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From prison to code and tech: The Last Mile program

Interview with Chris Redlitz, Managing Partner, Transmedia Capital & co-founder, The Last Mile (TLM)

The American program The Last Mile prepares incarcerated individuals for successful reentry through business and technology training. Here is a conversation with one of its co-founders, Chris Redlitz.

Beverly Parenti and Chris Redlitz, launched their nonprofit, The Last Mile (TLM) in 2010 at San Quentin State Prison, California. The goal of TLM is to provide education and training inside prison, resulting in gainful employment for returned citizen graduates, thereby reducing recidivism. TLM has become one of the most requested prison education programs in the United States. It is the first program to offer a computer programming curriculum that teaches men and women to become software engineers.

What’s the original goal of The Last Mile and how did you come up with the idea of creating such an organization?

Chris Redlitz: In 2010, I was escorted into San Quentin State Prison, one of the most infamous prisons in the world, sitting on the edge of the San Francisco Bay. I was led through a series of gates, down a windy path, through the prison yard, into a small classroom where about 50 men were awaiting my arrival.

After I began speaking, I noticed that many of the men had "the look" that I see in the eyes of founders and entrepreneurs in which I invest, but it was at a deeper level. These men had a look that reflected their hunger to learn, and deep desire to build a better life after they served their time. My 30-minute talk turned into a three-hour discussion.

I left prison that evening, thinking about how Beverly (Parenti) and I could evolve "that look" into something actionable that would help transform these men into successful contributors to our business community when they were released from prison. We did not realize how much this journey would change our lives, make us better investors, and ultimately better people.

Imagine a world where prisons are focused on rehabilitation, not on punitive measures.

Imagine a world where true “freedom” emancipated all formerly incarcerated people from the shackles of their past transgressions.

Imagine a world where diversity and inclusion were the norm, not the exception.

As John Lennon wrote long ago, “power to the people, right on…” There is strength and commitment when groups are empowered with skills, direction, and belief for a greater good. There is a community of people behind bars who have hopes and dreams, and represent an untapped resource of talent that can be positively unleashed on America’s business community. The groundswell of enthusiasm and commitment around criminal justice reform can easily be amplified into an audacious dismantling of the systemic inequities that plague communities across America.

Can you share with our readers striking key figures about education in prison in the US? How did it evolve over the last 20 years?

C. R.: Today, approximately 1.8 million people are incarcerated in the United States. Most of these people (95%) will return home to their families and communities. The question is: “Who do you want them to be”? The unemployment rate for these returning citizens is about five times higher than that of the general population. The lack of meaningful employment opportunities for returned citizens is a primary factor driving America’s 64% recidivism rate.

A lack of adequate job preparation during incarceration greatly increases the likelihood of people reoffending and returning to prison. The exclusion of formerly incarcerated jobseekers from the workforce costs the United States an estimated $87 billion in lost GDP. Furthermore, between 60 to 75% of those formerly incarcerated remain unemployed one year after release. We believe that having a job is the key to successful reentry and breaking the generational cycle of incarceration.

Meanwhile, according to the Bureau of Labor Statistics, an estimated 1 million US software engineering jobs are unfulfilled due to a deficit of trained individuals to fill these positions. The Last Mile (TLM) will significantly reduce recidivism by enabling formerly incarcerated people to join the workforce with 21st century job skills. TLM has developed a program that provides industry-specific training to prepare our students for successful release into today’s high-tech environment. TLM graduates are well-positioned to qualify for many of these jobs. We are creating pathways for highly skilled returning citizens to connect with organizations in need of adequately trained people.

The Last Mile is currently in 23 classrooms, across 6 states (including four women's prisons). Our goal is to become a national program within the next five years.

We're not only preparing men and women in prison for future employment, but we're also breaking the cultural and ethnic divide within the prison culture.

