MasterClass with Fawaad

Abstract

In this MasterClass, I introduce you to Fawaad, a successful entrepreneur who built a software company that generated tens of millions of dollars in annual revenue. He didn’t come from privilege, and he didn’t have a degree in computer science or engineering. Instead, he grew up in poverty, adopted at a young age, and often marginalized. Through perseverance, pattern recognition, and a relentless drive to create value, he learned how to seize opportunities in emerging markets and sell innovative solutions to some of the largest organizations in the world. Fawaad’s journey includes many setbacks. He tells us about losing every client during the 2009 recession, and later, making fear-based decisions during the COVID-19 pandemic that led to federal charges. Facing sentencing, he speaks candidly about what he learned from both his successes and his mistakes, and how he is now using those lessons to give back. His story offers strategies and encouragement to help you become the CEO of your own life, regardless of where you’re starting from or what challenges you face.

Detailed Narrative

I’ve never met Fawaad in person, but the way we connected says a lot about his character. Out of the blue, he reached out to our nonprofit—Prison Professors—not to ask for help, but to offer it. He told me he had learned about our mission to help people in prison prepare for success upon release. After doing his own research, he volunteered his time and energy to advance that mission. He offered to create a video for our community and to mentor me on ways we could expand our reach and make a bigger impact. That spirit of giving, especially from someone facing his own challenges, impressed me immediately. It also became the foundation for our collaboration on this MasterClass.

In this lesson, I want to share Fawaad’s story because it offers powerful lessons in resilience, reinvention, and being the CEO of your own life—even in the face of setbacks.

Fawaad didn’t grow up with privilege. His parents divorced when he was three years old, and he was adopted by his grandparents, who were already in their late fifties and sixties. They lived on food stamps and social security. There was no safety net, no college fund, no family business waiting for him. But what they did provide was an example of hard work. His grandfather worked as a maintenance man in a hospital, and his grandmother sanded furniture in a factory. Rather than talking about what it means to be successful, they worked hard and gave an example of what it meant to develop a strong work ethic.

As a child, Fawaad spent a lot of time alone. That solitude became fertile ground for creativity and reflection. He didn’t have the constant distractions of a large, close-knit family, and he learned to think independently. Even as a boy, he decided that his current circumstances were temporary—that his actions would shape his life.

Growing up half Arab in Arkansas came with its own challenges. Before 9/11, people often assumed he was Mexican. After 9/11, prejudice against Middle Easterners became a daily reality. Instead of letting discrimination define him, he focused on personal development, recognizing patterns, and finding opportunities to build value.

He wasn’t a perfect student—he graduated high school with a 2.9 GPA—but he earned a place in college and initially pursued a biology degree, with ambitions of becoming a surgeon. Midway through, he realized medicine wasn’t his calling. Around that time, he married his wife, who remains his partner to this day. With the added responsibility of providing for his family, he took a summer job at a car dealership.

At first, he hated the job. He didn’t like the stigma of car sales and didn’t consider himself good at the back-and-forth of negotiation. When he looked for other opportunities to add value, the dealership offered him a new role as “Internet Director,” allowing him to work from home. He seized the opportunity. 

Fawaad began researching the industry and discovered a key insight: in 2008, only 7% of dealership marketing budgets went to digital advertising. According to what he learned, within a few years, experts projected that number to more than 10x, jumping to 80%. 

In other words, if a car dealership spent $100,000 on marketing when he began, only $7,000 would go toward digital advertising. A few years later, however, dealerships would allocate $80,000 to digital marketing. 

This insight changed everything. Over the next eight months, he saved $40,000—no small feat during the Great Recession—and launched his own business. At first, his business offered more of a service than true software, but it delivered measurable results for clients. Over time, he transitioned into a software-as-a-service (SaaS) model, creating technology that large companies would pay to use month after month.

Over time, his company grew to target enterprise clients—huge organizations like the NBA and major automotive companies. As it matured, the company brought in between $50 million and $100 million in annual revenue. His software reached millions of end users.

That growth came over time, and to become successful, he had to navigate challenges effectively. For example, in late 2009, after he’d gotten his first taste of success, the market crashed. Practically overnight, he lost every client. Rather than give up, he pivoted. He focused on creating “uncancellable” products—core infrastructure like websites and automated systems that businesses couldn’t do without. His new strategy allowed him to rebuild his company. Over time, he added thousands of customers paying thousands of dollars each month.

