Katie Haun on the Dark Web, Gangs, Investigating Bitcoin, and More | The Tim Ferriss Show

Tim Ferriss interviews Katie Haun about her years as a federal prosecutor and her later pivot into crypto venture capital. She recounts the 'twist' of the Silk Road case in which she prosecuted two rogue federal agents who extorted Ross Ulbricht and stole bitcoin, explaining how blockchain's immutability made the convictions possible. The conversation covers prosecuting RICO cases against motorcycle and prison gangs, her mentor Will Frentzen, and her approach to building rapport with witnesses and defendants. The back half explores her education on bitcoin, NFTs, mobile payments, stablecoins, and the regulatory stakes for the US, plus personal stories about calling off an engagement and joining the Coinbase board.

• Haun explains the Silk Road was a darknet site selling everything from fake passports to heroin and fentanyl, and clarifies she prosecuted the 'twist' of the case, not Ross Ulbricht himself.
  00:09:25
• An undercover federal agent codenamed 'knob' went bad, becoming a double agent who extorted Ross Ulbricht for hundreds of thousands in bitcoin while selling government investigation secrets under the persona 'death from above'.
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• Haun states 'but for the blockchain we would not have caught' the two corrupt agents, who otherwise would still be federal agents holding over a billion dollars in bitcoin.
  00:15:36
• A second rogue agent, a Secret Service agent on detail to the NSA, stole 25,000 bitcoin from the Silk Road (worth over a billion dollars today) and framed Ulbricht's right-hand man for it.
  00:19:16
• The tip that launched the investigation came from a lawyer and former investigative journalist who warned Haun that someone on the government payroll was moving cryptocurrency.
  00:21:21
• Haun's mentor Will Frentzen held Google in contempt of federal court over a murder case, refusing to back down even when a high-up Google contact called a political appointee to undo the motion.
  00:35:23
• Haun left her entire legal career, including offers to be a judge or law-firm partner, to join the Coinbase board during 'crypto winter,' a move friends thought was crazy.
  01:36:51
• To join the Coinbase board, Haun had to withdraw from consideration for high-level government posts she was already being vetted for via FBI background check.
  01:41:29

• Ferriss regularly worked out of the Glen Park library where Silk Road founder Ross Ulbricht (handle 'dread pirate roberts') was arrested, and assumes he sat near him many times.
  00:08:22
• IRS agent Gary Alford helped crack the case by finding a reference to Ulbricht's real name on the open web via Google.
  00:14:34
• Ulbricht's right-hand man, framed for the bitcoin theft, was a grandfather living in Utah.
  00:20:18
• About 95% of federal cases plead guilty, but Haun prepared every case as if it would go to trial because you never know which will.
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• Haun used a 'reverse proffer,' bringing defendants into her office to show them a sample of the evidence against them, prompting many to plead rather than go to trial.
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• Haun first heard of bitcoin around 2012 when her boss assigned her to investigate it as a 'criminal technology' the government wanted to stop.
  00:49:50
• A LeBron James NBA Top Shot video highlight sold for $70,000, and a Steph Curry three-pointer for just over $25,000, illustrating NFT collectibles.
  01:06:52
• Haun confirms Andreessen Horowitz has disclosed holding a sizable portion of its fund in bitcoin.
  01:30:38
• Haun lives by the 'hell yes or no' rule, which Ferriss notes was coined by CD Baby founder Derek Sivers.
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• Haun says the Tim Ferriss episode with Nick Szabo (on smart contracts, using a vending machine analogy) was the first episode of the podcast she ever listened to.
  02:02:50