Success after Prison: Master Class-Phil 

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



Title: Success after Prison Master Class: Phil


  • Phil’s story is a powerful tale of overcoming adversity through resilience and education. Born into poverty, he faced family mental health issues and constant relocations. Despite these challenges, Phil’s intellectual brilliance and work ethic led him to academic and professional success. A first-generation college graduate, he pursued law, driven by a passion for social justice, and later excelled in the insurance industry. His journey offers inspiring lessons in perseverance, adaptability, and self-education.


  • The lesson objectives focus on instilling resilience, promoting a strong work ethic, encouraging self-education, and embracing the power of mentorship. Through Phil’s story, students learn to overcome adversities, adapt to life’s changes, value continuous learning, and draw inspiration from role models. The lesson plan aims to equip audience members with the tools and mindset needed to navigate their personal and professional journeys successfully.

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.

At Prison Professors, our mission extends beyond mere guidance – we bring to life extraordinary stories of perseverance and achievement to inspire our community of more than 300,000 students across the nation. We believe in the transformative power of real-life examples, sharing the stories of individuals who faced significant challenges and emerged triumphant. Our goal is to empower our audience with the insights and strategies of these remarkable journeys, assisting them as they endeavor to rebuild and reshape their lives.

Phil’s story is an archetype of our mission. Transitioning from poverty as a child to unprecedented heights in sales, his narrative is a testament to the indomitable human spirit. Phil’s life, marked by adversity, resilience, and a relentless pursuit of excellence, should inspire all our students. His journey demonstrates the importance of adaptability, tenacity, and the lifelong pursuit of knowledge. More than just a success story, Phil’s path provides practical lessons and strategies for anyone determined to overcome obstacles and chart a course toward a brighter, more successful future.


Born into poverty, Phil’s childhood in Chicago was the crucible that forged his unyielding spirit. He vividly recalls, “My family was on welfare,” adding that his household subsisted on food stamps all through his high school years. These privations poignantly illustrate the obstacles he endured as he came of age.

Aside from financial hardships, Phil also endured numerous relocations as a child in the aftermath of his parents’ divorce. Initially, he and his brother moved from Chicago to Los Angeles with their mother. However, the siblings moved back to live with his father in later years. As a teenager, Phil attended high school and college in Southwestern Michigan.

Compounding Phil’s struggles were his father’s mental health challenges. Suffering from paranoid schizophrenia, his father was institutionalized, casting a profound influence on Phil.

This experience likely deepened Phil’s empathy and understanding of the complexities of mental health. Living with his father during these formative years honed Phil’s ability to develop compassion for those facing personal challenges.

Amid these hurdles, Phil relied on his exceptional intellectual brilliance to overcome the odds. Blessed with a photographic memory, he excelled academically, his achievements standing in stark contrast to his family’s financial struggles. “I was an extremely good student… and I also developed an extremely hard work ethic,” he reflects, highlighting the sanctity he placed on education. For our students, his experience highlights how expanding our knowledge and broadening our skill sets can lead us to a brighter future.

Having excelled academically, he became the first person in his family to earn a four-year degree, graduating from a small affluent college in Western Michigan. Unlike his peers, who hailed from prestigious and wealthy families, Phil recalled being on more financial aid than any other student at the institution. Yet Phil never doubted his self-value, seeing education as a means to break the generational cycle of poverty. His journey reminds us that we, too, can achieve significant milestones despite our pasts.

Phil nurtured a passion for law, influenced by his father and inspired by legal luminaries like F. Lee Bailey and William Kunstler. He attended Stetson University College of Law in St. Petersburg, Florida, known for its strong trial advocacy program. Unlike other students, he maintained outside employment for the duration of his studies to offset the financial burden. Demonstrating a tenacious work ethic, he worked full-time in the insurance business even while enrolled as a full-time student. For our audience, his determination offers a clear message: Success requires unrelenting dedication. To thrive upon reintegration, we must be willing to put forth strenuous effort as we pursue our goals.

Law offered more than a career for Phil; it also provided him with a means to fight for societal change. Upon graduating, Phil completed a formative internship in the homicide division of the State Attorney’s Office in Philadelphia, reshaping his worldview and solidifying his interest in civil rights and justice. In 1979, his relocation to Florida exposed him to the harsh realities of racial prejudice within the legal system, catalyzing his commitment to advocacy and social justice.

Aiming to fight for a just cause, Phil adopted a fearless approach to challenging systemic injustices. Reflecting on his commitment, Phil reflected: “I took a stand against … racism and… the use of the justice system to overwhelm people who did not have even odds.”

In a notable case, Phil advocated for a woman who had been unjustly imprisoned for 25 years for the murder of her abusive husband. This case was a striking example of the justice system’s failures, particularly highlighting the impact of judicial misconduct. The presiding judge, struggling with alcoholism, failed to ensure a fair trial, leading to the woman’s wrongful conviction.

Refusing to remain passive, he petitioned the Supreme Court of Florida to correct the miscarriage of justice. Eventually, the woman was exonerated, proving that resilience and relentless advocacy can bring justice, even in seemingly hopeless situations. This triumph not only accentuated the importance of challenging systemic flaws but also highlighted Phil’s commitment to fighting for those in unfortunate situations.

Yet Phil’s confrontational approach did not come without consequences. Having gained a reputation as a firebrand, one of his peers cautioned Phil, tersely asking him: “You don’t want to be a lawyer very long, do you?”  These words were prescient. After publicly criticizing a high-level judge, the bar association essentially invited him to leave the legal profession as a result of his outspokenness.