By early 2020, the business thrived. Then, the COVID-19 pandemic led to a major challenge. Seemingly overnight, he lost about half of the company’s clients. They either paused or canceled their contracts within 90 days. Fear replaced creativity. Even though he had a viable business, fear of failure began to set in. To fortify the weakness, he applied for multiple government relief programs. While he qualified for some, he cut corners in the application process—failing to disclose existing loans on certain forms.

At the time, he was thinking about survival. He wanted to make sure that he would have the financial strength to overcome market weaknesses. Those were aberrant times. Rather than making decisions from a position of strength, Fawaad wanted to shore up his balance sheet with debt. He fully intended to repay the debt, but to qualify for the funding stream, he omitted information on the application forms. 

Consequences followed. 

As reflected, he said that he knew that it wasn’t the paperwork alone that got him into trouble—it was the mindset shift. Instead of innovating through the crisis, as he had done before, he reacted from fear. Prosecutors charged him crimes that exposed him to a potential prison term.

When we spoke, he was just nine days from sentencing, expecting to serve between four and six years in federal prison. Yet he spoke with clarity, humility, and determination. In fact, he had built the most innovative company of his career during the 14 months since receiving his target letter. He refused to let the government—or his own mistakes—define his future.

Fawaad shared a powerful example from a 1983 CIA study, which found that the most paralyzing thing you can tell a person is, “You’re too late.” In prison—or in life—it’s easy to believe that lie. But he urges people to reject it. It’s never too late to rebuild, reimagine, and come back stronger.

His journey—from poverty and prejudice to building a multimillion-dollar company, losing it all, rebuilding, and now facing prison—demonstrates that success isn’t about never falling. It’s about what you do when you get knocked down. That’s why I wanted to share his story in this MasterClass. He didn’t just reach out to volunteer for our mission—he lives it, by showing others that no matter where you start or what mistakes you make, you can still become the CEO of your own life.

Vocabulary Development

The following terms will help you strengthen your vocabulary and connect ideas from Fawaad’s story to your own journey. Learning and using new words will help you articulate your vision, goals, and plans more effectively—both while in custody and after release.

1. Enterprise Clients
   
   
   
   • Definition: Large organizations or corporations that purchase goods or services, often requiring customized solutions.
     
     
   • Context: Fawaad targeted enterprise clients like the NBA and major automotive companies because they offered bigger contracts and long-term relationships.
     
     
2. Software-as-a-Service (SaaS)
   
   
   
   • Definition: A software delivery model where applications are hosted online and customers pay a recurring subscription fee to use them.
     
     
   • Context: By shifting to a SaaS model, Fawaad created recurring revenue streams that allowed him to scale his business.
     
     
3. Pivot
   
   
   
   • Definition: To change strategy or direction in response to challenges or opportunities.
     
     
   • Context: After losing every client during the 2009 recession, Fawaad pivoted to creating “uncancellable” products to rebuild his company.
     
     
4. Uncancellable Products
   
   
   
   • Definition: Products or services that are essential to a client’s core operations and difficult to discontinue.
     
     
   • Context: Websites and automated inventory systems became Fawaad’s uncancellable products because clients needed them regardless of market conditions.
     
     
5. Market Insight
   
   
   
   • Definition: A deep understanding of trends, customer behavior, and industry shifts that can create opportunities.
     
     
   • Context: Fawaad’s recognition that dealership marketing budgets would shift massively to digital advertising was a market insight that launched his business.
     
     
6. Balance Sheet
   
   
   
   • Definition: A financial statement showing a company’s assets, liabilities, and equity at a specific point in time.
     
     
   • Context: During the pandemic, Fawaad sought to strengthen his balance sheet by applying for relief funding—even though fear influenced some of his choices.
     
     
7. Target Letter
   
   
   
   • Definition: A formal notice from a prosecutor informing a person that they are the target of a criminal investigation.
     
     
   • Context: Fawaad received a target letter 14 months before sentencing, which marked the beginning of his legal battle.
     
     
8. Pattern Recognition
   
   
   
   • Definition: The ability to observe and identify recurring trends, structures, or relationships that can inform decision-making.
     
