Teaching Inmates to Code with Wes Bailey


“This is a group of people who largely have been told their entire life that they’re failures – we’re going in and we’re saying ‘Hey this is just about the most complex thing that humanity has ever done, why don’t you give it a try?’ ”

Incarceration in the United States is often a punitive exercise rather than a rehabilitative one. As a consequence, recidivism is the norm – according to a 2012 report by the California Department of Corrections and Rehabilitation, just over 65% of those released from California’s prison system return within three years. San Quentin State Prison in California is challenging this issue by trying to equip inmates with valuable skills while they are incarcerated.

The Last Mile is a program that works with prisoners to help them build relevant skills in technology so that they can more easily transition to productive employment once they are out of prison. Specifically, it teaches inmates how to program, oftentimes starting at the basics like how to use a computer, and how hypertext works. In addition to the challenges of teaching students who may not know computer basics, the program has to work with the constraint of not having internet access. In this episode, Wes and Jeff discuss the realities of incarceration in the United States, and how teaching inmates how to code is a remarkably empowering way to combat and weaken the prison-industrial complex.

Wes Bailey is the Director of Program Operations at The Last Mile, and a self-taught developer.


  • How did The Last Mile get started?
  • Should everyone become an entrepreneur?
  • How does the curriculum of a coding bootcamp compare to that of The Last Mile?
  • What are the challenges to teaching programming without an internet connection?
  • Do you notice imposter syndrome in the inmates at San Quentin who are part of The Last Mile?
  • What motivates you to work on The Last Mile?
  • What lies at the root of the prison-industrial complex?


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