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 Preparing for Success: Ken 

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Michael Santos

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People in prison need guidance that will help them prepare for success. Ken, a successful entrepreneur, teaches lessons that every person in prison could begin using to build a self-directed pathway to the next stage of life.


Title: Successful Entrepreneur Teaching People in Prison how to Prepare (2021)


  • Ken is a successful entrepreneur who owns a pharmaceutical distribution firm that operates with $150 million in annual revenue. Approximately 20 years ago, he began building his company from scratch. With excellent leadership skills, Ken built the company into a multimillion-dollar enterprise that now employs several dozen staff members. Ken learned the value of hard work early and he maintained a rigorous work ethic throughout his career. He remains successful in business by upholding strong values, such as reliability, integrity, and respect for others.           


  • Students will learn the relationship between a strenuous work ethic, discipline, planning, execution, and integrity relate to business success. Participants will understand how Ken constantly set goals for himself and made incremental progress toward fulfilling his dreams as a young man and later in life. The lesson highlights the importance of developing strong social skills for relationship building and self-advocacy. Lastly, the video outlines the value that comes from developing communication, math, and critical thinking skills. 

Lesson Requirements:

  • Watch the video that accompanies this 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 appreciates Ken’s sharing of invaluable life lessons related to his business success. Over the course of 20 years, Ken began his own wholesale pharmaceutical distributor firm. He began his business with a credit card that had a $25,000 line of credit, and worked from a 90 square-foot office space. Through his diligence and adherence to ethical business values, Ken led his company to grow exponentially.  In recent years, his company has generated more than $100 million in annual sales; lending institutions recognize the value he creates, as evidenced by a $10 million line of credit that they extend. Ken’s firm employs between 30 and 40 sales representatives and retains several ancillary staff members, including attorneys and accountants.  

Participants in our program can grow by listening to the video lesson that accompanies this material. As Ken recounts his achievements, he motivates our audience to follow a deliberate and methodical plan. A strong work ethic leads to prosperity. 


As a child, Ken cultivated a strong work ethic and entrepreneurial spirit. He entered the workforce early, beginning with several manual chores to support his father’s Florida-based tropical fish farming business. He remembers working at the young age of eight. He fondly recalls his father’s adage highlighting the importance of hard work even in the subtropical sun: “Sweat builds character.” Later in his youth, Ken continued honing his work ethic by taking on part-time jobs and starting his own photography business in high school. 

Ken also demonstrated a substantial degree of self-discipline and self-efficacy to set and achieve his goals. He bought his first vehicle before being old enough to drive through the money he earned from his jobs and business. As an adolescent, Ken became interested in aviation, so he offered to wash airplanes at a local airport in exchange for flight lessons. Through this venture, he earned his pilot license at only 18 years old. 

Like many people in our audience, Ken lacked a natural inclination for academics. Still, he personified many of the success principles we teach in our coursework. Ken earned average grades, mostly “Bs” and “Cs,” and he felt unsure whether he wanted to attend college. However, Ken upheld a steadfast dedication to hard work and a goal-oriented mindset as he came of age. 

In Ken’s story, we can identify several pragmatic decisions Ken made as a young man. For example:

  • He attended community college for two years, working part-time jobs at restaurants over the nights and weekends.
  • To avoid student debt and follow in his father’s footsteps, he served in the Air Force for five years. He continued to work part-time and attend college classes even while he was a full-time member of the armed forces.
  • He earned his bachelor’s degree in criminology after seven years of study.


While serving more than 9,500 days in prison, I learned from leaders like Ken. In their stories, I saw examples of people leading a fulfilling, rewarding life. To this day, I admire how Ken avoided an entitlement mentality and refused to blame others for his plight in life. Rather than complaining about not having adequate funds to buy a car or take flight lessons, Ken held multiple jobs and started his own business to earn financial resources and gain experience. Ken attributed his growth to what he learned from strong role models, including his father, who instilled the value of hard work and perseverance in Ken at an early age. 