     
   • Context: Fawaad’s skill in pattern recognition helped him spot opportunities and navigate business challenges.
     
     
9. Fear-Based Decision
   
   
   
   • Definition: A choice made primarily to avoid perceived threats or losses, often without fully considering long-term consequences.
     
     
   • Context: Fawaad admitted that applying for relief funds without full disclosure was a fear-based decision that didn’t align with his usual creative problem-solving.
     
     
10. Resilience
    
    
    
    • Definition: The ability to recover from setbacks, adapt to change, and keep moving forward.
      
      
    • Context: Fawaad’s resilience allowed him to rebuild his company after losing all his clients and to keep innovating even while facing prison.

Self-Directed Reflection Questions

1. Values — What do you stand for?
   
   
   
   • Fawaad demonstrated his values when he reached out to volunteer for our nonprofit while facing his own challenges.
     
     
   • Question: How can you live out your values right now, even in your current environment?
     
     
2. Goals — What are you working toward?
   
   
   
   • Fawaad’s early goal was to build a business by identifying a shift in dealership marketing budgets.
     
     
   • Question: What short-term and long-term goals can you set that will position you for success after release?
     
     
3. Attitude — How do you approach challenges?
   
   
   
   • Even after losing every client in 2009, Fawaad pivoted and rebuilt.
     
     
   • Question: When you face setbacks, do you react with excuses, or do you look for new strategies to adapt?
     
     
4. Aspiration — Who do you want to become?
   
   
   
   • Fawaad aspired to create value for large organizations and reach millions of end users with his software.
     
     
   • Question: If you could design your ideal future self, what qualities and skills would you have?
     
     
5. Action — What steps are you taking daily?
   
   
   
   • Fawaad’s success came from daily research, pattern recognition, and consistent outreach.
     
     
   • Question: What actions can you take every day—no matter how small—that move you toward your aspirations?
     
     
6. Accountability — How will you measure progress?
   
   
   
   • Fawaad measured business success through recurring revenue, client retention, and innovation.
     
     
   • Question: How will you hold yourself accountable for the actions you commit to each day?
     
     
7. Awareness — Are you observing opportunities?
   
   
   
   • Fawaad’s awareness of the coming digital marketing shift gave him a competitive advantage.
     
     
   • Question: What trends or patterns can you observe in your environment that could lead to future opportunities?
     
     
8. Authenticity — Are you being true to yourself?
   
   
   
   • Fawaad admits that fear-based decisions during the pandemic were out of character for him.
     
     
   • Question: What situations tempt you to act in ways that don’t align with your true values, and how can you resist them?
     
     
9. Achievement — How do you celebrate milestones?
   
   
   
   • From saving $40,000 in eight months to securing enterprise clients, Fawaad recognized each step forward as progress.
     
     
   • Question: What recent achievement, however small, can you acknowledge and build upon?
     
     
10. Appreciation — How do you express gratitude?
    
    
    
    • Despite facing prison, Fawaad expressed gratitude by volunteering to help our mission.
      
      
    • Question: Who or what can you show appreciation for today, and how will you do it?

Book Recommendations:

Reading is one of the most effective ways to build new skills, broaden your thinking, and prepare for opportunities after release. The three books below connect directly to lessons from Fawaad’s journey. They can help you strengthen your mindset, sharpen your decision-making, and develop the discipline needed to become the CEO of your own life.

1. The Alchemist — Paulo Coelho

Summary:
This classic novel follows Santiago, a young shepherd, who sets out in search of a treasure he believes is buried near the Egyptian pyramids. Along the way, he encounters challenges, meets mentors, and learns profound lessons about following one’s personal legend, trusting the journey, and recognizing that real treasure often lies in the growth we experience along the way.

Connection to Fawaad’s Story:
Fawaad identifies The Alchemist as the most influential book he’s ever read because it mirrors his own journey. Just like Santiago, he began without wealth or privilege, faced challenges, and relied on observation, persistence, and adaptability to move forward. Both stories show that the path to success is rarely straight, and detours often teach the most valuable lessons.

Self-Directed Use:
Use this book to reflect on your own “personal legend” — your ultimate goal or calling. Write down the setbacks you’ve faced, the lessons you’ve learned, and how they could be preparing you for your next opportunity. Share your reflections in your Prison Professors profile to inspire others.

