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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
Preparedness

Day 1590 and Hold Up

I don’t think most Americans are quite ready to address the comical peril of some of our logistics issues. I myself am not and I’ve been screaming bloody murder about preparedness for years.

It’s hard to imagine that any of the music is stopping when you live in a very comfortable and functional place as we do in Montana.

But I’m seeing signs of stress in all corners of our world from grid load stress to importing manufacturing equipment to the ongoing crisis in air travel. Higher end industries like luxury education and venture are doing a swift two step to hide stress but it’s there as well.

I am feeling it. My body feels it as I go through a dip of adjusting to new pressures while still existing with the old ones like my autoimmune nonsense. But I think I am holding up as well as one can.

Categories
Chronicle

Day 1579 and Marking The Days

Everyone has their own zero day for something. I’ve been writing for one thousand five hundred and seventy nine days in a row. It is 2025 Anno Domini aka the year of our Lord. It has been 100 days since Trump was sworn back into office as President.

I’m sure someone is celebrating 100 days of sobriety. I’m sure there is a couple celebrating 10 years of marriage today. A totally ordinary day in the spring likely had any number of events big and small being noted today.

We seem to like marking the passage of time quite a bit. For Aristotle fans memory is key to the cultivation of techne. We mark events in order to remember them so that they may be handed down to the next generation. We repeat so we remember.

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
Internet Culture Media

Day 1543 and Buffering in the Network

Being that so much of modern work is done online it is a challenge to ever really unplug. I feel as if startups, finance and media have it particularly bad.

I try not to let myself burn out on the dopaminergic waves of the network. But I am a citizens of the internet and just like Molly Millions I’m suffering from the central nervous system stress the Cyperpunk future promised us.

I am however going to attempt a pull back to refocus myself so that I don’t get pulled by the strong currents of the network. A lot of low roads will be traversed between here and wherever we land.

Categories
Finance Startups

Day 1542 and Future Blind

I am confident in my capacity to judge directional trends over time. I’ve been doing it consistently for close to twenty years. I’ve made solid bets that outweigh the wrong calls.

But right now I feel lost. I feel blind to short and medium term outcomes. I don’t know what happens next or in what order.

I’ve got a lot of working theories about how we orient over the next decade or two but I’ve got low confidence on anything nearer.

Perhaps this is because I simply don’t want my near term predictions to be true. They are too depressing and too cynical and too heartless.

An essay from Venkatesh Rao today titled Low Roads to High Places emphasizes why.

If a necessary historical evolution can occur via a low road or a high road, it will almost always happen via the low road.

He notes the law of the low road may simply be a an emergent consequence of thermodynamics. Entropy being what it is the path of least resistance wins.

Or maybe, as Rao suggests, the low road is a corollary to Abraham Thomas’ principle that to call macro-trends correctly you have to have “boundless optimism about technology and bottomless cynicism about humans.”

I’m just not ready to have bottomless cynicism about humans though I have optimism about technology. It’s possible to change our consensus and narrative direction and we do so regularly. Vibe shifts happen once an hour these days

Abraham Thomas has a theory that venture investing is temporal arbitrage. We are front running narrative consensus.

That’s why we look like herd animals eventually no matter how contrarian the bet was at the start.

Because being optimistic about the material changes that technology can bring has been the road to success. But I can’t decide how cynical I am able to be about my fellow humans.

Categories
Emotional Work

Day 1538 and Reason About the World

There is a pet theory that I ascribe to that precious few changes their minds without experiencing a failure in social consensus. Being pushed outside of culture lets you map it more accurately on the way back in.

There is nothing more valuable than your ability to reason about the world. We sense-make with all kinds of inconsistencies and have so little incentive to step out of what we think is true about our world. Go along to get along is how humans stay alive.

I have had a wildly inaccurate model of the world in the past and I’m confident I’ll say that same soon in the future.

But I’m comfortable falling out of social consensus if it clashes with the model of the world that I work within. I’m not saying I’m smarter than anyone but I do know that I regularly weigh my faulty priors even if it’s embarrassing. I’ll keep searching for people who can reason about the world. We can see better together.

Categories
Aesthetics Culture Politics

Day 1537 and Copy Cats

A friend of mine has managed a career as a tastemaker of the sort that hardly exists any longer. It’s hard to find a term that’s even appropriate without both identifying them and understating the power of their influence.

Influencing the direction of culture isn’t so much a job as a point of view with a paycheck. It used to be a bit simpler. We had a hierarchy of influence caped by physical realities.

Maybe your pastor or your employer influenced your daily culture. Even when I was younger it wasn’t much broader than your local news and what you could get at the library. Now we live in a mass market of influence.

Influencer, creator, journalist, editor, blogger, hell we even have Twitter accounts that move culture now. So it’s not surprising that it can be hard to keep track of who is truly influential and who is just popular.

Being heard out and being really listened to and considered are very different things. It’s a weird moment for taste. Especially culturally. We keep having vibe shifts. The people who are paid to make sense of it all are as clueless as the rest of us.

The only thing anyone can seem to agree on is that it’s all very chaotic. Which is a point of view with which I’m quite familiar. And naturally that unsettles me. Once everyone agrees on a cultural moment is exactly when the tastemakers look for something new and when the masses really come with the big bucks.

Categories
Finance

Day 1529 and The Detoxing Economy

Do you recall the first time you heard the term detox? If you were a hippie kid I’d bet you grew up with it. If you were a striver maybe it arrived in your email inbox with Gwyneth Paltrow’s Goop.

Or if you are a banker, maybe Scott Bessent introduced you to the term just this week. Which tbh I wouldn’t entirely believe as the entire dating pool for the professional upper middle class is obsessed with wellness.

“The market and the economy have just become hooked. We’ve become addicted to this government spending, and there’s going to be a detox period,”

Scott Bessent at the New York Economic Club March 6th 2025

Hippies and anxious white women usually use detox as a kind of catch all for methods of various efficacy for flushing out unwelcome…toxins. Being specific can make you sound like a loony tune.

Turns the same logic can be applied to economic and fiscal policy. If you get too far into monetary policy and the Federal Reserve you too will sound like a loony tune.

But it’s hard not to be persuaded by those who rightly point out that America has been printing money and that has downstream effects.

Many an empire has fallen for debasing its currency. Something I am sure a man like Bessent understands. It’s not so much a pleasant white girl cleanse but managing through opioid addiction. Which isn’t an encouraging metaphor.

Categories
Politics

Day 1526 and PE Owned Rump State

I’ve been trying to not explicitly discuss politics for a couple weeks as it’s hard to have any sense of consensus reality. I spend a lot of time on Twitter as well as reading news. It’s only served to further muddle my mind. I’ve regularly discuss the hostile information environment.

Given the chaotic scene it feels both foolish and necessary to send up signals to others. Venkatesh Rao has me considering cross publishing more of my general rambles to Substack. Especially as other channels become more hostile.

Rao leaves fantastic little notes like the below on whether Americans should prepare for a private equity owned rump state. A thought experiment which feels less far fetched than usual.

Just chagrined bewilderment and embarrassment and private-equity-owned rump state services shambolic-debacling along (ht Bruce Sterling for that turn of phrase). Whimpers over bangs.

As state capacity declines and social cohesion degrades it wouldn’t surprise me if the new institutional powers we trust most are corporations. Imagine Americans in twenty years as scarce but almost mythic progenitors of a corporate governance future.

Sure America may still be a nation state in that future but a United States of corporate charters isn’t all that far off from our original conception. No really check out the Virginia Company.