In need of a new career, Phil returned to insurance sales, a transformative venture that led him to generate substantial wealth and provide livelihoods for deserving employees. Reflecting on his rapid ascent in insurance, “I had enough success that I couldn’t practice law… because I couldn’t afford to take the pay cut.” For our students, Phil’s reflection uncovers a crucial insight: By seizing new opportunities, we can thrive beyond what we perceive as possible despite past hardships or disappointments.


At Prison Professors, we are committed to positively impacting the lives of justice-impacted individuals nationwide by imparting the knowledge and experiences of role models like Phil. As I spent nearly 10,000 days in prison, I looked for mentors who could provide insight into the success principles that would empower me to thrive upon release. Phil is an example of such a leader. He offers crucial lessons related to resilience, a robust work ethic, self-learning, and emulation of role models.

Be Resilient: Phil’s story is a powerful illustration of the strength of resilience in the face of adversity. His journey, marked by poverty, family mental health challenges, and life-altering transitions, teaches us a vital lesson: our circumstances do not have to dictate our destiny. His ability to thrive despite these hurdles illustrates the power of perseverance. For students, Phil’s experience reinforces the belief that with resilience and determination, overcoming life’s challenges is a means of paving the way for a brighter, more successful future.

Avoid Self-Pity: Closely related to his resilience is Phil’s rejection of self-pity and embrace of personal accountability. Throughout his life, he prevailed against outwardly insurmountable challenges by refusing to succumb to a victim mentality. He financed his education by working full-time, never allowing financial constraints or his modest upbringing to hinder his academic success. As a lawyer, he fought against pervasive corruption in a behemoth justice system, refusing to be defeated even against massive odds. For our audience, a crucial lesson emerges: We must adopt a proactive and determined attitude, viewing challenges not as insurmountable barriers, but as opportunities to demonstrate our strength, resolve, and capacity for change.

Maintain a Rigorous Work Ethic: His story illuminates the significance of a solid work ethic. Facing extreme challenges as a young man, Phil didn’t yield to adversity. Instead, he harnessed his exceptional memory and academic prowess to excel in school, setting the stage for his future successes. As a young adult, he showed the same commitment, balancing the rigors of law school with full-time work in the insurance industry, a feat that highlights his extraordinary discipline and resilience. Phil’s approach teaches us that persistence, coupled with a solid work ethic, is the key to unlocking one’s potential and achieving ambitious goals.

Educate Yourself: Phil firmly believes in the transformative power of self-education. He emphasizes how self-learning is a crucial means of empowering individuals, especially those from disadvantaged backgrounds, to reach their goals. He encourages our audience members to broaden their knowledge by becoming autodidacts. We should use any resources at our disposal—books, magazines, or newspapers—to become more knowledgeable about careers, trends in technology, and societal change ahead of reintegration.

Embrace Role Models: Phil’s life illustrates the significant influence of role models in guiding and inspiring change. He mentions several renowned leaders who personally impacted his worldview and approach to life. Among the eminent figures he met were Tony Bennett and Coretta Scott King, two individuals who, beyond leaving him starstruck, deepened his understanding of perseverance and advocacy. Yet his role models went beyond those he personally encountered; he also read about prominent figures in history—ranging from Nelson Mandela to Martin Luther King, Jr.—absorbing their stories and lessons. Their influence is a vivid reminder that we, too, can draw strength and guidance from the lives and teachings of those who have paved the way before us. For our students, embracing such role models can be a source of motivation and a roadmap for personal growth and societal contribution.

  • How can Phil’s journey from poverty to professional success inspire you to overcome your current challenges?
  • In what ways can Phil’s experience of adapting to different life changes be applied to your situation in overcoming obstacles?
  • How can you utilize Phil’s belief in the importance of education and self-improvement to shape your path forward?
  • Reflecting on Phil’s ability to empathize with others due to his personal experiences, how can you turn your own experiences into strengths?
  • Considering Phil’s advocacy against judicial misconduct, what steps can you take to advocate for justice and change within your own community or situation?


Phil’s journey in the insurance industry is a masterclass in adaptability, leadership, and a relentless pursuit of excellence. He made a rapid ascent in the field, establishing a name for himself as one of the top producers of annuity sales in the United States. His success stemmed from his ability to connect with clients and communicate the value of what he was selling effectively. Phil once articulated, “In sales, it’s not just about knowing your product… but about how it can help the person you’re trying to reach.” His message instills in us the importance of empathy and meeting others’ needs.

His entrepreneurial spirit also shone through as he established a large insurance agency and distribution center. This venture reflected his knack for strategic planning, operational management, and leadership. He went beyond excelling in sales; he built a robust team, fostered a positive work environment, and managed complex business processes. Phil knew the importance of building strong customer relationships and innovating his approach to sales.

Not content with his own success, Phil strove to build up others. He emerged as an influential educator and mentor within the industry. He authored a book on retirement planning and the extensive training he provided to hundreds of insurance agents across the nation. Many of these agents, under Phil’s tutelage, went on to achieve significant success in their careers.

Under his leadership, his team managed nearly a billion dollars in life insurance coverage, proof of Phil’s exceptional management skills and financial acumen. His aptitude for team leadership, client trust, risk management, and operational efficiency was evident in every facet of his business dealings.

Phil’s approach to his career was characterized by continuous learning and growth. He adapted to market changes, enhanced his skills, and maintained a competitive edge. He believed in the power of education, as he once noted, “Anybody can become an expert… through self-study.” His commitment to personal and professional development propelled his success and fostered a learning culture within his organization.

