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Internet Culture Media Startups

Day 1593 and American Curiosity

I’m not sure exactly how to characterize Doomer Optimism other than a kind of social club for Internet denizens that wish to retain their optimism in the face of chaos and change. It’s a very human group and I’ve enjoyed their company for years.

And as humans tend to do, the social circles that are part of this loosely defined group meet up in person for events including a family camp out and conference called Man and the Machine. It’s been held in Wyoming thanks to the hospitality of Paul McNeil of the Wagon Box.

I’m one of the odder congregants in this group which includes a diverse array of characters from all classes and walks of life. I say I’m the odd man out only because I’ve seen them as a generally regenerative self sufficient localist group that in another era would have been back to the land hippies, unionists, environmentalists and anarchists. Generally left wing coded but skeptical of state and corporate power.

That I’m one of a handful of practicing technologists that participates, and a libertarian, means I argue for the liberatory power of open source software and its range of applications for individuals to enable a life that can provide means and meaning without being in the jaws of the Machine.

Decentralizing technologies lets us all participate. More individuals are interested in thinking how they engage with industrial processes. 3D printing enables many types of freedom and is crucial to the right to repair movement. Which gives power back to the owner of property and not the corporation from which it was purchased. I unabashedly support the freedom to compute as a human who wishes to find a harmony with the machine in all its forms. Be not controlled by your tools or their makers. Make your own future.

If none of this strikes you as particularly right wing, reactionary or otherwise populist, or even statist; I’d agree with you. I am a libertarian.

And yet there are those who are still enthralled by old narratives of political poles that this individual, and choice centered, politics is one grounded in real people with real problems not financial or social abstractions.

I was disappointed to see that our host Paul McNeil got a note from freelance journalist at the Guardian that was not intending to engage in a good faith dialogue on this community. A value that I know Paul holds dear as I’ve seen him disagree strongly with many an intelligent and capable man.

Paul is a neighbor, a friend, and a gentleman in the most noble possible sense. He does not traffic in status or social cachet. He is a free thinking and curious American man who is dedicated to hearing a large swathe of perspectives. He wrote a response and included the email screenshot below. I am certain Paul really does mean his hospitality genuinely.

Dear @awinston

Thank you for your email (below). Of course its intent was not in good faith nor was it evidence of genuine curiosity, but it did cause me to reflect on the scope of @thewagonbox project and the growing constellation of characters around it. And I had to think about you, and Mr. Wilson, and how one should respond to the sort of witch hunts for political wrong-think that have become your cottage industry (one that I’m afraid is dying.)

To your first point: an interesting aspect of the Wagon Box, and particularly our Doomer Optimism events, is the breadth of the politics represented. Seneca Scott is a ‘90s democrat who wants a safe community for his family and goats. James Pogue, like me (and Jesus), has anarchist sensibilities, cares about the habitat for the trout he fishes and is leery of the global hegemonic machine. Ashley Fitzgerald is a suburban mom who likes regenerative agriculture and healthy neighborhoods. The event has largely focused on a suspicion of “The Machine” and ways to live humanely and harmoniously with the natural world. The idea that it is some hotbed of “hard/far right” ideology, or that we are promoting “corporate governance” is laughable.

To the question of the “ties” I have to Ryan Payne, or Jonathan Keeperman, or D. C. Miller, or any other person you may see as a “smoking gun” evidence of nefarious ideology, I have a few comments. First of all, you have left out other characters who have graced the Wagon Box, some of whom you might even consider even worse! And of course there are others hard to place politically, like Walter Kirn, Patrick Deneen, Paul Kingsnorth, or Max Foley. All these characters differ quite widely, have deep disagreements, but all have something in common: I find them interesting and care about what they have to say, and they see enough in me to take me up on my invitation.

You ever get to talking to someone and you see their eyes glaze over? They do not care what you have to say, they are not listening. It’s no fun. It is death. What’s the point? Good faith curiosity is the lifeblood of any relationship, of any conversation, of journalism, and of self governance. There are swaths of folks who have had good faith curiosity driven from them, and it has been done largely by people like you, who paint in caricatures and come to stories with an agenda, who live on fear and suspicion. You send a guy like me some sort of hostage note instead of an invitation to a real conversation. It’s sad.

