Blog Article 

 Building Careers in Prison 

Picture of Michael Santos

Michael Santos

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Casey started a roofing company that grew within five years to operate with more than $28 million in revenue. He began his career in his family’s roofing business and worked his way through the ranks by demonstrating strong personality traits, including perseverance, self-reliance, and accountability. Roofing offers a good career option to the formerly incarcerated as the industry often has positions open to those with criminal convictions.

Objective: Lessons for People in Prison

  • In this lesson, participants will learn how the roofing industry offers promise to those leaving prison and jail. In addition, participants will understand why it is important to learn a basic skill set in math, communication, and critical thinking. Upon completing this lesson, students should understand how roofing offers a viable career path and why it is important to master skills in those three areas.

Lesson Requirements:

  • Watch the video that accompanies the lesson
  • Write a definition of each word highlighted in bold and written in italics
  • Use ten of the vocabulary words in a sentence
  • Respond to a minimum of three open-ended questions by following instructions at the end of the lesson.

Lesson Outcome:

  • Participants will increase their vocabulary by at least ten words.
  • Participants will improve writing skills and their ability to contemplate how their responses to open-ended questions relate to their prospects for success upon release.
  • Participants will add to their journal, demonstrating a self-directed, self-improvement pathway to prepare for success upon release.

Our team at Prison Professors thanks Casey for sharing his story on how he started as a tradesperson early in life andlater became a successful entrepreneur. Although he never earned a college degree, Casey founded his own roofing company with minimal capital. Within five years, his business substantially grew and now operates with more than $28 million in revenue.

Many facets of Casey’s story should inspire people in prison or jail. A career in roofing offers promise to returning citizens, as many positions are often open to those with a criminal background. The industry also helps novices obtain a valuable skill set in roles that have significant growth potential. Casey’s story also proves that people without a college education can still enjoy a lucrative career so long as they demonstrate persistence, self-reliance, and a willingness to learn. 

Casey’s Background

Casey exhibits several positive traits found in virtually all successful people, including a strong work ethic, self-discipline, and solid leadership skills. He learned many of these attributes at a young age from his family, which had worked in roofing for several generations. Casey’s father began a roofing business in southern Florida, which exposed Casey to the career that became his niche. 

Before entering the family business, when he was only 14, Casey began his first job bagging groceries. By entering the workforce so young, Casey learned a great deal. He understood the importance of following rules and paying meticulous attention to details. Those lessons helped him throughout his life.

While working, Casey became familiar with the concept of Standard Operating Procedures (SOPs). He defined SOPs as a set of guidelines that outline the way a company should operate. With SOPs, a company defines:

  • employee roles,
  • performance expectations,
  • hours of operations, and
  • the way the business should operate.

Casey emphasizes the significance of SOPs throughout the video as the concept gives important lessons on self-discipline, consistent work, and personal responsibility.

Casey shares that he was less interested in academic activities, instead preferring hands-on work to attain financial success. He attended college for one year but left to pursue on-the-job training in the construction industry. However, even though Casey didn’t prefer a classroom setting, he still valued learning.

Throughout Casey’s life, he sought the advice of more experienced people so he could quickly master the skills to execute his duties effectively. He has also honed his communication, critical thinking, and math skills, all of which have been essential to his business success.

Casey’s early experiences in roofing give valuable lessons in accountability and teamwork. After he turned 16, Casey began working in the family business, which obligated him to work after school hours, over the weekends, and during the holidays in the hot Florida sun. Given the demanding nature of his job, he often worked 60 hours a week alongside seasoned crew members.

Despite his family connections, Casey did not benefit from undeserved privileges in his role. His teammates ensured that everyone in the group, including Casey, arrived on time, did their fair share of work, and took shifts over the weekends. All crew members were required to perform to the highest standards and divide work equitably due to the interdependent nature of the team.

While I was in prison, I would have been inspired by Casey’s story. I would have seen him as a self-made individual who understood the value of hard work and personal responsibility early in life. He shows how tenacious individuals can still move ahead in life despite their background or lack of a college degree. 

Casey became accustomed to a strenuous work culture at his first roofing job. The harsh conditions, long hours, and demands of other crew members strengthened Casey’s resolve and made him more determined to succeed. While I climbed through 9,500 days in prison, Case’s story would have inspired me. His experience serves as a testament to the importance of character in overcoming barriers.


Even today, more than seven years since completing my sentence, I look to leaders like Casey for inspiration. Like many successful people, he entered the workforce at a relatively young age. Often, people who begin working as teenagers develop strong traits that enable later professional achievements, such as promptness, diligence, attention to detail, and consideration of others.

Anyone – no matter their age or circumstances – can adopt these characteristics. Even while incarcerated, people can still change their attitudes to embrace these same traits. 

