"Why does this keep happening?" Because the market is clownshoes, top to bottom. Users are clownshoes: they are gambling, and so they overvalue ability to move money ~instantly in and out of exchanges. This results in exchanges competing on custodial risk. The winners lose.
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There is a well-known triangle in accounting to separate controls and thereby prevent embezzlement: authority to move funds, physical custody of funds, recordkeeping. Anyone who has all three can steal all the money. Root any computer at a Bitcoin exchange. Get all three.
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The Bitcoin community's sole compensating control, the hot wallet / cold wallet distinction, is clownshoes. If it actually worked …http://dayssinceacryptocurrencyexchangehaslostmorethan100million.com/ would not need to be a domain name. It's easy to eff up and the SUCCESSFUL case is that you lose only 5~20% of all AUM.
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The exchanges are clownshoes. Probably one in the world has the security team required to secure a Bitcoin exchange. I had previously estimated that at $10 million a year but that actually might not get you there, particularly since market pressure is expanding attack surface.
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Regulators are clownshoes. In what functioning regulated market is it OK for retail to lose hundreds of millions of dollars to operational error multiple times per year?!
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"People knew about the risk." See that's the thing about regulated markets: you're allowed to sell *products* which are risky but the *system* risk should be close to zero. Do you know when the last time a bank or brokerage has lost $50 million in customer money was?
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