MasterClass with Greg Plumber

Abstract

This lesson explores how individuals can build resilience, develop multiple revenue streams, and use strategic thinking to thrive despite adversity. Through Greg's story, students will learn actionable strategies for entrepreneurship, the importance of understanding how to take calculated risks, and the role of continuous learning in adapting to changes.

Greg’s Journey from Builder to Entrepreneurial Success

Greg’s story teaches us that resilience, adaptability, and education are the keys to thriving in any circumstances. Born to a military family, Greg’s transitory childhood taught him the value of adaptability early. Moving to Texas in 1985, Greg discovered his passion for design and construction by reconfiguring floor plans on graph paper in his teenage years. Although he suffered from attention deficit disorder (ADD), he excelled in mathematics, which later became his strong suit. While in high school, he said that he earned better-than-average grades, though not exceptional. Instead of pursuing a career in academia, he focused on subjects where he did well.

Greg's story is a testament to the principles outlined in Focus on Your Strengths, a book that emphasizes the power of honing one's natural talents rather than fixating on weaknesses. Instead of allowing his attention deficit disorder (ADD) to define him, Greg channeled his energy into areas where he thrived, such as mathematics and creative design. This approach mirrors the book's core message — to unlock potential by building on innate abilities. By focusing on his strengths, Greg cultivated a unique skill set that later became the foundation of his success. His ability to excel in mathematics and his passion for reconfiguring spaces reflect his determination to align his pursuits with his inherent talents, paving the way for achievements rooted in his strengths.

In listening to Greg's story, students may see an example of what it means to prepare daily. Every day presents an opportunity to plant the seeds of your future success. Even in the most challenging circumstances, the choices you make now—how you use your time, what skills you develop, and how you shape your mindset—are building blocks for what lies ahead.

In our courses, we encourage people to think of the time in prison as an opportunity to set a foundation. Every effort you invest in learning, growing, or understanding yourself is a step toward a better tomorrow. Preparation is powerful, and when you dedicate yourself to meaningful work now, you set the stage for a future that aligns with your goals and aspirations. Remember, the work you do today is never wasted; it becomes the gift you give your future self.

I spoke about this concept with Greg, and he related it to his own career, which didn't follow a linear path. While initially pursuing nursing, he realized that his true strength was in finance and construction. He graduated with a degree in accounting and a minor in finance, beginning his professional life in state and local tax accounting. While in that role, he polished his ability to break down complex regulations, preparing him for the next major chapter of his entrepreneurial endeavors.

From Stability to Ambition

Greg’s entrepreneurial spirit first took shape when he transitioned from accounting to the construction business at the age of 27. During this period, he worked as an apprentice under his soon-to-be father-in-law to learn the intricacies of construction management. "I learned how to build a house, legs up," Greg noted, referring to his hands-on approach to mastering every detail of home-building—from laying foundations to hanging doors.

Through dedication and commitment, he grew the business from scratch, but made great progress each year. In its first year, the business generated sales of about $1.7 million. He kept growing from there, and by the third year, his business brought in approximately $9 million in annual revenue.

He built a second, complimentary business that focused on residential service, which generated $800,000 during its second year of operations, demonstrating Greg’s ability to seize opportunities that would leverage his expertise and connections to generate additional revenue streams. "The margins were higher in the second business because we dealt directly with end consumers," Greg explained, highlighting the strategic decision to expand into areas offering better profitability.

Greg’s remarkable, self-made growth story was not only a result of his strategic business decisions but also his ability to effectively use leverage. A key factor in his success was his focus on building and leveraging relationships. Greg understood the power of networking and actively sought out connections that could open new doors for his business ventures. This approach allowed him to forge partnerships, identify untapped opportunities, and collaborate with individuals who shared his vision. By positioning himself as a reliable and innovative entrepreneur, Greg gained the trust of collaborators and customers alike, which became a pivotal element in scaling his operations.

As Greg’s ventures flourished and his reputation for success grew, lending institutions recognized his potential and extended financial resources in the form of loans. Greg strategically utilized these loans by collateralizing his assets, allowing him to inject significant capital into his businesses. This financial leverage enabled him to expand more aggressively, invest in infrastructure, and capitalize on high-margin opportunities. By taking well-calculated risks, Greg ensured that he could maximize returns while continuing to grow his businesses at an impressive pace.

However, leveraging comes with its own set of pros and cons. On the positive side, leveraging relationships and financial resources provided Greg with the ability to accelerate his business’s growth trajectory far beyond what organic progression would have allowed. It empowered him to seize opportunities and outpace competitors. On the other hand, the reliance on loans and asset collateralization introduced an element of risk.

