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 Training Entrepreneurs in Prison 

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Michael Santos

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Course:  Self-Directed, Self-Help with Journaling 101


Title: Training Entrepreneurs in Prison


  • Patrick, an aspiring pilot in his youth, has thrived as an entrepreneur in many industries. He began his career in his passion: aviation. Patrick began his career as a flight manager, though his love of flying led him to become involved in aerial advertisement. Later, he pursued opportunities in real estate, helium extraction, and the natural gas industry. His natural curiosity and willingness to remain open to different opportunities led him to thrive in these distinct industries. Patrick’s life story reflects several tenants of our coursework, including maintaining a formidable work ethic and a positive mindset.


  • Our students should learn the attributes that led to Patrick’s success, such as a willingness to work hard and remain aware of opportunities. Listeners should recognize the importance of developing strong communication, math, and critical thinking skills, all vital for an effective transition to society after their release. Lastly, other important lessons include remaining humble and finding mentors invested in our long-term success.

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 Patrick for sharing his life story with our audience. He is a dynamic leader with a versatile skillset that has enabled his success in distinct industries, such as aviation, aerial advertising, natural resource extraction, and real estate. We learn in this interview how innate curiosity, a strong work ethic, and eagerness to remain aware of opportunities empowered his rise to prosperity.


Growing up, Patrick fostered a keen interest in flying. His desire to navigate the skies led him to earn his pilot’s and aircraft mechanic’s licenses at 17 years old, before he even acquired his driver’s license. As a student, Patrick was a “hands-on” learner who focused solely on academic pursuits that would advance his aspiration to become a pilot. He earned fair grades and “didn’t recognize the value of education,” yet he always studied diligently at flight school despite his lack of interest in academe. Eventually, he completed vocational training at Cornerstone University, a private Michigan institution, hoping to find a long-term job in the aviation industry.

Soon after graduating, Patrick began working as a flight manager supervising five other pilots. This position offered Patrick critical skills and leadership experience, making him more marketable as a pilot. He intended to remain at the firm to attain job security before moving on to more advanced roles later in his career. Long-term job stability appealed to Patrick, a devoted husband and father who sought to provide for his growing family.

However, an unexpected occurrence led Patrick to become a business owner rather than a conventional employee: His firm suddenly closed. Patrick’s employers, likely sensing his

zeal for flying and formidable work ethic, proposed a rare business deal to him to offset his sudden job loss. Namely, they offered Patrick the first right of refusal (the ability to enter a business deal before anyone else can) to purchase the firm’s aviation fleet for nearly $500,000, less than the $700,000 value of the assets, yet still an unattainable sum for Patrick without outside financial aid.

The opportunity to buy the now-defunct company’s aircraft presented Patrick with a unique dilemma. If he agreed to the deal, he faced substantial financial risks and had no guarantee that his new venture would succeed. He would also lack the income stabilityassociated with holding a standard 9-to-5 job, a considerable concern for him as a family man. Yet Patrick remained attracted to the allure of becoming an entrepreneur. He knew that if he succeeded, he stood to earn far higher earnings and enjoy more flexibility than that offered in a typical job.

Patrick accepted his old employer’s offer despite the inherent risk, quipping that “a healthy dose of optimism” was necessary for any successful entrepreneur. His positive outlook helped him overcome significant disadvantages, given that:

  • He lacked meaningful connections – Patrick at first had few contacts with potential clients or business partners who could help him launch his business.
  • He lacked business expertise – Although he had served as a team leader in his previous job as a flight manager, Patrick lacked knowledge in accounting, payroll, marketing, or sales, which are all critical fields for business management.
  • He did not have the finances to buy the aircraft outright – Patrick only had about 30 days of savings stored up when he accepted his old company’s offer. He could not lean on his family to fund his venture, noting that he didn’t inherit wealth from his parents.

Patrick maintained a healthy mindset and work ethic to prevail over these challenges. He vigorously worked to expand his professional network to find an investor willing to finance his new venture. He faced copious rejections as he sought loans from financiers, many of whom doubted the chancesof Patrick’s business succeeding.

Yet Patrick persevered,leading him to find an investor willing to offer him a loan to purchase the air fleet. The terms for the loan were stringent: the investor demanded a high interest rate and reserved the right to seize the aircraft fleet if Patrick defaulted on the loan. Patrick only had a 90-day buffer to begin repaying the amount borrowed, and he was required to pay the entire loan off in 24 months.

Patrick drove his company to earn significant revenue in the following months to ensure its sustainability. His company earned approximately $600,000 the year after he took out the loan. Yet, most of that revenue was spent paying for his company’s operating costs (including his family’s living expenses, his employees’ salaries, gasoline and maintenance of the air fleet, and loan repayments). The following year, the company generated $1.7 million, enough earnings to repay the debt at around the 2-year mark.