At the root of the Wagon Box project is my personal curiosity in people, and at the root of that is a conviction that we will all be together eventually at a large table in a conversation that will never end. Our enemy is no person, but the stale impulse of death that preys on love, on connection, on community. It thrives in the Machine of mass delusion of which, regrettably, The Guardian is a mouthpiece. It has forced you to have a narrower view of people, a static view, and one that lacks curiosity. But I really do care about you, as you too are on a journey and I’d love to hear about it. Let’s grab coffee and talk sometime. No deadline.

I brought up the context of there being technologists as part of this conversation as another reporter who shares a similarly slanted lens who seems to have quite a problem with Silicon Valley while not really understanding the core values that technologists share that are not compatible with a controlled statist or even corporatist view of power.

We are going through a huge cultural change that will sweep many of us up its cascading consequences. We will have materially different conditions as artificial intelligence changes day to day life.

Do you want to trust those who insist on control to prevent horrors? Or do you want to trust yourself and your fellow man to engage with one another as human? I’ve chosen optimism. I believe we can build freely.

Categories
Culture Internet Culture Politics

Day 1588 and American Pope

I am not a Catholic (though I am a Christian) so participating in the ambient excitement of welcoming the newly chosen Pontiff feels like it shouldn’t be allowed. Not my pope, not my Conclave right?

And yet I’m I am drawn in by the enthusiasm, the general spirit of joy and welcome, and, yes, the memes about ushering in the Pontiff.

As soon as the white smoke had been sent up, my group chats, media notifications and social streams went wild as we collectively learned more about the new Pontiff and his history. It was announced that Cardinal Robert Prevost would be named Pope Leo XIV.


Pope Leo XIV appears on the central loggia of St. Peter’s Basilica after being chosen the 267th pontiff of the Roman Catholic Church, at the Vatican, Thursday, May 8, 2025. (AP Photo/Alessandra Tarantino)

The details came quickly. And boy did the internet have questions (and a few answers). American Pope?! A Pope from Chicago?!

We soon learned he was a man who ministered to the poor in Peru for most of his life. He studied mathematics at Villanova. He went to seminary nearby my old university.

Blues Brothers Jokes were made as the Vatican must finish the work Francis had set in motion to modernize Vatican finances. A set financial troubles that has remained unfinished and is crucial for the pensions of the clergy.

Naturally many asked if the new Pontiff might be a basketball fan? A Knicks fan? Did he hoop himself?

Did he like Chicago pizza? He has eaten a hotdog at Weiner Circle according to Latin on their newly update sign.

The new Pontiff has a Twitter account. And boy does he Retweet some spicy stuff.

One of my girlfriends drove to see his childhood parish which is nearby her home. Chicago raised Catholics saving church finances so elderly clergy can retire in their home? I feel like I’ve seen this movie and loved it.

The symbolism of the Catholic Church and its representatives are clearly the stuff of which regular observers and semiotics scholars alike can read. Which made for an exciting day for everyone.

In the uncertain modernity we exist in the the Latin mass reassures many traditionalists but for everyone else a holy father who is relatable in interests, origin and culture brings even us Protestants a little closer to Rome.

Categories
Community Culture Politics

Day 1576 and Fight For The Future

I am saddened by the protective conservative ethos of some of our cathedral elites. I was filled with pride to hear multiple distinguished professor discuss their love of Boulder as emblematic of the kind often town we should all aspire to live in.

Boulder is a truly special town. Alas I have to question why it is that scholars with security and prestige can afford my hometown but their children’s generation couldn’t.

I am deeply saddened by the rising costs of my childhood town. We come back during the pandemic. When starting out my life twenty years ago I left my home as expenses rose.

My family didn’t own property. Regular people moved to other towns. Those who bought early fight to keep things. As they are. So only the wealthy, often conservative socially or economically, but generally institutionally secure elders own the town and no one else.