This inspiration, emanating from one of the most unlikely places on earth, provides hope to incarcerated men and women across the US, and proves that anything is possible. Hopefully you'll be as lucky as I have been, to find inspiration and a mission that will impact your life and the lives of many others. As we say in The Last Mile, we are all on a journey, "Paving the Road to Success" if we all "Believe in the Process”.

How did you first approach the prison warden (or the State of California) to pitch your idea? What about the inmates? How did they react?

C. R.: “If you give people a different perspective, just show them the world is bigger than the block we’re on, they see the world differently. This skill set, software engineering, it can save lives.” -- MC Hammer, TLM Board Member

When a group of motivated people are developing something that seems implausible, it requires unconventional thinking and unlikely collaboration. Through this process, TLM has overcome the most significant hurdles that would have prevented the organization from becoming the most important and aspirational prison education program in the country.

I'm a venture capitalist at Transmedia Capital living in Silicon Valley, the heart of the world's technology innovation and investment community. I've been here for 20 years. I never thought deeply about pursuing a social cause or dedicating myself to anything beyond my career and my family. But my mindset changed on that evening in San Quentin in 2010.

Beverly and I thought we could help some of the men we met in our subsequent visits to San Quentin, to create businesses or secure jobs, if we provided the proper training. We weren’t sure if  the men inside would understand the basic concepts of business or communication skills. We also had this pre conceived notion that most incarcerated people at San Quentin were under educated and beyond the point of redemption. What we discovered quickly changed our perspective and ignited our sense of responsibility to help change a broken system and rewrite the narrative.

We approached the California Secretary of Prisons with a business plan and several KPIs (key performance indicators) for our initial premise for The Last Mile . He was enthusiastic about our plan, but no doubt a bit skeptical that we would be successful. However, we made a commitment to follow though, regardless of the obstacles with the same determination we have put forth throughout our lives.

The success of the The Last Mile organization and the dedication of our students over the last 11 years has exceeded our expectations and is truly the most meaningful thing we’ve ever done.

What was the biggest challenge you faced when first implementing this program within the walls of the prison? How were you able to solve it?

C. R.: The biggest hurdle was the education of correctional administrators across the US to understand the significant benefit of the program, and to understand that technology in the prison environment should not be concerning or threatening if it is managed under the proper supervision and security protocols.

Creating a prison education program that teaches and utilizes sophisticated technology is a daunting challenge. Prisons are fundamentally analog and hesitant in their approach to accept and endorse new systems and strategies. Not only does it require commitment and effort to develop a positive and progressive approach, but for the most part, the prison industrial complex does not provide any incentives for correctional officers or administrators to implement programs that improve education and training for incarcerated populations. In addition, many states have powerful lobby groups and unions who thrive on the status quo.

Over the last 11 years, TLM was able to build a rapport with incarcerated populations, executive leadership, and correctional facility administrators across the United States. The success of TLM is changing the perception in the business community showing that justice impacted men and women can become great employees, and productive members of society.

From its inception, TLM has been intentional about applying shared values across our organization such as value creation, equal rights, personal responsibility, openness, and respect. TLM’s impact on thousands of incarcerated people and the downstream positive outcomes will create a dramatic multiplier effect that will impact families and communities across the country. There is no reason why the US should remain the country with the world’s largest incarcerated population or why the United States has one of the worst rehabilitative processes among the leading nations in the world.

What are the different curriculums that are being taught to incarcerated adults? How important is tech in this program? Why?

C. R.: The Last Mile coding program was established to provide an intense, skill based curriculum for incarcerated men and women leading to future vocational opportunities. The curriculum is packaged into transferable content modules, allowing approved facilities to effectively operate the program. The program is structured as a progression towards the normal day-to-day life of a software engineer in an entrepreneurial environment, beginning with heavy lecture based content, lab training sessions, and culminating with independent “capstone” projects.

Participant Qualification:

–High School diploma or GED

–Basic typing skills

–Excellent disciplinary record (no infractions within 24 months of


–Release date within 36 months

–Complete pre qualification exam and interview.