For our students, particularly those eyeing entrepreneurial pursuits, we can glean several business insights from Phil:

  • Market Understanding: Recognizing the unique challenges of different environments is crucial. Phil’s emphasis on adaptability in business, such as his analogy of focusing on heating in Michigan and air conditioning in Florida, reflects the versatility required to succeed in different circumstances. Challenge yourself to identify and meet the unique needs of your environment.
  • Diverse Industry Insights: Phil’s success across various sectors illustrates the advantage of having a broad perspective. It highlights how individuals with diverse life experiences can explore different career paths, using their unique backgrounds to pivot and adapt effectively. Seek to diversify your knowledge and experiences for broader career options.
  • Customized Marketing: Adapting strategies to different audiences is a skill applicable beyond business. Phil’s approach to marketing mirrors how individuals can tailor their presentations and narratives to resonate with diverse groups and potential opportunities. Tailor your approach to fit the unique characteristics and needs of your target audience.
  • Innovative Approaches: Creativity and innovation are key to finding new opportunities. Phil’s innovative spirit in exploring niche markets can inspire those seeking to carve out new paths for themselves, regardless of their past. Be bold in exploring creative solutions and new avenues.
  • Risk Management: Navigating risks is essential in both business and life. Phil’s method of evaluating risks in new ventures provides a model for making informed decisions when facing challenges and opportunities. Adopt a risk-aware approach in your endeavors to make balanced decisions.
  • Learning from Experiences: Gleaning insights from both successes and failures is fundamental for growth. Phil’s career, based on his willingness to learn from others’ examples, serves as a reminder to view all life experiences as valuable teaching moments. Embrace every experience as a chance to learn and grow.


Phil’s journey in the insurance industry offers vital lessons for overcoming challenges and achieving success. His story highlights the importance of effective communication, embracing rejection, offering value, and learning from others. Let’s dive into these takeaways and see how they can be applied in our lives.

Become an effective communicator: Phil’s remarkable journey in the insurance industry highlights the power of effective communication, a skill that can be developed in anyone. His conviction that “Great salespeople are not born but developed” is enlightening for our audience. By honing communication skills, we can transcend barriers, forge meaningful relationships, and unlock new opportunities. Remember Phil’s words: “The number one thing… is communication. The art of communication.” Sharpen your communication skills to build trust, understand others’ needs, and create new possibilities.

Accept Rejection Gracefully: Accepting rejection gracefully is a critical lesson from Phil’s experiences in the insurance industry. His resilience in the face of high rejection rates and various challenges stands as a testament to his perseverance and strength. For our listeners, Phil’s journey illustrates the importance of viewing rejection as a vital opportunity for growth and self-improvement. Embracing challenges with a positive mindset and unwavering courage is key to overcoming obstacles and achieving success. Take inspiration from Phil’s story and approach your next challenge with the understanding that each rejection is a step toward growth. Reflect on your experiences, learn from them, and use this knowledge to forge a path toward your goals. Remember, every ‘no’ brings you closer to a ‘yes.’

Always Deliver Value: Phil’s strategy of providing value through complimentary services or products is a lesson in strategic generosity, particularly relevant for those working to rebuild their lives. Understanding the allure of “free,” Phil suggests using this approach as a ‘loss leader,’ offering initial services at no charge to demonstrate quality and establish trust with potential customers. This method isn’t about devaluing one’s work but rather showcasing commitment and excellence, creating a foundation for future business. For anyone striving to re-establish themselves professionally, this technique can be a game-changer. It’s an opportunity to highlight your skills and work ethic, fostering trust-based relationships and paving the way for future success. Embrace Phil’s philosophy of offering initial value as a stepping stone to building a solid professional reputation. Explore this approach in your next venture to establish credibility and long-term opportunities.

Learn from Others: Learning from others’ experiences is a crucial lesson emphasized in Phil’s journey. He passionately believed in the value of absorbing knowledge from those around him, once saying, “I would suck their brain dry for knowledge.” This approach is particularly meaningful for our listeners. It underscores the importance of seeking guidance from those who have navigated similar paths. Phil’s philosophy suggests that embracing mentorship and being open to learning from others can significantly accelerate personal and professional development. For our students, this means actively seeking out mentors and role models, engaging in conversations, asking questions, and being receptive to the lessons these interactions offer. Consider every interaction as an opportunity to learn and grow. Your willingness to learn from others can be a defining factor in your journey toward success and fulfillment.

  • How can Phil’s approach to overcoming financial constraints and finding success in the insurance industry inspire your own career pivot?
  • In what ways can you apply Phil’s belief in the power of personal growth and effective communication to your life and career goals?
  • How can Phil’s success in building relationships and closing deals in sales inspire you to improve your interpersonal skills?
  • What lessons can you learn from Phil’s emphasis on team welfare and its impact on business success?
  • How can Phil’s experience in mentoring and leading others in the insurance industry guide you in your journey toward leadership and personal development?


Phil’s remarkable rise from childhood poverty to professional acclaim is a story of resilience and hope. Overcoming financial struggles, family instability, and the impact of his father’s mental health issues, Phil’s adversities forged his tenacious and compassionate spirit.

His educational achievements led him to be the first in his family to graduate college. Driven by a quest for social justice, he attended law school, juggling intense studies with full-time work. Phil’s legal career, defined by his commitment to fighting judicial misconduct and inequality, eventually gave way to a pivot into the insurance industry. In this new realm, Phil’s adaptability and entrepreneurial acumen shone, proof of his talents in building connections, communication, and leading with empathy and integrity.

Phil’s life story is more than a narrative of overcoming obstacles; it is a powerful lesson in the transformative impact of education, resilience, and self-empowerment. His experiences teach us that our circumstances do not define our potential and that challenges can be transformed into opportunities for growth.

Reflect on an instructive quote from our guest: “Anybody can achieve anything they want to achieve, you just have to put your mind to it.” This statement is more than just an axiom; it is a clarion call to all our students, a reminder that the power to change our circumstances lies within us. Phil’s journey shows us that with unwavering determination and a commitment to self-improvement, no hurdle is insurmountable.

