The Venture People's Choice

Deafening silence after Ron DeSantis' announcement suggests that VCs are becoming enmeshed in more ways than one.

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Last night, Ron DeSantis opened the lid on the worst-kept secret in politics and announced his candidacy for the 2024 Republican nomination for President — of course, not before ensuring he signed into law protecting his own ability to remain in office while campaigning. What was surprising, however, was the way he did it, as well as the response it generated.

It was surprising in a few ways, actually.

Firstly, it was announced the day prior that it would happen on Twitter Spaces, an attempt to create a claimed “rare and unscripted conversation” that tried to paint a historic tone on this event despite many candidates doing similar radio-and-television-based town halls in the past. This was allegedly an attempt to raise a middle finger wrapped in a Milton Friedman book to legacy media outlets.

What was also surprising is how much attention the abject technological own-goal the Space got as opposed to a deeper and authentic look into DeSantis’ generally horrifying political stances. There is a schadenfreude inherent in the Extremely Online crowd to see Twitter fail - which the broader media latched onto immediately after the event - yet it left those who want DeSantis’ lack of presidential fitness on a policy level to be further exposed a bit disappointed (including, admittedly, me).

But where I found myself most surprised - or, perhaps, exasperated, was the way the venture community responded.

Since 2020, tech leaders - investors, founders, and others - have vocalized their positions on various civic topics in more demonstrative ways. Perhaps the most targeted upswing in discourse has centered around San Francisco’s topsy-turvy journey through the pandemic. I don’t need to go on about the myriad “moderate” efforts that prominent investors like David Sacks, Garry Tan, and others have advocated for over the past several years — they’ve been well-documented.

Sacks, for what it’s worth, is a longtime supporter of little-c conservative efforts, so his involvement in the above campaigns, and hosting the DeSantis announcement, were of little surprise. My befuddlement is with Tan and others, whom have spent the past several years placing San Francisco’s dubiously-progressive label on a pedestal and shooting paintballs at it all while being self-proclaimed “moderate Democrats”.

It would seem, then, that if Tan and others still consider themselves slightly left-of-center, then they presumably would be quick to denounce a DeSantis campaign that expands upon his Florida culture wars, authoritarian characteristics, and general misalignment with all things liberal. Instead, last evening’s Twitter feeds of Tan, GrowSF founder Sachin Agarwal, RootVC Partner and Dean Preston reply guy Kane Hsieh, and many others rolled through another repetivie airing of grievances against San Francisco’s progressive front, the crime progressives have allegedly enabled, and the mayhem therein. One of two things are happening here: either they consider a pivot to publicly announcing their opposition to a DeSantis presidency to be off-brand or distracting, or they are choosing to endorse his campaign through silence and complicity.

I’ve formed an opinion on this, and it’s based a little bit on personal experience: it’s probably both, but more of the latter. I have proposed a slightly progressive take countering their fearmongering, and it’s been met with shunning and blocks on twitter. One owner of an Angel syndicate even removed me from his group after I pointed out that, despite being connected on LinkedIn and part of his syndicate, he had me blocked on Twitter; when I asked why, he simply said “I’ve had problems with people that think like you”. And there is not much of an indication that any of these tech leaders plan to lift much of a finger to advocate for a strong and truly united front to defeat either candidate the increasingly right-moving Republican Party selects.

My friend at Laconia, Geri Kirilova, has written extensively on the risks of enmeshment in the venture space, where she describes a system where economic tie-ups between funds creates a whole host of structural issues that benefit capital allocators while founders (and emerging fund managers) suffer. Where I would suggest we are starting to see more enmeshment is in the political sphere, where investors and founders take their marching orders from prominent investors and, at risk of being ostracized, fall in line with similar political viewpoints. I need not point out the terrible consequences of such enmeshment occurring, especially in an industry claiming to be the arbiters of future innovation.