Libertarian Office Seeking As Political Pickup Artistry

Around the country, hundreds of Libertarians seek office each year. Most are walking red flags.

If you’ve never experienced the genre of online pickup artistry videos, you’ve been living right. Perhaps the least painful way for a normal person to experience such a thing is alloyed by the Jane Goodall-like presence of Louis Theroux in his recent Netflix documentary, Inside the Manosphere.

Theroux, for much of its run, breezily sways between gentle interlocutor and stunned-silent observer to the steady stream of nonsense spouted by the doc’s featured influencers. This includes ride-alongs with self-described pickup artists Harrison Sullivan (who goes by HSTikkyTokky online) and Ed Matthews as they “drop game” in the streets of Marbella, Spain.

“Dropping game,” in this context, seems to be the process by which perfumed, muscle-shirted men shove phone cameras in the faces of young women while mistaking their momentary confusion at being approached and hesitation at being filmed for serious consideration of romantic involvement, and misunderstanding their eventual and inevitable polite refusals as interest.

“You alright, darling, having a good night,” seems to be the beginning and end of many interactions, taking on a rapid-fire staccato only partly attributable to the edit. This approach is purely quantitative.

Daryush Valizadeh, popularly known before his withdrawal from public life as Roosh V, emphasized this numbers-over-quality approach to engaging with women in his confidence-inspiringly titled 2011 book, Day Bang: How to Casually Pick Up Girls During the Day:

That should come in the form of at least ten approaches per week. This means you have to schedule at least a two-hour block of time every week just for day gaming. Like any other hobby, you need to put in time to improve.

Advice like this simultaneously sets men up to fail and provides them the narrative justification to continue on failing. You have to fail to improve; more attempts will eventually mean more successes.

“The law of the universe,” Valizadeh writes, “is the more you try, the more you get.”

Back on the streets of Marbella, Matthews was putting in the reps.

“We’re actually finding the most tartiest [sic] outfits,” he says to a bikini-clad beachgoer trying her hardest to ignore him, “I think you’re competing here, darling.”

I can’t think of an approach to women more different to my own (I’m happily married to a beautiful woman I’ve known most of my life. Our courtship began when we were both 17, and we’d known, respected, and enjoyed each other’s company already as friends for years prior), but the narcissism innate to the human condition does cause my mind to leap to a parallel to this behavior that lies well within my lived experience – Libertarian office seekers.

Like pickup artistry, the Libertarian approach to running for office is a low-hit-rate numbers game. Like pickup artists, most Libertarian candidates are actively off-putting to precisely those they are seeking to woo.

First some credentials. During my time as a paid staffer for the Libertarian National Committee, thousands of Libertarian candidates sought office, efforts I engaged with in a variety of ways ranging from assisting with back-office tracking and data collection to providing direct support. As national Executive Director for the Libertarian Party from 2020-2022, I led national staff through a time that saw hundreds of Libertarian candidates attain office, reaching a record number of Libertarian elected officials during my tenure that remains, to my knowledge, the party’s high-water mark in that regard.

During the 2024 presidential cycle, I had top-level roles in two different Libertarian presidential campaigns (serving as national chair of the exploratory committee for one, and later a senior campaign advisor for another). I also helped found my local county party, and engaged personally in innumerable grassroots Libertarian recruitment and petition drives (more, perhaps, on the ways in which Libertarian activism tends towards becoming a totalizing influence on one’s life in a later article).

This is all to say that I personally know both that exceptions exist to the generalizations in which I’m about to engage and how few and rare those exceptions actually are.

Libertarians never win. That was always a frustrating narrative when working Libertarian campaigns. One reason is that it’s simply not true. Even discounting Libertarians who manage to slide into a wide array of uncontested offices (a gimmick one only has access to with regard to offices no one cares about anyway), when a Libertarian runs a serious campaign for low-level office with rough parity of effort and expenditure compared to the other candidates, they win between a quarter and a third of the time. That’s pretty good – but that’s not most Libertarian campaigns by a long shot.

Most Libertarians run for offices they are unqualified to hold, have wildly insufficient resources to seek, and for which their personal skills are severely underdeveloped to campaign. Moreover, they often either do not care or cannot comprehend how their efforts are perceived. This is true both of the party strategically and of individual campaigns tactically.

Strategically, the Libertarian Party as a whole has often embraced a quantity-focused approach to candidate recruiting. You have to be in a race, after all, to benefit from some fluke that might push you out of obscurity and into relevance. When I joined staff, leadership had set a target of recruiting 2,000 candidates nationwide. Where? In what races? Were there 2,000 identified contests seen as winnable? No. The goal was bodies. The more Libertarians who run, the more Libertarians who will win.

The problem with this is the same as that with Daryush Valizadeh’s advice to aspiring pickup artists. Success in love and politics is not the same as success in sales. In a high-pressure sales team, the nominal number of deals closed is all. In other pursuits, success rates matter.

There’s a big difference between a man who hits on 1,000 women and finds only two who are interested, and another man who asks two women out and they both respond positively. Both men have gotten two dates over that same time period, but they’ve adopted very different approaches and built very different reputations. The latter is likely respectful, charismatic, and creates an environment where the women he interacts with feel good. The former’s a loser.