In addition to Phil’s inspiring journey and the valuable insights shared throughout this document, we have compiled a series of appendices to further support your learning and application of the principles outlined

  • Appendix A: Glossary
  • Appendix B: Skill Development
  • Appendix C: Ten Coursework Modules
  • Appendix D: Replicating Phil’s Success
  • Appendix E: Biographical Sketches
  • Appendix F: Related Reading and Resources
  • Appendix G: Advocacy Organizations
  • Appendix H: Potential Careers

In the spirit of Phil’s journey, we urge you to take a stand in your own livesHarness the power of resilience, education, and unwavering dedication. Let Phil’s story serve as a reminder that no matter our starting point, we can author our own stories of success and leave a lasting, positive impact on the world.

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.

General Questions:

  1. How can Phil’s ability to transform his early life hardships into driving forces for success inspire you to reshape your personal challenges into opportunities?
  2. In what ways can you emulate Phil’s approach to adapting to life’s changes, especially when facing unexpected turns in your own journey?
  3. Considering Phil’s success despite his unconventional background, how can you redefine your past experiences as strengths rather than limitations?
  4. How can Phil’s persistence in the face of family adversity inspire you to approach your familial challenges with resilience and compassion?
  5. Reflecting on Phil’s transition from a troubled childhood to a successful career, how can you use your life experiences to fuel your ambitions?
  6. How can Phil’s story of overcoming financial and educational barriers motivate you to find creative solutions to your own financial challenges?
  7. Given Phil’s journey of personal development amidst adversity, how can you cultivate a mindset of growth and self-improvement in your current situation?
  8. How can Phil’s experience of rebuilding his career path after setbacks inspire you to view your own setbacks as new beginnings?
  9. In what ways can Phil’s story encourage you to embrace and seek out mentorship as a tool for personal and professional growth?
  10. How can Phil’s commitment to continuous learning and adaptation guide you in navigating the changing landscapes of your own life and career?

Related to Math, Critical Thinking, and Communication:

  1. Reflecting on Phil’s success in various fields, how can you apply mathematical skills to better manage and overcome financial challenges in your life?
  2. How can Phil’s story inspire you to use critical thinking to identify and solve complex problems in your personal or professional life?
  3. How can you use critical thinking to analyze and learn from your past experiences, much like Phil did throughout his journey?
  4. In what ways can you employ critical thinking to evaluate opportunities and challenges, drawing inspiration from Phil’s approach to navigating life’s hurdles?
  5. Considering Phil’s ability to adapt in diverse environments, how can you use mathematical reasoning to make more informed decisions in uncertain situations?
  6. How can Phil’s effective communication in his career inspire you to improve your own communication skills for better personal and professional relationships?
  7. How can you apply critical thinking to evaluate opportunities and challenges, drawing inspiration from Phil’s approach to navigating life’s hurdles?
  8. In what ways can you use communication skills to advocate for yourself and others, taking a cue from Phil’s advocacy in the legal field?