These preservation minded wealthy, either virtuous liberals or cultural conservatives want to preserve the values that created Boulder. The irony is not lost on me that the futurism of going back benefits the past entirely at the expense of the future.

But what moral or political good could there be in your perfect town and perfect conservation of certain mores if the children moved away.

You live in a garden made by weirdos and hippies and shined it into an expense that their own young cannot participate in it. Hippies and engineers produced a counter culture and turned it into a luxury good they did not uniformly pass down.

Boulder became a luxury good. I grant I could have a small piece of that. But would we flourish? Our elder elites keep their houses and smugly advocate against change to house even their own children. This change that necessary for the future their children will live in. We must be able to build for it.

I miss Boulder but I don’t miss this smug elitism of virtue. We chose to have a life where we could have a house and land and space for our lives and a regulatory climate where we could build the technology that will shape our future. I am sad it wasn’t going to be Boulder. We’ve lost Boulder to the security of the past and it’s expensive maintenance.

Bozeman is now the Boulder of the 90s. And I want to build up its future through the efforts of its industrious citizens and their ambition for building a future.

A forward thinking and growth focused governor introduced a future of building things with tools and technology and owning those benefits together. That the vision I want for Colorado and for Boulder.

Pairing his vision with two aesthetically conservative growth skeptical perspectives helps us realize the large gaps in values. And so I despair for the fact that I can never go home. So I must fight for my future. Which is I suppose what Renegade Futurism is all about.

Categories
Aesthetics Politics

Day 1575 and Renegade Futurism

I spent my day at a conference at the University of Colorado at Boulder’s Bensen Center for the Study of Western Civilization. It’s my hometown university and while I never studied there I was greatly enriched by its traditions of public and community programming. The land grant universities educated Americans like me even if we never attended them.

I suppose this is silly of me but I didn’t think an academic conference would actually be all that academic. I am used to financial forums and media shined up environments where doing the reading is sadly not a prerequisite. Academics very much do the reading. Or we said at my alma mater “that’s all very well in practice but how about in theory?”

I felt a little silly as the lone person on my panel who actually worked in industry and felt a little more acutely how absolutely unprepared our technical industry is for the task of running our elite institutions. We have on the ground knowledge and they have a very firm grasp of Hegel and Gransci. It’s a tension that has come to a head before.

And yet here our technical elite are gaining power and and a seat at the table and congratulations we’ve finished the long march through the institution. And somehow you still lost. We aren’t any closer to socialism or social justice. You know what happens in the dialect resolution next? Fascism. It’s like why pay the six figures for the degree if you don’t even read. Champagne socialists the lot of them.

But I’m also struck at just how divorced our academics are from the reality on the ground. We had an industrial class that founded private institutions that clashed with our empire elites before. How do you think we ended up with Stanford and the University of Chicago? Why do we continue this dance of institutional ownership?

And yet the cycle continues and we come up with new readings and new interpretations of how things should be optimally done. We have moral traditions and religious traditions and I’m sure this is an exhausting time to consider a new Pope so I’ll go light on my Catholic friends. Protestants just don’t understand. The future has arrived. You just didn’t notice it.

Categories
Community Politics Startups

Day 1571 and Townie Done Good

I am excited to be a panelist at an academic conference at my hometown’s university later this week.

While I didn’t attend the University of Colorado at Boulder myself, as a townie kid it holds a special place as educational institution in my life.

Their libraries lent me books, I attended events like their famed Conference on World Affairs and I made use of campus facilities from sports fields to their planetarium.

CU Boulder helped make me who I am today. Which is apparently someone who is qualified to weigh in on challenging topics in technology and culture.

The conference is called Renegade Futurism: Tech and the New Political Counterculture

Tech” isn’t like other industries. In addition to money and products, it is now a source for politicians, policy, culture, and philosophies with unprecedented influence throughout the globe. Figures like Elon Musk and Peter Thiel hardly count as mere industrialists; they function as thought-leaders and government operatives.  
 

This two-day conference gathers actors from today’s tech world–entrepreneurs, makers, thinkers, observers, and critics–to discuss the meaning of the tech counterculture, and what it might entail for the future of technology and American democracy.     

