John Jackson: Turning a Life Sentence Into a Second Chance

In this episode of Case Studies, Casey is joined by John Jackson; a former gang leader who rose through the ranks of one of the most powerful prison organizations before choosing a path of transformation. From maximum security yards to solitary confinement at Pelican Bay, John shares how trauma, prison politics, and the underground economy shaped his life—and how entrepreneurship helped him rewrite it.He reveals how gangs inside prison operate like corporations, complete with hierarchies, rules, and revenue streams. John breaks down the incentives that drive violence and control, while also exposing the perverse economics of private prisons. His story shows how the same discipline and leadership that once sustained chaos can be redirected toward growth and purpose.From orchestrating survival in solitary to joining an in-prison entrepreneurship program, John and Casey explore the pivotal moments that shifted his trajectory. This conversation offers a rare inside look at resilience, influence, and the possibility of change in even the harshest environments.Chapters00:00 | Welcome & setup00:18 | Why this world feels “foreign”00:42 | John’s origin story begins01:03 | First encounter with law enforcement01:20 | Taking the drug charge at 1701:35 | Four armed robberies & max prison02:21 | Siblings, loss, and isolation03:14 | Environment vs. guardrails05:40 | Probation, parole & stacked obstacles06:20 | Private prisons & perverse incentives08:10 | Cartels as local “employers”09:11 | Crime’s inevitable endgame10:14 | Why he took the fall11:12 | Acceptance as a survival need12:07 | Jail ecosystem: drugs, fights, status13:04 | Race lines and prison structure14:00 | Negotiation skills behind bars16:10 | Cutting off family to “go all in”17:10 | First robbery & the dangerous win18:00 | Dopamine, risk, and escalation19:23 | “I knew I’d thrive in prison”20:13 | The cafeteria incident & mentor21:07 | Sentencing math: stacking charges22:02 | Centinela: max prison near the border23:20 | Why jail can be more volatile24:05 | Joining the largest prison gang26:16 | Gangs as parent companies & franchises26:40 | Smuggling supply chains (incl. dirty cops)28:05 | Earning status: debts & discipline29:06 | Prison entrepreneurship (gambling, alcohol, phones)31:01 | Corporate politics—just higher stakes31:26 | Power, money, and “don’t do politics”33:08 | The written rulebook & paperwork checks33:47 | Who’s excluded—and why35:11 | Internal punishments & order36:20 | 18 years inside: the ladder37:01 | Pelican Bay & four years in the SHU39:20 | Solitary reality vs. myths41:27 | Transfers, levels, and riots42:36 | Use of force: towers & rifles43:06 | The peace treaty & hunger strikes44:09 | “Yard time” myth in solitary44:40 | Breaking point: wanting to go home45:01 | New charges from inside48:23 | Stepping down from leadership49:14 | A lifer’s blessing to leave50:09 | Entrepreneurship program that changed everything51:25 | His future wife: VC to prison reform52:21 | Scaling Defy & big-name allies52:42 | A force of nature walks into Pelican Bay54:10 | She saw potential—before he did Hosted on Acast. See acast.com/privacy for more information.

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