Appendix A: Glossary

  • Accelerate (verb) – To increase in speed or rate.
  • Accentuate (verb) – To emphasize or highlight.
  • Acclaim (noun) – Praise enthusiastically and publicly.
  • Acmuen (noun) – The ability to make good judgments and quick decisions.
  • Affluent (adjective) – Wealthy or rich.
  • Analogy (noun) – A comparison between two things for the purpose of explanation or clarification.
  • Annuity (noun) – A fixed sum of money paid to someone each year, typically for the rest of their life.
  • Applicable (adjective) – Relevant or appropriate.
  • Aptitude (noun) – A natural ability to do something.
  • Archetype (noun) – A very typical example of a certain person or thing.
  • Autodidact (noun) – A self-taught person.
  • Axiom (noun) – A statement or proposition that is regarded as being established, accepted, or self-evidently true.
  • Behemoth (noun) – Something enormous, especially a big and powerful organization.
  • Broaden (verb) – To expand or extend.
  • Catalyze (verb) – To cause or accelerate a reaction or change.
  • Clarion Call (noun) – A strongly expressed demand or request for action.
  • Compound (verb) – To make something worse; intensify the negative aspects of.
  • Crucible (noun) – A situation of severe trial, or in which different elements interact, leading to the creation of something new.
  • Diversify (verb) – To make or become more diverse or varied.
  • Emerge (verb) – To become apparent, important, or prominent.
  • Eminent (adjective) – Famous and respected within a particular sphere.
  • Empathy (noun) – The ability to understand and share the feelings of another.
  • Empower (verb) – To give someone the authority or power to do something.
  • Endeavor (noun) – An attempt to achieve a goal.
  • Entrepreneurial (adjective) – Characterized by the taking of financial risks in the hope of profit; enterprising.
  • Excel (verb) – To be exceptionally good at or proficient in an activity or subject.
  • Exonerate (verb) – To absolve someone from blame for a fault or wrongdoing.
  • Feat (noun) – An achievement that requires great courage, skill, or strength.
  • Firebrand (noun) – A person who is passionate about a particular cause, typically inciting change and taking radical action.
  • Flaw (noun) – A mark, fault, or other imperfection that mars a substance or object.
  • Formative (adjective) – Serving to form something, especially having a profound influence on a person’s development.
  • Glean (verb) – To extract information from various sources.
  • Gracefully (adverb) – In an elegant and graceful manner.
  • Harness (verb) – To control and make use of (natural resources), especially to produce energy.
  • Hinder (verb) – To create difficulties for someone or something, resulting in delay or obstruction.
  • Hurdle (noun) – An obstacle or difficulty.
  • Illuminate (verb) – To light up; make clear or understandable.
  • Illuminating (adjective) – Providing insight, clarity, or understanding.
  • Imminent (adjective) – About to happen.
  • Indomitable (adjective) – Impossible to subdue or defeat.
  • Integrity (noun) – The quality of being honest and having strong moral principles.
  • Knack (noun) – An acquired or natural skill at performing a task.
  • Livelihood (noun) – A means of securing the necessities of life.
  • Luminary (noun) – A person who inspires or influences others, especially one prominent in a particular sphere.
  • Masterclass (noun) – A class given to students of a particular discipline by an expert of that discipline.
  • Milestone (noun) – An important stage or event in the development of something.
  • Miscarriage of Justice (noun) – A wrong judgment, whereby an innocent person is convicted and a guilty person is acquitted.
  • Navigate (verb) – To plan and direct the course of a vehicle, or find one’s way.
  • Niche (noun) – A comfortable or suitable position in life or employment.
  • Nurture (verb) – To care for and encourage the growth or development of.
  • Perseverance (noun) – Persistence in doing something despite difficulty or delay in achieving success.
  • Petition (verb) – To make a formal request to an authority with respect to a particular cause.
  • Photographic Memory (noun) – The ability to remember information or visual images in great detail.
  • Pivot (verb) – To turn or rotate, like on a pivot.
  • Poignantly (adverb) – In a way that evokes a keen sense of sadness or regret.
  • Pervasive (adjective) – Spreading widely throughout an area or a group of people.
  • Prescient (adjective) – Having or showing knowledge of events before they take place.
  • Prowess (noun) – Skill or expertise in a particular activity or field.
  • Quest (noun) – A long or arduous search for something.
  • Realm (noun) – A kingdom; a field or domain of activity or interest.
  • Reinforce (verb) – To strengthen or support.
  • Renowned (adjective) – Known or talked about by many people; famous.
  • Resilience (noun) – The capacity to recover quickly from difficulties; toughness.
  • Robust (adjective) – Strong and healthy; vigorous.
  • Rigor (noun) – The quality of being extremely thorough, exhaustive, or accurate.
  • Sanctity (noun) – The state or quality of being holy, sacred, or saintly.
  • Self-Pity (noun) – Excessive, self-absorbed unhappiness over one’s own troubles.
  • Self-Value (noun) – The sense of one’s own worth or importance.
  • Siblings (noun) – Each of two or more children or offspring having one or both parents in common; a brother or sister.
  • Starstruck (adjective) – Fascinated or greatly impressed by famous people, especially those in the entertainment industry.
  • Stark (adjective) – Severe or bare in appearance or outline.
  • Strenuous (adjective) – Requiring or using great exertion.
  • Striking (adjective) – Attracting attention by reason of being unusual, extreme, or prominent.
  • Subsist (verb) – To maintain or support oneself, especially at a minimal level.
  • Succumb (verb) – To fail to resist pressure, temptation, or some other negative force.
  • Systemic (adjective) – Relating to a system, especially as opposed to a particular part.
  • Tenacity (noun) – The quality or fact of being very determined; determination.
  • Tersely (adverb) – Briefly and clearly expressed.
  • Thrive (verb) – To grow or develop well or vigorously.
  • Transcend (verb) – To go beyond the range or limits of something.
  • Tutelage (noun) – Protection of or authority over someone or something; guardianship.
  • Unwavering (adjective) – Steady or resolute; not wavering.
  • Venture (noun) – A risky or daring journey or undertaking.
  • Vital (adjective) – Absolutely necessary; essential.
  • Vivid (adjective) – Producing powerful feelings or strong, clear images in the mind.

Appendix B: Skill Development

In this appendix, we delve into the crucial skills that Phil mastered throughout his remarkable journey, which played a pivotal role in his success. From math and financial management to critical thinking and communication, Phil’s application of these skills in various scenarios provides invaluable lessons for personal and professional growth. Below, we outline exercises designed to develop these skills, drawing inspiration from Phil’s experiences and approaches in overcoming challenges and achieving success in his career. Let’s explore how these skills were manifested in Phil’s life and how you can cultivate them through practical exercises.

Skill AreaExplanation
MathFinancial Management and Planning: Throughout his career in insurance, Phil applied math skills in budgeting, financial planning, and managing large-scale business operations. Understanding complex financial concepts was crucial, especially in managing nearly a billion dollars in life insurance coverage.Sales Analysis and Forecasting: In his role as a top producer of annuity sales, Phil used math to analyze sales trends, forecast future performance, and make data-driven decisions to optimize sales strategies.Insurance Product Understanding: His proficiency in math helped Phil understand and explain the intricate details of insurance products, particularly annuities, to his clients and team.
Critical ThinkingStrategic Planning and Problem-Solving: Phil demonstrated critical thinking in developing and executing strategies for his large insurance agency and distribution center. He identified market opportunities, assessed risks, and devised solutions to operational challenges.Legal Analysis and Advocacy: As a lawyer, Phil’s critical thinking was essential in dissecting complex legal cases, formulating arguments, and advocating for justice, as evidenced in his work challenging judicial misconduct and fighting for civil rights.Innovative Business Approaches: Phil’s ability to think critically allowed him to innovate within the insurance industry, finding unique ways to connect with customers and expand his business.
CommunicationSales and Customer Relations: Phil’s success in sales hinged on his exceptional communication skills. He effectively articulated the benefits of insurance products, building trust and relationships with clients.Leadership and Team Building: As the head of a large agency, Phil’s communication skills were key in leading, motivating, and training his team, fostering a positive work environment and a culture of learning.Education and Mentorship: Phil’s role as an educator and mentor in the insurance industry showcased his ability to communicate complex concepts clearly and effectively, as seen in his book on retirement planning and training programs for insurance agents.

Math Exercises:

Insurance Agency Budget Management Exercise:

Scenario: Phil is expanding his insurance agency with a budget of $20,000.

