Institute of Cryptoanarchy, Paralelní Polis
A lot of victimless crimes (mandatory insurances, drugs, taxes, etc)
A lot of government obligations/duties and restrictions for making a mutually voluntary businesses
A lot of angry people / enterpreneurs
Technical feasibility (thanks to Tor/I2P anonymization and truly anonymous cryptocurrencies, e.g. XMR, ZCash, ..)
Is totally regulated by the government (every new insurance product has to be approved by the state)
The scope of insurance is significantly limited
Always has to be 100% compliant with the legislation (even if there are absurd immoral laws)
Register your legal or physical entity to the insurance company
The insurance company should not know their real customer names until the insurance claim (even in this situation, it is possible for the insurance company to pay insurance money without the knowing of actual customer name using "trusted adjuster") - can be solved using HMAC function - during the registration HMAC is applied to the entity name using her secret chosen passphrase. The result of this hash is used as a unique insurance's customer ID.
The insurant can always prove she has been paying her insurance since the given date.
Until the insurance claim, the insurance company will not know the customer's name, but still be able to track her weekly/monthly insurance fees.
If the given entity gets a fine from the state, she can ask for her insurance claims.
She will scan her government's penalty evidence and upload/send to the anonymous insurance company (ideally encrypted with their PGP key), so they can verify the authenticity of the insurance request.
There always have to be ways how to check the authenticity of the government's penalties. Otherwise, you can generate and send fake government's penalties to all people and companies and force them to pay these fines.
If the given evidence is real, the insurant will receive money in any truly anonymous cryptocurrency
In many countries you can use "Guaranteed Electronic Signature" to make a digitally signed version of the penalty evidence issued by the government-approved notary service - the state notary service is capable to make the digitally signed version of the evidence
The digitally signed version of the penalty evidence can be easily verified by the anonymous insurance (using the public keys of the government/state CA)
To prevent situations that the entrepreneur decides to become the anonymous insurance's customer when she is already aware of the fact he will get a fine from the government the insurance companies might set multiple requirements for insurance claim, e.g.
minimum time of being insured (e.g. few months)
no previous insurance claims during the particular period
For the government, it will be almost impossible to prove that anyone is insured against any law. Neither they can reveal the given people receive their insurance money because no cash or traditional bank transfers are involved.
Government officials have limited sources to penalize all entrepreneurs; they will always choose only some "victims"
Less stupid and immoral laws mean less feasible business case of anonymous insurance companies.
Both anonymization technology and state dictatorship are always improved over time. Therefore the existence of anonymous cryptocurrencies is the only question of time.
The war of governments with anonymous insurance companies can be partially won by abolishing of all stupid regulations and restrictions most people consider to be unethical.
The anonymous insurance against wrong laws can create an incentive for many decent non-technical people to use bitcoins or other cryptocurrencies to protect their property.
The government can increase fines to kill all businesses that break any law and strictly enforces it. In the given situation, the best solution will be to move the business to a different country, or stay and pay high insurance fee.
The state simply does not have enough sources to check if all people or companies follow each law people/companies may be insured for. The situation for the state is asymmetrical with an apparent advantage for anonymous insurance companies.
To be insured against the laws is a criminal act
But is there a criminal act to provide "financial security" for a family whose breadwinner ends up in jail?
(e.g. is it legal to be insured (as a family/company) against the situation when the breadwinner is arrested for possession of drugs?). Because it is definitely moral.
Being a customer of the anonymous insurance is probably legal in case of smaller offenses and illegal in case of criminal acts