Jack Dorsey, a Plausible Libertarian

I’ve listened to Jack Dorsey talk a few times including his discussions with Joe Rogan and Lex Friedman. Dorsey is CEO of Twitter and Square. Twitter is a revolutionary social media app and Square is a revolutionary payment processing app. Dorsey is technical in that he actually programs and he co-founded Twitter including technical code contributions. As CEO of Twitter he has been involved in controversial censorship of conservatives. This is why he was on the Rogan podcast, along with Vijaya Gadde, Twitter’s Global Lead for Policy.

I believe Gadde was essentially there to give the politically-correct answers to hot questions where Dorsey could remain silent because his real opinion would get him in hot water. I also believe Dorsey is the inspiration for Topher Grace’s character in Season 5 Episode 2 of Black Mirror.

As CEO of Square, he’s familiar with digital payment and cryptocurrency. In his Lex Friedman interview, which occurred about two months ago, he is a vocal proponent of cryptocurrency. He is clearly careful to be politically correct with his messaging, but his words are also fully consistent with a libertarian type that detests regulation, the federal reserve, non-market governance, and prefers technology as policy over government as policy. His current Twitter bio simply says “#bitcoin.”

He was raised Roman Catholic but searches on his current views come up essentially empty. The most conspicuous notes are:

  1. I can’t find any statement about the last mass he attended. This indicates he is no longer practicing. Neither can I find any credible statement of atheism or other religious inclination.
  2. He isn’t married. At his age, this also marginally indicates he is no longer a practicing Roman Catholic.
  3. He practices meditation and mindfulness along with some other Eastern and New Age practices. This is weak evidence that he follows any Eastern religious belief, however, as these practices have been effectively secularized in the US.

From an ideological point of view I consider Jack to be a technocrat more than anything else. He seems marginally spiritual but not observably theistic. He seems to favor the free market. He could be painted as a liberal, but the typical progressive liberal in the US favors regulation which Dorsey seems to detest. I see him as best described as a libertarian, although perhaps a left-libertarian. This is consistent with his financial donation to the Yang campaign and his support for UBI.

Conservatives have been claiming that Big Tech, particularly social media, has a pro-liberal or anti-conservative bias for years. While this has been contested in the past, I think the evidence has long supported the affirmative view. Here are a few reasons:

  1. Technologists are innovators by personality. This arguably leads to a natural aversion to the past and the status quo. This can lead naturally to an affinity with progressives and aversion to conservatism at a personality level.
  2. Effective technologists often interface with regulators as a major industry development phase. Regulators and policy administrators have an industrial bias to the left. Any sort of involvement by the technologist to develop regulatory policy can be characterized as a move to the left or being in bed with the government.
  3. Employees in the IT industry and the userbase of IT products, such as the Twitter userbase, are known to skew left. Conservative aversion could occur by catering to the users or by the non-malicious, accidental implementation of employee preferences. Of course, any extant user or employee malice just makes this issue even stronger.
  4. Ordinary media has a known liberal bias. Why not social media too? The explanation could lie in network effects or shared personality traits.

In case you think these conservative claims are unfounded – keep in mind that Dorsey openly admitted that there is a left-leaning bias at Twitter, and arguably in social media and American IT writ large. AEI has additional related evidence here.

For the reasons above, Dorsey would be a completely typical innovator to lean left. Despite this, it should be noted that he made special “World Leader” exceptions to enable messaging from President Trump that would otherwise be banned on Twitter. Therefore, he seems somewhat less anti-conservative than the typical innovator. Dorsey is also atypical among technologists in that he is a CEO. Politically, this places him in a pro-Republican position for non-social reasons. Practically, he plausibly understands how business and markets work in order to drive such market success at Twitter and Square, and those who best understand markets, economists, tend to support their use over intervention.

These factors add up to paint a picture of a socially left and fiscally right individual. Such an individual is called a libertarian. I’ll wrap up by arguing that IT industry elites are generally libertarian by much of the same logic:

  1. Musk, Thiel, and Bezos are all characterized as libertarians, despite their pragmatic willingness to accept government money or even engage in lobbying.
  2. Zuckerberg is described as further left due to his vocal push for regulation even above the category-standard moves on conservative censorship and favoring same-sex marriage policy. He’s also known to be Reformed Jewish which tends to be a progressive group within the US if I’m not mistaken.
    1. Yet, under monopolistic competition, the push for regulation could simply be a move to kill his competitors and improve his company value. Strangely, it could be a non-progressive business move. It is also arguably a reactionary move taken to address conservative allegations rather than a proactive move rooted in ideology.
    2. The Guardian has described Zuckerberg as libertarian and, more importantly, Zuckerberg identified himself as libertarian according to the Wall Street Journal. WSJ relevant quotation outside of paywall here.


Critical thinkers in my social network have raised a valid concern:

Dorsey donated $10 million to Ibram Kendi, which I think moves him pretty far away from libertarian. He’s pretty good on a bunch of other issues libertarians like I agree though.

Let me acknowledge that support for specific statements Kendi has made could form solid evidence of an anti-market or nonlibertarian disposition. However, I defend my thesis that Dorsey is a plausible libertarian in part by noting that Kendi disagrees with Yang here:

Dorsey has supported and donated substantially to Yang. Dorsey can hardly be taken, then, to support everything Kendi stands for or has said. Jack made a substantial donation specifically to Kendi’s anti-racism research institution at Boston University in the wake of the killings of George Floyd and Breonna Taylor. Employees at virtually every Fortune 100 company was clamoring for donations to BLM or other anti-racism initiatives, and the demand within tech has been and continues to be particularly strong.

I posit that it is an unfortunate fact beyond Dorsey’s control that BLM, Kendi’s organization, and many other anti-racism initiatives are intertwined with anti-capitalist policy and otherwise leftist policy initiatives. I also not only grant but emphatically agree that Kendi’s work has been largely counterproductive. Anti-racism research generated by Kendi seems to generally create more of the racism problem it intends to solve.

I make the below points about the donation which I think collectively defend the plausibility of the claim that Dorsey is a socially progressive or liberal individual with a conservative fiscal disposition. I continue to claim he is poorly described as an unqualified progressive or an unqualified conservative and that he is best described as a libertarian or possibly a left-libertarian.

  1. The donation could be an optical move. This could be a pragmatic move despite known negative side-effects. After all, Musk, Bezos, and Thiel all take government money, but they are still libertarians in the popular view. Anti-racism research seems to be exactly what the doctor ordered in the view of most employees, customers, and society overall.
  2. The donation could be partially rooted in ignorance or naivete. That is, it could be a case of “Jack’s heart is in the right place.” His expertise is business and programming, not racism. Maybe he hasn’t looked deeply into Kendi’s work or is trusting Kendi-favorable proxies. For all he knows, perhaps, the money would be well-spent.
  3. Dorsey may see that Kendi’s institution will be politically influential and is paying a high dollar to ensure he gets to steer the policy direction. Antiracist policy could eventually impact business and perhaps he is just out in front.
  4. Dorsey may view this as a decidedly social issue rather than a fiscal or business issue. He is arguably right to some degree. Combined with point 3, this could become a self-fulfilling prophecy.
  5. Some combination of items 1-4.
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