Prison Professors

1. Abstract

Today's MasterClass on Prison Professors shares Kyle’s inspiring story. Participants learn how he turned a challenging childhood and early setbacks into a pathway to financial and professional success. By learning from Kyle’s experiences, students will understand the power of crafting a success plan, identifying opportunities, and learning the transferable skills essential for scaling personal and business growth. This lesson integrates the Straight-A Guide principles, offering actionable strategies for those in prison—and anyone—who want a MasterClass on how to prepare for success.

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2. Detailed Narrative

Kyle’s transformation offers invaluable lessons for overcoming challenges and building a successful future. He didn't grow up in privilege. His life began in a strict household in Spartanburg, South Carolina. His father worked as a police officer.

Despite growing up in a household of a law enforcement professional, Kyle faced a turbulent upbringing, including instability and brushes with the law. As a strict disciplinarian, his father gave Kyle the boot from the household, and he had to learn how to navigate the streets. In that environment, he started going down the road of a “troubled life,” as he candidly describes it during our conversation.

Early challenges did not block him from success, however. His story may have begun with misdirection, yet with perseverance, he build a record of that gives us an extraordinary example of resilience, strategy, and transformation—principles that can guide anyone toward success.

When I listened to Kyle tell me his story, I thought about the principles from Angela Duckworth’s book Grit. Lessons from that book offer a powerful lens through which to view Kyle's journey. Duckworth defines grit as the combination of passion and perseverance in pursuit of long-term goals, and Kyle’s life embodies these principles perfectly. He faced tough odds that could have held him back, but through determination and an unwavering commitment to learning, he transformed his path. Just as Grit emphasizes the importance of sustained effort over time, Kyle’s persistence in overcoming obstacles and pursuing self-improvement demonstrates how grit can lead to extraordinary achievements. His story is a testament to the idea that perseverance and passion for growth can unlock incredible potential, even in the face of challenges.

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Resilience in Adversity

Kyle’s early years were marked by hardship, exemplified by his experience with homelessness and a series of decisions that led him down an illegal path. He worked to earn his GED and, when he made the commitment to get his life together, he joined the U.S. Army. It wasn't an easy transition. Even in the military, Kyle continued making decisions that put him the crosshairs of trouble.

In Earning Freedom: Conquering a 45-Year Prison Term, I wrote about it never been too early, and never being too late to start working toward a better life. When authorities first arrested me, I wasn't ready to begin accepting responsibility and working to atone. It wasn't until after a jury convicted me that I realized had to change. We can work toward change any time we're ready.

Eventually, after some set backs with disciplinary problems, Kyle began to recalibrate his mindset. His military experience, while tumultuous, planted the seed of discipline and the realization that he needed to pivot toward a sustainable, law-abiding career path. His challenges echo the principle of resilience, a crucial quality for anyone aspiring to overcome steep odds.

“As I started growing up, all I had done was mess things up. But one day, I decided to drive to Florida instead of returning to the streets of South Carolina. That single decision changed my trajectory,” Kyle told us during his candid interview.

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Identifying Opportunities

Landing in Florida at a time of economic uncertainty, Kyle focused on taking proactive steps. He accepted a commission-based sales job requiring cold-calling and relentless effort. Through perseverance, he learned to handle rejection, refine his sales techniques, and develop the art of persuasion—skills that later became the building blocks of his entrepreneurial success.

“Getting comfortable with hearing ‘no’ was the most valuable skill I gained,” Kyle explains.

Ever person in prison is comfortable with hearing the word "No." If we want to overcome the challenges in our life, we've got to learn from masters like Kyle. He didn't allow objections to become road blocks. Instead, he was more like that great writer, Jocko, who wrote about the importance of personal accountability and responsibility.

Jocko Willink’s book, Extreme Ownership: How U.S. Navy SEALs Lead and Win, offers profound lessons on leadership, responsibility, and resilience that resonate in both personal and professional spheres. The core principle of “extreme ownership” emphasizes taking complete responsibility for everything within one’s domain of influence, leaving no room for excuses or blame. Jocko’s stories from the battlefield illustrate how discipline and accountability are critical to building trust and achieving success. One powerful takeaway is the idea that true leaders empower their teams by owning failures, learning from mistakes, and inspiring others through action. His message serves as a motivational reminder that success stems from personal growth, adaptability, and an unwavering commitment to overcoming adversity.

This insight reinforces the Straight-A Guide’s principles, including attitude. If we make a 100 percent commitment to success, we can start to focus on our personal growth and building a positive mindset.

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Building Transferable Skills

Kyle’s breakthrough came when he embraced self-reliance.

