Think for yourself. Subscribe to The Free Press today: https://thefp.pub/3DmLpLi Reid Hoffman, co-founder of LinkedIn, has been a key figure in Silicon Valley since the early 2000s. Like Elon Musk, Peter Thiel, and David Sacks, he’s part of the PayPal Mafia–the network of early PayPal founders and employees who went on to become tech titans. But Hoffman’s politics have not developed like many of his peers. He has been a prominent donor to Democrats, reportedly donating over $40 million to left‑leaning groups in the past five years. After calling for the release of the Jeffrey Epstein files, Hoffman has drawn public ire from President Donald Trump, who has directed the Department of Justice to investigate Hoffman’s connections to Epstein. I sat down with Hoffman to talk about what it’s like to be in a state of anticipation of retribution by the president of the United States. I sat down with Hoffman to discuss what it’s like to live under the constant anticipation of political retribution. We talked about the alarming normalization of lawfare in the U.S., the collapse of trust in the justice system, and the way social media and AI have amplified public cynicism. We also ventured into a more philosophical discussion about the technological world he helped shape. Hoffman is clear-eyed about both the corrosive effects and the transformative potential of technology. He insists that institutions must be strengthened and invested in—not torn down, as he has seen others attempt. 0:00 — Intro 1:18 - Ad 1:49 — From Philosophy to Silicon Valley 4:44 — Technology’s Upside—and Its Turbulent Transitions 8:19 — The Vaccine Trust Crisis: Past vs. Present 14:09 — Freedom of Speech, Moderation, and Truth-Seeking Tools 19:14 — Deepfakes, AI, and the Coming Trust Battlefield 26:30 — Should Billionaires Exist? Inequality vs. Opportunity 30:37 — Envy, Capitalism, and the Dark Psychology of Redistribution 39:41— Trump, Institutions, and Democratic Stress Tests 47:39 — Political Retribution, Prosecutions, and Double Standards 58:25 — On Being Targeted by Trump’s DOJ 1:02:30 — Extremism, Antifa, and Closing Thoughts