Task: Allocate this budget across various business expenses.

  • Office Space: Choose between a $3,000/month standard office or a $5,000/month premium location.
  • Sales Team Training: Allocate up to $4,000 for team development and training.
  • Marketing: Decide how much to spend on marketing (up to $4,000).
  • Operating Expenses (utilities, software, etc.): Budget the remaining funds.
  • Objective: Create a balanced budget that covers all essential areas without exceeding the $20,000 limit. Include a contingency plan for an unexpected insurance licensing fee of $2,000.

Annuity Sales Return Analysis Exercise:

Scenario: Phil is considering two different annuity products for his clients.

Task: Calculate and analyze the potential returns from a $10,000 investment in each annuity.

  • Step 1: Calculate the return for each annuity (Annuity A: 10% projected return, Annuity B: 8% return with higher stability).
  • Step 2: Write an analysis weighing the returns against the risks, reflecting Phil’s decision-making process in selecting products for his clients.

Critical Thinking Skills Exercises:

Insurance Market Trend Analysis:

Task: Analyze current trends in the insurance market to identify opportunities and challenges.

  • Step 1: List three current trends in the insurance industry.
  • Step 2: For each trend, identify potential opportunities and challenges for an insurance agency.
  • Objective: Develop insights into the insurance market, similar to how Phil adapted his business strategies in response to market changes.

Agency Growth Strategy Case Study:

Scenario: An insurance agency is struggling to expand its client base.

Task: Identify issues and propose solutions.

  • Step 1: Suggest three potential reasons for the stagnation in growth.
  • Step 2: Propose two actionable strategies for each identified issue.
  • Objective: Formulate strategic responses to business growth challenges, inspired by Phil’s approach in expanding his agency.

Communication Skills Exercises:

Client Consultation Role-play:

Task: Prepare a consultation session with a potential insurance client.

  • Step 1: Outline the client’s needs and potential insurance products.
  • Step 2: Practice delivering the consultation, focusing on clarity, empathy, and persuasiveness.
  • Objective: Enhance the ability to communicate complex insurance products effectively, mirroring Phil’s success in connecting with clients.

Team Leadership Meeting Simulation:

Scenario: Leading a team in the insurance agency to develop new sales strategies.

Task: Conduct a team meeting to discuss sales challenges and brainstorm solutions.

  • Step 1: Identify a key challenge in achieving sales targets.
  • Step 2: Facilitate a productive discussion to brainstorm and decide on innovative sales strategies.
  • Objective: Practice effective leadership and communication in a team setting, similar to Phil’s management style in his agency.

Appendix C: Ten Coursework Modules

This appendix explores how Phil’s remarkable journey embodies the principles from our course modules at Prison Professors. Each is essential for overcoming adversity and achieving success. From defining values to appreciating blessings, these lessons played a significant role in Phil’s path, providing a framework for others to emulate in their pursuit of growth.

Values: We must define success.Phil’s definition of success evolved from overcoming poverty to advocating for justice and excelling in the insurance industry. He understood that success is not just about financial gain but also about making a positive impact and leaving a legacy.
Goals: We must set clear goals that align with our definition of success.Phil set clear, ambitious goals throughout his journey, such as excelling academically despite financial constraints, becoming a prominent figure in the legal field, and later achieving top producer status in insurance sales.
Attitude: We must make a commitment with the right attitude.Phil’s attitude was characterized by resilience and determination. He faced challenges head-on, whether it was financial hardship, legal battles, or entrepreneurial ventures, always maintaining a positive and proactive approach.
Aspiration: We must see ourselves as being something more than the challenges we currently face.Despite facing numerous challenges, Phil always aspired to be more. His journey from poverty to professional acclaim showcases his belief in the possibility of change and growth, regardless of one’s starting point.
Action: We must take incremental action steps.Phil’s success was built on taking consistent, incremental steps. Whether it was diligently studying while on welfare or strategically building his insurance business, he understood the importance of steady progress.
Accountability: We must hold ourselves accountable.Throughout his life, Phil held himself accountable for his actions and decisions. This trait was particularly evident in his legal career, where he challenged systemic injustices and stood up for what he believed was right.
Awareness: We must stay aware of opportunities.Phil remained aware of and open to new opportunities, which allowed him to pivot from law to insurance successfully. His ability to adapt and see potential in different fields was a key factor in his varied successes.
Authenticity: We must be authentic.Phil’s authenticity shone through in every endeavor. Whether in courtrooms or in the insurance business, he stayed true to his values and beliefs, which garnered respect and trust from those around him.
Achievement: We must celebrate small victories.Phil recognized and celebrated his achievements, big and small. From academic successes to landmark cases and business milestones, each victory was a testament to his hard work and persistence.
Appreciation: We must show appreciation for the blessings that come our way.Phil showed appreciation for the opportunities and blessings that came his way. This gratitude is evident in his commitment to mentoring others and giving back, reflecting his recognition of the support and chances he had received on his journey.

By understanding and applying these principles, we can draw inspiration from Phil’s story and incorporate these values into our own paths toward success and fulfillment.

Appendix D: Replicating Phil’s Success

This appendix provides guidance for our students as they seek to draw inspiration from Phil’s journey and apply similar strategies and principles in their own lives. By following these steps, our listeners can work towards rebuilding their lives and achieving success.

Embrace Education and Continuous Learning:

  • Follow Phil’s belief in the power of education. Seek out learning opportunities, whether formal or through self-study.
  • Utilize available resources like libraries, online courses, and mentorship programs.

Develop a Strong Work Ethic:

  • Cultivate the same level of dedication and discipline that Phil demonstrated in balancing law school and full-time work.
  • Understand the value of hard work in overcoming challenges and achieving goals.

