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California Spent $160 Million Providing iPads to Prison Inmates, Willink Reports

Jocko Podcast · 541: Skills, Struggle, and Responsibility. With Jimmy May. · May 20, 2026
California Spent $160 Million Providing iPads to Prison Inmates, Willink Reports
Jocko Podcast
Jocko Podcast
541: Skills, Struggle, and Responsibility. With Jimmy May.
"I just saw something before we rolled in here today that California, the state of California, has spent $160 million to give iPads to prisoners. Okay, I want my $160 million back. I do not— if you are in jail, you do not get an iPad."
Jocko Willink cited a report claiming California spent $160 million equipping prisoners with iPads, sparking a broader discussion about government spending accountability. Willink framed the expenditure as emblematic of California's budget mismanagement, contrasting it with underfunded schools and infrastructure. The claim was used to argue that taxpayer anger may eventually mirror the revolutionary sentiment that sparked the American Revolution over far smaller tax burdens.

About this episode

On Jocko Podcast 541, host Jocko Willink welcomed back Navy SEAL veteran Jimmy May to discuss fatherhood, veteran transition, and the explosive growth of Beyond the Brotherhood, May's nonprofit supporting elite special operators after service. May, who served with Task Unit Bruiser in Ramadi and later commanded at multiple SEAL units, revealed that his organization has achieved zero suicides among over 60 high-risk veterans, all screened for character and provided tailored career mentorship. The conversation opened with May's reflections on parenting his 12-year-old son, detailing how he applies leadership principles—such as letting children set their own rules and build things themselves—to raise resilient, self-reliant kids. May shared LinkedIn posts he writes about fatherhood that have gained significant followings, covering topics like teaching maintenance, overcoming learned helplessness, and instilling respect without blind obedience. Willink and May also explored the origins of Beyond the Brotherhood, founded after May lost four teammates to suicide within four months of retirement. May described the nonprofit's rigorous screening process, requiring evaluations from superiors, peers, and subordinates, followed by personality assessments, medical detox from military pharmaceuticals, and one-on-one mentorship with civilian business leaders. He disclosed that his original board resigned en masse over disagreements about mission scope, prompting Willink and others to step in and fuel exponential growth. The episode also covered May's adventure company, Mayday Executive, which offers high-intensity corporate team-building experiences like spearfishing, car stunts, and firearms training. The pair discussed upcoming fundraising efforts, including a 3.5-mile New York City swim around the Statue of Liberty aiming to raise $1 million for veteran support. Willink praised May's leadership and the model's success, noting the critical importance of helping elite warfighters transition without losing their sense of identity and purpose. The conversation closed with reflections on government waste, California's e-bike safety crisis, and the enduring value of passing skills across generations.

Key takeaways

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