If you're launching an AI safety startup, reach out to me; Polaris Ventures (which I'm on the board of) may be interested, and I can potentially introduce you to other VCs and investors.

Makes sense! And yeah, IDK, I think the concept of 'measure' is pretty confusing itself and not super convincing to me, but if you think through the alternatives, they seem even less satisfying.

That leads you to always risk your life if there's a slight chance it'll make you feel better … Right? E.g. 2% death, 98% not just totally fine but actually happy, etc., all the way to 99.99% death, 0.01% super duper happy

I did some research and the top ones I found were SMH and QQQ.

I'm not sure what (if any) action-relevant point you might be making. If this is supposed to make you less concerned about death, I'd point out that the thing to care about is your measure (as in quantum immortality), which is still greatly reduced. 

Someone else added these quotes from a 1968 article about how the Vietnam war could go so wrong:

Despite the banishment of the experts, internal doubters and dissenters did indeed appear and persist. Yet as I watched the process, such men were effectively neutralized by a subtle dynamic: the domestication of dissenters. Such "domestication" arose out of a twofold clubbish need: on the one hand, the dissenter's desire to stay aboard; and on the other hand, the nondissenter's conscience. Simply stated, dissent, when recognized, was made to feel at home. On the lowest possible scale of importance, I must confess my own considerable sense of dignity and acceptance (both vital) when my senior White House employer would refer to me as his "favorite dove." Far more significant was the case of the former Undersecretary of State, George Ball. Once Mr. Ball began to express doubts, he was warmly institutionalized: he was encouraged to become the inhouse devil's advocate on Vietnam. The upshot was inevitable: the process of escalation allowed for periodic requests to Mr. Ball to speak his piece; Ball felt good, I assume (he had fought for righteousness); the others felt good (they had given a full hearing to the dovish option); and there was minimal unpleasantness. The club remained intact; and it is of course possible that matters would have gotten worse faster if Mr. Ball had kept silent, or left before his final departure in the fall of 1966. There was also, of course, the case of the last institutionalized doubter, Bill Moyers. The President is said to have greeted his arrival at meetings with an affectionate, "Well, here comes Mr. Stop-the-Bombing...." Here again the dynamics of domesticated dissent sustained the relationship for a while.

A related point—and crucial, I suppose, to government at all times—was the "effectiveness" trap, the trap that keeps men from speaking out, as clearly or often as they might, within the government. And it is the trap that keeps men from resigning in protest and airing their dissent outside the government. The most important asset that a man brings to bureaucratic life is his "effectiveness," a mysterious combination of training, style, and connections. The most ominous complaint that can be whispered of a bureaucrat is: "I'm afraid Charlie's beginning to lose his effectiveness." To preserve your effectiveness, you must decide where and when to fight the mainstream of policy; the opportunities range from pillow talk with your wife, to private drinks with your friends, to meetings with the Secretary of State or the President. The inclination to remain silent or to acquiesce in the presence of the great men—to live to fight another day, to give on this issue so that you can be "effective" on later issues—is overwhelming. Nor is it the tendency of youth alone; some of our most senior officials, men of wealth and fame, whose place in history is secure, have remained silent lest their connection with power be terminated. As for the disinclination to resign in protest: while not necessarily a Washington or even American specialty, it seems more true of a government in which ministers have no parliamentary backbench to which to retreat. In the absence of such a refuge, it is easy to rationalize the decision to stay aboard. By doing so, one may be able to prevent a few bad things from happening and perhaps even make a few good things happen. To exit is to lose even those marginal chances for "effectiveness."

There are SPX options that expire in 2027, 2028, and 2029, those seem more attractive to me than 2-3-y-dated VTI options, especially given that they have strike prices that are much further out of the money.

Would you mind posting the specific contracts you bought?

I have some of those in my portfolio. It's worth slowly walking GTC orders up the bid-ask spread, you'll get better pricing that way.

Doing a post-mortem on sapphire's other posts, their track record is pretty great:

• BTC/crypto liftoff prediction: +22%
• Meta DAO: +1600%
• SAVE: -60%
• BSC Launcher: -100%?
• OLY2021: +32%
• Perpetual futures: +20%
• Perpetual futures, DeFi edition: +15%
• Bet on Biden: +40%
• AI portfolio: approx. -5% compared to index over same time period
• AI portfolio, second post: approx. +30% compared to index over same time period
• OpenAI/MSFT: ~0%
• Buy SOL: +1000%
• There are many more that I didn't look into.

All of these were over a couple weeks/months, so if you just blindly put 10% of your portfolio into each of the above, you get very impressive returns. (Overall, roughly ~5x relative to the broad market.)