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It probably is legal at the moment, but the rules may be changed to make it illegal. But also Uber and Lyft were super illegal when they were invested in. To some extent, YCombinator partners are on the record[0] supporting the idea of their startups doing illegal things.

Generally they'll frame this as challenging outdated regulations, but they acknowledge that the founders whose strategies they fully support sometimes come into office hours and discuss how they're worried that the strategy puts them at risk of going to jail.

There are different kinds of illegal, and Hims/Hers may end up getting blocked from their current business model, or they may end up entrenching new ways for consumers to get affordable care. The jury is very much still out.

0: https://www.youtube.com/watch?v=Hm-ZIiwiN1o&t=8m46s

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They probably didn't, they just took the bet that this was one of the crimes that are currently legal, like crypto scams, environmental crimes, bribery, and tay evasion for the rich.
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Hims has donated $1M to the current administration, which supports this theory
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Some of the most profitable ventures this century have been objectively illegal, but when you know you won't go to prison for violating the law, why would you care to follow it?
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The process of chlorinating water was first done illegally.
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Also:

  human dissection (grave robbing)
  translating the Bible into English
  silk production outside of China (death penalty for exporting worm eggs)
  rubber production in Asia (seeds smuggled out of Brazil)
  the Underground Railroad
  heliocentrism
  AIDS treatment (see Dallas Buyers Club)
  Needle exchange programs for IV drug users
  Ridesharing/airbnb/napster (obvious ones)
  SF gay marriage licenses (in defiance of CA law)
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Translating the Bible into English was not illegal. I very much doubt Bede or the monks of Lindisfarne were breaking the law!

The same for heliocentrism. No one took Copernicus to court.

With silk and rubber the smuggling was illegal, the actual cultivation was not

Grave robbing was illegal (and still is) but dissection was not.

Needle exchange was illegal in some US states but was legal in many other countries.

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> The process of chlorinating water was first done illegally.

I tried to find a source on this but it doesn't seem to be true? The first chapter of this book describes the history of chlorination: https://upload.wikimedia.org/wikipedia/commons/f/fd/Chlorina... (which is a source Wikipedia cites) and it doesn't appear to mention anything about illegally chlorinating water. After looking in that book I asked ChatGPT to find a source for the claim, and it reported the claim was false. Chlorination was initially controversial but I can't find anything claiming it was illegal?

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The charitable assumption is that investors weren't aware it was a problem.
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