Who protested Republicans and tech barons at Fort Mason? Pirates. Really.

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Reboot 2024, a highly-hyped tech conference, was under siege by pirates. Well, by a handful of members of the California Pirate Party, that is. 

On Sept. 4 and 5, Darren Mckeeman, a member of the small left-wing group, led a series of protests against Reboot 2024, an event that drew hundreds of attendees to Fort Mason to hear speakers discuss the rightward political shift in tech. 

The conference, hosted by the conservative Foundation for American Innovation, featured the chief of the Heritage Foundation, who vowed a Project 2028 if Kamala Harris won the election. Also appearing were  Y Combinator boss Garry Tan and Brendan Carr, senior Republican on the Federal Communications Commission. Sessions ranged from “The New Politics of Crypto” to “Artificial Intelligence and Leviathan,” and ticket prices from $250 to $10,000. 

The pirates’ goals were twofold: Disrupt the event, and draw attention to their cause.

“In San Francisco, everything is a Democratic party, and that’s not going to work,” said Rose Klein, the California Pirate Party captain. The pirates say they are supporting policies that are further left and “more idealistic” than what current politicians propose.  As of Sept. 8, the California Pirate Party is not a qualified political party in California. 

Mckeeman had been “nosing around the Pirate Party for a long time” before he connected with Klein, who took over leadership in 2021. Believing in the party’s potential as a home for “techies who like democracy,” Mckeeman, who said he currently works as a fractional CTO himself, got involved. 

When Reboot 2024 was announced, he knew he couldn’t let it happen in his neighborhood without a fight.

“Tan and his tech elite allies have pledged up to $15 million in local political races to support candidates promoting an agenda centered around increased police funding, reversing criminal justice reforms, and reintroducing the failed ‘war on drugs,’ Mckeeman charged in his press release. “These tech billionaires are not looking out for San Francisco’s most vulnerable citizens.” 

According to Mission Local’s analysis of local filings, Tan himself has spent just over $50,000 on the November election.

Protest by sea

On Thursday, the first day of the conference, the band of pirates — including Mckeeman, Klein, and national Pirate Party presidential candidate Vermin Love Supreme — didn’t even have to worry about sailing to Fort Mason. The attendees came to them. 

Mckeeman lives aboard his two boats, the Mai Tai and the Sayler, which are docked behind Aquarium of the Bay, near Pier 39. Supreme and his wife, whom Mckeeman flew out from Michigan for the event, were staying aboard a neighboring boat, owned by a freight pilot who described himself as “pirate-adjacent.” 

All were greeted by a 90-foot charter yacht pulling into their dock early Thursday morning. It was filled with Reboot 2024 attendees. 

Boats are supposed to receive permission to dock at the pier, Mckeeman explained. When the harbormaster told him that the crew of the yacht hadn’t asked to dock, Mckeeman cheerily responded: “Then I’m going to harass them!” 

As the suit-clad passengers disembarked at nearby docks, Supreme stood on land with his megaphone. Supreme, a satirist easily recognized by his gray beard and the black rubber boot he wears as a hat, has run for different alternative political parties  in various elections across the country since 1987. His platforms have included “mandatory toothbrushing laws,” “time-travel research,” and “free ponies for all Americans.” 

“I do some pretty outrageous things, at times,” the performance artist said. But his goal is to draw awareness to the real issues promoted by the parties he supports. For the United States Pirate Party, which has no official ballot access, that means government transparency, abolishing patents, and police reform, according to their platform. 

“Please be prepared to remove your pants and get ready for your full body cavity rectal search,” Supreme instructed Reboot 2024 attendees as they filed off the yacht. “Remember, it is in the name of national security, it will keep you safe from the terrorists. And it’s part of Obamacare!” 

There were some chuckles. Some even recognized Supreme, who wore a string skirt over a pair of American-flag boxers, a sequined cape, and his signature boot. 

While the pirates’ more traditional protest outside the conference venue later that afternoon never drew a large crowd — overall, there were 15 RSVPs and a handful of committed attendees  — Mckeeman said he felt the protest was a success. Passersby and Reboot 2024 attendees alike stopped to take selfies with Supreme, whom they recognized from social media, where he posts memes and videos of his public appearances. Supreme handed them fliers, which Mckeeman said he hoped would circulate through the conference as a small act of subversion. 

Klein said that although many view the pirates as “silly,” the members of the party are “more serious about care for people and about democracy” than anyone else. 

“Those guys aren’t going to remember any of the crap they heard at the conference,” Mckeeman later said. But, unless they are “die-hard cultists,” they are going to remember “a guy shouting at them with a bullhorn.” 

One day later, on Friday morning, the pirates “upped the ante.” During the attendees’ breakfast reception, they sailed around Fort Mason. “Surrender! We have you surrounded! We are the United States Pirate Party and we take issue with Reboot 2024!” Supreme yelled. 

He let up when the crew received warning that a kayak had overturned in the Bay. Mutual aid is a “no brainer” when you’re a sailor, Mckeeman later said.  Because “boat people are better than tech people,” the pirates tried to help. 

