Blog Article 

 How to Become an Entrepreneur After Prison 

Picture of Michael Santos

Michael Santos

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  • How to Become an Entrepreneur After Prison


  • Born and raised in Ohio, Mark started small and grew into an entrepreneur as he launched multiple businesses. Alhtough Mark did not graduate college, the lack of a university degree did not hold him back from building and owning businesses that have created well over 500 jobs for people in his community.


  • Mark’s inspiring story demonstrates that willingness to embrace hard work and entry-level job opportunities can serve as a bridge to success. People in prison will learn the importance of developing excellent critical thinking and communication skills.

Lesson Requirements:

  • Watch the video that accompanies the lesson
  • Write a definition of each word highlighted in bold and written in italics
  • Use 10 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 develop vocabulary by at least ten words.
  • Participants will improve writing skills
  • Participants will connect how their responses to open-ended questions relate to their prospects for success upon release.
  • Participants will demonstrate self-directed, self-improvement pathways to prepare for success upon release.
  • Participants will document new knowledge in their journal

Our entire team at Prison Professors expresses gratitude to Mark for sharing his experiences with us. Mark exhibits the work ethic necessary for people to succeed in business. Mark serves as a role model in his community by giving back and creating hundreds of jobs.

Mark’s Back Story:

Mark grew up in a loving home in suburban Cleveland, OH. His father was an entrepreneur who owned several businesses, often working 80-hours a week to ensure the businesses were successful. Mark felt motivated by his father’s example of hard work, commitment, and detrermination. Inspired by his father, Mark applied himself in school. He earned good grades and played sports. His positive attitude and a drive to succeed led to business opportunites in different industries that opened throughout his career.

While Mark’s early family life contributed to his success, not everyone enjoys the same kind of supportive and stable childhood. Mark differentiated himself from others by earning above-average grades. By participating in team sports, along with developing skills in reading and writing, Mark developed traits of good character that advanced his prospects for success. Mark created many positive life images for himself through his role model/father.

Successful business owners understand the nexus between commitment and success. As entrepreneurs, they willingly work 80-hour weeks on their own business to avoid working 40-hour-a-week jobs. Many people have the misconception that the boss doesn’t work hard since they’ve already achieved some level of success. Being a business owner comes with tremendous responsibilities. To succeed financially, business owners must:

  • Comply with regulations,
  • Hire staff and define roles,
  • Lead, motivate, assess, and develop employees
  • Create standard operating procedures,
  • Define excellence at every level of the organization,
  • Create compensation plans,
  • Figure out strategies to generate leads,
  • Close transactions,
  • Fulfill orders and build good will.

Mark graduated from high school in Ohio. From an early age, he wanted to help his community. Through business ownership, his father created many jobs. Mark aspired to emulate his father’s leadership. He wanted to help people. Even as a teenager, Mark appreciated how he could achieve positive results by putting in the hard work necessary to become financially successful.    

After graduating high school, Mark understood that he should take calculated risks. Although he wanted to attend college, he wasn’t positive about where his pathway led. Mark enrolled in criminal justice courses when he entered college. He began to manifest his commitment to community involvement and helping others.


People participating in our Prison Professors courses should see the value in these profiles of successful people like Mark. They inspire hope, helping us to see that with hard work, we can advance our fortunes in life. Success stories like Mark’s served as a source of motivation, influencing my adjustment through tough times.

  • How did Mark’s upbringing affect his early decision-making?
  • In what ways do you think he learned from his father?
  • What people influenced your life in a positive way?
  • In what ways do you strive to contribute to your community?
  • In what ways do you take calculated risks to achieve your goals?

Mark’s Entrepreneurship:

While Mark initially enrolled in criminal justice program in college, he transitioned majors to education, thinking that he could teach children and perhaps coach youth sports. Again, Mark committed his future to helping others.

While accumulating credits toward his degree, Mark simultaneously worked two jobs—as a sandwich maker at a local Subway restaurant, and as an employee for UPS. Mark took his jobs seriously. At Subway, Mark developed his communication skills and also learned the importance of customer service. At UPS, he unloaded boxes from trucks and learned different jobs by interacting with different people—incorporating positive examples he saw from his coworkers and managers. Mark modeled his work performance after people whom he saw doing good work. As supervisors became aware of his commitment to excellence they saw his potential and promoted him to positions of increasing responsibility. 

Mark left college before completing requirements for a bachelor’s degree, wanting to develop more skills in business. He worked waiting tables at TGI Friday’s for several years. Once again, working in the hospitatlity industry helped him develop strong communications skills. He honed his communication skills by focusing on service-oriented interactions with supervisors and customers.

Later, Mark accepted a job with the Frito Lay corporation. The warehouse position required him to load boxes into delivery trucks during the overnight shift. As has happened through his life, a solid work ethic and effective communication skills opened relationships that led to new opportunities. 

Regardless of what job Mark held, he always set goals of doing the best job possible. The more skills Mark developed, the better jobs he obtained. He earned a high level of responsibility and a concomitant increase in salary due to his dedication.      


When climbing through challenging times, we may not identify growth opportunities. We learn to increase our awareness of those prospects by studying the patterns of leaders like Mark. Many people who achieve high levels of success begin their careers in entry-level positions. With hard work and focus, they create new opportunities.

To be successful upon my release from prison, I knew excellent communication and critical thinking skills were mandatory to becoming successful. I took every opportunity to surround myself with positive influences. I also took deliberate action to develop my vocabulary and public-speaking skills while gaining confidence in my communication and networking abilities.