Similar to Ken, I lacked a proclivity for schoolwork as a young man. Although not seeing the value in studying the esoteric subjects necessary to earn a degree, Ken’s self-motivation in pursuing his business interests and would have inspired me while I served my sentence. Like Ken, many people in prisons or jails lacked interest in academics. They can still adopt a goal-oriented attitude and devotion to hard work to succeed upon their release.

Our students should understand how to define their version of success by setting measurable goals and making incremental progress in fulfilling their dreams. Ken shows us that “the harder we work, the luckier we get” as he consistently identified what he wanted in life and took actionable steps towards success. Incarcerated people should similarly set realistic goals for what they wish to achieve as they reenter society. 

  • Assess how Ken’s experiences in the workforce at a young age contributed to his success later in life?
  • Interpret the expression “sweat builds character?”
  • In what ways could a person in jail or prison apply that concept of building character through difficult situations?
  • Define a goal-oriented attitude?
  • In what ways could applying Ken’s mentality to overcome your challenges?
  • In what ways did Ken’s work ethic help him make up for his lack of interest in academics?
  • Define “entitlement”?
  • In what ways would an entitlement mentality resemble a negative trait

Career Background:

After graduating from college, Ken worked as a probation officer for the state of Florida and later for the Federal system. In that role, he conducted pre-sentence investigations and he monitored people that transitioned to Supervised Release. Ken offers critical insight on how those entangled in the criminal justice system could advocate for themselves. 

During one of his pre-sentencing interviews, Ken encountered a person accused of first-degree murder. Authorities accused this person of killing someone that served time in a jail. Upon the first meeting, the accused left a negative impression on Ken. The man refused to answer questions and he showed signs of a recalcitrant demeanor.  

Ken had hoped to hear some kind of story that may have mitigated the offense conduct. Yet the person’s poor behavior led Ken to accept the prosecutor’s version of events. The person did not offer any details that may have warranted mercy.

In contrast, when people expressed regret, showed empathy, or were forthcoming about their situation, Ken get a better sense of their circumstances. As he reflected, Ken shared that he felt more inclined to help people who were willing to explain, or offer an honest reflection of how they found themselves in their precarious situation. 

Quick Takeaway:

  • Consider the importance of the pre-sentencing investigation and the need to establish rapport with people that have influence or decision-making authority.
  • In what ways would telling an honest story influence possibilities for the best possible outcome from a difficult predicament?
  • How can a person tell a story without justifying previous misconduct?
  • How can a person show lessons learned from past decisions without justifying actions?

Although Ken enjoyed generous benefits as a federal probation officer, he could never satiate his desire to own his own business. Further, the role came with certain risks. When a new business opportunity crossed his plate, Ken felt inclined to take his life in a new direction.

The opportunity opened as a direct result of Ken’s networking skills. For several years, Ken had maintained contact with an acquaintance he knew from his time in the military. That person had built a career as a distributed of pharmaceutical medications. The opportunity piqued Ken’s interest. Although did not have any experience in healthcare, biology, or medicine, Ken clould focus on strengths he had developed over time.

  • Ken had developed outstanding communication skills.
  • Ken understood how to motivate people.
  • Ken had an appreciation for organizational skills.
  • Ken had experience in working with process and standard operating procedures.
  • Ken had a general understanding of business.
  • Ken had cultivated a strong work ethic.

Those personal attributes would lend themselves well to any career and advance prospects for success.

At first, Ken’s obligations with his law enforcement career left him unwilling to break away. He liked the security that came with federal employment. Yet when Ken learned that a person on his caseload had hired a contract killer to murder him, he decided the time had come to make a change.

Rather than making a sudden switch, Ken took incremental steps to change his career. His work as a probation officer incurred too high of a security risk. While on annual leave from his full-time job, Ken began building his business with part-time work as an entrepreneur. He recognized that he had a knack for his new career. Discovering his niche, Ken eventually left his full-time job and dedicated his time solely to his business venture. Fortunately, he enjoyed the support of his wife, who earned a steady paycheck as a teacher. Once the business grew, Ken’s wife left her teaching career to join Ken in building the family-owned business.


