Prison Professors

Abstract

This MasterClass features a seasoned investor who shares valuable insights into real estate, private equity, debt placement, and asset management. Andrew generously volunteered his time to guide our community, offering expertise on entrepreneurial strategies, the power of self-learning, and the mindset needed to break into and thrive in the real estate industry. The session emphasizes the importance of making consistent progress, practicing critical thinking, and adopting a value-driven approach to achieve sustainable, long-term success.

Detailed Narrative

Andrew grew up in Rye, New York, a suburban community where commuting into Manhattan for work was the norm. Academics were never his strong suit, and he lacked a deep passion for school. Like many teenagers with whom he grew up, more exciting activities distracted in through high school. He didn't give much attention to academics, and as a result, he earned average grades and he described himself as a mediocre student, with lackluster performance. School didn't interest him.

Despite his lack of interest, Andrew's parents understood the value of academic credentials. They were both professionals and highly successful, and they encouraged him, or pressured him to move forward in pursuit of higher education. They believed that if he earned a university degree, more opportunities would open for his future.

As a young man, Andrew saw himself as an entrepreneur. He struggled to see the value in the traditional academic route. To him, at that age, it would make more sense to launch a startup than to enroll in courses that would require him to study more English, more history, more math. Yet since he didn't have a clear plan on what business he would launch, and since he didn't want to disappoint his parents, he took the next sstep after graduating high school. Once he enrolled in college, he enrolled in courses that would lead to a business degree, with a focus on finance. Surprisingly, once he got started in those courses, he could see how the studies would align with his entrepreneurial aspirations.

In college, Andrew found himself surrounded by like-minded peers, creating a dynamic and engaging learning environment. Immersed in this atmosphere, he fully embraced the experience, discovering that studying subjects he was passionate about could be both enjoyable and deeply rewarding. This newfound curiosity prompted him to venture beyond the classroom. He looked for more books that would help him understand how to value stocks, financial investments, real estate, and business strategies. With a renewed sense of purpose, Andrew approached his studies with focus and determination, ultimately achieving grades that far surpassed his high school performance.

Andrew's story serves as a powerful example of how identifying your interests can transform your approach to learning and personal growth. When you find a subject that genuinely captivates your curiosity, studying no longer feels like a chore—it becomes an exciting pursuit of knowledge. This passion fuels dedication and perseverance, opening doors to insights and skills that might otherwise remain out of reach. Self-directed study, as Andrew discovered, is an invaluable tool in this process. By taking the initiative to seek out resources, ask questions, and explore beyond the confines of formal education, a person begins to build expertise that adds value in the marketplace. With more expertise, more opportunities open.

Mastery is not achieved overnight—it is a commitment to continuous improvement and a willingness to face challenges head-on. It is in this process of deliberate learning that you cultivate the skills, knowledge, and confidence that can propel you toward your goals. Like Andrew, when you take ownership of your education and focus on areas that resonate with your passions, you unlock your full potential, paving the way for a meaningful and fulfilling future. This message completely aligns with the lessons we covered in our introductory courses, which shows that I didn't come up with them on my own—I learned them by listening to masters like Andrew.

After earning his bachelor's degree in business, Andrew wanted to go further. He prepared for the examinations that would advance him as a candidate for graduate school. Once accepted, he worked hard to earn the credentials for a master's degree in business administration, validating his understanding of finance and investment strategies.

Although Andrew was committed to earning formal educational credentials, he acknowledged that learning extends far beyond the traditional college path. Reflecting on his journey, he shared that his informal education began well before he entered the business world. Over the years, he held various roles in hospitality, worked as a cab driver, and completed internships during college. These experiences provided him with invaluable lessons in interpersonal skills and the development of key soft skills like communication and problem-solving. As Andrew wisely noted, “Life is a people business. You’re always learning how to interact with others in ways that position you for new opportunities.”