In the same way, when the Libertarian Party fields thousands of candidates to win dozens of offices, they sacrifice their success rate on the altar of raw numbers. Like pickup artists, they, too, have adopted in advance the narratives necessary to reinforce this approach even in the face of repeated failures. The huge class of Libertarian losers each cycle is primed to feel that they’ve helped spread the word about the party, build their own name ID, and be ready for next time.

“As Libertarians, all of your campaigns are part of one, big national effort to grow the party and spread our message,” I used to say on election night livestreams to thousands of candidates and activists who I knew were about to have a short, losing night, “every victory we announce tonight is a shared victory for us all to celebrate.”

The message those thousands of losing campaigns sent to voters was very different, though: Libertarians are losers.

That’s a message likely reinforced by the activities of the candidates themselves and their campaigns.

Campaigns are won not on raw vote totals, but on ratios. If I told you a candidate for state legislature got 1,696 votes, you couldn’t tell me if he won or lost. If I tell you instead that he got 53.6% of the vote, you know that he won.

Most Libertarian candidates convince themselves, however, that raw numbers matter. It’s an approach fostered by desperation and inadequacy. With too little time and money to run serious campaigns anyway, the mindset shifts to be like that of the pickup artist – the more voter interactions I have, the more votes I’ll get. If the default assumption is that a voter’s answer is, “no,” I can only gain by engaging them.

This isn’t how serious campaigns think, of course. A serious campaign knows it’s going to engage every voter multiple times, and views success or failure as riding on how to ensure a majority of those interactions are positive for the voter. In other words, serious campaigns are qualitative.

The quantity-over-quality mindset of Libertarian candidate culture rears its head here, too. By expecting rejection and playing the numbers, Libertarian candidates blind themselves to how off-putting their approaches actually are. If you go out and talk to 100 people and find two of them who respond well to your message, you are not two people up. You’re a net 96 people down.

Libertarian philosopher, activist, and communicator Michael Cloud coined a term for how many Libertarians communicate: “the Libertarian Macho Flash.” As far back as 1978, be began documenting cases of Libertarians campaigning with messages like “Fuck the State,” “Abolish Social Security,” and that old favorite, “Taxation is Theft.” These positions, while doctrinally pure amongst Libertarians, shock, offend, and (most importantly for a campaign) lose most voters. They attract attention, but repel people.

I acknowledged earlier rare exceptions. The example above of 1,696 votes winning a state legislative race with 53.6% of the vote is one of them. Those are the real results of the 2020 election of Libertarian Marshall Burt in Wyoming’s 39th House District. He, with extensive party support, achieved them by eschewing the political pickup artistry and building instead a real relationship with voters.

For every Marshall Burt, though, there are hundreds of Libertarian candidates each year out there “dropping game.” They routinely bring in four, six, ten times as many votes as he did, which, in congressional, senatorial, or gubernatorial contests around the country, amount to a one to two percent share of votes overall. They lose embarrassingly, and feel no shame.

After all, there is recognition and status that they receive. It doesn’t come from the ostensible targets of their pickup artistry, but from their own in-group. Ed Matthews found himself intermittently mobbed on the streets of Marbella, not by throngs of women overcome by attraction, but by young, male fans who recognize him from social media. Libertarian candidates, too, become heroes not to the voters they nominally court, but to an insular movement conditioned to heap them with plaudits at every opportunity.

In that sense, the original mission is lost, and the praise itself becomes the reward. Hit that grindset, and then get that bag. Everything outside the bubble fades.

Not all attention, however, is good. There’s a strong case that even many of the avid followers of prominent pickup artists and other manosphere influencers do not hold them in high regard. The term “lolcows” comes to us from the slang of the early Internet to describe such figures who, often oblivious, draw large followings of people who see them as humorous and embarrassing figures of derision.

Libertarian candidates, operating at a severe attention-economy deficit, are often excited at every mention of their campaign, just as, more broadly, Libertarians routinely buzz with excitement at any mainstream attention paid to the party or movement. A sense that any attention at all can be converted into forward momentum overrides any concern over whether said attention is motivated by positive feeling.

In 2017, libertarian-leaning Republican Thomas Massie, reflected on the failure of the libertarian Ron Paul movement to mobilize in 2016 in support of Paul’s son, Rand. “They weren’t voting for libertarian ideas,” he said, “they were voting for the craziest son of a bitch in the race.” He could easily have said they were voting for the biggest lolcow.

Libertarians could have taken that as a wakeup call, a chance to get better instead of crazier. Instead, Libertarians have spent the last decade doubling down. In hindsight, that’s far more consistent with the party’s culture than deep self-reflection. Clout, howsoever come by, is valued in Libertarian circles, even more highly for its scarcity there.

Back on a sidewalk in Marbella, two young women, their faces blurred presumably having refused to sign releases for Theroux’s documentary, receive an unsolicited education in Harrison Sullivan’s impressive social media following.

“Okay, listen,” he’s saying as he holds his phone, “you’re both very pretty. Give me your Instagram; we’ll do something.”

They seem polite, but it’s not clear if they actually give him any of their information. He walks away satisfied, adding as they part, “See you later, you German tarts.”