Ken teaches us valuable lessons about self-advocacy and relationship building. At Prison Professors, we advise our students to adhere to social norms, such as exhibiting proper decorum while interacting with others, including stakeholders involved in their case. Consider how Ken stated that felt inclined to help people who helped themselves. Story’s like Ken’s inspired me while I served my sentence. From people like him, I learned the importance of preparing self-advocacy plans during my incarceration. I wrote copious letters to the probation office in my district, documenting my journey and my plans for success in the future. This strategy led me to establish rapport with the probation office. I could influence the person who would supervise my release—even before meeting that person. As a result, the probation officer granted higher levels of liberty when I transitioned to society.

Anyone facing a sentencing hearing or preparing to return to society could nurture strong relationships to attain the best possible outcome. Ken fostered relationships with positive influences, such as his wife and acquaintances he met in other areas of his life. By maintaining a connection to a friend from his years in the military, Ken learned about opportunities in the pharmaceutical sector.

A person leaving or prison and jail should similarly seek out relationships with productive, law-abiding members of society. Many people involved in the criminal justice system often find themselves in a perpetual cycle of repeated incarceration by associating with criminogenic individuals and influences.

Critical-thinking questions for any person serving time in a jail or a prison:

  • How can you become a strong advocate for yourself?
  • What behaviors and attitudes should you adopt to influence others positively?
  • Why do you believe Ken felt more willing to help people in his role as a probation officer? 
  • Why might people who refuse to cooperate with probation officers face a harsher sentence?
  • How can you relate to Ken’s desire to switch careers due to his fears for his safety?
  • How can you similarly make changes in your life when faced with danger or negative influences?
  • How do you think Ken’s experience in running a business as a young man led him to become an entrepreneur later in life?
  • How does a person’s work ethic relate to success as a business owner?
  • How can a person foster a strong support network?
  • How can investing time to build communication skills and social mannerisms influence a person’s prospects for success?

Entrepreneurial Success 

Although Ken eventually became successful, he faced myriad challenges in the early days of his new career. Without a background in chemistry, biology, or medicine, Ken was a novice in the pharmaceutical industry. He had to devote long hours to learning the names and pronunciations of different medications. He also had to devise effective strategies to market his new business to suppliers and vendors. Ken often coped with rejection as he would make several hundred cold calls before successfully acquiring one or two suppliers. Despite these difficulties, Ken tenaciously dedicated himself to his endeavors. Fortunately, his wife was “very understanding” of his need to work long hours to invest in their future as a couple. 

Ken imparts valuable lessons on the importance of adhering to a solid value system. His firm enjoys a strong reputation for integrity and reliability based on its ethical practices. Unlike other distributors, Ken’s firm does not replace products with cheaper alternatives and only offers products in its warehouse. In contrast, his competitors have sometimes attempted to sell products that they were still in the process of acquiring. By only offering readily available items, Ken’s firm consistently and promptly delivers products, often ahead of schedule. This sound business practice has helped Ken’s firm retain clients, including many that began working with the company in its nascency.

As his business grew, Ken hired employees and delegated duties to his support staff. He eventually established a hierarchy amongst these new employees, including sales managers, sales representatives, and team leaders. As his business continued to grow, Ken implemented standard operating procedures to ensure his employees understood their roles and responsibilities. 

We learn several notable lessons about Ken’s firm and hiring practices:

  • His firm is looking for motivated individuals. Some of the more tenacious and hard-working sales representatives at his firm earn more than $1 million per year in commissions.
  • His firm is not restricted from hiring people with criminal records as sales representatives.
  • Some employees lack a college degree yet are among his best performers.

These facts lead us to infer that a person reentering society could look at any company as a possible venue for success. Business owners will hire people that can perform on the job and generate results; a person that prepares himself well while serving a prison term can build a story. That story can open possibilities, even in the most unlikely industry.

Ken also shares insight on the importance of developing strong skills in math, communications, and critical thinking. An incarcerated person aspiring to become an entrepreneur like Ken must grasp basic math to understand concepts, such as a profit and loss statement, balance sheets, and income statements. Similarly, Ken depends on his strong communication skills to attract and retain clients and mentor his employees.