While formal education often serves as a traditional pathway to success, history is rich with examples of individuals who forged groundbreaking careers without completing a college degree. Some of the wealthiest and most influential figures in modern history—Bill Gates, Michael Dell, and Mark Zuckerberg—demonstrate that passion, vision, and relentless determination often outweigh conventional requirements. Bill Gates, the co-founder of Microsoft, famously left Harvard to pursue his revolutionary ideas in software development, ultimately building one of the most powerful technology companies in the world. Similarly, Michael Dell started his computer business from his college dorm room before dropping out to scale his vision into a global empire. Mark Zuckerberg followed a comparable path, leaving Harvard to focus on building Facebook, now a central pillar of communication and social interaction worldwide.

Barbara Corcoran's rise to success in the competitive world of real estate exemplifies the power of determination and resourcefulness. With no college degree and little experience, Barbara started her career with a $1,000 loan, which she used to establish her own business. From humble beginnings, she steadily built The Corcoran Group, one of the most prominent real estate companies in New York City. Barbara's success can be attributed to her unwavering perseverance, innovative marketing strategies, and ability to turn challenges into opportunities. Her story serves as a reminder that education, while valuable, is not the sole determinant of success—grit, creativity, and hard work can carve a path to extraordinary achievements. Today, Barbara is not only celebrated as a real estate mogul but also as an investor, author, and inspirational figure to countless aspiring entrepreneurs.

These success stories illustrate that while education is valuable, it is not the sole determinant of achievement. These leaders relied on their ability to think innovatively, take calculated risks, and learn relentlessly from real-world experiences. Their journeys highlight the importance of self-belief, adaptability, and the courage to pursue one’s passions—qualities that transcend formal qualifications.

Such success stories remind us that each person can reach a higher potential through diverse paths. People can work toward educational credentials, but as Andrew taught us through this MasterClass, a person can also learn independently, and if the person is fueled with determination and self-directed work ethic, success may follow—even if a person starts in the struggle of a solitary prison cell.

After completing his formal education, Andrew's moved into his first job that put him into the world of sophisticated real estate investing. He worked for a niche business that acquired delinquent municipal tax liens—a space where Andrew quickly gained experience in asset valuation and the broader mechanisms of the real estate market. This role exposed him to countless property types, from single-family homes to commercial buildings and golf courses. He developed critical skills by analyzing each case to determine whether the unpaid taxes were worth purchasing.

Those who watch the accompanying video will see that Andrew eventually transitioned into a brokerage role, helping others trade or invest in distressed real estate assets. Realizing he could build a business offering advisory services while brokering deals, Andrew advanced into his first entrepreneurial venture, focusing on results-driven solutions for clients.

His early transactions often had small margins, but they deepened his expertise about adding value. Over time, he applied lessons learned to larger projects, including multimillion-dollar deals in real estate development.

He attributes much of his success to critical thinking and learning every aspect of his field—from construction to underwriting deals. Andrew noted that understanding both the financial and technical sides of real estate separates “finance people” from true “real estate people.” His hands-on knowledge helped him underwrite projects effectively, pursue off-market opportunities, and maximize returns by mitigating unnecessary costs.

Throughout his story, we got an example of the emphasis Andrew placed on incremental progress and self-directed learning. He encouraged students, even those in difficult circumstances like incarceration, to focus on building skills incrementally. He said, “You don’t need millions of dollars to pursue real estate. Start small, learn the trade, and grow over time.” His advice highlights the importance of patience—taking small, strategic steps early on to develop expertise and build a reputation for competence.

When I asked Andrew to provide us with an example of how he got off the ground, he showed us the importance of all the skills we teach in our introductory courses. The accumulated knowledge he built over time helped him to get the project off the ground and to cross the finish line, building a track record that would put him in line for bigger opportunities.