No one could control the market. And if market conditions shifted unfavorably, his businesses would not perform up to the expectations he had at the start. In Greg’s case, the financial commitments created significant liabilities, eventually causing stress.

Managing leverage thus required not only optimism but a disciplined approach to ensure investments remained sustainable. Greg's honesty in sharing his story serves as a powerful example of how thoughtful leveraging, both relational and financial, can propel success, while underscoring the importance of taking measured risks.

He told us about the challenges he faced during the 2008-2009 housing market crash.

The 2008 housing market crash had a profound and far-reaching impact, reshaping the real estate market and the global economy. The crash was driven by an unsustainable rise in housing prices, fueled by risky lending practices and speculative investments. When the bubble burst, housing prices plummeted dramatically, resulting in widespread foreclosures and a collapse in property values. Families lost their homes, and financial institutions faced staggering losses.

The ripple effects extended beyond housing, as the crisis contributed to a global recession, leaving a lasting imprint on economic policies and regulations. For many, the crash highlighted the dangers of unchecked speculation and the importance of financial prudence in lending and borrowing practices.

Since had used leverage to grow his business, he faced considerable turbulence. When lenders offered loans during the good times, they secured the loans with collateral. The market turned, meaning fewer people were going into the market to purchase houses. With fewer buyers, prices began to drop. They dropped to a level that was so low that if Greg were to sell the house, the revenues would not cover the amount he had borrowed.

It led to financial stress, causing him to lose his business's assets during the market turbulence.

But Greg did not lose his mindset. Instead, he pivoted, relying upon all the skills that he'd been building upon since his adolescent years. Financial setbacks could be a part of life, but for those who prepare, opportunities open. Greg leaned on his expertise in carpentry to build a new business specializing in installing trim services, which ultimately allowed him to recalibrate and earn a good living from a business that generated about $20,000 in monthly revenue.

During times, Greg understood that he had to stabilize while keeping his eyes open for new opportunities.

Lessons of Resilience and Adaptability

A key lesson embedded in Greg’s story is that adversity often opens unforeseen opportunities. He could leverage earlier skills he developed, but also leverage relationships. One of those relationships opened an opportunity for a new partnership in a field that was totally unrelated to his earlier work in construction or accounting. He began working in the medical field.

Greg didn't plan on going into the business of medical sales, but when his path intersected with a someone to whom he'd previously sold a home, he learned about a new business opportunity in healthcare. Greg didn't hesitate. He went after it with the same commitment that had led to so much success through his other ventures. Within months, he mastered medical sales and led a team that generated millions of dollars in annual revenue.

Greg’s diversified skill set and self-reliance became the foundation for his ability to bounce back. He emphasizes the importance of proactive learning and accountability as tools for leveraging opportunities. “It’s not about what happens to you, but what you do next,” Greg advises.

Mindset Shift and Reflection

Greg’s story is a testament to the power of strategic thinking. By focusing on realistic goals and taking incremental steps, he built expertise across multiple industries. His approach to entrepreneurship also showcases the value of "always being prepared for change." This readiness is not only about technical skills but also about maintaining the right mindset. When asked what made him successful, Greg answers, "A relentless focus on preparation and adaptability."

Greg’s story is not just about his personal success—it’s a blueprint for anyone facing struggles and uncertainties. For students navigating challenges with the justice system, his example serves as a powerful reminder that resilience and preparation can transform even the toughest circumstances. Instead of giving up, these moments of hardship can be seen as opportunities to recalibrate, rebuild, and set yourself on a pathway toward a brighter future.

Like Greg, success begins with preparation. By focusing on foundational skills such as reading, writing, math, and critical thinking, you’re equipping yourself with the tools to unlock new possibilities. These skills act as stepping stones, opening doors to education, better jobs, and new perspectives. The path isn’t always easy, but every small step forward builds confidence and momentum. Remember, it’s not about where you start—it’s about the consistent effort you put into growth.

Vocabulary Development

1. Intricacies – Complex details or specificities.
2. Revenue – Total income generated by a business before costs.
3. Strategic – Relating to careful, planned action toward an objective.
4. Intricate – Highly detailed and complex.
5. Foundational – Relating to the basis or groundwork of a system or process.
6. Tailored – Customized or adapted to specific needs or wants.
7. Self-reliance – Dependence on one’s own abilities and decisions.
8. Leveraged – Used borrowed money to finance a business venture.
9. Incremental – Describing small, gradual improvements.
10. Adaptability – The ability to adjust to new conditions.

