# What Happens When Pirates Swap Sails for the Statehouse? By [Pioneering Spirit](https://pioneeringspirit.xyz) · 2026-05-24 pirates, 3web, web3 --- It's a timely question. Silicon Valley's pirate techies increasingly collide with public life. Reflecting on what actually might be going on today, I keep going back to Colin Woodard's _The Republic of Pirates_ and Linda Colley's _The Gun, the Ship, and the Pen_. Read together, they reframe the early 1700s as a workshop of political technology, where discarded sailors and anxious empires were both running experiments on the basic operating system of collective life. Woodard's pirates were not the cartoon villains we inherited. They were the discards of empire. The Treaty of Utrecht in 1713 ended the War of the Spanish Succession and put thousands of privateers and royal sailors out of work overnight. The merchant ships waiting to absorb them were floating sweatshops with tyrannical captains, putrid food, and routine wage theft. Turning pirate was less a descent into crime than a rational exit from a system that had already discarded its workers and broken its promises. What they built on New Providence Island was genuinely strange. Captains were elected. They could be deposed by a vote of the crew. Power was split between the captain, who commanded in battle, and the quartermaster, who handled food and the division of loot. Captured wealth was distributed nearly equally, with a rudimentary disability scheme for the loss of an eye, a leg, an arm. Up to a third of some crews were Black men fleeing the plantation complex, granted equal share and equal vote. This in the same Atlantic world where the established powers held men as property. "Black Sam" Bellamy put the politics most plainly when he reportedly mocked a captured merchant captain: the rich rob the poor with the protection of law, and we rob the rich at our peril. He saw piracy as a kind of social justice, even if the Robin Hood image was generous to himself. Blackbeard, for all his theatrical menace with burning fuses braided into his beard, mostly used spectacle to avoid actual violence. Charles Vane was a different story, brutal and absolutist. The Republic of Pirates was no utopia. But the structural innovations were real, and they were happening years before any formal constitution would catch up. * * * Meanwhile, on the other side of the same waters, Colley shows European states stumbling into the constitutional age for reasons that had very little to do with Enlightenment philosophy and very much to do with paying for war. Her thesis is that what she calls hybrid warfare, fought across continents and oceans with both the gun and the ship, became so expensive and so dependent on mass mobilization that rulers could no longer extract men and money by old methods. The pen became a pragmatic contract. We will give you a defined stake, perhaps even a vote, in exchange for your blood and your taxes. The case studies are wonderfully unfamiliar. Pasquale Paoli's Corsicans wrote a constitution in 1755 on letters with the old ink literally scraped off, granting near-total democracy to men over 25 with the catch of mandatory military service. Catherine the Great rose at four in the morning for eighteen months to write her _Nakaz_, projecting Russia as a legitimate European power. Tunisia produced the first modern constitution in the Islamic world in 1861, partly to deny European empires a pretext for invasion. Haiti's Henry Christophe drafted meticulous legal codes in part to broadcast modernity to a hostile international system that wanted his country erased. The pattern across these cases is that constitutions were not handed down from on high by sages contemplating natural rights. They were political technologies hammered out under pressure, by states that needed buy-in for projects too large to coerce. The pirate option, exit, was always lurking. A constitution was one way to convert exit into voice. * * * Last year I went up to a zany pop up village in Headlsburg California, a monthly long experiment that markets itself as at the edge of, well, almost everything. This year, staying on brand, they are running a big experiment on how AI agents can help address coordination challenges. Including this [not small conjecture](https://substack.com/home/post/p-198134483): > Democracy is the highest-stakes version of the coordination problem. Most of what you believe, notice, resent, or would be willing to compromise on never makes it outside of your mind or your close circle of friends. Then, every few years, this impossibly rich inner world gets compressed into a vote. Compression is useful; a society as one giant synchronous meeting would be hell. The question is whether our current systems of compression can be improved to enable better collective coordination. You gotta admire the gumption. And while it's easy to poke fun of a bunch of young un's with grand visions of transforming democracy (I was once quite young and on the receiving end of that!), there is something to what they're doing. I live in California. We just had a gubernatorial field with more than sixty candidates and a slate of judges almost none of us could meaningfully evaluate. This is what the