we can speak to the general public about what it means that the technology industry has found a way to automate itself. It is a scary thing to say. And we begin with ourselves. It is actually our jobs that go first. If we believe it can be better on the other side of the Jackpot live like it.

And I do. I live a little further from civilization for the peace and quiet and because I am a little uncertain. But artificial intelligence’s new incredibly malleable models have changed my capacity by an order of magnitude. How wish I could have had this when I was a software and cosmetics founder.

I am a heavy user of all the hosted commercial models because they are in fact very good. I can do so much more across all the areas of life where I have to figure things out on my own.

I have health problems that are expensive and challenging. I’m lucky to be able to explore extensively the web of issue that drive having a body which has decided it must overreact. And I am in the process of fixing it. In ways that I’d never have had access to before Claude or ChatGPT. I have comfortably setups in spreadsheets and web apps and we can map years of bloodwork and experiments.

I think America is having an autoimmune reaction to the idea of automation as the end product of artificial intelligence. We sense it as a threat and it’s both terrifying in its potential but also a bit of the optimism has waned as the culture of technology fails to engage the mainstream as normal or even beneficial.

It’s the same process of making life better we have run. We took all our brain power to make our physical jobs easier. This has largely been viewed as a benefit to everyone except by strict biological determinists. Bronze Age romanticism is just that.

Thanks to progress in mathematics, we can now make knowledge that was extremely expensive to find, query, and organize as as accessible as asking an expert a good question.

Which is actually still tricky. Most Arthurian legends seem to resolve on knowing what to ask in order to receive wisdom. Knowing what to ask is not easily solved by mathematics. It’s not actually a cheat sheet but rather a powerful way to enable yourself. If you wish to take on that responsibility.

I feel I am somewhere between Hill and Valley in that I work in this world and I chose to become civically engaged. And I am concerned about where we are at. I am genuinely an optimist though as I think humans are so very adaptable. So I try to translate between the tribes who run our system and the tribe of people who make the systems run by the first tribe.

Maybe it’s be being somewhat in between that lets me be a node between the hill and the valley in America. Or as others frame it as a tripartite of Athens, Jerusalem, and Silicon Valley. I think that’s a bit grandiose only because maybe empires run on roads and plumbing but let’s not get forget that power is diffused in a network era. Every node that can route information has power.

The criticisms technology rightly takes from our body politic is that we are going quite fast. I know. I am inside the Gibsonian Jackpot with you. And I know it’s hard to believe that living through the change can be good even if we have inklings of the way life is already better right now. So we have to work together to figure it out.

Categories
Finance Startups

Day 180 and Thesis

As I see more pitches and work with more entrepreneurs I am finding it helpful to have my thoughts codified on paper. That way if you are interested in working with me you have a chance to vet me. Knowing what I want to see in a deal and what just isn’t a fit saves entrepreneurs time. So I’m going to doodle a bit on what I do and don’t like.

Chaotic.Capital has 4 key investment areas. But they are really just different levels of working with an uncertain future: at the individual level, the organization level, the systems level and the planetary level.

  • Personal Flexibility is critical when it’s harder to make long term lifestyle decisions (housing, health, children) – how do we allow people to make those decisions without anchoring themselves to place or time horizons that limit optionality. Businesses like marketplaces, preparedness, personal safety, service & product exchanges, health tech, longevity, and alternative credentials.
  • Organizational Agility is a differentiator for businesses in rapidly changing landscapes, so we invest in software and tooling that provides leverage for small teams to have a bigger impact or bigger teams to act more discretely and independently. Businesses like software as a service, cloud infrastructure, collaboration & coordination software, DAOS (decentralized autonomous organizations), automation software, and memetic and organizational aids.
  • Systemic Arbitrage opportunities are even greater in chaos. Working through systems level chaos helps individual and organizations protect against cascade and systemic collapse risk, mitigate political chaos, regulatory uncertainty, memetic crowd and mob behaviors, or medical chaos, just to name a few. Businesses like intelligence, decentralized finance tooling and exchanges, cryptocurrencies, bots & analytics.
  • Climate or planetary risk is an existential risk that is already fucking with our world – we like companies mitigate the chaos of climate change while profiting on the risk. Businesses like mobility, insurance, green tech.

What I don’t like to hear are pitches for things that are tangentially related or a forced connection. Sometimes folks will try to get us excited about a problem they’ve already solved and are scaling but we are looking for longer time horizons. There are plenty of amazing startups that have great returns but aren’t a fit for us. We really do want the crazy weird stuff that is going to take a while.

We don’t need you to know where you are going. We want to see ten or twenty year out timelines. What would life look like without school? How about a world where we didn’t pay taxes based on our geographic location. How about a world where we automate how our attention is allocated. Or a world where our financial power isn’t rooted through centralized trusted powers. We want 1000x leverage on change.

I’ll write more later this week about the types of companies I don’t want to invest in. Not because I don’t like them but because they just don’t match what this fund is meant to do.