Hosted by the Bruce D. Benson Center for the Study of Western Civilization on Friday April 25th and Saturday April 26th and it is open to the community so if you are nearby please consider registering and attending.

The speaker line up is very impressive from politicians like our very own governor Jared Polis to journalists like James Pogue and entrepreneurs, operators and industrialists like myself.

My topic is first thing and the panelists are well worth being up early to learn from.

April 25th Atlas Building ATLS 100 – Cofrin Auditorium

9:00AM-10:15AM “How dissident is today’s tech?”

Technology can be a democratizing tool or a weapon of centralized authority. If those are perennial alternatives in technology’s history, which has predominated during recent years?

Panel: Michael Gibson, Jeff Schullenberger, Patrick Deneen, Julie Fredrickson
Moderator: Paul Diduch

Categories
Finance Politics

Day 1558 and Basis Point Bullying

I’ve tried not to pay too close attention to the panicked aftermath of the new tariff regime.

I don’t trade the public markets actively and we’d already made preparations in our personal financial lives for a deleveraged dollar. It seemed clear where things were headed and weakening the dollar solves a couple problems for America.

I am a free trader. I believe in open markets as the most effective means we currently have at our disposal for large scale coordination that works with human nature.

Nevertheless the allure of central planning and collectivism is hard to resist for those in power. The market will adapt and find other ways of allocating assets but the wasted energy of a crisis frustrates investors. Damming the waters only impeded flow.

Each basis point drop saves America 1 billion according to Secretary Bessent. So we’ve an incentive to nuke 30 basis points and keep yields low. And yet the 10 year is still stubbornly high.

The exorbitant privilege of Bretton Woods comes with the fears of a centralized currency managed by technocrats who must give guidance to markets without providing too many surprises.

I grew up with a significant amount of skepticism around the federal reserve and its places to hippie parents and the University of Chicago but even I never thought I’d live to see this kind of test. And I am a Bitcoiner! Maybe Silicon Valley will finally find out what bargain we have with Uncle Sam.

Categories
Politics

Day 1555 and Machiavellian Modernist

I finally decided to read James Burnham’s The Machiavellians this week. It felt appropriate what with all the tariff excitement and “Liberation Day” wish casting around mercantilism. As markets reacted and the chattering classes raised the volume it seemed like it was time to circle back on some core issues of power, realism, idealism and modernity.

The thesis of The Machiavellians, a term often associated with James Burnham’s book, revolves around the analysis of political power as inherently driven by elite rule and self-interest. The focus is on the practical dynamics of power, emphasizing realism over idealism. – Perplexity

As the Trump 2.0’s 5D chess defenders debate with the “tariffs are fucking retarded” economist and technocrat crowd it’s a good moment to contemplate if we’ve forgotten to care about the aims of a polis and whether it’s pursuing the people’s highest good.

Leo Strauss was the first critic of modernity I encountered with any weight. He saw Machiavelli as the first wave of modernity. Politics became practical tool as we lost our ambition for achieving justice, purpose and moral grounding through politics.

What good is an excellent technocracy if we only produce policies that send us careening towards charts with obscure symbolic meaning inscrutable to your average citizen? Meaning is stubbornly hard to measure.

Categories
Politics Preparedness

Day 1550 and Fools, Drunks & The United States of America

Americans are mere days away from the dreaded April 2nd tariff reveal and the mood could not be more sour.

If only America was a few good zoning reform bills further along. Then we could house 700 million more people and our Abundance bro moderate liberals would be in a better mood. Alas it’s easy dunking for most of us when Matty Yglesias weighs in late to the party

I’ve spent the last half decade preparing for a more chaotic world. How it would play out and what would be the driver was anyone’s guess.

I made plenty of bets that energy, compute, and decentralization would be the way in a multi-polar world, but I don’t want to count America out just yet. That’s why we made our last stand in Montana.

“God has a special providence for fools, drunkards, and the United States of America.” Otto von Bismarck

The amusing bit of Trump’s mercantilism is literally only he and a small band of trade administration aids actually think this is sensible economic policy. While I know a tariffs bro personally and I appreciate him as a friend they know I think this approach is dubious.

