The envy of the failed entrepreneur

March 29, 2019 (1256 words) :: One easy trick to counter criticism of a social system: by dismissing the critics as being motivated by jealousy, rather than reason.
Tags: startups, personal, ideology

This post is day 88 of a personal challenge to write every day in 2019. See the other fragments, or sign up for my weekly newsletter.


There’s an old tweet by angel investor (and writer of fortune cookies for startup wannabe founders) Jason Calacanis. I can’t find it anymore, so I don’t remember the exact wording, but it had something to do with the idea that people who criticise Silicon Valley, or entrepreneurship, or tech more broadly, are just jealous. It’s a meritocracy, after all. They didn’t do well enough in school to get a job in tech, or their startup failed, or whatever, which means that their anger at the system is not legitimate or authoritative - it’s just personal grievances.

And you know, this is a possibility, at least in the sense that it’s not literally impossible. It’s certainly a compelling possibility. If your whole shtick is based on defending the system we currently live under, then it’s emotionally satisfying to believe that people who criticise the system are only doing so because they failed within it. You can invalidate their criticism without even listening to it, if you just remember that they must be personally motivated.

The problem with this perspective is that it’s incomplete. People can have valid criticism of a social system even if they didn’t succeed under that system. In fact, the very existence of vast numbers of people who didn’t succeed under the system may itself be indicative of its failures. In our contemporary age, without the convenience guidance of divinely established arbiters of what is “good”, we should remember that all systems for triaging people according to “merit” or “intelligence” or whatever are imprecise, arbitrary, and ultimately wrong. They are imperfect heuristics that must be continually tweaked if used at all, not treated as infallible. Why should only those who have succeeded within a system have a say in its principles? What about all those who didn’t succeed, who may have genuine insights on the system’s failings?

I’m reminded of this quote from Ursula K Le Guin’s wonderful sci-fi book The Dispossessed:

In feudal times the aristocracy had sent their sons to university, conferring superiority on the institution. Nowadays it was the other way round: the university conferred superiority on the man. They told Shevek with pride that the competition for scholarships to Ieu Eun was stiffer every year, proving the essential democracy of the institution. He said, “You put another lock on the door and call it democracy.”


I don’t really have a solid point, here. I started writing this at like 1am so I grabbed onto the first idea that flitted through my mind.

If I’m being honest with myself, my primary concern with this sort of worldview (that critics of tech/meritocracy/whatever are just failures who couldn’t hack it, etc) is very personal - that it might be used to dismiss my own work (my upcoming book, for instance). People who might otherwise be receptive to the ideas in the book will be warned away from it, because the Jason Calacanises of the world will say that I’m only criticising the industry because I’m just salty that my startup didn’t succeed.

That would suck, because as much as I might be dubious of the sort of people who still, in 2019, care about the opinions of someone like Jason Calacanis, that doesn’t mean I don’t want to reach them. Even Jason Calacanis fanboys can be critical of tech sometimes, and my ideal audience includes those who are starting to have doubts about tech, but who don’t quite have a cohesive worldview that explains those doubts. I want to build a bridge between people’s personal experiences of modern-day economic failures, and a larger theoretical framework that ties everything together from a historical perspective.

Sometimes the things I have to say are somewhat politically banal, in that they’re easy to agree with even if you don’t consider yourself a leftist (like when I complain about influencer marketing or smartphone-mediated payday loans). Sometimes they’re on the more unpopular side, because they are derived by negating ideological tenets that are often deeply-held to the point where they’re not even recognised as such (like when I say tech IPOs are bad because the stock market in general is bad).

The stuff that’s politically unpopular is, obviously, harder to argue for. When you comes across a viewpoint that seems so diametrically opposed to the mainstream perspective (the stock market is good because wealth is good, etc etc) that it seems to pose a direct challenge to deeply-rooted parts of your worldview, it’s pretty natural to raise your defenses, and start coming up with reasons to disregard it. After all, it’s much easier to disregard one ridiculous idea than it is to question a big part of your belief system.

Sometimes this is a useful tendency, which allows us to be rightly skeptical of unfounded conspiracy theories. Sometimes it’s a problem, because we end up dismissing any radical idea as a conspiracy theory simply because it feels too far-fetched. But as Noam Chomsky says in this video, sometimes there are real conspiracies, in the sense of people conspiring to bring about a particular outcome; sometimes this plotting is done in the open.

I think the conspiratorial-sounding thing that Calacanis et al don’t understand, or don’t agree with, is the way your position in the system alters your subjectivity. Which is funny, because it’s really not that radical of a concept.

I think basically everyone understands that becoming a parent, for example, will change the way you see the world - it will make you see and value certain things differently, in ways that aren’t always predictable in advance. In a similar way, having succeeded within a particular economic system (or microcosm of one), as is the case for many Silicon Valley entrepreneur/executive/investor types, will change your interests. Not always in a fully deterministic way - there’s always some room for individual agency - but there are still forces that will push you in a certain direction, which are hard to overcome. You’ll be more likely to defend the system, because you believe that it works, or at least, that it’s the best we can do, even when you become aware of its many failings. You will not be able to judge it objectively, as if from a distance, because you are in it.

If my startup had somehow done astronomically well - let’s say it had gotten bought for $50 million by like Twitter or Salesforce or something, as we used to fantasise about - would I still be making the same arguments I am now? Would I have even discovered the left? Maybe, but in all likelihood, probably not. I would be living in very different material conditions then, and my political views would have developed differently as a result.

But, you know, there are people who have achieved more success than I who share my qualms with the system. And speaking anecdotally, it feels like discontent with the system is growing, as more and more people reach a personal breaking point. So I don’t think I’m all that wrong. For me, the system isn’t bad merely because I didn’t achieve colossal success within it; the system is bad because the cost of allowing a few to succeed is borne by everyone else. It is just not a good system. Its apologists can say what they like to defend it, but the ideological basis for its continued existence seems to be crumbling. Maybe it’s time to abandon the failures of the past and come up with something better.


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