Kyle’s career development began with a humble yet pivotal role in marketing products and services. This position exposed him to a challenging environment where rejection was a daily occurrence. Instead of being discouraged, Kyle chose to view these rejections as opportunities to build resilience and sharpen his communication skills. Each "no" became a stepping stone, teaching him to approach conversations with empathy, adaptability, and persistence.

Over time, Kyle transformed rejection into a powerful motivator, propelling his personal and professional growth. He learned to focus on what he could control—his attitude, effort, and preparation. This mindset not only enhanced his ability to thrive in high-pressure situations but also prepared him for leadership roles, where these qualities are essential. Kyle’s perseverance through setbacks became the hallmark of his career, serving as a testament to the idea that tenacity and self-improvement can turn challenges into triumphs.

The skills that Kyle developed—resilience, adaptability, and a focus on self-control—can empower anyone to overcome adversity and achieve personal growth. By channeling energy into what one can control, such as mindset and preparation, individuals can transform setbacks into stepping stones. For those in prisons, these lessons hold profound significance. The ability to reshape one’s narrative starts with cultivating inner strength and taking ownership of one’s actions and future. Education, self-discipline, and a growth-oriented mindset can become tools to unlock potential. Kyle’s story highlights that, no matter the environment, building these skills lays the foundation for hope and transformation.

We may not be able to build income streams while in prison, as Kyle did, but we can always work to develop our communication skills. If we learn to write better, speak more persuasively, we can develop confidence that will translate into an income stream upon release.

Kyle developed so much skill that he was able to pivot from working for others to building his own digital marketing agency.

Teaching himself digital marketing was no easy feat for Kyle. Without formal education or access to traditional resources, he had to rely on his own determination and resourcefulness. He began by consuming whatever information he could find—articles, free online courses, and books about marketing principles, SEO, content creation, and analytics. By breaking complex topics into manageable pieces and practicing what he learned, Kyle transformed theoretical knowledge into actionable skills. He proved that digital marketing isn’t reserved for those with degrees or extensive resources; it’s a skill that anyone can develop with curiosity, discipline, and consistency. Kyle’s story demonstrates that the willingness to learn and adapt can empower anyone to build a successful future.

As a true master, Kyle forged his success out of the fire of adversity. When his boss refused to give him the crutch of a base salary, Kyle realized that it was time to sink or swim. He could either develop skills that would help him build leads for more sales, despite a setback, or he could complain.

When I heard his story, I realized how much I could learn from him. What can you learn from his story?

From generating leads using Facebook ads to mastering customer relationship management (CRM) systems, Kyle built a foundational toolkit that fueled his path to scaling multiple businesses.

“Instead of fighting for each sale, I designed systems that brought leads directly to me. Suddenly, I wasn’t chasing customers—they were coming to me.”

For individuals in prison, this lesson demonstrates the importance of cultivating transferable skills—whether technical (like marketing or analytics) or interpersonal (like communication or leadership)—that will serve them well upon release.

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Scaling Success

Kyle’s method for scaling his ventures ties closely to the principle of accountability, which we cover in the sixth module of our Straight-A Guide. By documenting processes, delegating responsibilities, and building CRM platforms, he laid the groundwork for growth. His emphasis on clarity in action illustrates that anyone can build an impactful career with the right systems.

One pivotal takeaway is Kyle's perspective on pivoting failures into success. When faced with challenges, such as losing clients or struggling financially, Kyle adapted by shifting from a flat-fee service model to a performance-based revenue share, significantly expanding his income. This approach highlights the Straight-A Guide’s emphasis on authenticity—leveraging personal strengths to build trust and create value.

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Living in Gratitude

Throughout his rise to success, Kyle remained committed to giving back. He now mentors entrepreneurs and volunteers with organizations like Prison Professors to share his insights with justice-impacted individuals.

“It’s not about where you start—it’s about where you’re willing to go. I want to give others the same opportunity to rewrite their stories,” Kyle states. This mindset ties to the principle of appreciation, underscoring the importance of gratitude and mentorship.

Kyle’s story affirms that preparation, perseverance, and systems are the keys to turning adversity into opportunity. By applying these lessons, anyone can begin crafting a brighter future, regardless of their starting point.

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3. Vocabulary Development

Resilience – The capacity to recover quickly from difficulties.
Persuasion – The ability to convince others of a particular idea or plan.
Transferable – Skills or qualities that can be applied in different contexts or roles.
Sustainable – Capable of maintaining long-term stability and success.
Pivoting – Adapting to significant changes by redefining strategy.
Delegating – Assigning responsibility or authority to others.
Scalability – The ability to grow or expand while maintaining efficiency.
Accountability – Taking ownership of actions and responsibilities.
Authenticity – Acting with honesty and true to intrinsic values.
Mentorship – Guiding and supporting others through shared knowledge and experience.

