Prison Professors

Annotation

In this MasterClass, we learn from Thomas, a resilient entrepreneur whose story blends early ambition, hard-earned success, and a commitment to reform. After decades of building businesses and defying the odds, Thomas found himself entangled in the criminal justice system. Rather than succumbing to despair, he chose to lead with courage, integrity, and a spirit of contribution.

Thomas’s story is not only about a trial and a sentence—it’s about standing up, owning the narrative, and using that experience to help others. He’s become a living example of what it means to be the CEO of your life, no matter what obstacles you face. Whether you're awaiting trial, serving time, or preparing for reentry, this lesson offers actionable insights and inspiration to help you craft a stronger future.

Objectives

After completing this lesson, you will be able to:

Understand how early values and work ethic shape long-term outcomes
Recognize the emotional and practical challenges of facing a federal sentence
Use entrepreneurial thinking to solve problems, even while incarcerated
Apply the Straight-A Guide to real-life decisions before, during, and after a sentence
Develop a self-advocacy record using tools like Prison Professors Talent
Articulate a personal definition of success and outline steps to get there

Background

Our nonprofit is dedicated to improving outcomes of America's criminal justice system. What does "improve" mean? It means we want people who go into the system to emerge successfully, with their dignity intact, at the soonest possible time.

Success depends on finding passionate volunteers who share our mission. Driving meaningful change requires an understanding of the system’s complexities. Together, we can inspire progress and advance reform. To succeed, we need to make many plans, and we must create self-directed resources to help others learn:

How the system functions?
What are the ideal outcomes the system should strive for?
What steps can we take to improve the system?
How can individuals within the system become active contributors to the solution?
How can we gather data to strengthen the case for reform?
How can we build stronger coalitions to support the reforms we aim to achieve?

By addressing these questions, we can pave the way for meaningful, lasting change.

I am grateful to Thomas for reaching out and offering his time and expertise to support our mission. As a business leader, Thomas exemplifies the principles of the Straight-A Guide. The more I learned from his story, the more I could see how he'd been living according to those principles his entire life, long before he learned anything about our work.

It validates what we say in all our courses:

The Straight-A guide isn't anything I created. I learned by listening to leaders, and looking for clues that they used to become successful. By observing leaders, I wrote out a framework that would guide me through 26 years in prison, and continued writing to show others how they could do the same.

When Thomas expressed interest in volunteering and contributing to our initiatives, I asked him to share his story, which shows the value of perseverance, and making values-based, goal-oriented decisions. It's inspiring to me, and I'm especially grateful that he collaborated to make this self-directed lesson plan for members of our community.

Thomas’s journey began in Texas, where he was raised by a single mother in a modest home. From an early age, he understood that anything worth having had to be earned. During his adolescence, he wanted the same kinds of gadgets that other children had. Since his family couldn't afford it, he decided to put forth the work that would allow him to get things on his own.

He took a self-directed path to go after the things he wanted. Looking around, he considered the resources available to him and figured out he could use them to create value. With a lawn mower, he saw a resource that he could turn into an opportunity. He began knocking on doors in the neighborhood, offering to mow lawns for a reasonable price.

Lessons from Ingenuity

Thomas's initiative with the lawn mowing business taught him valuable life lessons that extended far beyond earning money. By identifying an opportunity and acting on it, he learned the power of creativity, perseverance, and resourcefulness. These lessons would become foundational skills that shaped his future endeavors. Below is a list of the key values he would have gained by being self-directed:

Taking Ownership of Goals

Thomas learned to take responsibility for his own aspirations, understanding that success begins with proactive effort and dedication.

Identifying Opportunities in Everyday Resources

He realized that even simple tools, like a lawn mower, could open up doors when combined with initiative and action.

Building Confidence Through Action

Knocking on doors and building relationships with neighbors boosted Thomas’s confidence in his ability to take initiative and communicate effectively.

Understanding the Value of a Self-directed Work Ethic

Through hands-on experience, he gained an appreciation for the effort it takes to earn and achieve something valuable.

Adapting and Problem-Solving

Each new customer or task brought its own set of challenges, teaching him to think creatively and adapt to meet varying needs.

Communication

Thomas understood that by developing better communication skills, he could succeed at a higher level.

By recognizing these lessons, Thomas developed the virtue of resilience and a mindset for innovation. He recognized the importance of developing "an internal locus of control."

Internal Locus of Control vs. External Locus of Control

When examining how individuals perceive control over their lives, the concepts of an internal and external locus of control emerge as two powerful perspectives. An internal locus of control centers on the belief that one’s own actions, decisions, and efforts primarily shape the outcomes of their life. Those who embody this mindset take responsibility for their successes and failures, understanding that their dedication and choices play a pivotal role in determining results.

On the other hand, an external locus of control attributes life’s outcomes to external forces, such as luck, fate, their environment, or the influence of others. Individuals with this perspective may feel that their ability to change their circumstances is limited. Instead of taking action, they wait for external conditions to evolve or improve. They complain about what happened to them rather than think about what steps they can take to influence better outcomes.