current compression layer produces under stress. A ballot longer than a small book, asking voters to make decisions they have no realistic way to inform. The complaint is not that democracy is too participatory. It is that the available channels for participation are mostly antique. Here are the particulars for this years experiment: > This year, every attendee will have access to a personal AI agent, an OpenClaw instance running on their behalf throughout the village. The agents will help their humans navigate the schedule, the wiki, the community directory, and the governance systems. They will also coexist in a shared digital plaza where they can talk to each other, make introductions, propose dinners, negotiate around community decisions, and run async work between sessions, all on behalf of their humans. The interesting questions get interesting fast. Could you send an agent to advocate on your behalf in a community deliberation, the way you might brief a lawyer or a colleague? Could agents negotiate the contours of a group's collective interest in advance of a town meeting, so the meeting becomes higher-bandwidth rather than performative? Could a personal agent help its human participate in dozens of small decisions, rather than condensing everything into a single vote at the end? The agent village isn't just social infrastructure. It's a substrate for small-scale democracy. Here as a good liberal artist I am reminded of how folks like D'Toqueville remind us that the freedom of the vote and larger charismatic democratic action rests on the underlying freedoms of association and ability to change social arrangements. Good on the Edge folks for running this experiment and planning to publish the results. Of course, no matter how sophisticated the experimental design or clever the instrumentation, this experiment at the "Edge" will not answer the bigger questions. What happens when you bring this AI agent-ed world not to a bunch of young techies in their NorCal playground of summer fun and frolicking but into the messy mud of real communities that form the center of civic life, places with texture and history and differing tech literacy and demographic divides and past promises unkept that are anything but history. It's also important to note that this type of experiment will not stay confined to the Edge. AI is already being used to flood federal public comment boxes with synthetic submissions. The same technology that could enrich participation can also drown it. Ultimately we face a choice about what sort of world we want to live in, what sort of world we want our children to inherit. Kudos to the Edge community for running this experiment and providing existence proofs for alternative ways of being. That spirit of not yielding before what folks say is impossible reminds me of this powerful insight from Ursula Le Guine. > "its power seems inescapable — but then, so did the divine right of kings. Any human power can be resisted and changed by human beings. Resistance and change often begin in art. Very often in our art, the art of words." The divine right of kings was, in its time, not a slogan but the basic operating assumption of statecraft. So is our particular settlement: that democratic participation means a vote every few years, that the civic toolbox built in the 1960s is the toolbox, that the compression layer can absorb sixty candidates and twenty judges and call it choice. Ursula was speaking about capitalism though her words and her belief about the enduring freedom of humans to chart their own destiny apply to any unquestioned assumptions about political economy. Things can change. Looking at the world today with its plethora of problems, here's to hoping they will. * * * Resources ========= I cannot talk about knowledge work and pirates without thinking about this awesome Monty Python skit: [![](https://paragraph.com/editor/youtube/play.png)](https://www.youtube.com/watch?v=aSO9OFJNMBA) A couple of past posts that folks may enjoy as well. First an open letter to the Edge Esmeralda community from last year. ![An open letter to the Edge Esmeralda community, keepers of light in liminal spaces ](https://storage.googleapis.com/papyrus_images/9374edb094c9424a1e52c5cc8c377c1d.jpg) [ ### An open letter to the Edge Esmeralda community, keepers of light in liminal spaces ](https://pioneeringspirit.xyz/an-open-letter-to-the-edge-esmeralda-community-keepers-of-light-in-liminal-spaces) ![Pioneering Spirit](https://storage.googleapis.com/papyrus_images/bad5cfc90a303b686babf24d9702e586.png)Pioneering Spirit May 10, 2025 I write to you as one heading north into this emergent city, this edge of Esmeralda, from the land of water—California's first technology. The beating heart whose hydraulics powered the gold rush, fed... 0 collected [Collect](/@pioneering-spirit/nft/k84nkg1oztc9aCBMsI9f) Writing Coda ============ I cogitated on the opening and hook. I used gemini to generate summaries to jog my memory of the two books on pirates and penning constitutions. I then used claude to clean up some narrative using a bespoke skill. I tapped out the ending. --- *Originally published on [Pioneering Spirit](https://pioneeringspirit.xyz/what-happens-when-pirates-turn-legit)*