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So what would be the difference between buying insurance against downtime of a service you depend on (eg. Cloudflare) vs making a bet on the prediction market that there will be downtime? Even without these markets there is risk that the service goes down. The existence of the prediction market doesn't cause it to be possible.


The difference seems to be that it’s insurance if you’re buying protection against your own home burning down.

Versus when you’re financially wagering that your neighbor’s house burns down. (I.e whether you get paid back if the misfortune impacts you, vs you getting paid if misfortune visits someone else.)


How about Dead Peasant's Insurance, sorry, COLI (corporate-owned life insurance)? Policies that a company takes out on its employees with itself as a beneficiary, not the employee's family.

Employees were often unaware the policy exists, or only gave only vague consent buried in onboarding paperwork. Companies used it partly as a tax shelter, since the death benefits are generally received tax-free and cash value can grow tax-deferred.

It does still exist, though more tightly regulated, requiring explicit consent and only really able to be used on "extremely highly compensated employees" (executives).


Even in that case it is designed to cover the company’s cost of losing the employee including the cost of recruiting and training replacements, etc.

The better analogy would be if it was insurance for someone completely unrelated dying - like saying we will pay you if x unrelated person dies.


This is a framing that obscures rather than illuminating. Perhaps in this specific case, the prediction market bet acts as insurance (and even then, only for those market participants who are actual Cloudflare customers; many others are simply taking a bet). But the prediction market allows bets of many other kinds, many of which do not act as insurance against anything. Sports bets are the most obvious, but also election bets, bets on wars, bets on celebrities' lives, bets on show durations, bets on Jesus returning, bets on aliens existing - none of these can be construed as insurance. When the vast majority of actual bets traded on this betting market can not be construed as insurance, you can't defend the market as offering insurance.


>many others are simply taking a bet

Which can provide much needed liquidity to the market.


That's irrelevant. It's still gambling, or even worse - direct payment for successfully attacking Cloudflare's infrastructure.

The point overall is that the "prediction markets" don't act as real insurance, it's just a tangential side effect for a minority of participants.


If I have an insurable interest in Cloudflare’s uptime, I may buy insurance. If not, I may not.

(IANAL. In the US this seems to largely be a state law issue. California’s law, to my quick non-expert skimming, is really quite clear on this point.)


There is no risk to me if the rockets lose their next game. Unless I bet $100 on them winning, then a risk appears.


If you’re a Houston bar owner dependent on post game traffic, there would be risk of them losing.

There are a thousand of exchanges that have no risk on my life, but that doesn’t mean they don’t impact others.


A bar here in SF made local news for using Kalshi for just this purpose: https://sfstandard.com/2026/07/06/san-francisco-world-cup-ka...

In a similar vein, companies that run skill competitions (hole-in-one prizes, half-court shots, etc.) can and regularly do buy insurance on those events.

Under this theory, Kalshi is arguably not trading in commodities, but insurance, which is state-regulated.


These dishonest word games are silly. Insuring against what?


Insuring against loss. I just looked up the official name; it’s called prize indemnity insurance.

In the case of those “make a free throw from half court and win a car” competitions, the risk is a known value: the prize sponsor’s wholesale vehicle cost. The sponsor pays a premium for each contest, which is calculated based on the likelihood of someone winning.

This is a very well established insurance market. You as an individual can go out and buy hole-in-one insurance. It’s more popular in Korea and Japan where there is a strong societal expectation of throwing a lavish party if one hits a hole in one. Here in the States, it’ll cover a round of drinks for the clubhouse.

In the case of the bar, the Kalshi bet is functioning as an insurance policy against a potentially open-ended loss. The bar could be packed, the U.S. wins and everyone drinks the bar dry. So Kalshi is fulfilling a legitimate business role here.

But insurance is boring and highly regulated. The bar could likely have bought an equivalent policy from an underwriter in the Financial District. Or frankly from a rich regular. Kalshi wants to make insane amounts of money from degenerate gamblers, and to be immune from state regulators who are more answerable to citizens than the CFTC commissioners. Hence adopting the fig leaf of “futures contracts.”

If you thought I’m on Kalshi’s side here, I’m definitely not.


Insurance against loss due to ... paying for insurance? The language of the thing is compelling at first glance, but it doesn't actually parse. Sharing your gambling wins with patrons to attract more patrons is not insurance.


Not quite. The two cases are "team loses, everyone goes home and doesn't buy loads of drinks" in which case you get the payout from having bet (sorry, purchased insurance) on that team losing, offsetting your loss from not getting the money from drinks. Alternatively, the team wins, you lose your bet (insurance pay) but everyone gets loads of drinks and you make your money that way.


That’s the opposite bet from what the bar owner placed.


I’m not a lawyer, so I can’t give you an authoritative explanation of the difference between insurance and gambling. But I would guess one factor is that the insurance payout is somehow tied to the actual loss.

Kalshi is clearly not an insurer. But the commercial role they filled in this very specific situation is the same as a prize indemnity policy.




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