2. The 5 AM Club — Robin Sharma

Summary:
Sharma uses a fictional narrative to teach the benefits of rising early, focusing on personal mastery, and establishing routines that maximize productivity. The story follows characters who learn from a mysterious mentor about the “20/20/20 Formula”: spending the first 20 minutes of the day moving, the next 20 minutes reflecting, and the final 20 minutes growing through learning.

Connection to Fawaad’s Story:
Fawaad credits The 5 AM Club for reinforcing the value of structured habits. His business success came from consistency—researching, networking, and innovating day after day. This mirrors the book’s core lesson: champions aren’t defined by occasional efforts, but by consistent, disciplined action.

Self-Directed Use:
Adapt the 20/20/20 formula to your prison schedule. Even without a clock, you can commit to starting each day with physical exercise, quiet reflection, and reading or study. Track your progress in a journal and share it in your profile to demonstrate discipline and self-improvement.

3. The Art of Living Consciously — Nathaniel Branden

Summary:
This book explores what it means to live with full awareness of your choices, actions, and values. Branden, a former protégé of Ayn Rand, emphasizes that self-esteem and personal integrity come from aligning behavior with consciously chosen principles.

Connection to Fawaad’s Story:
Fawaad recommends this book because it helped him reflect on the decisions that led to his legal trouble. It reinforced that even small compromises can have big consequences. His shift from creative problem-solving to fear-based decision-making during the pandemic was a departure from his core values—a lesson this book helps illuminate.

Self-Directed Use:
As you read, make a list of your core values. Compare them to your daily choices and note any gaps. Consider how you can bring your actions into closer alignment with your values, and document that process in your profile to show personal growth and integrity.

Straight-A Guide Recap — Lessons from Fawaad’s Life

The Straight-A Guide provides a framework for living with purpose, even in the most difficult circumstances. Fawaad’s journey reflects each principle in action—both in his successes and in the lessons learned from his mistakes.

1. Values – Live by principles that define who you are.
   
   
   
   • Lesson: Fawaad’s decision to reach out and volunteer for Prison Professors showed a commitment to giving, even while facing prison.
     
     
   • Reflection Prompt: What values can you live out today that will define you as someone who contributes rather than takes?
     
     
2. Goals – Set clear, measurable targets for your future.
   
   
   
   • Lesson: By identifying the coming shift in dealership marketing budgets, Fawaad set a goal to capture that opportunity, which launched his business.
     
     
   • Reflection Prompt: What measurable goal can you set now that will position you for success after release?
     
     
3. Attitude – Choose optimism and problem-solving over excuses.
   
   
   
   • Lesson: After losing every client in 2009, Fawaad didn’t quit—he pivoted to building “uncancellable” products.
     
     
   • Reflection Prompt: When you face a setback, what positive action can you take immediately to move forward?
     
     
4. Aspiration – Envision the best version of yourself.
   
   
   
   • Lesson: Fawaad aspired to serve enterprise clients and reach millions of end users, guiding his business decisions.
     
     
   • Reflection Prompt: Who is the best version of you, and what daily habits will help you become that person?
     
     
5. Action – Take consistent, daily steps toward your goals.
   
   
   
   • Lesson: Fawaad’s success came from constant research, networking, and innovation—work he did before he had a single client.
     
     
   • Reflection Prompt: What actions can you commit to taking every single day, no matter your environment?
     
     
6. Accountability – Measure your progress and own your results.
   
   
   
   • Lesson: Fawaad knew his numbers—recurring revenue, client retention, and growth—and used them to track success.
     
     
   • Reflection Prompt: How can you measure your progress so you know if you’re getting closer to your goals?
     
     
7. Awareness – Recognize opportunities in your environment.
   
   
   
   • Lesson: By spotting the digital marketing trend in 2008, Fawaad gained a major competitive advantage.
     
     
   • Reflection Prompt: What trends or needs do you see around you that could become opportunities?
     
     
8. Authenticity – Stay true to your core values.
   
   
   
   • Lesson: Fawaad admits that fear-based decisions during the pandemic went against his usual creative approach to business.
     
     
   • Reflection Prompt: How can you ensure your choices align with your authentic self, even under pressure?
     
