From Prison to a Top Tech Company: Jacob Robinson’s Story October 21, 2024 Jacob Robinson, Alumni of The Last Mile Jacob Robinson once faced a bleak future behind bars, but his journey from incarceration to a thriving career in tech is nothing short of remarkable. With the help of innovative programs like The Last Mile and Formation, he gained the skills and confidence needed to succeed. In this article, we explore how reentry initiatives are breaking the cycle of recidivism for those who are determined to rebuild their lives. As Jacob Robinson sat in his prison cell, four years into what would turn out to be a six-year sentence, he deeply questioned what his life would look like after release. Up until that point, his aspirations had been limited to what he knew: factory work and simply getting by. But around that time, Jacob made a pivotal decision to join The Last Mile (TLM), a prison education program providing technology training and coding. This was a choice that would change everything. Within the first few weeks of learning how to code, he realized that breaking into the tech industry was the direction he wanted to take his life, though the path forward was still unclear. TLM opened his eyes to a world he had never imagined being part of, setting him on the course to a better life and a career he had once thought was out of reach. Fast forward to July 2024. Two days before the anniversary of his release, Jacob Robinson walked through the front doors of Asana, one of the top tech companies in Silicon Valley. He started his first day as a software engineering apprentice, a transformation nothing short of incredible. How did a man who had never touched a line of code before prison find himself in this position? For many justice-impacted individuals, reentry into society is fraught with challenges, and few have access to the resources necessary to break the cycle of incarceration. This is the story of a justice-impacted individual who not only reintegrated into society but entered a high-level, competitive job market. Jacob used determination, mentorship, and the collaboration between two life-changing programs: The Last Mile (TLM) and Formation. The Challenge of Reentry: Why It Often Fails For most people leaving prison, the path to reentry is riddled with obstacles. More than 63% of those released from incarceration fail to secure full-time employment within the first year. Without stable employment, individuals often fall back into the habits that led them into the system, often committing new offenses simply to survive. This is the grim reality of recidivism in the U.S., where more than two-thirds of released prisoners are rearrested within three years. At The Last Mile, we work to change this narrative. By providing justice-impacted individuals with access to technology education while they are still incarcerated, TLM creates a bridge between prison and a highly competitive job market. However, education alone is not enough. The world beyond prison walls is a different kind of challenge that requires more than just technical skills – it requires a total transformation of mindset. “The biggest challenge for justice-impacted individuals isn’t just learning to code,” said Jacob. “It’s changing the way we see ourselves. You spend years surviving by following orders. When you get out, you have to be able to take charge of your life and represent yourself in ways you never had to before.” The Last Mile now serves 300 students a day across prisons in 8 states, providing every graduate with a desirable skill set that qualifies them for a wide range of tech, coding, audio engineering, and video engineering positions. But while these skills open doors, the road to post-release employment is far from easy. For many, transitioning from prison to a professional environment presents challenges beyond technical skills. This is where the next crucial step begins—bridging the gap between possessing the skills and having the confidence to succeed in the workplace. Graduates like Jacob Robinson often need more than just coding expertise; they need guidance on how to navigate interviews, corporate culture, and the professional world. Enter Formation, a program designed to empower justice-impacted people with the mindset needed to thrive in the tech industry. Formation: Helping Justice-Impacted Individuals to Build Tech Careers Formation is an AI-powered, personalized interview preparation program designed for people from nontraditional backgrounds. Formation customizes its training to meet the specific needs of each participant, ensuring they focus on the areas where they need the most support. For someone like Jacob, who was new to the tech world, the program helped him sharpen not only his technical skills but also his mindset and approach to professional environments. The program adapts to every individual’s experience level, whether participants are just starting out or have years of experience. Both Jacob and, for instance, a seasoned software engineer from Amazon, could pursue their career goals efficiently using the automated programs. Daniel Tomko, Head of Instruction at Formation, recalled his first sessions with Jacob. “He had the skills and drive, but his biggest challenge was confidence,” Daniel shared. “Jacob was still carrying the weight of his past. He didn’t believe someone coming out of prison could land a job at a company like Asana.” For many justice-impacted individuals, the prison environment fosters a mindset of survival through compliance—do what you’re told, follow the rules, and don’t question authority. This mentality, while essential in prison, becomes a liability when transitioning to a corporate environment. This is particularly true in tech, where innovation and independence are key. Daniel explained the challenges his students face: “In tech interviews, companies are looking for engineers who can take initiative. You can’t ask permission every time you want to write code or make a decision. That’s where justice-impacted individuals struggle—they’re conditioned to seek approval.” Jacob echoed how this challenge manifested in his own journey: “In prison, you learn to stay in your lane. It’s a survival mechanism. But when I started at Formation, I realized I had to unlearn those habits. I had to learn how to be proactive, to take control of my career.” Formation’s mentorship model focuses on this crucial mindset shift. Through one-on-one coaching, mock technical interviews, and behavioral training, Jacob learned to present himself with confidence and to approach challenges with a problem-solving mentality. “Formation felt like an extended family,” Jacob said. “They cared about me, not just as a software engineer, but as a person. That level of support helped me break free from the mindset that had held me back.” The Last Mile and Formation: A Partnership for Success The partnership between The Last Mile and Formation is a blueprint for how justice-impacted individuals can be set up for success. Inside the prison, TLM lays the foundation. We provide individuals with hard skills in coding and digital literacy while still incarcerated. Formation picks up where TLM leaves off, equipping released graduates with the tools to navigate the real-world job market, from technical interviews to interpersonal communication in the workplace. Together, these programs ensure that graduates like Jacob not only survive, but thrive in their new lives. “What makes this partnership special is that it addresses the full spectrum of what justice-impacted individuals need,” Daniel told us. “It’s about building up their confidence, giving them the tools to succeed in a competitive environment, and showing them that they belong.” A Vision for the Future: Transforming Incarceration From Day One Imagine a future where every incarcerated individual begins planning for their reentry on day one of their sentence. They are given the tools, resources, mentorship, and education to develop a highly valuable skill set that prepares them to thrive when they leave prison. Jacob’s story shows us that this future is within reach. Programs like The Last Mile and Formation are catalysts for transformation, turning barriers into opportunities and helping individuals like Jacob emerge stronger, more confident, and ready to contribute to the world in ways they never thought possible. By Robert Roche, Content Marketing Director at The Last Mile Want articles like this one in your inbox? Subscribe to The Last Mile Marker, a newsletter offering in-depth insights, critical updates, and inspiring stories on criminal justice reform and second chances.