Self-Directed Reflection Questions

1. What skills have you developed that can be repurposed for entirely different career paths?
2. Think about a setback you’ve faced. How did you adapt, and what did you learn from the experience?
3. How can building multiple income streams safeguard your financial stability during challenging times?
4. What steps can you take today to prepare for a different career industry in five years?
5. How might focusing on foundational skills like math or communication help you later in a specific business?
6. What opportunities could arise from investments in self-learning or personal development?
7. Evaluate a recent decision. Did you consider the long-term risks and rewards?
8. What are some ways to stay accountable to your goals while managing day-to-day responsibilities?
9. How does being proactive make you more resilient to professional challenges?
10. How can you leverage your personal values to thrive while creating meaningful contributions to society?

Supplemental Reading

In all our courses, we urge students to broaden their education and understanding with supplemental reading. Based on the lessons that I learned from Greg, and my conversations with him, I recommend the following books that relate to his story.

The Obstacle Is the Way: The Timeless Art of Turning Trials into Triumph

Author: Ryan Holiday

Book Summary:

The Obstacle Is the Way draws from the ancient philosophy of Stoicism, particularly the teachings of Marcus Aurelius, to teach a powerful principle: what stands in the way becomes the way. Holiday illustrates how adversity can be transformed into strength by using real-life stories of historical figures—like John D. Rockefeller, Amelia Earhart, and Ulysses S. Grant—who faced tremendous challenges and turned them into opportunities for growth and victory.

The book is divided into three parts:

1. Perception – how we see and frame problems
2. Action – how we respond with discipline and creativity
3. Will – how we endure and overcome with resilience

With practical and motivational lessons, Holiday shows that the key to progress isn’t avoiding hardship, but learning how to face it with purpose and power.

Connection to Greg’s Story:

Greg’s journey is a real-world illustration of the Stoic mindset Holiday promotes.

• When the 2008 housing crash wiped out Greg’s construction empire, he didn’t fold—he reframed the crisis as a chance to pivot.
• His decision to lean on earlier skills in carpentry and later enter an entirely new field (medical sales) is the essence of resilience and resourcefulness.
• Greg didn’t see setbacks as the end—he saw them as obstacles that pointed him toward new paths.
• His mindset—“always be prepared for change”—mirrors the Stoic idea that you can’t control events, only your response.

Just like Greg, readers of The Obstacle Is the Way will learn to embrace difficulty, prepare daily, and unlock strength through adversity.

Start with Why: How Great Leaders Inspire Everyone to Take Action

Author: Simon Sinek

Book Summary:

Start with Why is a groundbreaking exploration of what makes some individuals and organizations more successful, influential, and resilient than others. Simon Sinek argues that people don’t buy what you do—they buy why you do it. He introduces the concept of the Golden Circle:

1. Why – The purpose, cause, or belief that inspires you
2. How – The process you follow
3. What – The result of what you do

Through examples like Apple, Martin Luther King Jr., and the Wright brothers, Sinek shows how clarity of purpose (“why”) becomes the foundation for powerful leadership, innovation, and trust. The book encourages readers to look inward, identify their motivations, and build meaningful careers and lives around their purpose.

Connection to Greg’s Story:

Greg didn’t build a story of entrepreneurial success by taking shortcuts. He always had a clear sense of purpose and a drive to solve problems, serve people, and create value.

• His early interest in reconfiguring spaces and building homes was rooted in a “why” connected to creativity and impact.
• When setbacks struck—especially during the 2008 crash—Greg didn’t abandon his path; he reconnected with his purpose, adapted, and moved forward with intention.
• Even his pivot to the medical sales industry reflected a purpose-driven mindset: he saw an opportunity to help people, lead a team, and make a difference.

Students reading Start with Why can use Sinek’s framework to better understand their own motivations—especially in times of challenge. Like Greg, they’ll see that clarity of purpose fuels resilience and lasting success.

Man’s Search for Meaning

Author: Viktor E. Frankl

Book Summary:

Man’s Search for Meaning is a profound memoir by psychiatrist Viktor Frankl, chronicling his experiences as a prisoner in Nazi concentration camps during World War II. But more than a historical account, the book presents Frankl’s philosophy of “logotherapy”—the belief that finding meaning in life is the primary driving force of human beings, even in the face of unimaginable suffering.

Frankl argues that while we cannot always control our circumstances, we can always choose our response—and in that response lies our freedom and personal power. He famously wrote:

“Those who have a ‘why’ to live, can bear almost any ‘how.’”

The book is often broken into two parts:

1. A personal narrative of survival in the camps.
2. A psychological analysis of meaning and resilience.

It’s an enduring classic read by millions, especially by people enduring hardship or rebuilding after trauma.

Connection to Greg’s Story:

Greg’s life is a modern example of Frankl’s core principle: that meaning and mindset can carry us through the most trying times.

