Quote · All-In with Chamath, Jason, Sacks & Friedberg
Dan Loeb: The Lost Art of Short Selling, and Why Stock Picking is Back
Where this was said
Criminal justice reform and the Ross Ulbricht pardon
At 25:30 · chapter starts 22:15
The episode's most surprising segment unfolds as Loeb walks through his involvement in the Ross Ulbricht pardon. He frames Ulbricht as sitting in the third category of his criminal justice taxonomy: not falsely convicted, but bearing a wildly disproportionate sentence — double life plus 40 years — for a crime that, while real, never included proven murder-for-hire charges. Introduced to the case through Reva Tez, a contact from Intel and friend of Olaf Carlsen-Wii, Loeb recognised the only path to freedom was a presidential pardon. He approached Charlie Kirk, who adopted the cause wholeheartedly and made it his sole personal ask of President Trump. A last-minute scare on the last day of Trump's 45th term — the Justice Department threatened to 'go after' Trump if he commuted the sentence — caused the commutation to be withdrawn. But four years later, Kirk pressed the case again, Trump followed through on a campaign promise to the crypto and libertarian communities, and Ulbricht received a full pardon. The twist that Loeb discovered just days before this recording: David Warrington, now White House Counsel, had been Ulbricht's personal attorney for a decade. Today, Ulbricht is married, expecting a child, and living freely. Loeb closes by describing his continuing work on individual cases through an organisation called Aleph, and his parallel fight against antisemitism. [1] — Dan Loeb "Dan Loeb was a key player in securing Ross Ulbricht's presidential pardon — approaching Charlie Kirk, who made it his sole ask of President…" 23:00
Dan Loeb was a key player in securing Ross Ulbricht's presidential pardon — approaching Charlie Kirk, who made it his sole ask of President Trump. The twist: Trump's then-attorney David Warrington, now White House Counsel, had already been Ulbricht's personal lawyer for a decade.
The wealth gap isn't about billionaires — it's about what we're not giving poor kids. Loeb, as chairman of Success Academies, argues the real culprit is union-protected school structures that strip out accountability and merit, and that proving education reform works doesn't require more money.
Loeb became chairman of Success Academies, a New York charter school network, arguing that income inequality's root cause is failing to equip vulnerable children with intellectual tools — not Jeff Bezos's wealth.
Loeb categorised prisoners into three groups: the falsely convicted, those showing contrition and rehabilitation, and those with disproportionate sentences — and argued each warrants different reform interventions.
Silk Road founder Ross Ulbricht received a sentence of double life plus 40 years — a sentence Loeb and others argued was wildly disproportionate to the actual charges proven in court.