Becoming the self-described ‘Most Interesting Man in San Francisco‘

Afterwards, docked back at Pier 39, Mckeeman considered calling it for the rest of the day. He couldn’t imagine topping what the pirates had just done, he said, gazing out at the water.

“Hanging out on boats all the time makes us pretty mellow,” Mckeeman said of himself and his neighbors. Meanwhile, his dog, a comparatively high-strung Schipperke named Gracie, barked at a sea lion and trotted around the deck of Mckeeman’s boat. 

Gracie, the “Fearless Pirate Queen of San Francisco,” according to her Instagram bio, is actually from Kansas City, where Mckeeman flew to get her at the beginning of the pandemic. 

It was his first time in Kansas, and Mckeeman recalled craving food from Waffle House, a delicacy San Francisco could not offer him. The food, eaten in his hotel room to comply with pandemic restrictions, wasn’t nearly as good as Mckeeman remembered it being in Atlanta, where he grew up. 

When asked why he left Georgia, Mckeeman explained that he’d been caught hacking into a Democratic National Committee computer when he was 17. 

It was 1986, and “war-dialing” was all the rage. One day, using a program he built to scan through hundreds of phone numbers and the devices they were connected to, Mckeeman said he stumbled upon a DNC computer, which he was able to log into. 

According to Mckeeman, he eventually arrived home from a date to find his door off its hinges. The Georgia Bureau of Investigations, local police, and the Secret Service had all raided his dad’s home. As Mckeeman tells it, when the Secret Service realized the security breach was not a “Libyan plot” but rather “just a stupid kid,” he was left to answer to local authorities. 

The investigation, Mckeeman said, took almost two years. In the meantime, he attended the Georgia Institute of Technology. There was trouble to get into there, too, Mckeeman remembered as he lounged on his boat, telling stories: He and some dorm-mates had rescued a “washing machine”-sized computer, set it up in a supply closet, run a fiber cable through the steam tunnels across campus, connected it to the internet, and racked up a $25,000 power bill. 

The university kicked him out when he was eventually charged with hacking into the DNC computer, Mckeeman said. He spent nine months in jail awaiting trial — the same jail where Donald Trump had had his mugshot taken, according to the pirate — and got off with a $16,000 fine and nine years’ probation. 

When he was finally allowed to leave the state, Mckeeman said he figured his hacking experience was the kind of thing you could put on your resume in California. 

On the West Coast, Mckeeman said he had a variety of tech jobs for a series of startups, leaving when they were acquired because of his “aversion to big companies.” 

Some of the startups, he said, were successful. Others floundered. 

In 2009, Tech Crunch reported that Mark Pincus, the CEO of Zynga, a mobile game company, obtained a temporary restraining order against Mckeeman, who had been the IT director of Pincus’ former social networking sitem Tribe.net. According to Mckeeman, Pincus took out the restraining order because Mckeeman “cursed him out” over email for “ripping off” a vampire game from Mckeeman’s friend. 

In 2011, after the death of his dad, Mckeeman left the San Francisco SRO where he was living and started sleeping on his boat. 

He wasn’t supposed to. The boat was “barely livable” at the time, Mckeeman said, and sometimes he fell asleep after a long day of repairs. One cold January night, he awoke to “The Big Splash.” Then, screaming.

Mckeeman recounted the story nonchalantly: One of his neighbors, a 79-year old World War II veteran, called “Milkman” because of his habit of staying up until 3 a.m. reading a book and drinking a gallon of milk, had toppled overboard. Mckeeman pulled him out of the water and called paramedics. The following morning, the harbormaster informed him that he’d saved the man’s life, and invited him to a live-aboard berth that had just become available.

“I always seem to luck into things like that,” Mckeeman mused.

Now, Mckeeman lives across from the Jeremiah O’Brien, a Liberty Ship launched in 1943, where he volunteers as a docent. Unlike the other volunteers, Mckeeman said he was allowed to start helping with cruises right away because of the sheer quantity of “esoteric information” he had learned about the ship. 

Studying the Jeremiah O’Brien was easy, said Mckeeman with a shrug, telling this reporter that he could read 1,000 words a minute with 99 percent retention. In the first grade, he claimed, his dad was asked to find him another school because he’d “read every book in the library.” 

Mckeeman added that sometimes, hearing stories like this, people think he’s special. His response: “I’m barely making it, and I live on a boat in San Francisco.” 

Maybe, Mckeeman reflected wryly, he could try to say less “stupid shit” to rich people, like “don’t buy elections,” which “people have a problem with for some reason.” But then he wouldn’t live up to his Twitter tagline, “The Most Interesting Man in San Francisco.” 

Mckeeman added that working in tech in the city for almost two decades revealed to him the extent of the “dirty tricks” and “people trying to fuck with each other” in politics. In Georgia, racists “fly their flags,” he said. “The biggest problem here is that you can’t tell who they are.” 

The life of a pirate, it turns out, is exhausting. 

“That’s all I can stands,” Mckeeman said, quoting Popeye the sailor as he rose to grab Gracie from the deck. “I can’t stands no more.”