• When Greg lost everything during the housing crash, he didn’t give up. He chose to rebuild his life with purpose—first through trim carpentry, then by helping others in medical sales.
• Even though the path wasn’t linear, Greg found meaning in preparation, in service, and in perseverance.
• His journey teaches that resilience comes not from avoiding pain, but from choosing to grow through it—just as Frankl wrote.

For students facing incarceration or adversity, Man’s Search for Meaning offers not only hope, but a framework to find purpose in the present and strength for the future.

Recap of the Straight-A Guide

1. Define Success – Setting clear, measurable objectives helped Greg establish entrepreneurial and financial goals. 
2. Set Goals – Greg’s pivot between fields was always guided by specific, well-structured objectives. 
3. Attitude – Greg's resilience reflects his unwavering positive attitude, focusing on opportunities rather than failures. 
4. Aspiration – Greg aspired to create enduring businesses that generate value across industries. 
5. Action – Greg’s incremental approach to problem-solving serves as a practical model for sustained action. 
6. Accountability – By tracking all aspects of business operations, Greg maintained clarity and accountability despite challenges. 
7. Awareness – Greg’s proactive awareness allowed him to seize new opportunities where others faltered. 
8. Authenticity – Greg’s transparency and integrity have been key to building trust with partners and clients. 
9. Achievement – Celebrating small milestones kept Greg motivated amidst adversity. 
10. Appreciation – Greg’s gratitude for opportunities fuels his continued efforts to inspire and mentor others.

Socratic Reflection Questions:

1. When you reflect on your current situation, what strengths do you have that you may be overlooking or underutilizing—just as Greg once overlooked his gift for finance and construction?
   
   
2. Greg rebuilt his life after financial devastation. What past challenge in your life revealed hidden potential or forced you to grow in a way you didn’t expect at the time?
   
   
3. If your career path or life plan was suddenly disrupted, how would you respond? What skills or mindsets would you rely on to pivot in a new direction?
   
   
4. Greg succeeded by preparing daily, even when success wasn’t guaranteed. What small, consistent action could you start today that would move you closer to your long-term goals?
   
   
5. Greg used leverage—relationships, skills, and loans—to build his businesses. What relationships or resources could you cultivate right now that might help you in the future?
   
   
6. What does accountability mean to you, and how do you hold yourself accountable when no one is watching?
   
   
7. Greg said, “It’s not about what happens to you, but what you do next.” When something goes wrong in your life, what story do you tell yourself—and how does that affect your next decision?
   
   
8. Greg didn’t let ADD define his identity. What label or limitation have you internalized that might be holding you back—and how could you reframe it into a strength?
   
   
9. Think of a time when you achieved something by focusing on preparation rather than the outcome. How did that shift in focus change your approach or result?
   
   
10. If someone wrote your story 10 years from now, what would you want them to say about how you handled adversity, made decisions, and stayed true to your purpose?

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Sample Response

To assist members of our community, I’ll write a sample response. Remember, there are no right answers or wrong answers. We offer these MasterClass lessons as a prompt to assist people who want to develop pathways to success. Build a record that will show your commitment to self-directed learning. This sample shows how I would have responded to question 1, if I had an opportunity to learn from Greg’s lesson while I was in prison:

I’m writing this from a cement box—no window, no clock, no sound beyond the occasional clank of steel doors down the tier. I don’t even know what time it is. But I just finished reading Greg’s lesson, and I’m struck by how he rediscovered a strength he’d overlooked. Construction and finance weren’t just jobs—they were parts of him that he almost missed.

That got me thinking: What strengths do I have right now? Sitting here in solitary, stripped of everything I once thought defined me—freedom, status, the illusion of control—I’m forced to look inward. I can’t fall back on hustle or fast talk anymore. That part of me—what landed me here—isn’t a strength. It’s a warning.

But if I look deeper, I remember: I’ve always been curious. I’ve always been a learner. I may not have used that gift the right way before, but it’s still mine. I’ve also got discipline. When I really care about something, I go all in. I used to put that energy into the wrong things. Now, I’ve got to redirect it.

Maybe my strength is my ability to change—to learn, to adapt, to build something new from this place where it seems like everything is over.

Greg’s story showed me that success doesn’t come from having all the answers—it comes from asking the right questions and being willing to start over. I’ve still got my mind. I’ve still got time. And if I choose to use both with intention, maybe one day I’ll turn this solitary cell into a classroom—maybe even a launching pad.

Challenge

Develop your personal profile on Prison Professors Talent by outlining how you’ve demonstrated resilience, self-directed learning, and accountability. Use these lessons to show stakeholders your progress in cultivating skills and preparing for a successful post-incarceration transition.

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