Build Resilience and Adaptability:

  • Learn from Phil’s ability to adapt to various life changes and challenges. Develop resilience to cope with setbacks and changes in your circumstances.

Foster Effective Communication Skills:

  • Emulate Phil’s focus on effective communication. Practice clear and empathetic communication; this point is crucial for building relationships and professional networking.

Create and Work Towards Clear Goals:

  • Set specific, achievable goals as Phil did throughout his career. Break these goals into manageable steps and track your progress.

Stay Authentic and True to Your Values:

  • Be genuine in your interactions and stay true to your core values, following Phil’s example of authenticity.

Seek and Embrace Role Models and Mentors:

  • Look for role models who inspire you, as Phil was inspired by figures like Coretta Scott King. Seek mentorship opportunities to gain guidance and support.

Engage in Community and Networking:

  • Build a supportive network as Phil did in his professional life. Engage with community resources, support groups, and professional associations.

Utilize Transferable Skills:

  • Identify and hone transferable skills that can be applied in various career paths, much like Phil’s transition from law to insurance.

Practice Accountability and Personal Responsibility:

  • Hold yourself accountable for your actions and decisions, a key aspect of Phil’s approach to both personal and professional life.

Take Calculated Risks and Innovate:

  • Be open to taking calculated risks in your career and personal life. Embrace innovation and creativity in finding solutions and new opportunities.

Celebrate Achievements and Practice Gratitude:

  • Acknowledge and celebrate your successes, big or small. Practice gratitude for the progress made and the support received.

This guide aims to provide a roadmap for our students seeking to navigate their journey toward success, drawing inspiration from Phil’s resilience, work ethic, and continuous pursuit of growth. Remember, every individual’s path is unique, but the principles of hard work, learning, and perseverance remain universal.

Appendix E: Biographical Sketches

This appendix provides biographical sketches of the famous individuals mentioned in the interview with Phil. Each person played a unique role in their respective fields, ranging from law and civil rights to entertainment and technology. Their stories and achievements offer inspiration and insight into different aspects of success and leadership.

  • F. Lee Bailey (1933-2021) A prominent American lawyer, Bailey was renowned for his role in high-profile cases, including the defense of O.J. Simpson. He was known for his sharp legal mind and persuasive courtroom presence.
  • Tony Bennett (born 1926) An iconic American singer, Bennett is celebrated for his long and successful career in music, particularly in jazz and traditional pop standards. His hits include “I Left My Heart in San Francisco.”
  • Viktor Frankl (1905-1997) An Austrian neurologist, psychiatrist, and Holocaust survivor, Frankl was the founder of logotherapy, a form of existential analysis. He is best known for his influential book “Man’s Search for Meaning.”
  • Bill Gates (born 1955) Co-founder of Microsoft, Gates played a pivotal role in the personal computer revolution. He later became known for his philanthropic work through the Bill & Melinda Gates Foundation.
  • Joe Girard (born 1937) Known as a great car salesman, Girard has been recognized by the Guinness Book of World Records for his extraordinary sales record. He is also an author and motivational speaker.
  • Malcolm Gladwell (born 1963) A British-Canadian journalist, author, and public speaker, Gladwell gained fame for his unique perspective on popular psychology and sociology. His notable works include “The Tipping Point” and “Outliers.”
  • Coretta Scott King (1927-2006) An American author, activist, and civil rights leader, Coretta was the wife of Martin Luther King Jr. She played a significant role in the Civil Rights Movement and advocated for African-American equality.
  • Martin Luther King Jr. (1929-1968) A prominent leader in the American Civil Rights Movement, King is best known for his role in advancing civil rights through nonviolence and civil disobedience, inspired by his Christian beliefs.
  • William Kunstler (1919-1995) An American civil rights attorney known for his controversial clients, Kunstler played a significant role in many of the most famous trials of the 20th century, often focusing on issues of civil rights and social justice.
  • Rob Lowe (born 1964) An American actor, Lowe rose to fame as a teen idol in the 1980s and continued to build a successful career in television and film. He is known for his roles in “The West Wing” and “Parks and Recreation.”
  • Nelson Mandela (1918-2013) A South African anti-apartheid revolutionary and politician, Mandela served as President of South Africa. He is celebrated globally for his role in fighting apartheid and his advocacy for reconciliation.
  • Brad Pitt (born 1963) An American actor and film producer, Pitt has received multiple awards and nominations for his performances. He is known for his roles in films like “Fight Club,” “The Curious Case of Benjamin Button,” and “Once Upon a Time in Hollywood.”
  • Ronald Reagan (1911-2004) The 40th President of the United States, Reagan was a former actor and governor of California. His presidency was marked by a conservative shift in American politics, economic policies known as Reaganomics, and the end of the Cold War.

Appendix F: Related Reading and Resources

This appendix is a curated collection of literature that complements the themes and lessons derived from Phil’s story. It includes books on sales techniques, personal development, and notable works mentioned during the interview. This selection is designed to provide a well-rounded understanding and inspiration for our students, particularly those with an interest in sales, entrepreneurship, and personal growth.