An incarcerated person seeking employment or attempting to build a business must learn to communicate goals to persuade others. Lastly, Ken relies on strong critical thinking skills, as seen in his selection of positive influences and associates. Likewise, someone leaving prison or jail will need to discern the best ways to build a support network. A prudent person would begin building that support network immediately and continue the effort throughout life.


While I served my term in prison, role models like Ken inspired me to improve myself and prepare to prosper upon release. Anyone could learn the same lessons. A story like Ken’s motivated me to work toward earning multiple degrees and to become a published author from inside prison boundaries. I worked on my diction, my critical-thinking skills, and tried to develop a social etiquette to ensure that no one would know that I had served a day in prison had I not revealed my past.

An important lesson throughout Ken’s story is the importance of developing a strong vocabulary. Ken had to build a new lexicon to understand terms in the pharmaceutical industry. Likewise, a person leaving prison or jail must refine their speech patterns and word choices. To prosper in free society, a formerly incarcerated person should avoid using prison-related slang or profanity, as these actions may stigmatize a person, and obliterate rather than open opportunities. Additionally, people transitioning into a new career must learn industry-specific jargon to communicate effectively with others in their field. 

Ken’s story reminds us that learning goes beyond earning a credential. Many people erroneously believe that they have completed their formal education once they earn a GED, a high school diploma, or a college degree. To become a wealthy entrepreneur like Ken requires a person to master the materials taught in school; a person must also apply theoretical concepts in everyday life. Education is not a substitute for hard work or talent. Ken shared that many of his best employees lacked a college education while many who had earned their degrees failed to satisfy his company’s needs. As a result, Ken’s company stopped requiring candidates to hold four-year degrees and now judges candidates by their attitude, their aptitude, and their motivation to learn.

From those lessons, a person in jail or prison might consider the following questions as an exercise in critical thinking:

  • In what ways would Ken’s ethical business practices distinguish him from competitors?
  • What do reputations of integrity and reliability say about employees and businesses?
  • What character traits do you believe Ken’s most successful employees possess?
  • How would foul language and prison-related slang influence prospects for success?
  • Why is it important to constantly refine and broaden vocabulary?

The Power of Motivation:

Ken shared how the right attitude and motivation to work can attract positive attention. For example, a hard-working young man who operated a car detailing business from his home made a favorable impression on Ken. Around five years ago, Ken offered the individual an inexpensive lease for a warehouse. Ken also shared advice on best practices for hiring good employees and selecting accounting systems. By adhering to Ken’s mentoring, the young man stewarded his business’ growth. The company that Ken helped to incubate now employs multiple people involved in several complex detailing and car restoration procedures.

From this story, we can infer that if a person exhibited the same positive mindset and diligence, he could inadvertently persuade others to help them. On a personal level, I can say that people like Ken stepped in to help me build my career after authorities released me from 26 years in prison.

In what ways can you begin sowing seeds today, to put you in a better position to receive help tomorrow?

Critical Thinking Questions:

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

  1. How would building good communication and relationship-building skills lead to a favorable outcome upon release?
  2. How can you develop a good judgment of character?
  3. How can discerning the character of others help you establish a strong support network as you leave jail or prison?
  4. How can a sales representative role be a viable career path for you?
  5. How can a commissions-based role lead you to a lucrative career?
  6. What are effective ways to communicate with probation officers, law enforcement officials, and other influential stakeholders involved in your case?
  7. What attitudes or actions should a formerly incarcerated person avoid?
  8. How can journaling be a productive exercise in your current situation?
  9. How can you adopt this habit to document your plans for success upon release?
  10. What self-directed exercises can you adopt now to improve your math, communication, and critical thinking skills?
  11. How can you set incremental goals and plans to leave an unfavorable situation, such as a dangerous environment?
  12. Why does education mean more than earning a credential?
  13. Why is it necessary to master the concepts taught in school rather than simply pass a course?
  14. Why is it important to remain motivated while on the job or while starting your own business?
  15. How can maintaining a diligent work ethic and motivated attitude persuade others to help you upon your release?

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