The critical difference lies in empowerment and accountability. While an external locus of control can often leave individuals feeling powerless or reactive, an internal locus of control empowers individuals to take proactive steps toward growth and change. By adopting an internal locus of control, people can make the most of any situation, leveraging their own skills, creativity, and determination to overcome obstacles and seize opportunities. This mindset minimizes reliance on chance or external validation and fosters a sense of purpose driven by their own values and goals.

By mowing lawns, Thomas understood that he had the power within to create new opportunities. What began as a small hustle quickly grew into a thriving business. His meticulous attention to detail set him apart. While other kids rushed through their chores, Thomas ensured every lawn was perfectly trimmed. His grandfather’s words became his guiding principle: “Every job you do—that’s your name on it.”

That commitment to excellence defined Thomas’s life. By high school, he had built a full roster of clients and was successfully running his own landscaping business. Further, he developed skills in creating jobs—opening opportunities for him to contribute to his community. Although he could earn money by mowing lawns, he could do even better by building a business. This meant he had to generate more leads, acquire more capital equipment, and incentivize classmates to become a part of his mission.

Thomas didn't only focus on earning money. He wanted to build confidence, and a pathway to success. Others didn't believe in his capacity, and he rejected their negativity with a fierce determination to prove them wrong.

In the third grade, a school counselor labeled him “borderline mentally retarded,” insisting he would never achieve more than average grades, let alone go to college. Instead of letting that label defeat him, Thomas used it as fuel. He studied relentlessly, took on advanced placement classes, and joined honor societies, determined to defy expectations. In other words, Thomas always knew how to define success, and he understood that he could take proactive steps to reach a higher potential.

Without financial support beyond his own earnings, Thomas put himself through college. He chose to study psychology and went on to earn a master’s degree in industrial psychology, a field focused on improving workplace efficiency and human interaction. During graduate school, he worked in military and research settings, even publishing a peer-reviewed paper with a prestigious journal for the Air Force.

Still, Thomas’s entrepreneurial spirit pulled him in a different direction. After completing his degree, he pivoted to sales—not because of prior experience, but because he believed in learning through action. Unlike the stereotypical extroverted salesperson, Thomas relied on observation, listening, and asking thoughtful questions. He had cultivated those skills throughout his adolescence—a residual that came from working with hundreds of customers through his lawn service business.

Clients valued his sincerity and trusted his solutions. Over time, he blended his deep understanding of human behavior with a talent for problem-solving, building relationships founded on trust and genuine care.

Thomas’s story is one of grit, resilience, and purpose—a powerful example of what it means to overcoming stigma, staying committed to values, and rising with integrity and a self-directed commitment to pursuing excellence.

One of Thomas's greatest breakthroughs began with solving a personal challenge. After purchasing a home with a shifting foundation, he tried to find a solution. Engineers told him the problem and what had to change to improve the structure. Tapping into all the lessons he learned from working with lawn care, he devised a proprietary irrigation system to stabilize the soil.

When Thomas showed his solution to the consulting engineer, an opportunity opened. The engineer suggested that Thomas advance his idea, offering a service to others. That conversation sparked the creation of a new company. His impressive results led the engineers to begin recommending customers to Thomas. The business quickly gained traction. Thomas earned his irrigator’s license, designed a system using advanced moisture sensors, and built a dedicated team to install and manage these systems. Soon, both landscape architects and homeowners were lining up for his services.

This success was just one chapter in Thomas's journey. He understood the pillars of running a thriving business—meticulous financial records, exceptional customer service, and operational transparency. He ran the company with professionalism, ultimately selling it to another contractor. From there, he returned to corporate sales but continued nurturing side ventures. Thomas approached life with intention, turning every lesson, job, and experience into an opportunity to grow as a leader and builder.

Thomas eventually exited that business, selling it to a competitor. He used those resources to launch numerous other ventures. He always recognized that earlier lessons and incremental success would put him on the pathway to new opportunities.

Lessons from Adversity

Then came 2018. Without warning, federal authorities contacted Thomas, telling him that they had launched an investigation into various business with which he was affiliated. They led him to believe that he would be a witness to the investigation.

Witness, Subject, Target

When federal investigations begin, individuals involved are often categorized into three distinct roles: witness, subject, or target. A witness is someone who has observed relevant events or possesses information that could aid in the investigation; they are not under scrutiny themselves but are valuable for uncovering facts. A subject, on the other hand, is someone whose actions fall within the scope of the investigation and who may have played a peripheral or critical role in the events being examined. Lastly, a target is the primary focus of the investigation, indicating that authorities have substantial evidence linking them to potential wrongdoing and are likely to pursue charges against them. Understanding these roles is crucial for navigating such situations, as each comes with varying levels of legal exposure and risk.