Think about all the steps that were necessary for Andrew to complete the transaction he described:

Conducted thorough market research to understand the local real estate trends and opportunities.
Analyzed the price per square foot that similar properties in the area were commanding.
Reverse engineered the financial model by estimating potential revenue and working backward to determine a feasible purchase price.
Identified an undervalued asset with strong potential for development and growth.
Secured funding and aligned financial resources to execute the purchase.
Navigated due diligence processes, including property inspections, zoning considerations, and legal reviews, to ensure a sound investment.
Crafted a detailed development plan, outlining necessary improvements and projected timelines.
Engaged with contractors, architects, and other professionals to bring the vision for the property to life.
Consistently monitored the progress of the development to stay on schedule and within budget.
Marketed the completed property effectively, leveraging its strengths to attract potential buyers or tenants.

Andrew’s success depended on mastering essential skills in math, English, and critical thinking. He needed to grasp the motivations of sellers, understand the goals of potential investors, and build strong connections with collaborative partners. Once he brought these elements together, he could confidently begin negotiations.

Recognizing that friends and family had money sitting in low-interest bank accounts, Andrew used his writing and communication skills to present them with a compelling opportunity. He demonstrated how they could earn significantly higher returns by investing with him. To address their concerns about risk, he explained how they could secure their investment with a lien on the asset, ensuring protection while he structured the deal.

Andrew developed a financial model illustrating how an investment of under $3 million could generate a return of over $1 million in a relatively short period. By showing them the stark contrast between earning less than 4% in a savings account and the potential for substantially greater returns through his plan, Andrew successfully persuaded his investors to provide the capital he needed to lead the deal.

Andrew told a compelling story, showcasing the value of working with “special-situation sellers,” who often value flexibility over market price. His firm coordinated with the seller’s timeline while actively working on permits and designs before closing the deal—all while avoiding holding costs.

Andrew’s belief in self-reliance and creating value for others aligns well with the lessons of the Straight-A Guide. He didn’t achieve his success overnight—it was the cumulative result of smaller successes over decades of learning, analyzing deals, and building his network. He believes that anyone can do what he did with the right mindset and a willingness to learn.

The world of business and investment real estate provides many examples of success stories like Andrews, they are the stories of masters. They show us that success often follows for those who become self-directed They don't wait for opportunities to come. They invest in personal development and put themselves on the pathway to new opportunities. This concept goes beyond just making money and focuses on building lasting wealth by creating value for others.

Some members of our community may need to complete their time in prison before pursuing opportunities in business or real estate. However, this doesn’t mean they can’t start preparing for a brighter future today. By learning from experts like Andrew, who share their knowledge and experience, they can begin investing in themselves through self-directed education. This could include learning about financial literacy, real estate strategies, or business fundamentals, all of which lay the foundation for future success. These efforts can empower individuals to rebuild their lives with confidence and purpose once they re-enter society.

Vocabulary Development

Mediocre – Of only average quality; not exceptional.
Asset Valuation – The process of determining a property or investment’s worth.
Underwriting – Assessing the value and risks of an investment.
Margins – The difference between costs and revenues in a transaction.
Returns – The profits generated from an investment.
Portfolio – A range of investments or assets held by a business or individual.
Entitlement – The process of gaining legal approval for a development project.
Execution – Successfully completing a plan or strategy.
Leverage – Using borrowed capital to amplify potential returns.
Critical Thinking – The process of analyzing and evaluating information to solve problems.

Self-Directed Reflection Questions

How can you define success for your situation, and what outcomes do you envision?
What lessons from Andrew’s story resonate with your aspirations?
How can self-directed learning help overcome obstacles you face today?
What skills can you build right now to increase your value in the future workplace?
How does having a strategic plan improve the likelihood of success in your goals?
What is one action you can take daily to develop better communication or financial skills?
How can taking on smaller projects drive incremental progress toward larger goals?
Why is aligning your goals with your values essential for long-term success?
How might understanding business fundamentals like financing or operations help in your future?
What systems can you implement to document measurable progress consistently?