You know it’s bad when even the king of outlier events Nassim Nicholas Taleb is fretting for Treasury Secretary Bessent. Who is at least qualified to manage the a massive currency crisis.

He probably gets that whether tarifs make or don’t make sense is irrelevant: any ABRUPT introduction of steep tariffs must lead to a CASCADING & GENERALIZED price action.”

We are damned if you do not because tariffs are the wrong tool for this moment (though most of them are) but because markets like predictable things and cascading price action everywhere makes us dizzy.

Rather like the drunks and the fools mentioned by Bismarck, we’d better hope providence provides in this topsy turvy moment.

Categories
Aesthetics Politics

Day 1549 and Productive Primates

We are in a moment of narrative collapse. The elites who we’ve typically take our “consensus reality” cues from don’t know where to land in order to manage the revolt of the public and you can see the recycling of big ideas happening at a rapid pace.

If you’ve been on the internet at all recently, you were probably exposed to both Ezra Klein’s Abundance book tour and the Studio Ghibli mania using AI to turn iconic images into Miyazaki animations.

I think these two events are more related than you might think. Labor is becoming simultaneously more and less productive in the face of artificial intelligence. This naturally has consequences for power.

This progress is either “an insult to life itself” if you are Miyazaki or offers the potential to improve human productivity in ways we’ve not seen since the Industrial Revolution.

Which brings us back to the moderate state capacity liberals and Ezra Klein’s book tour. They are out in the cold politically and yet rather than produce a new narrative they’re re-heating the work of the meme movement effective accelerationism.

I’m pleased to see total narrative victory for e/acc over the effective altruists. Sustainability (or worse degrowth) has simply failed to resonate with our primate hierarchies that demand more. We want more of whatever other monkey’s have be it bananas or status.

Socialist zero sum politics encouraging sharing & collectively managing resources having been roundly beaten in the zeitgeist, the moderate left are insisting that actually public state mechanism are the best means to achieve abundance. Government is good actually.

Making the case for the state’s role in creating abundance is about all they have left while they wait for the pain of Trump’s tariff policies to kick in. The private markets not having the necessary time frames for long term planning is a perennial issue.

Even our most productive technology companies are feeling the pinch to perform immediately in the short term. Alex Danco dropped on essay on where we might be in the S-curve of artificial intelligence.

He argues that perhaps in the scaling of this infrastructure we may change our thinking around code as “the primary asset” of software companies and reorient it back to the shared labor, management and final product of the traditional corporation. Software companies were valued for capital efficiency by the markets but perhaps that constant no longer applies.

All this worry about creating abundance is a battle of who decides how we allocate future resources (which we don’t yet have) and who will receive the biggest share of power and plaudits in the process.

The fact that we can replicate aesthetics in an instant or do the document work of a dozen legal associates with a program isn’t really the issue at hand. We are worried that how we divvy up the sum of all our hierarchies is changing. Of course that worries every primate. It’s bloody stuff.

Categories
Finance Media Politics

Day 1539 and Institutional Trust

Continuing their exceptional data visualization work, the Financial Times shows how young Americans are losing trust in our institutions through a series of grim charts powered by Gallop polling. 

Gallop polling in the FT on young American’s trust

What a fun set of polling data on the day we have Tim Walz stomping around saying industry sucks. We have no future and the people who build just absolutely suck isn’t the best vibe from a vice presidential candidate. But it certainly seems to be a mood.

Why would anyone trust a system that proudly rolls out installment loans for food delivery aligned with payday schedules? The internet is making hay with the Klarna DoorDash partnership.

Decent people suggest we must protect the class of people so bad at math they would use this financial product. Well, actually…go a million nuanced credit understanders. Honestly I’ve never carried a credit card balance because I’m too afraid to do so. But some people yolo their consumption.

Abundance means we need to produce things. Which costs money. It’s hard to take say Ezra Klein’s Abundance tour too seriously when we make it impossible to finance housing but we can finance your burrito taxi. That’s not what anyone was hoping for when they gave all this power to our government. No wonder institutional trust is down.