Participants in The Last Mile coding program must complete two 6-month cohorts and pass a technical assessment test to receive a certificate of completion. Instruction focuses on: HTML, CSS, JavaScript, design, and data visualization. The students are required to participate in a minimum of 30 hours of computer lab time per week. The curriculum is presented by an onsite coordinator and virtually through a dedicated internet connection using Google Hangouts. All virtual instruction emanates from The Last Mile studio in San Francisco and remote studios in California and Indiana. All virtual instruction sessions are recorded and archived for future use.

A program syllabus outlines each two-week module, highlighting the educational material the participants must read or videos to watch. This helps them learn the module’s concepts, exercises to practice those concepts, a “capstone feature” to apply directly to their Capstone Project, and any scheduled quizzes to test how well they have learned the material.

Course Content:

The following “modules” are covered during the cohorts:

–Foundations (The tech sector, tool set: browsers, text editors)


–Introduction to Javascript

–Javascript & the DOM

–Bootstrap & jQuery

–Javascript Functions

–Introduction to MVC (Model-view-controller)

–Elements of design

Weekly exercises and problem sets based on the reading material for each module help participants practice specific concepts covered in the module. The participants solve the exercises before moving on to capstone features or other advanced work, and that the participants try and retry solutions on their own before asking for help. The material contained in weekly exercises is very similar to the obstacles they will face as a professional software developer, and will almost certainly resurface in interviews for programming jobs.

What are the next steps in the evolution of the Last Mile program?

C. R.: “This will help train and equip women in this facility in the skills they need to secure a job in the field of software engineering post-incarceration.” -- Governor Kevin Stitt, State of Oklahoma

The basic premise of vocational training in high demand markets has proven to increase social mobility, open career pathways, and reduce recidivism. This pathway has united our funders in their support of our mission. TLM has engaged unlikely collaborators in the business and philanthropic communities with the drive and motivation to create change.

Based on our learnings and track record over the years, TLM has the opportunity to become the de facto platform for prison education. TLM has established itself as the most aspirational and successful prison career training education program by providing an unprecedented opportunity for incarcerated participants to return home and become software engineers. The results have surpassed all expectations both in career pathways and reducing recidivism. TLM Returned Citizen graduates are setting a new standard of what is possible for people who were never exposed to technology and business with companies like Slack, Zoom, Square, Checkr, Plaid, and Dropbox hiring our graduates and paving the way for other justice impacted men and women to be welcomed into the tech business world.

Public private partnerships can accomplish what the public stakeholders alone lack the capacity to manage. TLM has bridged the gap between good intentions and actionable change. Most state correctional departments across the country are not fulfilling their obligation to rehabilitation programs, but many are willing to invest in systems and relationships that can alter the status quo.

Creating sustainable systemic change requires more than public rhetoric, surface level legislation, or hollow press statements. The core premise of TLM is to empower people to take control of their lives and create fundamental change for themselves, their families, and their communities. Every prison in America should be required to provide rehabilitative services that fundamentally improve the outcomes of those individuals who return to society after serving time.

In addition to coding, TLM is developing new programs that will train learners to become IT network engineers, certified audio technicians and video editors. TLM’s new music and video production (MVP) program will not only train participants with audio and video career skills, but also provide an opportunity for talent discovery related to music and spoken word that will reveal creative talent that is hidden behind bars across America. The content that is discovered will be utilized within the MVP program, and eventually presented to the world.

For TLM to effectively scale to meet its goal of 50 classrooms by 2024 and increase the depth of its learning management platform and the team to support this growth, will require additional financial resources. TLM is in a unique position to create significant changes in prison education, recidivism rates, and help balance the diversity gap in corporate America.

Chris Redlitz will be a speaker at the Digital Summit next September 14th at European Convention Center Luxembourg. Among other things, he will present The Last Mile program during a morning which will have for theme: “Reconciling Tech & Education: advancing knowledge around latest tech trends and how it helps people access to better education”. Digital Summit is part of the renowned tech summit ICT Spring Europe.