Recommended Books

Rich Dad Poor Dad by Robert Kiyosaki

This book provides essential financial lessons, focusing on the critical distinction between building assets and accumulating liabilities. It emphasizes the importance of understanding the difference, with one of its key messages being: "The rich acquire assets. The poor and the middle class acquire liabilities, but they think they are assets." Through real-life examples and straightforward explanations, it illustrates how misidentifying liabilities as assets can hinder financial growth. The book helps readers grasp the concept of financial independence, offering practical advice on how managing cash flow and investing in true assets like real estate, stocks, or businesses can lead to lasting wealth. Andrew highly recommended this book as an excellent starting point for anyone seeking to shift their mindset about money. It encourages readers to think critically about financial decisions, break free from the cycle of living paycheck to paycheck, and make informed choices that build long-term wealth. This book provides insight for those who want to understand money, take control of their financial future, and lay the groundwork for financial freedom. It’s an inspiring resource for anyone committed to changing their financial trajectory.

The 7 Habits of Highly Effective People by Stephen Covey

A timeless classic in personal development, The Seven Habits provides practical guidelines for anyone striving to improve their life. The book emphasizes the significance of goal-setting, collaboration, and continuous self-growth. Its core message highlights that success stems from adhering to principles of personal and interpersonal effectiveness. The author offers clear, actionable strategies that seamlessly apply to both personal and professional domains, helping align actions with core values while striking a balance between productivity and meaningful relationships.

Through its guidance, readers can build a solid foundation for lasting success and personal fulfillment. A compelling example of these lessons comes from Andrew’s story, which illustrates how a disciplined, methodical approach to goal achievement can lead to transformative results. His journey underscores the value of incremental progress, consistent effort, and thoughtful planning.

With its blend of timeless wisdom and practical tools, The Seven Habits remains an indispensable resource for anyone eager to grow, thrive, and unlock their full potential across all areas of life.

You Can Negotiate Anything by Herb Cohen

This practical guide offers valuable and actionable techniques for mastering the art of negotiation, whether you're navigating everyday conversations or tackling high-stakes business deals. Drawing from real-world examples and proven strategies, it provides a roadmap to help you approach negotiations with confidence and finesse. One of the standout examples is Andrew’s experience in negotiating off-market deals, which emphasizes the transformative power of strong negotiation skills. By applying the right tactics, he was able to uncover and secure incredible opportunities that might have otherwise gone unnoticed. The guide explains how negotiation, when approached correctly, can become a powerful tool for creating win-win scenarios, strengthening relationships, and achieving your goals more effectively. Whether you're discussing a salary increase, closing a business deal, or resolving conflicts, this guide equips you with the insights needed to handle any negotiation with ease and success.