Casey’s emphasis on the importance of SOPs serves as a good lesson about discipline. Even behind prison walls, people can create an “SOP of their life” by waking up early, journaling, performing their prison jobs well, and adopting constructive habits. We can talk about defining excellence with personal accountability tools in all of our lessons.

By making these positive steps, an incarcerated person can become the CEO of his own life by being resilient and deliberate in their actions. 

Casey’s story also shows that formal education, while invaluable to any individual, is only one of many roads to success. He can inspire people who have not graduated from college but are still willing to invest in themselves through hard work and acquiring new skills.

More importantly, his story shows how education goes beyond merely earning a credential. Even outside the classroom, Casey has relied on communication, critical thinking, and basic math skills in all stages of his career. He remained open to learning by asking questions and listening to those with better skills or more experience. Similarly, people enrolled in GED programs must do more than simply earn the degree. Rather, they must also focus on becoming proficient in the material to fulfill their potential in the workforce. 

  • Why is it important to follow rules, like those written in SOPs, on the job?
  • How can you best create an SOP for your own life while incarcerated? 
  • How can learning a trade or obtaining a vocational education benefit you?
  • Why must you focus on mastering different school subjects?
  • How is mastering school subjects different from earning a degree?
  • How do you hold yourself accountable for your actions?
  • How are you accountable to other members of a team when you work with others?

Continued Career Success 

Casey always found his career gratifying because the results were tangible and visually apparent:he took pride in his role in constructing large buildings in what was once empty space. He also enjoyed positively impacting others. He vividly recalls a sense of fulfillment when he helped other crew members become more adept at their jobs and when he ensured that customers were satisfied with a project’s results. 

Casey learned to become more tolerant from his interaction with people from different backgrounds. At first, he faced communication barriers and social misunderstandings once he began working with Spanish-speaking crew members. Casey overcame that challenge by learning the language, an act that earned him colleagues’ respect and a position as foreman.

Through his persistence and work ethic, Casey rose through the organizational hierarchy and assumed managerial roles. These senior positions required Casey to take responsibility for his team’s performance and persevere through adversity. When he accepted a superintendent role at a construction project in Tennessee, several contractors defected from the team as higher-paying positions were available elsewhere. Rather than focus on the negative, Casey quickly located, hired, and trained substitute workers. His efforts paid off: the project in Tennessee, the largest in the country at the time, was successfully completed.

While incarcerated, I would have resonated with Casey’s lesson on tolerance. At a federal prison in Fort Dix, New Jersey, I was incarcerated alongside prisoners from 91 different countries. In that environment, the prisoners most eager to show tolerance were the most likely to succeed. Casey’s willingness to learn Spanish would have also impressed me as proof of his respect for others and open mindedness. 

In addition, I would have admired Casey’s continued persistence, hard work, and desire to perform well. The personality traits that he acquired as a child enabled him to advance in his professional life. He also distinguishes himself through his pride in his work – he appreciates seeing his team succeed by meeting or exceeding the customers’ requirements.


In prison or jail, it is important to maintain a good attitude, perform well on the job, and treat people of all backgrounds with respect. Though it may be difficult to maintain a good attitude behind prison walls, complaining will only make the situation worse. Successful people focus on what they can control and make incremental progress towards better outcomes.

  • What does it mean to have pride in your work? How can you go “the extra mile” in your everyday life?
  • Why is tolerating people of different cultures, faiths, and language backgrounds important?
  • How will tolerance help you succeed in prison and upon your release?
  • How do you deal with adversity? Why is coping with adversity a vital trait for leaders?
  • What personality traits can you adopt to win the respect of others?


After more than a decade in the family business, Casey started his own company at 27 years old. His first project was only $600 in value, but he quickly gained additional revenue by taking on more projects. At first, his organization grew gradually, hiring around eight to ten people at a time. However, under Casey’s decisive leadership, the company expanded exponentially. Last year, it employed about 255 people and generated $28 million in revenue – an impressive feat considering the business had little to no capital only five years earlier.

Like many owners of construction companies, Casey is willing to hire people with criminal convictions.  Although criminal backgrounds disqualify many people from certain jobs, businesses like Casey’s offer a way to circumvent these limitations. Casey enthusiastically employs those returning to free society, so long as they are prompt, hard-working, and add value to his team. Business owners like Casey show that people in prison and jail can still get hired and advance based on their accomplishmentsdespite their past mistakes.

Casey developed strong business acumen because of his early exposure to the workforce. He had expertise in relevant areas, including motivating teams, selecting the most suitable hires, building SOPs, and sending invoices. He also benefited from his mastery of occupational jargon and fluency in Spanish. 

Each of these abilities relate to the three core areas of communication, critical thinking, and math.

  • Communication – As a business owner, Casey must persuade prospective customers on why his organization is better than its competitors. His team must prepare well-written contracts to inspire confidence in the customer. SOPs also must be clearly worded to ensure employees understand their duties and those of other team members. In addition, Casey’s fluency in Spanish and understanding of industry terms helps him communicate with his team more effectively.

