Lesson: Casey's Background


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. 


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.

How People in Prison can Prepare for Roofing Careers

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?

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? 

Our team at Prison Professors thanks Casey for sharing his story on how he started as a tradesperson early in life and later 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.