     
9. Achievement – Celebrate progress, no matter how small.
   
   
   
   • Lesson: From saving $40,000 in eight months to securing major contracts, Fawaad marked each step forward.
     
     
   • Reflection Prompt: What recent achievement can you acknowledge today, and how will you build on it?
     
     
10. Appreciation – Live with gratitude and give back.
    
    
    
    • Lesson: Fawaad’s volunteer work with our nonprofit demonstrates that appreciation is expressed through service.
      
      
    • Reflection Prompt: Who can you thank or help today as an expression of your gratitude?
      
      

I’ll choose one of the reflection prompts from the recap and write a first-person answer as if I were a student in prison completing the lesson.

Sample Response

Reflection Prompt Chosen (Values): What values can you live out today that will define you as someone who contributes rather than takes?

Model Answer:

When I think about the kind of person I want to be, even while I’m in prison, I realize my values have to guide me. Right now, the most important value I can live out is service. I don’t have money, power, or freedom, but I do have time, attention, and experience. I can use those to help others around me.

I think about Fawaad’s decision to reach out to Prison Professors while facing his own challenges. He didn’t wait for “the perfect time” or for his legal problems to be over. He acted on his values immediately, even though it would have been easy for him to focus only on himself. That challenges me to do the same.

For me, living out service inside means listening when another guy needs to talk, helping someone write a letter, or showing a new arrival how to navigate the commissary process. None of those things cost me anything but time and attention, but they make a difference. It also means sharing what I’m learning through courses like this with people who might not otherwise have access.

I also value integrity. That means doing the right thing even when nobody’s watching. In here, that can be as simple as following through on a commitment, not taking shortcuts, and keeping my word. In a place where people often look for angles or ways to game the system, I want my daily actions to say, “I can be trusted.”

Finally, I value growth. I’m reading more books than I ever did on the street. I’m writing in my journal every day. I’m building habits that will serve me well when I’m home. I believe the way I live today is either strengthening or weakening my future. I want every choice to strengthen it.

I can’t change the past, but I can define my future by the values I live out now. Every day, I’m either contributing to the environment around me or taking from it. I want to be remembered here—and later—for being a contributor. That’s how I’ll know I’m living my values.

Challenge: Build Your Profile on Prison Professors

Fawaad’s story reminds us that setbacks don’t have to define the rest of our lives. Whether you’re in prison, on home confinement, or recently released, you can begin building a documented record of your growth right now. One of the most effective ways to do this is by creating and maintaining your profile on the Prison Professors platform.

Your profile is more than a digital page—it’s a living record of your values, goals, actions, and achievements. It can help you:

• Show decision-makers (judges, case managers, employers) evidence of your progress.
  
  
• Keep yourself accountable to the goals you’ve set.
  
  
• Inspire others by sharing your journey and lessons learned.
  
  

Here’s how to get started:

1. Write Your Biography
   
   
   
   • Tell your story in your own words, highlighting who you are, where you’ve been, and where you want to go.
     
     
   • Include challenges you’ve faced and the values you now live by.
     
     
2. Journal Regularly
   
   
   
   • Record your thoughts, lessons learned, and daily actions.
     
     
   • Show consistency and reflection over time.
     
     
3. Submit Book Reports
   
   
   
   • Read books that align with your growth goals.
     
     
   • Summarize the key lessons and how you plan to apply them.
     
     
4. Develop Your Release Plan
   
   
   
   • Outline the specific steps you’ll take to reintegrate successfully.
     
     
   • Include education, work, housing, and community service plans.
     
     
5. Track Points on the Leaderboard
   
   
   
   • Every submission—biography, journal entry, book report, release plan—earns points.
     
     
   • Use your points as tangible proof of your investment in yourself.
     
     

Why this matters:
Documenting your growth creates a body of work that speaks louder than any promise you could make. It shows that you’ve prepared intentionally for success, regardless of where you started or the mistakes you’ve made.

Like Fawaad, you can choose to give more than you take, even when you’re facing challenges. Your profile becomes evidence of that choice—something you can present with pride to anyone evaluating your readiness for the next chapter of your life.

Your challenge:
Start your profile today. Write your biography. Begin your first journal entry. Pick a book from this lesson’s reading list and write your report. Commit to building your record consistently. When you do, you’re not just preparing for release—you’re proving to yourself and others that you are the CEO of your own life.

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