Sales Career-Related Literature
“Influence: The Psychology of Persuasion” by Robert B. Cialdini: This book explores the psychology behind why people say “yes” and how to apply these understandings in various aspects of marketing and sales.   “SPIN Selling” by Neil Rackham: Based on extensive research, this book introduces the SPIN (Situation, Problem, Implication, Need-payoff) technique, revolutionizing the way to conduct big sales.   “The Challenger Sale: Taking Control of the Customer Conversation” by Matthew Dixon and Brent Adamson: This book argues that classic relationship-building is not enough and instead presents an approach based on challenging the customer’s thinking.   “To Sell Is Human: The Surprising Truth About Moving Others” by Daniel H. Pink: Pink offers a fresh look at the art and science of sales, emphasizing the need for every professional to refine their selling skills.   “The Sales Acceleration Formula: Using Data, Technology, and Inbound Selling to go from $0 to $100 Million” by Mark Roberge: This book provides a scalable, predictable approach to growing revenue and building a successful sales team.   “Sell or Be Sold: How to Get Your Way in Business and in Life” by Grant Cardone: This book emphasizes the importance of sales skills in all aspects of life and offers strategies to improve your ability to sell.   “Fanatical Prospecting” by Jeb Blount: This book is a practical guide to the importance of prospecting in sales, offering techniques and routines to improve sales effectiveness.
General Reading
“Man’s Search for Meaning” by Viktor Frankl: This powerful book by psychiatrist and Holocaust survivor Viktor Frankl explores finding meaning in suffering and the human capacity for resilience.   “The 7 Habits of Highly Effective People” by Stephen R. Covey: Covey’s book is a classic for personal and professional development, focusing on principles like proactivity, prioritization, and effective communication.   “How to Win Friends and Influence People” by Dale Carnegie: This timeless book offers principles in handling people, winning others over to your way of thinking, and changing people without causing offense or arousing resentment.   “Mindset: The New Psychology of Success” by Carol S. Dweck: Dweck’s book delves into the power of our mindset in shaping our lives, particularly the difference between a fixed mindset and a growth mindset.   “The Power of Now: A Guide to Spiritual Enlightenment” by Eckhart Tolle: Tolle’s book focuses on the importance of living in the present moment and detaching from material concerns to find inner peace and resilience.
Books Mentioned in the Interview
“The Defense Never Rests” by F. Lee Bailey: Phil recalls reading this book at the age of 13, which helped spark his interest in law and civil rights.   “Outliers” by Malcolm Gladwell: Michael Santos refers to this book while discussing the concept of investing 10,000 hours to become an expert in a field.   “How to Sell Anything to Anybody” by Joe Girard: Phil mentions this book when discussing the story of Joe Girard, recognized as a great car salesman.

Appendix G: Advocacy Organizations

This appendix features a selection of advocacy organizations that can be particularly helpful for students seeking support, resources, and guidance. These organizations offer a range of services, from legal assistance to educational and entrepreneurial support, and can be valuable resources for those on a path to rebuilding their lives.

Prison Entrepreneurship Program (PEP) – Offers entrepreneurship training and post-release support for formerly incarcerated individuals.


The Innocence Project – Works to exonerate the wrongly convicted through DNA testing and reforms the criminal justice system to prevent future injustice.


The Last Mile – Prepares incarcerated individuals for successful reentry through business and technology training.


National Reentry Resource Center (NRRC) – Provides education, training, and policy resources for reentry.


Legal Action Center – Advocates for policy reform and provides legal services to those with histories of addiction, HIV/AIDS, or criminal records.


Root & Rebound – Offers legal advocacy and support for reentry.


Defy Ventures – Focuses on transforming the lives of business leaders and people with criminal histories through entrepreneurial training and mentorship.


Homeboy Industries – Provides training and support to formerly gang-involved and previously incarcerated individuals.


The Fortune Society – Offers a holistic and integrated “one-stop-shopping” model of service provision to formerly incarcerated individuals.


Jobs for Felons Hub – Provides employment and reentry resources for ex-offenders.


Appendix H: Potential Careers

This appendix provides a detailed list of sales-related careers and opportunities in the legal sector that are generally accessible for members of our audience. These careers align with Phil’s journey, demonstrating the potential for success despite past challenges.

  • Insurance Sales Representative: Roles include life insurance agent, property insurance seller, or health insurance representative. These positions require understanding various insurance products and building client trust.
  • Real Estate Agent: Real estate sales agents help clients buy, sell, or rent properties. This field requires licensing but can offer flexibility and high earning potential.
  • Automotive Sales Consultant: Professionals in this role focus on selling new or used cars at dealerships, requiring strong negotiation skills and product knowledge.
  • Retail Sales Associate: In large chain stores or specialty shops, this position involves direct customer interaction, product promotion, and sales transactions.
  • Financial Products Sales Advisor: Similar to Phil’s role in annuity sales, this position involves advising clients on financial products like mutual funds, annuities, or retirement plans.
  • Entrepreneur/Self-Employed Salesperson: This could range from launching an online retail store to starting a direct B2B sales consultancy, reflecting Phil’s entrepreneurial drive.
  • Legal Assistant or Paralegal: Supporting lawyers with research, document preparation, and case management, these roles are integral to legal offices and can be accessible to those with a felony.
  • Legal or Sales Consultant: Leveraging expertise in specific areas, consultants offer advice and strategies to businesses or legal entities.
  • Independent Sales Contractor: This role involves representing a company’s products or services as an independent agent, focusing on sales targets and client relationships.
  • Telemarketer/Inside Sales Representative: Conducting sales or marketing over the phone, these positions prioritize persuasive communication skills and product knowledge.
  • Customer Service Representative in Legal Services: Offering support and information to clients in legal settings, these roles require good communication and an understanding of legal procedures.
  • Sales and Marketing Coordinator: In this role, individuals manage sales activities, coordinate marketing campaigns, and develop sales strategies.
  • Business Development Executive: Focusing on growing business opportunities, this role involves strategic planning, client outreach, and market analysis.
  • Legal Advocate or Case Worker: In non-profits or advocacy groups, these roles involve supporting individuals with legal challenges, requiring knowledge of the legal system and strong communication skills.

Each of these careers offers a pathway to professional growth and reintegration. They underscore the importance of skill development, adaptability, and determination, as exemplified in Phil’s story. With the right approach and mindset, our students can achieve success in these fields.

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