The Last Mile – Helping to turn prisoners into entrepreneurs


I normally like to listen to podcasts (yes I still listen to podcasts) when I go for my long runs on the weekend.  One of my favorite podcasts is the Stanford University entrepreneurial thought leaders podcast.  It is an audio recording of live lectures given to some of the brightest young and aspiring entrepreneurs in Stanford’s undergraduate engineering program.  In addition to having top names come and give lectures it also often features some very thought-provoking material from the social impact space.  So I figured it might be interesting to share the story of one of the NGOs it recently featured.  The Last Mile is an entrepreneurship accelerator for prisoners in San Quentin state penitentiary in California.  It is a program designed to help ex-offenders become technology entrepreneurs.  Sounds interesting, right?  Well it has also gotten a lot of positive attention having been written up in the likes of Forbes Magazine, Tech Crunch and the Atlantic Monthly.  It also has been successful enough that they now plan to expand the program to 5 other prisons.  With a final goal of partnering with the government and technology luminaries to launch a nationwide program to alleviate the financial mess in prisons once and for all. Read on to find out more.


The Last Mile is not exactly a social business as it is not for-profit, but it is worth sharing because it is addressing a huge social problem in an innovative way.  The Last Mile is a 6-month, twice weekly program for prisoners that teaches business and entrepreneurial skills to qualified men in prison before they are released. The goal is to provide a sense of hope that they can succeed as free men and potential for employment in a paid internship in Silicon Valley or to launch their own tech businesses once they graduate and are released.  It is a concept very similar to well-known accelerators like Y Combinator or TechStars except that it takes place in one of California’s oldest and deadliest prisons – San Quentin is the only prison in CA with gas chambers.  It is also unique from other prison vocational programs in that it is selective about its participants and brings in top talent – the likes of Guy Kawasaki, Josh Kopelman and Erik Moore to give lectures.  It is unequivocal proof of how giving people the right tools and education can empower them to give back to their societies.


The Last Mile was created by husband and wife team Chris Redlitz and Beverly Parenti in 2011.  Chris had the original idea upon a visit to San Quentin prison.  He wanted to use technology for social change outside of their already  successful KickLabs accelerator program. It took him some doing but he was able to convince his wife Beverly and later the California State Department of Corrections as well as a whole slew of speakers and friends to run a pilot.  Once the pilot was a success they expanded.  They named the program The Last Mile because one of the most difficult, and often neglected, aspects of rehabilitation is the transition from inside the prison walls to functioning successfully in the free world. It is truly the “final step” to freedom.


Besides the obvious social benefit of giving prisoners a chance to return to society and lead productive lives giving back to society by learning about business, technology and entrepreneurship   There are other benefits this program is trying to address namely the high cost of running and managing prisons and high rates of recidivism. In the US according to the Forbes article an average prisoner costs taxpayers $31,286 and 40% of freed prisoners are incarcerated again within 3 years. The Last Mile has shown its astounding potential in changing that trend.


  • There are two customers, the prisoners who go through the program but more importantly the government who wants to see the cost of running prisons go down
  • The value proposition is to give prisoners a fighting chance to make it once they leave prison.  For the government they are hoping to create a solution to the ballooning debt being caused by the prisons and offering innovative solution to do so.
  • Value Proposition (what value do they deliver customers)
  • For the time being there are no revenues
  • Costs are minimal.  Most of the materials are donated as are the time of guest speakers. The main cost is the staff who organize the program and office infrastructure
  • The program is dependent on the support of the California state government, the collaborators and teachers, the prisons and the prisoners themselves (who are for the time being the biggest supporters)


  • Can it be sustainable without state support?
  • what is different about this program than any other vocational training program in state prisons?
  • Can prisoners who have little education and have never seen the internet or social media really be able to start tech companies?
  • What if there is an incident in the program where one of the teachers or anyone else’s safety is actually jeopardized.  Any single incident would be the end of the program
  • It seems to only be focused on the elite prisoners, those most motivated and educated and perhaps least likely to be repeat offenders anyway.  Why not include more prisoners?  Why be so selective?
  • Finally and most importantly to really have impact the program needs to scale across hundreds of prisons.  I am skeptical that this will be easy.  I didn’t say it would be impossible, I just think scaling will be hard.
  • Regardless of all the concerns I think it is a great program and I truly hope for everyone’s sake especially the prisoners it is a success.



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