Recap of Straight-A Guide Lessons

Define Success – Andrew defined success as mastering financial and technical real estate knowledge. If you want to reach your highest potential, begin by defining success. Andrew aspired to become an entrepreneur and get involved in real estate, so he took methodical steps. What steps are you taking?
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Set Clear Goals – His education and small deals led to larger, strategic opportunities. Each incremental step he took would build upon the last. He could not enroll in graduate school if he didn't first complete undergraduate school. Without those credentials, he may not have found opportunities to work in sophisticated real estate transactions involved 100s of millions. What small goals are you pursuing today?
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Attitude – Andrew highlighted perseverance and a proactive mindset as critical to his growth. He wanted to create wealth, but that wasn't the only objective. Andrew appreciated opportunities to serve his community and create value. He enjoyed helping others see value in the vision he presented.
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Aspiration – His ambition to become a real estate expert guided his choice to pursue higher education. Even though he did not put much emphasis on school during his adolescence, he always saw himself as being successful, modeling the success of his father and others in his family. He wanted to bring them proud, and he followed their guidance of continuing his education, taking incremental steps to succeed.
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Action – He did not only talk about building success, Andrew took significant steps that would help him climb the ladder. He worked in several firms before he ventured out on his own to complete his first deal. Those lessons he learned along the way helped him build confidence and they also helped him tell the stories, building trust with people who would eventually play a role in getting him into multimillion-dollar deals.
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Accountability – Detailed record-keeping and self-assessment ensured sustained progress. Andrew had to hold himself accountable, especially once he ventured into his own deals. He spoke about the cost of money, and making sure that he was completing projects on time, and under budget. By holding himself accountable, he put himself in the position of more opportunities.
Awareness – Andrew identified off-market opportunities through his network. That was one example of keeping his head in the game. others always became aware of him. They turned to his expertise and offered to invest more resources, believing that if they invested in him, they would get a better return on their money than keeping it in a low-yield savings account.
Authenticity – His reputation for ethical, transparent practices made him a trusted advisor. He invested in himself first. That investment helped him tell a better story, showing that he knew how to create a plan, set priorities, then build tools, tactics, and resources that would lead to higher levels of success.
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Achievement – By leveraging each success, Andrew built a larger, thriving business. He began with a single-family house, but only after he had already worked in many types of real estate ventures. His depth and breadth of knowledge made him a master, convincing others that they should collaborate with him to achieve higher levels of success.
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Appreciation – He volunteers time to teach others and values opportunities to mentor. We're grateful to Andrew for taking the time to share his inspiring story with our audience, and also to collaborate in drafting this lesson with our nonprofit.

Sample Response

Question: How can self-directed learning help overcome obstacles you face today?

During my time in prison, I’ve been deeply committed to self-directed learning, constantly seeking out opportunities to grow and improve myself. That’s why I found this MasterClass lesson so impactful—it aligned perfectly with my personal journey of transformation and growth. Andrew’s examples were not theoretical. They provided practical, actionable insights that I can apply right now to my life and decision-making process. Although I may not yet have the opportunity to pursue jobs or career goals, I’m using this time to focus on planting the seeds for success. I’m determined to build a better future for myself once I’m released, and every bit of knowledge I gain now becomes a building block for that brighter tomorrow.

Andrew’s recommendations have inspired me to take action immediately. I’m going to begin by reading the books he suggested, immersing myself in the lessons they offer. These books represent a wealth of knowledge, and I want to fully absorb and internalize their teachings. To ensure I truly engage with the material, I’ve decided to write book reports for each one. These reports will help me reflect on what I’ve learned, analyze key takeaways, and consider how to apply those lessons to my own life. This process will not only deepen my understanding but also serve as a tangible record of my progress and commitment to growth.

To further document my progress and showcase my commitment to self-improvement, I’ve decided to develop a profile on Prison Professors Talent. This platform will allow me to highlight all that I’m learning through my independent efforts, inspired by Andrew’s guidance. By creating this profile, I can organize my achievements, share my reflections, and demonstrate how I’m actively working to apply new knowledge in meaningful ways. It will serve as a living testament to my dedication, providing a structured space to track my growth while motivating me to stay focused on my goals.

When I get out, I am determined to use my self-directed learning to persuade others to believe in me and my potential. My profile on Prison Professors Talent will be the foundation of this effort—a tangible representation of my work, growth, and commitment to change. By sharing this profile, I can provide a reason for others to believe in my ability to contribute in meaningful ways. Just as Andrew built a support network through his dedication and results, I aspire to do the same. I will connect with people who see the value in my efforts, building relationships rooted in trust, collaboration, and shared purpose. With their support, I hope to create new opportunities and demonstrate how positive change can lead to higher levels of achievement for myself and those around me.

Challenge

Build your profile on Prison Professors Talent. Show how every day in prison is an opportunity to reset and rebuild, emphasizing accountability and progress. Use your profile to show stakeholders why you’re extraordinary and a worthy candidate for freedom and opportunity.

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MasterClass with Andrew