Thomas didn't have anything to hide. He prided himself on being a responsible corporate citizen, committed to both legal compliance and ethical standards. Believing he was merely a witness, he willingly cooperated with the investigation—providing records, fulfilling every request, and answering questions openly and transparently.

The authorities never told Thomas they considered him a target of the investigation.

Years passed without updates. Then, unexpectedly, the authorities indicted him in a healthcare fraud case. There were 17 other people charged, most of whom were physicians or healthcare professionals without any connection to Thomas. He never met many of his codefendants.

Insisting on his absolute innocence, he proceeded through trial and refused to accept a plea agreement—even though it would have kept him out of prison. Thomas refused that plea agreement, because to accept, prosecutors would have required him to implicate people whom he did not know anything about. He refused to try to save himself by labeling others as criminals, when he didn't know anything about them, or about a crime being committed.

Other defendants accepted a plea agreement. In exchange for their cooperation, the judge imposed a modest financial sanction instead of imprisonment. The attorney who represented Thomas called those physicians as witnesses in the trial, and those people testified that they did not know Thomas.

Despite the facts in the case, the jury returned a guilty verdict. The judge imposed a term of 12 months and one day in prison, along with a $25,000 fine. His legal fees soared into the millions, and the damage to his reputation was immense. Yet, rather than succumbing to bitterness, Thomas made a powerful choice: to turn his experience into a force for good.

In the weeks leading up to his incarceration, Thomas became certified as a life coach and began working pro bono with individuals in crisis. He began volunteering with Prison Professors, a nonprofit, to create resources that would become a part of our curriculum. While he served his sentence, he pledged to document the ways that he was using this crisis in his life to open new opportunities for others, teaching people in struggle how they could navigate pathways to success in the future.

There are always more opportunities in the future than in the past, especially for those who prepare.

I'm grateful to Thomas for volunteering with our community, not only by sharing his message, but also for collaborating in the development of this lesson plan. I consider his story as testament to resilience, leadership, and the power of reclaiming one’s identity. It serves as a beacon of hope for anyone seeking to rise above adversity and lead from within.

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Vocabulary

Resilient – Able to recover quickly from difficulty
Entrepreneur – A person who starts and runs a business
Advocacy – The act of supporting a cause or proposal
Integrity – Adherence to strong moral and ethical principles
Credibility – The quality of being trusted and believable
Trajectory – A path or progression over time
Liberty – Freedom, especially as it pertains to movement or rights
Stakeholders – Individuals or groups with an interest in a decision or outcome
Dignity – The state of being worthy of respect
Iterative – Repetitive in a way that refines or improves over time
Transparency – Openness and honesty in communication or behavior
Self-advocacy – Representing and speaking up for oneself
Systemic – Relating to a system, often implying broad and structural issues
Disposition – A final settlement or outcome of a case
Restitution – Compensation for loss or harm caused

Self-Directed Questions

How has Thomas’s early work experience shaped his values?
What does it mean to maintain integrity under pressure?
In what ways has Thomas used adversity to grow?
How can you start building your own record of preparation?
What does it mean to become the CEO of your own life?
What is one problem you’ve already solved that shows your initiative?
What does advocacy look like for someone serving time?
How do you define success from your current environment?
How can you build relationships that will help you succeed post-release?
What can you do today that your future self will thank you for?

Reflection Journal Prompt

Think about a moment in your life when you were treated unfairly—whether by the justice system, your environment, or even your own family. How did you respond? Now, imagine helping someone else navigate a similar experience. What advice would you give them based on what you’ve lived?

Sample Student Response

Question 4: How can you start building your own record of preparation?

While I’m inside, I’m doing everything I can to create a body of work that reflects who I am—not just who the government says I am. I read daily and document my takeaways. I write in a journal. I complete courses from Prison Professors and mail my answers home so my family can add them to my Prison Professors Talent profile.

When I talk to other people in my housing unit, I share what I’m learning. I offer to help them read through these lessons too. Sometimes we even write sample business plans or prepare for release together.

I don’t want to be remembered by the worst decision I made. I want my body of work to show that I’ve grown, matured, and prepared. Like Thomas, I know that liberty doesn’t begin with release—it begins with accountability. Every day I invest in myself is a step toward building credibility for the future.

Project: Build Your Biography

Create your personal biography for Prison Professors Talent. Include:

Your name and what you’ve learned from your journey
The values you live by
What you’ve done to prepare for success
How you intend to contribute to others

Ask a peer to review and give feedback before submission. Use this bio as the foundation for your release plan and share it with your case manager when appropriate.

Quote to Remember

“Every job you do—that’s your name on it.” — Thomas’ grandfather

What job are you doing today that reflects your character?

Knowledge Check (Optional)

What sentence did Thomas receive, and how does it compare to others who pled guilty?
What entrepreneurial innovation did Thomas create early in his career?
Why is a one-year-and-one-day sentence significant?
What tools is Thomas using to build his release plan?
What are some ways Thomas plans to contribute to the justice reform movement?

MasterClass with Thomas