Imagine a bank that, by design, made everyone's password hashes and balances public. No two-factor authentication, no backsies on transfers. Welcome to "brainwallets", a way for truly paranoid cryptocurrency users to wager their fortunes on their ability to choose a good password or passphrase. Over the last decade, we've seen the same story play out dozens of times - a website is broken into, the user database is posted online, and most of the password hashes are cracked. Computers are now able make millions, billions or even trillions of guesses per second. Every eight character password you can type on a standard keyboard and every combination of five common english words could be tried in less than a day by today's botnets. Can people come up with passphrases able to stand up to that when money is on the line? Let's find out. For this talk, I will be releasing my high speed brainwallet cracker, "Brainflayer". I'll cover a history of brainwallets, safer passphrase-based wallet generation, passphrase security, in-the-wild cracking activity, and how I accidently stole 250 Bitcoins (and tracked down the owner to give them back).