Negotiation is an important concept in communication. Casey worked with a large general contractor who eventually became his business partner. He negotiated with this partner to acquire more profitable projects, such as roofing work on schools and large retail centers. Completing such business deals requires articulate communication in both writing and verbal speech.

  • Math – Roofing involves understanding basic math concepts, such as square footage. Casey notes that the employees with strong math skills are the most likely to be promoted to positions as foremen and estimators. Estimators, those responsible for evaluating a reasonable price for an item, can earn up to $100,000 a year.
  • Critical thinking – Casey had to develop critical thinking skills to make his company successful. He had to ensure that his company had adequate cash flow, could attract investors, and could buy roofing material. His team also uses critical thinking in the various phases of a project, which involve winning a bid, identifying needed inventory, negotiating prices, and selecting a vendor with the best prices. All these processes require Casey and members of his team to think critically to strategize the company’s next steps.


While I served my 45-year prison sentence, I was inspired by opportunities for a second chance in life. People in prison or jail are less likely to fall victim to recidivism once they secure a job. Therefore, Casey offers hope for the formerly incarcerated who want to contribute to society by obtaining gainful employment.

In addition, Casey offers several lessons on the importance of the three subjects of communication, math, and critical thinking. Anyone leaving jail or prison will encounter scenarioswhere these knowledge areas will become essential to their success:

  • Communication: A formerly incarcerated person reentering the workforce must persuade an employer through strong persuasion skills. This individual should prepare a well-written application and cover letter, as well as articulate responses in an interview for a better chance at getting hired. This individual will also need to negotiate well. While looking for a job, applicants often negotiate a salary that reflects their skill level. In addition, finding housing or transportation will likely require strong skills in persuasion and negotiation.
  • Math: An applicant for a roofing job is more appealing to employers if they have at least rudimentary skills in math. A laborer, for example, can augment his value to the team if they can find the square footage of an area, perform basic arithmetic, and measure items. This skill would distinguish this laborer from another who physically robust and able to haul items but is unable to solve math problems.

While people in prison or jail may not have access to useful resources, such as Microsoft Excel, they can still invest in learning basic math skills to quickly learn to use the program upon their release.

  • Critical thinking: An employee with good critical thinking skills is more likely to show promise in their careers and get promoted to more senior roles. For example, the laborer with basic math skills is more likely able to improve their team’s operations. If the laborer by chance notices that one product is of an insufficient size based on measurements, they can advise their employer of the discovery and avert future loss for their employer.

Furthermore, those aspiring to become entrepreneurs must develop basic corporate knowledge and understand business finance.

  • Why is roofing a promising career for the formerly incarcerated?
  • How can you persuade an employer to hire you?
  • How can you use critical thinking skills to solve problems at work?
  • How can you sharpen your business acumen while incarcerated? What skills can you learn now to help you upon your release?
  • How would you define the business terms discussed in the video?
    • Corporate share
    • Equity
    • Capital
    • Inventory
    • Profit/Loss Statement

Hard Work Pays Off

Casey’s story shows how people can achieve great things in life despite their circumstances. He became familiar with roofing at an early age through his family business. As a child, he developed strong leadership traits and business expertise. He later applied these principles to create a multimillion-dollar roofing company even though he never graduated college.  

Overall, Casey’s story shows how a career in roofing is viable for those with criminal convictions or without college degrees. The industry offers such individuals the ability to learn competitive skills, the potential to grow professionally, and the promise of building a successful career. Casey proves that professional achievement is possible for people who value hard work, self-reliance, and accountability. Because he is willing to hire people with criminal backgrounds, Casey offers hope to formerly incarcerated people looking for chances to lead law-abiding lives upon release.

Critical Thinking Questions:

Write at least three paragraphs, with a minimum of three sentences each, for each of the following questions

1. Why does a career in roofing appeal to many formerly incarcerated people? What skills could you learn from a job in this industry?

2. How did Casey’s early start in the workforce influence his success later in life? What character traits did he develop because by starting to work as an adolescent?

3. How can you demonstrate self-discipline, self-resilience, and accountability? Why are these traits important when working with others?

4. Has prison led you to interact with people from different backgrounds? Has this led you to become more tolerant?

5. Casey demonstrated resilience to overcome adversity. How have you demonstrated resilience? Why is resilience an important trait in leaders?

6. What skills can you develop now in the areas of communication, critical thinking, and math to help you advance on the job?

7. Education goes beyond earning a degree. How can you demonstrate proficiency in communication, critical thinking, and math? How will this proficiency help you perform a job well?

8. In your opinion, what characteristics of Casey’s leadership enabled his business to grow so rapidly?

9. What role do essential communication skills, such as persuasion and negotiation, play in your life? How will these skills help you after prison?

10. How does Casey’s story inspire you to live a law-abiding life after prison?

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