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4. Self-Directed Reflection Questions

How can challenges in your past inspire a better future?
What small, daily actions can you take toward achieving your long-term goals?
How can you develop resilience in the face of rejection or setbacks?
What transferable skills are you working to build, and how will they prepare you for life after release?
How can you use gratitude to stay motivated while working toward success?
What can you do today to begin crafting systems that will support future growth?
How can you ensure accountability in your personal and professional decisions?
What steps can you take to document your progress and showcase your growth?
How can you develop a professional network to aid your reintegration into society?
What role does authenticity play in building trust, and how can you apply it to your personal development?

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5. Recommended Books

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Think and Grow Rich by Napoleon Hill

This classic focuses on the enduring principles of success, including mindset and goal-setting, many of the strategies Kyle used during his transformation.

"“Every adversity, every failure, every heartache carries with it the seed of an equal or greater benefit.”

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Atomic Habits by James Clear

An excellent guide to forming productive habits, this book outlines simple changes that lead to remarkable results—parallel to Kyle’s disciplined efforts in sales and marketing.

"“You do not rise to the level of your goals. You fall to the level of your systems.”

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The Lean Startup by Eric Ries

A must-read for aspiring entrepreneurs, this book covers how to adapt through learning and efficient experimentation, mirroring Kyle’s approach to building scalable systems.

"“The only way to win is to learn faster than anyone else.”

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6. Straight-A Guide Integration

Define Success – Kyle defined his ideal career and pursued it relentlessly.
Set Goals – He set incremental goals, from refining sales skills to scaling his businesses.
Cultivate Attitude – Kyle demonstrated resilience and positivity through challenges.
Aspire – Kyle envisioned a future bigger than his circumstances.
Take Action – From cold-calling to creating funnels, Kyle prioritized execution.
Accountability – Metrics and delegation were key to his scaling strategies.
Awareness – Identifying critical opportunities (e.g., Facebook ads) propelled Kyle forward.
Authenticity – His honesty in communication made him a trusted resource.
Achievement – Kyle celebrated milestones, reinforcing continued growth.
Appreciation – Giving back became a central part of his success story.

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7. Sample Response:

If I were still in prison, and I had the privilege of listening to Kyle's MasterClass, I would have worked through each of the questions in the lesson. And I would have responded in ways that, I hoped, would bring persuade others to view me differently, seeing me as a potential candidate for support. Remember, no one should work harder than us toward the success we want to build. Below is a sample of how I would have responded if I were still in prison, and I would have published the response on my profile, so others could see.

I'm sitting here in prison, learning from a MasterClass with Kyle, a guy who overcame challenges to become a successful entrepreneur. I learned a lot from listening to his story. Although I may not become a great entrepreneur while I serve my sentence, but I can prepare.

I’ve had a lot of time to think about my past—about the mistakes, the pain, and the choices that got me here. Hearing Kyle’s MasterClass, it hit me: challenges don’t have to define you, but they can shape you.

My struggles taught me resilience, patience, and the ability to see things from a new perspective. If I can take those lessons and use them to guide my decisions moving forward, then my past isn’t a dead end—it’s the foundation for building something better. The hard moments have given me the determination to create a future that’s meaningful, for myself and for others.

Kyle’s story showed me that it’s possible to turn trials into triumphs, as long as you have the right mindset and the willingness to take action.

Starting today, I’m committed to learning from my past and using it to fuel my journey towards success. So, no more waiting for opportunities—I’m ready to create them. It’s time for a pivot—to redefine what success means for me and start making moves towards a brighter future.

Thank you, Kyle, for showing me that anything is possible if I believe in myself and put in the work. I can’t wait to see where this journey takes me. Keep pushing forward!

Takeaway: By writing these kinds of responses, we inspire others to see us differently from the way that prosecutors want to present us. We're all capable of new opportunities. But we must be like Kyle. If we're humble, and we're willing to work hard, more opportunities open.

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8. Challenge

Develop Your Profile on Prison Professors Talent

Showcase your growth via detailed responses to reflective prompts. Demonstrate your commitment to daily self-directed learning, skill development, and readiness for reintegration. Highlight how your work reflects extraordinary dedication to creating value for society.

Through Kyle’s example, it’s clear that success isn’t about avoiding obstacles—it’s about mastering them. Start building your pathway to excellence today.

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