Lesson: Entrepreneurship


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



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 accomplishments despite 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 scenarios where 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? 

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.