The success Patrick experienced led him to pursue more lucrative opportunities later in his career. Now that he had proven his ability to make a business profitable, Patrick could replicate his business model and ensure his future ventures would yield substantial profits.


As I served 9,500 days in prison, I sought to learn from leaders from Patrick to understand what traits fundamental to their character led them to thrive as professionals. If I had heard Patrick’s story while incarcerated, I would have asked him thought-provoking questions to learn the keys to his success.

I’d first want to learn effective methods to improve my communication skills. Throughout our conversation, Patrick demonstrated a high level of clarity and eloquence in his speech. I would have inquired how Patrick developed his strong talent for communication, and I would have engaged in self-directed exercises to improve my ability to convey messages coherently and articulately.  

All our students listening to this message can become more assertive communicators through rigorous self-education. Even while incarcerated, anyone can adopt a reading routine and study reference books, such as dictionaries and thesauruses, to improve their vocabulary. The most successful returning citizens are those who improve their command of written and spoken English ahead of their release. People with such mastery are more capable of persuading others to offer them a job or housing, both crucial steps to successfully transitioning to free society.

Aside from effective communication, we can recognize the need for strong math and critical thinking skills. Patrick relied heavily on both subjects to succeed as a business owner. He had to use basic arithmetic to understand his company’s finances. Simple forms of mathematics, like addition and subtraction, were necessary for Patrick to master to determine how to repay the initial business loan, compensate his employees, and retain enough revenue to take care of his family. Moreover, he had to become a strong critical thinker to make sound decisions to ensure his company’s success, including selecting the best hires and determining which strategies would lead to long-term growth.

In addition, our students should understand the need to adopt a strong work ethic and a positive attitude. Patrick worked countless hours to drive his business endeavor to success. He disavowsus of the misconception that becoming an entrepreneur leads to instantaneous wealth or the freedom to spend doing only the things that we enjoy.

On the contrary, Patrick had to devote considerable time to learn many skills fundamental to business management, such as marketing, accounting, payroll, and client acquisition. He also had to work long hours to keep his business afloat: instead of flying planes all day, he often remained on the ground to manage his firm’s day-to-day operations. Yet rather than complain about the strenuous workload, Patrick remained optimistic because he knew that achieving his long-term goals demanded sacrifice.

  • How do you think Patrick’s optimism led him to succeed in his career?
  • How does Patrick’s belief in optimism inspire you to develop a positive outlook on life?
  • How do you believe Patrick demonstrates strong leadership traits?
  • How do you believe Patrick persuaded an investor to offer him the loan necessary to begin operating his business?
  • How do you believe Patrick’s strong work ethic led him to turn his company profitable in only two years?

Later Career Success

As his career progressed, Patrick became involved in several distinct industries. Our students should reflect on how he remained aware of opportunities throughout his career, leading him to explore and find success in different ventures.

Aerial Advertisement – Patrick’s success in aviation led him to delve into aerial advertisement. This field involves displaying marketing material on planes, blimps, and other aircraft for spectators’ visibility. Businesses use aerial advertising firms like Patrick’s to broadcast their company information in front of a large audience, like at a sporting event. Patrick’s company adopted several advertisement models, including helicopter banners and digital skywriting. He worked arduously to get his business off the ground, estimating that he made up to 200 calls per day to find clients.

Eventually, his diligence paid off. After obtaining clients, Patrick experienced exponential growth in this industry. In 2015, he bought ultralight airships from Switzerland, generating approximately $4 million off this product line after only six months. Two years later, he expanded his business again, buying 15 large, helium-filled airships out of only 21 in the world. In 2019, he estimated his company generated more than $16 million in revenue.

Natural Resource Extraction – The airships Patrick works with need helium, a light gas that lifts the airship off the ground and keeps it airborne. Costs to acquire helium are prohibitively expensive (he estimated spending around $1 million annually for the resource), so Patrick began researching methods to extract the gas at a lower price. After learning that helium is a natural gas product, Patrick started investing in Texas oil and gas wells. He researched the state’s railroad commission, which regulates the natural gas industry, to obtain leases to acquire infrastructure to extract oil and gas in the northern part of the state. His endeavor has already produced a high level of revenue; he estimated earning $8 million last year from the helium business. In the long term, Patrick hopes his investments in natural gas will provide him and his family with a form of passive income. His children can then inherit the money accrued from the business as a form of generational wealth.

Real Estate – Patrick and his wife also invest in real estate, most recently by flipping properties. His wife had long demonstrated an interest in interior design. Patrick encouraged her to channel her passion into a business that renovated older homes and resold those properties for a profit. His children are also involved in some aspects of this business, such as construction. Thus far, he has had “a couple of successful flips” and intends to continue building his real estate portfolio in the long term.