Anyone in prison can learn these skills. They can learn from successful business owners like Mark through this Prison Professors course, or they may find people around them that have lessons to share. If you are concerned about what your life will be like after your release, ask yourself these questions:

  • What have you done today to prepare yourself for new opportunities?
  • What short-term goals can you set for yourself?
  • Think to yourself about a fellow person in prison who can help you develop new and better communication skills.
  • Choose books from the library that will develop your communication and critical thinking skills to help you be successful after you’re released.
  • In what ways are you prepared to effect change toward a better life?

Next Level Business Success:

While working at Frito-Lay, through his weekend recreational football league Mark learned that two co-workers and teammates planned to open a mortgage brokerage business. After asking them questions about the mortgage industry and doing his own independent research, his teammates offered him a job. Mark landed his first office job, a step he knew would lead to further financial success.

When Mark started work with the mortgage company, he knew this would be a different experience than working in a blue-collar job. There were high expectations for excellent communication, reading, math, and writing skills for all office employees. Mark saw an opportunity to learn things about an industry with which he was unfamiliar, things that would lead to his success. He learned how to read personal credit reports, analyze his client’s debts, and how interest rates work in the United States. These were all new concepts for Mark, but learning important industry pratices were independent goals he pursued in order to succeed with the mortgage company.

Mark describes the basic building blocks for business success as excellent communication skills, thoughtful and deliberate actions, and realizing opportunities when they present themselves. In retrospect, had Mark not joined the recreational weekend football league, he would not have met these teammates, and therefore would not have received a job offer.

Mark started as a mortgage loan officer, then became the manager of another branch office. The company published a corporate newsletter where they listed the top mortgage loan officer in the company each year. Mark aspired to become the top mortgage loan officer in the company for the year with a spotlight in the corporate newsletter. In his second year in the mortgage business, Mark set a goal to make $100,000. Mark did everything he could to reach that goal. That same year Mark, became the top mortgage loan officer in the company and earned $101,000.

Mark believes in setting clear goals to help push oneself and visualize success. If you’re in prison and going through this course, you’re listening to the goals of a successful business person. You are learning from leaders that setting clear goals has an enormous influence on what doors open in the future.

After three years working for the mortgage company, Mark decided to open his own mortgage company. Mark approached the owners of his company ask for their help in getting started.  The owners said yes. Mark attributes this positive development to his work ethic, holding himself accountable to the goals he set, and making others aware of his aspirations.

Mark’s mortgage business started with one office in Ohio. Right away, he hired 15 employees. After six years, his business increased to include dozens of employees spread across several mid-western states. He acquired a title company that operated in two states and employed several people. After the 2008 real estate crash, Mark had to downsize his mortgage business.

A reversal of fortune may leave some businesses devasted. In Mark’s case, downsizing led to another opportunity with some of his employees. Mark and his colleagues opened a tax deed business.

Tax deeds are similar to a mortgage foreclosure where property owners lose their property due to their failure to pay taxes. These taxing authorities auction the properties for much less than the property’s value. Mark’s tax deed company helped owners apply to the agency that auctioned their property to recover the excess money for a fee.

According to Mark, the skillsets needed to succeed in any business include:

  • Communication skills;
  • Writing skills;
  • Math skills;
  • Time Management;
  • Organizational skills; and
  • A strong work ethic.

Anyone in prison can develop these abilities using resources that are available. With a deliberate plan and a well-developed menu of skills, people returning to society need not worry about someone giving them a job or earning a livable wage. People can position themselves to create their own jobs and earn their own incomes. Then may even create jobs for other people. This values-based, goal-oriented mindset leads to long-term success.

In addition to owning and eventually selling a cryotherapy business, Mark currently owns three Romeo’s Pizza restaurants. Mark has plans to open a fourth restaurant shortly. Mark turned to Romeo’s Pizza after researching the company. The owner’s excellent communication skills sold Mark on buying a Romeo’s Pizza franchise.

To be successful, Mark believes in the importance of putting oneself around the right kinds of people. When he hires employees at the pizza shop, Mark looks for people that want to make careers with his company. He wants his employees to be the CEO of their lives. Every business owner wants hard-working employees, people who are willing to embrace an entry-level position while aspiring to be the best at their jobs.

People can recreate themselves and their lives by learning from great role models. Consider how lessons from Mark’s achievements might help people advance in their lives. It is not about starting at the top through a sense of entitlement or an unwillingness to put in the work.  Mark kept a slow and steady pace, building incrementally upon each successful step.

Through his diligence and commitment to excellence, Mark achieved financial success. We all can learn from the lessons he offered in the interview segment that accompanies his lesson plan. Exercise patience and humility. Develop strong critical thinking and communication skills.

Critical Thinking Questions:

  • Write at least three paragraphs, with a minimum of three sentences each, for each of the following questions.
  1. How did Mark’s strong work ethic lead to his success?
  2. How do your plans today compare to any past goals you set in your life?
  3. In what ways did setting goals during his early career help Mark create his financial success?
  4. Mark utilized the work ethic he learned from his grandfather and father. What can you learn from any positive role models in your life?
  5. In what ways can you use your time in prison to learn good communication skills?
  6. Mark showed how delayed gratification leads to financial success. In what ways might you do the same in creating a new future for yourself after prison?
  7. What special skills did Mark utilize that helped him succeed in running his own business?
  8. How can creating relationships with positive people create an environment to encourage and aid in our success?
  9. Mark recognized his strength of hard work and learned how to best utilize his skillset. What strengths do you have, and how can you best use them going forward?
  10. In what ways would developing stronger communication skills aid in your post-incarceration development?

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