While many of Patrick’s undertakings have succeeded, he has faced failure at different points in his career trajectory. At the end of our dialogue,he tells us that he missed a chance to acquire a dilapidated property seized by a city government at little to no cost. Another entrepreneur later purchased the asset, which held a potential value of several million dollars. Admitting that he missed an opportunity to make a significant profit, Patrick considers the incident a learning experience. Rather than dwell on the loss, he intends to not make the same mistake in the future.


Humility is crucial for self-development. Patrick tells us that he faced several failures in many of his business ventures, yet he sought to learn lessons to avoid making the same mistakes. He consistently has demonstrated a key sign of humility by asking for help when needed.

Closely related to the concept of humility, we learn about the importance of finding mentors. As he explored new concepts, Patrick reached out to experts willing to teach him the best practices for success before he embarkedon a new adventure. His failures earlier in his career led him to recognize that he couldn’t find success on his own, so he found people willing to help him. Remarkably, many of these mentors assisted Patrick without demanding compensation. All our listeners can follow his example by looking for role models and establishing a professional network ahead of their release. Advocacy groups from houses of worship and community centers may offer effective means to find supportive individuals willing to help returning citizens.

Furthermore, we recognize the need for self-education. Before exploring a new investment opportunity, Patrick always engaged in rigorous self-study, including by reading books, watching online videos, and searching for educational content on Google. Notably, he educated himself using free and readily available resources — neither a formal degree nor high tuition costs were necessary for Patrick to become more adept as a business leader. Likewise, even though people in prison or jail lack access to the Internet, they can still freely read hardcover books to learn about subjects that pique their interest.

Lastly, Patrick teaches us the importance of having good judgment and taking calculated risks. As a business leader with a family to support and employees to pay, Patrick knew that any investment he made had to produce a return. He could not afford to lose money on foolhardy pursuits, so he educated himself and thought critically before fully committing to a new business venture.

Similarly, returning citizens must develop sound discernment to make informed decisions that will lead them toward a law-abiding, productive life. All our students should understand the risks involved in selecting friends, deciding where to spend their time, and what behaviors to adopt. To avoid repeat incarceration, our listeners must eschew negative influences and people who promote criminal behavior.

  • How can adopting a self-directed learning routine help you prepare for a career?
  • Why do you believe humility is a beneficial character trait to develop?
  • When and why is it important to ask other people for help?
  • What are effective ways to begin building a support network?
  • What type of characteristics should you seek in people as you build your network?


Patrick should inspire all of us as a success story. He used his passion for aviation to build a lucrative career that generates millions in revenue, provides meaningful work for his employees, and contributes to our community through taxes.

His achievements stem from his eagerness to remain open to new opportunities, learn about unfamiliar subjects, and uphold a rigorous work ethic. He always looked for chances to succeed, even under challenging circumstances. For example, Patrick did not dwell on his misfortune when he lost his first job. Instead, he took advantage of an opportunity to acquire the company’s aircraft fleet and become an entrepreneur. His initial success as a business owner later led him to thrive in other distinct industries, including aerial advertisement, natural resource extraction, and real estate.

Patrick’s innate curiosity and willingness to learn from failure fueled his business success. Before engaging in a new venture, Patrick would educate himself through free and readily available resources. Our students should emulate his example by adopting a self-directed study routine and expanding their math, critical thinking, and communication skills.

He also stressed the importance of remaining humble and seeking help from others. Patrick found mentors to teach him the best practices for success in his different ventures. Likewise, all our students should begin working to find role models and expand their professional networks ahead of their release.

Our team remains committed to fighting mass incarceration, one of this country’s most significant social injustices in the 21st century. Returning citizens will most likely earn their freedom and succeed upon release by adopting a positive outlook, remaining willing to work hard, and improving their skillsets. Patrick offered our team several examples of productive personality traits we should all begin adopting to set ourselves on a pathway to success.

Critical Thinking Questions:

Choose any of three questions below. Write a response for each of the three questions you choose. In your response, please write at least three paragraphs, with a minimum of three sentences each.

This exercise in personal development will help you develop better critical-thinking skills, and better writing skills. There are no right or wrong answers to these questions. We’re striving to learn how to think differently, and how to communicate more efficiently. Try to use some of the vocabulary words from this lesson in your responses.

  1. Why is optimism a common trait among successful people?
  2. How can being optimistic lead you to others to help you find housing or a job ahead of your release?
  3. How do you believe Patrick’s ability to learn from failure enabled him to succeed as a business leader?
  4. How do you think Patrick’s eagerness to learn about unfamiliar topics led him to thrive in different career fields?
  5. Besides the examples already given, how do you believe Patrick relies on his math, critical thinking, and communication skills?
  6. Why are strong communication and critical thinking skills necessary to become a good leader?
  7. In what ways do you believe successful investors like Patrick rely on their math and critical thinking skills?
  8. In what ways do you believe Patrick demonstrates an ability to overcome adversity?
  9. Why is it important to find a mentor ahead of your release?
  10. In what ways could you serve as a mentor or role model for someone else?

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